The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations

The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations Sahaj A. Gandhi, Saurabh S. Soni, Urmila H. Patel, Deepali Kotadia This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-3903688/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract We describe the synthesis and crystal structure of DBZIW, 1,3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate, which crystallizes in a monoclinic system with space group P2 1 /c and Z = 4. The asymmetric unit contains a molecule of [C9 H11N2] + , an iodine ion I − , and a water molecule. Water oxygen O1 and iodine ion I − (O-H...I) connection display significant involvement in hydrogen bond interactions in the molecular packing of DBZIW. The network of C-H...O hydrogen bond contacts plays an essential part in the stability. The molecular structures 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ], 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW], 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI] and 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] were optimized at the B3LYP method with 6-311G (d, p) level using Gaussain-09 software. The energy band gap value of HOMO and LUMO of DBZ, DBZW, DBZI and DBZIW have 4.997 eV, 4.786 eV, 3.309 eV and 1.265 eV, respectively. The HOMO-LUMO energy gap, which is useful in determining the molecular electrical transport properties, explains the charge transfer interaction inside the molecule. The molecular docking studies indicated that DBZIW had high binding affinity for thyroid stimulating hormone receptor (TSHR) protein targets (4QT5). Benzimidazole Hydrogen bond interactions Energy frame work DFT calculations Molecular Docking Study Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 Figure 11 Figure 12 Figure 13 1. Introduction Benzimidazole has a very interesting heterocycle N which is commonly found in biological systems and naturally occurring cyanocobalamine. Because of their unique structural features and electron-rich environment, they are used by the pharmaceutical industry for drug discovery. Due to the numerous pharmacological properties of benzimidazole derivatives, including their antibacterial, antiviral, antioxidant, and anti-cancer activity, benzimidazole derivatives are important in the medical research [ 1 – 7 ]. In addition to their biological applications, benzimidazole derivatives have drawn a lot of attention in materials science because they may be crystallized to produce materials with remarkable conductivity and ferroelectric characteristics due to hydrogen bonds intra -intermolecular interactions [ 8 – 11 ]. Density functional theory (DFT) is now recognized as a significant method for researching the link between chemical and structural characteristics small molecules. [ 12 – 13 ]. In this context, and as part of our continuing study [ 14 – 18 ], into X-ray crystallography and computational chemical investigations of synthesized molecules, here we present the synthesis of a significant new derivative of benzimidazole, 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW], with an interest in spectroscopic characterization with single crystal X-ray diffraction study. We present the comparative studies of the X-ray diffraction data of the single crystal (Experimental) and the results of theoretical calculations for the analysis of their electronic structure, based on quantum chemical calculations using Gaussian software (Theoretical). To further research into the electronic and structural characteristics of the molecules, we calculated HOMO-LUMO orbital calculations and Hirshfeld surface analysis with 3D energy frameworks. 2. Experimental and Computational details 2.1 Synthesis : Synthesis of 1,3-dimethylbenzimidazolium iodide: Without additional purification, all reagents and solvents were used after being purchased from Sigma-Aldrich. THF (20 ml) was heated to 70°C while methyl iodide (12.2 mmol) and 1H-benzimidazole (12 mmol) were added. After 24 hours, added small amount of THF. Dichloromethane (DCM) (30 ml) was used to dissolve the oil, and KHCO 3 and around 3 ml of water were added. After the CO 2 evolution stopped, the mixture was mixed again, and a significant amount of KHCO 3 was added to absorb the water. THF was separated from the reaction mass after the solution had been heated to 70°C for 18 hours. After being cleaned with ether and dried, the product was left in the form of tiny crystals. 1 H NMR (CDCl3): (MeOD, δ/ppm relative to TMS) = 9.35 (s, 1H), 7.83–7.86 (m 2H), 7.61–7.65 (m 2H), 4.05 (s 6H); 13 C NMR (MeOD δ/ppm) = 142.6, 132.1, 126.7, 112.9, 32.8 2.2 Crystallographic analysis With graphite monochromatic MoKα radiation (λ = 0.71073) at 298(2) K, the data for the single crystal X-ray diffraction were obtained using a Bruker KAPPA APEX-II CCD-4 diffractometer in the ω-2θ scan mode. The Bruker SAINT software was used to obtain the cell refinements and data reductions [ 19 ]. In order to characterize the thermal motion that causes the non-hydrogen atoms to fall, the structure was first solved using direct methods using SHELXS-97 [ 20 ] and then refined using full-matrix least squares based on F 2 with anisotropic thermal parameters by using SHELXL-2016 [ 21 ]. The details of data collection refinement parameters are in Table S1 and take an image of one of the single crystals displayed in Fig. S1 . 2.3 Computational details We performed quantum chemical computations at a new level of theory to comprehend the role of water and I. DBZ, DBZW, DBZI, and DBZIW geometry optimization and associated frequency calculations were carried out using the B3LYP exchange-correlation functional with a 6-311 + g (d, p) basis set [ 22 , 23 ]. The Gaussian 09 package and the Gauss-View molecular visualization software were used for the computations [ 24 , 25 ]. 2.4 Hirshfeld surface analyses The software Crystal Explorer [ 26 – 27 ] includes a useful feature for describing molecule surface properties. Using Crystal Explorer and calculated energy framework, investigated the qualitative and quantitative data for molecular interaction of the quinazoline derivative. 2.5 Molecular Docking Study Iodine is a widely used antiseptic and is on the World Health Organization (WHO) list of essential medications since the body cannot produce it on its own [ 28 ]. It is also an essential component of our diet. Iodine is a crucial component for the synthesis of thyroid hormones. The body cannot produce thyroid hormones if there is not enough iodine present. Iodine shortage during pregnancy consequently has the potential to cause goiter, hypothyroidism, and intellectual impairments in children and newborns. The thyroid stimulating hormone receptor (TSHR) was chosen as the target molecule based on literature reviews [ 29 – 30 ] and research; its structure was retrieved using protein Data Bank (PDB) ID 4QT5 presented in the Fig. S2. Hex software [ 31 ], an interactive programme for molecular docking study. Hex is able to read PDB files for protein structures and SDF files for small molecules. Table S3 lists the docking parameters that Hex software utilized to compute a molecular docking research. 3. Results and Discussion 3.1 Crystal structure The title compound, 1,3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate, C 9 H 13 N 2 IO, crystallizes in a monoclinic system with space group P2 1 /c and Z = 4, with one molecule having one H 2 O molecule in the asymmetric unit. The lattice parameters are a = 8.9323(4), b = 7.1654(3), c = 17.6425(8) Ǻ and β = 101.432(2) °. An ‘ORTEP’ view of the compound with an atomic numbering scheme (thermal ellipsoids drown at a 50% probability level) is shown in Fig. 2 . The stability of the molecule is due to the network of C-H…O, O-H…I and π-π interactions. The geometry of intra and intermolecular hydrogen bond interactions tabulated in Table 1 . In molecular packing, halogen I and oxygen of water molecules play a dominant role. The halogen I and oxygen of water molecules contribute alternately to the molecular packing by forming O-H…I dimer with water oxygen as the donor water molecule and iodine stacks in a fashion to form a channel held up by O-H…I hydrogen bond interactions of 2.765(7) Å as shown in Fig. 3 . The intra molecular interactions involving donor C2 via H2A and C6 via H6 with acceptor water molecule oxygen OW1 generate a pseudo ring of R 1 2 (7) graph set motifs. A weak but significant π-π stacking interaction involving the centroid of the five membered imidazole ring (x, y, z) and the six membered phenyl ring at 1-x, -1-y, 1-z with the Cg-Cg distance of 3.642(2) Å contributes to the molecular packing additionally (Fig. 4 ). Table 1 Hydrogen bond interactions of the title molecule (distances in, angles in°) A. Hydrogen bond interactions D-H...A d(D-H ) Ǻ d (D-A) Ǻ d (H- A) Ǻ (D-H...A)˚ C2-H2A…OW1 (i) 0.960(4) 3.519(7) 2.660(6) 149.19(29) C6-H6…OW1 (i) 0.930(4) 3.620(8) 2.786(6) 149.68(28) OW1- H1B…I (ii) 0.859(5) 3.647(4) 2.883(4) 158.69(20) B . π-π interaction Cg(I)- Cg(J) Cg(I)…Cg(J)Ǻ α β γ Cg(I)…P Ǻ Cg(1)- Cg(2) (iii) 3.642(2) 0.45 12.49 12.17 3.5604 D. Symmetry Code (i) x , y , z ;(ii) x,1 + y,z ; (iii) -x + 2,-y,-z + 1 Note : Cg (1) and Cg(2) represents the centroid of the rings (N1-C1-N2-C4-C5) and (C4-C5-C6-C7-C8-C9) respectively. 3.2 Hirshfeld Surface analysis The strength and function of hydrogen bonds as well as other intra and intermolecular interactions have been calculated using Hirshfeld surface analysis, and their significance for the stability of the crystal lattice has been estimated. Figure 5 (a-c) illustrates, Hirshfeld surface of the molecule DBZIW, shows that surfaces have been mapped over a d norm (range of 0.03 to 0.95), di (range of 1.06–2.59), and de (range of 1.06–2.61). Red indicates shorter contacts, white depicts the contact surrounding the VDW (Van Deer Waals) separation, and blue is for longer contacts on Hirshfeld surfaces 3D mapped with d norm . The d norm surface depicts the close contacts of hydrogen bonds, indicating that intensive red spots correspond to C-H...O and C-H...I hydrogen bond interactions as revealed in Fig. 5 d. The 2D fingerprint plots that estimate the different patterns of interaction in the crystalline network have illustrated in Fig. 6 . In general, intermolecular interactions H⋯H are most abundant in the crystalline frame [51.1% (Fig. 6 a)]. H⋯I contact are the another most significant interactions because of the abundance of hydrogen on the molecular surface [27.5% (Fig. 6 b)]. The Van der Waals' forces have a vital influence on the stabilization of the packaging in the crystalline structure. The Hirshfeld surfaces have been influenced by further inter-contacts, including C⋯C (7.1%) (Fig. 6 c), O⋯H (4.6%) (Fig. 6 d), N⋯C (4.2%) (Fig. 6 e), C⋯H (3.8%) (Fig. 6 f), I⋯O (1.2%) (Fig. 6 g) and N⋯H (0.5%) (Fig. 6 h). The stability of the molecular structure depends on the energy of intermolecular interactions, which has been assessed using energy framework analysis using the Crystal Explorer software. The monomer wave function, estimated by the B3LYP/6-31G (d, P) level using Crystal Explorer, was used to quantify the intermolecular interactions. The results were reported together with the likely involved intermolecular interactions for the various energies (Table 2 ). Total interaction energy results from the interactions of coulomb, polarization, dispersion, and repulsion, calculated for a molecule cluster with a chosen molecule radius of 3.8. According to the data in Table 3 , the dispersion component significantly contributes to each interaction, and followed by the electrostatic, polarization, dispersion, and repulsion energies, respectively. It has become abundantly evident that the dispersion energy, which has an important function to play, is what most significantly contributes to molecular stability. In Fig. 7 , the energy frameworks E elec (red), E disp (green), and E total (blue) are used to illustrate the magnitudes of intermolecular interactions graphically. Table 2 Molecular pairs and the interaction energies (kJ/mole) obtained from energy framework calculation for the title molecule. Total energies, reported for benchmarked energy model, are the sum of the four energy components. Sr. No. N Symop R Electron Density E_ele E_pol E_dis E_rep E_tot 1 1 -x, -y, -z 8.94 B3LYP/6-31G(d, p) -0.6 -0.4 -6.4 6.6 -2.5 2 0 -x, -y, -z 8.93 B3LYP/6-31G(d, p) -0.4 -0.2 -2.6 0.6 -2.5 3 1 x, y, z 8.93 B3LYP/6-31G(d, p) -0.5 -0.2 -5.3 1.6 -4.3 4 1 -x, -y, -z 3.81 B3LYP/6-31G(d, p) 3.1 -5.9 -46.5 20.7 -28.8 5 0 -x, y + 1/2, -z + 1/2 8.85 B3LYP/6-31G(d, p) -0.4 -0.3 -4.3 2.7 -2.7 6 0 -x, -y, -z 3.79 B3LYP/6-31G(d, p) 3.1 -5.8 -46.0 20.2 -28.6 7 0 -x, -y + 1/2, z + 1/2 8.82 B3LYP/6-31G(d, p) -0.6 -0.3 -6.3 2.3 -4.8 3.3 Computational studies 3.3.1 Optimized geometry 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ] (a), 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW] (b) 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI] (c) and 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] (d) structures were optimized at the B3LYP method with 6-311G (d, p) level using Gaussain-09 software as shown in Fig. 8 . By optimizing the benzimidazole derivatives both with and without iodine and water, it was possible to get to the conclusion regarding the involvement of these molecules in the benzimidazole derivatives. Table 3 compares the computed bond lengths and bond angles of (a) DBZ, (b) DBZW, (c) DBZI, and (d) DBZIW with experimental X-ray data on bond lengths and bond angles. Table 3 Bond lengths (Å) and bond angles (°) involving non-hydrogen atoms based on X-ray data and computational calculations at the B3LYP /6-311G (d, p) level of theory (with estimated standard deviation in brackets). Bond lengths (Å) Experimental X-ray Theoretical calculations at B3LYP /6-311G (d, p) level of theory DBZIW DBZ DBZW DBZI DBZIW N1- C1 1.330(4) 1.3928 1.4058 1.3709 1.3723 N1- C2 1.461(4) 1.4429 1.4475 1.4654 1.4334 N1- C5 1.392(4) 1.3843 1.3765 1.4098 1.4158 N2- C1 1.331(4) 1.3939 1.4099 1.3808 1.4158 N2- C3 1.463(4) 1.4421 1.4458 1.4653 1.4311 N2- C4 1.392(4) 1.3807 1.3821 1.4098 1.4156 C4- C5 1.378(5) 1.4179 1.4174 1.4196 1.4488 C4- C9 1.396(5) 1.3916 1.3899 1.4016 1.3997 C5- C6 1.386(5) 1.3919 1.3936 1.4016 1.3979 C6 -C7 1.364(6) 1.3883 1.4097 1.4076 1.3874 C7 -C8 1.412(7) 1.4103 1.3901 1.4157 1.4044 C8 -C9 1.371(6) 1.4103 1.4084 1.4076 1.3908 Bond Angles (°) X-ray DBZ DBZW DBZI DBZIW C1- N1- C5 108.1(3) 109.3977 109.8646 108.3002 108.0977 C1- N1- C2 125.8(3) 123.5164 124.1667 123.5946 126.1173 C5- N1- C2 126.1(3) 127.0859 125.0423 125.9256 125.785 C1- N2- C4 108.0(3) 109.3322 109.55 108.3028 108.0663 C1- N2- C3 126.3(3) 125.4505 123.0036 123.6115 125.9066 C4- N2- C3 125.7(3) 125.2173 124.6258 125.9131 126.0094 N1- C1- N2 110.2(3) 106.7967 104.9892 109.0936 110.5965 C5- C4- N2 106.9(3) 107.4000 107.1278 106.7765 106.5914 C5- C4- C9 121.9(3) 121.4302 121.0412 121.4453 120.5588 N2- C4- C9 131.1(3) 131.1698 131.8198 131.7777 132.8475 C4- C5- C6 122.2(3) 120.7732 121.046 121.4425 120.8197 C4- C5- N1 106.7(3) 107.0734 107.298 106.7731 106.6475 C6- C5- N1 131.2(3) 132.1534 131.6411 131.7839 132.5317 C7- C6- C5 116.3(4) 117.6327 117.6012 117.1697 117.5386 C6- C7- C8 121.9(4) 121.4985 121.2589 121.3859 121.5767 C9-C8- C7 121.7(4) 121.1995 121.278 121.3861 122.4264 C8-C9- C4 115.9(4) 117.4659 117.7618 117.169 117.0779 H11-OW1- H12 117(2) 105.1749 103.235 As of Table 3 , The data showed that all of the optimized bond lengths and bond angles were a little bit bigger than the values obtained through experimentation. because the computational theoretical data related to the isolated molecule in the gas phase while the experimental data were obtained in the solid phase. The highest bond length difference is 0.063 Å (DBZ), 0.0785 Å (DBZW), 0.0494 Å (DBZI) and 0.0844 Å for the N2-C1 bond, while the biggest bond angle deviation occurred in the N1-C1-N2 at angle 3.433° in DBZ and 5.248° in DBZW, respectively, while in DBZI, the biggest bond angle deviation occurred in the C1-N2-C3 at angle 2.7185° and at the N2-C4-C9 angle (1.7175°) in DBZIW. The root means square error (RMSE) of the DBZ, DBZW, DBZI, and DBZWI is found to be approximately 0.032, 0.039, 0.029, and 0.039, respectively. This result shows that the theoretically calculated bond lengths (using the B3LYP method) have the strongest correlations with experimental values. For bond angles, DBZ, DBZW, DBZI, and DBZWI, respectively, have root mean square errors of 0.819°, 0.856°, 0.594°, and 0.999°. Figures 9 and 10 show, respectively, the correlation between experimental and theoretical bond lengths and bond angles of the molecules DBZ, DBZW, DBZI, and DBZWI. 3.3.2 Mulliken Charge Distributions The Mulliken population analysis was used to determine the atomic charge values of the molecules (DBZ, DBZW, DBZI, and DBZWI), which are summarised in Table 4 and visually depicted in Fig. 11 . The charge on hydrogen atoms is all positive. It should be noted that the DBZI and DBZWI molecules have an iodine atom and, in comparison to the other atoms in the molecule, have the highest negative charges of -0.60193 and − 0.74247, respectively. The water molecules are backbone in the DBZW and DBZWI in the molecule and because of this has both DBZW (-0.53454) and DBZIW (-0.46966) oxygen atoms were negatively charged. In all benzimidazole derivatives, all nitrogen atoms had a negative charge whereas all hydrogen atoms had a positive charge. Donor and acceptor atoms are signs that intra- and intermolecular hydrogen bonds are present in the solid-state phase. Table 4 Mulliken charges (e) for the atoms of DBZ, DBZW, DBZI and DBZWI molecules ATOMS DBZ DBZW DBZI DBZIW I -0.60193 -0.74247 N1 -0.03461 -0.002774 -0.1289 -0.09337 N2 -0.01864 -0.02806 -0.12916 -0.104 C1 -0.07311 -0.03283 -0.19938 0.028577 H1 0.128545 0.116349 0.338816 0.226445 C2 -0.2554 -0.26967 -0.56808 -0.09805 H21 0.103443 0.194071 0.279819 0.159468 H22 0.115347 0.15801 0.21308 0.109528 H23 0.115182 0.143092 0.225498 0.105733 C3 -0.39278 -0.25423 -0.56796 -0.08762 H31 0.095871 0.142793 0.27992 0.126884 H32 0.149501 0.146388 0.225396 0.106709 H33 0.16318 0.164884 0.213102 0.113662 C4 0.116478 0.405221 0.276394 -0.06205 C5 0.368051 -0.02368 0.27641 -0.03217 C6 -0.2864 -0.44445 -0.32647 -0.10556 H6 0.163157 0.139092 0.235951 0.194352 C7 -0.406 -0.35792 -0.20369 -0.17555 H7 0.155808 0.123774 0.227746 0.273841 C8 -0.26451 -0.33676 -0.20365 -0.08115 H8 0.162911 0.120627 0.227727 0.157892 C9 -0.2689 -0.26207 -0.32656 -0.1275 H9 0.162882 0.108327 0.235901 0.139896 OW1 -0.53454 -0.46966 H11 0.252062 0.188588 H12 0.326734 0.247576 FMO analysis In order to comprehend the frontier effect of water and iodine, if present in benzimidazole derivatives, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) studies of the benzimidazole derivatives, (a) DBZ, (b) DBZW, (c) DBZI, and (d) DBZIW were conducted. HOMO-LUMO explains a variety of reactions in conjugated systems and is used to predict the most reactive location in π-electron systems using the frontier electron density. FMO analysis is commonly used to describe the optical and electrical properties of organic compounds. To understand the nature of the electronic transition, the electron density plots of HOMO and LUMO are presented in Fig. 8 . The energy band gap value of HOMO and LUMO of DBZ, DBZW, DBZI and DBZIW have 4.997 eV, 4.786 eV, 3.309 eV and 1.265 eV, respectively. In molecular interactions, the HOMO stands for electron donors, and its energy is related to the ionization potential (IP), while the LUMO stands for electron acceptors, and its energy is related to the electron affinity (EA). The HOMO-LUMO energy gap, which is useful in determining the molecular electrical transport properties, explains the charge transfer interaction inside the molecule [ 32 – 34 ]. Table 5 lists the predicted HOMO and LUMO energies as well as additional characteristics. Thus, it is clear from Table 5 that DBZ is hard, more stable and less reactive, while compound BDZIW is soft and the least stable and more reactive compare to others. The HOMO-LUMO energy gap decreases from molecule DBZ to DBZW to DBZI and the minimum energy gap is achieved with Water and I substituent in DBZ. Thus, this substituent increases the reactivity of the benzimidazole derivative. Table 5 HOMO and LUMO energies and global reactivity descriptors calculated for DBZ, DBZW, DBZI and DBZIW Parameters DBZ DBZW DBZI DBZWI HOMO (eV) -4.800 -5.232 -4.946 -4.006 LUMO (eV) 0.197 -0.445 -1.637 -2.740 Energy Gap (eV) 4.997 4.786 3.309 1.265 Ionization Potential 4.800 5.232 4.946 4.006 Electron affinity -0.197 0.445 1.637 2.740 Chemical Potential µ 2.301 2.838 3.291 3.373 Electron negativity χ (eV) -2.301 -2.838 -3.291 -3.373 Hardness η (eV) 2.499 2.393 1.655 0.633 Softness (S) 0.400 0.418 0.604 1.581 Electrophilicity index (ω) 6.617 9.641 8.962 3.599 Maximum electronic charge -0.921 -1.186 -1.989 -5.332 Total Energy (A.U.) -459.784 -536.255 -470.413 0.116 Dipole moment (Debye) 2.303 4.777 9.037 21.894 3.4 Molecular docking study We looked into a molecular docking study of 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ], 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW], 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI], and 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodide monohydrate [DBZIW] for further explore the role of water and I in the benzimidazole derivatives. The protein crystal structure for the thyroid stimulating hormone receptor (TSHR) was chosen (PDB ID 4QT5), and the Hex software was used to carry out the benzimidazole derivative inhibitor. We used the protein crystal structures as the protein targets, downloaded from the protein data bank. A docking calculation was performed to determine the docking score for benzimidazole derivatives with protein crystal structures separately with the HEX software [ 34 – 35 ]. The energy values obtained by the docking study are tabulated in Table 6 and presented in Fig. 13 . The best ligand structure, DBZIW (-191.91), fitted the receptors. Due to the presence of water and Iodine, DBZIW has more reactive compare to other molecular ligands. The docking score data, which also predicts the activity of the pharmacological molecule, indicates the binding energy necessary to form a bond between the ligand and receptor. The in vitro antibacterial activity of the synthesized DBZIW compound was evaluated using the dilution technique against bacterial strains and shown in figure S3 and tabulated in Table S3. Table 6 The energy values of DBZ, DBZW, DBZI, and DBZWI molecules obtained by the docking study Compound Name 4QT5 DBZ -161.20 DBZW -173.43 DBZI -161.31 DBZWI -191.91 4. Conclusion In this work we described the crystal structure of 1, 3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] capable of forming H-bonds. DBZIW organized in weak π–π stacked interaction involving the centroid of the five membered imidazole ring with six membered phenyl ring and simultaneously stabilized by chains of intermolecular O-H…I dimer interactions with water molecule and iodine stacks in a fashion to form channel hold up by O-H…I hydrogen bond interactions. The intermolecular hydrogen bonding interactions that contribute to the molecular stability were highlighted by the Hirshfeld surface analysis, and the 2D fingerprint map revealed the proportion of intermolecular contacts of the molecule, showing that H⋯H (51.1%) and I⋯H (27.5%) intermolecular interactions are the most prevalent in the crystal lattice. The energy framework study revealed the corresponding energies for the intermolecular interactions that were involved and it was found that the dispersion energy contributes maximum for each molecular pair for the stability of the structure. To support analysis of the molecular structure and role of the presence of I and water in the molecular structure [DBZIW], we optimized structures (DBZIW, DBZ, DBZI and DBZW) using DFT methods. The iodine atom has the largest negative charge in the entire molecule, according to an analysis of Mulliken charge distributions, which may have led to the occurrence of interactions involving particular atom of the molecule. HOMO-LUMO orbital analysis and the energy band gap demonstrated charge transfer inside the molecule, and computed lowest HOMO-LUMO band gap for the molecule DBZIW leads to intriguing electronic properties. Molecular docking analysis revealed better docking score of benzimidazole derivative (DBZWI) with 4qt5 protein crystal suggests more advantages for further pharmacological applications as specially for I molecule. Declarations Supplementary Data CCDC 1508765 contains the supplementary crystallographic data for the compound. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html , or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,UK;fax: (+ 44) 1223-336-033; or e-mail: [email protected] Conflict of interest The authors declare no conflict of interest. Author Contribution Dr. Sahaj A Gandhi wrote the manuscript text mainly, corrected by Dr. U H Patel, supervisor. All the crystallography and DFT work carried out by Dr. Sahaj A. Gandhi. Dr. S. S. Soni and Dr. Deepli Kotadia were synthesized the compounds and characterized by H1 NMR and IR. Acknowledgements We thankful to DST, New Delhi for supporting the FIST project at the Department of Physics, Sardar Patel University, Vallabh Vidyanagar, Gujarat, India, by providing the single-crystal X-ray diffractometer (Kappa Apex -II) equipment. References Nardi M, Cano NCH, Simeonov S, Bence R, Kurutos A, Scarpelli R, Wunderlin D (2023) Procopio Catalysts 13:392 Kuş C, Sözüdönmez F, Can-Eke B, Coban T (2010) Z Naturforsch C J Biosci 65:537 Bansal Y, Silakari O (2012) Bioorg Med Chem 20:6208 Ates-Alagoz Z (2013) Curr Med Chem 20:4633 Ayhan-Kilcigil G, Kuş C, Çoban T, Özdamar ED, Can-Eke B (2014) Arch Pharm (Weinheim) 347:276 Główka ML, Kałużyńska S, Krause M, Gobis K, Foks H, Szczesio M, Olczak A (2018) Acta Cryst C74:1684 Mani GS, Anchi P, Sunkari S, Donthiboina K, Godugu C, Shankaraiah N, Kamal A (2020) Bioorg Med Chem Lett 30:127432 Xiong JF, Li JX, Mo GZ, Huo JP, Liu JY, Chen XY, Wang ZY (2014) J Org Chem 79:11619 Cosby T, Holt A, Griffin PJ, Wang Y, Sangoro J (2015) J Phys Chem Lett 6:3961 Cho H, Song J, Shin JW, Moon J, Kwon BH (2021) l. Lee, N. S. Opt Express 29:23131 Kerru N, Gummidi L, Maddila S, Gangu KK (2020) S B Jonnalagadda Molecules 25:1909 Javed M, Farhat A, Jabeen S, Khera RA, Khalid M (2021) J Iqbal Comput Theoretical Chem 1204:113373 Tanaka A, Nakashima K (2011) Y Miura Tetrahedron 67:2260 Patel UH, Gandhi SA (2011) Indian J Pure Appl Phys 49:263 Patel UH, Gandhi SA, Patel BD, Modh RD, Patel RH, Yadav J, Desai KR (2013) Indian J Pure Appl Phys 51:819 Patel UH, Gandhi SA, Barot VM, Patel MC (2013) Cryst Struct Theory Appl 2:167 Patel UH, Gandhi SA, Barot VM, Patel MC (2016) Mol Cryst Liq Cryst 624:190 Gandhi SA, Patel UH, Modh RD, Naliyapara Y, Patel AS (2016) J Chem Crystallogr 46:387 Bruker (2001) Program name. Bruker AXS Inc., Madison, Wisconsin, USA Sheldrick GM (2013) Acta Crystallogr A 64:112 G. M. Sheldrick Acta Crystallogr A 71 3 (2015) Wałęsa R, Kupka T (2015) M Broda Struct Chem 26:1083 Rives T, Julian, William J (2008) J Chem Theory Comput 4:297 Gaussian 09 RA, 02 MJ, Frisch GW, Trucks HB, Schlegel GE, Scuseria MA, Robb JR, Cheeseman G, Scalmani V, Barone B, Mennucci GA, Petersson H, Nakatsuji M, Caricato X, Li HP, Hratchian AF, Izmaylov J, Bloino G, Zheng JL, Sonnenberg M, Hada M, Ehara K, Toyota R, Fukuda J, Hasegawa M, Ishida T, Nakajima Y, Honda O, Kitao H, Nakai T, Vreven JA, Montgomery KN Jr., Kudin VN, Staroverov R, Kobayashi J, Normand K, Raghavachari A, Rendell JC, Burant SS, Iyengar J, Tomasi M, Cossi N, Rega JM, Millam M, Klene JE, Knox JB, Cross V, Bakken C, Adamo J, Jaramillo R, Gomperts RE, Stratmann O, Yazyez AJ, Austin R, Cammi C, Pomelli JW, Octerski RL, Martin K, Morokuma VG, Zakrzewski GA, Voth P, Salvador, Dannenberg S, Dapprich A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009 Dennington R, Keith T, Millam J (2009) GaussView, Version 5, Shawnee Mission KS. Semichem Inc. Spackman PR, Turner MJ, McKinnon JJ, Wolff SK, Grimwood DJ, Jayatilaka D (2021) M Spackman J Appl Cryst 54:1006 Goodwin MJ, Steed BW, Yufit DS, Musa OM, Berry DJ (2017) J W Steed Cryst Growth Des 17:5552 Chen C, Hubbard PA, Salazar LM, McLachlan SM, Murali R (2015) B Rapoport Mol Endocrinol 29:99 Li M, Zhou Q, Pan Y, Lan X, Zhang Q, Pan C (2023) C Mao Anim Biotechnol 34:658 Yu Y, Liu QQ, Liu DY, Wang DD, Yang LQ, Ye SM (2021) Experimental Therapeutic Med 22:1 Miar M, Shiroudi A, Pourshamsian K, Oliaey AR, Hatamjafari F (2021) J Chem Res 45:147 Bernard M, Alexandre Alain S, Lilienfeld V, Anatole O (2022) Mater Adv 3:8306 Padmaja L, Ravikumar C, Sajan D, Hubert JI, Jayakumar VS, Pettit GR, Faurskov NO (2009) J Raman Spectrosc 40:419 Ritchie DW Hex 6.3 User Manual Protein Docking Using Spherical Polar Fourier Correlations Copyright c, 1996–2010 Ghoorah AW, Devignes M-D, Smaïl-Tabbone M, Ritchie DW (2013) Proteins 81 2150 Additional Declarations No competing interests reported. Supplementary Files Graphicalabstract.png Index Abstract The X-ray crystal structure of 1, 3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW], is reported, and the water molecule oxygen and iodine ion I - (O-H…I) relation shows a leading role in hydrogen bond interactions. SupportingInformation.docx Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-3903688","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":270783538,"identity":"8216ca8e-b146-4a08-9bdc-f248a283a518","order_by":0,"name":"Sahaj A. Gandhi","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAA0klEQVRIiWNgGAWjYFACHgYGCYb/ciDmgQckaGE2BmtJIFoLAwNzYgOIIkqLfPvZgx8sfrGlzw87/BBoi52cbgMBLQZn8pIlJPt4cjfeTjMAakk2NjtASAtDjoGEZI9E7sbZCSAtBxK3EdIi3//G+Idkj0G64ez0D8RpYbiRYyYh8SMhQV46h0hbDG68MbOQbDhguEE6p+BAggERfpHvzzG+LfHngLz87PTNHz5U2MkR1AICzJJtQOvAKg2IUA4CjB/+AK1rIFL1KBgFo2AUjDwAAJbvRsWEQRZ7AAAAAElFTkSuQmCC","orcid":"","institution":"Bhartiya Vidya Bhavan’s Shri Ishvarlal L P Arts Science and J Shah Commerce College","correspondingAuthor":true,"prefix":"","firstName":"Sahaj","middleName":"A.","lastName":"Gandhi","suffix":""},{"id":270783539,"identity":"6e8077e3-fa82-485d-b6e1-ad933fcc525e","order_by":1,"name":"Saurabh S. Soni","email":"","orcid":"","institution":"Sardar Patel University","correspondingAuthor":false,"prefix":"","firstName":"Saurabh","middleName":"S.","lastName":"Soni","suffix":""},{"id":270783540,"identity":"b07eb815-5267-4c93-a354-73f7d23da229","order_by":2,"name":"Urmila H. Patel","email":"","orcid":"","institution":"Sardar Patel University","correspondingAuthor":false,"prefix":"","firstName":"Urmila","middleName":"H.","lastName":"Patel","suffix":""},{"id":270783541,"identity":"592d6c85-ca36-42f3-8042-a6b4283a4e3e","order_by":3,"name":"Deepali Kotadia","email":"","orcid":"","institution":"Sardar Patel University","correspondingAuthor":false,"prefix":"","firstName":"Deepali","middleName":"","lastName":"Kotadia","suffix":""}],"badges":[],"createdAt":"2024-01-27 17:46:38","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-3903688/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-3903688/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":50751046,"identity":"ddc34483-031a-45c5-a1ed-0c80d7400aaa","added_by":"auto","created_at":"2024-02-06 17:34:01","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":19950,"visible":true,"origin":"","legend":"\u003cp\u003eThe reaction scheme of the title compound\u003c/p\u003e","description":"","filename":"floatimage1.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/b2556d9bc0cc4aa7d5202289.png"},{"id":50751045,"identity":"ac29ce2a-ff84-4295-8960-4c01ff84dc04","added_by":"auto","created_at":"2024-02-06 17:34:01","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":35911,"visible":true,"origin":"","legend":"\u003cp\u003edepicts 50% probability displacement ellipsoids in the ORTEP diagram\u003c/p\u003e","description":"","filename":"floatimage2.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/5d12c074b771f2f371c862db.png"},{"id":50751952,"identity":"73bde5d2-3a80-49f0-84e7-839e532d4202","added_by":"auto","created_at":"2024-02-06 17:42:02","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":475075,"visible":true,"origin":"","legend":"\u003cp\u003eThe molecular packing by forming O-H…I dimer with water oxygen as the donor water molecule and iodine stacks in a fashion to form channel hold up by O-H…I hydrogen bond interactions showing (a) by ball and stick diagram (b) by space fill diagram\u003c/p\u003e","description":"","filename":"floatimage3.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/850a1bf5f22277c5a00cc907.png"},{"id":50751047,"identity":"870117d8-c20a-43dc-b8a0-214a3b1cf8b8","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":383130,"visible":true,"origin":"","legend":"\u003cp\u003eThe weak π–π stacked interaction involving the centroid of the five membered imidazole ring with six membered phenyl ring with Cg-Cg separation distance of 3.642(2) Å showing (a) by ball and stick diagram (b) by space fill diagram\u003c/p\u003e","description":"","filename":"floatimage4.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/ada68f4cacbca1bb7ad87085.png"},{"id":50751048,"identity":"e88206cb-a7e2-4090-8825-f80ccb1f190a","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":1126597,"visible":true,"origin":"","legend":"\u003cp\u003eThe Hirshfeld surface of the compound mapped with (a) \u003cem\u003ed\u003c/em\u003e\u003csub\u003e\u003cem\u003enorm\u003c/em\u003e\u003c/sub\u003e\u0026nbsp; (b) \u003cem\u003ed\u003c/em\u003e\u003csub\u003e\u003cem\u003ei \u003c/em\u003e\u003c/sub\u003eand (c) \u003cem\u003ed\u003c/em\u003e\u003csub\u003e\u003cem\u003ee \u003c/em\u003e\u003c/sub\u003e(d) d\u003csub\u003enorm\u003c/sub\u003e surface depicts the close contacts of hydrogen bonds indicating that intensive red spots correspond to intra and inter molecular C-H…O and C-H…I hydrogen bonds.\u003c/p\u003e","description":"","filename":"floatimage5.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/681d8c3ef3f6cf3368d06349.png"},{"id":50751053,"identity":"726a3449-8f29-4747-a525-0722d7788d43","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":433055,"visible":true,"origin":"","legend":"\u003cp\u003eAtom-atom interactions and their contribution through two-dimensional fingerprint plots for the title compound, showing (a) H⋯H (b) I⋯H/H…I (c) C⋯C (d) H⋯O/O⋯H (e) N⋯C/C⋯N, (f) C⋯H/H⋯C (g) I⋯O/O…I and (h) H⋯N/N⋯H inter­actions.\u003c/p\u003e","description":"","filename":"floatimage6.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/41f52ef4b51281d5c978a6c9.png"},{"id":50751957,"identity":"79d9e210-0d36-4329-9da9-e14f6782081a","added_by":"auto","created_at":"2024-02-06 17:42:02","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":402138,"visible":true,"origin":"","legend":"\u003cp\u003eEnergy-framework diagrams for (a) E\u003csub\u003eelec\u003c/sub\u003e, (b) E\u003csub\u003edisp.\u003c/sub\u003e and (c) E\u003csub\u003etot.\u003c/sub\u003e for the titled molecule with B3LYP/6-31G method. All diagrams use the same cylinder scale of 100 for energies.\u003c/p\u003e","description":"","filename":"floatimage7.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/b7defc99967e734bd9474a4b.png"},{"id":50752580,"identity":"0b9a1b4e-1c6d-48ff-8255-842da365d35f","added_by":"auto","created_at":"2024-02-06 17:50:02","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":651520,"visible":true,"origin":"","legend":"\u003cp\u003eOptimized geometry structures (a) DBZ (b) DBZW (c) DBZI and (d) DBZIW\u003c/p\u003e","description":"","filename":"floatimage8.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/835748ced0e852d0ef28fcd0.png"},{"id":50752581,"identity":"9c074abc-8bd8-41fe-bba9-8fe3056c39b1","added_by":"auto","created_at":"2024-02-06 17:50:02","extension":"png","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":173331,"visible":true,"origin":"","legend":"\u003cp\u003eGraphical representation of correlation between experimental versus theoretical bond lengths of (a) DBZ (b) DBZW (c) DBZI and (d) DBZIW\u003c/p\u003e","description":"","filename":"floatimage9.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/44502b588a15150f3b27b619.png"},{"id":50751050,"identity":"10508b58-845c-4411-a5eb-10cec407c8dc","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":10,"title":"Figure 10","display":"","copyAsset":false,"role":"figure","size":313131,"visible":true,"origin":"","legend":"\u003cp\u003eGraphical representation of correlation between experimental versus theoretical bond angles of (a) DBZ (b) DBZW (c) DBZI and (d) DBZIW\u003c/p\u003e","description":"","filename":"floatimage10.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/796d02b09c5a26c88eb9d471.png"},{"id":50751057,"identity":"d63a2850-00f5-4951-b1b4-1d19d9268e8e","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":11,"title":"Figure 11","display":"","copyAsset":false,"role":"figure","size":256826,"visible":true,"origin":"","legend":"\u003cp\u003eGraph sheets of Mulliken charges (e) for atoms of molecules (a) DBZ, (b) DBZW, (c) DBZI and (d) DBZIW\u003c/p\u003e","description":"","filename":"floatimage11.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/48ce44079c8b4999af70bda2.png"},{"id":50751953,"identity":"3fb91228-0dc0-41be-9bbc-d652b6f8cd3d","added_by":"auto","created_at":"2024-02-06 17:42:02","extension":"png","order_by":12,"title":"Figure 12","display":"","copyAsset":false,"role":"figure","size":430857,"visible":true,"origin":"","legend":"\u003cp\u003eHighest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of (a) DBZ, (b) DBZW, (c) DBZI and (d) DBZIW\u003c/p\u003e","description":"","filename":"floatimage12.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/da828786fedb08c3a67ddcbc.png"},{"id":50751056,"identity":"934e1e5b-badb-4c30-8e03-b13e6a9a3652","added_by":"auto","created_at":"2024-02-06 17:34:02","extension":"png","order_by":13,"title":"Figure 13","display":"","copyAsset":false,"role":"figure","size":802052,"visible":true,"origin":"","legend":"\u003cp\u003eMolecular docking interactions between the iron-binding protein (PDB code 4qt5) receptor with (a) DBZ, (b) DBZW, (c) DBZI and (d) DBZWI\u003c/p\u003e","description":"","filename":"floatimage13.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/3f96450f5a216ef0352e987a.png"},{"id":51972395,"identity":"ccd0f606-a60f-4454-bdfc-cba621d4aa0f","added_by":"auto","created_at":"2024-03-04 18:56:26","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":6126534,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/4da2ffa1-4a14-4b84-97fd-3fc4f08b2129.pdf"},{"id":50751955,"identity":"06ca1389-993d-4ba6-b8c2-ebf0a7f0acdc","added_by":"auto","created_at":"2024-02-06 17:42:02","extension":"png","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":386787,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eIndex Abstract\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe X-ray crystal structure of 1, 3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW], is reported, and the water molecule oxygen and iodine ion I\u003csup\u003e-\u003c/sup\u003e (O-H…I) relation shows a leading role in hydrogen bond interactions.\u003c/p\u003e","description":"","filename":"Graphicalabstract.png","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/525ce09d8a861cba22c07c59.png"},{"id":50752582,"identity":"1699e567-2cbc-4def-b87d-5a36b16445b9","added_by":"auto","created_at":"2024-02-06 17:50:02","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":342706,"visible":true,"origin":"","legend":"","description":"","filename":"SupportingInformation.docx","url":"https://assets-eu.researchsquare.com/files/rs-3903688/v1/fbe77e5d807966288c56afb9.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eBenzimidazole has a very interesting heterocycle N which is commonly found in biological systems and naturally occurring cyanocobalamine. Because of their unique structural features and electron-rich environment, they are used by the pharmaceutical industry for drug discovery. Due to the numerous pharmacological properties of benzimidazole derivatives, including their antibacterial, antiviral, antioxidant, and anti-cancer activity, benzimidazole derivatives are important in the medical research [\u003cspan additionalcitationids=\"CR2 CR3 CR4 CR5 CR6\" citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e]. In addition to their biological applications, benzimidazole derivatives have drawn a lot of attention in materials science because they may be crystallized to produce materials with remarkable conductivity and ferroelectric characteristics due to hydrogen bonds intra -intermolecular interactions [\u003cspan additionalcitationids=\"CR9 CR10\" citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e]. Density functional theory (DFT) is now recognized as a significant method for researching the link between chemical and structural characteristics small molecules. [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. In this context, and as part of our continuing study [\u003cspan additionalcitationids=\"CR15 CR16 CR17\" citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e], into X-ray crystallography and computational chemical investigations of synthesized molecules, here we present the synthesis of a significant new derivative of benzimidazole, 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW], with an interest in spectroscopic characterization with single crystal X-ray diffraction study.\u003c/p\u003e \u003cp\u003eWe present the comparative studies of the X-ray diffraction data of the single crystal (Experimental) and the results of theoretical calculations for the analysis of their electronic structure, based on quantum chemical calculations using Gaussian software (Theoretical). To further research into the electronic and structural characteristics of the molecules, we calculated HOMO-LUMO orbital calculations and Hirshfeld surface analysis with 3D energy frameworks.\u003c/p\u003e"},{"header":"2. Experimental and Computational details","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003e\u003cb\u003e2.1 Synthesis\u003c/b\u003e: Synthesis of 1,3-dimethylbenzimidazolium iodide:\u003c/h2\u003e \u003cp\u003eWithout additional purification, all reagents and solvents were used after being purchased from Sigma-Aldrich. THF (20 ml) was heated to 70\u0026deg;C while methyl iodide (12.2 mmol) and 1H-benzimidazole (12 mmol) were added. After 24 hours, added small amount of THF. Dichloromethane (DCM) (30 ml) was used to dissolve the oil, and KHCO\u003csub\u003e3\u003c/sub\u003e and around 3 ml of water were added. After the CO\u003csub\u003e2\u003c/sub\u003e evolution stopped, the mixture was mixed again, and a significant amount of KHCO\u003csub\u003e3\u003c/sub\u003e was added to absorb the water. THF was separated from the reaction mass after the solution had been heated to 70\u0026deg;C for 18 hours. After being cleaned with ether and dried, the product was left in the form of tiny crystals.\u003c/p\u003e \u003cp\u003e \u003csup\u003e1\u003c/sup\u003eH NMR (CDCl3): (MeOD, δ/ppm relative to TMS)\u0026thinsp;=\u0026thinsp;9.35 (s, 1H), 7.83\u0026ndash;7.86 (m 2H), 7.61\u0026ndash;7.65 (m 2H), 4.05 (s 6H); \u003csup\u003e13\u003c/sup\u003eC NMR (MeOD δ/ppm)\u0026thinsp;=\u0026thinsp;142.6, 132.1, 126.7, 112.9, 32.8\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e2.2 Crystallographic analysis\u003c/h2\u003e \u003cp\u003eWith graphite monochromatic MoKα radiation (λ\u0026thinsp;=\u0026thinsp;0.71073) at 298(2) K, the data for the single crystal X-ray diffraction were obtained using a Bruker KAPPA APEX-II CCD-4 diffractometer in the ω-2θ scan mode. The Bruker SAINT software was used to obtain the cell refinements and data reductions [\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]. In order to characterize the thermal motion that causes the non-hydrogen atoms to fall, the structure was first solved using direct methods using SHELXS-97 [\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e] and then refined using full-matrix least squares based on F\u003csup\u003e2\u003c/sup\u003e with anisotropic thermal parameters by using SHELXL-2016 [\u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e]. The details of data collection refinement parameters are in Table \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e and take an image of one of the single crystals displayed in Fig. \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e2.3 Computational details\u003c/h2\u003e \u003cp\u003eWe performed quantum chemical computations at a new level of theory to comprehend the role of water and I. DBZ, DBZW, DBZI, and DBZIW geometry optimization and associated frequency calculations were carried out using the B3LYP exchange-correlation functional with a 6-311\u0026thinsp;+\u0026thinsp;g (d, p) basis set [\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e, \u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e]. The Gaussian 09 package and the Gauss-View molecular visualization software were used for the computations [\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e, \u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e2.4 Hirshfeld surface analyses\u003c/h2\u003e \u003cp\u003eThe software Crystal Explorer [\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e] includes a useful feature for describing molecule surface properties. Using Crystal Explorer and calculated energy framework, investigated the qualitative and quantitative data for molecular interaction of the quinazoline derivative.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003e2.5 Molecular Docking Study\u003c/h2\u003e \u003cp\u003eIodine is a widely used antiseptic and is on the World Health Organization (WHO) list of essential medications since the body cannot produce it on its own [\u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e28\u003c/span\u003e]. It is also an essential component of our diet. Iodine is a crucial component for the synthesis of thyroid hormones. The body cannot produce thyroid hormones if there is not enough iodine present. Iodine shortage during pregnancy consequently has the potential to cause goiter, hypothyroidism, and intellectual impairments in children and newborns. The thyroid stimulating hormone receptor (TSHR) was chosen as the target molecule based on literature reviews [\u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e29\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e] and research; its structure was retrieved using protein Data Bank (PDB) ID 4QT5 presented in the Fig. S2. Hex software [\u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e], an interactive programme for molecular docking study. Hex is able to read PDB files for protein structures and SDF files for small molecules. Table S3 lists the docking parameters that Hex software utilized to compute a molecular docking research.\u003c/p\u003e \u003c/div\u003e"},{"header":"3. Results and Discussion","content":"\u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003e3.1 Crystal structure\u003c/h2\u003e \u003cp\u003eThe title compound, 1,3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate, C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eIO, crystallizes in a monoclinic system with space group P2\u003csub\u003e1\u003c/sub\u003e/c and Z\u0026thinsp;=\u0026thinsp;4, with one molecule having one H\u003csub\u003e2\u003c/sub\u003eO molecule in the asymmetric unit. The lattice parameters are a\u0026thinsp;=\u0026thinsp;8.9323(4), b\u0026thinsp;=\u0026thinsp;7.1654(3), c\u0026thinsp;=\u0026thinsp;17.6425(8) Ǻ and β\u0026thinsp;=\u0026thinsp;101.432(2) \u0026deg;. An \u0026lsquo;ORTEP\u0026rsquo; view of the compound with an atomic numbering scheme (thermal ellipsoids drown at a 50% probability level) is shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e. The stability of the molecule is due to the network of C-H\u0026hellip;O, O-H\u0026hellip;I and π-π interactions. The geometry of intra and intermolecular hydrogen bond interactions tabulated in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. In molecular packing, halogen I and oxygen of water molecules play a dominant role. The halogen I and oxygen of water molecules contribute alternately to the molecular packing by forming O-H\u0026hellip;I dimer with water oxygen as the donor water molecule and iodine stacks in a fashion to form a channel held up by O-H\u0026hellip;I hydrogen bond interactions of 2.765(7) \u0026Aring; as shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e. The intra molecular interactions involving donor C2 via H2A and C6 via H6 with acceptor water molecule oxygen OW1 generate a pseudo ring of \u003cem\u003eR\u003c/em\u003e\u003csup\u003e\u003cem\u003e1\u003c/em\u003e\u003c/sup\u003e\u003csub\u003e\u003cem\u003e2\u003c/em\u003e\u003c/sub\u003e \u003cem\u003e(7)\u003c/em\u003e graph set motifs. A weak but significant π-π stacking interaction involving the centroid of the five membered imidazole ring (x, y, z) and the six membered phenyl ring at 1-x, -1-y, 1-z with the Cg-Cg distance of 3.642(2) \u0026Aring; contributes to the molecular packing additionally (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eHydrogen bond interactions of the title molecule (distances in, angles in\u0026deg;)\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"9\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colspan=\"9\" nameend=\"c9\" namest=\"c1\"\u003e \u003cp\u003eA. Hydrogen bond interactions\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c2\" namest=\"c1\"\u003e \u003cp\u003eD-H...A\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e \u003cp\u003ed(D-H ) Ǻ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c6\" namest=\"c5\"\u003e \u003cp\u003ed (D-A) Ǻ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c8\" namest=\"c7\"\u003e \u003cp\u003ed (H- A) Ǻ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e(D-H...A)˚\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c2\" namest=\"c1\"\u003e \u003cp\u003eC2-H2A\u0026hellip;OW1 (i)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e \u003cp\u003e0.960(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c6\" namest=\"c5\"\u003e \u003cp\u003e3.519(7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c8\" namest=\"c7\"\u003e \u003cp\u003e2.660(6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e149.19(29)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c2\" namest=\"c1\"\u003e \u003cp\u003eC6-H6\u0026hellip;OW1 (i)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e \u003cp\u003e0.930(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c6\" namest=\"c5\"\u003e \u003cp\u003e3.620(8)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c8\" namest=\"c7\"\u003e \u003cp\u003e2.786(6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e149.68(28)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c2\" namest=\"c1\"\u003e \u003cp\u003eOW1- H1B\u0026hellip;I (ii)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e \u003cp\u003e0.859(5)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c6\" namest=\"c5\"\u003e \u003cp\u003e3.647(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c8\" namest=\"c7\"\u003e \u003cp\u003e2.883(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e158.69(20)\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"9\" nameend=\"c9\" namest=\"c1\"\u003e \u003cp\u003e\u003cb\u003eB\u003c/b\u003e. \u003cb\u003eπ-π interaction\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCg(I)- Cg(J)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003eCg(I)\u0026hellip;Cg(J)Ǻ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003eα\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003eβ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003eγ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003eCg(I)\u0026hellip;P Ǻ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCg(1)- Cg(2) (iii)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c3\" namest=\"c2\"\u003e \u003cp\u003e3.642(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003e0.45\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colspan=\"2\" nameend=\"c7\" namest=\"c6\"\u003e \u003cp\u003e12.49\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e12.17\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e3.5604\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"9\" nameend=\"c9\" namest=\"c1\"\u003e \u003cp\u003e\u003cb\u003eD. Symmetry Code\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"9\" nameend=\"c9\" namest=\"c1\"\u003e \u003cp\u003e(i) \u003cem\u003ex\u003c/em\u003e, \u003cem\u003ey\u003c/em\u003e, \u003cem\u003ez\u003c/em\u003e ;(ii) \u003cem\u003ex,1\u0026thinsp;+\u0026thinsp;y,z\u003c/em\u003e; (iii) \u003cem\u003e-x\u0026thinsp;+\u0026thinsp;2,-y,-z\u0026thinsp;+\u0026thinsp;1\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colspan=\"9\" nameend=\"c9\" namest=\"c1\"\u003e \u003cp\u003e\u003cb\u003eNote\u003c/b\u003e: \u003cem\u003eCg (1)\u003c/em\u003e and \u003cem\u003eCg(2)\u003c/em\u003e represents the centroid of the rings (N1-C1-N2-C4-C5) and (C4-C5-C6-C7-C8-C9) respectively.\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec10\" class=\"Section2\"\u003e \u003ch2\u003e3.2 Hirshfeld Surface analysis\u003c/h2\u003e \u003cp\u003eThe strength and function of hydrogen bonds as well as other intra and intermolecular interactions have been calculated using Hirshfeld surface analysis, and their significance for the stability of the crystal lattice has been estimated. Figure\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e(a-c) illustrates, Hirshfeld surface of the molecule DBZIW, shows that surfaces have been mapped over a d\u003csub\u003enorm\u003c/sub\u003e (range of 0.03 to 0.95), di (range of 1.06\u0026ndash;2.59), and de (range of 1.06\u0026ndash;2.61). Red indicates shorter contacts, white depicts the contact surrounding the VDW (Van Deer Waals) separation, and blue is for longer contacts on Hirshfeld surfaces 3D mapped with d\u003csub\u003enorm\u003c/sub\u003e. The d\u003csub\u003enorm\u003c/sub\u003e surface depicts the close contacts of hydrogen bonds, indicating that intensive red spots correspond to C-H...O and C-H...I hydrogen bond interactions as revealed in Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003ed.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe 2D fingerprint plots that estimate the different patterns of interaction in the crystalline network have illustrated in Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e. In general, intermolecular interactions H⋯H are most abundant in the crystalline frame [51.1% (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003ea)]. H⋯I contact are the another most significant interactions because of the abundance of hydrogen on the molecular surface [27.5% (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003eb)]. The Van der Waals' forces have a vital influence on the stabilization of the packaging in the crystalline structure. The Hirshfeld surfaces have been influenced by further inter-contacts, including C⋯C (7.1%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003ec), O⋯H (4.6%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003ed), N⋯C (4.2%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003ee), C⋯H (3.8%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003ef), I⋯O (1.2%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003eg) and N⋯H (0.5%) (Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003eh).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe stability of the molecular structure depends on the energy of intermolecular interactions, which has been assessed using energy framework analysis using the Crystal Explorer software. The monomer wave function, estimated by the B3LYP/6-31G (d, P) level using Crystal Explorer, was used to quantify the intermolecular interactions. The results were reported together with the likely involved intermolecular interactions for the various energies (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e). Total interaction energy results from the interactions of coulomb, polarization, dispersion, and repulsion, calculated for a molecule cluster with a chosen molecule radius of 3.8. According to the data in Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, the dispersion component significantly contributes to each interaction, and followed by the electrostatic, polarization, dispersion, and repulsion energies, respectively. It has become abundantly evident that the dispersion energy, which has an important function to play, is what most significantly contributes to molecular stability. In Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e, the energy frameworks E\u003csub\u003eelec\u003c/sub\u003e (red), E\u003csub\u003edisp\u003c/sub\u003e (green), and E\u003csub\u003etotal\u003c/sub\u003e (blue) are used to illustrate the magnitudes of intermolecular interactions graphically.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eMolecular pairs and the interaction energies (kJ/mole) obtained from energy framework calculation for the title molecule. Total energies, reported for benchmarked energy model, are the sum of the four energy components.\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"10\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c7\" colnum=\"7\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c8\" colnum=\"8\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c9\" colnum=\"9\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c10\" colnum=\"10\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eSr.\u003c/p\u003e \u003cp\u003eNo.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eN\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eSymop\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eR\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eElectron Density\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eE_ele\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c7\"\u003e \u003cp\u003eE_pol\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c8\"\u003e \u003cp\u003eE_dis\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c9\"\u003e \u003cp\u003eE_rep\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c10\"\u003e \u003cp\u003eE_tot\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, -y, -z\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.94\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-0.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-0.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-6.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e6.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-2.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, -y, -z\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-0.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-0.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-2.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e0.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-2.5\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003ex, y, z\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-0.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-0.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-5.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e1.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-4.3\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, -y, -z\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e3.81\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e3.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-5.9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-46.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e20.7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-28.8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, y\u0026thinsp;+\u0026thinsp;1/2, -z\u0026thinsp;+\u0026thinsp;1/2\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.85\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-0.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-0.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-4.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e2.7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-2.7\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, -y, -z\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e3.79\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e3.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-5.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-46.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e20.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-28.6\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003cem\u003e-x, -y\u0026thinsp;+\u0026thinsp;1/2, z\u0026thinsp;+\u0026thinsp;1/2\u003c/em\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.82\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eB3LYP/6-31G(d, p)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-0.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c7\"\u003e \u003cp\u003e-0.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c8\"\u003e \u003cp\u003e-6.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c9\"\u003e \u003cp\u003e2.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c10\"\u003e \u003cp\u003e-4.8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec11\" class=\"Section2\"\u003e \u003ch2\u003e3.3 Computational studies\u003c/h2\u003e \u003cdiv id=\"Sec12\" class=\"Section3\"\u003e \u003ch2\u003e3.3.1 Optimized geometry\u003c/h2\u003e \u003cp\u003e1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ] (a), 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW] (b) 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI] (c) and 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] (d) structures were optimized at the B3LYP method with 6-311G (d, p) level using Gaussain-09 software as shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e. By optimizing the benzimidazole derivatives both with and without iodine and water, it was possible to get to the conclusion regarding the involvement of these molecules in the benzimidazole derivatives. Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e compares the computed bond lengths and bond angles of (a) DBZ, (b) DBZW, (c) DBZI, and (d) DBZIW with experimental X-ray data on bond lengths and bond angles.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab3\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eBond lengths (\u0026Aring;) and bond angles (\u0026deg;) involving non-hydrogen atoms based on X-ray data and computational calculations at the B3LYP /6-311G (d, p) level of theory (with estimated standard deviation in brackets).\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eBond lengths (\u0026Aring;)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eExperimental\u003c/p\u003e \u003cp\u003eX-ray\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"4\" nameend=\"c6\" namest=\"c3\"\u003e \u003cp\u003eTheoretical calculations at B3LYP /6-311G (d, p) level of theory\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eDBZIW\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDBZ\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDBZW\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eDBZI\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eDBZIW\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN1- C1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.330(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.3928\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.4058\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.3709\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e1.3723\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN1- C2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.461(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.4429\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.4475\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.4654\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e1.4334\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN1- C5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.392(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.3843\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.3765\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.4098\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e1.4158\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN2- C1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.331(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.3939\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.4099\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.3808\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e1.4158\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN2- C3\u003c/p\u003e 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-C7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.364(6)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.3883\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.4097\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.4076\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e1.3874\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC7 -C8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1.412(7)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.4103\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.3901\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e 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colname=\"c5\"\u003e \u003cp\u003e108.3002\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e108.0977\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC1- N1- C2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e125.8(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e123.5164\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e124.1667\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e123.5946\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e126.1173\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC5- N1- C2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e126.1(3)\u003c/p\u003e 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align=\"left\" colname=\"c2\"\u003e \u003cp\u003e106.9(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e107.4000\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e107.1278\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e106.7765\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e106.5914\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC5- C4- C9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e121.9(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e121.4302\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e121.0412\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e121.4453\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e120.5588\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eN2- C4- C9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e131.1(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e131.1698\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e131.8198\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e131.7777\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e132.8475\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC4- C5- C6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e122.2(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e120.7732\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e121.046\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e121.4425\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e120.8197\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC4- C5- N1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e106.7(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e107.0734\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e107.298\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e106.7731\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e106.6475\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC6- C5- N1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e131.2(3)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e132.1534\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e131.6411\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e131.7839\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e132.5317\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC7- C6- C5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e116.3(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e117.6327\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e117.6012\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e117.1697\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e117.5386\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC6- C7- C8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e121.9(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e121.4985\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e121.2589\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e121.3859\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e121.5767\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC9-C8- C7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e121.7(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e121.1995\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e121.278\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e121.3861\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e122.4264\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eC8-C9- C4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e115.9(4)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e117.4659\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e117.7618\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e117.169\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e117.0779\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eH11-OW1- H12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e117(2)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e105.1749\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e103.235\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eAs of Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, The data showed that all of the optimized bond lengths and bond angles were a little bit bigger than the values obtained through experimentation. because the computational theoretical data related to the isolated molecule in the gas phase while the experimental data were obtained in the solid phase. The highest bond length difference is 0.063 \u0026Aring; (DBZ), 0.0785 \u0026Aring; (DBZW), 0.0494 \u0026Aring; (DBZI) and 0.0844 \u0026Aring; for the N2-C1 bond, while the biggest bond angle deviation occurred in the N1-C1-N2 at angle 3.433\u0026deg; in DBZ and 5.248\u0026deg; in DBZW, respectively, while in DBZI, the biggest bond angle deviation occurred in the C1-N2-C3 at angle 2.7185\u0026deg; and at the N2-C4-C9 angle (1.7175\u0026deg;) in DBZIW. The root means square error (RMSE) of the DBZ, DBZW, DBZI, and DBZWI is found to be approximately 0.032, 0.039, 0.029, and 0.039, respectively. This result shows that the theoretically calculated bond lengths (using the B3LYP method) have the strongest correlations with experimental values. For bond angles, DBZ, DBZW, DBZI, and DBZWI, respectively, have root mean square errors of 0.819\u0026deg;, 0.856\u0026deg;, 0.594\u0026deg;, and 0.999\u0026deg;. Figures\u0026nbsp;\u003cspan refid=\"Fig9\" class=\"InternalRef\"\u003e9\u003c/span\u003e and \u003cspan refid=\"Fig10\" class=\"InternalRef\"\u003e10\u003c/span\u003e show, respectively, the correlation between experimental and theoretical bond lengths and bond angles of the molecules DBZ, DBZW, DBZI, and DBZWI.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec13\" class=\"Section3\"\u003e \u003ch2\u003e3.3.2 Mulliken Charge Distributions\u003c/h2\u003e \u003cp\u003eThe Mulliken population analysis was used to determine the atomic charge values of the molecules (DBZ, DBZW, DBZI, and DBZWI), which are summarised in Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e and visually depicted in Fig.\u0026nbsp;\u003cspan refid=\"Fig11\" class=\"InternalRef\"\u003e11\u003c/span\u003e. The charge on hydrogen atoms is all positive. It should be noted that the DBZI and DBZWI molecules have an iodine atom and, in comparison to the other atoms in the molecule, have the highest negative charges of -0.60193 and \u0026minus;\u0026thinsp;0.74247, respectively.\u003c/p\u003e \u003cp\u003eThe water molecules are backbone in the DBZW and DBZWI in the molecule and because of this has both DBZW (-0.53454) and DBZIW (-0.46966) oxygen atoms were negatively charged. In all benzimidazole derivatives, all nitrogen atoms had a negative charge whereas all hydrogen atoms had a positive charge. Donor and acceptor atoms are signs that intra- and intermolecular hydrogen bonds are present in the solid-state phase.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab4\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eMulliken charges (e) for the atoms of DBZ, DBZW, DBZI and DBZWI molecules\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"5\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eATOMS\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eDBZ\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDBZW\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDBZI\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eDBZIW\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eI\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.60193\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.74247\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eN1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.03461\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.002774\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.1289\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.09337\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eN2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.01864\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.02806\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.12916\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.104\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.07311\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.03283\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.19938\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.028577\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.128545\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.116349\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.338816\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.226445\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.2554\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.26967\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.56808\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.09805\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH21\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e 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\u003cp\u003e\u003cb\u003eH23\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.115182\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.143092\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.225498\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.105733\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC3\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.39278\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.25423\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.56796\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.08762\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH31\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.095871\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.142793\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.27992\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.126884\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH32\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.149501\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.146388\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.225396\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.106709\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH33\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.16318\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.164884\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.213102\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.113662\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC4\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.116478\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.405221\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.276394\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.06205\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC5\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.368051\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.02368\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.27641\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.03217\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC6\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.2864\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.44445\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.32647\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.10556\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH6\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.163157\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.139092\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.235951\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.194352\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.406\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.35792\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.20369\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.17555\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH7\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.155808\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.123774\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.227746\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.273841\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC8\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.26451\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.33676\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.20365\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.08115\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH8\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.162911\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.120627\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.227727\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.157892\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eC9\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.2689\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.26207\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-0.32656\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.1275\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH9\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.162882\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.108327\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.235901\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.139896\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eOW1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.53454\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-0.46966\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH11\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.252062\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.188588\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eH12\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.326734\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.247576\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cb\u003eFMO analysis\u003c/b\u003e \u003c/p\u003e \u003cp\u003eIn order to comprehend the frontier effect of water and iodine, if present in benzimidazole derivatives, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) studies of the benzimidazole derivatives, (a) DBZ, (b) DBZW, (c) DBZI, and (d) DBZIW were conducted. HOMO-LUMO explains a variety of reactions in conjugated systems and is used to predict the most reactive location in π-electron systems using the frontier electron density. FMO analysis is commonly used to describe the optical and electrical properties of organic compounds. To understand the nature of the electronic transition, the electron density plots of HOMO and LUMO are presented in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e. The energy band gap value of HOMO and LUMO of DBZ, DBZW, DBZI and DBZIW have 4.997 eV, 4.786 eV, 3.309 eV and 1.265 eV, respectively. In molecular interactions, the HOMO stands for electron donors, and its energy is related to the ionization potential (IP), while the LUMO stands for electron acceptors, and its energy is related to the electron affinity (EA). The HOMO-LUMO energy gap, which is useful in determining the molecular electrical transport properties, explains the charge transfer interaction inside the molecule [\u003cspan additionalcitationids=\"CR33\" citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e]. Table\u0026nbsp;\u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e lists the predicted HOMO and LUMO energies as well as additional characteristics. Thus, it is clear from Table\u0026nbsp;\u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e that DBZ is hard, more stable and less reactive, while compound BDZIW is soft and the least stable and more reactive compare to others. The HOMO-LUMO energy gap decreases from molecule DBZ to DBZW to DBZI and the minimum energy gap is achieved with Water and I substituent in DBZ. Thus, this substituent increases the reactivity of the benzimidazole derivative.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab5\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eHOMO and LUMO energies and global reactivity descriptors calculated for DBZ, DBZW, DBZI and DBZIW\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"5\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eParameters\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eDBZ\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDBZW\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eDBZI\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eDBZWI\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eHOMO (eV)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-4.800\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-5.232\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-4.946\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-4.006\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eLUMO (eV)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.197\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-0.445\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-1.637\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-2.740\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eEnergy Gap (eV)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4.997\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4.786\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e3.309\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.265\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eIonization Potential\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4.800\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e5.232\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e4.946\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e4.006\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eElectron affinity\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.197\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.445\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.637\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e2.740\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eChemical Potential \u0026micro;\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2.301\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2.838\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e3.291\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3.373\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eElectron negativity χ\u0026nbsp;(eV)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-2.301\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-2.838\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-3.291\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-3.373\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eHardness η\u0026nbsp;(eV)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2.499\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2.393\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e1.655\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.633\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eSoftness (S)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e0.400\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e0.418\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e0.604\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.581\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eElectrophilicity index (ω)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e6.617\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e9.641\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e8.962\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3.599\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eMaximum electronic charge\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-0.921\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-1.186\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-1.989\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e-5.332\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eTotal Energy (A.U.)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-459.784\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-536.255\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e-470.413\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e0.116\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e\u003cb\u003eDipole moment (Debye)\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e2.303\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4.777\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003e9.037\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e21.894\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec14\" class=\"Section2\"\u003e \u003ch2\u003e3.4 Molecular docking study\u003c/h2\u003e \u003cp\u003eWe looked into a molecular docking study of 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ], 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW], 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI], and 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodide monohydrate [DBZIW] for further explore the role of water and I in the benzimidazole derivatives. The protein crystal structure for the thyroid stimulating hormone receptor (TSHR) was chosen (PDB ID 4QT5), and the Hex software was used to carry out the benzimidazole derivative inhibitor. We used the protein crystal structures as the protein targets, downloaded from the protein data bank. A docking calculation was performed to determine the docking score for benzimidazole derivatives with protein crystal structures separately with the HEX software [\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e]. The energy values obtained by the docking study are tabulated in Table\u0026nbsp;\u003cspan refid=\"Tab6\" class=\"InternalRef\"\u003e6\u003c/span\u003e and presented in Fig.\u0026nbsp;\u003cspan refid=\"Fig13\" class=\"InternalRef\"\u003e13\u003c/span\u003e. The best ligand structure, DBZIW (-191.91), fitted the receptors. Due to the presence of water and Iodine, DBZIW has more reactive compare to other molecular ligands. The docking score data, which also predicts the activity of the pharmacological molecule, indicates the binding energy necessary to form a bond between the ligand and receptor. The in vitro antibacterial activity of the synthesized DBZIW compound was evaluated using the dilution technique against bacterial strains and shown in figure S3 and tabulated in Table S3.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab6\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 6\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eThe energy values of DBZ, DBZW, DBZI, and DBZWI molecules obtained by the docking study\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"2\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCompound Name\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003e4QT5\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDBZ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-161.20\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDBZW\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-173.43\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDBZI\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-161.31\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eDBZWI\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e-191.91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003c/div\u003e"},{"header":"4. Conclusion","content":"\u003cp\u003eIn this work we described the crystal structure of 1, 3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] capable of forming H-bonds. DBZIW organized in weak π\u0026ndash;π stacked interaction involving the centroid of the five membered imidazole ring with six membered phenyl ring and simultaneously stabilized by chains of intermolecular O-H\u0026hellip;I dimer interactions with water molecule and iodine stacks in a fashion to form channel hold up by O-H\u0026hellip;I hydrogen bond interactions. The intermolecular hydrogen bonding interactions that contribute to the molecular stability were highlighted by the Hirshfeld surface analysis, and the 2D fingerprint map revealed the proportion of intermolecular contacts of the molecule, showing that H⋯H (51.1%) and I⋯H (27.5%) intermolecular interactions are the most prevalent in the crystal lattice. The energy framework study revealed the corresponding energies for the intermolecular interactions that were involved and it was found that the dispersion energy contributes maximum for each molecular pair for the stability of the structure. To support analysis of the molecular structure and role of the presence of I and water in the molecular structure [DBZIW], we optimized structures (DBZIW, DBZ, DBZI and DBZW) using DFT methods. The iodine atom has the largest negative charge in the entire molecule, according to an analysis of Mulliken charge distributions, which may have led to the occurrence of interactions involving particular atom of the molecule. HOMO-LUMO orbital analysis and the energy band gap demonstrated charge transfer inside the molecule, and computed lowest HOMO-LUMO band gap for the molecule DBZIW leads to intriguing electronic properties. Molecular docking analysis revealed better docking score of benzimidazole derivative (DBZWI) with 4qt5 protein crystal suggests more advantages for further pharmacological applications as specially for I molecule.\u003c/p\u003e"},{"header":"Declarations","content":"\u003ch2\u003eSupplementary Data\u003c/h2\u003e \u003cp\u003eCCDC 1508765 contains the supplementary crystallographic data for the compound. These data can be obtained free of charge via \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttp://www.ccdc.cam.ac.uk/conts/retrieving.html\u003c/span\u003e\u003cspan address=\"http://www.ccdc.cam.ac.uk/conts/retrieving.html\" targettype=\"URL\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e, or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,UK;fax: (+\u0026thinsp;44) 1223-336-033; or e-mail: [email protected]\u003c/p\u003e \u003ch2\u003eConflict of interest\u003c/h2\u003e \u003cp\u003eThe authors declare no conflict of interest.\u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eDr. Sahaj A Gandhi wrote the manuscript text mainly, corrected by Dr. U H Patel, supervisor. All the crystallography and DFT work carried out by Dr. Sahaj A. Gandhi. Dr. S. S. Soni and Dr. Deepli Kotadia were synthesized the compounds and characterized by H1 NMR and IR.\u003c/p\u003e\u003ch2\u003eAcknowledgements\u003c/h2\u003e \u003cp\u003eWe thankful to DST, New Delhi for supporting the FIST project at the Department of Physics, Sardar Patel University, Vallabh Vidyanagar, Gujarat, India, by providing the single-crystal X-ray diffractometer (Kappa Apex -II) equipment.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eNardi M, Cano NCH, Simeonov S, Bence R, Kurutos A, Scarpelli R, Wunderlin D (2023) Procopio Catalysts 13:392\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eKuş C, S\u0026ouml;z\u0026uuml;d\u0026ouml;nmez F, Can-Eke B, Coban T (2010) Z Naturforsch C J Biosci 65:537\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eBansal Y, Silakari O (2012) Bioorg Med Chem 20:6208\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAtes-Alagoz Z (2013) Curr Med Chem 20:4633\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAyhan-Kilcigil G, Kuş C, \u0026Ccedil;oban T, \u0026Ouml;zdamar ED, Can-Eke B (2014) Arch Pharm (Weinheim) 347:276\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eGł\u0026oacute;wka ML, Kałużyńska S, Krause M, Gobis K, Foks H, Szczesio M, Olczak A (2018) Acta Cryst C74:1684\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eMani GS, Anchi P, Sunkari S, Donthiboina K, Godugu C, Shankaraiah N, Kamal A (2020) Bioorg Med Chem Lett 30:127432\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eXiong JF, Li JX, Mo GZ, Huo JP, Liu JY, Chen XY, Wang ZY (2014) J Org Chem 79:11619\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCosby T, Holt A, Griffin PJ, Wang Y, Sangoro J (2015) J Phys Chem Lett 6:3961\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eCho H, Song J, Shin JW, Moon J, Kwon BH (2021) l. 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The asymmetric unit contains a molecule of [C9 H11N2]\u003csup\u003e+\u003c/sup\u003e, an iodine ion I\u003csup\u003e\u0026minus;\u003c/sup\u003e, and a water molecule.\u003c/p\u003e \u003cp\u003eWater oxygen O1 and iodine ion I\u003csup\u003e\u0026minus;\u003c/sup\u003e (O-H...I) connection display significant involvement in hydrogen bond interactions in the molecular packing of DBZIW. The network of C-H...O hydrogen bond contacts plays an essential part in the stability. The molecular structures 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ], 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW], 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI] and 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] were optimized at the B3LYP method with 6-311G (d, p) level using Gaussain-09 software. The energy band gap value of HOMO and LUMO of DBZ, DBZW, DBZI and DBZIW have 4.997 eV, 4.786 eV, 3.309 eV and 1.265 eV, respectively. The HOMO-LUMO energy gap, which is useful in determining the molecular electrical transport properties, explains the charge transfer interaction inside the molecule. The molecular docking studies indicated that DBZIW had high binding affinity for thyroid stimulating hormone receptor (TSHR) protein targets (4QT5).\u003c/p\u003e","manuscriptTitle":"The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-02-06 17:33:57","doi":"10.21203/rs.3.rs-3903688/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"3ce82b49-2eba-43ad-9cc0-97047c25a327","owner":[],"postedDate":"February 6th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2024-03-04T18:55:46+00:00","versionOfRecord":[],"versionCreatedAt":"2024-02-06 17:33:57","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-3903688","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-3903688","identity":"rs-3903688","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}