Molecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical calculations

Molecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical 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 Molecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical calculations Alexander V. Belyakov, Vladimir V. Kuznetsov, Nadezhda S. Kormil'tsyna, and 4 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7344972/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 15 Nov, 2025 Read the published version in Structural Chemistry → Version 1 posted 17 You are reading this latest preprint version Abstract The equilibrium molecular structure of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane (Cl-DABH) has been determined in gas-phase based on the data of electron diffraction (GED) method with the use of quantum chemical calculations up to the MP2/cc-pVTZ level of theory. A comparison is made for the main parameters of the molecule in the solid and gas phases. The change caused by the transition from one phase to another is shown. 6-(4-chlorophenyl)-1 5-diazabicyclo[3.1.0]hexane molecular structure conformational analysis GED quantum chemical simulations Figures Figure 1 Figure 2 Figure 3 Introduction Diaziridine derivatives exhibit various types of neurotropic activity[ 1 – 3 ]. The antidepressant and tranquilizing effects of 1-[2-(3,3-dimethyldiaziridin-1-yl)ethyl]-3,3-dimethyldiaziridine (Tetramezine), have been extensively studied [ 4 , 5 ]. A promising direction in modern medicinal chemistry is the creation of drugs with several pharmacologically active fragments combined together in one molecule [ 6 , 7 ]. A considerable improvement in the biological potential was observed when two or more pharmacophores were combined together in one molecule. A halogen-substituted phenyl group can be such a fragment. Structural analysis of these molecular systems will certainly be useful for predicting and interpreting their pharmacological activity. This study presents the first gas phase structural analysis of the molecule 6-(4-сhlorophenyl)-1,5-diazabicyclo[3.1.0]hexane, which contains diaziridine and 4-chlorophenyl fragments within a single molecule. Structural Analysis Geometry optimizations were performed at the second-order of the Møller–Plesset perturbation theory (MP2) [8] with cc-pVTZ [9] basis set, as well as at the density functional theory (DFT) level with the B3LYP functional [10–13] and cc-pVTZ basis set. These calculations were carried out using Gaussian16 (Revision C01) program package [14]. For the DFT simulations, normal coordinate analysis was used to determine the nature of the stationary points found on the potential energy surface and to calculate the thermodynamic functions of ensembles of different conformers under normal conditions. The resulting relative Gibbs energies were then used to estimate the conformer ratio according to the Boltzmann distribution at 298 K. It was found that the mole fraction of the boat conformation of C s symmetry shown in Fig.1 is no less than 98%. The amounts of the two additional conformations, exo- and endo -chair, are negligible[15]. The gas electron diffraction experiment (GED) is described in the Supplementary Materials, along with the experimental and theoretical data (Tables S2.1, S3.1, S3.2, S3.3). Mean vibrational amplitudes ( u ij ,h1 ) and vibrational corrections to the internuclear distances ( r ij, e – r ij, a ), which are required for the GED analysis, were computed using SHRINK program [16, 17] at the first-order perturbation theory level taking into account curvilinear kinematic effects, with the use of quadratic and cubic force fields. These force fields were calculated at the DFT level with the B3LYP functional and cc-pVTZ basis set. All the vibrational amplitudes and the respective corrections for the key conformer of Cl-DABH can be found in the Supplementary Materials (Table S3.3) To calculate the Cartesian coordinates of atoms, an algorithm given in Ref.19 was used. For the ring closure, the calculation of the coordinates is not terminated at the last atom in the ring but continued for the three dummy atoms according to the same rules [19]. The problem of the ring closure is reduced to the iterative solution of nonlinear equations with respect to the dependent geometrical parameters so that the Cartesian coordinates of dummy atoms coincide with those of the first three atoms of the ring. When refining structural parameters, the minimized functional has the form (1) where s = (4 π / λ ) sin( θ /2), θ is the scattering angle; λ is the electron beam wavelength w s is a weight function; s M( s ) is the molecular intensity function, and k is the scale factor. As a criterion of the functional minimum, the value of the R -factor was taken: (2) Least squares structure refinements were carried out with the use of a modified version of the KCED25 program [20]. Weight matrices were diagonal. The electron diffraction apparatus camera distance data (Table S2.1) were taken with the weights of 0.5 for the short camera distance and 1.0 for the long camera distance. The molecular geometry of Cl-DABH as shown in Fig. 1 was specified by 14 internuclear distances, 21 valence bond angles, and 7 dihedral angles of the molecule. Among them, 2 internuclear distances, 4 valence bond angles, and 2 dihedral angles were the ring closure parameters. Geometrical parameters and mean least-square vibrational amplitudes were refined in groups with constant differences from theoretical MP2 and DFT estimates, respectively. Particularly, the mean least-square amplitudes were refined in eleven groups according to the specific ranges of the radial distribution curve (Fig. 2 ): 1.0−1.2 Å; 1.1−2.0 Å; 2.0−2.6 Å; 2.6−3.2 Å; 3.2−3.5 Å; 3.5−4.3 Å; 4.3−4.8 Å; 4.8−5.4 Å; 5.4−6.2 Å; 6.2−7.6 Å; and 7.6−9.9 Å. The internuclear distances were refined in three groups, namely those of C–Cl internuclear distance, C-C in phenyl ring and all the residual except for C-H. Pairs of the equivalent valence angles A(7,1,2)/A(7,1,3) and A(2,3,4)/A(3,2,5), and dihedral angles D(1,2,3,4)/D(1,3,2,5) were refined. All the residual angles were set equal to the theoretical MP2 values. Small differences in similar geometrical parameters, like carbon-carbon bonds in phenyl ring, were set equal to MP2 theoretical values (Table 1). The final s M( s ) molecular intensity and f( r ) radial distribution functions are shown in Fig. 2. The correlation matrix between refined parameters can be found in Supplementary Materials (Table S3.4). The best correspondence between the experimental and calculated molecular intensities was obtained for the final set of geometrical parameters listed in Table 1. Table 1. Main equilibrium structural parameters of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane of C s symmetry Parameter GED a MP2/cc-pVTZ DFT/cc-pVTZ XRD Internuclear distances, r e /Å C(1)−N(2)/N(3) 1.454(15) 1.456 1.453 1.4582(19)/1.4558(19) N(2)−N(3) 1.505(15) 1.507 1.495 1.5167(19) N(3)−C(4)/C(5) 1.475(15) 1.477 1.478 1.488(3)/1.485(3) C(6)−C(4)/C(5) 1.529(15) 1.530 1.537 1.533(3)/1.531(3) C(1)−C(7) 1.474(15) 1.476 1.485 1.492(3) (C cycl −H) av 1.086 b 1.086 1.086 0.965(8) (C Ph −H) av 1.081 b 1.081 1.080 9.965(10) C(7)−C(8)/C(12) d 1.390(26) 1.397 1.395 1.390(3)/1.392(3) Cl(13)−C(10) 1.729(6) 1.735 1.754 1.7461(18) Bond angles/deg N(2)−N(3)−C(4)/ N(3)–N(2)–C(5) 106.9(1.2) 107.1 107.8 107.05(11)/107.06(12) C(7)−C(1)−H(14) 115.1 b 115.1 113.8 113.8(10) C(7)−C(1)−N(2)/N(3) 117.3(2.2) 117.6 118.8 117.36(13)/118.12(13) N(2)−C(5)−H(15)/ N(3)–C(4)–H(19) 108.9 b 108.9 109.4 106.1(13)/108.2(11) N(2)−C(5)−H(16)/ N(3)–C(4)–H(20) 106.5 b 106.5 106.7 108.0(14)/108.3(12) C(1)−C(7)−C(8) 120.1 b 120.1 120.9 120.97(14) C(1)−C(7)−C(12) 120.2 119.39(14) C(7)−C(8)−C(9) 120.2 b 120.4 120.6 120.82(15) C(7)−C(12)−C(11) 121.0 120.22(15) Dihedral angles/deg C(1)−N(2)−N(3)−C(4)/ C(1)−N(3)−N(2)−C(5) 105.9(2.0) 105.5 106.9 104.78(13)/105.37(13) C(5)−C(6)−C(4)−N(3)/ C(4)−C(6)−C(5)−N(2) 26.9 e 26.8 24.1 26.49(16)/26.80(17) H(14)−C(1)−C(7)−C(12)/C(8) 0.0 b 0.0 0.0 4.0(12)/-4.1(12) Total disagreement factor R f c (%) 4.5 a Errors are the standard deviations of the least square refinement: 3σ LS for bond lengths, bond angles and dihedral angles. b Fixed values. c R f is calculated with the use of Eqs. (1) and (2). d Carbon-carbon bond lengths of benzene ring are refined in one group with constant small differences from theoretical calculations. e Dependent ring closure parameter. Conclusion As shown in Table 1, the differences between GED, XRD, and theoretical geometrical parameters are insignificant, which is unusual. With the exception of the C–Cl bond length, all the residual parameters fall in the confidential ranges of the experimental values. According to GED data, the length of C–Cl bond in the gas phase is shorter than the predictions of quantum chemical calculations, while the solid-phase value (according to XRD data) falls in between. From the conformational point of view, it is the boat conformation that was found in both gas and solid phases, as follows from X-ray diffraction, GED, and QC calculations. QTAIM calculations carried out in order to find critical points have shown that the presence of an H…N hydrogen bond is unlikely (Figure 3). In the heteronuclear {1H-1H}gNOESY NMR correlation spectrum of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane (Fig. S7. ESM), a nuclear Overhauser effect (NOE) [21] is observed between the H(14) and H(17) protons of the 1,5-diazabicyclo[3.1.0]hexane cycle (Figure 1). This means that the molecule exists also in a boat conformation in a solution on a microsecond time scale of the NMR experiment. Two conformers (chair and boat) were also compared with the use of NBO analysis [22–24]. The results (Second order perturbation theory analysis of Fock matrix in NBO basis) shows that the total stabilization energy (E (2) ) due to all donor-acceptor interactions in the six-membered diazyridine cycle of the boat conformer is 154 kcal/mol, compared to 137 kcal/mol in the chair conformer. The total steric exchange energy in both conformers is the same, 323 cal/mol. The energy of hyperconjugation in the cycle promotes the stabilization of the boat conformation relative to the chair one. Thus, both experiments and theoretical consideration supports the nearly exclusive existence and stability of the boat conformer in all the phases. Declarations Author Contributions : Conceptualization, V.V.K., A.V.B; methodology, all authors; investigation, A.V.B.,N.S.K.,A.N.R.; resources, A.V.B., I.F.Sh. and K.L.T.; writing—original draft preparation, A.V.B. and I.F.Sh.; writing—review and editing, V.V.K., K.L.T. and I.F.Sh.; visualization, A.V.B. and A.S.D.; supervision, A.V.B, and I.F.Sh. All authors have read and agreed to the published version of the manuscript. Acknowledgments : The article was made as part of the work entitled “Molecular and supramolecular organization of compounds, hybrid and functional materials” (Number 121031300090-2). Ethics declaration: The research did not involve human participants and/or animals. Funding: There is no funding declaration. Institutional Review Board Statement : Not applicable. Informed Consent Statement : Not applicable. Data Availability Statement : Details of the gas-phase diffraction experiment are available as supplementary material. Conflicts of Interest : The authors declare no conflict of interest. References N.N. Makhova, V.Y. Petukhova, A.V. Shevtsov, V.V. Novakovskiy, V.V. Kuznetsov Agents for treating neurodegenerative disorders , US Pat., WO 2013/111117 A2, 2013. N.N. Makhova, V. Y. Petukhova, A. V. Shevtsov, V.V. Novakovskiy, V.V. Kuznetsov Agents for treating neurodegenerative disorders , US Pat., WO 2013/111118 A2, 2013. N. N. Makhova, V. Y. Petukhova, A. V. Shevtsov, V.V. Novakovskiy, V.V. Kuznetsov Agents for treating neurodegenerative disorders , US Pat., WO 2013.121334 A2, 2013. M. Kamuf, O. Trapp, Stereodynamics of tetramezine, Chirality , 23 (2011), pp. 113-117, https://doi.org/10.1002/chir.20885. L.S. Khaikin, I.V. Kochikov, A.N. Rykov, O.E. Grikina, G.G. Ageev, I.F. Shishkov, V.V. Kuznetsov, N.N. 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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-7344972","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":501858163,"identity":"b839363a-eb04-4b0b-9f6c-b1d9c0f10d94","order_by":0,"name":"Alexander V. Belyakov","email":"","orcid":"","institution":"Saint-Petersburg State Institute of Technology","correspondingAuthor":false,"prefix":"","firstName":"Alexander","middleName":"V.","lastName":"Belyakov","suffix":""},{"id":501858164,"identity":"37bf3076-7791-482a-baab-e0843c0f401d","order_by":1,"name":"Vladimir V. 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Atom numbering and coloring: (blue) nitrogen, (dark grey) carbon, (green) chlorine, and (light grey) hydrogen.\u003c/p\u003e","description":"","filename":"1.jpg","url":"https://assets-eu.researchsquare.com/files/rs-7344972/v1/b74d0147497cdcf729106476.jpg"},{"id":89690074,"identity":"361dd72f-9d39-43e9-9a6b-4f8a148d45dd","added_by":"auto","created_at":"2025-08-22 16:26:34","extension":"jpg","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":41487,"visible":true,"origin":"","legend":"\u003cp\u003e(left) Molecular intensity sM(s) functions and (right) Radial distribution f(\u003cem\u003er\u003c/em\u003e) functions of Cl-DABH. Experimental and calculated functions are shown with dotted and solid lines, respectively. The difference functions between the theory and experiment (Δ) were calculated by subtracting theoretical values from the experimental ones.\u003c/p\u003e","description":"","filename":"2.jpg","url":"https://assets-eu.researchsquare.com/files/rs-7344972/v1/8fd39bc063a34232b5b800ac.jpg"},{"id":89690075,"identity":"55c1aad5-eb11-4e7e-8410-90ee4cde5533","added_by":"auto","created_at":"2025-08-22 16:26:34","extension":"jpg","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":24391,"visible":true,"origin":"","legend":"\u003cp\u003eMolecular graph that shows critical points according to the B3LYP/cc-pVTZ level of theory\u003c/p\u003e","description":"","filename":"3.jpg","url":"https://assets-eu.researchsquare.com/files/rs-7344972/v1/a67b83f2197ff8de2b6c566f.jpg"},{"id":96105093,"identity":"7a8649c0-60a7-42da-8106-4a642e4c1494","added_by":"auto","created_at":"2025-11-17 16:08:33","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":624052,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-7344972/v1/c78c4b4b-da91-4fab-a731-837fd89b0492.pdf"},{"id":89690080,"identity":"1c9c7d71-147d-466a-8526-636ef096d965","added_by":"auto","created_at":"2025-08-22 16:26:34","extension":"docx","order_by":0,"title":"","display":"","copyAsset":false,"role":"supplement","size":666494,"visible":true,"origin":"","legend":"","description":"","filename":"SImanuscript.docx","url":"https://assets-eu.researchsquare.com/files/rs-7344972/v1/d366c4cbc0645791917c571b.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"\u003cp\u003e\u003cstrong\u003eMolecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical calculations\u003c/strong\u003e\u003c/p\u003e","fulltext":[{"header":"Introduction","content":"\u003cp\u003eDiaziridine derivatives exhibit various types of neurotropic activity[\u003cspan additionalcitationids=\"CR2\" citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e]. The antidepressant and tranquilizing effects of 1-[2-(3,3-dimethyldiaziridin-1-yl)ethyl]-3,3-dimethyldiaziridine (Tetramezine), have been extensively studied [\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e, \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e]. A promising direction in modern medicinal chemistry is the creation of drugs with several pharmacologically active fragments combined together in one molecule [\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e, \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e]. A considerable improvement in the biological potential was observed when two or more pharmacophores were combined together in one molecule. A halogen-substituted phenyl group can be such a fragment. Structural analysis of these molecular systems will certainly be useful for predicting and interpreting their pharmacological activity. This study presents the first gas phase structural analysis of the molecule 6-(4-сhlorophenyl)-1,5-diazabicyclo[3.1.0]hexane, which contains diaziridine and 4-chlorophenyl fragments within a single molecule.\u003c/p\u003e"},{"header":"Structural Analysis","content":"\u003cp\u003eGeometry optimizations were performed at the second-order of the M\u0026oslash;ller\u0026ndash;Plesset perturbation theory (MP2) [8] with cc-pVTZ [9] basis set, as well as at the density functional theory (DFT) level with the B3LYP functional [10\u0026ndash;13] and cc-pVTZ basis set. These calculations were carried out using Gaussian16 (Revision C01) program package [14]. For the DFT simulations, normal coordinate analysis was used to determine the nature of the stationary points found on the potential energy surface and to calculate the thermodynamic functions of ensembles of different conformers under normal conditions. The resulting relative Gibbs energies were then used to estimate the conformer ratio according to the Boltzmann distribution at 298 K. It was found that the mole fraction of the boat conformation of \u003cem\u003eC\u003c/em\u003e\u003csub\u003es\u0026nbsp;\u003c/sub\u003esymmetry shown in Fig.1 is no less than 98%. The amounts of the two additional conformations, \u003cem\u003eexo-\u003c/em\u003e and \u003cem\u003eendo\u003c/em\u003e-chair, are negligible[15]. The gas electron diffraction experiment (GED) is described in the Supplementary Materials, along with the experimental and theoretical data \u0026nbsp; (Tables S2.1, S3.1, S3.2, S3.3).\u003c/p\u003e\n\u003cp\u003eMean vibrational amplitudes (\u003cem\u003eu\u003csub\u003eij\u003c/sub\u003e\u003c/em\u003e\u003csub\u003e,h1\u003c/sub\u003e) and vibrational corrections to the internuclear distances (\u003cem\u003er\u003csub\u003eij,\u003c/sub\u003e\u003c/em\u003e\u003csub\u003ee\u003c/sub\u003e \u0026ndash; \u003cem\u003er\u003csub\u003eij,\u003c/sub\u003e\u003c/em\u003e\u003csub\u003ea\u003c/sub\u003e), which are required for the GED analysis, were computed using SHRINK program [16, 17]\u003csup\u003e\u0026nbsp;\u003c/sup\u003eat the first-order perturbation theory level taking into account curvilinear kinematic effects, with the use of quadratic and cubic force fields. These force fields were calculated at the DFT level with the B3LYP functional and cc-pVTZ basis set. All the vibrational amplitudes and the respective corrections for the key conformer of Cl-DABH can be found in the Supplementary Materials (Table S3.3)\u003c/p\u003e\n\u003cp\u003eTo calculate the Cartesian coordinates of atoms, an algorithm given in Ref.19 was used. For the ring closure, the calculation of the coordinates is not terminated at the last atom in the ring but continued for the three dummy atoms according to the same rules [19]. The problem of the ring closure is reduced to the iterative solution of nonlinear equations with respect to the dependent geometrical parameters so that the Cartesian coordinates of dummy atoms coincide with those of the first three atoms of the ring.\u003c/p\u003e\n\u003cp\u003eWhen refining structural parameters, the minimized functional has the form\u003c/p\u003e\n\u003cp\u003e\u003cimg width=\"293\" height=\"21\" 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\" alt=\"image\"\u003e\u0026nbsp;(1)\u003c/p\u003e\n\u003cp\u003ewhere \u003cem\u003es\u003c/em\u003e = (4\u003cem\u003e\u0026pi;\u003c/em\u003e/\u003cem\u003e\u0026lambda;\u003c/em\u003e) sin(\u003cem\u003e\u0026theta;\u003c/em\u003e/2), \u003cem\u003e\u0026theta;\u0026nbsp;\u003c/em\u003eis the scattering angle; \u003cem\u003e\u0026lambda;\u003c/em\u003e is the electron beam wavelength \u003cem\u003ew\u003c/em\u003e\u003csub\u003es\u003c/sub\u003e is a weight function; \u003cem\u003es\u003c/em\u003eM(\u003cem\u003es\u003c/em\u003e) is the molecular intensity function, and \u003cem\u003ek\u003c/em\u003e is the scale factor. As a criterion of the functional \u0026nbsp;minimum, the value of the \u003cem\u003eR\u003c/em\u003e-factor was taken:\u003c/p\u003e\n\u003cp\u003e\u003cimg width=\"157\" height=\"59\" 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\" alt=\"image\"\u003e\u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;(2)\u003c/p\u003e\n\u003cp\u003eLeast squares structure refinements were carried out with the use of a modified version of the KCED25 program [20]. Weight matrices were diagonal. The electron diffraction apparatus camera distance data (Table S2.1) were taken with the weights of 0.5 for the short camera distance and 1.0 for the long camera distance.\u003c/p\u003e\n\u003cp\u003eThe molecular geometry of Cl-DABH\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003eas shown in Fig. 1 was specified by 14 internuclear distances, 21 valence bond angles, and 7 dihedral angles of the molecule. Among them, 2 internuclear distances, 4 valence bond angles, and 2 dihedral angles were the ring closure parameters. Geometrical parameters and mean least-square vibrational amplitudes were refined in groups with constant differences from theoretical MP2 and DFT estimates, respectively. Particularly, the mean least-square amplitudes were refined in eleven groups according to the specific ranges of the radial distribution curve (Fig. 2 ): 1.0\u0026minus;1.2 \u0026Aring;; 1.1\u0026minus;2.0 \u0026Aring;; 2.0\u0026minus;2.6 \u0026Aring;; 2.6\u0026minus;3.2 \u0026Aring;; 3.2\u0026minus;3.5 \u0026Aring;; 3.5\u0026minus;4.3 \u0026Aring;; 4.3\u0026minus;4.8 \u0026Aring;; 4.8\u0026minus;5.4 \u0026Aring;; 5.4\u0026minus;6.2 \u0026Aring;; 6.2\u0026minus;7.6 \u0026Aring;; and 7.6\u0026minus;9.9 \u0026Aring;. The internuclear distances were refined in three groups, namely those of C\u0026ndash;Cl internuclear distance, C-C in phenyl ring and all the residual except for C-H. Pairs of the equivalent valence angles A(7,1,2)/A(7,1,3) and A(2,3,4)/A(3,2,5), and dihedral angles D(1,2,3,4)/D(1,3,2,5) were refined. All the residual angles were set equal to the theoretical MP2 values. Small differences in similar geometrical parameters, like carbon-carbon bonds in phenyl ring, were set equal to MP2 theoretical values (Table 1). The final \u003cem\u003es\u003c/em\u003eM(\u003cem\u003es\u003c/em\u003e) molecular intensity and f(\u003cem\u003er\u003c/em\u003e) radial distribution functions are shown in Fig. 2. The correlation matrix between refined parameters can be found in Supplementary Materials (Table S3.4).\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eThe best correspondence between the experimental and calculated molecular intensities was obtained for the final set of geometrical parameters listed in Table 1.\u003c/p\u003e\n\u003cp\u003eTable 1. Main equilibrium structural parameters of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane of \u003cem\u003eC\u003c/em\u003e\u003csub\u003es\u003c/sub\u003e symmetry\u003c/p\u003e\n \u003ctable border=\"0\" cellspacing=\"0\" cellpadding=\"0\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd rowspan=\"2\" style=\"width: 184px;\"\u003e\n \u003cp\u003eParameter\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003eGED\u003cem\u003e\u003csup\u003ea\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003eMP2/cc-pVTZ\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003eDFT/cc-pVTZ\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003eXRD\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"4\" style=\"width: 445px;\"\u003e\n \u003cp\u003e\u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp; \u0026nbsp;\u0026nbsp;Internuclear distances, \u003cem\u003er\u003c/em\u003e\u003csub\u003ee\u003c/sub\u003e/\u0026Aring;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(1)\u0026minus;N(2)/N(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.454(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.456\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.453\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.4582(19)/1.4558(19)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eN(2)\u0026minus;N(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.505(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.507\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.495\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.5167(19)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eN(3)\u0026minus;C(4)/C(5)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.475(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.477\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.478\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.488(3)/1.485(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(6)\u0026minus;C(4)/C(5)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.529(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.530\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.537\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.533(3)/1.531(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(1)\u0026minus;C(7)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.474(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.476\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.485\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.492(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003e(C\u003csub\u003ecycl\u003c/sub\u003e\u0026minus;H)\u003csub\u003eav\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.086 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.086\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.086\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e0.965(8)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003e(C\u003csub\u003ePh\u003c/sub\u003e\u0026minus;H)\u003csub\u003eav\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.081 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.081\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.080\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e9.965(10)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(7)\u0026minus;C(8)/C(12) \u003cem\u003e\u003csup\u003ed\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.390(26)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.397\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.395\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.390(3)/1.392(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eCl(13)\u0026minus;C(10)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e1.729(6)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e1.735\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e1.754\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e1.7461(18)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"5\" style=\"width: 629px;\"\u003e\n \u003cp\u003eBond angles/deg\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eN(2)\u0026minus;N(3)\u0026minus;C(4)/\u003c/p\u003e\n \u003cp\u003eN(3)\u0026ndash;N(2)\u0026ndash;C(5)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e106.9(1.2)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e107.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e107.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e107.05(11)/107.06(12)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(7)\u0026minus;C(1)\u0026minus;H(14)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e115.1 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e115.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e113.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e113.8(10)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(7)\u0026minus;C(1)\u0026minus;N(2)/N(3)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e117.3(2.2)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e117.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e118.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e117.36(13)/118.12(13)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eN(2)\u0026minus;C(5)\u0026minus;H(15)/\u003c/p\u003e\n \u003cp\u003eN(3)\u0026ndash;C(4)\u0026ndash;H(19)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e108.9\u0026nbsp;\u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e108.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e109.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e106.1(13)/108.2(11)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eN(2)\u0026minus;C(5)\u0026minus;H(16)/\u003c/p\u003e\n \u003cp\u003eN(3)\u0026ndash;C(4)\u0026ndash;H(20)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e106.5 \u003cstrong\u003e\u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/strong\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e106.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e106.7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e108.0(14)/108.3(12)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(1)\u0026minus;C(7)\u0026minus;C(8)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e120.1 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e120.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e120.9\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e120.97(14)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(1)\u0026minus;C(7)\u0026minus;C(12)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e120.2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e119.39(14)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(7)\u0026minus;C(8)\u0026minus;C(9)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e120.2 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e120.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e120.6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e120.82(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(7)\u0026minus;C(12)\u0026minus;C(11)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e121.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e120.22(15)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"5\" style=\"width: 629px;\"\u003e\n \u003cp\u003eDihedral angles/deg\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(1)\u0026minus;N(2)\u0026minus;N(3)\u0026minus;C(4)/\u003c/p\u003e\n \u003cp\u003eC(1)\u0026minus;N(3)\u0026minus;N(2)\u0026minus;C(5)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e105.9(2.0)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e105.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e106.9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e104.78(13)/105.37(13)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eC(5)\u0026minus;C(6)\u0026minus;C(4)\u0026minus;N(3)/\u003c/p\u003e\n \u003cp\u003eC(4)\u0026minus;C(6)\u0026minus;C(5)\u0026minus;N(2)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e26.9 \u003cem\u003e\u003csup\u003ee\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e26.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e24.1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e26.49(16)/26.80(17)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd style=\"width: 184px;\"\u003e\n \u003cp\u003eH(14)\u0026minus;C(1)\u0026minus;C(7)\u0026minus;C(12)/C(8)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 88px;\"\u003e\n \u003cp\u003e0.0 \u003cem\u003e\u003csup\u003eb\u003c/sup\u003e\u003c/em\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 106px;\"\u003e\n \u003cp\u003e0.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 110px;\"\u003e\n \u003cp\u003e0.0\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e4.0(12)/-4.1(12)\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"4\" style=\"width: 488px;\"\u003e\n \u003cp\u003eTotal disagreement factor \u003cem\u003eR\u003c/em\u003e\u003csub\u003ef\u003c/sub\u003e \u003cem\u003e\u003csup\u003ec\u003c/sup\u003e\u003c/em\u003e (%) \u0026nbsp; \u0026nbsp; 4.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd style=\"width: 142px;\"\u003e\n \u003cp\u003e\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003e\u003cem\u003e\u003csup\u003ea\u0026nbsp;\u003c/sup\u003e\u003c/em\u003eErrors are the standard deviations of the least square refinement: 3\u0026sigma;\u003csub\u003eLS\u003c/sub\u003e for bond lengths, bond angles and dihedral angles. \u003cem\u003e\u003csup\u003eb\u0026nbsp;\u003c/sup\u003e\u003c/em\u003eFixed values. \u003cem\u003e\u003csup\u003ec\u003c/sup\u003e\u003c/em\u003e \u003cem\u003eR\u003c/em\u003e\u003csub\u003ef\u003c/sub\u003e is calculated with the use of Eqs. (1) and (2). \u003cem\u003e\u003csup\u003ed\u003c/sup\u003e\u003c/em\u003e Carbon-carbon bond lengths of benzene ring are refined in one group with constant small differences from theoretical calculations.\u0026nbsp;\u003cem\u003e\u003csup\u003ee\u003c/sup\u003e\u003c/em\u003e Dependent ring closure parameter.\u003c/p\u003e"},{"header":"Conclusion","content":"\u003cp\u003eAs shown in Table 1, the differences between GED, XRD, and theoretical geometrical parameters are insignificant, which is unusual. With the exception of the C–Cl bond length, all the residual parameters fall in the confidential ranges of the experimental values. According to GED data, the length of C–Cl bond in the gas phase is shorter than the predictions of quantum chemical calculations, while the solid-phase value (according to XRD data) falls in between.\u003c/p\u003e\n\u003cp\u003eFrom the conformational point of view, it is the boat conformation that was found in both gas and solid phases, as follows from X-ray diffraction, GED, and QC calculations. QTAIM calculations carried out in order to find critical points have shown that the presence of an H…N hydrogen bond is unlikely (Figure 3). In the heteronuclear {1H-1H}gNOESY NMR correlation spectrum of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane (Fig. S7. ESM), a nuclear Overhauser effect (NOE) [21] is observed between the H(14) and H(17) protons of the 1,5-diazabicyclo[3.1.0]hexane cycle (Figure 1). This means that the molecule exists also in a boat conformation in a solution on a microsecond time scale of the NMR experiment.\u003c/p\u003e\n\u003cp\u003eTwo conformers (chair and boat) were also compared with the use of NBO analysis [22–24].\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eThe results (Second order perturbation theory analysis of Fock matrix in NBO\u0026nbsp; basis) shows that the total stabilization energy (E\u003csup\u003e(2)\u003c/sup\u003e) due to all donor-acceptor interactions in the six-membered diazyridine cycle of the boat conformer is 154 kcal/mol, compared to 137 kcal/mol in the chair conformer. The total steric exchange energy in both conformers is the same, 323 cal/mol. The energy of hyperconjugation in the cycle promotes the stabilization of the boat conformation relative to the chair one.\u003c/p\u003e\n\u003cp\u003eThus, both experiments and theoretical consideration supports the nearly exclusive existence and stability of the boat conformer in all the phases.\u0026nbsp;\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAuthor Contributions\u003c/strong\u003e: Conceptualization, V.V.K., A.V.B; methodology, all authors; investigation, A.V.B.,N.S.K.,A.N.R.; resources, A.V.B., I.F.Sh. and K.L.T.; writing\u0026mdash;original draft preparation, A.V.B. and I.F.Sh.; writing\u0026mdash;review and editing, V.V.K., K.L.T. and I.F.Sh.; visualization, A.V.B. and A.S.D.; supervision, A.V.B, and I.F.Sh. All authors have read and agreed to the published version of the manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgments\u003c/strong\u003e: The article was made as part of the work entitled \u0026ldquo;Molecular and supramolecular organization of compounds, hybrid and functional materials\u0026rdquo; (Number 121031300090-2).\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eEthics declaration:\u003c/strong\u003e The research did not involve human participants and/or animals.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding:\u003c/strong\u003e There is no funding declaration.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eInstitutional Review Board Statement\u003c/strong\u003e: Not applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eInformed Consent Statement\u003c/strong\u003e: Not applicable.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData Availability Statement\u003c/strong\u003e: Details of the gas-phase diffraction experiment are available as supplementary material.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of Interest\u003c/strong\u003e: The authors declare no conflict of interest.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eN.N. 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Strand and R. Stolevik, \u003cem\u003eActa Chem. Scand.\u003c/em\u003e, 1969, https://doi.org/10.3891/acta.chem.scand.23-3224, 3224-3228.\u003c/li\u003e\n\u003cli\u003eV.V. Kuznetsov, D.V. Khakimov, A.S. Dmitrenok , A.S. Goloveshkin, \u0026laquo;Synthesis, structure and peculiarity of conformational behavior of 1,5-diazabicyclo[3.1.0]hexanes\u0026raquo;, \u003cem\u003eJournal of Molecular Structure\u003c/em\u003e, Vol 1269, 5 December, 2022, 133856.\u003c/li\u003e\n\u003cli\u003eWeinhold, F.; Landis, C.R. Discovering Chemistry With Natural Bond Orbitals.- Upper Saddle River, NJ: John Wiley \u0026amp; Sons, 2012, 300.\u003c/li\u003e\n\u003cli\u003eWeinhold, F.; Landis, C.R. Valency and Bonding. A Natural Bond Orbital Donor-Acceptor Perspective.- Cambridge, UK; New York: Cambridge Univ. Press, 2005, 760.\u003c/li\u003e\n\u003cli\u003eGlendening, E.D.; Landis, C.R.; Weinhold, F. NBO 7.0: New vistas in localized and delocalized chemical bonding theory. J. Comput. Chem. 2019, 40(25), 2234\u0026ndash;2241.\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane, molecular structure, conformational analysis, GED, quantum chemical simulations","lastPublishedDoi":"10.21203/rs.3.rs-7344972/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7344972/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThe equilibrium molecular structure of 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane (Cl-DABH) has been determined in gas-phase based on the data of electron diffraction (GED) method with the use of quantum chemical calculations up to the MP2/cc-pVTZ level of theory.\u003c/p\u003e\n\u003cp\u003eA comparison is made for the main parameters of the molecule in the solid and gas phases. The change caused by the transition from one phase to another is shown.\u003c/p\u003e","manuscriptTitle":"Molecular structure of gaseous 6-(4-chlorophenyl)-1,5-diazabicyclo[3.1.0]hexane studied by electron diffraction and quantum-chemical calculations","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-08-22 16:26:29","doi":"10.21203/rs.3.rs-7344972/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2025-09-07T05:48:44+00:00","index":"","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-09-07T04:00:02+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-31T16:01:07+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-27T07:32:26+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-26T11:03:17+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-22T19:16:04+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2025-08-18T09:40:12+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"137349643965775949397256701346389027585","date":"2025-08-17T19:33:54+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"100919576708714935309637909931849783388","date":"2025-08-17T11:59:31+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"316895123115606174909293314466886384532","date":"2025-08-16T15:28:30+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"159039578294024379220741851448759189123","date":"2025-08-15T15:48:02+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"255009588304886698966035890744952228150","date":"2025-08-15T14:02:21+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"91524194556013133642225502318903707904","date":"2025-08-15T11:04:18+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-08-15T10:50:48+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-08-14T12:55:13+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2025-08-14T06:33:05+00:00","index":"","fulltext":""},{"type":"submitted","content":"Structural Chemistry","date":"2025-08-11T09:47:06+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"structural-chemistry","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"stuc","sideBox":"Learn more about [Structural Chemistry](https://www.springer.com/journal/11224)","snPcode":"11224","submissionUrl":"https://submission.nature.com/new-submission/11224/3","title":"Structural Chemistry","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"125288e2-60b5-4590-a828-a26e57d78d58","owner":[],"postedDate":"August 22nd, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-11-17T16:02:53+00:00","versionOfRecord":{"articleIdentity":"rs-7344972","link":"https://doi.org/10.1007/s11224-025-02649-6","journal":{"identity":"structural-chemistry","isVorOnly":false,"title":"Structural Chemistry"},"publishedOn":"2025-11-15 15:58:15","publishedOnDateReadable":"November 15th, 2025"},"versionCreatedAt":"2025-08-22 16:26:29","video":"","vorDoi":"10.1007/s11224-025-02649-6","vorDoiUrl":"https://doi.org/10.1007/s11224-025-02649-6","workflowStages":[]},"version":"v1","identity":"rs-7344972","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7344972","identity":"rs-7344972","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}