The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions
The structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+·C7H3N2O6−·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over...
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doaj-ca57cd5d075945f587c9d7bd231f76412020-11-24T23:46:14ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-04-0171440641310.1107/S205698901500554Xhb7383The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensionsManpreet Kaur0Jerry P. Jasinski1Hemmige S. Yathirajan2Channappa N. Kavitha3Christopher Glidewell4Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, IndiaDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USADepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, IndiaSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, ScotlandThe structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+·C7H3N2O6−·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clozapinium hydrogen maleate 0.21-hydrate, C18H20ClN4+·C4H3O4−·0.21H2O, (II), and clozapinium 2-hydroxybenzoate, C18H20ClN4+·C7H5O3−, (III). In all three salts, the protonation site is the methylated N atom of the piperazine ring, and the dimensions and conformations of the fused tricyclic system are very similar. However, differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry. In compound (III), both N-substituents in this ring occupy equatorial sites, but in compound (II) the fused tricyclic system occupies an axial site of the piperazine ring. The independent components of compound (I) are linked within the selected asymmetric unit by a combination of N—H...O and C—H...O hydrogen bonds, and these hydrogen-bonded aggregates are linked into chains by an aromatic π–π stacking interaction. In compound (II), the components are linked into sheets by a combination of O—H...O, N—H...O and C—H...O hydrogen bonds, and in compound (III), a combination of N—H...O, C—H...O and C—H...N hydrogen bonds links the components into a three-dimensional framework structure. Comparisons are made with some similar compounds.http://scripts.iucr.org/cgi-bin/paper?S205698901500554Xcrystal structureclozapiniumcrystal structuremolecular configurationhydrogen bondingsupramolecular assembly |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Manpreet Kaur Jerry P. Jasinski Hemmige S. Yathirajan Channappa N. Kavitha Christopher Glidewell |
spellingShingle |
Manpreet Kaur Jerry P. Jasinski Hemmige S. Yathirajan Channappa N. Kavitha Christopher Glidewell The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions Acta Crystallographica Section E: Crystallographic Communications crystal structure clozapinium crystal structure molecular configuration hydrogen bonding supramolecular assembly |
author_facet |
Manpreet Kaur Jerry P. Jasinski Hemmige S. Yathirajan Channappa N. Kavitha Christopher Glidewell |
author_sort |
Manpreet Kaur |
title |
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
title_short |
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
title_full |
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
title_fullStr |
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
title_full_unstemmed |
The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
title_sort |
crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2015-04-01 |
description |
The structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+·C7H3N2O6−·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clozapinium hydrogen maleate 0.21-hydrate, C18H20ClN4+·C4H3O4−·0.21H2O, (II), and clozapinium 2-hydroxybenzoate, C18H20ClN4+·C7H5O3−, (III). In all three salts, the protonation site is the methylated N atom of the piperazine ring, and the dimensions and conformations of the fused tricyclic system are very similar. However, differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry. In compound (III), both N-substituents in this ring occupy equatorial sites, but in compound (II) the fused tricyclic system occupies an axial site of the piperazine ring. The independent components of compound (I) are linked within the selected asymmetric unit by a combination of N—H...O and C—H...O hydrogen bonds, and these hydrogen-bonded aggregates are linked into chains by an aromatic π–π stacking interaction. In compound (II), the components are linked into sheets by a combination of O—H...O, N—H...O and C—H...O hydrogen bonds, and in compound (III), a combination of N—H...O, C—H...O and C—H...N hydrogen bonds links the components into a three-dimensional framework structure. Comparisons are made with some similar compounds. |
topic |
crystal structure clozapinium crystal structure molecular configuration hydrogen bonding supramolecular assembly |
url |
http://scripts.iucr.org/cgi-bin/paper?S205698901500554X |
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