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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, C(18)H(20)ClN(4) (+)·C(7)H(3)N(2)O(6) (−)·C(2)H(6)OS, (I), where the dimethyl sulfoxid...

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Autores principales: Kaur, Manpreet, Jasinski, Jerry P., Yathirajan, Hemmige S., Kavitha, Channappa N., Glidewell, Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438793/
https://www.ncbi.nlm.nih.gov/pubmed/26029402
http://dx.doi.org/10.1107/S205698901500554X
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author Kaur, Manpreet
Jasinski, Jerry P.
Yathirajan, Hemmige S.
Kavitha, Channappa N.
Glidewell, Christopher
author_facet Kaur, Manpreet
Jasinski, Jerry P.
Yathirajan, Hemmige S.
Kavitha, Channappa N.
Glidewell, Christopher
author_sort Kaur, Manpreet
collection PubMed
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, C(18)H(20)ClN(4) (+)·C(7)H(3)N(2)O(6) (−)·C(2)H(6)OS, (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, C(18)H(20)ClN(4) (+)·C(4)H(3)O(4) (−)·0.21H(2)O, (II), and clozapinium 2-hy­droxy­benzoate, C(18)H(20)ClN(4) (+)·C(7)H(5)O(3) (−), (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.
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spelling pubmed-44387932015-05-30 The crystal structures of three clozapinium salts: different mol­ecular configurations, and supra­molecular assembly in one, two and three dimensions Kaur, Manpreet Jasinski, Jerry P. Yathirajan, Hemmige S. Kavitha, Channappa N. Glidewell, Christopher Acta Crystallogr E Crystallogr Commun Research Communications 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, C(18)H(20)ClN(4) (+)·C(7)H(3)N(2)O(6) (−)·C(2)H(6)OS, (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, C(18)H(20)ClN(4) (+)·C(4)H(3)O(4) (−)·0.21H(2)O, (II), and clozapinium 2-hy­droxy­benzoate, C(18)H(20)ClN(4) (+)·C(7)H(5)O(3) (−), (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. International Union of Crystallography 2015-03-25 /pmc/articles/PMC4438793/ /pubmed/26029402 http://dx.doi.org/10.1107/S205698901500554X Text en © Kaur et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Kaur, Manpreet
Jasinski, Jerry P.
Yathirajan, Hemmige S.
Kavitha, Channappa N.
Glidewell, Christopher
The crystal structures of three clozapinium salts: different mol­ecular configurations, and supra­molecular assembly in one, two and three dimensions
title 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_short 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438793/
https://www.ncbi.nlm.nih.gov/pubmed/26029402
http://dx.doi.org/10.1107/S205698901500554X
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