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Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data

The asymmetric unit of the title compound, C(16)H(17)ClNO(2)S(+)·HSO(4) (−), (I) [systematic name: (+)-(S)-5-[(2-chloro­phen­yl)(meth­oxy­carbon­yl)meth­yl]-4,5,6,7-tetra­hydro­thieno[3,2-c]pyridin-5-ium hydrogen sulfate], contains two independent cations of clopidogrel and two independent hydrogens...

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Autores principales: Chernyshev, Vladimir V., Pirogov, Sergey V., Shishkina, Irina N., Velikodny, Yurii A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007342/
https://www.ncbi.nlm.nih.gov/pubmed/21588394
http://dx.doi.org/10.1107/S1600536810028783
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author Chernyshev, Vladimir V.
Pirogov, Sergey V.
Shishkina, Irina N.
Velikodny, Yurii A.
author_facet Chernyshev, Vladimir V.
Pirogov, Sergey V.
Shishkina, Irina N.
Velikodny, Yurii A.
author_sort Chernyshev, Vladimir V.
collection PubMed
description The asymmetric unit of the title compound, C(16)H(17)ClNO(2)S(+)·HSO(4) (−), (I) [systematic name: (+)-(S)-5-[(2-chloro­phen­yl)(meth­oxy­carbon­yl)meth­yl]-4,5,6,7-tetra­hydro­thieno[3,2-c]pyridin-5-ium hydrogen sulfate], contains two independent cations of clopidogrel and two independent hydrogensulfate anions. The two independent cations are of similar conformation; however, this differs from that observed in ortho­rhom­bic form (II) [Bousquet et al. (2003 ▶). US Patent No. 6 504 030]. The H—N—C(chiral)—H fragment shows a trans conformation in both independent cations in (I) and a gauche conformation in (II). In (I), classical inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link two independent cations and two independent anions into an isolated cluster, in which two cations inter­act with one anion only via N—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯O hydrogen bonds further consolidate the crystal packing.
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spelling pubmed-30073422010-12-30 Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data Chernyshev, Vladimir V. Pirogov, Sergey V. Shishkina, Irina N. Velikodny, Yurii A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The asymmetric unit of the title compound, C(16)H(17)ClNO(2)S(+)·HSO(4) (−), (I) [systematic name: (+)-(S)-5-[(2-chloro­phen­yl)(meth­oxy­carbon­yl)meth­yl]-4,5,6,7-tetra­hydro­thieno[3,2-c]pyridin-5-ium hydrogen sulfate], contains two independent cations of clopidogrel and two independent hydrogensulfate anions. The two independent cations are of similar conformation; however, this differs from that observed in ortho­rhom­bic form (II) [Bousquet et al. (2003 ▶). US Patent No. 6 504 030]. The H—N—C(chiral)—H fragment shows a trans conformation in both independent cations in (I) and a gauche conformation in (II). In (I), classical inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link two independent cations and two independent anions into an isolated cluster, in which two cations inter­act with one anion only via N—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯O hydrogen bonds further consolidate the crystal packing. International Union of Crystallography 2010-07-24 /pmc/articles/PMC3007342/ /pubmed/21588394 http://dx.doi.org/10.1107/S1600536810028783 Text en © Chernyshev et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Chernyshev, Vladimir V.
Pirogov, Sergey V.
Shishkina, Irina N.
Velikodny, Yurii A.
Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title_full Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title_fullStr Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title_full_unstemmed Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title_short Monoclinic form I of clopidogrel hydrogen sulfate from powder diffraction data
title_sort monoclinic form i of clopidogrel hydrogen sulfate from powder diffraction data
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007342/
https://www.ncbi.nlm.nih.gov/pubmed/21588394
http://dx.doi.org/10.1107/S1600536810028783
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