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Crystal structure of canagliflozin hemihydrate

There are two canagliflozin mol­ecules (A and B) and one water mol­ecule in the asymmetric unit of the title compound, C(24)H(25)FO(5)S·0.5H(2)O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluoro­phen­yl)thio­phen-2-yl]meth­yl}-4-methylphen­yl)-6-(hy­droxy­meth­yl)-3,4,5,6-tetra­hydro-2H-pyran-3,...

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Autores principales: Liu, Kai-Hang, Gu, Jian-Ming, Hu, Xiu-Rong, Tang, Gu-Ping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908520/
https://www.ncbi.nlm.nih.gov/pubmed/27308030
http://dx.doi.org/10.1107/S2056989016006769
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author Liu, Kai-Hang
Gu, Jian-Ming
Hu, Xiu-Rong
Tang, Gu-Ping
author_facet Liu, Kai-Hang
Gu, Jian-Ming
Hu, Xiu-Rong
Tang, Gu-Ping
author_sort Liu, Kai-Hang
collection PubMed
description There are two canagliflozin mol­ecules (A and B) and one water mol­ecule in the asymmetric unit of the title compound, C(24)H(25)FO(5)S·0.5H(2)O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluoro­phen­yl)thio­phen-2-yl]meth­yl}-4-methylphen­yl)-6-(hy­droxy­meth­yl)-3,4,5,6-tetra­hydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methyl­benzene and thio­phene rings are 115.7 (4) and 111.7 (4)°, while the dihedral angles between the fluoro­benzene and thio­phene rings are 24.2 (6) and 20.5 (9)° in mol­ecules A and B, respectively. The hydro­pyran ring exhibits a chair conformation in both canagliflozin mol­ecules. In the crystal, the canagliflozin mol­ecules and lattice water mol­ecules are connected via O—H⋯O hydrogen bonds into a three-dimensional supra­molecular architecture.
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spelling pubmed-49085202016-06-15 Crystal structure of canagliflozin hemihydrate Liu, Kai-Hang Gu, Jian-Ming Hu, Xiu-Rong Tang, Gu-Ping Acta Crystallogr E Crystallogr Commun Research Communications There are two canagliflozin mol­ecules (A and B) and one water mol­ecule in the asymmetric unit of the title compound, C(24)H(25)FO(5)S·0.5H(2)O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluoro­phen­yl)thio­phen-2-yl]meth­yl}-4-methylphen­yl)-6-(hy­droxy­meth­yl)-3,4,5,6-tetra­hydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methyl­benzene and thio­phene rings are 115.7 (4) and 111.7 (4)°, while the dihedral angles between the fluoro­benzene and thio­phene rings are 24.2 (6) and 20.5 (9)° in mol­ecules A and B, respectively. The hydro­pyran ring exhibits a chair conformation in both canagliflozin mol­ecules. In the crystal, the canagliflozin mol­ecules and lattice water mol­ecules are connected via O—H⋯O hydrogen bonds into a three-dimensional supra­molecular architecture. International Union of Crystallography 2016-04-26 /pmc/articles/PMC4908520/ /pubmed/27308030 http://dx.doi.org/10.1107/S2056989016006769 Text en © Liu et al. 2016 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 Research Communications
Liu, Kai-Hang
Gu, Jian-Ming
Hu, Xiu-Rong
Tang, Gu-Ping
Crystal structure of canagliflozin hemihydrate
title Crystal structure of canagliflozin hemihydrate
title_full Crystal structure of canagliflozin hemihydrate
title_fullStr Crystal structure of canagliflozin hemihydrate
title_full_unstemmed Crystal structure of canagliflozin hemihydrate
title_short Crystal structure of canagliflozin hemihydrate
title_sort crystal structure of canagliflozin hemihydrate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4908520/
https://www.ncbi.nlm.nih.gov/pubmed/27308030
http://dx.doi.org/10.1107/S2056989016006769
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