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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,...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2016
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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. |
format | Online Article Text |
id | pubmed-4908520 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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