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Crystal structure of canagliflozin hemihydrate.

ABSTRACT: There are two canagliflozin mol-ecules (A and B) and one water mol-ecule in the asymmetric unit of the title compound, C24H25FO5S·0.5H2O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluoro-phen-yl)thio-phen-2-yl]meth-yl}-4-methylphen-yl)-6-(hy-droxy-meth-yl)-3,4,5,6-tetra-hydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methyl-benzene and thio-phene rings are 115.7?(4) and 111.7?(4)°, while the dihedral angles between the fluoro-benzene and thio-phene rings are 24.2?(6) and 20.5?(9)° in mol-ecules A and B, respectively. The hydro-pyran ring exhibits a chair conformation in both canagliflozin mol-ecules. In the crystal, the canagliflozin mol-ecules and lattice water mol-ecules are connected via O-H?O hydrogen bonds into a three-dimensional supra-molecular architecture.

SUBMITTER: Liu KH

PROVIDER: S-EPMC4908520 | biostudies-other | 2016 May

REPOSITORIES: biostudies-other

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Crystal structure of canagliflozin hemihydrate.

Liu Kai-Hang KH Gu Jian-Ming JM Hu Xiu-Rong XR Tang Gu-Ping GP

Acta crystallographica. Section E, Crystallographic communications 20160426 Pt 5

There are two canagliflozin mol-ecules (A and B) and one water mol-ecule in the asymmetric unit of the title compound, C24H25FO5S·0.5H2O [systematic name: (2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluoro-phen-yl)thio-phen-2-yl]meth-yl}-4-methylphen-yl)-6-(hy-droxy-meth-yl)-3,4,5,6-tetra-hydro-2H-pyran-3,4,5-triol hemihydrate]. The dihedral angles between the methyl-benzene and thio-phene rings are 115.7 (4) and 111.7 (4)°, while the dihedral angles between the fluoro-benzene and thio-phene rings are 24.2 (6) ...[more]

PMID: 27308030

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