Crystal structure of canagliflozin hemihydrate

Abstract

There are two canagliflozin molecules (A and B) and one water molecule in the asymmetric unit of the title compound, C24H25FO5S 0.5H2O [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.