Abstract
Epalerstat {systematic name: (5Z)-5-[(2E)-2-methyl-3-phenyl-prop-2-en-1-yl-idene]-4-oxo-2-sulfanyl-idene-1,3-thia-zolidine-3-acetic acid} crystallized as an acetone monosolvate, C15H13NO3S2·C3H6O. In the epalerstat mol-ecule, the methyl-propyl-enediene moiety is inclined to the phenyl ring and the five-membered rhodamine ring by 21.4 (4) and 4.7 (4)°, respectively. In addition, the acetic acid moiety is found to be almost normal to the rhodamine ring, making a dihedral angle of 85.1 (2)°. In the crystal, a pair of O-H⋯O hydrogen bonds between the carb-oxy-lic acid groups of epalerstat mol-ecules form inversion dimers with an R22(8) loop. The dimers are linked by pairs of C-H⋯O hydrogen bonds, enclosing R22(20) loops, forming chains propagating along the [101] direction. In addition, the acetone mol-ecules are linked to the chain by a C-H⋯O hydrogen bond. Epalerstat acetone monosolvate was found to be isotypic with epalerstat tertra-hydro-furan solvate [Umeda et al. (2017 ▸). Acta Cryst. E73, 941-944].
Highlights
Epalerstat {systematic name: (5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidine-3-acetic acid} crystallized as an acetone monosolvate, C15H13NO3S2C3H6O
The methylpropylenediene moiety is inclined to the phenyl ring and the fivemembered rhodamine ring by 21.4 (4) and 4.7 (4), respectively
The acetic acid moiety is found to be almost normal to the rhodamine ring, making a dihedral angle of 85.1 (2)
Summary
Investigation of solid forms of pharmaceuticals has attracted a great deal of attention as different crystal forms may imply different physicochemical properties (Putra et al, 2016a,b). Pharmaceutical processing stages during manufacturing, such as crystallization, can lead to the unexpected occurrence of new crystalline phases (Putra et al, 2016c). One of the important classes of pharmaceutical solids that can occur during crystallization is solvates. Solvates are defined as multi-component crystalline systems in which solvent molecules are included within the crystal structure in either a stoichiometric or non-stoichiometric manner (Griesser, 2006). It has been estimated statistically that around 33% of organic compounds have the ability to form solvates with organic solvents (Clarke et al, 2010). We report on the crystal structure of a new solvate form of epalerstat, namely epalerstat acetone monosolvate.
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