Acta Cryst. (2013). B69, 77-85 [ doi:10.1107/S2052519212051147 ]
Abstract: The crystal structure of the high-pressure polymorph (') of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at 2.8 GPa from the -polymorph (P212121) on hydrostatic compression in saturated ethanol solution, has been determined. As a result of the phase transition, the a, c and parameters change jumpwise, whereas the changes in b parameter are continuous through the phase transition point. The high-pressure form is monoclinic (P2111) and has Z' equal to 2, the two independent molecules differing in their conformations. The hydrogen bonds expand slightly in the high-pressure polymorph after the transition, and this expansion is interrelated with the changes in molecular conformations enabling a denser packing. The transition is reversible, but the crystal quality deteriorates as a result of multiple compression-decompression cycles, and a pseudomerohedral twinning accompanies the transformation.
Keywords: polymorphism; high pressure; chlorpropamide; molecular conformations; hydrogen bonds; twinning.
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