A high-pressure polymorph of chlorpropamide formed on hydrostatic compression of the [alpha]-form in saturated ethanol solution

The crystal structure of the high-pressure polymorph ([alpha]') of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at 2.8GPa from the [alpha]-polymorph (P212121) on hydrostatic compression in saturated ethanol solution, h...

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Bibliographic Details
Published in:Acta crystallographica. Section B, Structural science Structural science, 2013-02, Vol.69 (1), p.77
Main Authors: Seryotkin, Yury V, Drebushchak, Tatiana N, Boldyreva, Elena V
Format: Article
Language:English
Subjects:
Crystal structure
Crystallography
Ethanol
Polymorphism
Online Access:Get full text
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Summary:The crystal structure of the high-pressure polymorph ([alpha]') of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at 2.8GPa from the [alpha]-polymorph (P212121) on hydrostatic compression in saturated ethanol solution, has been determined. As a result of the phase transition, the a, c and [alpha] 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. [PUBLICATION ABSTRACT]
ISSN:2052-5192
2052-5206
DOI:10.1107/S0108768112051142