Acta Crystallographica Section B

Structural Science, Crystal Engineering and Materials

Volume 69, Part 1 (February 2013)


research papers



Acta Cryst. (2013). B69, 77-85    [ doi:10.1107/S2052519212051147 ]

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

Y. V. Seryotkin, T. N. Drebushchak and E. V. Boldyreva

Abstract: The crystal structure of the high-pressure polymorph ([alpha]') of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at ~ 2.8 GPa 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.

Keywords: polymorphism; high pressure; chlorpropamide; molecular conformations; hydrogen bonds; twinning.


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Structure factor file (CIF format) (56.9 kbytes)
[ doi:10.1107/S2052519212051147/gp50581.18GPasup2.hkl ]
Contains datablock a_cpa118abs


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Structure factor file (CIF format) (50.5 kbytes)
[ doi:10.1107/S2052519212051147/gp5058acpa_2.10GPasup3.hkl ]
Contains datablock a_cpa210abs


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Structure factor file (CIF format) (50.0 kbytes)
[ doi:10.1107/S2052519212051147/gp5058acpa_2.50GPasup4.hkl ]
Contains datablock a_cpa250abs


hkldisplay filedownload file

Structure factor file (CIF format) (49.8 kbytes)
[ doi:10.1107/S2052519212051147/gp5058acpa_2.63GPasup5.hkl ]
Contains datablock a_cpa263abs


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Structure factor file (CIF format) (84.2 kbytes)
[ doi:10.1107/S2052519212051147/gp5058acpa_2.91GPasup6.hkl ]
Contains datablock new


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Structure factor file (CIF format) (86.1 kbytes)
[ doi:10.1107/S2052519212051147/gp5058acpa_3.33GPasup7.hkl ]
Contains datablock a_cpa_333


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