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 -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.


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

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

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

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

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

	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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