Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 12 (December 2004)

av1199 scheme

Acta Cryst. (2004). C60, o843-o846 [doi:10.1107/S0108270104024771]

Solvates of zafirlukast

D. Goldring, M. Botoshansky, R. L. Khalfin, B. Pertsikov, G. Nisnevitch, V. Ponomarev, I. Zaltzman, A. Gutman and M. Kaftory

Abstract: The crystal structures of three solvates of zafirlukast [systematic name: cyclopentyl N-{1-methyl-3-[2-methyl-4-(o-tolylsulfonylaminocarbonyl)benzyl]-1H-indol-5-yl}carbamate], viz. the monohydrate, C₃₁H₃₃N₃O₆S·H₂O, (I), the methanol solvate, C₃₁H₃₃N₃O₆S·CH₃OH, (II), and the ethanol solvate, C₃₁H₃₃N₃O₆S·C₂H₅OH, (III), have been determined by single-crystal X-ray diffraction analysis. All three compounds crystallize in the monoclinic crystal system. Zafirlukast adopts a similar Z-shaped conformation in all three solvates. The methanol and ethanol solvates are isostructural. The packing of the zafirlukast molecules in all three crystal structures is similar and is expressed by hydrogen-bonded molecules that are related by translation, along (101) in (I) and along the b axis in (II) and (III). The methanol and ethanol solvent molecules are hydrogen bonded to two molecules of zafirlukast. The water molecule, on the other hand, acts as a connector via hydrogen bonds between three molecules of zafirlukast. The solvent molecules are not released at temperatures below the melting points of the solvates.

Formula: C₃₁H₃₃N₃O₆S·H₂O, C₃₁H₃₃N₃O₆S·CH₄O and C₃₁H₃₃N₃O₆S·C₂H₆O

Online 11 November 2004


	Structure factor file (CIF format) (249.2 kbytes) Contains datablock I

	Structure factor file (CIF format) (139.4 kbytes) Contains datablock II

	Structure factor file (CIF format) (133.8 kbytes) Contains datablock III

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