Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides

Gelbrich, Thomas, Threlfall, Terence L. and Hursthouse, Michael B. (2012) Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides. Acta Crystallographica Section C: Crystal Structure Communications, 68 (10), o421-o426. (doi:10.1107/S0108270112039297).

Abstract

The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C₁₄H₁₂N₂O₃S, (I), N-(4-methoxyphenyl)-4-(trifluoromethyl) benzenesulfonamide, C₁₄H₁₂F₃NO₃S, (II), 4-iodo-N-(4-methoxyphenyl) benzenesulfonamide, C₁₃H₁₂INO₃S, (III), 4-bromo-N-(4-methoxyphenyl) benzenesulfonamide, C₁₃H₁₂BrNO₃S, (IV), 4-chloro-N-(4-methoxyphenyl) benzenesulfonamide, C₁₃H₁₂ClNO₃S, (V), 4-fluoro-N-(4-methoxyphenyl) benzenesulfonamide, C₁₃H₁₂FNO₃S, (VI), N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C₁₃H₁₂ClNO₃S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C₁₃H₁₀N₂O₂S, (VIII), contain infinite chains composed of N-H ··· O(sulfonyl) hydrogen-bonded molecules. The crystal structures of (I)-(VIII) have been compared using the XPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012). Cryst-EngComm, 14, 5454-5464]. Certain isostructural relationships in this series involve molecules with substantially different spatial demands, e. g. (VI) and (VIII) are related by the simultaneous interchange of F -> CN on the benzenesulfonamide ring and OMe -> H on the N-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)-(VIII) is unusually adaptable to different molecular shapes.

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