Eight isostructural 4,4′-disubstitutedN-phenylbenzenesulfonamides

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 theXPac software and quantitative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012).CrystEngComm,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 theN-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)–(VIII) is unusually adaptable to different molecular shapes.