title: Eight isostructural 4,4'-disubstituted N-phenylbenzenesulfonamides.
abstract: The isostructural crystals of 4-cyano-N-(4-methoxyphenyl)benzenesulfonamide, C(14)H(12)N(2)O(3)S, (I), N-(4-methoxyphenyl)-4-(trifluoromethyl)benzenesulfonamide, C(14)H(12)F(3)NO(3)S, (II), 4-iodo-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)INO(3)S, (III), 4-bromo-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)BrNO(3)S, (IV), 4-chloro-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)ClNO(3)S, (V), 4-fluoro-N-(4-methoxyphenyl)benzenesulfonamide, C(13)H(12)FNO(3)S, (VI), N-(4-chlorophenyl)-4-methoxybenzenesulfonamide, C(13)H(12)ClNO(3)S, (VII), and 4-cyano-N-phenylbenzenesulfonamide, C(13)H(10)N(2)O(2)S, (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). 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 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.
authors.affiliation: Institute of Pharmacy, University of Innsbruck, Austria. thomas.gelbrich@uibk.ac.at
authors.forename: Thomas
authors.initials: T
authors.lastname: Gelbrich
authors.forename: Terence L
authors.initials: TL
authors.lastname: Threlfall
authors.forename: Michael B
authors.initials: MB
authors.lastname: Hursthouse