Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide

摘要

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3?(6)° in (I), 42.1?(2)° in (II) and 54.4?(3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C—H?O hydrogen bonds and C—H?π inter-actions. The crystal structure of (I) features N—H?O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C—H?O inter-actions, forming a three-dimensional architecture. The structure also features π–π inter-actions [Cg?Cg = 3.6970?(14)??]. In (II), N—H?O hydrogen-bonded R22(8) loops are inter-connected via π–π inter-actions [inter-centroid distance = 3.606?(3)??] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N—H?O hydrogen-bonded mol-ecules running parallel to [010] are connected via C—H?π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π–π inter-actions [inter-centroid distance = 3.8303?(16)??] to form a three-dimensional architecture.