Crystal structures of isomeric 35-di­chloro-N-(23-di­methyl­phen­yl)benzene­sulfonamide 35-di­chloro-N-(26-di­methyl­phen­yl)benzene­sulfonamide and 35-di­chloro-N-(35-di­methyl­phen­yl)benzene­sulfonamide

摘要

The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di­chloro-N-(2,3-di­methyl­phen­yl)-benzene­sulfonamide (I), 3,5-di­chloro-N-(2,6-di­methyl­phen­yl)benzene­sulfonamide (II) and 3,5-di­chloro-N-(3,5-di­methyl­phen­yl)benzene­sulfonamide (III) are described. The mol­ecules 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 mol­ecular conformation of (II) is stabilized by intra­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions. The crystal structure of (I) features N—H⋯O hydrogen-bonded R 2 ²(8) loops inter­connected via C(7) chains of C—H⋯O inter­actions, forming a three-dimensional architecture. The structure also features π–π inter­actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N—H⋯O hydrogen-bonded R 2 ²(8) loops are inter­connected via π–π inter­actions [inter­centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N—H⋯O hydrogen-bonded mol­ecules running parallel to [010] are connected via C—H⋯π inter­actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π–π inter­actions [inter­centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.