Crystal structures of isomeric 3,5-dichloro-N-(2,3-dimethylphenyl)benzenesulfonamide, 3,5-dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide and 3,5-dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide

Abstract

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 R22(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 R22(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.

Keywords

• crystal structure
• sulfonamides
• N—H...O hydrogen bonds
• C—H...O interactions
• C—H...π interactions
• π–π interactions