Research Article: 4-Chloro-N-(2,4-dimethyl­phen­yl)benzene­sulfonamide

Date Published: June 01, 2011

Publisher: International Union of Crystallography

Author(s): K. Shakuntala, Sabine Foro, B. Thimme Gowda.


In the title compound, C14H14ClNO2S, the N—H bond points away from the dimethyl­phenyl ring plane. The mol­ecule is twisted at the S atom, with a C—SO2—NH—C torsion angle of −75.5 (2)°. The two aromatic rings are tilted relative to each other by 63.3 (1)°. The Cl atom on the chloro­benzene ring is disordered over two sites with site-occupation factors of 0.59 (3) and 0.41 (3), respectively. The crystal structure features inversion-related dimers linked by inter­molecular N—H⋯O hydrogen bonds.

Partial Text

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶), on N-(ar­yl)aryl­sulfonamides, see: Shakuntala et al. (2011a ▶,b ▶,c ▶) and on N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶).




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