Date Published: April 01, 2011
Publisher: International Union of Crystallography
Author(s): K. Shakuntala, Sabine Foro, B. Thimme Gowda.
In the crystal structure of the title compound, C12H9Cl2NO2S, the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. The molecule is twisted at the S atom with an C—SO2—NH—C torsion angle of 57.6 (3)°. The N—H bond is syn to the ortho-chloro group in the anilino benzene ring. The two benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion dimers linked by N—H⋯O(S) hydrogen bonds. An intramolecular N—H⋯Cl hydrogen bond is also observed.
For our study of the effect of substituents on the oxidative strengths of N-chloro,N-arylsulfonamides, see: Gowda & Shetty (2004 ▶), and on the structures of N-(aryl)-amides, see: Gowda et al. (2004 ▶), N-(aryl)-arylsulfonamides, see: Shakuntala et al. (2011 ▶) and N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ▶).