Research Article: N-(3-Methyl­benzo­yl)-2-nitro­benzene­sulfonamide

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): P. A. Suchetan, Sabine Foro, B. Thimme Gowda.


In the title compound, C14H12N2O5S, the conformation between the N—H group and the ortho-nitro group in the sulfonyl benzene ring is syn and that between the C=O and meta-methyl groups in the benzoyl ring is anti. The mol­ecule is twisted at the S—N bond with a torsion angle of 64.3 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 75.73 (7)° and that between the sulfonyl and benzoyl benzene rings is 89.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

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For studies, including by our group, on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (1999 ▶, 2003 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2012 ▶), on N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶) and on N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).