Received 21 November 2012
In the title compound, C12H8Cl2N2O4S, the N-C bond in the C-SO2-NH-C segment has gauche torsions with respect to the S=O bonds. Further, the N-H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The molecule is twisted at the S-N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intramolecular bifurcated N-H(O,O) hydrogen bond. In the crystal, pairs of N-HO(S) hydrogen bonds link the molecules into inversion dimers with R22(8) motifs.
For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5027 ).
BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its Promotion of University Research and Scientific Excellence Programme.
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