N-(4-Methylphenyl)-2-nitrobenzenesulfonamide

In the crystal of the title compound, C13H12N2O4S, the conformation of the N—H bond in the –SO2—NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The molecule is twisted at the S—N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds to form inversion dimers.

In the crystal of the title compound, C 13 H 12 N 2 O 4 S, the conformation of the N-H bond in the -SO 2 -NH-segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The molecule is twisted at the S-N bond with a torsion angle of 76.55 (18) . The dihedral angle between the planes of the rings is 72.64 (8) . In the crystal, molecules are linked by pairs of N-HÁ Á ÁO(S) hydrogen bonds to form inversion dimers.   Table 1 Hydrogen-bond geometry (Å , ). (2) 3.099 (2) 169 (2) Symmetry code: (i) Àx þ 1; Ày; Àz.
UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty. supplementary materials Acta Cryst. (2012). E68, o2745 [doi:10.1107/S1600536812035866]

Experimental
The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 4-methylaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(4-methylphenyl)-2-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point (385 K) from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.
Prism like yellow single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement
H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93Å, methyl C-H = 0.96Å. The amino H atom was freely refined with the N-H distance restrained to 0.86 (2)Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (C-methyl) of the parent atom.   Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.