N-(4-Methylbenzoyl)-2-nitrobenzenesulfonamide

The asymmetric unit of the title compound, C14H12N2O5S, contains two independent molecules. The dihedral angles between the aromatic rings are 82.03 (9) and 79.47 (8)° in the two independent molecules. In the crystal, the two molecules in the asymmetric unit are linked into dimers via pairs of N—H⋯O(S) hydrogen bonds to generate C(4) chains.

The asymmetric unit of the title compound, C 14 H 12 N 2 O 5 S, contains two independent molecules. The dihedral angles between the aromatic rings are 82.03 (9) and 79.47 (8) in the two independent molecules. In the crystal, the two molecules in the asymmetric unit are linked into dimers via pairs of N-HÁ Á ÁO(S) hydrogen bonds to generate C(4) chains.
BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.
the ortho-nitro groups in the sulfonyl benzene rings are syn, similar to that observed in N-(3-methylbenzoyl)-2-nitrobenzenesulfonamide (II) (Suchetan et al., 2012). In the crystal, the intermolecular N-H···O (S) hydrogen bonds (Table 1) link the molecules into chains. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing a mixture of p-methylbenzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(4-methylbenzoyl)-2-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.
Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later restrained to N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93 Å and the methyl C -H = 0.93 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).

Special details
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.