N-Benzoyl-2-nitrobenzenesulfonamide

In the title compound, C13H10N2O5S, the N—C bond in the C—SO2—NH—C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The molecule is twisted at the S—N bond with a torsion angle of −63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the —SO2—NH—C—O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the molecules into inversion dimers, which are linked by weak C—H⋯O and C—H⋯π interactions along the b axis.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2330).
In (I), the conformation between the N-H and C=O bonds in the C-SO 2 -NH-C(O) segment is anti (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II) (Suchetan et al., 2010). Furthermore, the N-C bond in the segment has gauche torsion with respect to the S═O bonds, while, the conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn.
The molecule is twisted at the S-N bond with the torsional angle of -63.39 (22)°, compared to the value of 68.8 (4)°i n (II).
The dihedral angle between the sulfonyl benzene ring and the -SO 2 -NH-C-O segment is 77.1 (1)°, compared to the value of 84.8 (1)° in (II). Further, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°, compared to the value of 73.9 (1)° in (II).

Experimental
The title compound was prepared by refluxing a mixture of benzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(benzoyl)-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 C-H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom).