N-(2-Chlorobenzoyl)-3-nitrobenzenesulfonamide

In the molecule of the title compound, C13H9ClN2O5S, the dihedral angle between the two aromatic rings is 84.3 (1)°. In the crystal, molecules are linked into chains via N—H⋯O(S) hydrogen bonds.

In the molecule of the title compound, C 13 H 9 ClN 2 O 5 S, the dihedral angle between the two aromatic rings is 84.3 (1) . In the crystal, molecules are linked into chains via N-HÁ Á ÁO(S) hydrogen bonds.
BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time grant to faculty. & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(2chlorobenzoyl)-3-nitrobenzenesulfonamide (I) has been determined ( Fig.1).
The conformation between the N-H and C═O bonds in the C-SO 2 -NH-C(O) segment is anti and the N-C bond in the segment has gauche torsion with respect to the S═O bonds ( Fig. 1), similar to that observed in N-(3-chlorobenzoyl)-3-nitrobenzene-sulfonamide (II) (Suchetan et al., 2012). Further, in (I), the conformation between the N-H bond and the meta-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (II). The conformation of the C═O is also syn to the ortho-Cl atom in the benzoyl ring, in contrast to the anti conformation observed between the C═O and the meta-Cl The molecule is twisted at the S-N bond with the torsional angle of -61.82 (29)°, compared to the value of -60.40 (29)°i n (II).
The dihedral angle between the sulfonyl benzene ring and the -SO 2 -NH-C-O segment is 80.4 (1)°, compared to the value of 77.0 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 84.3 (1)°, compared to the value of 83.5 (1)° in (II).
The packing of molecules linked by of N-H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing a mixture of 2-chlorobenzoic acid (0.02 mole), 3-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-(2-chlorobenzoyl)-3-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.
Rod 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) %A. 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). Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.  1.497 (4) O1-S1 1.421 (2) C8-C13 1.398 (4) O2-S1 1.431 (2)