4-Chloro-N-(3-methylphenyl)benzenesulfonamide

In the crystal of the title compound, C13H12ClNO2S, the N—H bond is anti to the meta-methyl group in the aniline ring. The C—SO2—NH—C torsion angle is −57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

In the crystal of the title compound, C 13 H 12 ClNO 2 S, the N-H bond is anti to the meta-methyl group in the aniline ring. The C-SO 2 -NH-C torsion angle is À57.6 (2) . The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1) . The crystal structure features inversion-related dimers linked by pairs of N-HÁ Á ÁO hydrogen bonds.   Table 1 Hydrogen-bond geometry (Å , ).
KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program. The sulfonyl and the anilino benzene rings are tilted relative to each other by 84.7 (1)° in (I), compared to the values of 83.9 (1)° in (II), 67.9 (1)° (molecule 1) and 68.6 (1)° (molecule 2) in (III), and 69.1 (1)° and 82.6 (1)° in the two independent molecules of (IV).
The packing of molecules in the crystal via intermolecular N-H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with m-toluidine in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(3-methylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The compound was characterized by recording its infrared and NMR spectra.
Needle like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later restrained to the distance N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93Å and the methyl C-H = 0.96 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 (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.   (3) C2-C1-C6 120.1 (2) C8-C9-C13 120.0 (2) C2-C1-S1 120.29 (16) C11-C10-C9 120.5 (2) C6-C1-S1