4-Chloro-N-(2,6-dimethylphenyl)benzenesulfonamide

In the title compound, C14H14ClNO2S, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The molecule is twisted at the S atom with an C—SO2—NH—C torsion angle of −69.9 (2)°. The two aromatic rings are tilted relative to each other by 31.9 (1)°. In the crystal, the molecules are packed into zigzag chains along the b axis via intermolecular N—H⋯O hydrogen bonds.

In the title compound, C 14 H 14 ClNO 2 S, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The molecule is twisted at the S atom with an C-SO 2 -NH-C torsion angle of À69.9 (2) . The two aromatic rings are tilted relative to each other by 31.9 (1) . In the crystal, the molecules are packed into zigzag chains along the b axis via intermolecular N-HÁ Á ÁO hydrogen bonds.
KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.
The packing of molecules in (I) into zigzag chains through N-H···O(S) hydrogen bonding (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 2,6-dimethylaniline 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-(2,6-dimethylphenyl)-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.
Prism 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 = 0.93 Å 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).