N-(2,6-Dimethylphenyl)-2,4-dimethylbenzenesulfonamide

Molecules of the title compound, C16H19NO2S, are bent at the S atom with a C—SO2—NH—C torsion angle of −60.0 (2)°. The dihedral angle between the phenylsulfonyl and aniline rings is 41.7 (1)°. In the crystal, molecules are packed into centrosymmetric dimers through pairs of N—H⋯O(S) 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.
In the crystal, packing of molecules into chains through of N-H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Experimental
The solution of m-xylene (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 2,4-dimethylbenzenesulfonylchloride 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 solid 2,4-dimethyl-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 purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006).
The prism like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by a 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 methyl C-H = 0.96 Å. The U iso (H) values were set at 1.2U eq (C-aromatic, N) and 1.5U eq (C-methyl).. Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.