N-(4-Methylphenyl)benzenesulfonamide

The asymmetric unit of the title compound, C13H13NO2S, contains two independent molecules. The dihedral angles between the aromatic rings in the two molecules are 78.0 (1) and 74.0 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds pack the molecules into a three-dimensional structure.

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 benzenesulfonylchloride was treated with p-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 solid N-(4methylphenyl)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 (Gowda et al., 2005).
The single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement
The H atoms of the NH groups were located in a difference map and refined with the N-H distance restrained to 0.86 (1) Å. H atoms bonded to C were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å and with their isotropic displacement parameters set to 1.2 times of the U eq of the parent C atom.    (9) N2-H2N 0.850 (9) O1-S1