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

In the title compound, C14H14ClNO2S, the N—H bond points away from the dimethylphenyl ring plane. The molecule is twisted at the S atom, with a C—SO2—NH—C torsion angle of −75.5 (2)°. The two aromatic rings are tilted relative to each other by 63.3 (1)°. The Cl atom on the chlorobenzene ring is disordered over two sites with site-occupation factors of 0.59 (3) and 0.41 (3), respectively. The crystal structure features inversion-related dimers linked by intermolecular N—H⋯O hydrogen bonds.

In the title compound, C 14 H 14 ClNO 2 S, the N-H bond points away from the dimethylphenyl ring plane. The molecule is twisted at the S atom, with a C-SO 2 -NH-C torsion angle of À75.5 (2) . The two aromatic rings are tilted relative to each other by 63.3 (1) . The Cl atom on the chlorobenzene ring is disordered over two sites with site-occupation factors of 0.59 (3) and 0.41 (3), respectively. The crystal structure features inversion-related dimers linked by intermolecular N-HÁ Á ÁO hydrogen bonds.
The packing of molecules into dimers in the title compound via intermolecular N-H···O hydrogen bonds (Table 1) is shown in Fig. 2.
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 2,4-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 resulting 4-chloro-N-(2,4-dimethylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water.
It was then recrystallized to constant melting point from aqueous 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 its coordinates were refined with the N-H distance restrained to 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 methyl C-H = 0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 supplementary materials sup-2 times of the U eq of the parent atom). Atom CL1 is disordered and was refined using a split model. The corresponding site-occupation factors were refined so that their sum was unity with occupancy factors converging to 0.59 (3) and 0.41 (3).
The corresponding bond distances in the disordered group were restrained to be equal. Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.