4-Chloro-2-methyl-N-phenylbenzenesulfonamide

There are two molecules in the asymmetric unit of the title compound, C13H12ClNO2S, with similar conformations. The orientations of the ortho-methyl groups in the sulfonyl benzene rings are in the direction of the N—H bonds of the sulfonamide groups. In the crystal, the molecules are each linked into centrosymmetric dimers through N—H⋯O hydrogen bonds and packed into a layered structure diagonally in the bc plane.

There are two molecules in the asymmetric unit of the title compound, C 13 H 12 ClNO 2 S, with similar conformations. The orientations of the ortho-methyl groups in the sulfonyl benzene rings are in the direction of the N-H bonds of the sulfonamide groups. In the crystal, the molecules are each linked into centrosymmetric dimers through N-HÁ Á ÁO hydrogen bonds and packed into a layered structure diagonally in the bc plane.
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-methyl-4-chlorobenzenesulfonylchloride was treated with aniline 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 cc). The resultant solid N-(phenyl)-2-methyl-4-chlorobenzenesulfonamide 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. The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement
The H atoms of the NH groups were located in a diffrerence map and their positions refined, with N-H = 0.88 (4)-0.91 (5) Å.
The carbon-bound H atoms were positioned with idealized geometry and refined using a riding model, with C-H distances 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom). For methyl group U iso (H) = 1.5 U eq . supplementary materials sup-2

Special details
Geometry. All e.s. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.