N-(3-Chlorophenyl)-2,4-dimethylbenzenesulfonamide

In the molecule of the title compound, C14H14ClNO2S, the N—H bond is in a syn position with respect to the meta-Cl atom in the aniline ring. The molecule is twisted about the N—S bond with a C—SO2—NH—C torsion angle of 44.55 (17)°. The two aromatic rings are inclined relative to each other by 66.2 (1)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains parallel to the b axis.

In the molecule of the title compound, C 14 H 14 ClNO 2 S, the N-H bond is in a syn position with respect to the meta-Cl atom in the aniline ring. The molecule is twisted about the N-S bond with a C-SO 2 -NH-C torsion angle of 44.55 (17) . The two aromatic rings are inclined relative to each other by 66.2 (1) . In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into infinite chains parallel to the b axis.
KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

Comment
The amide and sulfonamide moieties are the constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004;Gowda et al., 1999), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2010), in the present work, the crystal structure The crystal packing of molecules in (I) via N-H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Experimental
The solution of 1,3-xylene (1,3-dimethylbenzene) (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 3-chloroaniline 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-(3-chlorophenyl)-2,4-dimethylbenzenesulfonamide 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, All H atoms were refined with isotropic displacement parameters set to 1.2 times of the U eq of the parent atom.    (6) 0.0007 (7)  C2 0.0360 (9) 0.0325 (9) 0.0395 (9) 0.0025 (7) 0.0061 (7) 0.0050 (7)