2,4-Dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide

In the crystal of the title compound, C14H13Cl2NO2S, the N—H bond in the C—SO2—NH—C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of −100.48 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. Intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains.

In the crystal of the title compound, C 14 H 13 Cl 2 NO 2 S, the N-H bond in the C-SO 2 -NH-C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The molecule is bent at the S atom with a C-SO 2 -NH-C torsion angle of À100.48 (18) . The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1) . Intermolecular N-HÁ Á ÁO hydrogen bonds link the molecules into infinite chains.
In (I), the N-H bond in the C-SO 2 -NH-C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and orients itself towards the ortho-chloro group in the sulfonyl benzene ring. The molecule is bent at the S atom with C-SO 2 -NH-C torsion angle of -100.48 (18) The sulfonyl and the aniline benzene rings are tilted relative to each other by 69.6 (1)°, compared to the value of 44.6 (1)°i n (II).
The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006;Gelbrich et al., 2007).
The N-H···O intermolecular hydrogen bonds (Table 1) link the molecules into chains. Part of the crystal structure is shown in Fig. 2.

Experimental
The solution of 1,3-dichlorobenzene (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-dichlorobenzenesulfonylchloride 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-dichloro-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).
Prism like light pink 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 difference map and later restrained to N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93 Å and methyl C-H = 0.96 Å. All H atoms were refined with isotropic displacement parameters. 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 labeling scheme and displacement ellipsoids are drawn at the 50% probability level.  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.