N-(3,5-Dichlorophenyl)benzenesulfonamide

In the crystal structure of the title compound, C12H9Cl2NO2S, the aromatic rings are aligned at 57.0 (1)°. The molecules form chains via intermolecular N—H⋯O hydrogen bonds.

In the crystal structure of the title compound, C 12 H 9 Cl 2 NO 2 S, the aromatic rings are aligned at 57.0 (1) . The molecules form chains via intermolecular N-HÁ Á ÁO hydrogen bonds.

Comment
As part of a study of the substituent effects on the crystal structures of N-(aryl)-benzenesulfonamides (Gowda et al., 2008a,b), in the present work, the structure of N-(3,5-dichlorophenyl)-benzenesulfonamide (N35DCPBSA) has been determined.

Experimental
The solution of benzene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 benzenesulfonylchloride was treated with 3,5-dichloroaniline 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-(3,5-dichlorophenyl)-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 (Shetty & Gowda, 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by evaporating it at room temperature.

Refinement
The H atom of the NH group was located in a diffrerence map and later restrained to the distance 0.86 (1) Å The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom).