4-Nitro-N-phenylbenzenesulfonamide

In the title compound, C12H10N2O4S, the dihedral angle between the aromatic rings is 36.19 (18)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains running along the a axis.

UC thanks Mangalore University for the award of a research fellowship. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty. supplementary materials Acta Cryst. (2012). E68, o2872 [doi:10.1107/S1600536812037798] 4-Nitro-N-phenylbenzenesulfonamide U. Chaithanya, Sabine Foro and B. Thimme Gowda Comment As a part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011;Gowda & Weiss, 1994;Shahwar et al., 2012); N-arylsulfonamides (Chaithanya et al., 2012;Gowda et al., 2003) and N-chloroarylsulfonamides (Gowda et al., 2005;Shetty & Gowda, 2004),in the present work, the crystal structure of The dihedral angle between the sulfonyl and the anilino rings is 36.19 (18)°, compared to the value of 59.55 (7)° in (I).
In the crystal, the intermolecular N-H···O hydrogen bond interactions link the molecules into C(4) chains. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by treating 4-nitrobenzenesulfonylchloride with aniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(phenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.
Plate like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement
H atoms bonded to C were positioned with idealized geometry using a riding model with C-H = 0.93 Å. The coordinates of the amino H atom were refined with the N-H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U eq of the parent atom.   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 R-factors(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.