2-Nitro-N-phenylbenzenesulfonamide

In the title compound, C12H10N2O4S, the conformation of the N—H bond in the –SO2—NH– fragment is syn to the ortho-nitro group in the sulfonylbenzene ring. The molecule is twisted at the S—N bond, the C—N—S—C torsion angle being −72.83 (15)°. The dihedral angle between the benzene rings is 59.55 (7)°. The amide H atom and the nitro group O atom form an intramolecular hydrogen bond, generating an S(7) motif. In the crystal, C—H⋯O hydrogen-bond interactions link the molecules into S 2 2(10) networks.

In the title compound, C 12 H 10 N 2 O 4 S, the conformation of the N-H bond in the -SO 2 -NH-fragment is syn to the orthonitro group in the sulfonylbenzene ring. The molecule is twisted at the S-N bond, the C-N-S-C torsion angle being À72.83 (15) . The dihedral angle between the benzene rings is 59.55 (7) . The amide H atom and the nitro group O atom form an intramolecular hydrogen bond, generating an S(7) motif. In the crystal, C-HÁ Á ÁO hydrogen-bond interactions link the molecules into S 2 2 (10) networks.
The conformation of the N-H bond in the -SO 2 -NH-segment is syn to the ortho-nitro group in the sulfonyl benzene ring, similar to that observed in N-(benzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). The molecule is twisted at the S-N bond with the torsional angle of -72.83 (15)°, compared to the value of -63.39 (22)° in (I).
The dihedral angle between the sulfonyl and the anilino rings is 59.55 (7)°, compared to the value of 88.6 (1)° in (I).
The amide H-atom showed intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring (Table 1).
In the crystal, the intermolecular C-H···O hydrogen bond interactions link the molecules. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by treating 2-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)-2-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.
Prism 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 the aromatic C-H = 0.93 Å.
The amino H atom was freely refined with the N-H distances restrained to 0.86 (1) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U eq of the parent atom. The (-2 0 4) reflection was probably affected by the beamstop and was omitted from the refinement.  (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).  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.