N-(4-Methylphenylsulfonyl)-3-nitrobenzamide

In the title compound, C14H12N2O5S, the dihedral angle between the aromatic rings is 86.29 (1)° and the conformation between the C=O bond of the amide group and the meta-NO2 group is syn. The C—S—N—C torsion angle is −65.87 (19)° and the molecule has an L-shaped conformation. In the crystal, the molecules are connected into inversion dimers through pairs of N—H⋯O hydrogen bonds and C—H⋯O interactions forming R 2 2(8) and R 2 2(14) loops, respectively. The dimers are connected by further C—H⋯O interactions, thereby forming (100) sheets.

In the title compound, C 14 H 12 N 2 O 5 S, the dihedral angle between the aromatic rings is 86.29 (1) and the conformation between the C=O bond of the amide group and the meta-NO 2 group is syn. The C-S-N-C torsion angle is À65.87 (19) and the molecule has an L-shaped conformation. In the crystal, the molecules are connected into inversion dimers through pairs of N-HÁ Á ÁO hydrogen bonds and C-HÁ Á ÁO interactions forming R 2 2 (8) and R 2 2 (14) loops, respectively. The dimers are connected by further C-HÁ Á ÁO interactions, thereby forming (100) sheets.

Introduction
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2010(Suchetan et al., , 2011(Suchetan et al., , 2012, we report here the crystal structure of the title compound (I) (Fig 1).

Synthesis and crystallization
The title compound (I) was prepared by refluxing a mixture of 3-nitrobenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxychloride (POCl 3 ) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The compound obtained was filtered and later dried (Melting point: 459 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the Ueq of the parent atom).

Results and discussion
In I, the dihedral angle between the two aromatic rings is 86.29 (1)°. Compared to this, the dihedral angle is 79.4 (1)° in N-(4-methylphenylsulfonyl)-benzamide (II) (Suchetan et al., 2010), 89.8 (1)° in N-(4-methylphenylsulfonyl)-4-nitrobenzamide (III) (Suchetan et al., 2011) and 86.9 (2)° in N-(phenylsulfonyl)-3-nitrobenzamide (IV) (Suchetan et al., 2012). Thus, introducing a nitro group into the benzoyl ring results in an increase of the dihedral angle between the aromatic rings. The conformation between the N-H bond and the meta-NO 2 group is anti in contrast to the syn conformation observed in IV (Suchetan et al., 2012). The molecule is twisted at the S atom, the dihedral angle between the planes defined by the S-N-C=O segment in the central chain and the sulfonyl benzene rings being 79.16 (1)°.

Figure 2
Formation of sheets in the crystal structure. Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 > 2σ(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.