N-(4-Methylbenzoyl)-4-nitrobenzenesulfonamide

In the title compound, C14H12N2O5S, the dihedral angle between the nitrophenyl group and the –S—NH—C—O fragment is 80.74 (17)° and that between the nitrophenyl and methylphenyl groups is 87.66 (14)°. The C—S—N—C torsion angle at the S—N bond is −67.0 (3)°. In the crystal, molecules are linked into C(4) chains via N—H⋯O hydrogen bonds.

In the title compound, C 14 H 12 N 2 O 5 S, the dihedral angle between the nitrophenyl group and the -S-NH-C-O fragment is 80.74 (17) and that between the nitrophenyl and methylphenyl groups is 87.66 (14) . The C-S-N-C torsion angle at the S-N bond is À67.0 (3) . In the crystal, molecules are linked into C(4) chains via N-HÁ Á ÁO hydrogen bonds.
The conformation of the N-H bond in the C-SO 2 -NH-C(O) segment is anti with respect to the C=O bond ( Fig.1), similar to that observed in N-(4-methylbenzoyl)-4-chlorobenzenesulfonamide (I) (Suchetan et al., 2010).
In the title compound, the molecules are twisted at the S-N bonds with the torsional angle of -67.0 (3)°, compared to the value of 69.0 (2)° in (I).
The dihedral angle between the sulfonyl benzene ring and the -SO 2 -NH-C-O segment is 79.6 (1)°, compared to the value of 77.2 (1)° in (I).
The dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.3 (1)°, compared to the value of 89.5 (1)° in (I).
The packing of molecules linked by of N-H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, 4-nitrobenzenesulfonamide and phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.
Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation from its toluene solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and restrained to N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C-H distances of 0.93Å (C-aromatic) and 0.96Å (Cmethyl).
All H atoms were refined with isotropic displacement parameters were set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (Cmethyl).

Figure 1
Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq C1 0.5261 (