N-Benzoyl-2-methylbenzenesulfonamide

In the title compound, C14H13NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The tolyl and benzoyl groups are twisted about the S—N bond, with a C—S—N—C torsion angle of 68.8 (4)°. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 73.9 (1)°. In the crystal, the molecules are linked into C(4) chains along the c axis by N—H⋯O hydrogen bonds.

In the title compound, C 14 H 13 NO 3 S, the conformation of the N-H bond in the C-SO 2 -NH-C(O) segment is anti to the C O bond. The tolyl and benzoyl groups are twisted about the S-N bond, with a C-S-N-C torsion angle of 68.8 (4) . The dihedral angle between the sulfonyl and the benzoyl benzene rings is 73.9 (1) . In the crystal, the molecules are linked into C(4) chains along the c axis by N-HÁ Á ÁO hydrogen bonds.   The sulfonyl-bound tolyl and benzoyl groups are twisted about the S-N bond with a C1-S1-N1-C7 torsional angle of 68.8 (4)°, compared to 66.7 (2)° in (III) and 73.2 (2)° in (IV). The dihedral angle between the sulfonyl and the benzoyl benzene rings is 73.9 (1)°, compared to the values of 80.3(0.1) in (II), 73.3 (1)° in (III) and 79.4 (1)° in (IV).

Related literature
The packing of molecules linked by of N-H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing a mixture of benzoic acid (0.02 mol), 2-methylbenzenesulfonamide (0.02 mol) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(benzoyl)-2-methyl-benzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in a sodium bicarbonate solution. The compound was later 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 of its toluene solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and refined with a N-H distance restraint of 0.86 (3) %A. 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 times of the U eq of the parent atom).

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