N-(3-Methylbenzoyl)benzenesulfonamide

The asymmetric unit of the title compound, C14H13NO3S, contains three independent molecules in which the dihedral angles between the sulfonyl and benzoyl benzene rings are 83.3 (2), 84.4 (2) and 87.6 (2)°. In the crystal, molecules are linked into chains running along the a axis via N—H⋯O hydrogen bonds.

The asymmetric unit of the title compound, C 14 H 13 NO 3 S, contains three independent molecules in which the dihedral angles between the sulfonyl and benzoyl benzene rings are 83.3 (2), 84.4 (2) and 87.6 (2) . In the crystal, molecules are linked into chains running along the a axis 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 to the C=O bond ( Fig.1), similar to that observed in N-(3-chlorobenzoyl)benzenesulfonamide (I) (Gowda et al., 2009).
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 3-methylbenzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 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 later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.
Plate like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of the solvent from its toluene solution at room temperature.

Refinement
The coordinates of the H atoms bonded to N were refined with the to N-H distance restrained to 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C-H distances of 0.93 Å (C-aromatic) and 0.96 Å (C-methyl).
All H atoms were refined with isotropic displacement parameters were set at 1.2 U eq (C aromatic , N) and 1.5 U eq (C methyl ).
The (1 1 1) reflection is probably affected by the beamstop and was omitted from the refinement.   Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

Special details
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.