2-Methyl-N-(2-methylbenzoyl)benzenesulfonamide

In the title compound, C15H15NO3S, the 2-methylphenyl ring bonded to the sulfonyl group is disordered with site-occupation factors of 0.75:0.25. The dihedral angles between the two aromatic rings are 67.6 (1) and 69.2 (1)° for the major and the minor occupied sites, respectively. In the crystal, molecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds.

The molecules are linked into chains by N-H···O(S) hydrogen bonds (Table 1 and Fig. 2).

Experimental
The title compound was prepared by refluxing a mixture of 2-methylbenzoic acid, 2-methylbenzenesulfonamide and phosphorous oxy chloride for 5 h on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid, 2-methyl-N-(2-methylbenzoyl)benzenesulfonamide, was separated, 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 compound was recrystallized to the constant melting point.
Prism like colourless single crystals of the title compound were grown by slow evaporation of its toluene solution at room temperature.

supplementary materials sup-2 Refinement
The H atom of the NH group was located in a difference map and restrained to N-H = 0.86 (1) %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.
The methylphenyl ring with atoms C1, C2, C3, C4, C5, C6 and C14 is disordered over two sites related by a twofold rotation. The corresponding site-occupation factors were fixed to 0.75:0.25 and their corresponding bond distances in the disordered groups were restrained to be equal.