4-Methyl-N-(4-methylphenyl)benzenesulfonamide

In the title compound, C14H15NO2S, the two aromatic rings enclose a dihedral angle of 70.53 (10)°. A weak intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.


Comment
Sulfonamides are well known for their antibacterial and enzyme inhibitor properties (Pandya et al., 2003). Aromatic sulfonamides were also reported to inhibit the growth of tumor cells (Supuran & Scozzafava, 2000). In continuation of our studies (Sharif et al., 2010), herein, we report the crystal structure of the title compound.
The molecular conformation of the title compound is stabilized by a weak intramolecular C-H···O hydrogen bond, generating an S(6) ring motif (Etter, 1990;Bernstein et al., 1995) (Table 1). In the crystal structure of the title compound, inversion-related molecules are linked into dimers by pairs of N-H···O hydrogen bonds, forming an R 2 2 (8) graph-set motif (Table 1 and Fig. 2).

Experimental
The synthesis of the title compound was performed by the procedure reported by Deng & Mani (2006). 4-methyl aniline 0.535 g (5 mmol) was dissolved in 10 ml distilled water and pH of the solution was adjusted to 8 by using (3 M) Na 2 CO 3 .
p-toluene sulfonyl chloride 0.95 g (5 mmol) was added under continuous stirring at room temperature. pH of the reaction mixture during stirring was maintained between 8-9 with 3 M Na 2 CO 3 . When the solution was clear, pH was adjusted to 2-3 using 3 M HCl. The precipitate formed was filtered and recrystallized from methanol.

Refinement
The H atom bonded to N was refined freely. The other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C-H = 0.93-0.96 Å and U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C). Fig. 1. Perspective view of the title compound with the atoms labelled and displacement ellipsoids depicted at the 30% probability level for all non-H atoms.

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and tor-

sion angles
Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted Rfactors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.