N-(2-Hydroxyphenyl)-4-methylbenzenesulfonamide

In the title compound, C13H13NO3S, the dihedral angle between the benzene rings is 64.15 (7)° and the C—S—N—C torsion angle is −57.18 (12)°. An intramolecular N—H⋯O hydrogen bond closes an S(5) ring. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(8) chains propagating in [100]. Weak C—H⋯π interactions are also observed.

In the title compound, C 13 H 13 NO 3 S, the dihedral angle between the benzene rings is 64.15 (7) and the C-S-N-C torsion angle is À57.18 (12) . An intramolecular N-HÁ Á ÁO hydrogen bond closes an S(5) ring. In the crystal, O-HÁ Á ÁO hydrogen bonds link the molecules into C(8) chains propagating in [100]. Weak C-HÁ Á Á interactions are also observed.

Comment
The biological activities of sulphonamide compounds are well documented, for example as antimicrobial (Ozbek et al., 2007) and anticancer (El-Sayed et al., 2011) agents. Further to our interest in related compounds with potential biactivity, we now report the synthesis and crystal structure of the title compound.
The molecular conformation features an N-H···O hydrogen bond which forms an S(5) ring (Fig. 2). In the crystal,  (Table 1).

Experimental
A mixture of 2-aminophenol (109 mg, 1 mmol) and p-toluenesulfonyl chloride (190 mg, 1 mmol) in 10 ml dioxane with addition of few drops of triethylamine as a catalyst, was refluxed for 4 h. The reaction mixture was left to cool at ambient temperature where the solid product was deposited, collected by filteration and recrystallized from ethanol in 91% yield.
Brown needles were grown from ethanol solution over 3 days at room temperature. M.p. 391 K.

Refinement
The H atoms of the NH and OH groups were found from difference Fourier maps and refined freely. The C-bound H atoms were positioned geometrically, with C-H = 0.95 and 0.98 Å and refined as riding with U iso (H) = 1.U eq (C) for the methyl H atoms and U iso (H) = 1.2U eq (C) for the other H atoms.

Computing details
Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell refinement: CrysAlis PRO (Oxford Diffraction, 2013); data reduction: CrysAlis PRO (Oxford Diffraction, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009  View of the title compound with displacement ellipsoids for non-H atoms drawn at the 50% probability level.  View of the molecular packing along the a axis of the title compound. H bonds are shown as dashed lines.

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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors 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.