N-(4-Hydroxyphenyl)benzenesulfonamide

The title compound, C12H11NO3S, synthesized by the reaction of benzene sulfonyl chloride with para-aminophenol, is of interest as a precursor to biologically active sulfur-containing heterocyclic compounds. The structure is stabilized by N—H⋯O and O—H⋯O hydrogen bonds.

The title compound, C 12 H 11 NO 3 S, synthesized by the reaction of benzene sulfonyl chloride with para-aminophenol, is of interest as a precursor to biologically active sulfur-containing heterocyclic compounds. The structure is stabilized by N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds.

Comment
In the present paper, the structure of N-(4-hydroxyphenyl) benzene sulfonamide ( Fig. 1) has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2006, 2009Khan et al., 2009). Bond lengths and bond angles are almost similar to those in the related molecules (Khan et al., 2009). The molecules are linked through intermolecular N-H···O and O-H···O hydrogen bonds ( Fig. 2; Table 1).

Experimental
A mixture of benzene sulfonyl chloride (10.0 mmoles; 1.766 g), para-aminophenol (10.0 mmoles; 1.286 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature followed by evaporation of the solvent. The crude mixture was washed with water and dried. Product obtained was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 73%.

Refinement
All H atoms were identified in the difference map. Nevertheless, they were fixed in ideal positions and treated as riding on their parent atoms. The following distances were used: C methyl -H 0.98 Å, C aromatic -H 0.95Å, O-H 0.84 Å. U(H) was set to 1.2U eq of the parent atoms or 1.5U eq for methyl groups.

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.