N-Phenyl-N-(prop-2-en-1-yl)benzenesulfonamide

In the molecule of the title compound, C15H15NO2S, the dihedral angle between the two phenyl rings is 41.8 (3)°. The S atom has a distorted tetrahedral environment. In the crystal structure, C—H⋯O hydrogen bonds link the molecules into a ribbon-like structure along [010].


Comment
Benzenesulfonamide derivatives have been used as starting materials for the preparation of a variety of sulfonamide drugs, such as inhibitors of HIV infection (Kazmierski et al., 2004) and antihypertensive drugs (Beate et al., 1998). In addition, they have also been employed in the preparation of gene probe labelling (Skrzipczyk et al., 1994). As an extension of our previous studies (Arshad et al., 2009;Khan et al., 2009), we report here the crystal structure of the title compound.
In the crystal structure, adjacent molecules are linked via C-H···O hydrogen bonds (Table 1) to form a ribbon-like structure along the b axis (Fig.2).
The stirring was continued further for a period of 3 h and the contents were poured over crushed ice. The precipitated product was isolated, washed and recrystallized from methanol solution.

Refinement
H atoms were placed in calculated positions, with C-H = 0.93 or 0.97 Å and included in the final cycles of refinement using a riding model, with U iso (H) = 1.2U eq (parent atom). Fig. 1. The molecular structure of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids.

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 supplementary materials sup-3 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 > 2sigma(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.