N-(3-Ethoxyphenyl)-4-methylbenzenesulfonamide

In the title compound, C15H17NO3S, the two aromatic rings make a dihedral angle of 69.42 (9)° with each other and the bridging C—N—S—C torsion angle is 65.76 (16)°. Weak intramolecular C—H⋯O interactions may affect the molecular conformation. Two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N—H⋯O interactions, forming an R 2 2(8) ring motif. Furthermore, two intermolecular C—H⋯π interactions contribute to the stability of the crystal packing.

In the title compound, C 15 H 17 NO 3 S, the two aromatic rings make a dihedral angle of 69.42 (9) with each other and the bridging C-N-S-C torsion angle is 65.76 (16) . Weak intramolecular C-HÁ Á ÁO interactions may affect the molecular conformation. Two neighbouring molecules generate a hydrogen-bonded dimer about a center of inversion through a pair of intermolecular N-HÁ Á ÁO interactions, forming an R 2 2 (8) ring motif. Furthermore, two intermolecular C-HÁ Á Á interactions contribute to the stability of the crystal packing.

Comment
Sulfonamide is an important functionality found in a number of synthetic as well as natural compounds possessing versatile type of biological activities e.g. herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Soledade et al., 2006;Xiao & Timberlake, 2000;Berredjem et al., 2000;Lee & Lee, 2002) activities. In the present paper, the structure of N-(3-ethoxyphenyl)-4-methylbenzene sulfonamide has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.
In the structure, two intermolecular C-H···π interactions contribute to the stability of crystal packing (Table 1).

Experimental
A mixture of 4-methyl benzene sulfonyl chloride (10.0 mmoles; 1.90 g), 3-ethoxy aniline (meta-phenetidine) (10.0 mmoles; 1.25 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature. The crude mixture was washed with water and dried. Product was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 72%. 4-Methyl benzene sulfonyl chloride and meta-phenetidine were purchased from Sigma Aldrich while all other chemicals involved were obtained from Merk, Germany.

Refinement
H atoms bonded to C atoms were positioned geometrically and refined using a riding model, with C-H = 0.93-0.97Å and U iso (H) = 1.2-1.5U eq (C). The amino H-atom was found in a difference Fourier map, and refined with a distance restraint of N-H 0.86 (2) Å. The H-atom U iso parameter was fixed at 1.2U eq (N) for the N-H group. Fig. 1. The title molecule of (I), with displacement ellipsoids drawn at the 30% probability level.

Figures
supplementary materials sup-2  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.