N-[(4-Methylphenyl)sulfonyl]acetamide

In the title compound, C9H11NO3S, the dihedral angle between the benzene ring and the amide group is 76.7 (3)°. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers with R 2 2(8) ring motifs. The dimers are further connected by N—H⋯O and C—H⋯O hydrogen bonds into an infinite tape running parallel to the b-axis direction.

In the title compound, C 9 H 11 NO 3 S, the dihedral angle between the benzene ring and the amide group is 76.7 (3) . In the crystal, molecules are linked by pairs of C-HÁ Á ÁO hydrogen bonds into inversion dimers with R 2 2 (8) ring motifs. The dimers are further connected by N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds into an infinite tape running parallel to the b-axis direction.

N-[(4-Methylphenyl)sulfonyl]acetamide
Hoong-Kun Fun, Tze Shyang Chia, Poornima Hegde, K. Jyothi and Pramila Rita D′Souza Comment Many of the compounds containing sulfonamide groups possess a broad spectrum of biological activities (Ashton et al., 1994;Heidler & Link, 2005) and can be used as herbicides (Kamoshita et al., 1987). In addition, the nature and position of substituents play a significant role on the crystal structures of N-(aryl)-amides and N-(aryl)-sulfonamides (Gowda et al., 2007(Gowda et al., , 2010Shakuntala et al., 2011a,b;Henschel et al., 1996). In view of the importance of the biological activities of sulfonamide containing compounds, we report herein the crystal structure of the title compound.
The asymmetric unit of the title compound is shown in Fig. 1 (Gowda et al., 2010;Shakuntala et al., 2011a,b). The mean plane of the benzene ring (C2-C7) forms a dihedral angle of 76.7 (3)° with the mean plane of amide group.

Experimental
To a vigorously stirred mixture of 4-methylbenzenesulphonamide and silica sulfuric acid, acid chloride or acid anhydride was added at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added and the solid catalyst was removed by filtration. The filtrate was washed with water, dried and evaporated. The crude product was purified by recrystallization from ethanolic solution to yield colourless plates of the title compound.

Refinement
The atom H1N1 was located in a difference fourier map and refined freely [N1-H1N1 = 0.851 (19) Å]. The remaining H atoms were positioned geometrically [C-H = 0.95 and 0.98 Å] and refined using a riding model with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl group.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009  The molecular structure of the title compound with 50% probability displacement ellipsoids.  The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

N-[(4-Methylphenyl)sulfonyl]acetamide
Crystal data   (Cosier & Glazer, 1986) operating at 100.0 (1) K. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 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.