N-(Phenylsulfonyl)acetamide

In the title compound, C8H9NO3S, the N—H bond is in an antiperiplanar conformation with respect to the C=O bond. The crystal packing is stabilized by N—H⋯O hydrogen bonds, generating C(4) chains propagating in [001].

In the title compound, C 8 H 9 NO 3 S, the N-H bond is in an antiperiplanar conformation with respect to the C O bond. The crystal packing is stabilized by N-HÁ Á ÁO hydrogen bonds, generating C(4) chains propagating in [001].
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5256).

N-(Phenylsulfonyl)acetamide
B. T. Gowda, S. Foro, P. G. Nirmala and H. Fuess Comment Sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors can give rise to polymorphism (Yang & Guillory, 1972).
The packing of molecules linked by N-H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing benzenesulfonamide (0.10 mole) with an excess of acetyl chloride (0.20 mole) for about an hour on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in warm dilute sodium hydrogen carbonate solution.
The title compound was reprecipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared spectra.
Rod like colorless single crystals were obtained from a slow evaporation of an ethanolic solution of the compound.

Refinement
The H atom of the NH group was located in a difference map. Its coordinates were refined with a distance restraint of N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å.
All H atoms were refined with isotropic displacement parameters set to 1.2 times of the U eq of the parent atom.
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.