5-Amino-2-methylbenzenesulfonamide

In the crystal structure of the title compound, C7H10N2O2S, a benzoic acid derivative, intermolecular N—H⋯O interactions link the molecules into a three-dimensional network.

In the crystal structure of the title compound, C 7 H 10 N 2 O 2 S, a benzoic acid derivative, intermolecular N-HÁ Á ÁO interactions link the molecules into a three-dimensional network.
In the crystal structure, intermolecular N-H···O interactions (Table 1) link the molecules into a three-dimensional network ( Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental
For the preparation of the title compound, ammonium hydroxide (25 ml) was added to N-acetylamino-2-toluenesulfonyl chloride (10.7 g). The mixture was cooled down, and sulfuric acid solution (10 ml, 20%) was slowly added. The mixture was kept at 273-278 K for 5 min. The corresponding sulfonamide was collected, washed with ice water and dried to give a crystalline crude colorless solid (yield; 67%). Then, hydrochloric acid (15 ml, 18%) was added to N-acetyltoluenesulfonamide (5.6 g) and the mixture was refluxed for 20 min. The resulting solution was diluted with an equal volume of water and sodium carbonate until pH = 8. After cooling, the precipitate was collected and washed with ice water (yield; 3.9 g).
Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH 2 ) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. 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.