2-Amino-N,3-dimethylbenzamide

In the title compound, C9H12N2O, the mean plane through the amide group and the benzene ring form a dihedral angle of 33.93 (7)°. An intramolecular N—H⋯O hydrogen bond is present. In the crystal, molecules are linked by N—H⋯N and N—H⋯O hydrogen bonds, forming double-stranded chains parallel to the b axis.

In the title compound, C 9 H 12 N 2 O, the mean plane through the amide group and the benzene ring form a dihedral angle of 33.93 (7) . An intramolecular N-HÁ Á ÁO hydrogen bond is present. In the crystal, molecules are linked by N-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds, forming double-stranded chains parallel to the b axis.
In the title compound ( Fig. 1), the least-square mean plane through the amide group (C8/C9/O1/N2) form a dihedral angle of 33.93 (7)° with the benzene ring. The molecular conformation is stabilized by an intramolecular N-H···O hydrogen bond (Table 1). In the crystal structure, intermolecular N-H···N and N-H···O hydrogen interactions link molecules into double chains running parallel to the b axis.

Experimental
The title compound was prepared according to the literature method (Witt & Bergman, 2000) by stirring isatoic anhydride with aqueous methylamine. Isatoic anhydride was prepared by reaction of anthranilic acid with triphosgene in good yield (Coppola, 1980). The title compound (0.2 g) was dissolved in ethanol (50 ml) at room temperature. Colourless blocks were obtained through slow evaporation after two weeks.

Refinement
The H atoms were placed at calculated positions, with C-H = 0.93-0.98 Å, and refined as riding with U iso (H) = 1.2-1.5U eq (C). 841 Friedel pairs were not merged.

Computing details
Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008  The molecular structure of the title compound showing 50% probability displacement ellipsoids and atom-numbering scheme. 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.