2-Amino-6-chloro-N-methylbenzamide

In the title compound, C8H9ClN2O, the dihedral angle between the benzene ring and the methylamide substituent is 68.39 (11)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming layers parallel to the ab plane.

In the title compound, C 8 H 9 ClN 2 O, the dihedral angle between the benzene ring and the methylamide substituent is 68.39 (11) . In the crystal, molecules are linked by N-HÁ Á ÁO hydrogen bonds, forming layers parallel to the ab plane.
In the title compound ( Fig. 1) the dihedral angle formed by the benzene ring and the methylamide substituent (r.m.s. deviation 0.0065 Å) is 68.39 (11)°. In the crystal structure, molecules are connected via N-H···O hydrogen bonds (Table   1) into layers running parallel to the ab plane.

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
All H atoms were placed at calculated positions, with C-H = 0.93-0.98 Å, N-H = 0.86 Å, and refined as riding with U iso (H) = 1.2U eq (C, N) or 1.5U eq (C) for methyl H atoms.

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: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).  The molecular structure of the title compound showing 50% probability displacement ellipsoids. 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.