2-Chloro-N-(2,6-dimethylphenyl)benzamide

In the title compound, C15H14ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains running along the a axis.

In the title compound, C 15 H 14 ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18) . In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into chains running along the a axis.
In the title compound, one of the ortho-methyl groups in the aniline ring is positioned syn to the N-H bond, while the other ortho-methyl group is positioned anti to the N-H bond, the latter and the C=O bond being anti to each other.
In the crystal structure, intermolecular N1-H1···O1 hydrogen bonds (Table 1) link the molecules into infinite chains running along the a-axis. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared by a method similar to the one described by Gowda et al. (2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.
Rod like colourless single crystals of the title compound used in the X-ray diffraction studies were obtained by slow evaporation of the solvent from its ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement
Hydrogen atoms were placed in calculated positions with C-H distances of 0.93 Å (C-aromatic), 0.96 Å (C-methyl) and constrained to ride on their parent atoms. The amide H atom was visible in a difference map and refined with the N-H distance restrained to 0.86 (1) Å. The U iso (H) values were set at 1.2U eq (C-aromatic, N) or 1.5U eq (C-methyl).

Special details
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.