N-(2,3-Dimethylphenyl)-2-methylbenzamide

In the title compound, C16H17NO, the two aromatic rings make a dihedral angle of 5.9 (2)°, while the central amide core –NH—C(=O)– is twisted by 44.0 (3) and 47.1 (3)° out of the planes of the 2,3-dimethylphenyl and 2-methylphenyl rings, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains running along the b axis.

In the title compound, C 16 H 17 NO, the two aromatic rings make a dihedral angle of 5.9 (2) , while the central amide core -NH-C( O)-is twisted by 44.0 (3) and 47.1 (3) out of the planes of the 2,3-dimethylphenyl and 2-methylphenyl rings, respectively. In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into infinite chains running along the b axis.
Further, the ortho-methyl group in the benzoyl ring is positioned syn to the C=O bond and so also the ortho-and metamethyl groups in the anilino ring to the N-H bond, while the N-H and C=O bonds in the C-NH-C(O)-C segment are anti to each other.
In the crystal structure, intermolecular N-H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.

Experimental
The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Plate like colourless single crystals of the title compound were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement
All hydrogen atoms except amide H atom were placed in calculated positions with C-H distances in the range 0.93-0.96 Å and constrained to ride on their parent atoms. The amide H atom was found in a difference map and was refined with the N-H distance restrained to 0.86 (3) Å. The Uĩso~(H) values were set at 1.2U eq (C-aromatic, N) or 1.5U eq (C-methyl). In the absence of significant anomalous scattering, the absolute structure could not be reliably determined and then the Friedel pairs were merged and any references to the Flack parameter were removed.