3-Methyl-N-(2-methylphenyl)benzamide

The molecular structure of the title compound, C15H15NO, involves an intramolecular C—H⋯O hydrogen bond. The central amide group –NH—C(=O)– is twisted by 37.95 (12)° out of the meta-substituted benzoyl ring and by 37.88 (12)° out of the ortho-substituted aniline ring. The two benzene rings are inclined to one another at only 4.2 (1)° having an interplanar spacing of ca 0.90 Å. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into chains running along the b axis. A weak intermolecular C—H⋯π interaction is also present.

The molecular structure of the title compound, C 15 H 15 NO, involves an intramolecular C-HÁ Á ÁO hydrogen bond. The central amide group -NH-C( O)-is twisted by 37.95 (12) out of the meta-substituted benzoyl ring and by 37.88 (12) out of the ortho-substituted aniline ring. The two benzene rings are inclined to one another at only 4.2 (1) having an interplanar spacing of ca 0.90 Å . The crystal structure is stabilized by intermolecular N-HÁ Á ÁO hydrogen bonds, which link the molecules into chains running along the b axis. A weak intermolecular C-HÁ Á Á interaction is also present.
MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2033).

Comment
As part of a study of the substituent effects on the crystal structures of benzanilides (Bowes et al., 2003;Gowda et al., 2008a,b;Rodrigues et al., 2010), in the present work, the structure of N-(2-methylphenyl)-3-methylbenzamide (I) has been determined ( Fig. 1). In the crystal, the ortho-methyl substituent on the anilino ring is positioned syn to the N-H bond, while the meta-methyl substituent on the benzoyl ring is positioned anti to the carbonyl C==O bond.
The structure of (I) involves an intramolecular C-H···O hydrogen bond (Table 1)  hydrogen bond is also present in the structure, and occurs between the C14 methyl group and the centroid Cg1(i) of the C1-C6 ring at the position (i): x, y -1, z (Table 1).

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. Rod-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement
All H atoms were visible in difference maps and then treated as riding atoms with C-H = 0.93 or 0.96 Å, N-H = 0.86 Å and O-H = 0.90 Å. The U iso (H) values were set at 1.2U eq (C aromatic, N) and 1.5U eq (C methyl, O). The U values of the bonded atoms C7 and O1 have been subject (using the DELU instruction) to a rigid bond restraint, thus enforcing their anisotropic displacement components in the direction of the bond to be equal within a standard deviation of 0.005.