N-(2,4-Dimethylphenyl)-2-methylbenzamide

In the title compound, C16H17NO, the N—H bond is in an anti conformation with respect to the C=O bonds. The aniline and benzoyl rings are almost coplanar, making a dihedral angle of 4.9 (3)°. The plane of the amide group makes an angle of 61.3 (3)° with the aniline ring and 58.3 (3)° with the benzoyl ring. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds into chains running along the b axis.

In the title compound, C 16 H 17 NO, the N-H bond is in an anti conformation with respect to the C O bonds. The aniline and benzoyl rings are almost coplanar, making a dihedral angle of 4.9 (3) . The plane of the amide group makes an angle of 61.3 (3) with the aniline ring and 58.3 (3) with the benzoyl ring. In the crystal, the molecules are linked by N-HÁ Á ÁO hydrogen bonds into chains running along the b axis.

Comment
In the present work, as part of our study of substituent effects on the structures of benzanilides (Gowda et al., 2003;2008a, b, c), the structure of 2-methyl-N-(2,4-dimethylphenyl)benzamide has been determined. The N-H and C=O bonds in the amide segment are anti to each other ( Fig. 1 (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. Plate-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement
H atoms attached to C atoms were placed in calculated positions and refined within a riding model with C-H distances of 0.93 or 0.96 Å. The coordinates of the H atom of the amide group were refined with a restraint of 0.86 (2)Å for the H-N distance. The U iso (H) values were set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (C methyl ).

Special details
Experimental. CrysAlis RED (Oxford Diffraction, 2008). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 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 Rfactors(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.