N-(3,5-Dimethylphenyl)-2-methylbenzamide

In the molecular structure of the title compound, C16H17NO, the amide group is twisted by 41.8 (2) and 29.0 (2)° out of the planes of the 2-methylphenyl and 3,5-dimethylphenyl rings, respectively. The two aromatic rings make a dihedral angle of 69.5 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds connect the molecules into C(4) chains running along the c axis.

In the molecular structure of the title compound, C 16 H 17 NO, the amide group is twisted by 41.8 (2) and 29.0 (2) out of the planes of the 2-methylphenyl and 3,5-dimethylphenyl rings, respectively. The two aromatic rings make a dihedral angle of 69.5 (1) . In the crystal, intermolecular N-HÁ Á ÁO hydrogen bonds connect the molecules into C(4) chains running along the c axis.
In the molecule, the amido group is twisted 41.8 (2)° and 29.0 (2)° out of the planes of the 2-methylphenyl and the 3,5-dimethylphenyl rings, respectively. The two aromatic rings make the dihedral angle of 69.5 (1)°. Intermolecular N-H···O hydrogen bonds (Table 1) connect the molecules into chains running along the c-axis (Fig. 2).

Experimental
Compound (I) as prepared according to the method described by Gowda, Foro et al. (2008b). Colourless blocks of (I) were obtained by slow evaporation from an ethanol solution (0.5 g in about 25 ml of ethanol) held at room temperature.

Refinement
All hydrogen atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å and N-H = 0.86 Å. The U iso (H) values were set at 1.2U eq (C-aromatic, N) and 1.5U eq (C-methyl). The methyl groups with the carbon atoms C14, C15 and C16 exhibit orientational disorder in the positions of their H atoms, and each group was modelled by two sets of methyl hydrogen atoms. The refined occupancies are 0.82 (3) and 0.18 (3) for the C14-mehtyl group, 0.60 (3) and 0.40 (3) for the C15 group, 0.73 (2) and 0.27 (2) for the C16 group. Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 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.  (7) 0.0014 (7) 0.0078 (6) 0.0008 (6)