N-(3-Methylphenyl)benzamide

The asymmetric unit of the title compound, C14H13NO, contains four molecules, which are linked through N—H⋯O hydrogen bonds into two symmetry-independent chains running parallel to [001] and [101]. The N—H and C=O bonds of the amide groups are trans oriented in all four molecules. The molecules are not planar and both aromatic rings are twisted strongly relative to the plane of the amide group. The dihedral angle between the two benzene rings ranges from 70.6 (2) to 74.2 (2)°. The N—H bond is anti to the meta-methyl substituent in the aniline fragment in three of the four symmetry-independent molecules. In the fourth molecule, the aniline unit is disordered over two nearly coplanar positions; the anti and syn conformers occupy the same site in the crystal with equal probability.

The asymmetric unit of the title compound, C 14 H 13 NO, contains four molecules, which are linked through N-HÁ Á ÁO hydrogen bonds into two symmetry-independent chains running parallel to [001] and [101]. The N-H and C O bonds of the amide groups are trans oriented in all four molecules. The molecules are not planar and both aromatic rings are twisted strongly relative to the plane of the amide group. The dihedral angle between the two benzene rings ranges from 70.6 (2) to 74.2 (2) . The N-H bond is anti to the meta-methyl substituent in the aniline fragment in three of the four symmetry-independent molecules. In the fourth molecule, the aniline unit is disordered over two nearly coplanar positions; the anti and syn conformers occupy the same site in the crystal with equal probability.

S2. Experimental
The title compound was prepared according to the literature method (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. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

S3. Refinement
In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf" terms were set to zero.
The amide H atoms were located in difference Fourier map but in the refinement process the N-H bond lengths wereas restrained to 0.86 (3) Å. For the other H atoms idealized geometry was assumed and they were refined using a riding model with C-H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (U iso (NH) = 1.2, U iso (CH) = 1.2 and U iso (CH 3 ) = 1.5 U eq of the parent atom).
The benzene ring C29-C34 and the methyl group C42 are disordered over two nearly co-planar positions. The corresponding bond distances in the disordered groups were restrained to be equal. The site-occupancy factors were initially refined for the two positions of the methylphenyl fragment but they converged close to 0.5 and therefore the occupancy of the two positions was assumed to be equal 0.5. The U ij values of the disordered atoms and those of C45 and C46 were restrained by ISOR instruction to approximate isotropic behaviour supporting information sup-2 . E64, o2247

Figure 2
The molecular packing of the title compound, with hydrogen bonds shown as dashed lines. For clarity, the disordered components and the H atoms not involved in hydrogen bonding have been omitted.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
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