2-Anilino-N-methyl-N-phenylbenzamide

The title compound, C20H18N2O, is composed of three aromatic rings, the dihedral angles between the phenyl and benzamide rings, and between the benzamide and aniline rings being 59.86 (9) and 46.57 (10)°, respectively. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond involving the amino H atom and the benzamide carbonyl O atom. In the crystal structure, C—H⋯O and C—H⋯π interactions are present.


Comment
Aromatic amides have found extensive applications in preorganized rationally designed monomers for efficient molecular recognition and self-assembly (Brunsveld et al., 2001;Prins et al., 2001). Herein we report on the crystal structure of the title compound.
The molecular structure is stabilized by an intramolecular N-H···O hydrogen bond, involving the amino (N2) H-atom and the benzamide carbonyl O-atom (O1) ( Table 1). In the crystal structure symmetry related molecules are linked by a C-H···O interaction and there are also a number of C-H···π interactions present (Table 1).

Experimental
The title compound was prepared according to the reported procedure (Martín et al., 2006);Charton et al., 2006). Colourless single crystals, suitable for X-ray diffraction, were obtained by recrystallization from dichloromethane.

Refinement
In the final cycles of refinement, in the absence of significant anomalous scattering effects, 1609 Friedel pairs were merged and Δf'' set to zero. The amino H-atom was located in a difference Fourier map and freely refined [N-H = 0.85 (2)

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles 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 > 2sigma(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.