3-Anilino-N-p-tolylbenzamide

The title compound, C20H18N2O, which crystallizes with two independent molecules (A and B) in the asymmetric unit, is composed of three aromatic rings (I, II and III). The conformation of the two independent molecules is slightly different. The dihedral angles between the central aromatic ring II and rings I and III are 47.13 (9) and 89.36 (9)°, respectively, for molecule A, and 29.60 (9) and 70.72 (9)°, respectively, for molecule B. Rings I and III are inclined to one another by 86.57 (9)° in molecule A, and 64.59 (10)° in molecule B. The molecular structures are stabilized by intramolecular N—H⋯O hydrogen bonds. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains propagating in the [010] direction. In addition, a number of C—H⋯π interactions are observed.


Comment
In the past decade, the assessment of new hydrogen bonding patterns has received great attention due to their potential applications in biological, materials and supramolecular sciences, and crystal engineering. Here we report on the crystal structure of the title compound, a phenyl-amino-benzamide.
The molecular structure of the two independent molecules (A and B) of the title compound are illustrated in Fig. 1. The bond lengths and angles are within normal ranges. The conformation of the two independent molecules is slightly different.
In the crystal structure molecules are linked through N-H···O intermolecular hydrogen bonds, involving the benzamide carbonyl O-atom (O1 and O1') and the 4-methyl-Benzenamine amino H-atoms (H2'N and H2N) of the other molecule (Table   1), so forming chains propagating in direction [010]. In addition a number of C-H···π interactions are observed (Table 1).

Experimental
The title compound was prepared according to the reported procedures (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 absence of significant anomalous dispersion effects, the Friedel pairs were merged. H atoms were placed in calculated positions, with N-H = 0.88-0.93 Å and C-H = 0.95 Å, and refined in riding mode, with U iso (H) = 1.2U eq (c,N).