4-[(E)-Phenyliminomethyl]benzonitrile

In the molecule of the title compound, C14H10N2, the two aromatic rings are oriented at a dihedral angle of 32.22 (6)°. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the molecules into centrosymmetric R 2 2(10) dimers. A weak π–π interaction between the cyanobenzene rings, with a centroid–centroid distance of 3.8447 (3) Å, further stabilizes the crystal structure. There is also a C—H⋯π interaction between the aniline ring and a CH group of the cyanobenzene ring.

In the molecule of the title compound, C 14 H 10 N 2 , the two aromatic rings are oriented at a dihedral angle of 32.22 (6) . In the crystal structure, intermolecular C-HÁ Á ÁN hydrogen bonds link the molecules into centrosymmetric R 2 2 (10) dimers. A weakinteraction between the cyanobenzene rings, with a centroid-centroid distance of 3.8447 (3) Å , further stabilizes the crystal structure. There is also a C-HÁ Á Á interaction between the aniline ring and a CH group of the cyanobenzene ring.

Comment
The crystal structures of p-halo-N-(p-cyanobenzylidene)-aniline and p-cyano-N-(p-halobenzylidene)aniline, (halo = bromo and chloro) (Ojala et al., 2002) have been reported, previously. The title compound, (I), differs due to no attachment of halogen atoms. It is prepared in aqueous medium and we report herein its crystal structure.
The molecule of (I), (Fig. 1), is a Schiff base ligand of aniline and p-cyanobenzaldehyde. The bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar, and they are oriented at a dihedral angle of 32.22 (6)°.

Experimental
The starting materials employed were first purified by distillation or crystallization just before use. The experiment was performed in stoppered flask at room temperature. The title compound was synthesized by using equimolecular mixture of aniline (5 mmol) and p-cyanobenzaldehyde (5 mmol) of pH = 9 in aqueous medium. The product was precipitated after a few minutes, and separated by filtration, washed with a small amount of water and dried for 2 d at room temperature in a vacuum desicator. The dried filtrate was used for X-ray analysis (yield; 53.09%, m.p. 339 K).

Refinement
H atoms were located in a difference syntheses and refined [C-H = 0.949 (15)-0.999 (12) Å and U iso (H) = 1.2U eq (C)]. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.