(E)-3-(2-Hydroxy-4-methoxybenzylideneamino)benzonitrile

In the molecule of the title compound, C15H12N2O2, the aromatic rings are oriented at a dihedral angle of 28.11 (3)°. Intramolecular O—H⋯N hydrogen bonding results in the formation of a planar six-membered ring, which is nearly coplanar with the adjacent ring at a dihedral angle of 1.53 (3)°. In the crystal structure, π–π contacts between the benzene rings [centroid–centroid distance = 3.841 (1) Å] may stabilize the structure.

In the molecule of the title compound, C 15 H 12 N 2 O 2 , the aromatic rings are oriented at a dihedral angle of 28.11 (3) . Intramolecular O-HÁ Á ÁN hydrogen bonding results in the formation of a planar six-membered ring, which is nearly coplanar with the adjacent ring at a dihedral angle of 1.53 (3) . In the crystal structure,contacts between the benzene rings [centroid-centroid distance = 3.841 (1) Å ] may stabilize the structure.

D-HÁ
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2714). Comment Schiff base compounds have received considerable attention for many years, primarily due to their importance in the development of coordination chemistry related to magnetism (Weber et al., 2007), catalysis (Chen et al., 2008) and biological process (May et al., 2004). Our group is interested in the syntheses and preparation of Schiff bases. We report herein the synthesis and crystal structure of the title compound.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges.  (Table 1) results in the formation of a planar six-membered ring C (O1/N1/C1/C2/C8/H1B), which is oriented with respect to rings A and B at dihedral angles of A/C = 1.53 (3) and B/C = 27.66 (3) °. So, rings A and C are nearly coplanar.

Experimental
For the preparation of the title compound, 3-aminobenzonitrile (472 mg, 4 mmol) and 2-hydroxy-4-methoxybenzaldehyde (608 mg, 4 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 5 h, and then cooled to room temperature. The solution was filtered and after two weeks, yellow crystals suitable for X-ray analysis were obtained (yield; 85%).

Refinement
H atom (for OH) was located in difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.