2-[(2-Methoxybenzylidene)amino]phenol

In the title compound, C14H13NO2, the azomethine double bond adopts an E conformation and the benzene rings form a dihedral angle of 77.70 (7)°. In the crystal, molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds and arranged in a zigzag fashion, forming infinite chains parallel to the c axis, resulting in a graph-set R 2 2(9) motif.

In the title compound, C 14 H 13 NO 2 , the azomethine double bond adopts an E conformation and the benzene rings form a dihedral angle of 77.70 (7) . In the crystal, molecules are linked by O-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds and arranged in a zigzag fashion, forming infinite chains parallel to the c axis, resulting in a graph-set R 2 2 (9) motif.
In the title molecule ( Fig. 1), the azomethine (C═N, 1.2729 (18) Å) double bond adopts an E configuration. The bond lengths and angles in the title compound are similar to the corresponding bond lenghts and bond angles reported in a closely related compound, 2-(2,3,4-trimethoxy-6-methylbenzylideneamino)phenol (Liang et al., 2009). The crystal structure is stabilized by O2-H2A···N1 and C1-H1B···O1 intermolecular hydrogen bonds resulting in chains of molecules lying parallel to the c-axis in a zig zag fashion ( Fig. 2 and Tab. 1). The molecules lying about screw axis parallel to the c-axis form 9-membered rings due to hydrogen bonds in a motif with graph set R 2 2 (9) (Bernstein et al., 1995).

Experimental
A mixture of 2-methoxybenzaldehyde (0.01 mol, 1.36 g) and 2-aminophenol (0.01 mol, 1.09 g) in ethanol (50 ml) along with 3-4 drops of conc. H 2 SO 4 was refluxed for 3 h at 343 K. After cooling, the mixture was concentrated to one third of its volume under reduced pressure. The concentrated reaction mixture was kept at room temperature and light yellow crystals were obtained after five days. The crystalline product was collected, washed with methanol and dried to afford the title compound in 79% yield. Slow evaporation of a methanol solution afforded light yellow crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
The H atoms were positioned geometrically with C-H = 0.93 and 0.96 Å for aryl and methyl type H-atoms and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (aryl-C) or 1.5U eq (methyl-C). The H atom on the oxygen was located from a difference Fourier map and refined isotropically. A rotating group model was applied to the methyl group.

Computing details
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009     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.