2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol

The molecule of the title compound, C15H14N2O2 is almost planar, the dihedral angle between the 6-methyl-1H-benzimidazole plane and the 2-methoxyphenol plane being 6.9 (2)°. An intramolecular O—H⋯N hydrogen bond is present. Adjacent molecules are linked by N—H⋯O hydrogen bonds into a three-dimensional network structure. The benzoimidazole methyl group and its attached C atom are positionally disordered in a 0.724 (4):0.276 (4) ratio.

The molecule of the title compound, C 15 H 14 N 2 O 2 is almost planar, the dihedral angle between the 6-methyl-1H-benzimidazole plane and the 2-methoxyphenol plane being 6.9 (2) . An intramolecular O-HÁ Á ÁN hydrogen bond is present. Adjacent molecules are linked by N-HÁ Á ÁO hydrogen bonds into a three-dimensional network structure. The benzoimidazole methyl group and its attached C atom are positionally disordered in a 0.724 (4):0.276 (4) ratio.

Comment
Imidazole and its derivatives are an important class of heterocycle with N-donor atoms, therefore they can be excellent organic ligands to generate various complexes (Huang et al., 2004). Benzimidazoles are privileged structural units not only in the pharmaceutical industry but also in several other fields such as agricultural, electronic, and polymer chemistry (Perry et al., 1993). We report here the synthesis and crystal structure of the title compound.

Experimental
A mixture of 4-methylbenzene-1,2-diamine (1 mmol) and 2-hydroxy-3-methoxybenzaldehyde (1 mmol) in ethanol (15 ml) was stirred for 8 h and then filtered. The resulting clear orange solution was vapor at room temperature for 7 d, after which orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained, yield 45%.

Refinement
The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C-H distances in the range of 0.93-0.96 Å and with U iso (H) = 1.2U eq (parent atom), or U iso (H) = 1.5U eq (C methyl ). The coordinates of the H atoms of the N-H and O-H groups were found from difference Fourier maps and were allowed for as riding atoms with O-H 0.82 Å and N-H 0.92 Å and with U iso (H) = 1.2U eq (O). Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Figures
2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol  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 Rfactors(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.