2-(1H-Benzimidazol-2-yl)-4,6-dichloro-phenol

Abstract

The title compound, C(13)H(8)Cl(2)N(2)O, was prepared by the reaction of 3,5-dichloro-2-hy-droxy-benzaldehyde with 1,2-diamino-benzene in methanol at ambient temperature. The title mol-ecule is essentially planar, the mean deviation from the plane of the non-H atoms being 0.037 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule. In the crystal, symmetry-related mol-ecules are linked through N-H⋯O hydrogen bonds, forming polymeric chains propagating in [001]. The chains are linked by π-π inter-actions involving the dichloro-phenol ring and the benzoimidazole ring system [centroid-centroid distances = 3.535 (2) and 3.724 (2) Å].

Fig. 1.

The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular O-H···N hydrogen bond is shown as a dashed line.

Fig. 2.

The crystal packing of the title compound, viewed along the b-axis. The O-H···N and N-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).