2,2'-[1,5-Bis(4-amino-phen-yl)-1,5-dihydro-benzo[1,2-d;4,5-d']diimidazole-2,6-di-yl]diphenol

Abstract

The title mol-ecule, C(32)H(24)N(6)O(2), has a crystallographic inversion centre in the middle of the benzodiimidazole core. It exists as the enol-imine tautomeric form and exhibits a strong intra-molecular O-H⋯N hydrogen bond. The dihedral angles between the planes of the 2-hy-droxy-phenyl and 4-amino-phenyl substituents and the plane of the benzodiimidazole unit [12.69 (8) and 84.71 (8)°, respectively] differ significantly due to steric reasons. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming a two-dimensional network.

Fig. 1.

An ORTEPIII presentation of the molecule in a general orientation showing crystallographic numbering scheme. Anisotropic thermal ellipsoids are pictured with 30% of probability level.

Fig. 2.

Two symmetry related molecules of (I), one in x, y, z and the another one in –x + 1, –y – 1, –z (i) position, showing spatial relationship between primary amino group N3 with C12-to-C17 aromatic ring.

Fig. 3.

The projection down b-shows the orientation of symmetry related molecules in (000) and (001) planes, towards those in (001/2) plane.