4-[1-(4-Cyano-benz-yl)-1H-benzimidazol-2-yl]benzonitrile

Abstract

In the title compound, C(22)H(14)N(4), a new substituted benzimidazole, three inter-molecular C-H⋯N inter-actions link neighbouring mol-ecules into different dimers with R(2) (2)(12), R(2) (2)(8) and R(2) (2)(24) ring motifs. A fourth C-H⋯N inter-action links neighbouring mol-ecules along the c axis. There is also a short inter-molecular contact between the azomethine (C=N) segment of the benzimidazole ring and one of the C atoms of a neighbouring benzene ring [N⋯C = 3.191 (5), C⋯C = 3.364 (6) Å], which links the mol-ecules along the a axis. The two cyano-benzene rings are almost perpendicular to each other, with an inter-planar angle of 87.70 (7)°. The dihedral angles between the mean planes of the benzimidazole ring and the two outer benzene rings are 36.27 (16) and 86.70 (16)°. In the crystal structure, mol-ecules are stacked down the a axis with centroid-centroid distances of 3.906 (2)-3.912 (2) Å and inter-planar distances of 3.5040 (17) and 3.6235 (17) Å.

Fig. 1.

The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.

Fig. 2.

The crystal packing of the title compound, viewed down the a-axis showing infinite stacks of molecules along the a-axis and also linking of molecules through C—H···N interactions along the c-axis. Intermolecular hydrogen bonds are shown as dashed lines.