2-Bromo-5-tert-butyl-N-methyl-N-[2-(methyl-amino)-phen-yl]-3-(1-methyl-1H-benzimidazol-2-yl)benzamide

Abstract

In the title compound, C27H29BrN4O, benzimidazole ring system and the amide moiety are planar [r.m.s. deviations = 0.016 (2) and 0.017 (1) Å, respectively]. The mol-ecule adopts a conformation in which the amide linkage is almost perpendicular to the central ring [dihedral angle = 85.79 (8)°], while the benzimidazole ring system makes a dihedral angle of 70.26 (11)° with the central ring. In the crystal, the mol-ecules form dimers through N-H⋯O hydrogen bonds and C-H⋯O interactions. These dimers are further linked into zigzag ribbons along [201] by weak C-H⋯Br inter-actions. As a result of the bulky nature of the mol-ecule, as evidenced by the large dihedral angles between rings, there is little evidence for any π-π inter-actions.

Keywords: crystal structure.

Fig. 1.

The structures of 1 and 2.

Fig. 2.

The molecular structure of C27H29BrN4O, showing the atom numbering scheme and 30% probability displacement ellipsoids and the linking of the molecules into dimers by N—H···O hydrogen bonds (shown as dashed bonds).

Fig. 3.

The molecular packing for C27H29BrN4O viewed along the b axis showing linking of the hydrogen bonded dimers into zigzag chains in the [2 0 1] direction by C—H···Br interactions (N—H···O and C—H···Br interactions shown as dashed bonds).