1-Isopropyl-4-nitro-6-meth-oxy-1H-benzimidazole

Abstract

There are two independent mol-ecules in the asymmetric unit of the title compound, C(11)H(13)N(3)O(3). The inter-planar angles for the two rings of the benzimidazole ring system is 2.21 (12)° in one mol-ecule and 0.72 (12)° in the other. The nitro group is twisted in the same direction relative to the least-squares plane through its attached benzene ring in both mol-ecules, with inter-planar angles of 15.22 (9) and 18.02 (8)°. In the crystal structure, mol-ecules are stacked along the a axis through π-π inter-actions (centroid-centroid distance 4.1954 Å). C-H⋯O hydrogen bonds are also present.

Fig. 1.

The molecular structure of the title compound, shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Fig. 2.

A packing diagram of (I) showing the π-π stacking interactions along the a axis between the benzimidazole rings (dashed line).

Fig. 3.

The molecular synthesis scheme used to produce the title compound (3). The following were also used: a: (NH4)2S,EtOH; b: formic acid, acetone, THF; c: conc. HCl, formic acid.