1-(2,3,4,5,6-Pentamethylbenzyl)-2-(pyridin-2-yl)-1H-benzimidazole

In the title compound, C24H25N3, the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the pyridine and benzene rings, respectively. An intramolecular C—H⋯N hydrogen bond is observed. In the crystal, molecules are stacked along the a axis by weak C—H⋯π interactions.

In the title compound, C 24 H 25 N 3 , the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å , and forms dihedral angles of 7.81 (5) and 87.61 (4) with the pyridine and benzene rings, respectively. An intramolecular C-HÁ Á ÁN hydrogen bond is observed. In the crystal, molecules are stacked along the a axis by weak C-HÁ Á Á interactions.
The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are in good agreement with those reported for related structures (Çelik et al., 2007; Çelik et al., 2009; Çelik et al., 2014). The benzimidazole ring system is substantially planar, the maximum deviation being 0.027 (2) Å for atom C8, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the mean planes through the pyridine (N1/C1-C5) and phenyl (C14-C19) rings, respectively.
An intramolecular C-H···N hydrogen bond is present (Table 1). In the crystal structure ( Fig. 2), molecules are stacked along the a axis by weak C-H···π hydrogen interactions (Table 1) involving the C7-C12 benzene ring of the benzimidazole moiety.

Refinement
All H atoms were placed geometrically and refined using a riding model approximation, with C-H = 0.93-0.97 Å, and with U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl H atoms. A rotating group model was applied to the methyl groups.  ORTEP-3 of the title compound, showing displacement ellipsoids drawn at 50% probability level.

Figure 2
The stacking of the title compound along the a axis with C-H···π type hydrogen-bond interactions (dashed lines).
Displacement ellipsoids are drawn at the 50% probability level.