1-[2-(3,4-Dichlorobenzyloxy)-2-phenylethyl]-1H-benzimidazole

In the molecule of the title compound, C22H18Cl2N2O, the planar benzimidazole ring system is oriented with respect to the phenyl and dichlorobenzene rings at dihedral angles of 12.73 (3) and 36.57 (4)°, respectively. The dihedral angle between the dichlorobenzene and phenyl rings is 29.95 (6)°. There are C—H⋯π contacts between the benzimidazole and dichlorobenzene rings, between the benzimidazole and phenyl rings, and between a methylene group and the dichlorobenzene ring.

In the molecule of the title compound, C 22 H 18 Cl 2 N 2 O, the planar benzimidazole ring system is oriented with respect to the phenyl and dichlorobenzene rings at dihedral angles of 12.73 (3) and 36.57 (4) , respectively. The dihedral angle between the dichlorobenzene and phenyl rings is 29.95 (6) . There are C-HÁ Á Á contacts between the benzimidazole and dichlorobenzene rings, between the benzimidazole and phenyl rings, and between a methylene group and the dichlorobenzene ring.

Comment
In recent years, there has been increasing interest in synthesis of heterocyclic compounds having biological and commercial importances. Clotrimazole (Song & Shin, 1998), econazole (Freer et al., 1986), ketoconazole (Peeters et al., 1979a and miconazole (Peeters et al., 1979b) are well known imidazole ring containing, while itraconazole (Peeters et al., 1996) and fluconazole (Caira et al., 2004) are 1H-1,2,4-triazole ring containing, azole derivatives. They have been developed for clinical uses as antifungal agents (Brammer & Feczko, 1988). Lately, similar structures to miconazole and econazole have been reported to show antibacterial activity more than antifungal activity (Özel Güven et al., 2007a,b). In these structures, benzimidazole ring has been found in place of the imidazole ring of miconazole and econazole. Recently, we reported the crystal structures of furyl and fluorobenzene substituted compounds (Özel Güven et al., 2008a,b), and we report herein the crystal structure of title benzimidazole derivative.
In the molecule of the title compound ( Fig. 1) the bond lengths and angles are generally within normal ranges. The planar benzimidazole ring system is oriented with respect to the phenyl and dichlorobenzene rings at dihedral angles of 12.73 (3)°a nd 36.57 (4)°, respectively. Atoms C8, C9 and C16 are -0.125 (2), 0.062 (2) and 0.076 (2) Å away from the ring planes of the corresponding benzimidazole, phenyl and dichlorobenzene, respectively. So, they are nearly coplanar with the adjacent rings. The dichlorobenzene ring is oriented with respect to the phenyl ring at a dihedral angle of 29.95 (6)°.
In the crystal structure, the molecules are elongated along [101], and stacked along the b axis. The C-H···π contacts (Table 1) between the benzimidazole and the dichlorobenzene rings, the benzimidazole and the phenyl rings and the dichlorobenzene ring and the methylene group may stabilize the structure.

Experimental
The title compound was synthesized by the reaction of 2-(1H-benzimidazol-1-yl) -1-phenylethanol (Özel Güven et al., 2007a) with NaH and appropriate benzyl halide. To the solution of alcohol (300 mg, 1.259 mmol) in DMF (2.4 ml) was added NaH (63 mg, 1.574 mmol) in small fractions. The appropriate benzyl halide (238 mg, 1.259 mmol) in DMF (1.2 ml) was added dropwise. The mixture was stirred at room temperature for 2 h, and excess hydride was decomposed with a small amount of methyl alcohol. After evaporation to dryness under reduced pressure, the crude residue was suspended with water and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude residue was purified by chromatography on a silica-gel column using chloroform-methanol as eluent.
Crystals suitable for X-ray analysis were obtained by the recrystallization of the ether from a mixture of hexane/ethyl acetate (1:2) (yield; 229 mg, 46%).