(2E)-3-[4-(1H-Benzimidazol-2-ylmethoxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one

In the title compound, C24H20N2O3, the mean plane of the benzimidazole unit makes dihedral angles of 79.88 (11) and 85.44 (12)° with the benzene and 4-methoxybenzene rings, respectively. The benzene and 4-methoxybenzene rings maske a dihedral angle of 16.10 (14)°. A pair of intermolecular N—H⋯O hydrogen bonds connects adjacent molecules into an inversion dimer, generating an R 2 2(26) ring motif. The crystal structure is further stabilized by C—H⋯π interactions.

In the title compound, C 24 H 20 N 2 O 3 , the mean plane of the benzimidazole unit makes dihedral angles of 79.88 (11) and 85.44 (12) with the benzene and 4-methoxybenzene rings, respectively. The benzene and 4-methoxybenzene rings maske a dihedral angle of 16.10 (14) . A pair of intermolecular N-HÁ Á ÁO hydrogen bonds connects adjacent molecules into an inversion dimer, generating an R 2 2 (26) ring motif. The crystal structure is further stabilized by C-HÁ Á Á interactions.   Table 1 Hydrogen-bond geometry (Å , ).
(2E)-3-[4-(1H-Benzimidazol-2-ylmethoxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one M. Akkurt, Z. Baktir, S. Samshuddin, B. Narayana and H. S. Yathirajan Comment The benzimidazole ring system and its related compounds play an important role in pharmaceutical and agricultural fields due to their broad spectrum of biological activities (Pujar et al., 1988, Bouwman et al., 1990. The synthesis of novel benzimidazole derivatives remains a main focus of medicinal research. Benzimidazoles are also useful as insecticides, acaricides, nematocides, herbicides and other plant-protective agents in the field of pest control (Madkour et al., 2006). In recent years, attention has increasingly been given to the synthesis of benzimidazole derivatives as a source of new antimicrobial agents.
In addition, benzimidazole derivatives have played a crucial role in the theoretical development of heterocyclic chemistry and are also used extensively in organic synthesis. Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. Chalcones are highly reactive substances of varied nature. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999;Satyanarayana et al., 2004). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006).
The crystal structures of some benzimidazole derivatives viz., 2-chloromethyl-1H-benzimidazole nitrate (Jian et al., 2003) and 5-methoxy-1H-benzo[d]imidazole-2(3H)-thione (Odabaşoğlu et al., 2007) have been reported. In continuation of our work on the synthesis of benzimidazole derivatives (Jasinski et al., 2010) and in view of the importance of benzimidazoles, the title compound (I) is synthesized and its crystal structure is reported here.
The benzene and 4-methoxybenzene rings form a dihedral angle of 16.10 (14)° with each other.

Experimental
A mixture of a 4-(1H-benzimidazol-2-ylmethoxy)benzaldehyde (2.52 g, 0.01 mole) and p-methoxy acetophenone (1.5 g, 0.01 mole) in 50 ml ethanolic sodium hydroxide was stirred at 278-283 K for 3 h, then maintained at room temperature for 24 h and poured into ice cold water. The precipitate that appeared after neutralization with dilute HCl was filtered off and recystallized from 1,4-dioxane. The single crystals were grown from DMF by slow evaporation method and yield of the compound was 75% (m.p.: 521 K). with U iso (H) = 1.2U eq (C,N) for amine, methylene and aromatic H atoms or 1.5U eq (C) for methyl H atoms. Fig. 1. The molecular structure and numbering scheme for the title compound (I). Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.