Research Article: Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benz­imidazole-5-carboxyl­ate

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Yeong Keng Yoon, Mohamed Ashraf Ali, Ang Chee Wei, Safra Izuani Jama Asik, Ibrahim Abdul Razak.


In the title compound, C24H25N3O5, the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl­ene C atoms forming the flap. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal packing is further stabillized by weak π–π inter­actions between the benzene rings within the benzimidazole ring system [centroid–centroid distance = 3.7955 (7) Å]. A weak C—H⋯π inter­action involving the benzodioxole ring is also present.

Partial Text

For the pharmacological appplications of benzimidazole derivatives, see: Grassmann et al. (2002 ▶); Demirayak et al. (2002 ▶); Evans et al. (1997 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Yoon et al. (2012a ▶,b ▶,c ▶)