Date Published: February 01, 2012
Publisher: International Union of Crystallography
Author(s): Yeong Keng Yoon, Mohamed Ashraf Ali, Tan Soo Choon, Safra Izuani Jama Asik, Ibrahim Abdul Razak.
The asymmetric unit of the title compound, C24H27N3O4, contains two molecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for molecule A and 51.40 (5) ° for molecule B. In both molecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H⋯O interactions link the molecules, generating  chains. The crystal packing also features weak π–π interactions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H⋯π interactions involving the benzene rings.
For the biological activity of benzimidazole derivatives, see: Spasov et al. (1999 ▶); Tanious et al. (2004) ▶; Townsend & Revankar (1970 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).