Date Published: May 01, 2011
Publisher: International Union of Crystallography
Author(s): Liping Meng, James C. Fettinger, Mark J. Kurth.
The title molecule, C22H23N3O2, was obtained via an intramolecular cycloaddition of an azomethine ylide and an alkene tethered by a benzimidazole unit. The benzoimidazole unit is essentially planar, with an r.m.s. deviation of 0.0087 Å from the nine constituent atoms. It has a cis fusion of the two pyrrolidine rings as well as a cis ester appendage. The two pyrrolidine rings rings have envelope conformations. The crystal packing is stabilized by aromatic π–π stacking of parallel benzimidazole ring systems, with a centroid-to-centroid distance of 3.518 (6) Å. Weak intermolecular C—H⋯O contacts may also play a role in the stability of the packing.
Polycyclic nitrogen-containing heterocycles form the basic skeleton of numerous alkaloids and physiologically active compounds, see: Southon & Buckingham (1989 ▶). Conformational studies have been reported for related pyrrolidino[3,4-b]pyrrolidine-2-carboxylates obtained from intramolecular cycloaddition of azomethine ylides, see: Cheng et al. (2001 ▶); Meng et al. (2007 ▶). For related literature on the pharmaceutical properties of benzimidazole and pyrrolidine, see: Gudmundsson et al. (2000 ▶); Hamilton & Steiner (1997 ▶). For related literature on the azomethine ylide cycloaddition in similar systems, Pedrosa et al. (2006 ▶); Yang et al. (2006 ▶).