Ethyl 1-benzyl-1,2,3,3a,4,10b-hexahydropyrrolo[2′,3′: 3,4] pyrrolo[1,2-a]-benzimidazole-2-carboxylate

Liping Meng; James C. Fettinger; Mark J. Kurth

doi:10.1107/S1600536811014292

Ethyl 1-benzyl-1,2,3,3a,4,10b-hexahydropyrrolo[2′,3′: 3,4] pyrrolo[1,2-a]-benzimidazole-2-carboxylate

Liping Meng, James C. Fettinger, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article

Abstract

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-tocentroid distance of 3.518 (6) Å. Weak intermolecular C-H⋯O contacts may also play a role in the stability of the packing.

Original language	English (US)
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	67
Issue number	5
DOIs	https://doi.org/10.1107/S1600536811014292
State	Published - May 2011

ASJC Scopus subject areas

Condensed Matter Physics
Materials Science(all)
Chemistry(all)

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Meng, L., Fettinger, J. C., & Kurth, M. J. (2011). Ethyl 1-benzyl-1,2,3,3a,4,10b-hexahydropyrrolo[2′,3′: 3,4] pyrrolo[1,2-a]-benzimidazole-2-carboxylate. Acta Crystallographica Section E: Structure Reports Online, 67(5). https://doi.org/10.1107/S1600536811014292

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abstract = "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 {\AA} 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-tocentroid distance of 3.518 (6) {\AA}. Weak intermolecular C-H⋯O contacts may also play a role in the stability of the packing.",

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T1 - Ethyl 1-benzyl-1,2,3,3a,4,10b-hexahydropyrrolo[2′,3′

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AU - Fettinger, James C.

AU - Kurth, Mark J.

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AB - 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-tocentroid distance of 3.518 (6) Å. Weak intermolecular C-H⋯O contacts may also play a role in the stability of the packing.

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