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

The title mol­ecule, C(22)H(23)N(3)O(2), 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...

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Detalles Bibliográficos
Autores principales: Meng, Liping, Fettinger, James C., Kurth, Mark J.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089295/
https://www.ncbi.nlm.nih.gov/pubmed/21754512
http://dx.doi.org/10.1107/S1600536811014292
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author Meng, Liping
Fettinger, James C.
Kurth, Mark J.
author_facet Meng, Liping
Fettinger, James C.
Kurth, Mark J.
author_sort Meng, Liping
collection PubMed
description The title mol­ecule, C(22)H(23)N(3)O(2), 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.
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spelling pubmed-30892952011-07-13 Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate Meng, Liping Fettinger, James C. Kurth, Mark J. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(22)H(23)N(3)O(2), 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. International Union of Crystallography 2011-04-29 /pmc/articles/PMC3089295/ /pubmed/21754512 http://dx.doi.org/10.1107/S1600536811014292 Text en © Meng et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Meng, Liping
Fettinger, James C.
Kurth, Mark J.
Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title_full Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title_fullStr Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title_full_unstemmed Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title_short Ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
title_sort ethyl 1-benzyl-1,2,3,3a,4,10b-hexa­hydro­pyrrolo­[2′,3′:3,4]pyrrolo­[1,2-a]benzimidazole-2-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089295/
https://www.ncbi.nlm.nih.gov/pubmed/21754512
http://dx.doi.org/10.1107/S1600536811014292
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