Cargando…
Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate
In the title compound, C(34)H(32)N(2)O(8), one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393998/ https://www.ncbi.nlm.nih.gov/pubmed/22798863 http://dx.doi.org/10.1107/S1600536812027341 |
_version_ | 1782237800027914240 |
---|---|
author | Sundaramoorthy, S. Rajesh, R. Raghunathan, R. Velmurugan, D. |
author_facet | Sundaramoorthy, S. Rajesh, R. Raghunathan, R. Velmurugan, D. |
author_sort | Sundaramoorthy, S. |
collection | PubMed |
description | In the title compound, C(34)H(32)N(2)O(8), one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached methoxyphenyl and phenoxy rings. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, generating an S(5) motif. In the crystal, molecules are linked into C(12) chains running along the a axis by C—H⋯O hydrogen bonds. The structure is further consolidated by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.7987 (14) Å]. |
format | Online Article Text |
id | pubmed-3393998 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33939982012-07-13 Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate Sundaramoorthy, S. Rajesh, R. Raghunathan, R. Velmurugan, D. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(34)H(32)N(2)O(8), one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached methoxyphenyl and phenoxy rings. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, generating an S(5) motif. In the crystal, molecules are linked into C(12) chains running along the a axis by C—H⋯O hydrogen bonds. The structure is further consolidated by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.7987 (14) Å]. International Union of Crystallography 2012-06-23 /pmc/articles/PMC3393998/ /pubmed/22798863 http://dx.doi.org/10.1107/S1600536812027341 Text en © Sundaramoorthy et al. 2012 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 Sundaramoorthy, S. Rajesh, R. Raghunathan, R. Velmurugan, D. Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title | Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title_full | Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title_fullStr | Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title_full_unstemmed | Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title_short | Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
title_sort | methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0(1,8).0(2,6).0(12,17)]octadeca-12(17),13,15-triene-8-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393998/ https://www.ncbi.nlm.nih.gov/pubmed/22798863 http://dx.doi.org/10.1107/S1600536812027341 |
work_keys_str_mv | AT sundaramoorthys methyl11hydroxy914methoxyphenyl4oxo3phenoxyazetidin2yl18oxo10oxa2azapentacyclo97001802601217octadeca12171315triene8carboxylate AT rajeshr methyl11hydroxy914methoxyphenyl4oxo3phenoxyazetidin2yl18oxo10oxa2azapentacyclo97001802601217octadeca12171315triene8carboxylate AT raghunathanr methyl11hydroxy914methoxyphenyl4oxo3phenoxyazetidin2yl18oxo10oxa2azapentacyclo97001802601217octadeca12171315triene8carboxylate AT velmurugand methyl11hydroxy914methoxyphenyl4oxo3phenoxyazetidin2yl18oxo10oxa2azapentacyclo97001802601217octadeca12171315triene8carboxylate |