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Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate
The title compound, C(15)H(19)NO(4), is the a product of the esterification of the corresponding carbonic acid with methanol. The molecule comprises a fused tetracyclic system containing three five-membered rings (2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647423/ https://www.ncbi.nlm.nih.gov/pubmed/26594446 http://dx.doi.org/10.1107/S2056989015016679 |
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author | Toze, Flavien A. A. Poplevin, Dmitry S. Zubkov, Fedor I. Nikitina, Eugeniya V. Porras, Ciara Khrustalev, Victor N. |
author_facet | Toze, Flavien A. A. Poplevin, Dmitry S. Zubkov, Fedor I. Nikitina, Eugeniya V. Porras, Ciara Khrustalev, Victor N. |
author_sort | Toze, Flavien A. A. |
collection | PubMed |
description | The title compound, C(15)H(19)NO(4), is the a product of the esterification of the corresponding carbonic acid with methanol. The molecule comprises a fused tetracyclic system containing three five-membered rings (2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (azepane). The five-membered rings have the usual envelope conformations, with the quaternary C atom being the flap atom for the 2-pyrrolidinone ring, and the ether O atom being the common flap atom for the remaining rings. The seven-membered azepane ring adopts a chair conformation with the methine and middle methylene C atoms lying above and below the mean plane defined by the remaining five atoms. The carboxylate substituent is rotated by 77.56 (5)° with respect to the base plane of the tetrahydrofuran ring. In the crystal, the molecules are bound by weak C—H⋯O hydrogen-bonding interactions into puckered layers parallel to (001). |
format | Online Article Text |
id | pubmed-4647423 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-46474232015-11-20 Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate Toze, Flavien A. A. Poplevin, Dmitry S. Zubkov, Fedor I. Nikitina, Eugeniya V. Porras, Ciara Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(15)H(19)NO(4), is the a product of the esterification of the corresponding carbonic acid with methanol. The molecule comprises a fused tetracyclic system containing three five-membered rings (2-pyrrolidinone, tetrahydrofuran and dihydrofuran) and one seven-membered ring (azepane). The five-membered rings have the usual envelope conformations, with the quaternary C atom being the flap atom for the 2-pyrrolidinone ring, and the ether O atom being the common flap atom for the remaining rings. The seven-membered azepane ring adopts a chair conformation with the methine and middle methylene C atoms lying above and below the mean plane defined by the remaining five atoms. The carboxylate substituent is rotated by 77.56 (5)° with respect to the base plane of the tetrahydrofuran ring. In the crystal, the molecules are bound by weak C—H⋯O hydrogen-bonding interactions into puckered layers parallel to (001). International Union of Crystallography 2015-09-12 /pmc/articles/PMC4647423/ /pubmed/26594446 http://dx.doi.org/10.1107/S2056989015016679 Text en © Toze et al. 2015 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 | Data Reports Toze, Flavien A. A. Poplevin, Dmitry S. Zubkov, Fedor I. Nikitina, Eugeniya V. Porras, Ciara Khrustalev, Victor N. Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title | Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title_full | Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title_fullStr | Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title_full_unstemmed | Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title_short | Crystal structure of methyl (3RS,4SR,4aRS,11aRS,11bSR)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
title_sort | crystal structure of methyl (3rs,4sr,4ars,11ars,11bsr)-5-oxo-3,4,4a,5,7,8,9,10,11,11a-decahydro-3,11b-epoxyazepino[2,1-a]isoindole-4-carboxylate |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647423/ https://www.ncbi.nlm.nih.gov/pubmed/26594446 http://dx.doi.org/10.1107/S2056989015016679 |
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