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Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis
The title compound, C(14)H(17)NO(4), features an epoxide-O atom fused to a pyrrolidyl ring, the latter having an envelope conformation with the N atom being the flap. The 4-methoxyphenyl group is orthogonal to [dihedral angle = 85.02 (6)°] and lies to the opposite side of the five-membered ring to...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5598852/ https://www.ncbi.nlm.nih.gov/pubmed/28932440 http://dx.doi.org/10.1107/S2056989017009987 |
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author | Zukerman-Schpector, Julio Sugiyama, Fabricia H. Garcia, Ariel L. L. Correia, Carlos Roque D. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_facet | Zukerman-Schpector, Julio Sugiyama, Fabricia H. Garcia, Ariel L. L. Correia, Carlos Roque D. Jotani, Mukesh M. Tiekink, Edward R. T. |
author_sort | Zukerman-Schpector, Julio |
collection | PubMed |
description | The title compound, C(14)H(17)NO(4), features an epoxide-O atom fused to a pyrrolidyl ring, the latter having an envelope conformation with the N atom being the flap. The 4-methoxyphenyl group is orthogonal to [dihedral angle = 85.02 (6)°] and lies to the opposite side of the five-membered ring to the epoxide O atom, while the N-bound ethyl ester group (r.m.s. deviation of the five fitted atoms = 0.0187 Å) is twisted with respect to the ring [dihedral angle = 17.23 (9)°]. The most prominent interactions in the crystal are of the type methine-C—H⋯O(carbonyl) and these lead to the formation of linear supramolecular chains along the c axis; weak benzene-C—H⋯O(epoxide) and methine-C—H⋯O(methoxy) interactions connect these into a three-dimensional architecture. The analysis of the Hirshfeld surface confirms the presence of C—H⋯O interactions in the crystal, but also the dominance of H⋯H dispersion contacts. |
format | Online Article Text |
id | pubmed-5598852 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-55988522017-09-20 Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis Zukerman-Schpector, Julio Sugiyama, Fabricia H. Garcia, Ariel L. L. Correia, Carlos Roque D. Jotani, Mukesh M. Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(14)H(17)NO(4), features an epoxide-O atom fused to a pyrrolidyl ring, the latter having an envelope conformation with the N atom being the flap. The 4-methoxyphenyl group is orthogonal to [dihedral angle = 85.02 (6)°] and lies to the opposite side of the five-membered ring to the epoxide O atom, while the N-bound ethyl ester group (r.m.s. deviation of the five fitted atoms = 0.0187 Å) is twisted with respect to the ring [dihedral angle = 17.23 (9)°]. The most prominent interactions in the crystal are of the type methine-C—H⋯O(carbonyl) and these lead to the formation of linear supramolecular chains along the c axis; weak benzene-C—H⋯O(epoxide) and methine-C—H⋯O(methoxy) interactions connect these into a three-dimensional architecture. The analysis of the Hirshfeld surface confirms the presence of C—H⋯O interactions in the crystal, but also the dominance of H⋯H dispersion contacts. International Union of Crystallography 2017-07-21 /pmc/articles/PMC5598852/ /pubmed/28932440 http://dx.doi.org/10.1107/S2056989017009987 Text en © Zukerman-Schpector et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Zukerman-Schpector, Julio Sugiyama, Fabricia H. Garcia, Ariel L. L. Correia, Carlos Roque D. Jotani, Mukesh M. Tiekink, Edward R. T. Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title | Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title_full | Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title_fullStr | Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title_full_unstemmed | Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title_short | Ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and Hirshfeld analysis |
title_sort | ethyl 2-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate: crystal structure and hirshfeld analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5598852/ https://www.ncbi.nlm.nih.gov/pubmed/28932440 http://dx.doi.org/10.1107/S2056989017009987 |
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