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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...

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Autores principales: Zukerman-Schpector, Julio, Sugiyama, Fabricia H., Garcia, Ariel L. L., Correia, Carlos Roque D., Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
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.
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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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