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1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry

The title compound, C(13)H(19)NO(8), is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the C(m)—C(a)—C(a)—C(me) torsion angle is 38.26 (15)° [m = methyl­carboxyl­ate, a = acet­yloxy and me = methyl­ene]. While the N-bound ethyl­carboxyl­at...

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Autores principales: Dallasta Pedroso, Sofia, Caracelli, Ignez, Zukerman-Schpector, Julio, Soto-Monsalve, Monica, De Almeida Santos, Regina H., Correia, Carlos Roque D., Llanes Garcia, Ariel L., Kwong, Huey Chong, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7273984/
https://www.ncbi.nlm.nih.gov/pubmed/32523774
http://dx.doi.org/10.1107/S205698902000701X
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author Dallasta Pedroso, Sofia
Caracelli, Ignez
Zukerman-Schpector, Julio
Soto-Monsalve, Monica
De Almeida Santos, Regina H.
Correia, Carlos Roque D.
Llanes Garcia, Ariel L.
Kwong, Huey Chong
Tiekink, Edward R. T.
author_facet Dallasta Pedroso, Sofia
Caracelli, Ignez
Zukerman-Schpector, Julio
Soto-Monsalve, Monica
De Almeida Santos, Regina H.
Correia, Carlos Roque D.
Llanes Garcia, Ariel L.
Kwong, Huey Chong
Tiekink, Edward R. T.
author_sort Dallasta Pedroso, Sofia
collection PubMed
description The title compound, C(13)H(19)NO(8), is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the C(m)—C(a)—C(a)—C(me) torsion angle is 38.26 (15)° [m = methyl­carboxyl­ate, a = acet­yloxy and me = methyl­ene]. While the N-bound ethyl­carboxyl­ate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supra­molecular double-layers are formed by weak methyl- and methyl­ene-C—H⋯O(carbon­yl) inter­actions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional inter­actions between them. The Hirshfeld surface is dominated by H⋯H (55.7%) and H⋯C/C⋯H (37.0%) contacts; H⋯H contacts are noted in the inter-double-layer region. The inter­action energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.
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spelling pubmed-72739842020-06-09 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry Dallasta Pedroso, Sofia Caracelli, Ignez Zukerman-Schpector, Julio Soto-Monsalve, Monica De Almeida Santos, Regina H. Correia, Carlos Roque D. Llanes Garcia, Ariel L. Kwong, Huey Chong Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(13)H(19)NO(8), is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the C(m)—C(a)—C(a)—C(me) torsion angle is 38.26 (15)° [m = methyl­carboxyl­ate, a = acet­yloxy and me = methyl­ene]. While the N-bound ethyl­carboxyl­ate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supra­molecular double-layers are formed by weak methyl- and methyl­ene-C—H⋯O(carbon­yl) inter­actions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional inter­actions between them. The Hirshfeld surface is dominated by H⋯H (55.7%) and H⋯C/C⋯H (37.0%) contacts; H⋯H contacts are noted in the inter-double-layer region. The inter­action energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal. International Union of Crystallography 2020-05-29 /pmc/articles/PMC7273984/ /pubmed/32523774 http://dx.doi.org/10.1107/S205698902000701X Text en © Dallasta Pedroso et al. 2020 http://creativecommons.org/licenses/by/4.0/ 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/4.0/
spellingShingle Research Communications
Dallasta Pedroso, Sofia
Caracelli, Ignez
Zukerman-Schpector, Julio
Soto-Monsalve, Monica
De Almeida Santos, Regina H.
Correia, Carlos Roque D.
Llanes Garcia, Ariel L.
Kwong, Huey Chong
Tiekink, Edward R. T.
1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title_full 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title_fullStr 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title_full_unstemmed 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title_short 1-Ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry
title_sort 1-ethyl 2-methyl 3,4-bis­(acet­yloxy)pyrrolidine-1,2-di­carboxyl­ate: crystal structure, hirshfeld surface analysis and computational chemistry
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7273984/
https://www.ncbi.nlm.nih.gov/pubmed/32523774
http://dx.doi.org/10.1107/S205698902000701X
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