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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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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. |
format | Online Article Text |
id | pubmed-7273984 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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