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4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry
The title compound, C(23)H(24)N(2)O(9), is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C—C bond bearing the adjacent acetyloxy substituents. These are flanked on one side by a C-bound 4-methoxyphenyl group and on the other by a methylene...
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/PMC7336773/ https://www.ncbi.nlm.nih.gov/pubmed/32695456 http://dx.doi.org/10.1107/S2056989020007914 |
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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(23)H(24)N(2)O(9), is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C—C bond bearing the adjacent acetyloxy substituents. These are flanked on one side by a C-bound 4-methoxyphenyl group and on the other by a methylene group. The almost sp (2)-N atom [sum of angles = 357°] bears a 4-nitrobenzyloxycarbonyl substituent. In the crystal, ring-methylene-C—H⋯O(acetyloxy-carbonyl) and methylene-C—H⋯O(carbonyl) interactions lead to supramolecular layers lying parallel to ([Image: see text]01); the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces indicates the combined importance of H⋯H (42.3%), H⋯O/O⋯H (37.3%) and H⋯C/C⋯H (14.9%) surface contacts. Further, the interaction energies, largely dominated by the dispersive term, point to the stabilizing influence of H⋯H and O⋯O contacts in the inter-layer region. |
format | Online Article Text |
id | pubmed-7336773 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-73367732020-07-20 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: 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(23)H(24)N(2)O(9), is a tetra-substituted pyrrolidine derivative with a twisted conformation, with the twist evident in the C—C bond bearing the adjacent acetyloxy substituents. These are flanked on one side by a C-bound 4-methoxyphenyl group and on the other by a methylene group. The almost sp (2)-N atom [sum of angles = 357°] bears a 4-nitrobenzyloxycarbonyl substituent. In the crystal, ring-methylene-C—H⋯O(acetyloxy-carbonyl) and methylene-C—H⋯O(carbonyl) interactions lead to supramolecular layers lying parallel to ([Image: see text]01); the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces indicates the combined importance of H⋯H (42.3%), H⋯O/O⋯H (37.3%) and H⋯C/C⋯H (14.9%) surface contacts. Further, the interaction energies, largely dominated by the dispersive term, point to the stabilizing influence of H⋯H and O⋯O contacts in the inter-layer region. International Union of Crystallography 2020-06-16 /pmc/articles/PMC7336773/ /pubmed/32695456 http://dx.doi.org/10.1107/S2056989020007914 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. 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title | 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title_full | 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title_fullStr | 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title_full_unstemmed | 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title_short | 4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry |
title_sort | 4-nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, hirshfeld surface analysis and computational chemistry |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336773/ https://www.ncbi.nlm.nih.gov/pubmed/32695456 http://dx.doi.org/10.1107/S2056989020007914 |
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