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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...

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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/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.
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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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