1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry
The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme torsion angle is 38.26 (15)° [m = methylcarboxylate, a = acetyloxy and me = methylene]. While the N-bound ethylcarboxylate group occupi...
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International Union of Crystallography
2020
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my.sunway.eprints.12972020-10-07T07:03:30Z http://eprints.sunway.edu.my/1297/ 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, A. L. Kwong, Huey Chong * Tiekink, Edward R. T. * QD Chemistry The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme 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 2020-05-24 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1297/1/Tiekink%20Acta%20Cryst%202020%20E76%20967.pdf Dallasta Pedroso, Sofia and Caracelli, Ignez and Zukerman-Schpector, Julio and Soto-Monsalve, Monica and De Almeida Santos, Regina H. and Correia, Carlos Roque D. and Llanes Garcia, A. L. and Kwong, Huey Chong * and Tiekink, Edward R. T. * (2020) 1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry. Acta Crystallographica Section E Crystallographic Communications, 76 (6). pp. 967-972. ISSN 2056-9890 http://doi.org/10.1107/S205698902000701X doi:10.1107/S205698902000701X |
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QD Chemistry Dallasta Pedroso, Sofia Caracelli, Ignez Zukerman-Schpector, Julio Soto-Monsalve, Monica De Almeida Santos, Regina H. Correia, Carlos Roque D. Llanes Garcia, A. 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 |
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The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme 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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Article |
author |
Dallasta Pedroso, Sofia Caracelli, Ignez Zukerman-Schpector, Julio Soto-Monsalve, Monica De Almeida Santos, Regina H. Correia, Carlos Roque D. Llanes Garcia, A. 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, A. L. Kwong, Huey Chong * Tiekink, Edward R. T. * |
author_sort |
Dallasta Pedroso, Sofia |
title |
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_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_sort |
1-ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, hirshfeld surface analysis and computational chemistry |
publisher |
International Union of Crystallography |
publishDate |
2020 |
url |
http://eprints.sunway.edu.my/1297/1/Tiekink%20Acta%20Cryst%202020%20E76%20967.pdf http://eprints.sunway.edu.my/1297/ http://doi.org/10.1107/S205698902000701X |
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1680323425052131328 |
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13.18916 |