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Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate

The title com­pound, C(24)H(24)N(2)O(6), consists of ethyl 2-(1,2,3,4-tetra­hydro-2-oxo­quinolin-1-yl)acetate and 4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbomoyl] units, where the oxo­quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal,...

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Autores principales: Filali Baba, Yassir, Hayani, Sonia, Hökelek, Tuncer, Kaur, Manpreet, Jasinski, Jerry, Sebbar, Nada Kheira, Kandri Rodi, Youssef
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829727/
https://www.ncbi.nlm.nih.gov/pubmed/31709103
http://dx.doi.org/10.1107/S2056989019014154
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author Filali Baba, Yassir
Hayani, Sonia
Hökelek, Tuncer
Kaur, Manpreet
Jasinski, Jerry
Sebbar, Nada Kheira
Kandri Rodi, Youssef
author_facet Filali Baba, Yassir
Hayani, Sonia
Hökelek, Tuncer
Kaur, Manpreet
Jasinski, Jerry
Sebbar, Nada Kheira
Kandri Rodi, Youssef
author_sort Filali Baba, Yassir
collection PubMed
description The title com­pound, C(24)H(24)N(2)O(6), consists of ethyl 2-(1,2,3,4-tetra­hydro-2-oxo­quinolin-1-yl)acetate and 4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbomoyl] units, where the oxo­quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—H(Oxqn)⋯O(Ethx) and C—H(Ph­yl)⋯O(Carbx) (Oxqn = oxoquinolin, Ethx = eth­oxy, Phyl = phenyl and Carbx = carboxyl­ate) weak hydrogen bonds link the mol­ecules into a three-dimensional network sturucture. A π–π inter­action between the constituent rings of the oxo­quinoline unit, with a centroid–centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (53.9%), H⋯O/O⋯H (28.5%) and H⋯C/C⋯H (11.8%) inter­actions. Weak inter­molecular hydrogen-bond inter­actions and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com­pared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO mol­ecular orbital behaviour was elucidated to determine the energy gap.
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spelling pubmed-68297272019-11-08 Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate Filali Baba, Yassir Hayani, Sonia Hökelek, Tuncer Kaur, Manpreet Jasinski, Jerry Sebbar, Nada Kheira Kandri Rodi, Youssef Acta Crystallogr E Crystallogr Commun Research Communications The title com­pound, C(24)H(24)N(2)O(6), consists of ethyl 2-(1,2,3,4-tetra­hydro-2-oxo­quinolin-1-yl)acetate and 4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbomoyl] units, where the oxo­quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—H(Oxqn)⋯O(Ethx) and C—H(Ph­yl)⋯O(Carbx) (Oxqn = oxoquinolin, Ethx = eth­oxy, Phyl = phenyl and Carbx = carboxyl­ate) weak hydrogen bonds link the mol­ecules into a three-dimensional network sturucture. A π–π inter­action between the constituent rings of the oxo­quinoline unit, with a centroid–centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (53.9%), H⋯O/O⋯H (28.5%) and H⋯C/C⋯H (11.8%) inter­actions. Weak inter­molecular hydrogen-bond inter­actions and van der Waals inter­actions are the dominant inter­actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com­pared with the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO mol­ecular orbital behaviour was elucidated to determine the energy gap. International Union of Crystallography 2019-10-29 /pmc/articles/PMC6829727/ /pubmed/31709103 http://dx.doi.org/10.1107/S2056989019014154 Text en © Filali Baba et al. 2019 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
Filali Baba, Yassir
Hayani, Sonia
Hökelek, Tuncer
Kaur, Manpreet
Jasinski, Jerry
Sebbar, Nada Kheira
Kandri Rodi, Youssef
Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title_full Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title_fullStr Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title_full_unstemmed Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title_short Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
title_sort crystal structure, hirshfeld surface analysis and dft studies of ethyl 2-{4-[(2-eth­oxy-2-oxoeth­yl)(phen­yl)carbamo­yl]-2-oxo-1,2-di­hydro­quinolin-1-yl}acetate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829727/
https://www.ncbi.nlm.nih.gov/pubmed/31709103
http://dx.doi.org/10.1107/S2056989019014154
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