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Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate

In the title compound, C(27)H(33)NO(5), a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system carries an ethyl acetate substituent on the acridine N atom and an o-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridin...

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Autores principales: Allah, Omyma A. A. Abd, Kaur, Manpreet, Akkurt, Mehmet, Mohamed, Shaaban K., Jasinski, Jerry P., Elgarhy, Sahar M. I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061104/
https://www.ncbi.nlm.nih.gov/pubmed/33953945
http://dx.doi.org/10.1107/S2056989021001341
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author Allah, Omyma A. A. Abd
Kaur, Manpreet
Akkurt, Mehmet
Mohamed, Shaaban K.
Jasinski, Jerry P.
Elgarhy, Sahar M. I.
author_facet Allah, Omyma A. A. Abd
Kaur, Manpreet
Akkurt, Mehmet
Mohamed, Shaaban K.
Jasinski, Jerry P.
Elgarhy, Sahar M. I.
author_sort Allah, Omyma A. A. Abd
collection PubMed
description In the title compound, C(27)H(33)NO(5), a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system carries an ethyl acetate substituent on the acridine N atom and an o-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 80.45 (7)° and this conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. The ester C=O oxygen atom is disordered over major and minor orientations in a 0.777 (9):0.223 (9) ratio and the terminal –CH(3) unit of the ethyl side chain is disordered over two sets of sites in a 0.725 (5): 0.275 (5) ratio. In the crystal, C—H⋯O hydrogen bonds combine to link the mol­ecules into a three-dimensional network. van der Waals H⋯H contacts contribute the most to the Hirshfeld surface (66.9%) followed by O⋯H/H⋯O (22.1%) contacts associated with weak hydrogen bonds.
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spelling pubmed-80611042021-05-04 Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate Allah, Omyma A. A. Abd Kaur, Manpreet Akkurt, Mehmet Mohamed, Shaaban K. Jasinski, Jerry P. Elgarhy, Sahar M. I. Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(27)H(33)NO(5), a 3,3,6,6-tetra­methyl­tetra­hydro­acridine-1,8-dione ring system carries an ethyl acetate substituent on the acridine N atom and an o-hy­droxy­phenyl ring on the central methine C atom of the di­hydro­pyridine ring. The benzene ring is inclined to the acridine ring system at an angle of 80.45 (7)° and this conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond between the hy­droxy substituent on the benzene ring and one of the carbonyl groups of the acridinedione unit. The ester C=O oxygen atom is disordered over major and minor orientations in a 0.777 (9):0.223 (9) ratio and the terminal –CH(3) unit of the ethyl side chain is disordered over two sets of sites in a 0.725 (5): 0.275 (5) ratio. In the crystal, C—H⋯O hydrogen bonds combine to link the mol­ecules into a three-dimensional network. van der Waals H⋯H contacts contribute the most to the Hirshfeld surface (66.9%) followed by O⋯H/H⋯O (22.1%) contacts associated with weak hydrogen bonds. International Union of Crystallography 2021-02-12 /pmc/articles/PMC8061104/ /pubmed/33953945 http://dx.doi.org/10.1107/S2056989021001341 Text en © Allah et al. 2021 https://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.
spellingShingle Research Communications
Allah, Omyma A. A. Abd
Kaur, Manpreet
Akkurt, Mehmet
Mohamed, Shaaban K.
Jasinski, Jerry P.
Elgarhy, Sahar M. I.
Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title_full Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title_fullStr Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title_short Crystal structure and Hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
title_sort crystal structure and hirshfeld surface analysis of ethyl 2-[9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,8-dioxo-2,3,4,4a,5,6,7,8a,9,9a,10,10a-dodeca­hydro­acridin-10-yl]acetate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061104/
https://www.ncbi.nlm.nih.gov/pubmed/33953945
http://dx.doi.org/10.1107/S2056989021001341
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