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(1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one
The title compound, C(32)H(23)ClN(2)O(4), has a quinoline, a chlorophenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two molecules of identical chirality in the asymmetric...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3239020/ https://www.ncbi.nlm.nih.gov/pubmed/22199868 http://dx.doi.org/10.1107/S1600536811048896 |
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author | Vennila, K. N. Sankaran, M. Mohan, P. S. Velmurugan, D. |
author_facet | Vennila, K. N. Sankaran, M. Mohan, P. S. Velmurugan, D. |
author_sort | Vennila, K. N. |
collection | PubMed |
description | The title compound, C(32)H(23)ClN(2)O(4), has a quinoline, a chlorophenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two molecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intramolecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R (2) (2)(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å(3)) within which there is no evidence of solvent molecules. |
format | Online Article Text |
id | pubmed-3239020 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32390202011-12-23 (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one Vennila, K. N. Sankaran, M. Mohan, P. S. Velmurugan, D. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(32)H(23)ClN(2)O(4), has a quinoline, a chlorophenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two molecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intramolecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R (2) (2)(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å(3)) within which there is no evidence of solvent molecules. International Union of Crystallography 2011-11-19 /pmc/articles/PMC3239020/ /pubmed/22199868 http://dx.doi.org/10.1107/S1600536811048896 Text en © Vennila et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Vennila, K. N. Sankaran, M. Mohan, P. S. Velmurugan, D. (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title | (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title_full | (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title_fullStr | (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title_full_unstemmed | (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title_short | (1R*,3′S*,4′R*)-4′-(4-Chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
title_sort | (1r*,3′s*,4′r*)-4′-(4-chlorophenyl)-3′-[(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)carbonyl]-1′-methylspiro[acenaphthylene-1,2′-pyrrolidin]-2-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3239020/ https://www.ncbi.nlm.nih.gov/pubmed/22199868 http://dx.doi.org/10.1107/S1600536811048896 |
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