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Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
In the title compound, C(14)H(17)FN(2)O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its m...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186090/ https://www.ncbi.nlm.nih.gov/pubmed/25309166 http://dx.doi.org/10.1107/S1600536814019254 |
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author | Pradeep, P. S. Naveen, S. Kumara, M. N. Mahadevan, K. M. Lokanath, N. K. |
author_facet | Pradeep, P. S. Naveen, S. Kumara, M. N. Mahadevan, K. M. Lokanath, N. K. |
author_sort | Pradeep, P. S. |
collection | PubMed |
description | In the title compound, C(14)H(17)FN(2)O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N—C bond distance [1.349 (3) Å] is substantially shorter than the sum of the covalent radii (d (cov): C—N = 1.47 Å and C=N = 1.27 Å), which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming sheets lying parallel to (10-1). These two-dimensional networks are linked via C—H⋯F hydrogen bonds and C—H⋯π interactions, forming a three-dimensional structure. |
format | Online Article Text |
id | pubmed-4186090 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-41860902014-10-12 Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one Pradeep, P. S. Naveen, S. Kumara, M. N. Mahadevan, K. M. Lokanath, N. K. Acta Crystallogr Sect E Struct Rep Online Research Communications In the title compound, C(14)H(17)FN(2)O, the 1,2,3,4-tetrahydropyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methylene C atom as the flap. The pyrrolidine ring lies in the equatorial plane and its mean plane is normal to the mean plane of the quinoline ring system, with a dihedral angle value of 88.37 (9)°. The bridging N—C bond distance [1.349 (3) Å] is substantially shorter than the sum of the covalent radii (d (cov): C—N = 1.47 Å and C=N = 1.27 Å), which indicates partial double-bond character for this bond, resulting in a certain degree of charge delocalization. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming sheets lying parallel to (10-1). These two-dimensional networks are linked via C—H⋯F hydrogen bonds and C—H⋯π interactions, forming a three-dimensional structure. International Union of Crystallography 2014-08-30 /pmc/articles/PMC4186090/ /pubmed/25309166 http://dx.doi.org/10.1107/S1600536814019254 Text en © Pradeep et al. 2014 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 | Research Communications Pradeep, P. S. Naveen, S. Kumara, M. N. Mahadevan, K. M. Lokanath, N. K. Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title | Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title_full | Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title_fullStr | Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title_full_unstemmed | Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title_short | Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
title_sort | crystal structure of 1-[(2s*,4r*)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186090/ https://www.ncbi.nlm.nih.gov/pubmed/25309166 http://dx.doi.org/10.1107/S1600536814019254 |
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