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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...

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Autores principales: Pradeep, P. S., Naveen, S., Kumara, M. N., Mahadevan, K. M., Lokanath, N. K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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.
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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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