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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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Detalles Bibliográficos
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
Descripción
Sumario: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.