Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetra­hydro­quinolin-4-yl]pyrrolidin-2-one

Pradeep, P. S. and Naveen, S. and Kumara, M. N. and Mahadevan, K. M. and Lokanath, N. K. (2014) Crystal structure of 1-[(2S*,4R*)-6-fluoro-2-methyl-1,2,3,4-tetra­hydro­quinolin-4-yl]pyrrolidin-2-one. Acta Crystallographica Section E: Structure Reports Online, 70 (9). pp. 153-156. ISSN 1600-5368

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In the title compound, C14H17FN2O, 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 (dcov: 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...[pi] inter­actions, forming a three-dimensional structure.

Item Type: Article
Additional Information: Unmapped bibliographic data: JA - Acta Cryst. E [Field not mapped to EPrints] JO - Acta Crystallographica Section E [Field not mapped to EPrints]
Uncontrolled Keywords: crystal structure, tetrahydroquinoline, pyrrolidine, chirality
Subjects: Physical Sciences > Chemistry
Physical Sciences > Physics
Divisions: Constituent Colleges > Yuvaraja's College Mysore > Chemistry
PG Campuses > Manasagangotri, Mysore > Physics
Depositing User: Praveen Kumari B.L
Date Deposited: 04 Apr 2015 05:16
Last Modified: 04 Apr 2015 05:16

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