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1-[(2S*,4R*)-6-氟-2-甲基-1,2,3,4-四氢喹啉-4-基]吡咯烷-2-酮的晶体结构

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

作者信息

Pradeep P S, Naveen S, Kumara M N, Mahadevan K M, Lokanath N K

机构信息

Department of Chemistry, Kuvempu University, Jnanasahyadri, Shankaraghatta 577 451, India.

Institution of Excellence, University of Mysore, Manasagangotri, Mysore 570 006, India.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2014 Aug 30;70(Pt 9):153-6. doi: 10.1107/S1600536814019254. eCollection 2014 Sep 1.

Abstract

In the title compound, C14H17FN2O, the 1,2,3,4-tetra-hydro-pyridine ring of the quinoline moiety adopts a half-chair conformation, while the pyrrolidine ring has an envelope conformation with the central methyl-ene 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 substanti-ally 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, mol-ecules 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 inter-actions, forming a three-dimensional structure.

摘要

在标题化合物C₁₄H₁₇FN₂O中,喹啉部分的1,2,3,4-四氢吡啶环呈半椅式构象,而吡咯烷环呈信封式构象,以中心亚甲基C原子为折叶。吡咯烷环位于赤道平面,其平均平面与喹啉环系统的平均平面垂直,二面角值为88.37 (9)°。桥连的N-C键距离[1.349 (3) Å]明显短于共价半径之和(共价半径:C-N = 1.47 Å,C=N = 1.27 Å),这表明该键具有部分双键特征,导致一定程度的电荷离域。在晶体中,分子通过N-H⋯O和C-H⋯O氢键相连,形成平行于(10-1)的片层。这些二维网络通过C-H⋯F氢键和C-H⋯π相互作用相连,形成三维结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5ee5/4186090/563316e6de61/e-70-00153-fig1.jpg

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