Peña-Solórzano Diana, König Burkhard, Sierra Cesar A, Ochoa-Puentes Cristian
Grupo de Investigación en Macromoléculas, Departamento de Química, Universidad, Nacional de Colombia-Sede Bogotá, Carrera 45 # 26-85, A.A. 5997, Bogotá, Colombia.
Institute of Organic Chemistry, University of Regensburg, 93040-Regensburg, Germany.
Acta Crystallogr E Crystallogr Commun. 2017 May 5;73(Pt 6):804-808. doi: 10.1107/S2056989017006272. eCollection 2017 Jun 1.
In the title compounds, -(5-acetyl-2-methyl-phen-yl)quinoline-2-carboxamide [CHNO, (I)], -(5-acetyl-2-bromo-phen-yl)quinoline-2-carboxamide [CHBrNO, (II)] and -(5-acetyl-2-ethynylphen-yl)quinoline-2-carboxamide [CHNO, (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68 (5) (I), 5.59 (7) (II) and 1.87 (6)° (III) with the acetyl-substituted ring. The mol-ecular structures of (I) and (III) each feature an intra-molecular N-H⋯N hydrogen bond, forming an (5) ring, while in (II) an intra-molecular bifurcated N-H⋯(N,Br) hydrogen bond forms two (5) rings. In the crystals, weak C-H⋯O hydrogen bonds link mol-ecules of (I) into (7) chains long [010], mol-ecules of (II) into chains of (8) rings along [110] and mol-ecules of (III) into (8) chains along [010]. In (I), there are no significant π-π stacking inter-actions under 4 Å, but in both (II) and (III), π-π inter-actions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid-centroid disttances of 3.748 (1) Å in (II) and 3.577 (1), 3.784 (1) and 3.780 (1) Å in (III)].
在标题化合物中，即α-(5-乙酰基-2-甲基苯基)喹啉-2-甲酰胺[C₁₉H₁₆N₂O₂，(I)]、α-(5-乙酰基-2-溴苯基)喹啉-2-甲酰胺[C₁₉H₁₅BrN₂O₂，(II)]和α-(5-乙酰基-2-乙炔基苯基)喹啉-2-甲酰胺[C₂₀H₁₆N₂O₂，(III)]中，喹啉环系基本呈平面状，与乙酰基取代环形成的二面角分别为3.68 ( 5)°(I)、5.59 (7)°(II)和1.87 (6)°(III)。(I)和(III)的分子结构均具有分子内N-H⋯N氢键，形成一个五元环，而在(II)中，分子内分叉的N-H⋯(N,Br)氢键形成两个五元环。在晶体中，弱的C-H⋯O氢键将(I)的分子连接成长度为[010]方向的七元链，将(II)的分子沿[110]方向连接成八元环链，将(III)的分子沿[010]方向连接成八元链。在(I)中，4 Å范围内不存在显著的π-π堆积相互作用，但在(II)和(III)中，π-π相互作用将弱氢键链连接成平行于(001)的层[在(II)中质心-质心距离为3.748 (1) Å，在(III)中为3.577 (1)、3.784 (1)和3.780 (1) Å]。
