Crystal structure of (2E)-1-(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

被引:0
作者
Kimpende, Peter Mangwala [1 ]
Ngoc Thanh Nguyen [2 ]
Minh Thao Nguyen [3 ]
Quoc Trung Vu [4 ]
Van Meervelt, Luc [5 ]
机构
[1] Univ Kinshasa, Dept Chem, Kinshasa, DEM REP CONGO
[2] Hanoi Univ Ind, Fac Chem Technol, Hanoi, Vietnam
[3] Hanoi Univ Sci, Fac Chem, Hanoi, Vietnam
[4] Hanoi Natl Univ Educ, Fac Chem, Hanoi, Vietnam
[5] Katholieke Univ Leuven, Dept Chem, Celestijnenlaan 200F, B-3001 Heverlee, Belgium
关键词
crystal structure; 4-hydroxy-1,2-dihydroquinolin-2(1H)-one; alpha; beta-unsaturated ketones; hydrogen bonding; pi-pi interactions;
D O I
10.1107/S2056989015005630
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title compound, C20H17NO5, the dihedral angle between the mean plane of the dihydroquinoline ring system (r.m.s. deviation = 0.003 angstrom) and the benzene ring is 1.83 (11)degrees. The almost planar conformation is a consequence of an intramolecular O-H center dot center dot center dot O hydrogen bond and the E configuration about the central C=C bond. In the crystal structure, O-H center dot center dot center dot O hydrogen bonds generate chains of molecules along the [10 (1) over bar] direction. These chains are linked via pi-pi interactions [inter-centroid distances are in the range 3.6410 (16)-3.8663 (17) angstrom].
引用
收藏
页码:424 / +
页数:8
相关论文
共 18 条
[1]   Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito [J].
Billker, O ;
Lindo, V ;
Panico, M ;
Etienne, AE ;
Paxton, T ;
Dell, A ;
Rogers, M ;
Sinden, RE ;
Morris, HR .
NATURE, 1998, 392 (6673) :289-292
[2]  
Bruker, 2003, SADABS SAINT SMART
[3]   Synthesis and antibacterial evaluation of certain quinolone derivatives [J].
Chen, YL ;
Fang, KC ;
Sheu, JY ;
Hsu, SL ;
Tzeng, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377
[4]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341
[5]   Synthesis of quinolinyl chalcones and evaluation of their antimalarial activity [J].
Domínguez, JN ;
Charris, JE ;
Lobo, G ;
de Domínguez, NG ;
Moreno, MM ;
Riggione, F ;
Sanchez, E ;
Olson, J ;
Rosenthal, PJ .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (06) :555-560
[6]   Quinolines as potent 5-lipoxygenase inhibitors:: Synthesis and biological profile of L-746,530 [J].
Dubé, D ;
Blouin, M ;
Brideau, C ;
Chan, CC ;
Desmarais, S ;
Ethier, D ;
Falgueyret, JP ;
Friesen, RW ;
Girard, M ;
Girard, Y ;
Guay, J ;
Riendeau, D ;
Tagari, P ;
Young, RN .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (10) :1255-1260
[7]   The Cambridge Structural Database in Retrospect and Prospect [J].
Groom, Colin R. ;
Allen, Frank H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) :662-671
[8]  
Hasegawa S., 1990, CHEM ABSTR, V114
[9]   SYNTHESES OF 3-ACYL-4-HYDROXY-2(1H)QUINOLONES [J].
KAPPE, T ;
AIGNER, R ;
HOHENGASSNER, P ;
STADLBAUER, W .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1994, 336 (07) :596-601
[10]  
Katritzky A.R., 1984, COMPREHENSIVE HETERO, P25