Crystal structure of (2E)-1-(4-hy-droxy-1-methyl-2-oxo-1,2-di-hydro-quinolin-3-yl)-3-(4-hy-droxy-3-meth-oxy-phen-yl)prop-2-en-1-one

Peter Mangwala Kimpende; Ngoc Thanh Nguyen; Minh Thao Nguyen; Quoc Trung Vu; Luc Van Meervelt

doi:10.1107/S2056989015005630

Crystal structure of (2E)-1-(4-hy-droxy-1-methyl-2-oxo-1,2-di-hydro-quinolin-3-yl)-3-(4-hy-droxy-3-meth-oxy-phen-yl)prop-2-en-1-one

Acta Crystallogr E Crystallogr Commun. 2015 Mar 28;71(Pt 4):424-6. doi: 10.1107/S2056989015005630. eCollection 2015 Apr 1.

Authors

Peter Mangwala Kimpende¹, Ngoc Thanh Nguyen², Minh Thao Nguyen³, Quoc Trung Vu⁴, Luc Van Meervelt⁵

Affiliations

¹ Chemistry Department, University of Kinshasa, Kinshasa XI BP 190, Democratic Republic of Congo.
² Faculty of Chemical Technology, Hanoi University of Industry, Minh Khai Commune - Tu Liem District, Hanoi, Vietnam.
³ Faculty of Chemistry, Hanoi University of Science, 334 - Nguyen Trai - Thanh Xuan District, Hanoi, Vietnam.
⁴ Chemistry Department, Hanoi National University of Education, 136 - Xuan Thuy - Cau Giay, Hanoi, Vietnam.
⁵ Chemistry Department, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Heverlee), Belgium.

Abstract

In the title compound, C20H17NO5, the dihedral angle between the mean plane of the di-hydro-quinoline ring system (r.m.s. deviation = 0.003 Å) and the benzene ring is 1.83 (11)°. The almost planar conformation is a consequence of an intra-molecular O-H⋯O hydrogen bond and the E configuration about the central C=C bond. In the crystal structure, O-H⋯O hydrogen bonds generate chains of mol-ecules along the [10-1] direction. These chains are linked via π-π inter-actions [inter-centroid distances are in the range 3.6410 (16)-3.8663 (17) Å].

Keywords: 4-hydroxy-1,2-dihydroquinolin-2(1H)-one; crystal structure; hydrogen bonding; α,β-unsaturated ketones; π–π interactions.