Crystal structures of five (2-chloro-quinolin-3-yl)methyl ethers : supra-molecular assembly in one and two dimensions mediated by hydrogen bonding and π-π stacking
Date
06/2015Author
Keywords
Metadata
Show full item recordAltmetrics Handle Statistics
Altmetrics DOI Statistics
Abstract
In the molecules of the title compounds, methyl 5-bromo-2-[(2-chloroquinolin-3-yl)methoxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methylquinolin-3-yl)methoxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methylquinolin-3-yl)methoxy]benzoate, C19H16ClNO3, (III), which crystallizes with Z' = 4 in space group P212121, and 2-chloro-3-[(naphthalen-1-yloxy)methyl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloroquinolin-3-yl)methoxy]-4-(hydroxymethyl)-6-methylpyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The molecules of (I) are linked by two independent [pi]-[pi] stacking interactions to form chains, but there are no hydrogen bonds present in the structure. In (II), the molecules are weakly linked into chains by a single type of [pi]-[pi] stacking interaction. In (III), three of the four independent molecules are linked by [pi]-[pi] stacking interactions but the other molecule does not participate in such interactions. Weak C-H...O hydrogen bonds link the molecules into three types of chains, two of which contain just one type of independent molecule while the third type of chain contains two types of molecule. The molecules of (IV) are linked into chains by a C-H...π(arene) hydrogen bond, but [pi]-[pi] stacking interactions are absent. In (V), there is an intramolecular O-H...O hydrogen bond, and molecules are linked into sheets by a combination of O-H...N hydrogen bonds and π-π stacking interactions.
Citation
Sowmya , H B V , Suresha Kumara , T H , Gopalpur , N , Jasinski , J P , Millikan , S P , Yathirajan , H S & Glidewell , C 2015 , ' Crystal structures of five (2-chloro-quinolin-3-yl)methyl ethers : supra-molecular assembly in one and two dimensions mediated by hydrogen bonding and π-π stacking ' , Acta Crystallographica Section E: Crystallographic Communications , vol. 71 , no. 6 , pp. 609-17 . https://doi.org/10.1107/S2056989015008233
Publication
Acta Crystallographica Section E: Crystallographic Communications
Status
Peer reviewed
ISSN
2056-9890Type
Journal article
Rights
Copyright 2015 the Authors. Published under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0/uk/legalcode), which permits unrestricted use, provided the original author and source are credited.
Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.