Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers: supramolecular assembly in one and two dimensions mediated by hydrogen bonding and π–π stacking

Acta Crystallographica Section E: Crystallographic Communications

Jerry P. Jasinski¹  Sean P. Millikan¹  Hemmige S. Yathirajan²  Tholappanavara H. Suresha Kumara³  Haliwana B. V. Sowmya³  Nagendrappa Gopalpur³  Christopher Glidewell⁴ 

[1] Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA;Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India;PG Department of Chemistry, Jain University, 52 Bellary Road, Hebbal, Bangalore 560 024, India;School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland;

关键词: crystal structure;    2-chloroquinolines;    molecular conformation;    hydrogen bonding;    π–π stacking interactions;   

DOI  :  10.1107/S2056989015008233

来源: DOAJ

【 摘 要 】

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 π–π 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 π–π stacking interaction. In (III), three of the four independent molecules are linked by π–π 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 π–π 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.

【 授权许可】

Unknown