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

In the molecules of the title compounds, methyl 5-bromo-2-(2-chloroquinolin3- yl) methoxy] benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-(2-chloro-6methylquinolin- 3-yl) methoxy] benzoate, C19H15BrClNO3, (II), methyl 2-(2chloro-6-methylquinolin-3-yl) methoxy] benzoate, C19H16ClNO3, (III), which crystallizes with Z0 = 4 in space group P2(1)2(1)2(1), and 2-chloro-3-(naphthalen-1yl-oxy) 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 center dot center dot center dot 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 center dot center dot center dot O (arene) hydrogen bond, but pi-pi stacking interactions are absent. In (V), there is an intramolecular O-H center dot center dot center dot O hydrogen bond, and molecules are linked into sheets by a combination of OH center dot center dot center dot N hydrogen bonds and pi-pi stacking interactions