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

In the mol­ecules of the title compounds, methyl 5-bromo-2-[(2-chloro­quinolin-3-yl)meth­oxy]benzoate, C(18)H(13)BrClNO(3), (I), methyl 5-bromo-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C(19)H(15)BrClNO(3), (II), methyl 2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, C(19)H(16)ClNO(3), (III), which crystallizes with Z′ = 4 in space group P2(1)2(1)2(1), and 2-chloro-3-[(naphthalen-1-yl­oxy)meth­yl]quinoline, C(20)H(14)ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloro­quinolin-3-yl)meth­oxy]-4-(hy­droxy­meth­yl)-6-methyl­pyridin-3-yl}methanol, C(18)H(17)ClN(2)O(3), (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.