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

Haliwana B V Sowmya, Tholappanavara H Suresha Kumara, Nagendrappa Gopalpur, Jerry P Jasinski, Sean P Millikan, Hemmige S Yathirajan, Christopher Glidewell

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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.

Original languageEnglish
Pages (from-to)609-17
Number of pages9
JournalActa Crystallographica Section E: Crystallographic Communications
Volume71
Issue number6
DOIs
Publication statusPublished - Jun 2015

Keywords

  • Crystal structure
  • 2-chloro­quinolines
  • Mol­ecular conformation
  • Hydrogen bonding
  • [pi]-[pi] stacking inter­actions

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