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dc.contributor.authorSowmya, Haliwana B V
dc.contributor.authorSuresha Kumara, Tholappanavara H
dc.contributor.authorGopalpur, Nagendrappa
dc.contributor.authorJasinski, Jerry P
dc.contributor.authorMillikan, Sean P
dc.contributor.authorYathirajan, Hemmige S
dc.contributor.authorGlidewell, Christopher
dc.identifier.citationSowmya , 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 .
dc.identifier.otherPURE: 202736755
dc.identifier.otherPURE UUID: 6446a022-c0f7-488c-8033-20f69544f224
dc.identifier.otherPubMed: 26090133
dc.identifier.otherScopus: 84983150613
dc.identifier.otherWOS: 000369979300061
dc.description.abstractIn 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.
dc.relation.ispartofActa Crystallographica Section E: Crystallographic Communicationsen
dc.rightsCopyright 2015 the Authors. Published under the terms of the Creative Commons Attribution License (, which permits unrestricted use, provided the original author and source are credited.en
dc.subjectCrystal structureen
dc.subjectMol­ecular conformationen
dc.subjectHydrogen bondingen
dc.subject[pi]-[pi] stacking inter­actionsen
dc.subjectQD Chemistryen
dc.titleCrystal 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 stackingen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.description.statusPeer revieweden

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