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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.

Sowmya HB, Suresha Kumara TH, Gopalpur N, Jasinski JP, Millikan SP, Yathirajan HS, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: In (III), three of the four independent mol-ecules are linked by π-π stacking inter-actions but the other mol-ecule does not participate in such inter-actions.The mol-ecules of (IV) are linked into chains by a C-H⋯π(arene) hydrogen bond, but π-π stacking inter-actions are absent.In (V), there is an intra-molecular O-H⋯O hydrogen bond, and mol-ecules are linked into sheets by a combination of O-H⋯N hydrogen bonds and π-π stacking inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: PG Department of Chemistry, Jain University, 52 Bellary Road, Hebbal, Bangalore 560 024, India.

ABSTRACT
In the mol-ecules of the title compounds, methyl 5-bromo-2-[(2-chloro-quinolin-3-yl)meth-oxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methyl-quinolin-3-yl)meth-oxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methyl-quinolin-3-yl)meth-oxy]benzoate, C19H16ClNO3, (III), which crystallizes with Z' = 4 in space group P212121, and 2-chloro-3-[(naphthalen-1-yl-oxy)meth-yl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloro-quinolin-3-yl)meth-oxy]-4-(hy-droxy-meth-yl)-6-methyl-pyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The mol-ecules of (I) are linked by two independent π-π stacking inter-actions to form chains, but there are no hydrogen bonds present in the structure. In (II), the mol-ecules are weakly linked into chains by a single type of π-π stacking inter-action. In (III), three of the four independent mol-ecules are linked by π-π stacking inter-actions but the other mol-ecule does not participate in such inter-actions. Weak C-H⋯O hydrogen bonds link the mol-ecules into three types of chains, two of which contain just one type of independent mol-ecule while the third type of chain contains two types of mol-ecule. The mol-ecules of (IV) are linked into chains by a C-H⋯π(arene) hydrogen bond, but π-π stacking inter-actions are absent. In (V), there is an intra-molecular O-H⋯O hydrogen bond, and mol-ecules are linked into sheets by a combination of O-H⋯N hydrogen bonds and π-π stacking inter-actions.

No MeSH data available.


The mol­ecular structure of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
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fig1: The mol­ecular structure of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Mentions: The quinoline nucleus occurs in a number of natural compounds, such as the Cinchona alkaloids, and many of these are pharmacologically active substances displaying a broad range of biological activity. Quinoline itself has been found to possess anti­malarial, anti-bacterial, anti­fungal, anthelminthic, cardiotonic, anti­convulsant, anti-inflammatory and analgesic activity (Marella et al., 2013 ▶). The synthesis, reactions and biological applications of 2-chloro­quinoline-3-carbaldehydes have been reviewed (Abdel-Wahab et al., 2012 ▶), and the structure of a simple reduction product (2-chloro­quinolin-3-yl)methanol, derived from the parent 2-chloro­quinoline-3-carbaldehyde, has been reported (Hathwar et al., 2010 ▶). The structures of two related esters, [(2-chloro­quinolin-3-yl)methyl acetate and (2-chloro-6-methyl­quinolin-3-yl)methyl acetate], have also been reported recently along with a study of their radical-scavenging and anti­microbial activities (Tabassum et al., 2014 ▶). Here we report the structures of five related ethers, namely methyl 5-bromo-2-[(2-chloro­quinolin-3-yl)meth­oxy]benzoate, (I) (Fig. 1 ▶), methyl 5-bromo-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, (II) (Fig. 2 ▶), methyl 2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, (III) (Figs. 3 ▶–6 ▶ ▶ ▶), 2-chloro-3-[(naphthalen-1-yl­oxy)meth­yl]quinoline (IV) (Fig. 7 ▶) and {5-[(2-chloro­quinolin-3-yl)methoxy]-4-(hy­droxy­meth­yl)-6-methylpyridin-3-yl}methanol, (V) (Fig. 8 ▶). Compounds (I)–(V) are all of general type QCH2OR, where Q represents a 2-chloro­quinolin-3-yl unit, which carries a 6-methyl substituent in compounds (II) and (III), although not in compounds (I), (IV) and (V), and where R represents a meth­oxy­carbonyl­phenyl unit in compounds (I)–(III), a 1-naphthyl unit in compound (IV), and a multiply-substituted pyridyl unit in compound (V). Compound (I)–(V) were all prepared by reaction of the corresponding chloro­methyl compounds QCH2Cl with the appropriate hy­droxy compound ROH under basic conditions, with yields ranging from 86 to 97%.


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.

Sowmya HB, Suresha Kumara TH, Gopalpur N, Jasinski JP, Millikan SP, Yathirajan HS, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4459322&req=5

fig1: The mol­ecular structure of compound (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Mentions: The quinoline nucleus occurs in a number of natural compounds, such as the Cinchona alkaloids, and many of these are pharmacologically active substances displaying a broad range of biological activity. Quinoline itself has been found to possess anti­malarial, anti-bacterial, anti­fungal, anthelminthic, cardiotonic, anti­convulsant, anti-inflammatory and analgesic activity (Marella et al., 2013 ▶). The synthesis, reactions and biological applications of 2-chloro­quinoline-3-carbaldehydes have been reviewed (Abdel-Wahab et al., 2012 ▶), and the structure of a simple reduction product (2-chloro­quinolin-3-yl)methanol, derived from the parent 2-chloro­quinoline-3-carbaldehyde, has been reported (Hathwar et al., 2010 ▶). The structures of two related esters, [(2-chloro­quinolin-3-yl)methyl acetate and (2-chloro-6-methyl­quinolin-3-yl)methyl acetate], have also been reported recently along with a study of their radical-scavenging and anti­microbial activities (Tabassum et al., 2014 ▶). Here we report the structures of five related ethers, namely methyl 5-bromo-2-[(2-chloro­quinolin-3-yl)meth­oxy]benzoate, (I) (Fig. 1 ▶), methyl 5-bromo-2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, (II) (Fig. 2 ▶), methyl 2-[(2-chloro-6-methyl­quinolin-3-yl)meth­oxy]benzoate, (III) (Figs. 3 ▶–6 ▶ ▶ ▶), 2-chloro-3-[(naphthalen-1-yl­oxy)meth­yl]quinoline (IV) (Fig. 7 ▶) and {5-[(2-chloro­quinolin-3-yl)methoxy]-4-(hy­droxy­meth­yl)-6-methylpyridin-3-yl}methanol, (V) (Fig. 8 ▶). Compounds (I)–(V) are all of general type QCH2OR, where Q represents a 2-chloro­quinolin-3-yl unit, which carries a 6-methyl substituent in compounds (II) and (III), although not in compounds (I), (IV) and (V), and where R represents a meth­oxy­carbonyl­phenyl unit in compounds (I)–(III), a 1-naphthyl unit in compound (IV), and a multiply-substituted pyridyl unit in compound (V). Compound (I)–(V) were all prepared by reaction of the corresponding chloro­methyl compounds QCH2Cl with the appropriate hy­droxy compound ROH under basic conditions, with yields ranging from 86 to 97%.

Bottom Line: In (III), three of the four independent mol-ecules are linked by π-π stacking inter-actions but the other mol-ecule does not participate in such inter-actions.The mol-ecules of (IV) are linked into chains by a C-H⋯π(arene) hydrogen bond, but π-π stacking inter-actions are absent.In (V), there is an intra-molecular O-H⋯O hydrogen bond, and mol-ecules are linked into sheets by a combination of O-H⋯N hydrogen bonds and π-π stacking inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: PG Department of Chemistry, Jain University, 52 Bellary Road, Hebbal, Bangalore 560 024, India.

ABSTRACT
In the mol-ecules of the title compounds, methyl 5-bromo-2-[(2-chloro-quinolin-3-yl)meth-oxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methyl-quinolin-3-yl)meth-oxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methyl-quinolin-3-yl)meth-oxy]benzoate, C19H16ClNO3, (III), which crystallizes with Z' = 4 in space group P212121, and 2-chloro-3-[(naphthalen-1-yl-oxy)meth-yl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloro-quinolin-3-yl)meth-oxy]-4-(hy-droxy-meth-yl)-6-methyl-pyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The mol-ecules of (I) are linked by two independent π-π stacking inter-actions to form chains, but there are no hydrogen bonds present in the structure. In (II), the mol-ecules are weakly linked into chains by a single type of π-π stacking inter-action. In (III), three of the four independent mol-ecules are linked by π-π stacking inter-actions but the other mol-ecule does not participate in such inter-actions. Weak C-H⋯O hydrogen bonds link the mol-ecules into three types of chains, two of which contain just one type of independent mol-ecule while the third type of chain contains two types of mol-ecule. The mol-ecules of (IV) are linked into chains by a C-H⋯π(arene) hydrogen bond, but π-π stacking inter-actions are absent. In (V), there is an intra-molecular O-H⋯O hydrogen bond, and mol-ecules are linked into sheets by a combination of O-H⋯N hydrogen bonds and π-π stacking inter-actions.

No MeSH data available.