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3-Acetyl-4-hydroxyquinolin-2(1H)-one: resonance-assisted $O-H...O$ hydrogen bonding

Sarveswari, S and Raja, TK and Vijayaraghavan, R and Narasimhamurthy, T and Rathore, RS (2007) 3-Acetyl-4-hydroxyquinolin-2(1H)-one: resonance-assisted $O-H...O$ hydrogen bonding. In: Acta Crystallographica Section E Structure Reports Online, E63 . o4600-o4600.

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Abstract

The molecule of the title compound, $C_{11}H_9NO_3$, a pharmacologically important quinoline derivative, adopts an overall planar shape. The structure is stabilized by an intramolecular $O—H...O=C$ hydrogen bond, forming an S(6) hydrogenbonded ring pattern. The $O—H...O=C$ interaction results in delocalization of the electron density within the dihydropyridine ring, as observed for resonance-assisted hydrogen bonds, leading to lengthening of the carbonyl O=C and pyridyl C=C bonds, and shortening of the C—OH bond in this hydrogen-bonded S(6) ring structure. The cooperative intermolecular $N—H...O$ hydrogen bonds cluster molecules into closed dimers, characterized by an $R^2_2(8)$ ring pattern. Aromatic–aromatic stacking interactions are also observed in the packing, with an interplanar distance of 3.352 \AA and a slippage of 1.855 \AA.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to International Union of Crystallography.
Keywords: single-crystal;X-ray
Department/Centre: Division of Chemical Sciences > Materials Research Centre
Date Deposited: 04 Jun 2008
Last Modified: 19 Sep 2010 04:45
URI: http://eprints.iisc.ernet.in/id/eprint/14180

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