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Molbank 2017, 2017(1), M934;

(5-Chloroquinolin-8-yl)-2-fluorobenzoate. The Halogen Bond as a Structure Director

Department of Chemistry, Universidad del Valle, A.A. 25360, Santiago de Cali, Colombia
Department of Chemistry, Universidad de los Andes, Bogotá 111711, Colombia
Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Apartado 678, Bucaramanga, Colombia
Author to whom correspondence should be addressed.
Academic Editor: René T. Boeré
Received: 16 January 2017 / Revised: 8 February 2017 / Accepted: 28 February 2017 / Published: 9 March 2017
(This article belongs to the Section Structure Determination)
Full-Text   |   PDF [1930 KB, uploaded 9 March 2017]


Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and its supramolecular characteristics were analyzed. Thus, the central ester fragment C8/O1/C10(O2)/C11 is almost planar with a root mean square (r.m.s.) deviation of 0.0612 Å and it makes dihedral angles of 76.35(6)° and 12.89(11)°, with quinoline and phenyl rings respectively. The structure shows C–H...X (X = halogen) non-classical hydrogen bonds. It also has a halogen…halogen distance less than the sum of the van der Waals radii (3.2171(15) Å). As a result of interactions with halogen atoms, chains of centrosymmetric dimer that form edge-fused R22(18) rings run parallel to the plane (100). View Full-Text
Keywords: 8-hydroxyquinoline; antitumor agents; single-crystal X-ray diffraction; supramolecular chemistry 8-hydroxyquinoline; antitumor agents; single-crystal X-ray diffraction; supramolecular chemistry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Moreno-Fuquen, R.; Castillo, J.C.; Abonía, R.; Portilla, J.; Henao, J.A. (5-Chloroquinolin-8-yl)-2-fluorobenzoate. The Halogen Bond as a Structure Director. Molbank 2017, 2017, M934.

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