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Open AccessCommunication

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

1
Department of Chemistry, Universidad del Valle, A.A. 25360, Santiago de Cali, Colombia
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Department of Chemistry, Universidad de los Andes, Bogotá 111711, Colombia
3
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
Molbank 2017, 2017(1), M934; https://doi.org/10.3390/M934
Received: 16 January 2017 / Revised: 8 February 2017 / Accepted: 28 February 2017 / Published: 9 March 2017
(This article belongs to the Section Structure Determination)
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
MDPI and ACS Style

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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