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

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 divers...

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Bibliographic Details
Published in:MolBank 2017-03, Vol.2017 (1), p.M934
Main Authors: Moreno-Fuquen, Rodolfo, Castillo, Juan, Abonía, Rodrigo, Portilla, Jaime, Henao, José
Format: Article
Language:English
Subjects:
8-hydroxyquinoline
antitumor agents
Chlorine
Crystal structure
Crystallography
Dimers
Hydrogen bonds
Hydroxyquinoline
Quinoline
single-crystal X-ray diffraction
supramolecular chemistry
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Summary: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).
ISSN:1422-8599
1422-8599
DOI:10.3390/M934