Weak C–H···O and Dipole–Dipole Interactions as Driving Forces in Crystals of Fluorosubstituted Phenylboronic Catechol Esters

Abstract

The analysis of weak interactions in crystals of a series of fluorosubstituted phenylboronic catechol esters (fphb) supported by Hirshfeld surface analysis is presented. The influence of the number and positions of fluorine atoms on the molecular structure is discussed and compared with results of the DFT calculations for isolated molecules. The molecular symmetry breaking caused by the intermolecular interactions was detected. The substantial differentiation of the dipole moments generated by fluorine substitution and its consequence on molecular packing are analyzed. The presence of ortho-fluoro substituents was found to enhance the proton acceptor character of oxygen atoms. Consequently, the C–H···O hydrogen-bonded centrosymmetric dimer is the dominating motif for molecules with small dipole moments. Otherwise, the antiparallel dipole–dipole interactions are responsible for the supramolecular architecture.