Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one

Abstract

The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds, forming rings with R12 (6), R22 (10) and R22 (14) graph-set motifs. The dimers are further connected by C-H⋯O interactions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H⋯H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6-311 G++(d,p) basis set reveal that the HOMO-LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the molecular electrostatic potential (MEP).