Abstract
The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent mol-ecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related mol-ecules are linked into dimers via inter-molecular hydrogen bonds, forming rings with R 1 2(6), R 2 2(10) and R 2 2(14) graph-set motifs. The dimers are further connected by C-H⋯O inter-actions 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 mol-ecular electrostatic potential (MEP).
Highlights
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
A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by HÁ Á ÁH 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 highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications
Summary
Chalcones are natural or synthetic compounds belonging to the flavonoid family (Di Carlo et al, 1999), consisting of openchain flavonoids in which the aromatic rings are linked by a three-carbon , -unsaturated carbonyl system (Thanigaimani et al, 2015). The presence of halogen substitutions results in alterations of the physicochemical properties and biological activities of organic compounds, without introducing much major steric change. As a result of this, many researchers have worked intensively on fluorine substitution to develop a wide range of biologically active materials (O’Hagan et al, 2008). As part of our studies in this area, fluoro and bromo substituents were introduced in the title compound and the resulting organic molecular crystal is reported in term of its structural stability, the percentage contributions of the various interactions to the crystal packing, and electronic charge transfer within the molecule
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