Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromo-phen-yl)-3-(3-fluoro-phen-yl)prop-2-en-1-one.

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).

SUBMITTER: Zaini MF 

PROVIDER: S-EPMC6323881 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature