Crystal structure and optical properties of fusedring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl) prop-2-en-1-one

Abstract

The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63(14)° between the anthracene ring system and the benzene ring. In the crystal, molecules are linked into inversion dimers with an R 2 2 (10) graph-set motif via pairs of C - H⋯O hydrogen bonds. The intermolecular interactions were analysed and quantified by Hirshfeld surface analysis. The molecular structure was optimized and a small HOMO-LUMO energy gap of 2.55eV was obtained using the DFT method at the B3LYP/6-311G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52eV obtained from the UV-vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996(16):0.8004(16).