Synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations of 2, 2, 2-tribromo-1-(3,5-dibromo-2-hydroxyphenyl)ethanone

Abstract

A novel derivative 2, 2, 2-tribromo-1- (3,5-dibromo-2-hydroxyphenyl) ethanone was synthesis by “3-acetyl-4-hydroxycoumarin” and dibromide. The structural properties of the synthesized compound have been exploited with the aid of single-crystal X-ray crystallographic studies and infrared spectrometry. The compound crystallizes in the monoclinic system with space group P21/c. A comparative study between the novel brominated compound synthesized and the brominated coumarin derivative is presented. The optimized DFT geometries (B3PW91/6–311 G (2df, p)) and the spectral simulations of two derivatives compared agree well with the experimental data. Hirshfeld's analysis revealed the importance of Br ··· Br (40%) and Br ··· H/H ··· Br (19%) of the total surface contacts in the molecular stack. The contacts O···H/H···O have a significant contribution for the brominated coumarin (C2) of 26.1% of SH compared to the brominated cycle (C1) 9.7%.