Synthesis, Crystal structure, Hirshfeld surface analysis and DFT studies of 2-bromo-4,6-bis(dibromoacetyl)resorcinol

Abstract

Abstract The synthesis and crystal structure of 2-bromo-4,6-bis(dibromoacetyl)resorcinol, I, was reported. In the title compound, I, crystalized in the triclinic crystal system with Pī space group. The two carbon and the oxygen atom of the acetyl groups (atoms C7, C8, O3, and C9, C10, O4) are nearly co-planar with the central phenyl ring. Intramolecular O–H···O, C–H···Br, and intermolecular C–H···Br/O interactions, two non-bonded contacts (Br5···Br3 and O4···C8) and π-π stacking interaction are stabilized the crystal packing of the title compound. Intermolecular interactions that exist in the title compound, I, are quantified with the aid of PIXEL and Hirshfeld surface (HS) analysis and the decomposed fingerprint (FP) plots. The FP plot reveals that the Br···Br contacts are comparably higher than the other contacts in the title crystal structure. Furthermore, the theoretical density functional theory (DFT) calculations were performed at the M062X /cc-PVTZ level of theory. The experimental geometry parameters of the title molecule are compared with the geometry of the optimized molecule in the gas phase. The chemical reactivity and charge transfer properties of the title compound were calculated from the HOMO and LUMO energy. In addition, the molecular electrostatic potential map was generated at their crystal structure geometry and quantitatively analyzed.