Crystal structure, Hirshfeld surface, DFT and molecular docking studies of 2-{4-[(E)-(4-acetylphenyl)diazenyl]phenyl}-1-(5-bromothiophen-2-yl)ethanone; a compound with bromine...oxygen-type contacts

Abstract

The title compound, C19H13BrN2O3S, a non-liquid crystal molecule, crystallizes in the orthorhombic system, space group Pna21. The torsion angles associated with ester and azo groups are −177.0 (4)°, -anti-periplanar, and 179.0 (4)°, +anti-periplanar, respectively. The packing is consolidated by a weak C—Br...O=C contact, forming infinite chains running along the [001] direction. A Hirshfeld surface analysis revealed that the major contributions to the crystal surface are from H...H, C...H/H...C, O...H/H...O, Br...H/H...Br and S...H/H...S interactions. The computed three-dimensional energy interactions using the basis set B3LYP\631-G(d,p) show that Edis (217.6 kJ mol−1) is the major component in the structure. The DFT calculations performed at the B3LYP/6–311+ G(d,p) level indicate that the energy gap between HOMO and LUMO is 3.6725 (2) eV. The molecular electrostatic potential (MEP) map generated supports the existence of the Br...O type contact, formed between the electrophilic site of the bromine atom and the nucleophilic site of the ketonic oxygen atom. The molecular docking between the ligand and the Mycobacterium Tuberculosis (PDB ID:1HZP) receptor shows a good binding affinity value of −8.5 kcal mol−1.

Keywords

• crystal structure
• azobenzene
• molecular docking
• c—br...o=c contact
• dft and hirshfeld surface