Crystal structure, Hirshfeld surface, DFT and mol-ecular docking studies of 2-{4-[(E)-(4-acetylphen-yl)diazen-yl]phen-yl}-1-(5-bromo-thio-phen-2-yl)ethanone; a compound with bromine⋯oxygen-type contacts.

The title compound, C(19)H(13)BrN(2)O(3)S, a non-liquid crystal mol-ecule, crystallizes in the ortho-rhom-bic system, space group Pna2(1). 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 inter-actions. The computed three-dimensional energy inter-actions using the basis set B3LYP\631-G(d,p) show that E(dis) (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 mol-ecular 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 mol-ecular docking between the ligand and the Mycobacterium Tuberculosis (PDB ID:1HZP) receptor shows a good binding affinity value of -8.5 kcal mol(-1).