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 crystal structure of the title non-liquid crystal compound is consolidated by C—Br⋯O=C type contacts running continuously along the [001] direction.

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 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 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.