A new Schiff base ligand named as 2,2'-((1E,1'E)-((4,5-dichloro-1,2-phenylene)bis(azanylylidene))bis(methanylylidene))bis(4-bromophenol) was prepared via condensation reaction between 4,5-dichloro-o-phenylenediamine and 5-bromosalicylaldehyde in 1:2 molar ratio. Various analytical and spectroscopical methods were employed in characterizing the ligand. The coordination behavior and nature of bonding of various metals like Ni(II), Cu(II), and Zn(II) were deduced using ¹H-NMR, FT-IR, UV-Visible, EI-MS, and magnetic moment analysis. Job's method was also used to deduce the stoichiometry between ligand and metal ions. Further, the optimization of the structure of compounds was performed computationally, along with their quantum chemical calculations. The Ni(II) and Cu(II) complexes were found to exhibit square planar geometry whereas Zn(II) complex formed distorted planar four coordinated geometry. The synthesized compounds were screened for antibacterial activity against bacteria (two Gram-positive and two Gram-negative). Other bioactivities like DNA binding, antioxidant, and anti-inflammatory activity were also performed. Furthermore, molecular docking analysis to correlate data with experimental data was computed using B-DNA and 6COX enzyme protein receptors.