In the present article macrocyclic ligand of type (C22H14N4O2) and its transition metal complexes of type[M(C22 H14N4O2)X2]X, where M=Cr(III), and Fe(III), X = Cl-, NO3 - and CH3COO- have been synthesized by template condensation of 1,3-dicarbonyl-phenyl-dihydrazide and 9,10-phenanthrenequinone(PhQ) in methanolic medium in 1:1:1 molar ratio. The structure and geometry of synthesized complexes and ligand is proposed on the basis of various modern physicochemical characterization techniques (spectral, thermal) and found to be six coordinated octahedral geometry of all the synthesized species. Ligand is coordinated to metal in a tetradentate manner in all complexes. Molar conductance measurements showed that reported macrocyclic complexes are weakly electrolytic in nature. All the synthesized compounds have been tested for their in vitro antibacterial activity against two gram +ve and two gram -ve pathogenic bacterial strains viz. Staphylococcus aureus, Bacillus cereus (gram +ve) and Salmonella typhi, E.Coli(gram -ve) to access their inhibiting potential. The results obtained were compared with the standard antibacterial drug Ciprofloxacin. The antiradical activity of some newly synthesized complexes has also been evaluated by using DPPH radical scavenging method and compared with standard antioxidant Ascorbic acid.