The new diamine 2,2'-(1,4-diazepane-1,4-diyl)dianiline (A1) was synthesized by reaction of 1-Fluoro-2-nitrobenzene and homopiperazine. Two new Schiff base ligands, H2L1 and H2L2 were synthesized from the condensation of 2-hydroxybenzaldehyde (H2L1) and 2-hydroxy-3-methoxybenzaldehyde (H2L2) with A1. In the presence of appropriate metal ions, Co(III) and Cu(II) macroacyclic Schiff-base complexes were obtained. All resultant products were characterized by elemental analysis, mass spectrometry and spectroscopic methods such as: FT-IR, 1H and 13C NMR. In addition the molar conductivity (ɅM) data was measured at 25 °C using 10-3 M solutions of the complexes in CH3CN solvent. The antibacterial activity of free amine and complexes has been studied against some Gram-positive and Gram-negative bacteria