By the proper choice of the substituents on the aldehyde and amine groups, the nature of the Schiff base formed (fully condensed or half condensed) can be tuned by the templating effect of the metal ion. The condensation of 5-chlorosalicylaldehyde with ethylene diamine in the presence of Co(II) or Cu(II) cations and azido anions has afforded two new half condensed Schiff base metal complexes [CuL(µ1,1-N3)]2 (1) and [CoL2]N3·H2O (2), where L = (E)-2-((2-aminoethyl)methyl)-4-chlorophenol, that were structurally characterized by X-ray analysis, IR and UV spectra. Complex 1 is an asymmetric µ-1,1 azide bridged dimer displaying weak antiferromagnetic interactions (J = −2.93 ± 0.03 cm−1), in agreement with the axial-equatorial N3-linkage between the two copper centers. Complex 2 is a monomer of a low spin Co(III) ion.