In this work, a new tridentate ligand, its some novel zinc halide/pseudohalide complexes and their antimicrobial and cytotoxic effects of them are described. Characterization data of these compounds have been achieved via several physical and micro analytical techniques. As typical one, X-ray crystal structure analysis of zinc azide complex was run showing zinc center is penta-coordinated by three nitrogen atoms from Schiff base ligand and two terminal azide nitrogen atoms as a distorted square pyramidal geometry. Hirshfeld surfaces analysis clears the important role of interactions related to azide groups (NH⋯N and CH⋯N hydrogen bonds) in the stabilization of its supramolecular structure. According to data obtained from thermal analysis (TG/DTG/DTA), all complexes are decomposed at four or more thermal stages below 1000 °C. Moreover antimicrobial activities of the compounds were screened against some gram positive and gram negative bacteria. Furthermore anticancer activities of the complexes were studied against MDA-MB468 and k562 as two cancer cell lines. In final, three zinc complexes were also synthesized in nano scale by sonochemical method and one of them was utilized as the precursor for preparation of nanostructure ZnO confirmed by XRD pattern and SEM image.