© 2021, Pleiades Publishing, Ltd.Abstract: In the present study, a Schiff base (E)-2-[(3,5-bis(trifluoromethyl)phenylimino)methyl]-4,6-dichlorophenolhas been synthesized. Its spectroscopic and X-ray single-crystal data have beencompared with the results of theoretical calculations based on the DFT method,as well as molecular electrostatic potential (MEP), HOMO and LUMO, and nonlinearoptical (NLO) effects. Antimicrobial activity of the compound has been testedagainst some bacteria and fungi. According to UV-Vis and agarose gelelectrophoresis methods, the compound interacts with DNA electrostatically andbreaks it oxidatively. Antioxidant activity of the compound measured by the DPPHmethod, is lower than that of BHT.