Abstract A new trifluoromethyl-1,5-benzodiazepine (BDZP) was synthesized from 2-trifluoromethyl chromone and o-phenylendiamine in ethanol. The X-ray crystal structure determination of BDZP shows that the compound exists in the solid as Enol-imine and Keto-enamine tautomeric, with prevalence of the former tautomer. The crystal packing of BDZP is stabilized by C–H⋯F, C–H⋯O, C–H⋯π, π⋯π stacking, lone pair (F) ⋯π and F⋯F interactions. These contacts were evaluated in detail by Hirshfeld surface analysis and DFT calculations. Energy framework calculations afforded to analyze and visualize the topology of the intermolecular interactions responsible for the crystal packing, showing that dispersion interaction prevails over the electrostatic energy in all structural motifs of BDZP.