Role of fluorine-fluorine and weak intermolecular interactions in the supramolecular network of a new trifluoromethyl-1,5-benzodiazepine: Crystal structure, Hirshfeld surface analysis and theoretical study

ROCHA, MARIANA; ECHEVERRÍA, GUSTAVO A.; PIRO, OSCAR E.; JIOS, JORGE L.; ULIC, SONIA E.; GIL, DIEGO M.

JOURNAL OF FLUORINE CHEMISTRY

ELSEVIER SCIENCE SA

Año: 2021 vol. 242

0022-1139

A new trifluoromethyl-1,5-benzodiazepine (BDZP) was synthesized from 2-trifluoromethyl chromone and ophenylendiamine 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.