info:eu-repo/semantics/article
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
Fecha
2021-02Registro en:
Rocha, Mariana; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Ulic, Sonia Elizabeth; et al.; 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; Elsevier Science SA; Journal of Fluorine Chemistry; 242; 109697; 2-2021; 1-11
0022-1139
CONICET Digital
CONICET
Autor
Rocha, Mariana
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Gil, Diego Mauricio
Resumen
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.