Crystal Structure, Hirshfeld Surface Analysis and DFT Studies of 4-Methyl

Abstract

The title compound, C15H12F3NO, crystallizes with one molecule in the asymmetric unit. The configuration of the C = N bond is E and there is an intramolecular O-H center dot center dot center dot N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-trifluoromethylphenyl rings is 44.77 (3)degrees. In the crystal, molecules are linked by C-H center dot center dot center dot O interactions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C center dot center dot center dot H/H center dot center dot center dot C (29.2%), H center dot center dot center dot H (28.6%), F center dot center dot center dot H/H center dot center dot center dot F (25.6%), O center dot center dot center dot H/H center dot center dot center dot O (5.7%) and F center dot center dot center dot F (4.6%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.