Crystal Structure, Hirshfeld Surface Analysis And Dft Study Of (2Z)-2-(4-FluoroBenzylIdene)-4-(Prop-2-Yn-1-Yl)-3,4-DiHydro-2H-1,4-BenzoThiaZin-3-One
Sebbar, Nada Kheira
Mague, Joel T.
Essassi, El Mokhtar
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In the title compound, the heterocyclic portion of the dihydrobenzothiazine unit adopts a shallow boat conformation. The propynyl substituent is nearly perpendicular to the plane formed by the rails of the boat. In the crystal, inversion dimers are formed by weak C—H⋯F hydrogen bonds with the dimers forming oblique stacks along the a-axis direction., The title compound, C18H12FNOS, is built up from a 4-fluorobenzylidene moiety and a dihydrobenzothiazine unit with a propynyl substituent, with the heterocyclic portion of the dihydrobenzothiazine unit adopting a shallow boat conformation with the propynyl substituent nearly perpendicular to it. The two benzene rings are oriented at a dihedral angle of 43.02 (6)°. In the crystal, C—HFlurphen⋯FFlurphen (Flurphen = fluorophenyl) hydrogen bonds link the molecules into inversion dimers, enclosing R 2 2(8) ring motifs, with the dimers forming oblique stacks along the a-axis direction. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (33.9%), H⋯C/C⋯H (26.7%), H⋯F/F⋯H (10.9%) and C⋯C (10.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.