Synthesis, Crystal Structure and Non-covalent Interactions Analysis of Novel N-substituted Thiosemicarbazone

Abstract

(E)-1-(4-Fluorobenzylidene)-4-(4-ethylphenyl)thiosemicarbazone was synthesized via the reaction of 4-(4-ethylphenyl)thiosemicarbazide and 4-fluorobenzaldehyde. The title compound was characterized by FTIR, ¹H and ¹³C NMR, mass spectrometry and elemental analysis techniques. Structural property of the title compound was displayed by the X-ray single crystal diffraction. The title compound crystallized in triclinic space group $P\overline 1$ with a=0.6494(4) nm, b=0.7971(5) nm, c=1.5492(10) nm, α=83.690(11)°, β=84.185(10)°, γ=84.348(11)°, molecular formula C₁₆H₁₆FN₃S, M _r=301.39, V=0.7868(9) nm³, Z=2, D _c=1.272 g/cm³, F(000)=316, μ=0.213 mm⁻¹, S=1.02, R=0.0513, and ωR[I>2σ(I)]=0.1662. The intermolecular interactions in the crystal structure were explained using the Hirshfeld surface and their associated two-dimensional fingerprint plots. The title compound showed C—H⋯S(1−x, −y, −z) and N—H⋯S(1−x, −y, −z) intermolecular interactions, and formed the supramolecular self-assemblies through $\overline G $ and ${\rm{R}}_2^2(8)$ ring motifs. Shape index and curvedness were performed to further understand some unique weak interactions, for instance, the weak π…π stacking contacts in molecular structure with different characteristic regions. Besides, the reduced density gradient(RDG) function provided a real-space function for discussing non-covalent interactions within molecule, such as hydrogen bonds, weak vdW interactions and attractive or repulsive effects.

Keywords

Novel N-substituted thiosemicarbazone / Non-covalent interaction / Reduced desity gradient(RDG) function / Hirshfeld surface analysis

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