Synthesis, Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy and Energy Framework Studies of Novel Hydrazone Derivative Containing Barbituric Acid Moiety

New hydrazone derivate, (1Z,2E)-2-(2-(1-(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)ethyl)hydrazineylidene)-2-(p-tolyl)acetaldehyde oxime (H₂L) was synthesized by 5-acetyl-1,3-dimethyl-barbituric acid and p-methyl isonitrosophenylhydrazine. Its molecular and crystal structures were determined by single crystal X-ray analysis. It belongs to triclinic system P-1 space group with a = 7.1722 (3) Å, b = 10.5362 (4) Å, c = 11.7675 (5) Å, α = 98.844 (4)°, β = 98.882 (4)°, γ = 104.330 (4)°, Z = 2 and V = 833.95 (6) ų. In the molecular structure, the intramolecular N–H···O and N–H···N hydrogen bonds enclose S(6) ring motifs. In the crystal structure, the intermolecular C–H···O and O–H···O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R₂²(10) and R₄⁴(10) ring motifs, in which they may be effective in stabilization of the structure. The Hirshfeld surface analysis of crystal structure indicates that the most important contributions for crystal packing are from H…H (48.5%), H…O/O…H (23.7%) and H…C/C…H (9.7%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in crystal packing. Computational chemistry indicates that in the crystal, O–H···O and C–H···O hydrogen bond energies are 95.9 and 87.5 kJ mol⁻¹. The evaluation of the electrostatic, dispersion and total energy frameworks indicates that stabilization is dominated via the nearly equal strengths of the electrostatic and dispersion energy contributions.

Graphical Abstract