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

Abstract

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 alpha = 7.1722 (3) angstrom, b= 10.5362 (4) angstrom, c =11.7675 (5) angstrom, alpha = 98.844 (4)degrees, beta = 98.882 (4)degrees, gamma =104.330 (4)degrees, Z=2 and V=833.95 (6) angstrom(3). In the molecular structure, the intramolecular N-H center dot center dot center dot O and N-H center dot center dot center dot N hydrogen bonds enclose S(6) ring motifs. In the crystal structure, the intermolecular C-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds link the molecules into centrosymmetric dimers, enclosing R-2(2)(10) and R-4(4)(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 center dot center dot center dot H (48.5%), H center dot center dot center dot O/center dot center dot center dot center dot H (23.7%) and H center dot center dot center dot C/C center dot center dot center dot 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 center dot center dot center dot O and C-H center dot center dot center dot 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.