Crystal structure and Hirshfeld surface analysis of dimethyl 3,3′-{[(1<i>E</i>,2<i>E</i>)-ethane-1,2-diylidene]bis(azanylylidene)}bis(4-methylbenzoate)
Semanur Yeşilbağ, Emine Berrin Çınar, Necmi Dege, Erbil Ağar, Eiad Saif
Abstract
The title Schiff base compound, C 20 H 20 N 2 O 4 , synthesized by the condensation reaction of methyl 3-amino-4-methylbenzoat and glyoxal in ethanol, crystallizes in the the monoclinic space group P 2 1 / n . The molecule is Z-shaped with the C—N—C—C torsion angle being 47.58 (18)°. In the crystal, pairs of molecules are linked via C—H...N hydrogen bonds, forming centrosymetric dimers with an R 2 2 (8) ring motif; this connectivity leads to the formation of columns running along the a- axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to explore the intermolecular interactions and revealed that the most significant contributions to the crystal packing are from H...H (49.4%), H...O/O...H (19.0%) and H...C/C...H (17.5%) contacts. Energy frameworks were constructed through different intermolecular interaction energies to investigate the stability of the compound. The net interaction energies for the title compound were found to be electrostatic ( E ele = −48.4 kJ mol −1 ), polarization ( E pol = −9.7 kJ mol −1 ), dispersion ( E dis = −186.9 kJ mol −1 ) and repulsion ( E rep = 94.9 kJ mol −1 ) with a total interaction energy, E tot , of −162.4 kJ mol −1 .