Crystal structure and Hirshfeld surface analysis of dimethyl 3,3′-{[(1E,2E)-ethane-1,2-diyl­idene]bis(aza­nylyl­idene)}bis­(4-methyl­benzoate)

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 P2(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).