The title Schiff base compound, C20H20N2O4, synthesized by the condensation reaction of methyl 3-amino-4-methylbenzoat and glyoxal in ethanol, crystallizes in the the monoclinic space group P21/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.

The Schiff base compound, C24H24N2O4, was synthesized by the interaction of 2-hydroxy-3-methoxy benzaldehyde and 1,4-benzene dimethanamine in ethanol, and crystallizes in the monoclinic space group P21/n with Z′ = 0.5. The molecule is not planar, the 1,4-diethylbenzene and the phenol rings are twisted with respect to each other, making a dihedral angle of 74.27 (5)°. The molecular structure is stabilized by an O—H...N hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by C—H...O hydrogen bonds, resulting in the formation of sheets parallel to the bc plane. A Hirshfeld surface analysis was undertaken to investigate the various intermolecular contacts controlling the supramolecular topology, suggesting the H...O (18%) contacts to be the most significant interactions, whereas the H...H (50.5%) and C...H (24.3%) interactions are less significant.

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Molecules of the title compound, C16H16N2O2, occupy special positions on the twofold rotation axes. The heterocyclic ring adopts a slightly twisted envelope conformation with one of the two junction carbon atoms as the flap. The mean planes through the two halves of the molecule form a dihedral angle of 72.01 (2)°. In the crystal, molecules are linked by pairs of C—H...O and N—H...C contacts into layers parallel to (100). H...H contacts make the largest contribution to the Hirshfeld surface (58.9%).