Abstract

The title Schiff base compound, C20H20N2O4, synthesized by the condensation reaction of methyl 3-amino-4-methyl-benzoat and glyoxal in ethanol, crystallizes in the the monoclinic space group P21/n. The mol-ecule is Z-shaped with the C-N-C-C torsion angle being 47.58 (18)°. In the crystal, pairs of mol-ecules 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 inter-molecular inter-actions 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 inter-molecular inter-action energies to investigate the stability of the compound. The net inter-action 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 inter-action energy, E tot, of -162.4 kJ mol-1.

Highlights

  • The title Schiff base compound was synthesized by the condensation reaction of methyl 3-amino-4-methylbenzoat and glyoxal in ethanol

  • We report XRD data and Hirshfeld surface analysis of a new Schiff base compound, dimethyl 3,30-{[(1E,2E)-ethane-1,2diylidene]bis(azanylylidene)}bis(4-methylbenzoate), for which energy frameworks of the crystal packing were calculated

  • The molecule is Z-shaped with the C10—N1—C7—C8 torsion angle being 47.58 (18)

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Summary

Chemical context

The title Schiff base compound was synthesized by the condensation reaction of methyl 3-amino-4-methylbenzoat and glyoxal in ethanol. Schiff bases having chelation with oxygen and nitrogen donors and their complexes have been used as drugs and are reported to possess a wide variety of biological activities against bacteria, fungi and certain types of tumors; in addition, they have many biochemical, clinical and pharmacological properties (Przybylski et al, 2009; Barbosa et al, 2020). In recent years, these molecules, which belong to a large family of click reactions, have attracted a lot of interest for their role in the development of self-healing hydrogels (Xu et al, 2019). The azomethine C N bond length is 1.2713 (17) A , which is quite close to the corresponding values reported by Gumus et al (2021) and Kansiz et al (2021) [1.276 (6) and 1.287 (6) Aand 1.287 (5) A , respectively]

Supramolecular features
Findings
Synthesis and crystallization
Full Text
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