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Crystal structure and Hirshfeld surface analysis of dimethyl 3,3'-{[(1E,2E)-ethane-1,2-diyl-idene]bis(aza-nylyl-idene)}bis-(4-methyl-benzoate).


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.

SUBMITTER: Yesilbag S 

PROVIDER: S-EPMC8983970 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of dimethyl 3,3'-{[(1<i>E</i>,2<i>E</i>)-ethane-1,2-diyl-idene]bis(aza-nylyl-idene)}bis-(4-methyl-benzoate).

Yeşilbağ Semanur S   Çınar Emine Berrin EB   Dege Necmi N   Ağar Erbil E   Saif Eiad E  

Acta crystallographica. Section E, Crystallographic communications 20220301 Pt 4


The title Schiff base compound, C<sub>20</sub>H<sub>20</sub>N<sub>2</sub>O<sub>4</sub>, synthesized by the condensation reaction of methyl 3-amino-4-methyl-benzoat and glyoxal in ethanol, crystallizes in the the monoclinic space group <i>P</i>2<sub>1</sub>/<i>n</i>. 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 <i>via</i> C-H⋯N hydrogen bonds, forming centrosymetric dimers with an <i>R</i> <sub>2</sub> <sup>2</sup>(8) r  ...[more]

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