Abstract
The Schiff base compound, C24H24N2O4, was synthesized by the inter-action of 2-hy-droxy-3-meth-oxy benzaldehyde and 1,4-benzene dimethanamine in ethanol, and crystallizes in the monoclinic space group P21/n with Z' = 0.5. The mol-ecule is not planar, the 1,4-di-ethyl-benzene and the phenol rings are twisted with respect to each other, making a dihedral angle of 74.27 (5)°. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules 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 inter-molecular contacts controlling the supra-molecular topology, suggesting the H⋯O (18%) contacts to be the most significant inter-actions, whereas the H⋯H (50.5%) and C⋯H (24.3%) inter-actions are less significant.
Highlights
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 Z0 = 0.5
The molecular structure is stabilized by an O—HÁ Á ÁN hydrogen bond, forming an S(6) ring motif
Of particular interest are the two different tautomeric structures for o-hydroxy Schiff bases, which are expressed as keto-amine and phenol-imine, with intrinsic N—HÁ Á ÁO or O— HÁ Á ÁN hydrogen bonds, (Filarowski et al, 2004)
Summary
Schiff bases are used as pigments and dyes, catalysts, intermediates in organic synthesis, and as polymer stabilizers (Supuran et al, 1996). There is an intramolecular O2—H2Á Á ÁN1 hydrogen bond (Table 1 and Fig. 1); this is a common feature observed in related phenol-imine Schiff bases. It forms an S(6) ring motif and induces the phenol ring and the Schiff base to be nearly coplanar, as indicated by the C6—C8—N1—C9 torsion angle of 178.54 (13). The N1—C8 bond is short at 1.2717 (17) A , strongly indicating a C N double bond, while the long C6—C8 bond [1.451 (2) A ] implies a single bond All of these data support the existence of the phenol–imine tautomer for the title compound in the crystalline state.
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