Crystal structure, Hirshfeld surface analysis and antioxidant capacity of 2,2′-{(1E,1′E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(5-benzyloxy)phenol

Abstract

The whole molecule of the title Schiff base compound, C34H28N2O4, is generated by mirror symmetry, with the mirror bisecting the central benzene ring. It was synthesized via the condensation reaction of 1,2-diaminebenzene with 4-benzyloxy-2-hydroxybenzaldehyde. The molecule is V-shaped and there are two intramolecular O—H...N hydrogen bonds present forming S(6) ring motifs. The configuration about the C=N imine bonds is E. The central benzene ring makes dihedral angles of 41.9 (2) and 43.6 (2)° with the phenol ring and the outer benzyloxy ring, respectively. The latter two rings are inclined to each other by 84.4 (2)°. In the crystal, molecules are linked by C—H...π interactions, forming layers lying parallel to the ab plane. The Hirshfeld surface analysis and the two-dimensional fingerprint plots confirm the predominance of these interactions in the crystal structure. The antioxidant capacity of the compound was determined by the cupric reducing antioxidant capacity (CUPRAC) process.

Keywords

• crystal structure
• Schiff base
• antioxidant capacity
• CUPRAC
• hydrogen bonding
• C—H...π interactions
• Hirshfeld surface analysis