Crystal structure, Hirshfeld surface analysis and anti-oxidant capacity of 2,2'-{(1 E,1' E)-[1,2-phenyl-enebis(aza-nylyl-idene)]bis-(methanylyl-idene)}bis-(5-benz-yloxy)phenol

Acta Crystallogr E Crystallogr Commun. 2018 Apr 19;74(Pt 5):682-686. doi: 10.1107/S2056989018005832. eCollection 2018 May 1.

Abstract

The whole mol-ecule of the title Schiff base compound, C34H28N2O4, is generated by mirror symmetry, with the mirror bis-ecting the central benzene ring. It was synthesized via the condensation reaction of 1,2-di-amine-benzene with 4-benz-yloxy-2-hy-droxy-benzaldehyde. The mol-ecule is V-shaped and there are two intra-molecular 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 benz-yloxy ring, respectively. The latter two rings are inclined to each other by 84.4 (2)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming layers lying parallel to the ab plane. The Hirshfeld surface analysis and the two-dimensional fingerprint plots confirm the predominance of these inter-actions in the crystal structure. The anti-oxidant capacity of the compound was determined by the cupric reducing anti-oxidant capacity (CUPRAC) process.

Keywords: CUPRAC; C—H⋯π inter­actions; Hirshfeld surface analysis; Schiff base; anti­oxidant capacity; crystal structure; hydrogen bonding.

Grants and funding

This work was funded by Ministère de l’Enseignement Supérieur et de la Recherche Scientifique grant . University of Constantine1, Algeria grant .