Abstract
The bis-(anil) mol-ecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol-enol form, exhibiting intra-molecular O-H⋯N hydrogen bonds. The two hy-droxy-naphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis-(anil) mol-ecules form an inversion dimer by a pair of weak C-H⋯O inter-actions. The dimers arrange in a one-dimensional column along the b axis via another C-H⋯O inter-action and a π-π stacking inter-action between the hy-droxy-naphthalene ring system with a centroid-centroid distance of 3.6562 (16) Å. The solvent 1,2-di-chloro-benzene mol-ecules are located between the dimers and bind neighbouring columns by weak C-H⋯Cl inter-actions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone de-acetyl-ase SIRT2, histone de-acetyl-ase class III and histone de-acetyl-ase SIRT1 activities, and will act as inhibitor to aspulvinone di-methyl-allyl-transferase, de-hydro-l-gulonate deca-rboxylase and gluta-thione thiol-esterase.
Highlights
The bis(anil) molecule of the title compound, C47H32N2O2ÁC6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—HÁ Á ÁN hydrogen bonds
The dimers arrange in a onedimensional column along the b axis via another C—HÁ Á ÁO interaction and a – stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) A
The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—HÁ Á ÁCl interactions
Summary
Schiff bases formed by the condensation of salicylaldehydes with amines are known as anils They often exhibit potent antibacterial, antiproliferative and antitoxic properties (Williams, 1972). They are an important class of ligands, which are widely used in inorganic and coordination chemistry (Devi et al, 2019). Non-coordinating anils undergo excited-state intramolecular proton transfer (ESIPT), which make them attractive objects for photophysical investigations (Minkin et al, 2011; Cohen & Schmidt, 1962). Their colours and proton-transfer equilibrium is greatly dependent on the substituents in the core (Sliwa et al, 2009, 2010). Symmetry codes: (i) Àx þ 1; Ày þ 2; Àz þ 1; (ii) Àx þ 1; Ày þ 1; Àz þ 1; (iii) Àx þ 2; Ày þ 2; Àz þ 1
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