Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitro-phen-yl)imino]-meth-yl}phenol.

Alev Sema Aydin,Nermin Kahveci Yagci,Md. Serajul Haque Faizi,Ashraf Mashrai,Necmi Dege,Onur Erman Dogan,Emine Berrin Cinar,Erbil Agar

doi:10.1107/s2056989020011652

Abstract

The title compound, C15H14N2O3, was prepared by condensation of 2-hy-droxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenyl-amine in ethanol. The configuration of the C=N bond is E. An intra-molecular O-H⋯N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C-C-N-C torsion angle of 178.53 (13)°]. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.2%), C⋯H (30.7%) and O⋯H (24.9%) inter-actions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared to the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Highlights

The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from HÁ Á ÁH (37.2%), CÁ Á ÁH (30.7%) and OÁ Á ÁH (24.9%) interactions
We report on the synthesis, crystal structure as well as Hirshfeld surface analysis of the title compound (I)
Supramolecular features In the crystal, molecules are linked by two intermolecular interactions, C14—H14Á Á ÁO2i and C7—H7CÁ Á ÁO1i, resulting in the formation of an infinite chain along the b-axis direction (Fig. 2 and Table 1)

Summary

Chemical context

Over the past 25 years, extensive research has surrounded the synthesis and use of Schiff base compounds in organic and inorganic chemistry, as they have important medicinal and pharmaceutical applications. These compounds show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al, 2001; Singh & Dash, 1988; Karia & Parsania, 1999). Ortho-Hydroxy Schiff base compounds such as the title compound can display two tautomeric forms, the enol–imine (OH) and keto–amine (NH) forms. Two types of intramolecular hydrogen bonds are generally observed in ortho-hydroxy Schiff bases, namely, O—HÁ Á ÁN in enol–imine and N—HÁ Á ÁO in keto–amine tautomers (Tanak et al, 2010). Symmetry code: (i) Àx þ 32; y À 12; z

Structural commentary

Hirshfeld surface analysis and two-dimensional fingerprint plots

DFT calculations

Database survey

Synthesis and crystallization

Findings

Refinement