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

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

doi:10.1107/s2056989020007847

Abstract

In the title compound, C15H15NO, the configuration of the C=N bond of the Schiff base is E, and an intra-molecular O-H⋯N hydrogen bond is observed, forming an intra-molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol-ecules are linked along the b axis by O-H⋯N and C-H⋯O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (56.9%) and H⋯C/C⋯H (31.2%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure, and the HOMO-LUMO energy gap is provided. The crystal studied was refined as an inversion twin.

Highlights

Molecules are linked along the b axis by O—HÁ Á ÁN and C—HÁ Á ÁO hydrogen bonds, forming polymeric chains
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from HÁ Á ÁH (56.9%) and HÁ Á ÁC/CÁ Á ÁH (31.2%) interactions
We report the crystal structure as well as the Hirshfeld surface analysis of the title Schiff base (E)-4-methyl-2-{[(4-methylphenyl)imino]methyl}phenol, (I)

Summary

Chemical context

Azomethines (known as Schiff bases), having imine groups (CH N) and benzyl rings alternately in the main chain and being conjugated, are interesting materials for a wide spectrum of applications, in particular as metal-ion complexing agents and in biological systems (Hokelek et al, 2004; Moroz et al, 2012; Kansız & Dege, 2018). Schiff bases are important in various areas of chemistry and biochemistry because of their biological activity (El-masry et al, 2000) and photochromic properties. They have applications in various fields such as the measurement and control of radiation intensities in imaging systems and optical computers (Elmalı et al, 1999), and electronics, optoelectronics and photonics (Iwan et al, 2007). They are used as anion sensors (Dalapati et al, 2011) and as non-linear optics compounds (Sun et al, 2012).

Structural commentary

DFT calculations

Database survey

Findings

Synthesis and crystallization