Abstract
The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 2-amino-benzo-nitrile, and crystallizes in the ortho-rhom-bic space group Pbca. The phenol ring is inclined to the benzo-nitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intra-molecular O-H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H⋯O and C-H⋯N inter-actions lead to the formation of sheets perpendicular to the a axis. C-H⋯π inter-actions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H⋯H and C⋯H/H⋯C 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 given.
Highlights
We report the synthesis of the title compound 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile (I) from 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, as well as its crystal structure, Hirshfeld surface analysis and density functional theory (DFT) computational calculations
Supramolecular features and Hirshfeld surface analysis The crystal structure of the title compound is consolidated by C—HÁ Á ÁO and C—HÁ Á ÁN interactions, forming corrugated layers perpendicular to the a axis (Fig. 2, Table 1)
The darkest red spots on the Hirshfeld surface indicate contact points with atoms participating in the C—HÁ Á Á interactions involving C11— H11 and the phenyl substituent (Table 1)
Summary
Schiff bases containing the azomethine moiety (–RCH N– R0) are prepared by a condensation reaction between amines and reactive carbonyl compounds, such as aldehydes. Schiff bases are employed as catalyst carriers (Grigoras et al, 2001), thermo-stable materials (Vanco et al, 2004), metal–cation complexing agents and in biological systems (Taggi et al, 2002). Schiff bases are capable of forming stable complexes by coordination to metal ions via their nitrogen donor atoms (Ebrahimipour et al, 2012). They are important for their photochromic properties and have applications in various fields such as the measurement and control of radiation intensities in imaging systems and in optical computers, electronics, optoelectronics and photonics (Iwan et al, 2007). Of À178.75 (13) and the C1—C14—C15—N1 torsion angle [0.31 (3) for X-ray and 0.44 for B3LYP]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
