Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2020-08, Vol.76 (8), p.1195-1200
• Main Authors: Faizi, Md. Serajul Haque, Cinar, Emine Berrin, Aydin, Alev Sema, Agar, Erbil, Dege, Necmi, Mashrai, Ashraf
• Format: Article
• Language: English
• Subjects: 2 aminobenzonitrile; 2-hydroxy-5-methyl-benzaldehyde; crystal structure; schiff base
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989020008907

The title compound, C 15 H 12 N 2 O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca . The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is E , stabilized by a strong intramolecular O—H...N hydrogen bond that forms an S (6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the a axis. C—H...π interactions, 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 interactions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is given.