Cinar, Emine BerrinFaizi, Md Serajul HaqueYagci, Nermin KahveciDogan, Onur ErmanAydin, Alev SemaAgar, ErbilDege, Necmi2021-01-142021-01-142020Cinar, E. B., Faizi, M. S. H., YAĞCI, N. K., Doğan, O. E., Aydin, A. S., Ağar, E., ... DEGE, N.(2020). Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitrophenyl)imino]methyl}phenol. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS , vol.76, 1551-1561.2056-9890https://doi.org/10.1107/S2056989020011652https://hdl.handle.net/20.500.12587/12560Dege, Necmi/0000-0003-0660-4721; CINAR, Emine Berrin/0000-0001-7617-3459; Mashrai, Ashraf/0000-0002-6317-154X; Faizi, Md. Serajul Haque/0000-0002-4678-9508The title compound, C15H14N2O3, was prepared by condensation of 2-hydroxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenylamine in ethanol. The configuration of the C=N bond is E. An intramolecular O-H center dot center dot center dot 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)degrees]. In the crystal, molecules are linked by C-H center dot center dot center dot O interactions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H center dot center dot center dot H (37.2%), C center dot center dot center dot H (30.7%) and O center dot center dot center dot H (24.9%) interactions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared to the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.eninfo:eu-repo/semantics/openAccesscrystal structure2-hydroxy-5-methyl-benzaldehyde2-methyl-3-nitro-phenylamineSchiff baseArticle761551+10.1107/S20569890200116522-s2.0-8509245305233117562Q3WOS:000577165000003N/A