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

In the title compound, C(15)H(15)NO, the configuration of the C=N bond of the Schiff base is E, and an intra­molecular O—H⋯N hydrogen bond is observed, forming an intra­molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol­ecules...

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Detalles Bibliográficos
Autores principales: Yagci, Nermin Kahveci, Faizi, Md. Serajul Haque, Aydin, Alev Sema, Dege, Necmi, Dogan, Onur Erman, Agar, Erbil, Mashrai, Ashraf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336782/
https://www.ncbi.nlm.nih.gov/pubmed/32695455
http://dx.doi.org/10.1107/S2056989020007847
Descripción
Sumario:In the title compound, C(15)H(15)NO, the configuration of the C=N bond of the Schiff base is E, and an intra­molecular O—H⋯N hydrogen bond is observed, forming an intra­molecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, mol­ecules 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%) 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 provided. The crystal studied was refined as an inversion twin.