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Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-meth­oxy­anilino)methyl­idene]-2-hy­droxy­cyclo­hexa-2,4-dien-1-one

The title compound, C(14)H(12)ClNO(3), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol­ecule is stabilized by a strong intra...

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Detalles Bibliográficos
Autores principales: Demir Kanmazalp, Sibel, Doĝan, Onur Erman, Taşdemir, Volkan, Dege, Necmi, Aĝar, Erbil, Fritsky, Igor O.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6399700/
https://www.ncbi.nlm.nih.gov/pubmed/30867950
http://dx.doi.org/10.1107/S2056989019002123
Descripción
Sumario:The title compound, C(14)H(12)ClNO(3), is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol­ecule is stabilized by a strong intra­molecular N—H⋯O hydrogen bond. In the crystal, pairs of centrosymmetrically related mol­ecules are linked by O—H⋯O hydrogen bonds, forming R (2) (2)(10) rings. Besides this, the mol­ecules form stacks along the [001] direction with C—H⋯π and C—H⋯Cl contacts between the stacks. The inter­molecular inter­actions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H⋯H contacts (30.8%).