Amel Djedouani1,2, Barkahem Anak3,2, Salima Tabti4, Franck Cleymand5, Michel François5, Solenne Fleutot5. 1. Laboratoire de Physicochimie Analytique et Cristallochimie de Matériaux Organométalliques et Biomoléculaires, Université de Constantine 1, 25000 Constantine, Algeria. 2. Ecole Normale Supérieure de Constantine Assia Djebbar, Ville Universitaire Ali Mendjeli, Constantine 25000, Algeria. 3. Laboratoire de Chimie des Matériaux, Université de Constantine 1, 25000 Constantine, Algeria. 4. Université Bachire El Ibrahimi de Bordj Bou Arraridj, Algeria. 5. Institut Jean Lamour UMR 7198, Parc de Saurupt, CS 14234 F 54042 Nancy, France.
Abstract
The title Schiff base compound, C16H17NO4, crystallizes as a zwitterion, with the phenolic H atom having been transferred to the imino group. The resulting iminium and hy-droxy groups are linked by an intra-molecular N-H⋯O hydrogen bond, enclosing an S(6) ring motif. The conformation about the C=N bond is E and the dihedral angle between the benzene and pyran rings is 70.49 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. There are also C-H⋯π inter-actions and offset π-π inter-actions, involving the pyran rings [inter-centroid distance = 3.4156 (8) Å], which consolidate the three-dimensional structure. Quantum chemical calculations of the mol-ecule are in good agreement with the solid state keto-amine (NH) form of the title compound.
The title Schiff base compound, n class="Chemical">C16H17NO4, crystallizes as a zwitterion, with the phenolic H atom having been transferred to the imino group. The resulting iminium and hy-droxy groups are linked by an intra-molecular N-H⋯O hydrogen bond, enclosing an S(6) ring motif. The conformation about the C=N bond is E and the dihedral angle between the benzene and pyran rings is 70.49 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional supra-molecular structure. There are also C-H⋯π inter-actions and offset π-π inter-actions, involving the pyran rings [inter-centroid distance = 3.4156 (8) Å], which consolidate the three-dimensional structure. Quantum chemical calculations of the mol-ecule are in good agreement with the solid state keto-amine (NH) form of the title compound.
Authors: Imane Faraj; Ali Oubella; Karim Chkirate; Khalil Al Mamari; Tuncer Hökelek; Joel T Mague; Lhoussaine El Ghayati; Nada Kheira Sebbar; El Mokhtar Essassi Journal: Acta Crystallogr E Crystallogr Commun Date: 2022-07-29