Crystal structure and Hirshfeld surface analysis of 3,4-di-hydro-2 H-anthra[1,2- b][1,4]dioxepine-8,13-dione

Sofia Zazouli; Mohammed Chigr; Ahmed Jouaiti; Nathalie Kyritsakas; El Mostafa Ketatni

doi:10.1107/S2056989020003965

Crystal structure and Hirshfeld surface analysis of 3,4-di-hydro-2 H-anthra[1,2- b][1,4]dioxepine-8,13-dione

Acta Crystallogr E Crystallogr Commun. 2020 Mar 27;76(Pt 4):576-580. doi: 10.1107/S2056989020003965. eCollection 2020 Apr 1.

Authors

Sofia Zazouli¹, Mohammed Chigr², Ahmed Jouaiti¹, Nathalie Kyritsakas³, El Mostafa Ketatni²

Affiliations

¹ Laboratory of Sustainable Development, Sultan Moulay Slimane University, Faculty of Sciences and Technologies, BP 523, 23000 Beni-Mellal, Morocco.
² Laboratory of Organic and Analytical Chemistry, University Sultan Moulay Slimane, Faculty of Science and Technology, PO Box 523, Beni-Mellal, Morocco.
³ Molecular Tectonics Laboratory, Université de Strasbourg, CNRS, CMC UMR 7140, F-67000 Strasbourg, France.

Abstract

The title compound, C₁₇H₁₂O₄, was synthesized from the dye alizarin. The dihedral angle between the mean plane of the anthra-quinone ring system (r.m.s. deviation = 0.039 Å) and the dioxepine ring is 16.29 (8)°. In the crystal, the mol-ecules are linked by C-H⋯O hydrogen bonds, forming sheets lying parallel to the ab plane. The sheets are connected through π-π and C=O⋯π inter-actions to generate a three-dimensional supra-molecular network. Hirshfeld surface analysis was used to investigate inter-molecular inter-actions in the solid-state: the most important contributions are from H⋯H (43.0%), H⋯O/O⋯H (27%), H⋯C/C⋯H (13.8%) and C⋯C (12.4%) contacts.

Keywords: Hirshfeld surface analysis; Schiff base; anthraquinone; crystal structure; dioxepine.