Crystal structure and C-H⋯F hydrogen bonding in the fluorinated bis-benzoxazine: 3,3'-(ethane-1,2-di-yl)bis-(6-fluoro-3,4-di-hydro-2 H-1,3-benzoxazine)

Acta Crystallogr E Crystallogr Commun. 2016 Sep 30;72(Pt 10):1509-1511. doi: 10.1107/S2056989016015243. eCollection 2016 Oct 1.

Abstract

The title fluorinated bis-benzoxazine, C18H18F2N2O2, crystallizes with one half-mol-ecule in the asymmetric unit, which is completed by inversion symmetry. The fused oxazine ring adopts an approximately half-chair conformation. The two benzoxazine rings are oriented anti to one another around the central C-C bond. The dominant inter-molecular inter-action in the crystal structure is a C-H⋯F hydrogen bond between the F atoms and the axial H atoms of the OCH2N methyl-ene group in the oxazine rings of neighbouring mol-ecules. C-H⋯π contacts further stabilize the crystal packing.

Keywords: benzoxazine; crystal structure; non-conventional hydrogen bonds.