10-Phenyl-10H-phenoxazine-4,6-diol tetrahydrofuran monosolvate

Abstract

In the crystalline state of the title solvate, C18H13NO3·C4H8O, hydrogen-bonding interactions between hydroxyl groups on a phenoxazine backbone and the tetrahydrofuran solvent are observed that suggest the ability for this compound to act as a chelating ligand. The O...O donor–acceptor distances for this hydrogen bonding are 2.7729 (15) and 2.7447 (15) Å. The three-ring backbone of the phenoxazine bends out of planarity by 18.92 (3)°, as computed using mean planes that encompass each half of the three-ring structure, with the central N and O atoms forming the line of flexion. In the crystal, a π–π stacking arrangement exists between inversion-related molecules, with a centroid-to-centroid distance of 3.6355 (11) Å. In the disordered tetrahydrofuran solvate, all atoms except oxygen were modeled over two positions, with occupancies of 0.511 (8) and 0.489 (8).

Keywords

• crystal structure
• phenoxazine
• tetrahydrofuran
• hydrogen bonding