Abstract
In the crystalline state of the title solvate, C18H13NO3·C4H8O, hydrogen-bonding inter-actions between hydroxyl groups on a phenoxazine backbone and the tetra-hydro-furan 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 mol-ecules, with a centroid-to-centroid distance of 3.6355 (11) Å. In the disordered tetra-hydro-furan solvate, all atoms except oxygen were modeled over two positions, with occupancies of 0.511 (8) and 0.489 (8).
Highlights
In the crystalline state of the title solvate, C18H13NO3ÁC4H8O, 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 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
The reported compound consists of a 10-phenyl-10Hphenoxazine backbone with two hydroxyl moieties at the 4 and 6 positions of the phenoxazine ring, and this structure was obtained as a tetrahydrofuran solvate (Fig. 2)
Summary
The reported compound consists of a 10-phenyl-10Hphenoxazine backbone with two hydroxyl moieties at the 4 and 6 positions of the phenoxazine ring, and this structure was obtained as a tetrahydrofuran solvate (Fig. 2). The interactions between O4 in the tetrahydrofuran solvent with the O2 and O3 hydroxyl groups mimic a structure that a deprotonated, dianionic form of the title compound might adopt upon complexation with a metal ion. The interaction between these molecules could be classified according to the Jeffrey model as ‘moderate, mostly electrostatic’ (Jeffrey, 1997) with donor–acceptor distances of 2.7729 (15) A (O4Á Á ÁO2) and 2.7447 (15) A (O4Á Á ÁO3) (Fig. 3, Table 1). The centroid-to-centroid separation between these two rings is 3.6355 (11) A
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