10-Phenyl-10 H-phenoxazine-4,6-diol tetra-hydro-furan monosolvate

Aislinn C Whalen; Claudia Hernandez Brito; Kyoung H Choi; Ellen J T Warner; David A Thole; Michael R Gau; Patrick J Carroll; Mitchell R Anstey

doi:10.1107/S2414314620012766

10-Phenyl-10 H-phenoxazine-4,6-diol tetra-hydro-furan monosolvate

IUCrdata. 2020 Sep 25;5(Pt 9):x201276. doi: 10.1107/S2414314620012766. eCollection 2020 Sep.

Authors

Aislinn C Whalen¹, Claudia Hernandez Brito¹, Kyoung H Choi¹, Ellen J T Warner¹, David A Thole¹, Michael R Gau², Patrick J Carroll², Mitchell R Anstey¹

Affiliations

¹ Department of Chemistry, Davidson College, Davidson, North Carolina, USA.
² Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA.

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).

Keywords: crystal structure; hydrogen bonding; phenoxazine; tetrahydrofuran.

Grants and funding

Funding for this research was provided by: program manager Dr Imre Gyuk through the US Department of Energy, Office of Electricity, and Davidson College Faculty Study and Research (grant to ACW, CHB, DT). Sandia National Laboratories is a multi-mission laboratory managed and operated by National Technology and Engineering Solutions of Sandia, LLC., a wholly owned subsidiary of Honeywell International, Inc., for the US Department of Energy’s National Nuclear Security Administration under contract DE-NA0003525. The views expressed in this article do not necessarily represent the views of the US Department of Energy or the United States Government.