Received 2 August 2013
The title compound, [Fe(C44H28N4)(C6HF4O)], is a porphyrin complex with iron(III) in fivefold coordination with a tetrafluorophenolate group as the axial ligand. The Fe atom and the phenolate ligand are disordered across the porphyrin ring with the two phenolates appearing to be roughly related by a center of symmetry. The occupancies of the two phenolate groups refined to 0.788 (3) for the major component and 0.212 (3) for the minor component. The structure shows extraordinary Fe displacements of 0.488 (4) (major) and 0.673 (4) Å (minor) from the 24-atom mean plane of the porphyrin. The Fe-Np distances range from 2.063 (4) to 2.187 (6) Å and the Fe-O distances are 1.903 (5) Å for major component and 1.87 (2) Å for minor component. The four phenyl groups attached to the porphyrin ring form dihedral angles of 63.4 (4), 49.6 (4), 62.4 (4), and 63.3 (4)° (in increasing numerical order) with the three nearest C atoms of the porphyrin ring. The major and minor component phenolate groups form dihedral angles of 24.9 (4)° and 24.8 (4)°, respectively, with the four porphyrin N atoms. The FeFe distance between the two iron(III) atoms of adjacent porphyrin molecules is 6.677 (3) Å. No close intermolecular interaction was observed. The crystal studied was twinned by inversion, with a major-minor component ratio of 0.53 (3):0.47 (3).
For the function and structure of catalase, see: Nicholls et al. (2001). For the structures of other related ferric phenolate porphyrin derivatives, see: Xu et al. (2013); Chaudhary et al. (2010); Ueyama et al. (1998); Kanamori et al. (2005); Byrn et al. (1993). For the preparation of the [(TPP)Fe]2O (TPP is tetraphenylporphyrin) complex, see: Helms et al. (1986).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2492 ).
The authors wish to thank the National Science Foundation (grant CHE-1213674) and the University of Oklahoma for funds to support this research and to acquire the diffractometer and computers used in this work.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Byrn, M. P., Curtis, C. J., Hsiou, Y., Khan, S. I., Sawin, P. A., Tendick, S. K., Terzis, A. & Strouse, C. E. (1993). J. Am. Chem. Soc. 115, 9480-9497.
Chaudhary, A., Patra, R. & Rath, S. P. (2010). Eur. J. Inorg. Chem. pp. 5211-5221.
Helms, J. H., ter Haar, L. W., Hatfield, W. E., Harris, D. L., Jayaraj, K., Toney, G. E., Gold, A., Mewborn, T. D. & Pemberton, J. R. (1986). Inorg. Chem. 25, 2334-2337.
Kanamori, D., Yamada, Y., Onoda, A., Okamura, T., Adachi, S., Yamamoto, H. & Ueyama, N. (2005). Inorg. Chim. Acta, 358, 331-338.
Nicholls, P., Fita, I. & Loewen, P. C. (2001). Adv. Inorg. Chem. 51, 51-106.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ueyama, N., Nishikawa, N., Yamada, Y., Okamura, T. & Nakamura, A. (1998). Inorg. Chim. Acta, 283, 91-97.
Xu, N., Powell, D. R. & Richter-Addo, G. B. (2013). Acta Cryst. E69, m530-m531.