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Volume 69 
Part 10 
Pages m564-m565  
October 2013  

Received 2 August 2013
Accepted 20 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.008 Å
Disorder in main residue
R = 0.056
wR = 0.116
Data-to-parameter ratio = 14.1
Details
Open access

(2,3,5,6-Tetrafluorophenolato-[kappa]O)(5,10,15,20-tetraphenylporphyrinato)iron(III)

aDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Pkwy, Norman, OK 73019, USA
Correspondence e-mail: grichteraddo@ou.edu

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 Fe...Fe 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).

Related literature

For the function and structure of catalase, see: Nicholls et al. (2001[Nicholls, P., Fita, I. & Loewen, P. C. (2001). Adv. Inorg. Chem. 51, 51-106.]). For the structures of other related ferric phenolate porphyrin derivatives, see: Xu et al. (2013[Xu, N., Powell, D. R. & Richter-Addo, G. B. (2013). Acta Cryst. E69, m530-m531.]); Chaudhary et al. (2010[Chaudhary, A., Patra, R. & Rath, S. P. (2010). Eur. J. Inorg. Chem. pp. 5211-5221.]); Ueyama et al. (1998[Ueyama, N., Nishikawa, N., Yamada, Y., Okamura, T. & Nakamura, A. (1998). Inorg. Chim. Acta, 283, 91-97.]); Kanamori et al. (2005[Kanamori, D., Yamada, Y., Onoda, A., Okamura, T., Adachi, S., Yamamoto, H. & Ueyama, N. (2005). Inorg. Chim. Acta, 358, 331-338.]); Byrn et al. (1993[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.]). For the preparation of the [(TPP)Fe]2O (TPP is tetraphenylporphyrin) complex, see: Helms et al. (1986[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.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C44H28N4)(C6HF4O)]

  • Mr = 833.62

  • Monoclinic, C c

  • a = 22.287 (4) Å

  • b = 12.676 (2) Å

  • c = 13.339 (2) Å

  • [beta] = 98.510 (4)°

  • V = 3727 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.47 mm-1

  • T = 100 K

  • 0.34 × 0.16 × 0.14 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.856, Tmax = 0.937

  • 34669 measured reflections

  • 9209 independent reflections

  • 6448 reflections with I > 2[sigma](I)

  • Rint = 0.087

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.116

  • S = 1.01

  • 9209 reflections

  • 651 parameters

  • 240 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2492 ).


Acknowledgements

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.

References

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.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Chaudhary, A., Patra, R. & Rath, S. P. (2010). Eur. J. Inorg. Chem. pp. 5211-5221.  [Web of Science] [CSD] [CrossRef]
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.  [CrossRef] [ChemPort] [Web of Science]
Kanamori, D., Yamada, Y., Onoda, A., Okamura, T., Adachi, S., Yamamoto, H. & Ueyama, N. (2005). Inorg. Chim. Acta, 358, 331-338.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nicholls, P., Fita, I. & Loewen, P. C. (2001). Adv. Inorg. Chem. 51, 51-106.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Ueyama, N., Nishikawa, N., Yamada, Y., Okamura, T. & Nakamura, A. (1998). Inorg. Chim. Acta, 283, 91-97.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Xu, N., Powell, D. R. & Richter-Addo, G. B. (2013). Acta Cryst. E69, m530-m531.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, m564-m565   [ doi:10.1107/S160053681302607X ]

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