[Journal logo]

Volume 69 
Part 10 
Pages m530-m531  
October 2013  

Received 2 August 2013
Accepted 5 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.060
wR = 0.159
Data-to-parameter ratio = 17.9
Details
Open access

(2,3,5,6-Tetrafluorophenolato)[5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato]iron(III) cyclohexane monosolvate

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(C6HF4O)(C48H36N4O4)]·C6H12, represents a five-coordinate iron(III) porphyrin complex in a square-pyramidal geometry with a tetrafluorophenolate anion as the axial ligand. The FeIII atom is displaced by 0.364 (2) Å from the 24-atom mean plane of the porphyrinate ring towards the tetrafluoro phenolate anion. The average Fe-N distance is 2.053 (2) Å and the Fe-O distance is 1.883 (2) Å. A porphyrin aryl H atom points in the general direction of the phenoxide ring. The mean plane separation between the 24-atom porphyrin planes of two adjacent porphyrin rings is ~3.7 Å, and the lateral shift is ~3.5 Å resu, ting in an Fe...Fe separation of 5.6167 (14) Å.

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 pheno porphyrin derivatives, see: 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.]). For the typical geometry parameters for high-spin ferric porphyrin complexes, see: Scheidt & Reed (1981)[Scheidt, W. R. & Reed, C. A. (1981). Chem. Rev. 81, 543-555.]. For the synthesis of [(T(p-OMe)PP)Fe]2O, 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(C6HF4O)(C48H36N4O4)]·C6H12

  • Mr = 1037.88

  • Triclinic, [P \overline 1]

  • a = 10.294 (3) Å

  • b = 15.617 (5) Å

  • c = 16.082 (5) Å

  • [alpha] = 90.984 (7)°

  • [beta] = 103.010 (8)°

  • [gamma] = 103.869 (8)°

  • V = 2438.6 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 100 K

  • 0.47 × 0.22 × 0.21 mm

Data collection
  • Bruker APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.841, Tmax = 0.924

  • 33926 measured reflections

  • 12007 independent reflections

  • 8303 reflections with I > 2[sigma](I)

  • Rint = 0.057

  • Standard reflections: ?

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.159

  • S = 1.04

  • 12007 reflections

  • 671 parameters

  • 69 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.66 e Å-3

Table 1
Selected bond lengths (Å)

Fe1-N4 2.048 (2)
Fe1-N2 2.054 (2)
Fe1-N1 2.054 (2)
Fe1-N3 2.056 (2)

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: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013; molecular graphics: XP in 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: NG5339 ).


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 (2002). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT . Bruker AXS, Inc., Madison, Wisconsin, USA.
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]
Scheidt, W. R. & Reed, C. A. (1981). Chem. Rev. 81, 543-555.  [CrossRef] [ChemPort] [Web of Science]
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]


Acta Cryst (2013). E69, m530-m531   [ doi:10.1107/S1600536813021880 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.