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Volume 68 
Part 12 
Page m1469  
December 2012  

Received 4 October 2012
Accepted 2 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.010 Å
R = 0.049
wR = 0.134
Data-to-parameter ratio = 17.2
Details
Open access

1-(Ferrocen-1-ylmethyl)-3-methylimidazol-3-ium iodide

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
Correspondence e-mail: owaga@ukzn.ac.za

The structure of the title compound, [Fe(C5H5)(C10H12N2)]I, consists of a 1-(ferrocen-1-ylmethyl)-3-methylimidazolium cation which is counter-balanced by an iodide anion. The cyclopentadienyl (Cp) rings of the ferrocene unit have a slightly staggered conformation skewed from an ideal eclipsed conformation by an angle of 3.5 (6)°. The interplanar angle between the Cp and the imidazole ring is 67.94 (2)°.

Related literature

For the synthesis of ferrocenyl alkyl imidazoles, see: Simenel et al. (2003[Simenel, A. A., Morozova, E. A., Kuzmenko, Y. V. & Snegur, L. V. (2003). J. Organomet. Chem. 665, 13-14.]); Nyamori & Bala (2008[Nyamori, V. O. & Bala, M. D. (2008). Acta Cryst. E64, m1451.]). For the synthesis of ferrocenyl imidazolium salts, see: Nyamori et al. (2010[Nyamori, V. O., Gumede, M. & Bala, M. D. (2010). Organomet. Chem. 695, 1126-1132.], 2012[Nyamori, V. O., Zulu, S. M. & Omondi, B. (2012). Acta Cryst. E68, m353.]); Bala & Coville (2007[Bala, M. D. & Coville, N. J. (2007). J. Organomet. Chem. 692, 709-730.]). For applications of ferrocenyl imidazolium salts, see: Gao et al. (2004[Gao, Y., Twamley, B. & Shreeve, J. M. (2004). Inorg. Chem. 43, 3406-3412.]); Ornelas (2011[Ornelas, C. (2011). New J. Chem. 35, 1973-1975.]); Coleman et al. (2005[Coleman, K. S., Turberville, S., Pascu, S. I. & Green, M. L. H. (2005). J. Organomet. Chem. 690, 653-658.]); Taylor & Licence (2012[Taylor, A. W. & Licence, P. (2012). ChemPhysChem, 13, 1917-1926.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C10H12N2)]I

  • Mr = 408.06

  • Monoclinic, P 21 /c

  • a = 7.2745 (3) Å

  • b = 9.3164 (3) Å

  • c = 22.2744 (9) Å

  • [beta] = 90.927 (3)°

  • V = 1509.39 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 23.96 mm-1

  • T = 173 K

  • 0.16 × 0.12 × 0.07 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), based on expressions of Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.114, Tmax = 0.285

  • 6978 measured reflections

  • 2972 independent reflections

  • 2745 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.134

  • S = 1.20

  • 2972 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.51 e Å-3

  • [Delta][rho]min = -1.53 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5258 ).


Acknowledgements

We thank the University of KwaZulu-Natal and the National Research Foundation (NRF) for financial support. We also thank Alex Griffin from Agilent Technology XRD for the data collection and structure solution.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bala, M. D. & Coville, N. J. (2007). J. Organomet. Chem. 692, 709-730.  [CrossRef] [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Coleman, K. S., Turberville, S., Pascu, S. I. & Green, M. L. H. (2005). J. Organomet. Chem. 690, 653-658.  [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gao, Y., Twamley, B. & Shreeve, J. M. (2004). Inorg. Chem. 43, 3406-3412.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Nyamori, V. O. & Bala, M. D. (2008). Acta Cryst. E64, m1451.  [CSD] [CrossRef] [details]
Nyamori, V. O., Gumede, M. & Bala, M. D. (2010). Organomet. Chem. 695, 1126-1132.  [ChemPort]
Nyamori, V. O., Zulu, S. M. & Omondi, B. (2012). Acta Cryst. E68, m353.  [CSD] [CrossRef] [details]
Ornelas, C. (2011). New J. Chem. 35, 1973-1975.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simenel, A. A., Morozova, E. A., Kuzmenko, Y. V. & Snegur, L. V. (2003). J. Organomet. Chem. 665, 13-14.  [CrossRef] [ChemPort]
Taylor, A. W. & Licence, P. (2012). ChemPhysChem, 13, 1917-1926.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, m1469  [ doi:10.1107/S1600536812045400 ]

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