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

Nyamori, V.O.; Zulu, S.M.; Omondi, B.

doi:10.1107/S1600536812045400

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 (C-C) = 0.010 Å
R = 0.049
wR = 0.134
Data-to-parameter ratio = 17.2
Details

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

Vincent O. Nyamori,^a Siphesihle M. Zulu ^a and Bernard Omondi ^a ^*

^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); Nyamori & Bala (2008). For the synthesis of ferrocenyl imidazolium salts, see: Nyamori et al. (2010, 2012); Bala & Coville (2007). For applications of ferrocenyl imidazolium salts, see: Gao et al. (2004); Ornelas (2011); Coleman et al. (2005); Taylor & Licence (2012).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₀H₁₂N₂)]I
M_r = 408.06
Monoclinic, P 2₁ /c
a = 7.2745 (3) Å
b = 9.3164 (3) Å
c = 22.2744 (9) Å
= 90.927 (3)°
V = 1509.39 (10) Å³
Z = 4
Cu K radiation
= 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), based on expressions of Clark & Reid (1995)] T_min = 0.114, T_max = 0.285
6978 measured reflections
2972 independent reflections
2745 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.134
S = 1.20
2972 reflections
173 parameters
H-atom parameters constrained
_max = 2.51 e Å^-3
_min = -1.53 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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

metal-organic compounds