1-(4-Ferrocenylphen­yl)-3-methyl­imidazolium iodide monohydrate

Onyancha, D.; McCleland, C.; Gerber, T.; Hosten, E.; Mayer, P.

doi:10.1107/S1600536809051216

Volume 66
Part 1
Page m49
January 2010

Received 23 November 2009
Accepted 27 November 2009
Online 12 December 2009

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.005 Å
R = 0.032
wR = 0.081
Data-to-parameter ratio = 17.1
Details

1-(4-Ferrocenylphenyl)-3-methylimidazolium iodide monohydrate

Douglas Onyancha,^a ^* Cedric McCleland,^a Thomas Gerber,^a Eric Hosten ^a and Peter Mayer ^b

^aDepartment of Chemistry, Nelson Mandela Metropolitan University, 6031 Port Elizabeth, South Africa, and ^bDepartment of Chemistry, Ludwig-Maximilians University, D-81377 München, Germany
Correspondence e-mail: douglasokerio.onyancha@nmmu.ac.za

In the title compound, [Fe(C₅H₅)(C₁₅H₁₄N₂)]I·H₂O, the benzene and imidazolium rings are twisted by 17.26 (17) and 32.53 (19)°, respectively, with respect to the [eta] ⁵-C₅H₄ plane of the ferrocenyl unit. The imidazolium ring is rotated by 48.81 (17)° with respect to the benzene ring. The packing is dominated by layers established by O-HI, C-HI and C-HO contacts and propagating along the bc plane.

Related literature

For imidazolium salts see: Nolan et al. (2007); Cheng et al. (2008); Yang et al. (2009); Bildstein et al. (1999). For the synthesis, see: Zhao et al. (2001); Koten et al. (2007). For graph-set analysis, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₅H₁₄N₂)]I·H₂O
M_r = 488.14
Monoclinic, P 2₁ /c
a = 17.3871 (7) Å
b = 7.3397 (2) Å
c = 16.9445 (6) Å
= 117.299 (5)°
V = 1921.56 (14) Å³
Z = 4
Mo K radiation
= 2.40 mm^-1
T = 200 K
0.50 × 0.39 × 0.04 mm

Data collection

Oxford Xcalibur diffractometer
Absorption correction: numerical [X-SHAPE (Stoe & Cie, 1996) and X-RED (Stoe & Cie, 1997)] T_min = 0.399, T_max = 0.901
12113 measured reflections
3885 independent reflections
3098 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.081
S = 0.97
3885 reflections
227 parameters
H-atom parameters constrained
_max = 1.28 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AI1	0.84	2.74	3.575 (3)	176
O1-H1BI1ⁱ	0.84	2.78	3.616 (3)	176
C12-H12AO1	0.95	2.39	3.277 (4)	156
C13-H13I1ⁱⁱ	0.95	3.01	3.931 (3)	163
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[ Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2694 ).

Acknowledgements

Financial support by Nelson Mandela Metropolitan University is gratefully acknowledged, as is Professor P. Klüfers for generous allocation of diffractometer time.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bildstein, B., Maluan, M., Kopacka, H., Wurst, K., Mitterbock, M., Ongania, K.-H., Opromolla, G. & Zanello, P. (1999). Organometallics, 18, 4325-4336.
Cheng, J.-P., Niu, H.-T., Yin, Z., Su, D., Niu, D., Ao, Y. & He, J. (2008). Tetrahedron, 64, 6300-6306.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Koten, G., Sperotto, E., Vries, J. & Klink, G. (2007). Tetrahedron Lett. 48, 7366-7370.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Nolan, K., Dallas, A., Kuhtz, H., Farrell, A. & Quilty, B. (2007). Tetrahedron Lett. 48, 1017-1021.
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (1996). X-SHAPE. Stoe & Cie GmbH, Darmstadt, Germany.
Stoe & Cie (1997). X-RED. Stoe & Cie GmbH, Darmstadt, Germany.
Westrip, S. P. (2009). publCIF. In preparation.
Yang, X.-D., Zeng, X.-H., Zhang, Y.-L., Qing, C., Song, W.-J., Li, L. & Zhang, H.-B. (2009). Bioorg. Med. Chem. Lett. 19, 1892-1895.
Zhao, K.-Q., Hu, P. & Xu, H. (2001). Molecules, 6, 246-247.

metal-organic compounds