4-Fluoro­anilinium tetra­chloridoferrate(III) 18-crown-6 clathrate

Ge, J.-Z.; Zhao, M.-M.

doi:10.1107/S160053681002009X

Volume 66
Part 7
Page m739
July 2010

Received 15 May 2010
Accepted 27 May 2010
Online 5 June 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R = 0.078
wR = 0.271
Data-to-parameter ratio = 21.5
Details

4-Fluoroanilinium tetrachloridoferrate(III) 18-crown-6 clathrate

Jia-Zhen Ge ^a ^* and Min-Min Zhao ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: gjz@seu.edu.cn

The reaction of 4-fluoroaniline hydrochloride, 18-crown-6 and ferric chloride in methanolic solution yields the title compound, (C₆H₇FN)[FeCl₄]·C₁₂H₂₄O₆, which has an unusual supramolecular structure. N-HO hydrogen-bonding interactions between the NH₃⁺ substituents of the 4-fluoroanilinium cations and the O atoms of the crown ether molecules result in a rotator-stator-like structure.

Related literature

For a related 18-crown-6 clathrate, see: Fender et al. (2002). For the ferroelectric properties of selected transition metal complexes, see: Fu et al. (2007); Ye et al. (2009); Zhang et al. (2009).

Experimental

Crystal data

(C₆H₇FN)[FeCl₄]·C₁₂H₂₄O₆
M_r = 574.09
Monoclinic, P 2₁ /c
a = 11.45 (1) Å
b = 24.14 (2) Å
c = 9.719 (9) Å
= 96.82 (2)°
V = 2667 (4) Å³
Z = 4
Mo K radiation
= 1.00 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.818, T_max = 0.818
26978 measured reflections
6039 independent reflections
3173 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.078
wR(F²) = 0.271
S = 1.07
6039 reflections
281 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1CO4ⁱ	0.89	1.98	2.868 (6)	176
N1-H1DO6ⁱ	0.89	2.04	2.924 (6)	173
N1-H1EO2ⁱ	0.89	1.98	2.840 (6)	162
Symmetry code: (i) x, y, z-1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2203 ).

Acknowledgements

The authors thank the start-up projects for Postdoctoral Research Funds of Southeast University (grant No. 1112000047) and the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Fender, N. S., Kahwa, I. A. & Fronczek, F. R. (2002). J. Solid State Chem. 163, 286-293.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Fu, D. W., Song, Y. M., Wang, G. X., Ye, Q., Xiong, R. G., Akutagawa, T., Nakamura, T., Chan, P. W. H. & Huang, S. P. (2007). J. Am. Chem. Soc. 129, 5346-5347.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ye, H. Y., Fu, D. W., Zhang, Y., Zhang, W., Xiong, R. G. & Huang, S. P. (2009). J. Am. Chem. Soc. 131, 42-43.
Zhang, W., Cheng, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. P. (2009). J. Am. Chem. Soc. 131, 12544-12545.

metal-organic compounds