Ferrocenyl­phospho­nic acid

Yang, B.-Z.; Xu, C.; Duan, T.-K.; Chen, Q.; Zhang, Q.-F.

doi:10.1107/S1600536811027206

Volume 67
Part 8
Page m1087
August 2011

Received 10 June 2011
Accepted 7 July 2011
Online 13 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.040
wR = 0.098
Data-to-parameter ratio = 18.4
Details

Ferrocenylphosphonic acid

Bao-Zhang Yang,^a Chao Xu,^a Tai-Ke Duan,^a Qun Chen ^b and Qian-Feng Zhang ^a,^b ^*

^aInstitute of Molecular Engineering and Applied Chemsitry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China, and ^bDepartment of Applied Chemistry, School of Petrochemical Engineering, Changzhou University, Jiangsu 213164, People's Republic of China
Correspondence e-mail: zhangqf@ahut.edu.cn

In the title compound, [Fe(C₅H₅)(C₅H₆O₃P)], the phosphate group is bonded to the ferrocene unit with a P-C bond length of 1.749 (3) Å. In the crystal, six ferrocenylphosphonic acid molecules are connected by 12 strong intermolecular O-HO hydrogen bonds, leading to the formation of a highly distorted octahedral cage. The volume of the octahedral cage is about 270 Å³.

Related literature

For background to ferrocenylphosphonates and ferrocenyl derivatives, see: Alley & Henderson (2001); Henderson & Alley (2001); Oms et al. (2004a,b, 2005).

Experimental

Crystal data

[Fe(C₅H₅)(C₅H₆O₃P)]
M_r = 266.01
Trigonal, $[R \overline 3]$
a = 19.7329 (9) Å
c = 14.7338 (4) Å
V = 4968.5 (5) Å³
Z = 18
Mo K radiation
= 1.49 mm^-1
T = 296 K
0.20 × 0.16 × 0.11 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.755, T_max = 0.853
26557 measured reflections
2500 independent reflections
1956 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.098
S = 1.03
2500 reflections
136 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.51 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.82	1.76	2.559 (3)	165
O3-H3O1ⁱⁱ	0.82	1.79	2.557 (3)	154
Symmetry codes: (i) -x+y+1, -x+1, z; (ii) $[y+{\script{1\over 3}}, -x+y+{\script{2\over 3}}, -z-{\script{1\over 3}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2442 ).

Acknowledgements

This work was supported by the Program for New Century Excellent Talents in Universities of China (NCET-08-0618).

References

Alley, S. R. & Henderson, W. (2001). J. Organomet. Chem. 637, 216-229.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Henderson, W. & Alley, S. R. (2001). Inorg. Chim. Acta, 322, 106-112.
Oms, O., Le Bideau, J., Leroux, F., van der Lee, A., Leclercq, D. & Vioux, A. (2004a). J. Am. Chem. Soc. 126, 12090-12096.
Oms, O., Maurel, F., Carré, F., Le Bideau, J., Vioux, A. & Leclercq, D. (2004b). J. Organomet. Chem. 689, 2654-2661.
Oms, O., van der Lee, A., Le Bideau, J. & Leclercq, D. (2005). Dalton Trans. pp. 1903-1909.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

metal-organic compounds