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Volume 69 
Part 5 
Pages m242-m243  
May 2013  

Received 13 March 2013
Accepted 27 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
Disorder in main residue
R = 0.054
wR = 0.119
Data-to-parameter ratio = 14.2
Details
Open access

(RC,SFe)-1-[3,5-Bis(trifluoromethyl)phenyl]-3-{1-[2-(diphenylphosphanyl)ferrocenyl]ethyl}thiourea (unknown solvate)

aDepartment of Medicinal Chemistry, School of Pharmacy, Fourth Military Medical University, Changle Xilu 169, 710032 Xi-An, People's Republic of China, and bPharmacy Department of 323 Military Hospital, Jianshe Xilu 6, 710054 Xi-An, People's Republic of China
Correspondence e-mail: jiangru@fmmu.edu.cn

In the molecule of the the title compound, [Fe(C5H5)(C28H22F6N2PS)], the absolute configuration is RC,SFe. The dihedral angle between the trifluoromethyl-substituted phenyl ring and the thiourea plane is 41.8 (9)°. The iron atom is bound to the cyclopentadienyl rings in the typical [eta]5-manner in a close to eclipsed conformation. The crystal structure features N-H...S hydrogen bonds, with the S atom as an acceptor for both N-H groups, forming a layered arrangement parallel to (1-10). The two -CF3 groups are each disordered over two positions with refined occupancy rates for the major components of 0.66 (7) and 0.55 (5). The crystal was grown from mixed solvents (n-hexane and ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninterpretable. The solvent contribution to the structure factors was taken into account by back-Fourier transformation of all density found in the disordered solvent area using the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. The formula mass and density do not take account of the solvent.

Related literature

For an introduction to the Morita-Baylis-Hillman reaction, see: Basavaiah et al. (2010[Basavaiah, D., Reddy, B. S. & Badsara, S. S. (2010). Chem. Rev. 110, 5447-5674.]). For the synthesis of (RC,SFe)-1-(2-(diphenylphosphanyl)ferrocenyl)ethanamine and structures related to the title compound, see: Chen et al. (2006[Chen, W. P., Mbafor, W., Roberts, S. M. & Whittall, J. (2006). Tetrahedron Asymmetry, 17, 1161-1164.]). For the synthesis of the title compound, see: Sohtome et al. (2004[Sohtome, Y., Tanatani, A., Hashimoto, Y. & Nagasawa, K. (2004). Tetrahedron Lett. 45, 5589-5592.]). For refinement details concerning the use of SQUEEZE, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C28H22F6N2PS)]

  • Mr = 684.45

  • Tetragonal, P 43 21 2

  • a = 20.0898 (16) Å

  • c = 18.012 (2) Å

  • V = 7269.6 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 296 K

  • 0.37 × 0.31 × 0.25 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.818, Tmax = 0.869

  • 36567 measured reflections

  • 6472 independent reflections

  • 3487 reflections with I > 2[sigma](I)

  • Rint = 0.116

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.119

  • S = 0.95

  • 6472 reflections

  • 455 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3680 Friedel pairs

  • Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S1i 0.86 2.46 3.302 (5) 168
N2-H2...S1i 0.86 2.64 3.445 (4) 157
Symmetry code: (i) [-y+{\script{3\over 2}}, x-{\script{1\over 2}}, z-{\script{1\over 4}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2541 ).


Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20972189) for financial support.

References

Basavaiah, D., Reddy, B. S. & Badsara, S. S. (2010). Chem. Rev. 110, 5447-5674.  [ISI] [CrossRef] [ChemPort] [PubMed]
Bruker (2008). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, W. P., Mbafor, W., Roberts, S. M. & Whittall, J. (2006). Tetrahedron Asymmetry, 17, 1161-1164.  [ISI] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sohtome, Y., Tanatani, A., Hashimoto, Y. & Nagasawa, K. (2004). Tetrahedron Lett. 45, 5589-5592.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m242-m243   [ doi:10.1107/S1600536813008453 ]

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