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Volume 64 
Part 12 
Page m1585  
December 2008  

Received 14 November 2008
Accepted 17 November 2008
Online 20 November 2008

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Key indicators
Single-crystal X-ray study
T = 162 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.083
Data-to-parameter ratio = 22.3
Details
Open access

(Sp)-1-Diphenylphosphanyl-2-{(S)-[2-(diphenylphosphanyl)phenyl]hydroxymethyl}ferrocene

Jan W. Bats,a* Angelino Doppiu,b Andreas Rivas Nassb and A. Stephen K. Hashmic

aInstitut für Organische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany,bUmicore AG & Co. KG, Strategic Research and Development, Precious Metals Chemistry, Rodenbacher Chaussee 4, D-63457 Hanau, Germany, and cOrganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany
Correspondence e-mail: bats@chemie.uni-frankfurt.de

The absolute configuration of the title compound, [Fe(C5H5)(C36H29OP2)], is Sp at the ferrocene group and S at the asymmetric C atom. Both P atoms have a trigonal-pyramidal conformation. There is a short intramolecular C-H...P contact with an H...P distance of 2.56 Å. The hydroxy group is involved in an intramolecular O-H...[pi]phenyl interaction. The crystal packing shows five very weak intermolecular C-H...[pi] contacts, with H...Cg distances between 3.26 and 3.39 Å (Cg is the centroid of a phenyl or cyclopentadienyl ring).

Related literature

The preparation of the title compound has been reported by Lotz & Spindler (2005[Lotz, M. & Spindler, F. (2005). WO Patent 2005/108409 A2.]). The stereochemistry of the Taniaphos ligand has been discussed by Ireland et al. (2008[Ireland, T., Grossheimann, G., Wieser-Jeunesse, C. & Knochel, P. (2008). Angew. Chem. Int. Ed. 47, 3666.]). For the synthesis of related compounds, see: Ireland et al. (2002[Ireland, T., Tappe, K., Grossheimann, G. & Knochel, P. (2002). Chem. Eur. J. 8, 843-852.]); Fukuzawa, Yamamoto, Hosaka & Kikuchi (2007[Fukuzawa, S., Yamamoto, M., Hosaka, M. & Kikuchi, S. (2007). Eur. J. Org. Chem. pp. 5540-5545.]). For the crystal structures of related compounds, see: Fukuzawa, Yamamoto & Kikuchi (2007[Fukuzawa, S., Yamamoto, M. & Kikuchi, S. (2007). J. Org. Chem. 72, 1514-1517.]); Ireland et al. (1999[Ireland, T., Grossheimann, G., Wieser-Jeunesse, C. & Knochel, P. (1999). Angew. Chem. Int. Ed. 38, 3212-3215.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C5H5)(C36H29OP2)]

  • Mr = 660.47

  • Monoclinic, P 21

  • a = 11.6111 (15) Å

  • b = 8.6154 (10) Å

  • c = 16.481 (2) Å

  • [beta] = 97.807 (12)°

  • V = 1633.4 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 162 (2) K

  • 0.40 × 0.40 × 0.32 mm
Data collection

  • Siemens SMART 1K CCD diffractometer

  • Absorption correction: numerical (SHELXTL; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.795, Tmax = 0.845

  • 25293 measured reflections

  • 9131 independent reflections

  • 7926 reflections with I > 2[sigma](I)

  • Rint = 0.051
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.083

  • S = 1.07

  • 9131 reflections

  • 410 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4069 Friedel pairs

  • Flack parameter: -0.023 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11A...P1 1.00 2.56 3.153 (2) 118
O1-H1A...C23 0.78 (3) 2.51 (3) 3.217 (3) 152 (2)

Data collection: SMART (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2123 ).

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fukuzawa, S., Yamamoto, M., Hosaka, M. & Kikuchi, S. (2007). Eur. J. Org. Chem. pp. 5540-5545.  [CSD] [CrossRef]
Fukuzawa, S., Yamamoto, M. & Kikuchi, S. (2007). J. Org. Chem. 72, 1514-1517.  [CSD] [CrossRef] [PubMed] [ChemPort]
Ireland, T., Grossheimann, G., Wieser-Jeunesse, C. & Knochel, P. (1999). Angew. Chem. Int. Ed. 38, 3212-3215.  [CrossRef] [ChemPort]
Ireland, T., Grossheimann, G., Wieser-Jeunesse, C. & Knochel, P. (2008). Angew. Chem. Int. Ed. 47, 3666.  [CrossRef]
Ireland, T., Tappe, K., Grossheimann, G. & Knochel, P. (2002). Chem. Eur. J. 8, 843-852.  [CrossRef] [ChemPort]
Lotz, M. & Spindler, F. (2005). WO Patent 2005/108409 A2.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Acta Cryst (2008). E64, m1585  [ doi:10.1107/S1600536808038294 ]

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