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Volume 61 
Part 9 
Pages o2831-o2832  
September 2005  

Received 24 June 2005
Accepted 2 August 2005
Online 6 August 2005

[rn6058sup1]
[3d view]

[Cited in]

© International Union of Crystallography 2005

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.139
Data-to-parameter ratio = 16.1
Details

4,5-Bis[bis(diethylamino)phosphino]-9,9-dimethylxanthene

David J Adams,a John Fawcett,a Eric G. Hopea* and Alison M. Stuarta

aDepartment of Chemistry, University of Leicester, Leicester LE1 7RH, England
Correspondence e-mail: egh1@leicester.ac.uk

The structure of the title compound, C31H52N4OP2, reveals a near-planar xanthene skeleton.

Comment

Xantphos, and related bidentate ligands with the xanthene backbone, have been shown to be remarkable ligands for the rhodium-catalysed hydroformylation of long-chain alkenes, giving exceptionally high selectivity to the industrially useful linear aldehyde (linear/branched ratio = 50:1) (Kranenburg et al., 1995[Kranenburg, M., van der Burgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M. (1995). Organometallics, 14, 3081-3089.]). The title compound, (I)[link], was prepared according to the literature procedure of Goertz et al. (2001[Goertz, W., Kamer, P. C. J., van Leeuwen, P. W. N. M. & Vogt, D. (2001). Chem. Eur. J. 7, 1614-1618.]) as an intermediate in work directed towards the synthesis of perfluoroalkylated derivatives of Xantphos (Adams et al., 2004[Adams, D. J., Cole-Hamilton, D. J., Harding, D. A. J., Hope, E. G., Pogorzelec, P. & Stuart, A. M. (2004). Tetrahedron, 60, 4079-4085.]). Crystals suitable for X-ray analysis were grown from hexane solution. The bond lengths and angles within the structure are unremarkable. The molecule has a pseudo-C2 axis of symmetry through O1 and C6, such that the lone pairs on phosphorus point either in front or behind an approximately planar xanthene skeleton.

[Scheme 1]
[Figure 1]
Figure 1
The molecular structure of (I)[link], showing the atom-labelling scheme and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Experimental

The title compound was prepared according to the literature procedure of Goertz et al. (2001[Goertz, W., Kamer, P. C. J., van Leeuwen, P. W. N. M. & Vogt, D. (2001). Chem. Eur. J. 7, 1614-1618.]), Crystals suitable for X-ray analysis were grown from a hexane solution.

Crystal data

  • C31H52N4OP2

  • Mr = 558.71

  • Monoclinic, P 21 /c

  • a = 18.799 (1) Å

  • b = 11.4968 (6) Å

  • c = 15.2179 (8) Å

  • [beta] = 100.880 (1)°

  • V = 3229.9 (3) Å3

  • Z = 4

  • Dx = 1.149 Mg m-3

  • Mo K[alpha] radiation

  • Cell parameters from 6949 reflections

  • [theta] = 2.2-26.9°

  • [mu] = 0.16 mm-1

  • T = 150 (2) K

  • Block, colourless

  • 0.34 × 0.21 × 0.16 mm
Data collection

  • Bruker APEX CCD area-detector diffractometer

  • [varphi] and [omega] scans

  • Absorption correction: multi-scan(SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])Tmin = 0.93, Tmax = 0.96

  • 22958 measured reflections

  • 5685 independent reflections

  • 4653 reflections with I > 2[sigma](I)

  • Rint = 0.034

  • [theta]max = 25.0°

  • h = -22 --> 22

  • k = -13 --> 13

  • l = -18 --> 18
Refinement

  • Refinement on F2

  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.139

  • S = 1.06

  • 5685 reflections

  • 353 parameters

  • H-atom parameters constrained

  • w = 1/[[sigma]2(Fo2) + (0.0817P)2 + 0.3182P] where P = (Fo2 + 2Fc2)/3

  • ([Delta]/[sigma])max = 0.002

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

All H atoms were included in calculated positions, riding on the bonded atom [C-H = 0.95 (CH), 0.98 (CH3) and 0.99  Å (CH2)], and with Uiso(H) values set at 1.5Ueq of the bonded C atom for methyl H atoms and at 1.2Ueq for all other H atoms.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 2000[Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Acknowledgements

The authors thank the EPSRC (DJA) and the Royal Society (AMS) for financial support.

References

Adams, D. J., Cole-Hamilton, D. J., Harding, D. A. J., Hope, E. G., Pogorzelec, P. & Stuart, A. M. (2004). Tetrahedron, 60, 4079-4085. [CrossRef] [ChemPort]
Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA.
Goertz, W., Kamer, P. C. J., van Leeuwen, P. W. N. M. & Vogt, D. (2001). Chem. Eur. J. 7, 1614-1618. [CrossRef] [ChemPort]
Kranenburg, M., van der Burgt, Y. E. M., Kamer, P. C. J., van Leeuwen, P. W. N. M. (1995). Organometallics, 14, 3081-3089. [CrossRef] [ChemPort] [CSD]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Acta Cryst (2005). E61, o2831-o2832   [ doi:10.1107/S1600536805024797 ]