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Volume 68 
Part 12 
Page m1513  
December 2012  

Received 8 November 2012
Accepted 15 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.028
wR = 0.070
Data-to-parameter ratio = 36.7
Details
Open access

cis-{2,6-Bis[(di-tert-butylphosphanyl)methyl]cyclohexyl-[kappa]3P,C1,P'}chloridopalladium(II)

aCentre for Analysis and Synthesis, Department of Chemistry, Lund University, PO Box 124, S-221 00 Lund, Sweden
Correspondence e-mail: ola.wendt@chem.lu.se

The PdII atom in the title compound, [Pd(C24H49P2)Cl], has a distorted square-planar CClP2 coordination geometry with the P,C,P'-tridentate ligand forming two five-membered metallacycles. The cyclohexane ring is aligned with the PdII coordination plane due to C-H activation in an equatorial position, giving a tri-equatorial conformation of the cyclohexyl ring.

Related literature

C(sp3)-H activated (PCP)-complexes with catalytic performance in C-C coupling reactions were reported by Ohff et al. (1997[Ohff, M., Ohff, A., van der Boom, M. E. & Milstein, D. (1997). J. Am. Chem. Soc. 119, 11687-11688.]); Sjövall et al. (2002[Sjövall, S., Wendt, O. F. & Andersson, C. (2002). J. Chem. Soc. Dalton Trans. pp. 1396-1400.]); Nilsson & Wendt (2005[Nilsson, P. & Wendt, O. F. (2005). J. Organomet. Chem. 690, 4197-4202.]); Olsson & Wendt (2009[Olsson, D. & Wendt, O. F. (2009). J. Organomet. Chem. 694, 3112-3115.]). Metal complexes with (PCP)-type ligands containing an aliphatic backbone have been reported for Rh (Kuznetsov et al., 2006[Kuznetsov, V. F., Lough, A. J. & Gusev, D. G. (2006). Inorg. Chim. Acta, 359, 2806-2811.]), Ni (Castonguay et al., 2006[Castonguay, A., Sui-Seng, C., Zargarian, D. & Beauchamp, A. L. (2006). Organometallics, 25, 602-608.]; Pandarus & Zargarian, 2007[Pandarus, V. & Zargarian, D. (2007). Chem. Commun. pp. 978-980.]), Pt (Olsson et al. 2007a[Olsson, D., Arunachalampillai, A. & Wendt, O. F. (2007a). Dalton Trans. pp. 5427-5433.]), Ir (Arunachalampillai et al., 2009[Arunachalampillai, A., Olsson, D. & Wendt, O. F. (2009). Dalton Trans. pp. 8626-8630.]; Jonasson et al. 2011[Jonasson, K. J., Ahlsten, N. & Wendt, O. F. (2011). Inorg. Chim. Acta, 379, 76-80.]). The crystal structures of the bromide and iodide analogues of the title compound were determined by Sjövall et al. (2002[Sjövall, S., Wendt, O. F. & Andersson, C. (2002). J. Chem. Soc. Dalton Trans. pp. 1396-1400.]) and Olsson et al. (2007b[Olsson, D., Janse van Rensburg, J. M. & Wendt, O. F. (2007b). Acta Cryst. E63, m1969.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(C24H49P2)Cl]

  • Mr = 541.42

  • Monoclinic, P 21 /n

  • a = 11.9467 (2) Å

  • b = 14.6159 (2) Å

  • c = 15.5190 (3) Å

  • [beta] = 100.339 (2)°

  • V = 2665.80 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.93 mm-1

  • T = 293 K

  • 0.15 × 0.10 × 0.05 mm

Data collection
  • Oxford Diffraction XCalibur 3 diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.941, Tmax = 1.000

  • 26794 measured reflections

  • 9297 independent reflections

  • 6699 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.070

  • S = 0.96

  • 9297 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.28 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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: CrystalMaker (CrystalMaker, 2011[CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Oxfordshire, England. URL: www.CrystalMaker.com.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2700 ).


Acknowledgements

Financial support from the Swedish Research Council and the Knut and Alice Wallenberg Foundation is gratefully acknowledged. We also thank the Crafoord foundation for a post-doctoral grant to JMJvR.

References

Arunachalampillai, A., Olsson, D. & Wendt, O. F. (2009). Dalton Trans. pp. 8626-8630.  [CSD] [CrossRef]
Castonguay, A., Sui-Seng, C., Zargarian, D. & Beauchamp, A. L. (2006). Organometallics, 25, 602-608.  [CSD] [CrossRef] [ChemPort]
CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Oxfordshire, England. URL: www.CrystalMaker.com.
Jonasson, K. J., Ahlsten, N. & Wendt, O. F. (2011). Inorg. Chim. Acta, 379, 76-80.  [ISI] [CSD] [CrossRef] [ChemPort]
Kuznetsov, V. F., Lough, A. J. & Gusev, D. G. (2006). Inorg. Chim. Acta, 359, 2806-2811.  [ISI] [CSD] [CrossRef] [ChemPort]
Nilsson, P. & Wendt, O. F. (2005). J. Organomet. Chem. 690, 4197-4202.  [CrossRef] [ChemPort]
Ohff, M., Ohff, A., van der Boom, M. E. & Milstein, D. (1997). J. Am. Chem. Soc. 119, 11687-11688.  [CrossRef] [ChemPort] [ISI]
Olsson, D., Arunachalampillai, A. & Wendt, O. F. (2007a). Dalton Trans. pp. 5427-5433.  [CSD] [CrossRef]
Olsson, D., Janse van Rensburg, J. M. & Wendt, O. F. (2007b). Acta Cryst. E63, m1969.  [CSD] [CrossRef] [details]
Olsson, D. & Wendt, O. F. (2009). J. Organomet. Chem. 694, 3112-3115.  [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Pandarus, V. & Zargarian, D. (2007). Chem. Commun. pp. 978-980.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sjövall, S., Wendt, O. F. & Andersson, C. (2002). J. Chem. Soc. Dalton Trans. pp. 1396-1400.


Acta Cryst (2012). E68, m1513  [ doi:10.1107/S1600536812047022 ]

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