1,2-Bis(di-2-pyridylphosphino­yl)ethane

Berners-Price, S.J.; Navarro, M.; Skelton, B.W.

doi:10.1107/S1600536809004590

Volume 65
Part 3
Page o542
March 2009

Received 20 January 2009
Accepted 9 February 2009
Online 18 February 2009

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.004 Å
R = 0.052
wR = 0.112
Data-to-parameter ratio = 17.9
Details

1,2-Bis(di-2-pyridylphosphinoyl)ethane

Susan J. Berners-Price,^a Maribel Navarro ^a ⁺ and Brian W. Skelton ^a ^*

^aChemistry, School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Highway, Crawley, Perth 6009, Western Australia, Australia
Correspondence e-mail: brian.skelton@uwa.edu.au

The crystal structure of the title compound, C₂₂H₂₀N₄O₂P₂, consists of two independent half-molecules, both of which lie on crystallographic inversion centres. There are no significant differences between the two molecules.

Related literature

For the antitumour properties of metal complexes of bidentate tertiary phosphine ligands with pyridyl substituents, see: McKeage et al. (2000); Barnard & Berners-Price (2007); Liu et al. (2008). The crystal structure of the parent 1,2-bis(di-2-pyridylphosphino)ethane molecule has been determined (Jones et al., 1999). The structure of 1,2-bis(di-phenylphosphino)ethane dioxide (Calcagno et al., 2000) is similar, with the two halves of the molecule related by a pseudo-inversion centre, but this is not isomorphous with the title compound.

Experimental

Crystal data

C₂₂H₂₀N₄O₂P₂
M_r = 434.36
Triclinic, $[P \overline 1]$
a = 8.3760 (6) Å
b = 8.8496 (8) Å
c = 16.2332 (11) Å
= 105.627 (7)°
= 92.429 (5)°
= 112.559 (7)°
V = 1055.67 (16) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 110 K
0.22 × 0.10 × 0.06 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: Gaussian (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.968, T_max = 0.988
10983 measured reflections
4842 independent reflections
2698 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.112
S = 0.86
4842 reflections
271 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.34 e Å^-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2193 ).

Acknowledgements

The authors thank the Australian Research Council for financial assistance.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Barnard, P. J. & Berners-Price, S. J. (2007). Coord. Chem. Rev. 251, 1889-1902.
Calcagno, P., Kariuki, B. M., Kitchin, S. J., Robinson, J. M. A., Philp, D. & Harris, K. D. M. (2000). Chem. Eur. J. 6, 2338-2349.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Jones, N. D., MacFarlane, K. S., Smith, M. B., Schutte, R. P., Rettig, S. J. & James, B. R. (1999). Inorg. Chem. 38, 3956-3966.
Liu, J. J., Galettis, P., Farr, A., Maharaj, L., Samarasinha, H., McGechan, A. C., Baguley, B. C., Bowen, R. J., Berners-Price, S. J. & McKeage, M. J. (2008). J. Inorg. Biochem. 102, 303-310.
McKeage, M. J., Berners-Price, S. J., Galettis, P., Bowen, R. J., Brouwer, W., Ding, L., Zhuang, L. & Baguley, B. C. (2000). Cancer Chemother. Pharmacol. 46, 343-350.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds