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Volume 65 
Part 9 
Page o2231  
September 2009  

Received 18 August 2009
Accepted 19 August 2009
Online 26 August 2009

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Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.102
Data-to-parameter ratio = 15.3
Details
Open access

1,1,2,2-Tetrakis(di-o-tolylphosphino)ethane

Elizabeth M. Sisler,a Karla Arias,a Danielle L. Grayb and Quinetta D. Shelbya*

aDePaul University, Department of Chemistry, 1110 West Belden Avenue, Chicago, Illinois 60614, USA, and bUniversity of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USA
Correspondence e-mail: qshelby@depaul.edu

The complete molecule of title compound, C58H58P4, is generated by a crystallographic twofold rotation axis that passes through the center of the C(methine)-C(methine) bond of length 1.582 (4) Å. The C-P bond lengths are 1.8824 (19) and 1.8991 (19) Å. The P-C-P angle of 109.69 (9)° is essentially equal to the expected value of 109.5° for a tetrahedral C atom. Although the C(methine)-P-C(aromatic) bond angles range from 102.67 (9) to 107.04 (9)°, the C(aromatic)-P-C(aromatic) bond angles of 96.72 (9) and 97.29 (9)° are significantly smaller. The steric demands of the o-tolyl groups cause deviations from the bond lengths and angles reported for its phenyl analog.

Related literature

For 1,1,2,2-tetrakis[(diphenyl)phosphino]ethane, see: Braunstein et al. (1995a[Braunstein, P., Hasselbring, R., DeCian, A. & Fischer, J. (1995a). Bull. Soc. Chim. Fr. 132, 691-695.]). For oxidative coupling of (bisphosphino)methanides, see: Braunstein et al. (1995b[Braunstein, P., Hasselbring, R., Tiripicchio, A. & Ugozzoli, F. (1995b). J. Chem. Soc. Chem. Commun. pp. 37-38.]); Schmidbaur & Deschler (1983[Schmidbaur, H. & Deschler, U. (1983). Chem. Ber. 116, 1386-1392.]).

[Scheme 1]

Experimental

Crystal data

  • C58H58P4

  • Mr = 878.92

  • Monoclinic, C 2/c

  • a = 21.8875 (11) Å

  • b = 10.9702 (6) Å

  • c = 19.691 (1) Å

  • [beta] = 90.761 (3)°

  • V = 4727.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 193 K

  • 0.42 × 0.40 × 0.24 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.976

  • 19717 measured reflections

  • 4345 independent reflections

  • 3343 reflections with I > 2[sigma](I)

  • Rint = 0.049
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.102

  • S = 1.01

  • 4345 reflections

  • 284 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT, XPREP (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) and SADABS (Bruker, 2007[Bruker (2007). SADABS and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and CrystalMaker (CrystalMaker, 1994[CrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. URL: www.CrystalMaker.com.]); software used to prepare material for publication: XCIF (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2629 ).

Acknowledgements

We thank the National Science Foundation (grant CHE-0548107) for support of this work. The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants from the NSF (CHE 95-03145 and CHE 03-43032).

References

Braunstein, P., Hasselbring, R., DeCian, A. & Fischer, J. (1995a). Bull. Soc. Chim. Fr. 132, 691-695.  [ChemPort]
Braunstein, P., Hasselbring, R., Tiripicchio, A. & Ugozzoli, F. (1995b). J. Chem. Soc. Chem. Commun. pp. 37-38.  [CrossRef] [ISI]
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SADABS and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.
CrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. URL: www.CrystalMaker.com.
Schmidbaur, H. & Deschler, U. (1983). Chem. Ber. 116, 1386-1392.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2009). E65, o2231  [ doi:10.1107/S1600536809032942 ]

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