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Volume 70 
Part 1 
Pages o20-o21  
January 2014  

Received 7 November 2013
Accepted 2 December 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.009 Å
Some non-H atoms missing,
Disorder in main residue
R = 0.068
wR = 0.170
Data-to-parameter ratio = 18.1
Details
Open access

1,1'-(Diselanediylbis{[P,P-diphenyl-N-(tri­methyl­sil­yl)phospho­rimido­yl]methanylyl­idene})bis­[1,1-diphenyl-N-(tri­methyl­sil­yl)-[lambda]5-phosphanamine] pentane disolvate

aDepartment of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta T2N 1N4, Canada, and bDepartment of Chemistry, PO Box 3000, University of Oulu, 90014 Oulu, Finland
Correspondence e-mail: risto.laitinen@oulu.fi

The title compound, C62H78N4P4Se2Si4·2C5H12, is made up of two [SeC(PPh2NSiMe3)(PPh2NHSiMe3)] units related by an inversion center situated at the mid-point of the diselenide bond. It crystallized with two disordered mol­ecules of pentane used as solvent of crystallization. It is a rare example of an anti­periplanar diselenide and exhibits a long Se-Se bond of 2.4717 (8) Å. The Se-C bond length of 1.876 (5) Å is short in comparison with the range of values found for other diselenides (1.91-1.97 Å). The mol­ecule exhibits two intra­molecular N-H...N hydrogen bonds. In the crystal, there are no significant inter­molecular inter­actions present. One of the Me3Si- groups is disordered over two positions with a refined occupancy ratio of 0.708 (8):0.292 (8). The contribution of the disordered solvent to the scattering was removed with the SQUEEZE option of PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. The solvent contribution has been included in the reported mol­ecular weight and density.

Related literature

For the coordination chemistry of diselenides, see: Risto et al. (2011[Risto, M., Konu, J. & Chivers, T. (2011). Inorg. Chem. 50, 406-408.]). For examples of anti­periplanar diselenides, see: Wagner et al. (1990[Wagner, I., du Mont, W.-W., Pohl, S. & Saak, W. (1990). Chem. Ber. 123, 2325-2327.]); Dhau et al. (2011[Dhau, J. S., Singh, A. & Dhir, R. (2011). J. Organomet. Chem. 696, 2008-2013.]). For geometric parameters in organic diselenides, see: Dickson et al. (1999[Dickson, P. M., McGowan, A. D., Yearwood, B., Heeg, M. J. & Oliver, J. P. (1999). J. Organomet. Chem. 588, 42-50.]); Steudel et al. (1980[Steudel, R., Steidel, J., Pickardt, J., Schuster, F. & Reinhardt, R. (1980). Z. Naturforsch. Teil B, 35, 1378-1383.]); Schmidbaur et al. (1983[Schmidbaur, H., Zybill, C. E. & Neugebauer, D. (1983). Angew. Chem. 95, 161.]); Konu et al. (2010[Konu, J., Chivers, T. & Tuononen, H. M. (2010). Chem. Eur. J. 16, 12977-12987.]); Back & Codding (1983[Back, T. G. & Codding, P. W. (1983). Can. J. Chem. 61, 2749-2752.]); Pyykkö & Atsumi (2009[Pyykkö, P. & Atsumi, M. (2009). Chem. Eur. J. 15, 186-197.]). For the binding energies of organic dislenides, see; McDonough et al. (2005[McDonough, J. E., Weir, J. J., Carlson, M. J., Hoff, C. D., Kryatova, O. P., Rybak-Akimova, E. V., Clough, C. R. & Cummins, C. C. (2005). Inorg. Chem. 44, 3127-3136.]). For the synthesis of the reagent {Li2[C(PPh2NSiMe3)2]}, see: Kasani et al. (1999[Kasani, A., Babu, R. P. K., McDonald, R. & Cavell, R. G. (1999). Angew. Chem. Int. Ed. 38, 1483-1484.]).

[Scheme 1]

Experimental

Crystal data
  • C62H78N4P4Se2Si4·2C5H12

  • Mr = 1417.74

  • Triclinic, [P \overline 1]

  • a = 10.2500 (3) Å

  • b = 13.4420 (3) Å

  • c = 14.6670 (4) Å

  • [alpha] = 65.611 (1)°

  • [beta] = 85.525 (1)°

  • [gamma] = 76.730 (2)°

  • V = 1791.03 (8) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 1.23 mm-1

  • T = 173 K

  • 0.22 × 0.15 × 0.09 mm

Data collection
  • Nonius KappaCCD FR540C diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.773, Tmax = 0.897

  • 11811 measured reflections

  • 6257 independent reflections

  • 4902 reflections with I > 2[sigma](I)

  • Rint = 0.064

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.170

  • S = 1.04

  • 6257 reflections

  • 345 parameters

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

  • [Delta][rho]max = 0.77 e Å-3

  • [Delta][rho]min = -0.71 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...N1 0.99 (8) 1.86 (8) 2.795 (8) 156 (6)

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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: DIAMOND (Putz & Brandenburg, 2013[Putz, H. & Brandenburg, K. (2013). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2665 ).


Acknowledgements

The authors thank NSERC (Canada) and the Academy of Finland for financial support.

References

Back, T. G. & Codding, P. W. (1983). Can. J. Chem. 61, 2749-2752.  [CrossRef] [ChemPort] [Web of Science]
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Dhau, J. S., Singh, A. & Dhir, R. (2011). J. Organomet. Chem. 696, 2008-2013.  [CSD] [CrossRef] [ChemPort]
Dickson, P. M., McGowan, A. D., Yearwood, B., Heeg, M. J. & Oliver, J. P. (1999). J. Organomet. Chem. 588, 42-50.  [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kasani, A., Babu, R. P. K., McDonald, R. & Cavell, R. G. (1999). Angew. Chem. Int. Ed. 38, 1483-1484.  [Web of Science] [CrossRef] [ChemPort]
Konu, J., Chivers, T. & Tuononen, H. M. (2010). Chem. Eur. J. 16, 12977-12987.  [CSD] [CrossRef] [ChemPort] [PubMed]
McDonough, J. E., Weir, J. J., Carlson, M. J., Hoff, C. D., Kryatova, O. P., Rybak-Akimova, E. V., Clough, C. R. & Cummins, C. C. (2005). Inorg. Chem. 44, 3127-3136.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Putz, H. & Brandenburg, K. (2013). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Pyykkö, P. & Atsumi, M. (2009). Chem. Eur. J. 15, 186-197.  [PubMed]
Risto, M., Konu, J. & Chivers, T. (2011). Inorg. Chem. 50, 406-408.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Schmidbaur, H., Zybill, C. E. & Neugebauer, D. (1983). Angew. Chem. 95, 161.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Steudel, R., Steidel, J., Pickardt, J., Schuster, F. & Reinhardt, R. (1980). Z. Naturforsch. Teil B, 35, 1378-1383.
Wagner, I., du Mont, W.-W., Pohl, S. & Saak, W. (1990). Chem. Ber. 123, 2325-2327.  [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o20-o21   [ doi:10.1107/S1600536813032674 ]

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