[Journal logo]

Volume 68 
Part 11 
Page o3094  
November 2012  

Received 21 September 2012
Accepted 2 October 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.059
wR = 0.135
Data-to-parameter ratio = 19.4
Details
Open access

(2-{[2-(diphenylphosphino)phenyl]thio}phenyl)diphenylphosphine sulfide

aServicio Difracción Rayos X, Universidad Autónoma de Barcelona, 08193 Cerdanyola, Spain, and bDepartamento Química, Universidad Autónoma de Barcelona, 08193 Cerdanyola, Spain
Correspondence e-mail: angel.alvarez@uab.es

In the title compound, C36H28P2S2, the dihedral angle between the central benzene rings is 66.95 (13)°. In the crystal, molecules are linked via Car-H...[pi] and [pi]-[pi] interactions [shortest centroid-centroid distance between benzene rings = 3.897 (2) Å].

Related literature

For related structures, see: Deb & Dutta (2010[Deb, B. & Dutta, D. K. (2010). J. Mol. Catal. A Chem. 326, 21-28.]); Deb et al. (2010[Deb, B., Sarmah, P. P. & Dutta, D. K. (2010). Eur. J. Inorg. Chem. pp. 1710-1716.]); Tooke et al. (2005[Tooke, D. M., Wilting, J., Vogt, D. & Spek, A. L. (2005). Acta Cryst. E61, o2406-o2407.]); Pintado-Alba et al. (2004[Pintado-Alba, A., de la Riva, H., Nieuwhuyzen, M., Bautista, D., Raithby, P. R., Sparkes, H. A., Teat, S. J., López-de-Luzuriaga, J. M. & Lagunas, M. C. (2004). Dalton Trans. pp. 3459-3467.]). For additional information on hemilabile ligands, see: Dallanegra et al. (2012[Dallanegra, R., Chaplin, A. B. & Weller, A. S. (2012). Organometallics, 31, 2720-2728.]); Marimuthu et al. (2012[Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2012). J. Chem. Crystallogr. 42, 251-257.]); Tello-López (2010[Tello-López, I. (2010). PhD thesis, Universitat Autònoma de Barcelona, Spain.]).

[Scheme 1]

Experimental

Crystal data
  • C36H28P2S2

  • Mr = 586.64

  • Triclinic, [P \overline 1]

  • a = 10.8595 (10) Å

  • b = 11.0267 (10) Å

  • c = 13.3031 (12) Å

  • [alpha] = 76.404 (2)°

  • [beta] = 79.151 (2)°

  • [gamma] = 81.976 (2)°

  • V = 1513.1 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 296 K

  • 0.34 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.806, Tmax = 0.941

  • 10362 measured reflections

  • 6991 independent reflections

  • 4414 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.135

  • S = 0.98

  • 6991 reflections

  • 361 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C41-C46 ring.

D-H...A D-H H...A D...A D-H...A
C23-H23...Cgi 0.93 2.94 3.777 (4) 150
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2445 ).


Acknowledgements

FMC thanks the Ministerio de Educación y Ciencia of Spain for a grant.

References

Bruker (2001). SMART, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dallanegra, R., Chaplin, A. B. & Weller, A. S. (2012). Organometallics, 31, 2720-2728.  [CrossRef] [ChemPort]
Deb, B. & Dutta, D. K. (2010). J. Mol. Catal. A Chem. 326, 21-28.  [ISI] [CSD] [CrossRef] [ChemPort]
Deb, B., Sarmah, P. P. & Dutta, D. K. (2010). Eur. J. Inorg. Chem. pp. 1710-1716.  [ISI] [CSD] [CrossRef]
Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2012). J. Chem. Crystallogr. 42, 251-257.  [ISI] [CSD] [CrossRef] [ChemPort]
Pintado-Alba, A., de la Riva, H., Nieuwhuyzen, M., Bautista, D., Raithby, P. R., Sparkes, H. A., Teat, S. J., López-de-Luzuriaga, J. M. & Lagunas, M. C. (2004). Dalton Trans. pp. 3459-3467.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tello-López, I. (2010). PhD thesis, Universitat Autònoma de Barcelona, Spain.
Tooke, D. M., Wilting, J., Vogt, D. & Spek, A. L. (2005). Acta Cryst. E61, o2406-o2407.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3094  [ doi:10.1107/S1600536812041347 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.