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

Alvarez-Larena, A.; Martinez-Cuevas, F.J.; Flor, T.; Real, J.

doi:10.1107/S1600536812041347

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 (C-C) = 0.005 Å
R = 0.059
wR = 0.135
Data-to-parameter ratio = 19.4
Details

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

Angel Alvarez-Larena,^a ^* Francisco J. Martinez-Cuevas,^b Teresa Flor ^b and Juli Real ^b

^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 C_ar-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 et al. (2010); Tooke et al. (2005); Pintado-Alba et al. (2004). For additional information on hemilabile ligands, see: Dallanegra et al. (2012); Marimuthu et al. (2012); Tello-López (2010).

Experimental

Crystal data

C₃₆H₂₈P₂S₂
M_r = 586.64
Triclinic, $[P \overline 1]$
a = 10.8595 (10) Å
b = 11.0267 (10) Å
c = 13.3031 (12) Å
= 76.404 (2)°
= 79.151 (2)°
= 81.976 (2)°
V = 1513.1 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.806, T_max = 0.941
10362 measured reflections
6991 independent reflections
4414 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.135
S = 0.98
6991 reflections
361 parameters
H-atom parameters not refined
_max = 0.46 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C41-C46 ring.

D-HA	D-H	HA	DA	D-HA
C23-H23Cgⁱ	0.93	2.94	3.777 (4)	150
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Deb, B. & Dutta, D. K. (2010). J. Mol. Catal. A Chem. 326, 21-28.
Deb, B., Sarmah, P. P. & Dutta, D. K. (2010). Eur. J. Inorg. Chem. pp. 1710-1716.
Marimuthu, T., Bala, M. D. & Friedrich, H. B. (2012). J. Chem. Crystallogr. 42, 251-257.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds