trans-(Ethene-1,2-di­yl)bis­(diphenyl­phosphine selenide)

Phasha, Z.; Makhoba, S.; Muller, A.

doi:10.1107/S160053681105183X

Volume 68
Part 1
Page o44
January 2012

Received 14 November 2011
Accepted 1 December 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.025
wR = 0.053
Data-to-parameter ratio = 21.4
Details

trans-(Ethene-1,2-diyl)bis(diphenylphosphine selenide)

Zanele Phasha,^a ^* Sizwe Makhoba ^a and Alfred Muller ^a ^*

^aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg 2006, South Africa
Correspondence e-mail: zhphasha@uj.ac.za, mullera@uj.ac.za

In the title molecule, C₂₆H₂₂P₂Se₂, both P atoms have distorted tetrahedral environments, resulting in effective cone angles of 177 and 174°. Inversion twinning was detected and refined to a ratio of 0.35:0.65. Weak intermolecular C-HSe interactions are observed.

Related literature

For background to the steric and electronic effects of group 15 ligands, see: Roodt et al. (2003); Muller et al. (2008). For information on cone angles, see: Tolman (1977); Otto (2001).

Experimental

Crystal data

C₂₆H₂₂P₂Se₂
M_r = 554.3
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.0604 (9) Å
b = 14.3239 (14) Å
c = 17.9617 (18) Å
V = 2331.1 (4) Å³
Z = 4
Mo K radiation
= 3.32 mm^-1
T = 100 K
0.26 × 0.21 × 0.04 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.479, T_max = 0.879
14567 measured reflections
5814 independent reflections
5356 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.053
S = 1.01
5814 reflections
272 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.48 e Å^-3
Absolute structure: Flack (1983), 2517 Friedel pairs
Flack parameter: 0.354 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3Se2ⁱ	0.95	3.02	3.953 (2)	168
C21-H21Se1ⁱⁱ	0.95	3.06	3.812 (2)	138
C17-H17Se2ⁱⁱⁱ	0.95	3.01	3.885 (3)	155
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2485 ).

Acknowledgements

Research funds of the University of Johannesburg are gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.
Otto, S. (2001). Acta Cryst. C57, 793-795.
Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev. 245, 121-137.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.

organic compounds