Dicyclo­hex­yl[4-(dimethyl­amino)­phen­yl]phosphine selenide

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

doi:10.1107/S1600536811054006

Volume 68
Part 1
Page o243
January 2012

Received 25 November 2011
Accepted 15 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.024
wR = 0.063
Data-to-parameter ratio = 23.8
Details

Dicyclohexyl[4-(dimethylamino)phenyl]phosphine selenide

Zanele H 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, C₂₀H₃₂NPSe, the P atom has a distorted tetrahedral environment resulting in an effective cone angle of 172°. Weak intermolecular C-HSe interactions are observed.

Related literature

For background to our investigation of the steric and electronic effects of group 15 ligands, see: Roodt et al. (2003); Muller et al. (2006, 2008). For background on cone angles, see: Bunten et al. (2002); Tolman (1977); Otto (2001).

Experimental

Crystal data

C₂₀H₃₂NPSe
M_r = 396.4
Monoclinic, P 2₁ /c
a = 12.3860 (16) Å
b = 6.8331 (8) Å
c = 24.113 (3) Å
= 97.050 (3)°
V = 2025.3 (4) Å³
Z = 4
Mo K radiation
= 1.93 mm^-1
T = 100 K
0.29 × 0.12 × 0.05 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.604, T_max = 0.910
31168 measured reflections
5008 independent reflections
4192 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.063
S = 1.02
5008 reflections
210 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15Se1ⁱ	1.00	2.71	3.6546 (15)	157
C19-H19ASe1ⁱ	0.99	3.04	3.8836 (18)	143
Symmetry code: (i) x, y+1, 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: NC2259 ).

Acknowledgements

Research funds of the University of Johannesburg is 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. BrukerAXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bunten, K. A., Chen, L., Fernandez, A. L. & Poë, A. J. (2002). Coord. Chem. Rev. 233-234, 41-51.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Muller, A., Meijboom, R. & Roodt, A. (2006). J. Organomet. Chem. 691, 5794-5801.
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