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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 [sigma](C-C) = 0.002 Å
R = 0.024
wR = 0.063
Data-to-parameter ratio = 23.8
Details
Open access

Dicyclohexyl[4-(dimethylamino)phenyl]phosphine selenide

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-H...Se 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[Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev. 245, 121-137.]); Muller et al. (2006[Muller, A., Meijboom, R. & Roodt, A. (2006). J. Organomet. Chem. 691, 5794-5801.], 2008[Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.]). For background on cone angles, see: Bunten et al. (2002[Bunten, K. A., Chen, L., Fernandez, A. L. & Poë, A. J. (2002). Coord. Chem. Rev. 233-234, 41-51.]); Tolman (1977[Tolman, C. A. (1977). Chem. Rev. 77, 313-348.]); Otto (2001[Otto, S. (2001). Acta Cryst. C57, 793-795.]).

[Scheme 1]

Experimental

Crystal data
  • C20H32NPSe

  • Mr = 396.4

  • Monoclinic, P 21 /c

  • a = 12.3860 (16) Å

  • b = 6.8331 (8) Å

  • c = 24.113 (3) Å

  • [beta] = 97.050 (3)°

  • V = 2025.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS, SAINT and XPREP. BrukerAXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.604, Tmax = 0.910

  • 31168 measured reflections

  • 5008 independent reflections

  • 4192 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.063

  • S = 1.02

  • 5008 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...Se1i 1.00 2.71 3.6546 (15) 157
C19-H19A...Se1i 0.99 3.04 3.8836 (18) 143
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. BrukerAXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. BrukerAXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Muller, A., Meijboom, R. & Roodt, A. (2006). J. Organomet. Chem. 691, 5794-5801.  [CSD] [CrossRef] [ChemPort]
Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.  [CSD] [CrossRef] [PubMed]
Otto, S. (2001). Acta Cryst. C57, 793-795.  [CSD] [CrossRef] [ChemPort] [details]
Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev. 245, 121-137.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2012). E68, o243  [ doi:10.1107/S1600536811054006 ]

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