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Volume 68 
Part 11 
Pages o3153-o3154  
November 2012  

Received 27 September 2012
Accepted 11 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 21.7
Details
Open access

[4-(Dimethylamino)phenyl]diphenylphosphine selenide

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

In the title compound, C20H20NPSe, the P atom lies in a distorted tetrahedral environment. The Tolman cone angle is 157° indicating steric crowding at this atom. In the crystal, weak C-H...Se interactions create linked dimeric units and C-H...[pi] interactions are also observed.

Related literature

For investigations into the steric and electronic properties of phosphorus containing ligands, see: Roodt et al. (2003[Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev. 245, 121-137.]); Otto & Roodt (2004[Otto, S. & Roodt, A. (2004). Inorg. Chim. Acta, 357, 1-10.]); Muller et al. (2008[Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.]); Cowley & Damasco (1971[Cowley, A. H. & Damasco, M. C. (1971). J. Am. Chem. Soc. 93, 6815-6821.]); Allen & Taylor (1982[Allen, D. W. & Taylor, B. F. (1982). J. Chem. Soc. Dalton Trans. pp. 51-54.]); Allen et al. (1985[Allen, D. W., Nowel, I. W. & Taylor, B. F. (1985). J. Chem. Soc. Dalton Trans. pp. 2505-2508.]). For the free phosphine related to the title compound, see: Dreissig & Plieth (1972[Dreissig, W. & Plieth, K. (1972). Z. Kristallogr. 135, 294-307.]). For the oxide analogue of the title compound, see: Lynch et al. (2003[Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (2003). Aust. J. Chem. 56, 1135-1139.]). For the related phosphine selenide, see: Phasha et al. (2012[Phasha, Z. H., Makhoba, S. & Muller, A. (2012). Acta Cryst. E68, o243.]). For cone angles, see: Tolman (1977[Tolman, C. A. (1977). Chem. Rev. 77, 313-348.]); Otto (2001[Otto, S. (2001). Acta Cryst. C57, 793-795.]). For details on the conformational fit of molecules using Mercury, see: Macrae et al. (2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); Weng et al. (2008a[Weng, Z. F., Motherwell, W. D. S., Allen, F. H. & Cole, J. M. (2008a). Acta Cryst. B64, 348-362.],b[Weng, Z. F., Motherwell, W. D. S. & Cole, J. M. (2008b). J. Appl. Cryst. 41, 955-957.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For background on Bent's rule, see: Bent (1961[Bent, H. A. (1961). Chem. Rev. 61, 275-311.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20NPSe

  • Mr = 384.3

  • Monoclinic, P 21 /c

  • a = 12.1757 (13) Å

  • b = 10.6173 (11) Å

  • c = 17.5211 (14) Å

  • [beta] = 128.098 (5)°

  • V = 1782.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.20 mm-1

  • T = 100 K

  • 0.22 × 0.11 × 0.09 mm

Data collection
  • Bruker APEX DUO 4K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.643, Tmax = 0.827

  • 31924 measured reflections

  • 4553 independent reflections

  • 3798 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.06

  • 4553 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.72 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 refer to the centroids of the C7-C12 and C13-C18 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C20-H20A...Se1i 0.98 3.25 3.833 (3) 120
C20-H20C...Se1ii 0.98 3.07 3.707 (3) 124
C4-H4...Cg1iii 0.95 2.66 3.476 (4) 145
C15-H15...Cg1iv 0.95 2.90 3.699 (3) 142
C19-H19B...Cg2v 0.98 2.79 3.627 (3) 144
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) -x, -y, -z; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) & 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: YK2075 ).


Acknowledgements

Financial assistance from the Research Fund of the University of Johannesburg is gratefully acknowledged.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, D. W., Nowel, I. W. & Taylor, B. F. (1985). J. Chem. Soc. Dalton Trans. pp. 2505-2508.  [CrossRef]
Allen, D. W. & Taylor, B. F. (1982). J. Chem. Soc. Dalton Trans. pp. 51-54.  [CrossRef]
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]
Bent, H. A. (1961). Chem. Rev. 61, 275-311.  [CrossRef] [ChemPort] [ISI]
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.
Cowley, A. H. & Damasco, M. C. (1971). J. Am. Chem. Soc. 93, 6815-6821.  [CrossRef] [ChemPort] [ISI]
Dreissig, W. & Plieth, K. (1972). Z. Kristallogr. 135, 294-307.  [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (2003). Aust. J. Chem. 56, 1135-1139.  [ISI] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
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]
Otto, S. & Roodt, A. (2004). Inorg. Chim. Acta, 357, 1-10.  [ISI] [CrossRef] [ChemPort]
Phasha, Z. H., Makhoba, S. & Muller, A. (2012). Acta Cryst. E68, o243.  [CSD] [CrossRef] [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]
Weng, Z. F., Motherwell, W. D. S., Allen, F. H. & Cole, J. M. (2008a). Acta Cryst. B64, 348-362.  [ISI] [CrossRef] [details]
Weng, Z. F., Motherwell, W. D. S. & Cole, J. M. (2008b). J. Appl. Cryst. 41, 955-957.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3153-o3154   [ doi:10.1107/S1600536812042602 ]

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