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Volume 68 
Part 11 
Page o3073  
November 2012  

Received 30 July 2012
Accepted 21 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.021
wR = 0.053
Data-to-parameter ratio = 13.8
Details
Open access

Diphenyl(pyridin-2-yl)phosphane 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, C17H14NPSe, the P atom has a distorted tetrahedral environment resulting in an effective cone angle of 163°. In the crystal, C-H...Se/N/[pi] interactions are observed.

Related literature

For background to phosphorus- and selenium-containing ligands, see: 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 the free phosphine of the title compound, see: Charland et al. (1989[Charland, J.-P., Roustan, J.-L. & Ansari, N. (1989). Acta Cryst. C45, 680-681.]). For background on cone angles, see: Otto (2001[Otto, S. (2001). Acta Cryst. C57, 793-795.]); Tolman (1977[Tolman, C. A. (1977). Chem. Rev. 77, 313-348.]). For details of the conformational fit of the two molecules using Mercury, see: Macrae et al. (2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14NPSe

  • Mr = 342.22

  • Orthorhombic, P 21 21 21

  • a = 8.8092 (4) Å

  • b = 9.4066 (4) Å

  • c = 18.2661 (7) Å

  • V = 1513.61 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 4.25 mm-1

  • T = 100 K

  • 0.24 × 0.17 × 0.12 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 = 0.429, Tmax = 0.629

  • 6004 measured reflections

  • 2501 independent reflections

  • 2461 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.021

  • wR(F2) = 0.053

  • S = 0.87

  • 2501 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 992 Friedel pairs

  • Flack parameter: 0.053 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...Se1 0.95 2.87 3.427 (3) 118
C8-H8...N1 0.95 2.57 3.111 (3) 116
C14-H14...Se1 0.95 2.96 3.472 (2) 115
C5-H5...Se1i 0.95 3.07 3.923 (3) 150
C16-H16...Se1ii 0.95 3.26 3.938 (3) 130
C11-H11...Cg1iii 0.95 2.77 3.630 (3) 151
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -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. 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.]) and 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: KP2438 ).


Acknowledgements

Financial assistance from the Research Fund 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. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Charland, J.-P., Roustan, J.-L. & Ansari, N. (1989). Acta Cryst. C45, 680-681.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [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]
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, o3073  [ doi:10.1107/S160053681204007X ]

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