Diphenyl(pyridin-2-yl)­phosphane selenide

Davis, W.L.; Muller, A.

doi:10.1107/S160053681204007X

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 (C-C) = 0.004 Å
R = 0.021
wR = 0.053
Data-to-parameter ratio = 13.8
Details

Diphenyl(pyridin-2-yl)phosphane selenide

Wade L. Davis ^a and Alfred Muller ^a ^*

^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-HSe/N/ [pi] interactions are observed.

Related literature

For background to phosphorus- and selenium-containing ligands, see: Muller et al. (2006, 2008). For the free phosphine of the title compound, see: Charland et al. (1989). For background on cone angles, see: Otto (2001); Tolman (1977). For details of the conformational fit of the two molecules using Mercury, see: Macrae et al. (2008); Weng et al. (2008a,b).

Experimental

Crystal data

C₁₇H₁₄NPSe
M_r = 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 radiation
= 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) T_min = 0.429, T_max = 0.629
6004 measured reflections
2501 independent reflections
2461 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.021
wR(F²) = 0.053
S = 0.87
2501 reflections
181 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.27 e Å^-3
Absolute structure: Flack (1983), 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-HA	D-H	HA	DA	D-HA
C12-H12Se1	0.95	2.87	3.427 (3)	118
C8-H8N1	0.95	2.57	3.111 (3)	116
C14-H14Se1	0.95	2.96	3.472 (2)	115
C5-H5Se1ⁱ	0.95	3.07	3.923 (3)	150
C16-H16Se1ⁱⁱ	0.95	3.26	3.938 (3)	130
C11-H11Cg1ⁱⁱⁱ	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); 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: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

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.
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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.
Otto, S. (2001). Acta Cryst. C57, 793-795.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.
Weng, Z. F., Motherwell, W. D. S., Allen, F. H. & Cole, J. M. (2008a). Acta Cryst. B64, 348-362.
Weng, Z. F., Motherwell, W. D. S. & Cole, J. M. (2008b). J. Appl. Cryst. 41, 955-957.
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organic compounds