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Volume 68 
Part 12 
Page o3484  
December 2012  

Received 15 November 2012
Accepted 24 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.066
wR = 0.194
Data-to-parameter ratio = 18.8
Details
Open access

Tris(naphthalen-1-yl)phosphane chloroform hemisolvate

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

The title compound, P(C10H7)3·0.5CHCl3, was isolated after the unsuccessful reaction of KSeCN and tris(naphthalen-1-yl)phosphane. The solvent molecule is disordered about an inversion center. The effective cone angle of the phosphine is 203°. In the crystal, weak C-H...Cl and C-H...[pi] interactions are observed.

Related literature

For background to the investigation of the steric and electronic properties of phosphorus-containing ligands, see: Otto & Roodt (2004[Otto, S. & Roodt, A. (2004). Inorg. Chim. Acta, 357, 1-10.]); 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.]); Muller et al. (2008[Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650-657.]). For background to cone angles, see: 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
  • C30H21P·0.5CHCl3

  • Mr = 472.12

  • Monoclinic, P 21 /c

  • a = 9.197 (3) Å

  • b = 14.564 (5) Å

  • c = 18.675 (5) Å

  • [beta] = 107.061 (14)°

  • V = 2391.3 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.3 mm-1

  • T = 100 K

  • 0.3 × 0.07 × 0.07 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 = 0.916, Tmax = 0.979

  • 23695 measured reflections

  • 5950 independent reflections

  • 3713 reflections with I > 2[sigma](I)

  • Rint = 0.107

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.194

  • S = 1.02

  • 5950 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.57 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C2-C7, C12-C17, C25-C30 and C1/C2/C7-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C5-H5...Cl1i 0.93 2.82 3.512 (4) 132
C18-H18...Cg1ii 0.93 2.66 3.579 (3) 170
C24-H24...Cg2iii 0.93 2.51 3.425 (3) 167
C27-H27...Cg2iv 0.93 2.69 3.612 (3) 170
C8-H8...Cg3v 0.93 2.79 3.580 (3) 143
C31-H31...Cg4vi 0.98 2.65 3.618 (6) 172
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x-1, y, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (vi) -x+1, -y+1, -z+1.

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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5561 ).


Acknowledgements

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

References

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]
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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.  [CrossRef] [ChemPort] [ISI]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3484  [ doi:10.1107/S1600536812048234 ]

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