Tris(naphthalen-1-yl)phosphane chloro­form hemisolvate

Davis, W.L.; Muller, A.

doi:10.1107/S1600536812048234

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 (C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.066
wR = 0.194
Data-to-parameter ratio = 18.8
Details

Tris(naphthalen-1-yl)phosphane chloroform hemisolvate

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

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-HCl 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); Cowley & Damasco (1971); Allen & Taylor (1982); Allen et al. (1985); Muller et al. (2008). For background to cone angles, see: Tolman (1977); Otto (2001).

Experimental

Crystal data

C₃₀H₂₁P·0.5CHCl₃
M_r = 472.12
Monoclinic, P 2₁ /c
a = 9.197 (3) Å
b = 14.564 (5) Å
c = 18.675 (5) Å
= 107.061 (14)°
V = 2391.3 (13) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.916, T_max = 0.979
23695 measured reflections
5950 independent reflections
3713 reflections with I > 2(I)
R_int = 0.107

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.194
S = 1.02
5950 reflections
316 parameters
H-atom parameters constrained
_max = 0.87 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C5-H5Cl1ⁱ	0.93	2.82	3.512 (4)	132
C18-H18Cg1ⁱⁱ	0.93	2.66	3.579 (3)	170
C24-H24Cg2ⁱⁱⁱ	0.93	2.51	3.425 (3)	167
C27-H27Cg2^iv	0.93	2.69	3.612 (3)	170
C8-H8Cg3^v	0.93	2.79	3.580 (3)	143
C31-H31Cg4^vi	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); 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, 2012).

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.
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Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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Otto, S. (2001). Acta Cryst. C57, 793-795.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tolman, C. A. (1977). Chem. Rev. 77, 313-348.
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organic compounds