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Volume 68 
Part 11 
Page o3115  
November 2012  

Received 4 October 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.107
Data-to-parameter ratio = 21.6
Details
Open access

(3-Chloropropyl)triphenylphosphonium bromide

aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The title compound, C21H21ClP+Br-, is the bromide salt of a mixed aryl-alkyl phosphonium cation. C-P-C angles span a range of 107.20 (10)-111.18 (10)°. The non-H atoms of the 3-chloropropyl group adopt a staggered conformation [C-C-C-Cl torsion angle: -72.0 (3)°]. In the crystal, C-H...Br contacts connect the entities of the title compound into a double zigzag chain along b. These chains are linked into a supramolecular layer lying parallel to (10-1) by C-H...[pi] interactions.

Related literature

For synthetic applications of phosphonium salts in organic chemistry, see: Maercker (1965[Maercker, A. (1965). Org. React. 14, 270-490.]); Carruthers (1971[Carruthers, W. (1971). Some Modern Methods of Organic Synthesis, pp. 81-90. Cambridge University Press.]); Minami et al. (1988[Minami, T., Shikita, S., So, S., Nakayama, M. & Yamamoto, I. (1988). J. Org. Chem. 53, 2937-2942.]). For related structures, see: Czerwinski & Ponnuswamy (1988a[Czerwinski, E. W. & Ponnuswamy, M. N. (1988a). Acta Cryst. C44, 862-865.],b[Czerwinski, E. W. & Ponnuswamy, M. N. (1988b). Acta Cryst. C44, 1862-1864.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21ClP+·Br-

  • Mr = 419.71

  • Monoclinic, P 21 /c

  • a = 11.0708 (2) Å

  • b = 10.0435 (2) Å

  • c = 17.5740 (4) Å

  • [beta] = 104.973 (1)°

  • V = 1887.70 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.40 mm-1

  • T = 200 K

  • 0.51 × 0.35 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.324, Tmax = 0.694

  • 18046 measured reflections

  • 4690 independent reflections

  • 4202 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.107

  • S = 1.06

  • 4690 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.69 e Å-3

  • [Delta][rho]min = -0.64 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31-C36 ring.

D-H...A D-H H...A D...A D-H...A
C1-H1B...Br1i 0.99 2.82 3.703 (2) 149
C25-H25...Br1ii 0.95 2.89 3.751 (3) 151
C14-H14...Cg1iii 0.95 2.68 3.623 (3) 173
Symmetry codes: (i) -x, -y+1, -z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5158 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities. HSY is grateful to R. L. Fine Chem., Bengaluru, India, for the gift sample of the title compound.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Carruthers, W. (1971). Some Modern Methods of Organic Synthesis, pp. 81-90. Cambridge University Press.
Czerwinski, E. W. & Ponnuswamy, M. N. (1988a). Acta Cryst. C44, 862-865.  [CrossRef] [details]
Czerwinski, E. W. & Ponnuswamy, M. N. (1988b). Acta Cryst. C44, 1862-1864.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [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]
Maercker, A. (1965). Org. React. 14, 270-490.  [ChemPort]
Minami, T., Shikita, S., So, S., Nakayama, M. & Yamamoto, I. (1988). J. Org. Chem. 53, 2937-2942.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3115  [ doi:10.1107/S1600536812042122 ]

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