(3-Chloro­prop­yl)triphenyl­phospho­nium bromide

Kavitha, C.N.; Yathirajan, H.S.; Dayananda, A.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812042122

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 (C-C) = 0.004 Å
R = 0.034
wR = 0.107
Data-to-parameter ratio = 21.6
Details

(3-Chloropropyl)triphenylphosphonium bromide

Channappa N. Kavitha,^a Hemmige S. Yathirajan,^a A. S. Dayananda,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^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-HBr 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); Carruthers (1971); Minami et al. (1988). For related structures, see: Czerwinski & Ponnuswamy (1988a,b). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₂₁ClP⁺·Br^-
M_r = 419.71
Monoclinic, P 2₁ /c
a = 11.0708 (2) Å
b = 10.0435 (2) Å
c = 17.5740 (4) Å
= 104.973 (1)°
V = 1887.70 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.324, T_max = 0.694
18046 measured reflections
4690 independent reflections
4202 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.107
S = 1.06
4690 reflections
217 parameters
H-atom parameters constrained
_max = 1.69 e Å^-3
_min = -0.64 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31-C36 ring.

D-HA	D-H	HA	DA	D-HA
C1-H1BBr1ⁱ	0.99	2.82	3.703 (2)	149
C25-H25Br1ⁱⁱ	0.95	2.89	3.751 (3)	151
C14-H14Cg1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
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.
Czerwinski, E. W. & Ponnuswamy, M. N. (1988b). Acta Cryst. C44, 1862-1864.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Maercker, A. (1965). Org. React. 14, 270-490.
Minami, T., Shikita, S., So, S., Nakayama, M. & Yamamoto, I. (1988). J. Org. Chem. 53, 2937-2942.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds