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Volume 66 
Part 3 
Pages o502-o503  
March 2010  

Received 11 January 2010
Accepted 25 January 2010
Online 3 February 2010

Key indicators
Single-crystal X-ray study
T = 89 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.056
Data-to-parameter ratio = 19.4
Details
Open access

(5-Ammoniopentyl)triphenylphosphonium dibromide ethanol solvate

aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
Correspondence e-mail: cevans@chemistry.otago.ac.nz

The alkylammonium chain of the dication in the title mitochondrially targeted (5-ammoniopentyl)triphenylphosphonium dibromide ethanol solvate, C23H28NP2+·2Br-·C2H6O, is almost planar (r.m.s deviation = 0.0716 Å for all non-H atoms) and in the extended form, maximizing the P...N distance [7.716 (2) Å]. The ions and solvent are linked within the crystal by N-H...Br, N-H...O and O-H...Br hydrogen-bonding interactions, forming C32(6) chains along the b axis, with secondary C-H...Br and C-H...O interactions cross-linking the chains.

Related literature

For the development and applications of mitochondrially targeted bio-active compounds, see: Murphy & Smith (2007[Murphy, M. P. & Smith, R. A. (2007). Annu. Rev. Pharmacol. Toxicol. 47, 629-656.]); Porteous et al. (2010[Porteous, C. M., Evans, C., Ledgerwood, E., Menon, D. K., Aigbirhio, F., Smith, R. A. J. & Murphy, M. P. (2010). Biochem. Pharmacol. Submitted.]); Prime et al. (2009[Prime, T. A., Blaikie, F. H., Evans, C., Nadtochiy, S. M., James, A. M., Dahm, C. C., Vitturi, D. A., Patel, R. P., Hiley, C. R., Abakumova, I., Requejo, R., Chouchani, E. T., Hurd, T. R., Garvey, J. F., Taylor, C. T., Brookes, P. S., Smith, R. A. J. & Murphy, M. P. (2009). Proc. Natl Acad. Sci. 106, 10764-10769.]). For the synthesis and applications of aminoalkyl triphenylphosphonium salts, see: Issleib & Rieschel (1965[Issleib, K. & Rieschel, R. (1965). Chem. Ber. 98, 2086-2090.]); Keough & Grayson (1964[Keough, P. & Grayson, M. (1964). J. Org. Chem. 29, 631-635.]); McAllister et al. (1980[McAllister, P. R., Dotson, M. J., Grim, S. O. & Hillman, G. R. (1980). J. Med. Chem. 23, 862-865.]). For related structures, see: Czerwinski (1986[Czerwinski, E. W. (1986). Acta Cryst. C42, 236-239.]); Dubourg et al. (1986[Dubourg, A., De Castro Dantas, T. N., Klaébé, A. & Declercq, J.-P. (1986). Acta Cryst. C42, 112-114.]). For a review of hydrogen-bonding networks, see: 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
  • C23H28NP2+·2Br-·C2H6O

  • Mr = 555.32

  • Orthorhombic, P b c a

  • a = 16.600 (3) Å

  • b = 11.947 (2) Å

  • c = 26.257 (5) Å

  • V = 5207.3 (18) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 3.19 mm-1

  • T = 89 K

  • 0.27 × 0.25 × 0.25 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.379, Tmax = 0.450

  • 98142 measured reflections

  • 5323 independent reflections

  • 4470 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.056

  • S = 1.04

  • 5323 reflections

  • 274 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1C...O1i 0.89 1.9 2.790 (3) 177
N1-H1D...Br1ii 0.89 2.34 3.2226 (18) 170
O1-H1...Br2 0.82 2.43 3.2397 (16) 170
N1-H1E...Br2 0.89 2.4 3.2814 (18) 168
C13-H13...O1iii 0.93 2.66 3.584 (3) 172
C34-H34...Br2iv 0.93 3 3.729 (2) 137
C1-H1A...Br1v 0.97 2.92 3.836 (2) 159
C99-H99B...Br1v 0.96 2.92 3.849 (3) 163
C1-H1B...Br1 0.97 2.92 3.886 (2) 173
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) x, y+1, z; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (v) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).; software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2175 ).


Acknowledgements

The author thanks Professor Rob Smith for access to materials and laboratory facilities, and the BBSRC for funding (Contract No. BB/D020786/1).

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
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]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Czerwinski, E. W. (1986). Acta Cryst. C42, 236-239.  [CrossRef] [details]
Dubourg, A., De Castro Dantas, T. N., Klaébé, A. & Declercq, J.-P. (1986). Acta Cryst. C42, 112-114.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Issleib, K. & Rieschel, R. (1965). Chem. Ber. 98, 2086-2090.  [CrossRef] [ChemPort]
Keough, P. & Grayson, M. (1964). J. Org. Chem. 29, 631-635.  [CrossRef]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
McAllister, P. R., Dotson, M. J., Grim, S. O. & Hillman, G. R. (1980). J. Med. Chem. 23, 862-865.  [CrossRef] [ChemPort] [PubMed] [ISI]
Murphy, M. P. & Smith, R. A. (2007). Annu. Rev. Pharmacol. Toxicol. 47, 629-656.  [ISI] [CrossRef] [PubMed] [ChemPort]
Porteous, C. M., Evans, C., Ledgerwood, E., Menon, D. K., Aigbirhio, F., Smith, R. A. J. & Murphy, M. P. (2010). Biochem. Pharmacol. Submitted.
Prime, T. A., Blaikie, F. H., Evans, C., Nadtochiy, S. M., James, A. M., Dahm, C. C., Vitturi, D. A., Patel, R. P., Hiley, C. R., Abakumova, I., Requejo, R., Chouchani, E. T., Hurd, T. R., Garvey, J. F., Taylor, C. T., Brookes, P. S., Smith, R. A. J. & Murphy, M. P. (2009). Proc. Natl Acad. Sci. 106, 10764-10769.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). publCIF. In preparation.


Acta Cryst (2010). E66, o502-o503   [ doi:10.1107/S1600536810003193 ]

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