(5-Ammonio­pent­yl)triphenyl­phospho­nium dibromide ethanol solvate

Evans, C.

doi:10.1107/S1600536810003193

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 (C-C) = 0.003 Å
R = 0.024
wR = 0.056
Data-to-parameter ratio = 19.4
Details

(5-Ammoniopentyl)triphenylphosphonium dibromide ethanol solvate

Cameron Evans ^a ^*

^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 PN distance [7.716 (2) Å]. The ions and solvent are linked within the crystal by N-HBr, N-HO and O-HBr hydrogen-bonding interactions, forming C₃²(6) chains along the b axis, with secondary C-HBr and C-HO interactions cross-linking the chains.

Related literature

For the development and applications of mitochondrially targeted bio-active compounds, see: Murphy & Smith (2007); Porteous et al. (2010); Prime et al. (2009). For the synthesis and applications of aminoalkyl triphenylphosphonium salts, see: Issleib & Rieschel (1965); Keough & Grayson (1964); McAllister et al. (1980). For related structures, see: Czerwinski (1986); Dubourg et al. (1986). For a review of hydrogen-bonding networks, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₃H₂₈NP²⁺·2Br^-·C₂H₆O
M_r = 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 radiation
= 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) T_min = 0.379, T_max = 0.450
98142 measured reflections
5323 independent reflections
4470 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.056
S = 1.04
5323 reflections
274 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1CO1ⁱ	0.89	1.9	2.790 (3)	177
N1-H1DBr1ⁱⁱ	0.89	2.34	3.2226 (18)	170
O1-H1Br2	0.82	2.43	3.2397 (16)	170
N1-H1EBr2	0.89	2.4	3.2814 (18)	168
C13-H13O1ⁱⁱⁱ	0.93	2.66	3.584 (3)	172
C34-H34Br2^iv	0.93	3	3.729 (2)	137
C1-H1ABr1^v	0.97	2.92	3.836 (2)	159
C99-H99BBr1^v	0.96	2.92	3.849 (3)	163
C1-H1BBr1	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); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006).; software used to prepare material for publication: WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

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

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organic compounds