(5-Ammonio-pent-yl)triphenyl-phospho-nium dibromide ethanol solvate.

The alkyl-ammonium chain of the dication in the title mitochondrially targeted (5-ammonio-pent-yl)triphenyl--phos-pho-nium dibromide ethanol solvate, C(23)H(28)NP(2+)·2Br(-)·C(2)H(6)O, 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 inter-actions, forming C(3) (2)(6) chains along the b axis, with secondary C-H⋯Br and C-H⋯O inter-actions 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 = 555.32

Orthorhombic,

a = 16.600 (3) Å

b = 11.947 (2) Å

c = 26.257 (5) Å

V = 5207.3 (18) Å3

Z = 8

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.056

S = 1.04

5323 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.33 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003193/nc2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003193/nc2175Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H28NP2+·2Br−·C2H6O	F(000) = 2272
Mr = 555.32	Dx = 1.417 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8129 reflections
a = 16.600 (3) Å	θ = 2.6–26.2°
b = 11.947 (2) Å	µ = 3.19 mm−1
c = 26.257 (5) Å	T = 89 K
V = 5207.3 (18) Å3	Prism, colourless
Z = 8	0.27 × 0.25 × 0.25 mm

Bruker APEXII CCD area-detector diffractometer	5323 independent reflections
Radiation source: fine-focus sealed tube	4470 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −20→20
Tmin = 0.379, Tmax = 0.450	k = −14→14
98142 measured reflections	l = −32→32

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0205P)2 + 4.4181P] where P = (Fo2 + 2Fc2)/3
5323 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	−0.03376 (11)	0.67164 (17)	0.33559 (7)	0.0157 (4)
H1A	−0.048	0.6174	0.3096	0.019*
H1B	−0.0242	0.7428	0.3189	0.019*
C2	0.04374 (12)	0.63369 (19)	0.36243 (8)	0.0193 (4)
H2A	0.0584	0.6889	0.3879	0.023*
H2B	0.0335	0.5636	0.3799	0.023*
C3	0.11389 (12)	0.61792 (18)	0.32598 (7)	0.0187 (4)
H3A	0.1292	0.6898	0.3118	0.022*
H3B	0.0976	0.5696	0.2982	0.022*
C4	0.18562 (12)	0.56646 (17)	0.35333 (8)	0.0184 (4)
H4A	0.2049	0.6186	0.3789	0.022*
H4B	0.1683	0.499	0.3707	0.022*
C5	0.25410 (13)	0.5377 (2)	0.31770 (8)	0.0248 (5)
H5A	0.2376	0.4781	0.2949	0.03*
H5B	0.2678	0.6026	0.2973	0.03*
C11	−0.10746 (12)	0.81365 (16)	0.41553 (7)	0.0145 (4)
C12	−0.04349 (12)	0.88679 (18)	0.40813 (8)	0.0200 (5)
H12	−0.0024	0.8686	0.3855	0.024*
C13	−0.04125 (13)	0.98715 (19)	0.43472 (8)	0.0249 (5)
H13	0.0012	1.0367	0.4297	0.03*
C14	−0.10222 (13)	1.01350 (19)	0.46868 (8)	0.0241 (5)
H14	−0.1001	1.0805	0.4866	0.029*
C15	−0.16599 (13)	0.94130 (18)	0.47611 (8)	0.0224 (5)
H15	−0.2068	0.9599	0.4989	0.027*
C16	−0.16931 (12)	0.84124 (17)	0.44969 (8)	0.0190 (4)
H16	−0.2123	0.7925	0.4546	0.023*
C21	−0.21088 (11)	0.69250 (17)	0.34621 (7)	0.0155 (4)
C22	−0.22483 (13)	0.78484 (18)	0.31458 (8)	0.0210 (5)
H22	−0.1846	0.8378	0.3095	0.025*
C23	−0.29898 (13)	0.7969 (2)	0.29092 (8)	0.0244 (5)
H23	−0.3087	0.8586	0.2702	0.029*
C24	−0.35848 (13)	0.71784 (19)	0.29802 (8)	0.0234 (5)
H24	−0.4082	0.7269	0.2822	0.028*
C25	−0.34490 (13)	0.62523 (19)	0.32838 (8)	0.0241 (5)
H25	−0.3848	0.5713	0.3323	0.029*
C26	−0.27107 (12)	0.61296 (18)	0.35303 (8)	0.0216 (5)
H26	−0.2621	0.5516	0.3741	0.026*
C31	−0.11586 (11)	0.56603 (16)	0.42049 (8)	0.0162 (4)
C32	−0.11609 (13)	0.45969 (18)	0.39805 (8)	0.0225 (5)
H32	−0.1173	0.4528	0.3628	0.027*
C33	−0.11454 (13)	0.36506 (19)	0.42816 (9)	0.0266 (5)
H33	−0.1156	0.2945	0.4132	0.032*
C34	−0.11135 (13)	0.3750 (2)	0.48077 (9)	0.0286 (5)
H34	−0.1095	0.3112	0.501	0.034*
C35	−0.11098 (13)	0.47944 (19)	0.50297 (8)	0.0270 (5)
H35	−0.1094	0.4856	0.5383	0.032*
C36	−0.11300 (12)	0.57552 (18)	0.47341 (8)	0.0206 (5)
H36	−0.1125	0.6457	0.4887	0.025*
N1	0.32613 (10)	0.50107 (16)	0.34763 (7)	0.0234 (4)
H1C	0.3441	0.558	0.3663	0.035*
H1D	0.3647	0.4787	0.3264	0.035*
H1E	0.3124	0.4447	0.368	0.035*
P1	−0.11631 (3)	0.68613 (4)	0.379672 (19)	0.01355 (11)
Br1	0.026856 (12)	0.951555 (17)	0.270710 (8)	0.01980 (6)
Br2	0.273685 (13)	0.321417 (17)	0.436159 (8)	0.02177 (6)
O1	0.11446 (9)	0.18279 (13)	0.40281 (7)	0.0322 (4)
H1	0.1543	0.2138	0.4147	0.048*
C98	0.07010 (15)	0.2606 (2)	0.37272 (13)	0.0492 (8)
H98A	0.0694	0.3324	0.3899	0.059*
H98B	0.0149	0.2349	0.3699	0.059*
C99	0.1044 (2)	0.2760 (2)	0.31995 (12)	0.0539 (8)
H99A	0.1601	0.2971	0.3224	0.081*
H99B	0.075	0.3335	0.3025	0.081*
H99C	0.1	0.207	0.3014	0.081*

	U11	U22	U33	U12	U13	U23
C1	0.0163 (10)	0.0185 (11)	0.0124 (9)	0.0011 (8)	0.0016 (8)	−0.0001 (8)
C2	0.0157 (10)	0.0247 (11)	0.0174 (10)	0.0028 (9)	−0.0001 (8)	−0.0004 (9)
C3	0.0181 (10)	0.0232 (11)	0.0147 (10)	0.0009 (9)	0.0008 (8)	−0.0014 (9)
C4	0.0156 (10)	0.0211 (11)	0.0186 (10)	0.0001 (8)	0.0014 (8)	−0.0027 (9)
C5	0.0172 (10)	0.0341 (13)	0.0232 (11)	0.0031 (10)	0.0028 (9)	0.0005 (10)
C11	0.0168 (10)	0.0140 (10)	0.0128 (9)	0.0009 (8)	−0.0026 (8)	0.0000 (8)
C12	0.0199 (11)	0.0232 (12)	0.0171 (10)	−0.0005 (9)	0.0033 (8)	−0.0002 (9)
C13	0.0259 (12)	0.0209 (12)	0.0277 (12)	−0.0086 (9)	0.0014 (10)	−0.0008 (9)
C14	0.0304 (12)	0.0192 (11)	0.0226 (12)	0.0015 (10)	−0.0053 (10)	−0.0065 (9)
C15	0.0211 (11)	0.0259 (12)	0.0203 (11)	0.0048 (9)	0.0023 (9)	−0.0041 (9)
C16	0.0158 (10)	0.0193 (11)	0.0219 (11)	0.0000 (9)	−0.0017 (9)	0.0000 (9)
C21	0.0135 (9)	0.0192 (11)	0.0139 (10)	0.0015 (8)	−0.0004 (8)	−0.0032 (8)
C22	0.0199 (11)	0.0235 (11)	0.0195 (11)	−0.0004 (9)	−0.0004 (9)	0.0020 (9)
C23	0.0224 (11)	0.0324 (13)	0.0184 (11)	0.0040 (10)	−0.0020 (9)	0.0050 (10)
C24	0.0164 (10)	0.0393 (14)	0.0145 (10)	0.0052 (10)	−0.0022 (8)	−0.0058 (10)
C25	0.0168 (11)	0.0310 (13)	0.0244 (12)	−0.0057 (9)	−0.0005 (9)	−0.0050 (10)
C26	0.0213 (11)	0.0218 (11)	0.0216 (11)	0.0001 (9)	−0.0001 (9)	−0.0004 (9)
C31	0.0133 (9)	0.0166 (10)	0.0187 (10)	−0.0005 (8)	0.0005 (8)	0.0035 (8)
C32	0.0240 (11)	0.0210 (11)	0.0227 (11)	−0.0016 (9)	−0.0007 (9)	0.0000 (9)
C33	0.0250 (12)	0.0166 (11)	0.0383 (14)	−0.0019 (9)	0.0026 (10)	0.0014 (10)
C34	0.0232 (12)	0.0263 (13)	0.0362 (14)	0.0029 (10)	0.0065 (10)	0.0155 (11)
C35	0.0285 (12)	0.0316 (14)	0.0209 (11)	0.0051 (10)	0.0045 (10)	0.0088 (10)
C36	0.0202 (10)	0.0214 (11)	0.0203 (11)	0.0027 (9)	0.0017 (9)	0.0006 (9)
N1	0.0164 (9)	0.0255 (10)	0.0283 (10)	0.0027 (8)	0.0072 (8)	0.0017 (8)
P1	0.0129 (2)	0.0145 (3)	0.0132 (2)	0.0000 (2)	−0.00030 (19)	0.0003 (2)
Br1	0.01722 (10)	0.02281 (11)	0.01939 (11)	−0.00049 (8)	−0.00321 (8)	0.00172 (9)
Br2	0.02484 (12)	0.01773 (11)	0.02274 (11)	0.00034 (9)	−0.00399 (9)	−0.00094 (9)
O1	0.0239 (9)	0.0302 (9)	0.0424 (10)	−0.0056 (7)	−0.0007 (7)	−0.0017 (8)
C98	0.0217 (13)	0.0303 (15)	0.095 (3)	0.0039 (11)	−0.0116 (15)	−0.0074 (15)
C99	0.067 (2)	0.0290 (15)	0.066 (2)	0.0049 (14)	−0.0318 (17)	0.0120 (14)

C1—C2	1.535 (3)	C22—H22	0.93
C1—P1	1.8020 (19)	C23—C24	1.380 (3)
C1—H1A	0.97	C23—H23	0.93
C1—H1B	0.97	C24—C25	1.382 (3)
C2—C3	1.519 (3)	C24—H24	0.93
C2—H2A	0.97	C25—C26	1.394 (3)
C2—H2B	0.97	C25—H25	0.93
C3—C4	1.520 (3)	C26—H26	0.93
C3—H3A	0.97	C31—C36	1.395 (3)
C3—H3B	0.97	C31—C32	1.400 (3)
C4—C5	1.512 (3)	C31—P1	1.791 (2)
C4—H4A	0.97	C32—C33	1.380 (3)
C4—H4B	0.97	C32—H32	0.93
C5—N1	1.496 (3)	C33—C34	1.387 (3)
C5—H5A	0.97	C33—H33	0.93
C5—H5B	0.97	C34—C35	1.377 (3)
C11—C12	1.389 (3)	C34—H34	0.93
C11—C16	1.403 (3)	C35—C36	1.386 (3)
C11—P1	1.797 (2)	C35—H35	0.93
C12—C13	1.388 (3)	C36—H36	0.93
C12—H12	0.93	N1—H1C	0.89
C13—C14	1.385 (3)	N1—H1D	0.89
C13—H13	0.93	N1—H1E	0.89
C14—C15	1.379 (3)	O1—C98	1.425 (3)
C14—H14	0.93	O1—H1	0.82
C15—C16	1.383 (3)	C98—C99	1.509 (4)
C15—H15	0.93	C98—H98A	0.97
C16—H16	0.93	C98—H98B	0.97
C21—C26	1.391 (3)	C99—H99A	0.96
C21—C22	1.400 (3)	C99—H99B	0.96
C21—P1	1.801 (2)	C99—H99C	0.96
C22—C23	1.386 (3)
C2—C1—P1	111.77 (13)	C24—C23—H23	119.9
C2—C1—H1A	109.3	C22—C23—H23	119.9
P1—C1—H1A	109.3	C23—C24—C25	120.6 (2)
C2—C1—H1B	109.3	C23—C24—H24	119.7
P1—C1—H1B	109.3	C25—C24—H24	119.7
H1A—C1—H1B	107.9	C24—C25—C26	119.7 (2)
C3—C2—C1	112.95 (16)	C24—C25—H25	120.1
C3—C2—H2A	109	C26—C25—H25	120.1
C1—C2—H2A	109	C21—C26—C25	120.0 (2)
C3—C2—H2B	109	C21—C26—H26	120
C1—C2—H2B	109	C25—C26—H26	120
H2A—C2—H2B	107.8	C36—C31—C32	119.53 (19)
C2—C3—C4	110.66 (16)	C36—C31—P1	122.08 (16)
C2—C3—H3A	109.5	C32—C31—P1	118.36 (15)
C4—C3—H3A	109.5	C33—C32—C31	120.1 (2)
C2—C3—H3B	109.5	C33—C32—H32	119.9
C4—C3—H3B	109.5	C31—C32—H32	119.9
H3A—C3—H3B	108.1	C32—C33—C34	120.1 (2)
C5—C4—C3	112.86 (17)	C32—C33—H33	120
C5—C4—H4A	109	C34—C33—H33	120
C3—C4—H4A	109	C35—C34—C33	120.0 (2)
C5—C4—H4B	109	C35—C34—H34	120
C3—C4—H4B	109	C33—C34—H34	120
H4A—C4—H4B	107.8	C34—C35—C36	120.9 (2)
N1—C5—C4	110.02 (17)	C34—C35—H35	119.6
N1—C5—H5A	109.7	C36—C35—H35	119.6
C4—C5—H5A	109.7	C35—C36—C31	119.4 (2)
N1—C5—H5B	109.7	C35—C36—H36	120.3
C4—C5—H5B	109.7	C31—C36—H36	120.3
H5A—C5—H5B	108.2	C5—N1—H1C	109.5
C12—C11—C16	120.08 (18)	C5—N1—H1D	109.5
C12—C11—P1	121.51 (15)	H1C—N1—H1D	109.5
C16—C11—P1	118.33 (15)	C5—N1—H1E	109.5
C13—C12—C11	119.58 (19)	H1C—N1—H1E	109.5
C13—C12—H12	120.2	H1D—N1—H1E	109.5
C11—C12—H12	120.2	C31—P1—C11	111.43 (9)
C14—C13—C12	120.0 (2)	C31—P1—C21	109.24 (9)
C14—C13—H13	120	C11—P1—C21	106.92 (9)
C12—C13—H13	120	C31—P1—C1	107.71 (9)
C15—C14—C13	120.6 (2)	C11—P1—C1	110.84 (9)
C15—C14—H14	119.7	C21—P1—C1	110.71 (9)
C13—C14—H14	119.7	C98—O1—H1	109.5
C14—C15—C16	120.0 (2)	O1—C98—C99	113.2 (2)
C14—C15—H15	120	O1—C98—H98A	108.9
C16—C15—H15	120	C99—C98—H98A	108.9
C15—C16—C11	119.65 (19)	O1—C98—H98B	108.9
C15—C16—H16	120.2	C99—C98—H98B	108.9
C11—C16—H16	120.2	H98A—C98—H98B	107.8
C26—C21—C22	119.74 (19)	C98—C99—H99A	109.5
C26—C21—P1	122.32 (16)	C98—C99—H99B	109.5
C22—C21—P1	117.84 (15)	H99A—C99—H99B	109.5
C23—C22—C21	119.7 (2)	C98—C99—H99C	109.5
C23—C22—H22	120.2	H99A—C99—H99C	109.5
C21—C22—H22	120.2	H99B—C99—H99C	109.5
C24—C23—C22	120.2 (2)
P1—C1—C2—C3	178.55 (15)	C34—C35—C36—C31	0.3 (3)
C1—C2—C3—C4	−172.83 (17)	C32—C31—C36—C35	−0.4 (3)
C2—C3—C4—C5	173.97 (18)	P1—C31—C36—C35	−178.57 (16)
C3—C4—C5—N1	172.94 (17)	C36—C31—P1—C11	3.0 (2)
C16—C11—C12—C13	0.0 (3)	C32—C31—P1—C11	−175.18 (16)
P1—C11—C12—C13	176.62 (16)	C36—C31—P1—C21	−114.94 (17)
C11—C12—C13—C14	0.5 (3)	C32—C31—P1—C21	66.91 (18)
C12—C13—C14—C15	−0.6 (3)	C36—C31—P1—C1	124.75 (17)
C13—C14—C15—C16	0.3 (3)	C32—C31—P1—C1	−53.40 (18)
C14—C15—C16—C11	0.2 (3)	C12—C11—P1—C31	119.73 (17)
C12—C11—C16—C15	−0.3 (3)	C16—C11—P1—C31	−63.56 (18)
P1—C11—C16—C15	−177.07 (15)	C12—C11—P1—C21	−120.97 (17)
C26—C21—C22—C23	0.9 (3)	C16—C11—P1—C21	55.74 (18)
P1—C21—C22—C23	−175.53 (16)	C12—C11—P1—C1	−0.22 (19)
C21—C22—C23—C24	−0.7 (3)	C16—C11—P1—C1	176.49 (15)
C22—C23—C24—C25	−0.5 (3)	C26—C21—P1—C31	−0.2 (2)
C23—C24—C25—C26	1.5 (3)	C22—C21—P1—C31	176.17 (15)
C22—C21—C26—C25	0.1 (3)	C26—C21—P1—C11	−120.89 (17)
P1—C21—C26—C25	176.38 (16)	C22—C21—P1—C11	55.46 (18)
C24—C25—C26—C21	−1.3 (3)	C26—C21—P1—C1	118.28 (17)
C36—C31—C32—C33	0.8 (3)	C22—C21—P1—C1	−65.38 (18)
P1—C31—C32—C33	179.03 (16)	C2—C1—P1—C31	−44.82 (17)
C31—C32—C33—C34	−1.1 (3)	C2—C1—P1—C11	77.32 (16)
C32—C33—C34—C35	1.0 (3)	C2—C1—P1—C21	−164.20 (14)
C33—C34—C35—C36	−0.6 (3)

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

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) ; (ii) ; (iii) ; (iv) ; (v) .