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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o502–o503.
Published online 2010 February 3. doi:  10.1107/S1600536810003193
PMCID: PMC2983624

(5-Ammonio­pent­yl)triphenyl­phospho­nium dibromide ethanol solvate

Abstract

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 C 3 2(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 [triangle]); Porteous et al. (2010 [triangle]); Prime et al. (2009 [triangle]). For the synthesis and applications of amino­alkyl triphenyl­phospho­nium salts, see: Issleib & Rieschel (1965 [triangle]); Keough & Grayson (1964 [triangle]); McAllister et al. (1980 [triangle]). For related structures, see: Czerwinski (1986 [triangle]); Dubourg et al. (1986 [triangle]). For a review of hydrogen-bonding networks, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o502-scheme1.jpg

Experimental

Crystal data

  • C23H28NP2+·2Br·C2H6O
  • M r = 555.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o502-efi2.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]).; software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]), enCIFer (Allen et al., 2004 [triangle]) and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

In the course of our research in mitochondrially targeted bio-active agents (Murphy & Smith, 2007), 5-ammoniopentyl triphenylphosphonium dibromide was prepared as a precursor for both a targeted thionitrite (Prime et al., 2009) and an iodoacetamide (Porteous et al., 2010). Aminoalkyl-triphenylphosphonium salts are well known (McAllister et al., 1980; Keough & Grayson, 1964; Issleib & Rieschel, 1965) but to date only dimethylamino-3-propyl triphenylphosphonium chloride (Dubourg et al., 1986) and 2-aminoethyl triphenylphosphonium bromide hydrogen bromide (Czerwinski, 1986) have been structurally characterized. The latter is clearly a dication with two bromide anions whereas the former contains a singly charged aminoalkyl triphenylphosphonium cation.

The asymmetric unit (Fig. 1) of the title compound contains one dication, two bromide ions and an ethanol of cystallization. The C(1)—P(1) and C(5)—N(1) distances [1.8020 (19)Å and 1.496 (3)Å respectively] are comparable to those published for the singly charged dimethylamino-propyl [1.802 (3)Å and 1.496 (9) Å; Dubourg et al., 1986] and dicationic 2-aminoethyl [1.796 (5)Å and 1.512 (6) Å; Czerwinski, 1986] structures, indicating that the charge and increased alkyl chain length have no appreciable effect on these parameters. The P(1)···N(1) chain is almost planar [r.m.s for all non-H atoms of 0.0716] and is in the extended form as indicated by the P—C, C—C, and C—N torsion angles [P—C(1)—C(2)—C(3) 178.55 (15)°, C(1)—C(2)—C(3)—C(4) -172.83 (17)°,C(2)—C(3)—C(4)—C(5) 173.97 (18)°, C(3)—C(4)—C(5)—N(1) 172.94 (17)°].

The hydrogen bonding network is dominated by a C23(6) chain motif (Bernstein et al., 1995) linking the dication, Br(2) and the solvent molecule (Fig. 2). The chains are comprised of N(1)—H(1C)···O(1)—H(1)···Br(2)···H(1E) interactions [N(1)···O(1) 2.790 (3) Å, O(1)···Br(2) 3.2397 (16) Å, N(1)···Br(2) 3.2814 (18) Å] which form linkages along the b axis. These chains are in turn cross-linked at longer distances by C(13)—H(13)···O(1) [C(13)···O(1) 3.584 (3) Å] and C(34)—H(34)···Br(2) [C(34)···Br(2) 3.729 (2) Å] interactions. In addition, Br(1) adopts an approximately square planar arrangement (r.m.s 0.2377) with contacts to C(1) in a trans configuration linking adjacent dications [C(1)···Br(1) 3.836 (2) Å, C(1)···Br(1) 3.886 (2) Å], and contacts to N(1)—H(1D) [N(1)···Br(1) 3.2226 (18) Å] and C(99)—H99(B) [C(99)···Br(1) 3.849 (3) Å] linking the dication and solvent.

Experimental

The title compound was prepared using a modified procedure to that published (McAllister et al., 1980). Crystalline 5-bromopentyl-amine hydrogen bromide (3 mmol) and excess triphenylphosphine (9 mmol) were heated under an inert atmosphere to 100°C and stirred for 72 h. After cooling to room temperature, the mixture was dissolved in ethanol (5 mL) and added to diethyl ether (20 mL) to precipitate the compound. Crystals of suitable quality were grown by diffusion of diethylether into an ethanolic solution of the compound.

Refinement

All H-atoms were positioned geometrically (OH allowed to rotate but not to tip) and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.97 Å, Uiso = 1.2Ueq (C) for CH2 0.96 Å, Uiso = 1.5Ueq (C) for CH3 0.89 Å, Uiso = 1.5Ueq (N) for the NH3 atoms and 0.82Å, Uiso = U1.5eq (O) for the OH atoms.

Figures

Fig. 1.
The asymmetric unit showing the atom labelling scheme. Ellipsoids are drawn at the 50% probability level with H atoms represented by spheres of arbitrary size.
Fig. 2.
The dominant hydrogen-bond contacts drawn as dashed lines forming C23(6) chains along the b axis.

Crystal data

C23H28NP2+·2Br·C2H6OF(000) = 2272
Mr = 555.32Dx = 1.417 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8129 reflections
a = 16.600 (3) Åθ = 2.6–26.2°
b = 11.947 (2) ŵ = 3.19 mm1
c = 26.257 (5) ÅT = 89 K
V = 5207.3 (18) Å3Prism, colourless
Z = 80.27 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer5323 independent reflections
Radiation source: fine-focus sealed tube4470 reflections with I > 2σ(I)
graphiteRint = 0.063
[var phi] and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)h = −20→20
Tmin = 0.379, Tmax = 0.450k = −14→14
98142 measured reflectionsl = −32→32

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0205P)2 + 4.4181P] where P = (Fo2 + 2Fc2)/3
5323 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.33 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C1−0.03376 (11)0.67164 (17)0.33559 (7)0.0157 (4)
H1A−0.0480.61740.30960.019*
H1B−0.02420.74280.31890.019*
C20.04374 (12)0.63369 (19)0.36243 (8)0.0193 (4)
H2A0.05840.68890.38790.023*
H2B0.03350.56360.37990.023*
C30.11389 (12)0.61792 (18)0.32598 (7)0.0187 (4)
H3A0.12920.68980.31180.022*
H3B0.09760.56960.29820.022*
C40.18562 (12)0.56646 (17)0.35333 (8)0.0184 (4)
H4A0.20490.61860.37890.022*
H4B0.16830.4990.37070.022*
C50.25410 (13)0.5377 (2)0.31770 (8)0.0248 (5)
H5A0.23760.47810.29490.03*
H5B0.26780.60260.29730.03*
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)
H12−0.00240.86860.38550.024*
C13−0.04125 (13)0.98715 (19)0.43472 (8)0.0249 (5)
H130.00121.03670.42970.03*
C14−0.10222 (13)1.01350 (19)0.46868 (8)0.0241 (5)
H14−0.10011.08050.48660.029*
C15−0.16599 (13)0.94130 (18)0.47611 (8)0.0224 (5)
H15−0.20680.95990.49890.027*
C16−0.16931 (12)0.84124 (17)0.44969 (8)0.0190 (4)
H16−0.21230.79250.45460.023*
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)
H22−0.18460.83780.30950.025*
C23−0.29898 (13)0.7969 (2)0.29092 (8)0.0244 (5)
H23−0.30870.85860.27020.029*
C24−0.35848 (13)0.71784 (19)0.29802 (8)0.0234 (5)
H24−0.40820.72690.28220.028*
C25−0.34490 (13)0.62523 (19)0.32838 (8)0.0241 (5)
H25−0.38480.57130.33230.029*
C26−0.27107 (12)0.61296 (18)0.35303 (8)0.0216 (5)
H26−0.26210.55160.37410.026*
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)
H32−0.11730.45280.36280.027*
C33−0.11454 (13)0.36506 (19)0.42816 (9)0.0266 (5)
H33−0.11560.29450.41320.032*
C34−0.11135 (13)0.3750 (2)0.48077 (9)0.0286 (5)
H34−0.10950.31120.5010.034*
C35−0.11098 (13)0.47944 (19)0.50297 (8)0.0270 (5)
H35−0.10940.48560.53830.032*
C36−0.11300 (12)0.57552 (18)0.47341 (8)0.0206 (5)
H36−0.11250.64570.48870.025*
N10.32613 (10)0.50107 (16)0.34763 (7)0.0234 (4)
H1C0.34410.5580.36630.035*
H1D0.36470.47870.32640.035*
H1E0.31240.44470.3680.035*
P1−0.11631 (3)0.68613 (4)0.379672 (19)0.01355 (11)
Br10.026856 (12)0.951555 (17)0.270710 (8)0.01980 (6)
Br20.273685 (13)0.321417 (17)0.436159 (8)0.02177 (6)
O10.11446 (9)0.18279 (13)0.40281 (7)0.0322 (4)
H10.15430.21380.41470.048*
C980.07010 (15)0.2606 (2)0.37272 (13)0.0492 (8)
H98A0.06940.33240.38990.059*
H98B0.01490.23490.36990.059*
C990.1044 (2)0.2760 (2)0.31995 (12)0.0539 (8)
H99A0.16010.29710.32240.081*
H99B0.0750.33350.30250.081*
H99C0.10.2070.30140.081*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0163 (10)0.0185 (11)0.0124 (9)0.0011 (8)0.0016 (8)−0.0001 (8)
C20.0157 (10)0.0247 (11)0.0174 (10)0.0028 (9)−0.0001 (8)−0.0004 (9)
C30.0181 (10)0.0232 (11)0.0147 (10)0.0009 (9)0.0008 (8)−0.0014 (9)
C40.0156 (10)0.0211 (11)0.0186 (10)0.0001 (8)0.0014 (8)−0.0027 (9)
C50.0172 (10)0.0341 (13)0.0232 (11)0.0031 (10)0.0028 (9)0.0005 (10)
C110.0168 (10)0.0140 (10)0.0128 (9)0.0009 (8)−0.0026 (8)0.0000 (8)
C120.0199 (11)0.0232 (12)0.0171 (10)−0.0005 (9)0.0033 (8)−0.0002 (9)
C130.0259 (12)0.0209 (12)0.0277 (12)−0.0086 (9)0.0014 (10)−0.0008 (9)
C140.0304 (12)0.0192 (11)0.0226 (12)0.0015 (10)−0.0053 (10)−0.0065 (9)
C150.0211 (11)0.0259 (12)0.0203 (11)0.0048 (9)0.0023 (9)−0.0041 (9)
C160.0158 (10)0.0193 (11)0.0219 (11)0.0000 (9)−0.0017 (9)0.0000 (9)
C210.0135 (9)0.0192 (11)0.0139 (10)0.0015 (8)−0.0004 (8)−0.0032 (8)
C220.0199 (11)0.0235 (11)0.0195 (11)−0.0004 (9)−0.0004 (9)0.0020 (9)
C230.0224 (11)0.0324 (13)0.0184 (11)0.0040 (10)−0.0020 (9)0.0050 (10)
C240.0164 (10)0.0393 (14)0.0145 (10)0.0052 (10)−0.0022 (8)−0.0058 (10)
C250.0168 (11)0.0310 (13)0.0244 (12)−0.0057 (9)−0.0005 (9)−0.0050 (10)
C260.0213 (11)0.0218 (11)0.0216 (11)0.0001 (9)−0.0001 (9)−0.0004 (9)
C310.0133 (9)0.0166 (10)0.0187 (10)−0.0005 (8)0.0005 (8)0.0035 (8)
C320.0240 (11)0.0210 (11)0.0227 (11)−0.0016 (9)−0.0007 (9)0.0000 (9)
C330.0250 (12)0.0166 (11)0.0383 (14)−0.0019 (9)0.0026 (10)0.0014 (10)
C340.0232 (12)0.0263 (13)0.0362 (14)0.0029 (10)0.0065 (10)0.0155 (11)
C350.0285 (12)0.0316 (14)0.0209 (11)0.0051 (10)0.0045 (10)0.0088 (10)
C360.0202 (10)0.0214 (11)0.0203 (11)0.0027 (9)0.0017 (9)0.0006 (9)
N10.0164 (9)0.0255 (10)0.0283 (10)0.0027 (8)0.0072 (8)0.0017 (8)
P10.0129 (2)0.0145 (3)0.0132 (2)0.0000 (2)−0.00030 (19)0.0003 (2)
Br10.01722 (10)0.02281 (11)0.01939 (11)−0.00049 (8)−0.00321 (8)0.00172 (9)
Br20.02484 (12)0.01773 (11)0.02274 (11)0.00034 (9)−0.00399 (9)−0.00094 (9)
O10.0239 (9)0.0302 (9)0.0424 (10)−0.0056 (7)−0.0007 (7)−0.0017 (8)
C980.0217 (13)0.0303 (15)0.095 (3)0.0039 (11)−0.0116 (15)−0.0074 (15)
C990.067 (2)0.0290 (15)0.066 (2)0.0049 (14)−0.0318 (17)0.0120 (14)

Geometric parameters (Å, °)

C1—C21.535 (3)C22—H220.93
C1—P11.8020 (19)C23—C241.380 (3)
C1—H1A0.97C23—H230.93
C1—H1B0.97C24—C251.382 (3)
C2—C31.519 (3)C24—H240.93
C2—H2A0.97C25—C261.394 (3)
C2—H2B0.97C25—H250.93
C3—C41.520 (3)C26—H260.93
C3—H3A0.97C31—C361.395 (3)
C3—H3B0.97C31—C321.400 (3)
C4—C51.512 (3)C31—P11.791 (2)
C4—H4A0.97C32—C331.380 (3)
C4—H4B0.97C32—H320.93
C5—N11.496 (3)C33—C341.387 (3)
C5—H5A0.97C33—H330.93
C5—H5B0.97C34—C351.377 (3)
C11—C121.389 (3)C34—H340.93
C11—C161.403 (3)C35—C361.386 (3)
C11—P11.797 (2)C35—H350.93
C12—C131.388 (3)C36—H360.93
C12—H120.93N1—H1C0.89
C13—C141.385 (3)N1—H1D0.89
C13—H130.93N1—H1E0.89
C14—C151.379 (3)O1—C981.425 (3)
C14—H140.93O1—H10.82
C15—C161.383 (3)C98—C991.509 (4)
C15—H150.93C98—H98A0.97
C16—H160.93C98—H98B0.97
C21—C261.391 (3)C99—H99A0.96
C21—C221.400 (3)C99—H99B0.96
C21—P11.801 (2)C99—H99C0.96
C22—C231.386 (3)
C2—C1—P1111.77 (13)C24—C23—H23119.9
C2—C1—H1A109.3C22—C23—H23119.9
P1—C1—H1A109.3C23—C24—C25120.6 (2)
C2—C1—H1B109.3C23—C24—H24119.7
P1—C1—H1B109.3C25—C24—H24119.7
H1A—C1—H1B107.9C24—C25—C26119.7 (2)
C3—C2—C1112.95 (16)C24—C25—H25120.1
C3—C2—H2A109C26—C25—H25120.1
C1—C2—H2A109C21—C26—C25120.0 (2)
C3—C2—H2B109C21—C26—H26120
C1—C2—H2B109C25—C26—H26120
H2A—C2—H2B107.8C36—C31—C32119.53 (19)
C2—C3—C4110.66 (16)C36—C31—P1122.08 (16)
C2—C3—H3A109.5C32—C31—P1118.36 (15)
C4—C3—H3A109.5C33—C32—C31120.1 (2)
C2—C3—H3B109.5C33—C32—H32119.9
C4—C3—H3B109.5C31—C32—H32119.9
H3A—C3—H3B108.1C32—C33—C34120.1 (2)
C5—C4—C3112.86 (17)C32—C33—H33120
C5—C4—H4A109C34—C33—H33120
C3—C4—H4A109C35—C34—C33120.0 (2)
C5—C4—H4B109C35—C34—H34120
C3—C4—H4B109C33—C34—H34120
H4A—C4—H4B107.8C34—C35—C36120.9 (2)
N1—C5—C4110.02 (17)C34—C35—H35119.6
N1—C5—H5A109.7C36—C35—H35119.6
C4—C5—H5A109.7C35—C36—C31119.4 (2)
N1—C5—H5B109.7C35—C36—H36120.3
C4—C5—H5B109.7C31—C36—H36120.3
H5A—C5—H5B108.2C5—N1—H1C109.5
C12—C11—C16120.08 (18)C5—N1—H1D109.5
C12—C11—P1121.51 (15)H1C—N1—H1D109.5
C16—C11—P1118.33 (15)C5—N1—H1E109.5
C13—C12—C11119.58 (19)H1C—N1—H1E109.5
C13—C12—H12120.2H1D—N1—H1E109.5
C11—C12—H12120.2C31—P1—C11111.43 (9)
C14—C13—C12120.0 (2)C31—P1—C21109.24 (9)
C14—C13—H13120C11—P1—C21106.92 (9)
C12—C13—H13120C31—P1—C1107.71 (9)
C15—C14—C13120.6 (2)C11—P1—C1110.84 (9)
C15—C14—H14119.7C21—P1—C1110.71 (9)
C13—C14—H14119.7C98—O1—H1109.5
C14—C15—C16120.0 (2)O1—C98—C99113.2 (2)
C14—C15—H15120O1—C98—H98A108.9
C16—C15—H15120C99—C98—H98A108.9
C15—C16—C11119.65 (19)O1—C98—H98B108.9
C15—C16—H16120.2C99—C98—H98B108.9
C11—C16—H16120.2H98A—C98—H98B107.8
C26—C21—C22119.74 (19)C98—C99—H99A109.5
C26—C21—P1122.32 (16)C98—C99—H99B109.5
C22—C21—P1117.84 (15)H99A—C99—H99B109.5
C23—C22—C21119.7 (2)C98—C99—H99C109.5
C23—C22—H22120.2H99A—C99—H99C109.5
C21—C22—H22120.2H99B—C99—H99C109.5
C24—C23—C22120.2 (2)
P1—C1—C2—C3178.55 (15)C34—C35—C36—C310.3 (3)
C1—C2—C3—C4−172.83 (17)C32—C31—C36—C35−0.4 (3)
C2—C3—C4—C5173.97 (18)P1—C31—C36—C35−178.57 (16)
C3—C4—C5—N1172.94 (17)C36—C31—P1—C113.0 (2)
C16—C11—C12—C130.0 (3)C32—C31—P1—C11−175.18 (16)
P1—C11—C12—C13176.62 (16)C36—C31—P1—C21−114.94 (17)
C11—C12—C13—C140.5 (3)C32—C31—P1—C2166.91 (18)
C12—C13—C14—C15−0.6 (3)C36—C31—P1—C1124.75 (17)
C13—C14—C15—C160.3 (3)C32—C31—P1—C1−53.40 (18)
C14—C15—C16—C110.2 (3)C12—C11—P1—C31119.73 (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—C230.9 (3)C16—C11—P1—C2155.74 (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—C1176.49 (15)
C22—C23—C24—C25−0.5 (3)C26—C21—P1—C31−0.2 (2)
C23—C24—C25—C261.5 (3)C22—C21—P1—C31176.17 (15)
C22—C21—C26—C250.1 (3)C26—C21—P1—C11−120.89 (17)
P1—C21—C26—C25176.38 (16)C22—C21—P1—C1155.46 (18)
C24—C25—C26—C21−1.3 (3)C26—C21—P1—C1118.28 (17)
C36—C31—C32—C330.8 (3)C22—C21—P1—C1−65.38 (18)
P1—C31—C32—C33179.03 (16)C2—C1—P1—C31−44.82 (17)
C31—C32—C33—C34−1.1 (3)C2—C1—P1—C1177.32 (16)
C32—C33—C34—C351.0 (3)C2—C1—P1—C21−164.20 (14)
C33—C34—C35—C36−0.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.891.92.790 (3)177
N1—H1D···Br1ii0.892.343.2226 (18)170
O1—H1···Br20.822.433.2397 (16)170
N1—H1E···Br20.892.43.2814 (18)168
C13—H13···O1iii0.932.663.584 (3)172
C34—H34···Br2iv0.9333.729 (2)137
C1—H1A···Br1v0.972.923.836 (2)159
C99—H99B···Br1v0.962.923.849 (3)163
C1—H1B···Br10.972.923.886 (2)173

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) x, y+1, z; (iv) x−1/2, −y+1/2, −z+1; (v) −x, y−1/2, −z+1/2.

Footnotes

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

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