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Acta Cryst. (2011). E67, m872    [ doi:10.1107/S1600536811021295 ]

Trimethylphenylammonium [mu]-bromido-bis[dibromidobis(4-bromobenzyl)stannate(IV)]

T. C. Keng, K. M. Lo and S. W. Ng

Abstract top

In the title salt, [C6H5N(CH3)3][Sn2Br5(C7H6Br)4], the SnIV atoms of the dinuclear anion are bridged by a Br atom; the Sn-Brbridge bond lengths are 2.9818 (5) and 3.0470 (5) Å. Both Sn atoms show a distorted cis-trigonal-bipyramidal coordination geometry that is distorted towards a square pyramid. In the crystal, weak C-H...[pi] interactions occur between anions and cations.

Comment top

We have reported the products of the reaction of phenyltrimethylammonium tribromide with triorganotin halides. The products are bis(ammonium) hexahalogenostannates as all tin-carbon bonds are cleaved. When heating was avoided, only one organic radical is cleaved, as found for the reaction of tris(p-bromobenzyl)tin bromide. In the salt, C6H5N(CH3)3+ [Sn2Br5(C7H6Br)4]- (Scheme I), the SnIV atoms of the dinuclear anion is bridged by a Br atom. The Sn atom shows cis-trigonal bipyramidal coordination but the geometry is distorted towards a square pyramid (Fig. 1).

The [Sn2Br5(C7H6Br)4]- anion is known only in a report on the ferrocenium derivative (Razak et al., 1998).

Related literature top

For the ferrocenium salt, see: Razak et al. (1998).

Experimental top

Tris(p-bromobenzyl)tin bromide (0.35 g,0.5 mmol) and phenyltrimethylammonium tribromide (0.20 g, 0.6 mmol) were dissolved in a 1:1 mixture of chloroform and ethanol (100 ml). The mixture was stirred at room temperature for half an hour, after which it was filtered. The filtrate when allowed to evaporate yielded yellow crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The final difference Fourier map had a peak in the vicinity of Sn2.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C6H5N(CH3)3+ [Sn2Br5(C7H6Br)4]- at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Trimethylphenylammonium µ-bromido-bis[dibromidobis(4-bromobenzyl)stannate(IV)] top
Crystal data top
(C9H14N)[Sn2Br5(C7H6Br)4]F(000) = 2728
Mr = 1453.25Dx = 2.240 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9891 reflections
a = 12.7274 (2) Åθ = 2.2–28.3°
b = 25.5126 (3) ŵ = 9.53 mm−1
c = 13.5135 (2) ÅT = 100 K
β = 100.8540 (7)°Block, yellow
V = 4309.46 (11) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		9908 independent reflections
Radiation source: fine-focus sealed tube7661 reflections with I > 2σ(I)
graphiteRint = 0.042
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→16
Tmin = 0.369, Tmax = 1.000k = −33→33
39991 measured reflectionsl = −17→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0341P)2 + 7.3533P]
where P = (Fo2 + 2Fc2)/3
9908 reflections(Δ/σ)max = 0.001
442 parametersΔρmax = 1.91 e Å−3
0 restraintsΔρmin = −0.57 e Å−3
Crystal data top
(C9H14N)[Sn2Br5(C7H6Br)4]V = 4309.46 (11) Å3
Mr = 1453.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.7274 (2) ŵ = 9.53 mm−1
b = 25.5126 (3) ÅT = 100 K
c = 13.5135 (2) Å0.25 × 0.20 × 0.20 mm
β = 100.8540 (7)°
Data collection top
Bruker SMART APEX
diffractometer		9908 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7661 reflections with I > 2σ(I)
Tmin = 0.369, Tmax = 1.000Rint = 0.042
39991 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.075Δρmax = 1.91 e Å−3
S = 1.01Δρmin = −0.57 e Å−3
9908 reflectionsAbsolute structure: ?
442 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.81786 (2)0.337729 (12)0.94404 (2)0.01448 (7)
Sn20.70478 (2)0.337048 (12)0.54752 (2)0.01443 (7)
Br10.86566 (3)0.287857 (17)1.11616 (3)0.01834 (10)
Br20.92320 (3)0.418920 (17)0.99980 (3)0.01920 (10)
Br30.61807 (4)0.52309 (2)1.27020 (4)0.03240 (13)
Br41.38301 (4)0.36296 (2)0.97869 (4)0.02558 (11)
Br50.59378 (4)0.416124 (18)0.48842 (3)0.02092 (10)
Br60.75532 (4)0.394348 (18)0.74303 (3)0.02003 (10)
Br70.66142 (3)0.287356 (18)0.37302 (3)0.01896 (10)
Br80.14869 (4)0.36492 (2)0.56486 (4)0.02844 (12)
Br90.93742 (4)0.516322 (19)0.22308 (4)0.02822 (12)
N10.7352 (3)0.56483 (15)0.7507 (3)0.0189 (8)
C10.6533 (3)0.35253 (18)0.9558 (3)0.0170 (9)
H1A0.61320.36440.88970.020*
H1B0.62030.31950.97340.020*
C20.6447 (3)0.39277 (17)1.0331 (3)0.0148 (9)
C30.6342 (4)0.44532 (19)1.0054 (4)0.0232 (10)
H30.63240.45480.93720.028*
C40.6263 (4)0.48384 (19)1.0753 (4)0.0261 (11)
H40.61850.51961.05550.031*
C50.6299 (3)0.46979 (18)1.1740 (4)0.0207 (10)
C60.6394 (3)0.41858 (18)1.2051 (3)0.0192 (9)
H60.64110.40961.27360.023*
C70.6466 (3)0.38005 (17)1.1337 (3)0.0171 (9)
H70.65300.34441.15400.021*
C80.9143 (3)0.28879 (17)0.8651 (3)0.0167 (9)
H8A0.90820.25170.88480.020*
H8B0.88820.29170.79150.020*
C91.0284 (3)0.30581 (17)0.8906 (3)0.0151 (9)
C101.0675 (3)0.34458 (18)0.8336 (3)0.0185 (9)
H101.02180.35920.77650.022*
C111.1727 (3)0.36190 (18)0.8598 (3)0.0195 (9)
H111.19910.38830.82130.023*
C121.2381 (3)0.34023 (17)0.9423 (3)0.0176 (9)
C131.2024 (4)0.30160 (18)0.9994 (3)0.0196 (10)
H131.24890.28681.05570.024*
C141.0973 (4)0.28488 (17)0.9725 (3)0.0189 (9)
H141.07180.25841.01140.023*
C150.8704 (3)0.35093 (18)0.5378 (3)0.0181 (9)
H15A0.90960.36330.60400.022*
H15B0.90330.31760.52200.022*
C160.8814 (3)0.39068 (18)0.4590 (3)0.0169 (9)
C170.8833 (4)0.44396 (19)0.4823 (4)0.0253 (11)
H170.87500.45480.54770.030*
C180.8968 (4)0.48114 (19)0.4118 (4)0.0260 (11)
H180.89740.51740.42800.031*
C190.9096 (3)0.46504 (18)0.3176 (3)0.0195 (9)
C200.9056 (3)0.41296 (17)0.2910 (3)0.0188 (9)
H200.91260.40270.22500.023*
C210.8913 (3)0.37575 (17)0.3617 (3)0.0160 (9)
H210.88810.33970.34390.019*
C220.6133 (3)0.28391 (16)0.6225 (3)0.0147 (9)
H22A0.61490.24840.59340.018*
H22B0.64560.28200.69500.018*
C230.5001 (3)0.30229 (16)0.6105 (3)0.0148 (9)
C240.4648 (4)0.32903 (18)0.6869 (3)0.0204 (10)
H240.51270.33500.74880.025*
C250.3601 (4)0.34747 (18)0.6745 (3)0.0211 (10)
H250.33590.36490.72830.025*
C260.2930 (3)0.34026 (18)0.5848 (3)0.0188 (9)
C270.3249 (3)0.31357 (19)0.5063 (3)0.0204 (10)
H270.27680.30820.44430.025*
C280.4287 (3)0.29492 (18)0.5205 (3)0.0189 (9)
H280.45170.27660.46730.023*
C290.7368 (3)0.62369 (18)0.7491 (3)0.0181 (9)
C300.8351 (4)0.64841 (18)0.7540 (3)0.0223 (10)
H300.89860.62820.75940.027*
C310.8400 (4)0.70240 (19)0.7508 (3)0.0229 (10)
H310.90700.71930.75340.027*
C320.7478 (4)0.7321 (2)0.7439 (3)0.0246 (10)
H320.75120.76920.74080.030*
C330.6507 (4)0.70722 (19)0.7416 (3)0.0231 (10)
H330.58780.72760.73860.028*
C340.6438 (4)0.65296 (19)0.7435 (3)0.0207 (10)
H340.57680.63610.74100.025*
C350.6252 (4)0.54242 (19)0.7476 (4)0.0286 (11)
H35A0.57700.55480.68690.043*
H35B0.59820.55380.80740.043*
H35C0.62890.50410.74640.043*
C360.7741 (4)0.5443 (2)0.6599 (4)0.0306 (12)
H36A0.72830.55780.59860.046*
H36B0.77140.50600.65970.046*
H36C0.84790.55590.66200.046*
C370.8053 (4)0.5446 (2)0.8456 (4)0.0284 (11)
H37A0.77940.55820.90450.043*
H37B0.87910.55630.84800.043*
H37C0.80300.50620.84610.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01219 (14)0.01765 (16)0.01408 (14)−0.00085 (11)0.00372 (11)−0.00305 (12)
Sn20.01197 (14)0.01826 (16)0.01353 (14)0.00009 (11)0.00359 (11)0.00278 (12)
Br10.0195 (2)0.0207 (2)0.0148 (2)0.00046 (18)0.00314 (17)0.00112 (17)
Br20.0196 (2)0.0195 (2)0.0182 (2)−0.00415 (18)0.00277 (18)−0.00331 (18)
Br30.0352 (3)0.0244 (3)0.0403 (3)−0.0022 (2)0.0139 (2)−0.0141 (2)
Br40.0146 (2)0.0282 (3)0.0343 (3)−0.00233 (19)0.0054 (2)−0.0006 (2)
Br50.0218 (2)0.0210 (2)0.0195 (2)0.00481 (18)0.00270 (18)0.00459 (18)
Br60.0251 (2)0.0195 (2)0.0153 (2)−0.00074 (18)0.00311 (18)−0.00001 (18)
Br70.0199 (2)0.0226 (2)0.0144 (2)−0.00124 (18)0.00344 (17)−0.00165 (18)
Br80.0162 (2)0.0280 (3)0.0426 (3)0.00379 (19)0.0092 (2)0.0007 (2)
Br90.0336 (3)0.0189 (2)0.0348 (3)0.0009 (2)0.0132 (2)0.0083 (2)
N10.0157 (18)0.0190 (19)0.0212 (19)−0.0002 (15)0.0014 (16)0.0007 (17)
C10.010 (2)0.025 (2)0.016 (2)−0.0002 (17)0.0036 (17)−0.0018 (18)
C20.0079 (19)0.021 (2)0.017 (2)0.0017 (17)0.0058 (17)0.0010 (18)
C30.023 (2)0.025 (3)0.023 (2)0.004 (2)0.007 (2)0.004 (2)
C40.029 (3)0.015 (2)0.037 (3)0.003 (2)0.013 (2)0.005 (2)
C50.015 (2)0.020 (2)0.028 (2)−0.0036 (18)0.0064 (19)−0.010 (2)
C60.015 (2)0.024 (2)0.018 (2)0.0029 (18)0.0037 (18)−0.0017 (19)
C70.017 (2)0.016 (2)0.020 (2)0.0037 (17)0.0061 (18)0.0018 (18)
C80.020 (2)0.017 (2)0.014 (2)0.0030 (18)0.0065 (18)−0.0061 (18)
C90.017 (2)0.015 (2)0.015 (2)0.0003 (17)0.0058 (17)−0.0042 (17)
C100.017 (2)0.022 (2)0.016 (2)0.0059 (18)0.0028 (18)0.0047 (19)
C110.017 (2)0.020 (2)0.023 (2)0.0021 (18)0.0103 (19)0.0045 (19)
C120.014 (2)0.017 (2)0.023 (2)−0.0004 (17)0.0049 (18)−0.0039 (19)
C130.021 (2)0.024 (2)0.014 (2)0.0036 (19)0.0054 (18)0.0017 (19)
C140.023 (2)0.018 (2)0.017 (2)0.0006 (18)0.0068 (19)0.0034 (18)
C150.015 (2)0.024 (2)0.015 (2)0.0011 (18)0.0020 (17)0.0021 (18)
C160.010 (2)0.022 (2)0.020 (2)−0.0021 (17)0.0047 (17)−0.0014 (19)
C170.024 (2)0.027 (3)0.027 (2)−0.006 (2)0.012 (2)−0.010 (2)
C180.029 (3)0.016 (2)0.035 (3)−0.003 (2)0.012 (2)−0.006 (2)
C190.014 (2)0.017 (2)0.029 (2)−0.0005 (17)0.0073 (19)0.0048 (19)
C200.018 (2)0.017 (2)0.021 (2)0.0003 (18)0.0030 (19)−0.0015 (18)
C210.017 (2)0.012 (2)0.019 (2)0.0015 (17)0.0053 (18)−0.0006 (17)
C220.015 (2)0.014 (2)0.016 (2)−0.0024 (17)0.0037 (17)0.0048 (17)
C230.014 (2)0.014 (2)0.018 (2)−0.0047 (16)0.0046 (17)0.0018 (17)
C240.017 (2)0.026 (3)0.018 (2)−0.0038 (19)0.0021 (18)−0.0047 (19)
C250.022 (2)0.019 (2)0.025 (2)−0.0045 (19)0.011 (2)−0.0086 (19)
C260.011 (2)0.020 (2)0.027 (2)0.0004 (17)0.0046 (18)0.001 (2)
C270.016 (2)0.029 (3)0.016 (2)−0.0005 (19)0.0036 (18)−0.001 (2)
C280.016 (2)0.025 (2)0.017 (2)−0.0013 (19)0.0049 (18)−0.0014 (19)
C290.019 (2)0.019 (2)0.016 (2)0.0001 (18)0.0046 (18)0.0028 (18)
C300.015 (2)0.024 (3)0.026 (2)0.0026 (19)0.0021 (19)0.001 (2)
C310.025 (2)0.027 (3)0.015 (2)−0.005 (2)0.0020 (19)0.001 (2)
C320.033 (3)0.023 (2)0.017 (2)0.001 (2)0.003 (2)−0.001 (2)
C330.028 (3)0.025 (3)0.016 (2)0.007 (2)0.004 (2)−0.001 (2)
C340.017 (2)0.028 (3)0.017 (2)0.0012 (19)0.0031 (18)−0.0010 (19)
C350.024 (3)0.023 (3)0.038 (3)−0.002 (2)0.004 (2)0.005 (2)
C360.043 (3)0.023 (3)0.028 (3)0.001 (2)0.011 (2)−0.004 (2)
C370.025 (3)0.032 (3)0.027 (3)0.006 (2)−0.001 (2)0.007 (2)
Geometric parameters (Å, °) top
Sn1—C12.163 (4)C15—H15A0.9900
Sn1—C82.167 (4)C15—H15B0.9900
Sn1—Br12.6203 (5)C16—C171.394 (6)
Sn1—Br22.5051 (5)C16—C211.398 (6)
Sn1—Br63.0470 (5)C17—C181.378 (7)
Sn2—C152.165 (4)C17—H170.9500
Sn2—C222.160 (4)C18—C191.375 (6)
Sn2—Br62.9818 (5)C18—H180.9500
Sn2—Br52.5057 (5)C19—C201.375 (6)
Sn2—Br72.6423 (5)C20—C211.383 (6)
Br3—C51.906 (4)C20—H200.9500
Br4—C121.908 (4)C21—H210.9500
Br8—C261.911 (4)C22—C231.494 (6)
Br9—C191.908 (4)C22—H22A0.9900
N1—C361.502 (6)C22—H22B0.9900
N1—C291.502 (6)C23—C241.381 (6)
N1—C351.505 (6)C23—C281.387 (6)
N1—C371.509 (6)C24—C251.394 (6)
C1—C21.483 (6)C24—H240.9500
C1—H1A0.9900C25—C261.358 (6)
C1—H1B0.9900C25—H250.9500
C2—C31.391 (6)C26—C271.385 (6)
C2—C71.393 (6)C27—C281.383 (6)
C3—C41.380 (7)C27—H270.9500
C3—H30.9500C28—H280.9500
C4—C51.374 (7)C29—C341.389 (6)
C4—H40.9500C29—C301.391 (6)
C5—C61.371 (6)C30—C311.380 (7)
C6—C71.392 (6)C30—H300.9500
C6—H60.9500C31—C321.384 (7)
C7—H70.9500C31—H310.9500
C8—C91.493 (6)C32—C331.384 (7)
C8—H8A0.9900C32—H320.9500
C8—H8B0.9900C33—C341.388 (7)
C9—C141.383 (6)C33—H330.9500
C9—C101.402 (6)C34—H340.9500
C10—C111.391 (6)C35—H35A0.9800
C10—H100.9500C35—H35B0.9800
C11—C121.375 (6)C35—H35C0.9800
C11—H110.9500C36—H36A0.9800
C12—C131.380 (6)C36—H36B0.9800
C13—C141.387 (6)C36—H36C0.9800
C13—H130.9500C37—H37A0.9800
C14—H140.9500C37—H37B0.9800
C15—C161.496 (6)C37—H37C0.9800
C1—Sn1—C8141.50 (16)H15A—C15—H15B107.9
C1—Sn1—Br2107.72 (12)C17—C16—C21118.5 (4)
C8—Sn1—Br2107.69 (12)C17—C16—C15120.0 (4)
C1—Sn1—Br194.91 (12)C21—C16—C15121.5 (4)
C8—Sn1—Br195.68 (12)C18—C17—C16120.9 (4)
Br2—Sn1—Br196.480 (17)C18—C17—H17119.5
C1—Sn1—Br683.61 (12)C16—C17—H17119.5
C8—Sn1—Br684.91 (12)C19—C18—C17119.1 (4)
Br2—Sn1—Br684.913 (16)C19—C18—H18120.5
Br1—Sn1—Br6178.233 (17)C17—C18—H18120.5
C15—Sn2—C22138.41 (16)C20—C19—C18121.7 (4)
C22—Sn2—Br5109.48 (11)C20—C19—Br9119.3 (3)
C15—Sn2—Br5110.23 (12)C18—C19—Br9118.9 (3)
C22—Sn2—Br794.42 (12)C19—C20—C21119.1 (4)
C15—Sn2—Br793.82 (12)C19—C20—H20120.5
Br5—Sn2—Br795.245 (17)C21—C20—H20120.5
C22—Sn2—Br686.42 (12)C20—C21—C16120.6 (4)
C15—Sn2—Br685.60 (12)C20—C21—H21119.7
Br5—Sn2—Br684.392 (16)C16—C21—H21119.7
Br7—Sn2—Br6179.163 (18)C23—C22—Sn2110.2 (3)
Sn2—Br6—Sn1122.278 (17)C23—C22—H22A109.6
C36—N1—C29109.2 (3)Sn2—C22—H22A109.6
C36—N1—C35107.0 (4)C23—C22—H22B109.6
C29—N1—C35113.2 (3)Sn2—C22—H22B109.6
C36—N1—C37110.0 (4)H22A—C22—H22B108.1
C29—N1—C37110.3 (4)C24—C23—C28118.1 (4)
C35—N1—C37107.0 (4)C24—C23—C22121.1 (4)
C2—C1—Sn1111.9 (3)C28—C23—C22120.8 (4)
C2—C1—H1A109.2C23—C24—C25121.1 (4)
Sn1—C1—H1A109.2C23—C24—H24119.5
C2—C1—H1B109.2C25—C24—H24119.5
Sn1—C1—H1B109.2C26—C25—C24119.2 (4)
H1A—C1—H1B107.9C26—C25—H25120.4
C3—C2—C7118.0 (4)C24—C25—H25120.4
C3—C2—C1119.6 (4)C25—C26—C27121.7 (4)
C7—C2—C1122.4 (4)C25—C26—Br8120.5 (3)
C4—C3—C2121.2 (4)C27—C26—Br8117.8 (3)
C4—C3—H3119.4C28—C27—C26118.2 (4)
C2—C3—H3119.4C28—C27—H27120.9
C5—C4—C3119.0 (4)C26—C27—H27120.9
C5—C4—H4120.5C27—C28—C23121.8 (4)
C3—C4—H4120.5C27—C28—H28119.1
C6—C5—C4122.0 (4)C23—C28—H28119.1
C6—C5—Br3119.0 (3)C34—C29—C30120.5 (4)
C4—C5—Br3118.9 (4)C34—C29—N1121.6 (4)
C5—C6—C7118.3 (4)C30—C29—N1117.8 (4)
C5—C6—H6120.8C31—C30—C29119.8 (4)
C7—C6—H6120.8C31—C30—H30120.1
C6—C7—C2121.3 (4)C29—C30—H30120.1
C6—C7—H7119.3C30—C31—C32120.3 (4)
C2—C7—H7119.3C30—C31—H31119.8
C9—C8—Sn1109.6 (3)C32—C31—H31119.8
C9—C8—H8A109.8C33—C32—C31119.5 (5)
Sn1—C8—H8A109.8C33—C32—H32120.2
C9—C8—H8B109.8C31—C32—H32120.2
Sn1—C8—H8B109.8C32—C33—C34121.1 (4)
H8A—C8—H8B108.2C32—C33—H33119.5
C14—C9—C10118.4 (4)C34—C33—H33119.5
C14—C9—C8121.0 (4)C33—C34—C29118.7 (4)
C10—C9—C8120.6 (4)C33—C34—H34120.6
C11—C10—C9120.5 (4)C29—C34—H34120.6
C11—C10—H10119.7N1—C35—H35A109.5
C9—C10—H10119.7N1—C35—H35B109.5
C12—C11—C10119.0 (4)H35A—C35—H35B109.5
C12—C11—H11120.5N1—C35—H35C109.5
C10—C11—H11120.5H35A—C35—H35C109.5
C11—C12—C13121.9 (4)H35B—C35—H35C109.5
C11—C12—Br4119.6 (3)N1—C36—H36A109.5
C13—C12—Br4118.5 (3)N1—C36—H36B109.5
C12—C13—C14118.5 (4)H36A—C36—H36B109.5
C12—C13—H13120.8N1—C36—H36C109.5
C14—C13—H13120.8H36A—C36—H36C109.5
C9—C14—C13121.7 (4)H36B—C36—H36C109.5
C9—C14—H14119.1N1—C37—H37A109.5
C13—C14—H14119.1N1—C37—H37B109.5
C16—C15—Sn2112.1 (3)H37A—C37—H37B109.5
C16—C15—H15A109.2N1—C37—H37C109.5
Sn2—C15—H15A109.2H37A—C37—H37C109.5
C16—C15—H15B109.2H37B—C37—H37C109.5
Sn2—C15—H15B109.2
C22—Sn2—Br6—Sn143.80 (11)Sn2—C15—C16—C1785.2 (4)
C15—Sn2—Br6—Sn1−95.34 (12)Sn2—C15—C16—C21−95.5 (4)
Br5—Sn2—Br6—Sn1153.80 (2)C21—C16—C17—C18−1.4 (7)
C1—Sn1—Br6—Sn2−100.97 (12)C15—C16—C17—C18177.9 (4)
C8—Sn1—Br6—Sn242.22 (12)C16—C17—C18—C19−0.5 (7)
Br2—Sn1—Br6—Sn2150.53 (2)C17—C18—C19—C202.2 (7)
C8—Sn1—C1—C2177.6 (3)C17—C18—C19—Br9−176.1 (4)
Br2—Sn1—C1—C2−26.4 (3)C18—C19—C20—C21−1.8 (7)
Br1—Sn1—C1—C272.0 (3)Br9—C19—C20—C21176.5 (3)
Br6—Sn1—C1—C2−109.0 (3)C19—C20—C21—C16−0.3 (6)
Sn1—C1—C2—C390.6 (4)C17—C16—C21—C201.8 (6)
Sn1—C1—C2—C7−89.3 (4)C15—C16—C21—C20−177.5 (4)
C7—C2—C3—C40.2 (7)C15—Sn2—C22—C23169.7 (3)
C1—C2—C3—C4−179.8 (4)Br5—Sn2—C22—C237.6 (3)
C2—C3—C4—C50.6 (7)Br7—Sn2—C22—C23−89.5 (3)
C3—C4—C5—C6−1.0 (7)Br6—Sn2—C22—C2390.4 (3)
C3—C4—C5—Br3−179.6 (4)Sn2—C22—C23—C24−100.2 (4)
C4—C5—C6—C70.6 (7)Sn2—C22—C23—C2877.0 (4)
Br3—C5—C6—C7179.2 (3)C28—C23—C24—C250.9 (7)
C5—C6—C7—C20.2 (7)C22—C23—C24—C25178.1 (4)
C3—C2—C7—C6−0.6 (6)C23—C24—C25—C26−2.0 (7)
C1—C2—C7—C6179.4 (4)C24—C25—C26—C272.1 (7)
C1—Sn1—C8—C9174.0 (3)C24—C25—C26—Br8180.0 (3)
Br2—Sn1—C8—C917.9 (3)C25—C26—C27—C28−1.2 (7)
Br1—Sn1—C8—C9−80.8 (3)Br8—C26—C27—C28−179.1 (3)
Br6—Sn1—C8—C9100.9 (3)C26—C27—C28—C230.1 (7)
Sn1—C8—C9—C1489.1 (4)C24—C23—C28—C270.1 (7)
Sn1—C8—C9—C10−89.0 (4)C22—C23—C28—C27−177.2 (4)
C14—C9—C10—C11−0.8 (6)C36—N1—C29—C34118.1 (5)
C8—C9—C10—C11177.4 (4)C35—N1—C29—C34−1.1 (6)
C9—C10—C11—C120.3 (7)C37—N1—C29—C34−120.9 (4)
C10—C11—C12—C130.4 (7)C36—N1—C29—C30−62.2 (5)
C10—C11—C12—Br4179.4 (3)C35—N1—C29—C30178.7 (4)
C11—C12—C13—C14−0.6 (7)C37—N1—C29—C3058.8 (5)
Br4—C12—C13—C14−179.6 (3)C34—C29—C30—C31−1.5 (7)
C10—C9—C14—C130.5 (6)N1—C29—C30—C31178.8 (4)
C8—C9—C14—C13−177.7 (4)C29—C30—C31—C320.6 (7)
C12—C13—C14—C90.2 (7)C30—C31—C32—C330.9 (7)
C22—Sn2—C15—C16171.9 (3)C31—C32—C33—C34−1.6 (7)
Br5—Sn2—C15—C16−26.2 (3)C32—C33—C34—C290.8 (7)
Br7—Sn2—C15—C1670.9 (3)C30—C29—C34—C330.8 (7)
Br6—Sn2—C15—C16−108.5 (3)N1—C29—C34—C33−179.5 (4)
Hydrogen-bond geometry (Å, °) top
Cg is the centroid of the C29-benzene ring.
D—H···AD—HH···AD···AD—H···A
C27—H27···Cgi0.952.583.378 (4)142
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Sn1—C12.163 (4)Sn2—C152.165 (4)
Sn1—C82.167 (4)Sn2—C222.160 (4)
Sn1—Br12.6203 (5)Sn2—Br62.9818 (5)
Sn1—Br22.5051 (5)Sn2—Br52.5057 (5)
Sn1—Br63.0470 (5)Sn2—Br72.6423 (5)
C1—Sn1—C8141.50 (16)C15—Sn2—C22138.41 (16)
Table 2
Hydrogen-bond geometry (Å, °) top
Cg is the centroid of the C29-benzene ring.
D—H···AD—HH···AD···AD—H···A
C27—H27···Cgi0.952.583.378 (4)142
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

references
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