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Acta Cryst. (2008). E64, m1390    [ doi:10.1107/S1600536808032236 ]

catena-Poly[[tribenzyltin(IV)]-[mu]-4-nitrocinnamato-[kappa]2O:O']

P. Y. Thong, K. M. Lo and S. W. Ng

Abstract top

The 4-nitrocinnamate anion in the title compound, [Sn(C7H7)3(C9H6NO4)]n, bridges adjacent tribenzyltin cations into a helical chain running along the b axis. The Sn atoms in the two independent molecules adopt distorted trans-C3SnO2 trigonal-bipyramidal geometries. The repeat distance of the polymeric chain is b/2.

Comment top

The polymeric structure found for tribenzyl(4-nitrocinnamato)tin(IV) conforms to expectation, Fig. 1 (Ng et al., 1989; Tiekink, 1991).

Related literature top

The triakyltin derivatives of monocarboxylic acids generally adopt carboxylate-bridged chain structures; see: Ng et al. (1989). For the trialkyltin/triaryltin derivatives of cinnamic acid and other substituted cinnamic acids, see: Ng & Kumar Das (1994); Siah et al. (1994); Willem et al. (1996). For the synthesis of tribenzyltin chloride, see: Sisido et al. (1961). For reviews of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Tribenzyltin chloride was synthesized from the direct reaction between tin powder and benzyl chloride in water (Sisido et al., 1961). The chloride was converted to tribenzyltin hydroxide by treatment with 10% sodium hydroxide in acetone. Tribenzyltin hydroxide (1.4 g, 0.3 mmol) and 4-nitrocinnamic acid (0.5 g, 0.3 mmol) were heated in ethanol (100 ml) for 1 h. Slow evaporation of the solvent yielded yellow prisms.

Refinement top

The carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The nitro group in each independent molecule are disordered in their oxygen atoms. The nitrogen–oxygen distances for the unprimed and primed atoms were restrained to within 0.01 Å of each other. The C–NO2 fragment was restrained to be nearly planar, and the temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic displacement parameters of the disordered atoms were restrained to be nearly isotropic. The occupancy could not be refined, and was arbitrarily set at 0.5. All phenyl and phenylene rings were refined as rigid hexagons of 1.39 Å sides.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2008).

Figures top
[Figure 1] Fig. 1. 70% Probability thermal ellipsoid plot (Barbour, 2001) of [(C6H5CH2)3SnO2CCH═CH—C6H4—NO2]∞. Hydrogen atoms are drawn as spheres of arbitrary radius. Only one orientation of the disordered nitro group is shown in each case.
catena-Poly[[tribenzyltin(IV)]-µ-4-nitrocinnamato-κ2O:O'] top
Crystal data top
[Sn(C7H7)3(C9H6NO4)]F(000) = 2368
Mr = 584.22Dx = 1.471 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9977 reflections
a = 21.4850 (3) Åθ = 2.4–28.3°
b = 10.2134 (1) ŵ = 1.00 mm−1
c = 25.9562 (4) ÅT = 100 K
β = 112.133 (1)°Prism, pale yellow
V = 5276.0 (1) Å30.36 × 0.03 × 0.03 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer		12115 independent reflections
Radiation source: fine-focus sealed tube9043 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −26→27
Tmin = 0.714, Tmax = 0.971k = −13→13
48779 measured reflectionsl = −32→33
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0362P)2 + 8.7819P]
where P = (Fo2 + 2Fc2)/3
12115 reflections(Δ/σ)max = 0.001
565 parametersΔρmax = 0.81 e Å−3
38 restraintsΔρmin = −0.80 e Å−3
Crystal data top
[Sn(C7H7)3(C9H6NO4)]V = 5276.0 (1) Å3
Mr = 584.22Z = 8
Monoclinic, P21/nMo Kα radiation
a = 21.4850 (3) ŵ = 1.00 mm−1
b = 10.2134 (1) ÅT = 100 K
c = 25.9562 (4) Å0.36 × 0.03 × 0.03 mm
β = 112.133 (1)°
Data collection top
Bruker SMART APEX
diffractometer		12115 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		9043 reflections with I > 2σ(I)
Tmin = 0.714, Tmax = 0.971Rint = 0.032
48779 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.091Δρmax = 0.81 e Å−3
S = 1.06Δρmin = −0.80 e Å−3
12115 reflectionsAbsolute structure: ?
565 parametersFlack parameter: ?
38 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.740576 (10)0.624465 (18)0.773616 (8)0.01626 (6)
Sn20.240598 (10)0.527516 (18)0.774258 (8)0.01660 (6)
O10.72572 (11)0.46521 (19)0.82387 (9)0.0208 (4)
O20.74811 (12)0.3133 (2)0.77179 (9)0.0285 (5)
O30.5986 (4)−0.1699 (6)1.0109 (5)0.0358 (16)0.50
O40.6223 (5)−0.0096 (19)1.0718 (4)0.063 (2)0.50
O3'0.6225 (4)−0.1780 (6)1.0239 (5)0.0358 (16)0.50
O4'0.5957 (5)−0.0086 (19)1.0602 (4)0.063 (2)0.50
O50.22693 (12)0.36739 (19)0.82563 (9)0.0239 (5)
O60.24714 (11)0.2147 (2)0.77260 (9)0.0273 (5)
O70.1482 (10)−0.2711 (10)1.0365 (13)0.039 (2)0.50
O80.0768 (8)−0.119 (3)1.0434 (7)0.047 (3)0.50
O7'0.1347 (10)−0.2814 (10)1.0294 (13)0.039 (2)0.50
O8'0.0890 (8)−0.125 (3)1.0558 (7)0.047 (3)0.50
N10.61765 (12)−0.0592 (3)1.02706 (11)0.0367 (7)
N20.11891 (13)−0.1650 (3)1.02647 (10)0.0353 (7)
C10.71495 (17)0.7671 (3)0.82323 (13)0.0229 (6)
H1A0.75350.82750.83940.027*
H1B0.67650.81930.79840.027*
C20.69693 (10)0.7136 (2)0.86959 (7)0.0190 (6)
C30.63172 (9)0.6732 (2)0.85994 (8)0.0312 (8)
H30.59770.68150.82390.037*
C40.61630 (11)0.6204 (2)0.90307 (12)0.0484 (12)
H40.57170.59280.89650.058*
C50.66609 (15)0.6082 (2)0.95584 (10)0.0544 (14)
H50.65550.57210.98530.065*
C60.73130 (13)0.6487 (3)0.96549 (7)0.0502 (12)
H60.76530.64031.00160.060*
C70.74672 (8)0.7014 (2)0.92237 (8)0.0320 (8)
H70.79130.72900.92900.038*
C80.84579 (15)0.5814 (3)0.79622 (13)0.0225 (6)
H8A0.85170.48710.79040.027*
H8B0.86370.63220.77240.027*
C90.88404 (10)0.61648 (18)0.85682 (6)0.0203 (6)
C100.88920 (10)0.52659 (14)0.89844 (8)0.0227 (6)
H100.86930.44240.88900.027*
C110.92346 (10)0.55980 (18)0.95392 (7)0.0257 (7)
H110.92700.49840.98240.031*
C120.95257 (10)0.6829 (2)0.96778 (6)0.0278 (7)
H120.97600.70561.00570.033*
C130.94741 (10)0.77282 (15)0.92616 (8)0.0266 (7)
H130.96730.85700.93560.032*
C140.91314 (10)0.73960 (16)0.87068 (7)0.0219 (6)
H140.90960.80100.84220.026*
C150.66090 (15)0.5625 (3)0.69825 (13)0.0215 (6)
H15A0.66360.61160.66630.026*
H15B0.66600.46810.69200.026*
C160.59325 (9)0.5861 (2)0.70202 (9)0.0234 (7)
C170.56721 (10)0.49508 (17)0.72834 (9)0.0270 (7)
H170.59120.41660.74280.032*
C180.50613 (11)0.5189 (2)0.73352 (10)0.0362 (9)
H180.48830.45670.75150.043*
C190.47109 (9)0.6337 (3)0.71236 (11)0.0442 (10)
H190.42930.65000.71590.053*
C200.49713 (11)0.7247 (2)0.68604 (11)0.0467 (10)
H200.47320.80320.67160.056*
C210.55821 (11)0.70092 (19)0.68086 (10)0.0352 (8)
H210.57600.76310.66290.042*
C220.73041 (15)0.3466 (3)0.81149 (12)0.0193 (6)
C230.71423 (15)0.2458 (3)0.84523 (12)0.0200 (6)
H230.71560.15610.83610.024*
C240.69782 (15)0.2774 (3)0.88809 (13)0.0222 (6)
H240.69860.36790.89670.027*
C250.67857 (11)0.18658 (16)0.92365 (8)0.0217 (6)
C260.66231 (12)0.24047 (13)0.96615 (9)0.0273 (7)
H260.66510.33240.97210.033*
C270.64194 (12)0.15980 (18)1.00000 (8)0.0300 (8)
H270.63080.19661.02900.036*
C280.63784 (12)0.02523 (17)0.99136 (8)0.0260 (7)
C290.65410 (13)−0.02866 (13)0.94886 (9)0.0290 (8)
H290.6513−0.12060.94300.035*
C300.67447 (12)0.05201 (17)0.91501 (8)0.0279 (7)
H300.68560.01520.88600.034*
C310.34371 (15)0.4752 (3)0.78971 (13)0.0234 (7)
H31A0.34890.37890.79160.028*
H31B0.35670.50820.75930.028*
C320.38785 (10)0.5362 (2)0.84441 (7)0.0257 (7)
C330.39227 (11)0.4797 (2)0.89438 (9)0.0348 (8)
H330.37040.39880.89430.042*
C340.42867 (12)0.5415 (3)0.94443 (7)0.0456 (11)
H340.43170.50290.97860.055*
C350.46065 (12)0.6599 (3)0.94449 (8)0.0482 (11)
H350.48550.70210.97870.058*
C360.45623 (11)0.71638 (19)0.89452 (11)0.0425 (10)
H360.47810.79730.89460.051*
C370.41983 (11)0.6546 (2)0.84447 (8)0.0327 (8)
H370.41680.69320.81030.039*
C380.23174 (16)0.6679 (3)0.83283 (13)0.0207 (6)
H38A0.27510.67120.86500.025*
H38B0.22420.75520.81500.025*
C390.17661 (9)0.6429 (2)0.85455 (8)0.0206 (6)
C400.18741 (8)0.5606 (2)0.89975 (8)0.0258 (7)
H400.22990.51980.91760.031*
C410.13605 (11)0.5380 (2)0.91892 (8)0.0325 (8)
H410.14340.48170.94980.039*
C420.07389 (9)0.5977 (2)0.89288 (9)0.0349 (8)
H420.03880.58220.90600.042*
C430.06308 (8)0.6800 (2)0.84768 (9)0.0376 (9)
H430.02060.72080.82990.045*
C440.11444 (10)0.7026 (2)0.82851 (8)0.0293 (7)
H440.10710.75890.79760.035*
C450.15670 (16)0.4719 (3)0.70112 (14)0.0245 (7)
H45A0.16530.49980.66790.029*
H45B0.15270.37530.70000.029*
C460.09086 (9)0.5305 (2)0.69842 (10)0.0258 (7)
C470.05407 (12)0.4697 (2)0.72566 (10)0.0370 (9)
H470.06970.39010.74520.044*
C48−0.00562 (12)0.5252 (3)0.72425 (12)0.0517 (12)
H48−0.03080.48360.74290.062*
C49−0.02853 (10)0.6416 (3)0.69561 (12)0.0561 (13)
H49−0.06930.67950.69460.067*
C500.00826 (13)0.7024 (2)0.66837 (11)0.0506 (12)
H50−0.00740.78200.64880.061*
C510.06795 (12)0.6469 (2)0.66978 (10)0.0353 (8)
H510.09310.68850.65120.042*
C520.23218 (15)0.2495 (3)0.81304 (13)0.0198 (6)
C530.21856 (16)0.1483 (3)0.84854 (13)0.0211 (6)
H530.22980.05970.84500.025*
C540.19105 (17)0.1782 (3)0.88532 (13)0.0254 (7)
H540.18280.26830.88930.030*
C550.17221 (12)0.08569 (17)0.92023 (9)0.0255 (7)
C560.13401 (15)0.13270 (16)0.94915 (12)0.0541 (13)
H560.12020.22170.94540.065*
C570.11599 (14)0.0494 (2)0.98357 (11)0.0567 (14)
H570.08990.08161.00330.068*
C580.13617 (13)−0.08082 (19)0.98908 (9)0.0283 (7)
C590.17438 (12)−0.12784 (15)0.96017 (9)0.0288 (7)
H590.1882−0.21690.96390.035*
C600.19240 (11)−0.04458 (19)0.92574 (9)0.0265 (7)
H600.2185−0.07670.90600.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02067 (11)0.01290 (10)0.01803 (10)−0.00047 (8)0.01050 (8)−0.00080 (8)
Sn20.01892 (10)0.01368 (10)0.02153 (11)0.00060 (8)0.01256 (8)−0.00001 (8)
O10.0309 (12)0.0125 (10)0.0231 (11)−0.0006 (9)0.0149 (10)−0.0016 (8)
O20.0385 (14)0.0240 (12)0.0296 (12)0.0031 (10)0.0203 (11)−0.0003 (10)
O30.046 (5)0.0261 (15)0.041 (4)−0.009 (2)0.023 (4)0.0018 (18)
O40.120 (7)0.0448 (19)0.049 (4)−0.019 (6)0.060 (4)−0.008 (3)
O3'0.046 (5)0.0261 (15)0.041 (4)−0.009 (2)0.023 (4)0.0018 (18)
O4'0.120 (7)0.0448 (19)0.049 (4)−0.019 (6)0.060 (4)−0.008 (3)
O50.0386 (13)0.0129 (10)0.0305 (12)0.0013 (9)0.0247 (11)0.0013 (9)
O60.0357 (13)0.0235 (12)0.0315 (12)0.0019 (10)0.0228 (11)−0.0018 (10)
O70.035 (7)0.039 (2)0.037 (6)−0.014 (3)0.008 (5)0.013 (2)
O80.084 (5)0.043 (3)0.029 (6)−0.018 (4)0.040 (5)−0.004 (6)
O7'0.035 (7)0.039 (2)0.037 (6)−0.014 (3)0.008 (5)0.013 (2)
O8'0.084 (5)0.043 (3)0.029 (6)−0.018 (4)0.040 (5)−0.004 (6)
N10.063 (2)0.0263 (16)0.0308 (16)−0.0070 (15)0.0295 (16)−0.0007 (13)
N20.0500 (19)0.0320 (17)0.0264 (15)−0.0184 (15)0.0172 (14)−0.0017 (13)
C10.0378 (18)0.0084 (13)0.0267 (16)−0.0008 (12)0.0169 (14)−0.0032 (12)
C20.0235 (15)0.0129 (13)0.0246 (15)0.0027 (11)0.0135 (13)−0.0024 (12)
C30.0278 (17)0.0282 (17)0.043 (2)−0.0029 (14)0.0192 (16)−0.0153 (16)
C40.057 (3)0.0265 (19)0.091 (4)−0.0157 (18)0.062 (3)−0.022 (2)
C50.108 (4)0.0225 (19)0.066 (3)0.013 (2)0.070 (3)0.0097 (19)
C60.075 (3)0.051 (3)0.033 (2)0.032 (2)0.030 (2)0.0167 (19)
C70.0285 (18)0.042 (2)0.0258 (17)0.0099 (15)0.0105 (14)−0.0001 (15)
C80.0256 (16)0.0215 (15)0.0253 (16)0.0038 (13)0.0152 (13)0.0028 (13)
C90.0186 (15)0.0209 (15)0.0253 (16)0.0035 (12)0.0127 (13)0.0033 (12)
C100.0217 (15)0.0198 (15)0.0293 (17)0.0035 (12)0.0127 (13)0.0056 (13)
C110.0248 (16)0.0286 (17)0.0275 (17)0.0080 (14)0.0140 (14)0.0099 (14)
C120.0263 (17)0.0344 (18)0.0230 (16)0.0053 (14)0.0098 (14)−0.0028 (14)
C130.0250 (16)0.0219 (16)0.0337 (18)0.0021 (13)0.0119 (14)−0.0034 (14)
C140.0222 (15)0.0189 (15)0.0291 (16)0.0037 (12)0.0146 (13)0.0057 (12)
C150.0237 (16)0.0210 (15)0.0223 (15)−0.0019 (12)0.0115 (13)−0.0034 (12)
C160.0212 (16)0.0246 (16)0.0233 (16)−0.0016 (13)0.0071 (13)−0.0064 (13)
C170.0287 (17)0.0275 (17)0.0257 (17)−0.0075 (14)0.0112 (14)−0.0077 (14)
C180.0291 (19)0.049 (2)0.0323 (19)−0.0132 (17)0.0134 (16)−0.0112 (17)
C190.0226 (18)0.069 (3)0.043 (2)−0.0029 (18)0.0144 (17)−0.010 (2)
C200.031 (2)0.054 (3)0.054 (3)0.0162 (19)0.0138 (19)0.002 (2)
C210.0315 (19)0.034 (2)0.040 (2)0.0057 (15)0.0131 (16)0.0026 (16)
C220.0207 (15)0.0162 (14)0.0223 (15)0.0007 (12)0.0094 (12)−0.0022 (12)
C230.0235 (15)0.0118 (14)0.0251 (15)−0.0007 (11)0.0097 (13)0.0009 (11)
C240.0281 (16)0.0139 (14)0.0275 (16)−0.0021 (12)0.0137 (13)−0.0006 (12)
C250.0275 (16)0.0177 (14)0.0230 (15)−0.0006 (12)0.0130 (13)0.0005 (12)
C260.041 (2)0.0175 (15)0.0290 (17)0.0022 (14)0.0197 (15)−0.0006 (13)
C270.046 (2)0.0271 (17)0.0273 (17)0.0006 (15)0.0255 (16)−0.0036 (14)
C280.0375 (19)0.0219 (16)0.0228 (16)−0.0024 (14)0.0162 (15)0.0008 (13)
C290.048 (2)0.0177 (16)0.0295 (18)−0.0028 (14)0.0237 (17)−0.0017 (13)
C300.044 (2)0.0207 (15)0.0280 (17)−0.0046 (14)0.0242 (16)−0.0037 (13)
C310.0234 (16)0.0205 (15)0.0306 (17)0.0049 (12)0.0152 (14)0.0003 (13)
C320.0178 (15)0.0264 (17)0.0331 (18)0.0069 (13)0.0098 (14)0.0017 (14)
C330.0247 (18)0.048 (2)0.0314 (19)0.0064 (16)0.0106 (15)0.0059 (17)
C340.028 (2)0.076 (3)0.031 (2)0.010 (2)0.0098 (16)0.003 (2)
C350.0255 (19)0.068 (3)0.043 (2)0.008 (2)0.0039 (17)−0.020 (2)
C360.0274 (19)0.035 (2)0.058 (3)0.0038 (16)0.0083 (18)−0.0115 (19)
C370.0241 (17)0.0282 (18)0.044 (2)0.0077 (14)0.0114 (16)0.0036 (16)
C380.0283 (16)0.0136 (14)0.0254 (16)0.0005 (12)0.0160 (13)−0.0013 (12)
C390.0265 (16)0.0176 (15)0.0214 (15)0.0026 (12)0.0133 (13)−0.0015 (12)
C400.0308 (17)0.0246 (16)0.0266 (17)0.0092 (14)0.0161 (14)0.0039 (13)
C410.050 (2)0.0233 (17)0.0348 (19)0.0058 (15)0.0287 (18)0.0055 (14)
C420.034 (2)0.042 (2)0.041 (2)−0.0001 (16)0.0278 (17)−0.0043 (17)
C430.0273 (18)0.056 (2)0.0338 (19)0.0129 (17)0.0167 (16)0.0014 (18)
C440.0311 (18)0.0361 (19)0.0250 (17)0.0106 (15)0.0155 (14)0.0043 (14)
C450.0260 (16)0.0216 (16)0.0281 (17)−0.0034 (13)0.0127 (14)−0.0052 (13)
C460.0207 (16)0.0269 (17)0.0284 (17)−0.0036 (13)0.0076 (14)−0.0088 (13)
C470.033 (2)0.034 (2)0.051 (2)−0.0086 (16)0.0228 (18)−0.0098 (17)
C480.029 (2)0.066 (3)0.066 (3)−0.012 (2)0.024 (2)−0.022 (2)
C490.024 (2)0.079 (3)0.056 (3)0.012 (2)0.0045 (19)−0.026 (3)
C500.043 (2)0.047 (3)0.043 (2)0.019 (2)−0.0054 (19)−0.011 (2)
C510.033 (2)0.033 (2)0.0335 (19)0.0032 (16)0.0055 (16)−0.0051 (16)
C520.0217 (15)0.0124 (14)0.0301 (16)−0.0002 (11)0.0151 (13)0.0011 (12)
C530.0278 (16)0.0114 (13)0.0265 (16)−0.0008 (12)0.0130 (13)0.0007 (12)
C540.0351 (18)0.0152 (14)0.0302 (17)−0.0009 (13)0.0173 (15)−0.0025 (13)
C550.0369 (19)0.0210 (15)0.0247 (16)−0.0049 (14)0.0185 (15)−0.0006 (13)
C560.106 (4)0.0200 (18)0.075 (3)0.008 (2)0.078 (3)0.0062 (19)
C570.110 (4)0.027 (2)0.073 (3)0.003 (2)0.080 (3)0.002 (2)
C580.041 (2)0.0245 (17)0.0223 (16)−0.0130 (15)0.0158 (15)−0.0032 (13)
C590.0326 (18)0.0236 (16)0.0310 (18)−0.0021 (14)0.0129 (15)0.0034 (14)
C600.0326 (18)0.0217 (16)0.0297 (17)−0.0009 (13)0.0169 (15)0.0009 (13)
Geometric parameters (Å, °) top
Sn1—C12.149 (3)C23—H230.9500
Sn1—C152.153 (3)C24—C251.473 (3)
Sn1—C82.156 (3)C24—H240.9500
Sn1—O12.182 (2)C25—C261.3900
Sn1—O2i2.320 (2)C25—C301.3900
Sn2—C452.144 (3)C26—C271.3900
Sn2—C382.149 (3)C26—H260.9500
Sn2—C312.164 (3)C27—C281.3900
Sn2—O52.199 (2)C27—H270.9500
Sn2—O6ii2.334 (2)C28—C291.3900
O1—C221.267 (3)C29—C301.3900
O2—C221.272 (3)C29—H290.9500
O2—Sn1iii2.320 (2)C30—H300.9500
O3—N11.222 (6)C31—C321.513 (4)
O4—N11.235 (7)C31—H31A0.9900
O3'—N11.223 (6)C31—H31B0.9900
O4'—N11.238 (7)C32—C331.3900
O5—C521.264 (3)C32—C371.3900
O6—C521.259 (3)C33—C341.3900
O6—Sn2iv2.334 (2)C33—H330.9500
O7—N21.231 (7)C34—C351.3900
O8—N21.240 (7)C34—H340.9500
O7'—N21.230 (7)C35—C361.3900
O8'—N21.235 (7)C35—H350.9500
N1—C281.447 (3)C36—C371.3900
N2—C581.446 (3)C36—H360.9500
C1—C21.499 (3)C37—H370.9500
C1—H1A0.9900C38—C391.513 (3)
C1—H1B0.9900C38—H38A0.9900
C2—C31.3900C38—H38B0.9900
C2—C71.3900C39—C401.3900
C3—C41.3900C39—C441.3900
C3—H30.9500C40—C411.3900
C4—C51.3900C40—H400.9500
C4—H40.9500C41—C421.3900
C5—C61.3900C41—H410.9500
C5—H50.9500C42—C431.3900
C6—C71.3900C42—H420.9500
C6—H60.9500C43—C441.3900
C7—H70.9500C43—H430.9500
C8—C91.518 (3)C44—H440.9500
C8—H8A0.9900C45—C461.513 (3)
C8—H8B0.9900C45—H45A0.9900
C9—C101.3900C45—H45B0.9900
C9—C141.3900C46—C471.3900
C10—C111.3900C46—C511.3900
C10—H100.9500C47—C481.3900
C11—C121.3900C47—H470.9500
C11—H110.9500C48—C491.3900
C12—C131.3900C48—H480.9500
C12—H120.9500C49—C501.3900
C13—C141.3900C49—H490.9500
C13—H130.9500C50—C511.3900
C14—H140.9500C50—H500.9500
C15—C161.512 (3)C51—H510.9500
C15—H15A0.9900C52—C531.485 (4)
C15—H15B0.9900C53—C541.334 (4)
C16—C171.3900C53—H530.9500
C16—C211.3900C54—C551.468 (3)
C17—C181.3900C54—H540.9500
C17—H170.9500C55—C561.3900
C18—C191.3900C55—C601.3900
C18—H180.9500C56—C571.3900
C19—C201.3900C56—H560.9500
C19—H190.9500C57—C581.3900
C20—C211.3900C57—H570.9500
C20—H200.9500C58—C591.3900
C21—H210.9500C59—C601.3900
C22—C231.476 (4)C59—H590.9500
C23—C241.327 (4)C60—H600.9500
C1—Sn1—C15116.64 (12)C26—C25—C30120.0
C1—Sn1—C8117.02 (13)C26—C25—C24117.50 (17)
C15—Sn1—C8125.49 (12)C30—C25—C24122.48 (17)
C1—Sn1—O191.07 (9)C25—C26—C27120.0
C15—Sn1—O194.51 (10)C25—C26—H26120.0
C8—Sn1—O193.42 (10)C27—C26—H26120.0
C1—Sn1—O2i80.82 (10)C26—C27—C28120.0
C15—Sn1—O2i89.00 (10)C26—C27—H27120.0
C8—Sn1—O2i90.47 (10)C28—C27—H27120.0
O1—Sn1—O2i171.89 (8)C29—C28—C27120.0
C45—Sn2—C38122.28 (12)C29—C28—N1119.86 (17)
C45—Sn2—C31123.99 (12)C27—C28—N1120.13 (17)
C38—Sn2—C31112.99 (12)C28—C29—C30120.0
C45—Sn2—O594.59 (11)C28—C29—H29120.0
C38—Sn2—O589.97 (9)C30—C29—H29120.0
C31—Sn2—O593.75 (10)C29—C30—C25120.0
C45—Sn2—O6ii88.74 (10)C29—C30—H30120.0
C38—Sn2—O6ii83.09 (10)C25—C30—H30120.0
C31—Sn2—O6ii89.43 (10)C32—C31—Sn2107.96 (18)
O5—Sn2—O6ii173.04 (8)C32—C31—H31A110.1
C22—O1—Sn1121.17 (19)Sn2—C31—H31A110.1
C22—O2—Sn1iii139.0 (2)C32—C31—H31B110.1
C52—O5—Sn2120.44 (19)Sn2—C31—H31B110.1
C52—O6—Sn2iv141.3 (2)H31A—C31—H31B108.4
O3—N1—O4126.9 (12)C33—C32—C37120.0
O3'—N1—O4'121.7 (12)C33—C32—C31120.21 (19)
O3—N1—C28118.3 (7)C37—C32—C31119.60 (18)
O3'—N1—C28119.6 (7)C32—C33—C34120.0
O4—N1—C28114.8 (10)C32—C33—H33120.0
O4'—N1—C28118.7 (11)C34—C33—H33120.0
O7'—N2—O8'118 (3)C33—C34—C35120.0
O7—N2—O8130 (2)C33—C34—H34120.0
O7'—N2—C58118.8 (18)C35—C34—H34120.0
O7—N2—C58115.1 (18)C36—C35—C34120.0
O8'—N2—C58122.7 (16)C36—C35—H35120.0
O8—N2—C58114.7 (15)C34—C35—H35120.0
C2—C1—Sn1115.87 (18)C35—C36—C37120.0
C2—C1—H1A108.3C35—C36—H36120.0
Sn1—C1—H1A108.3C37—C36—H36120.0
C2—C1—H1B108.3C36—C37—C32120.0
Sn1—C1—H1B108.3C36—C37—H37120.0
H1A—C1—H1B107.4C32—C37—H37120.0
C3—C2—C7120.0C39—C38—Sn2116.21 (18)
C3—C2—C1120.75 (19)C39—C38—H38A108.2
C7—C2—C1119.23 (19)Sn2—C38—H38A108.2
C2—C3—C4120.0C39—C38—H38B108.2
C2—C3—H3120.0Sn2—C38—H38B108.2
C4—C3—H3120.0H38A—C38—H38B107.4
C5—C4—C3120.0C40—C39—C44120.0
C5—C4—H4120.0C40—C39—C38120.74 (17)
C3—C4—H4120.0C44—C39—C38119.26 (17)
C4—C5—C6120.0C39—C40—C41120.0
C4—C5—H5120.0C39—C40—H40120.0
C6—C5—H5120.0C41—C40—H40120.0
C5—C6—C7120.0C42—C41—C40120.0
C5—C6—H6120.0C42—C41—H41120.0
C7—C6—H6120.0C40—C41—H41120.0
C6—C7—C2120.0C41—C42—C43120.0
C6—C7—H7120.0C41—C42—H42120.0
C2—C7—H7120.0C43—C42—H42120.0
C9—C8—Sn1109.68 (17)C44—C43—C42120.0
C9—C8—H8A109.7C44—C43—H43120.0
Sn1—C8—H8A109.7C42—C43—H43120.0
C9—C8—H8B109.7C43—C44—C39120.0
Sn1—C8—H8B109.7C43—C44—H44120.0
H8A—C8—H8B108.2C39—C44—H44120.0
C10—C9—C14120.0C46—C45—Sn2113.29 (19)
C10—C9—C8120.19 (17)C46—C45—H45A108.9
C14—C9—C8119.81 (17)Sn2—C45—H45A108.9
C9—C10—C11120.0C46—C45—H45B108.9
C9—C10—H10120.0Sn2—C45—H45B108.9
C11—C10—H10120.0H45A—C45—H45B107.7
C12—C11—C10120.0C47—C46—C51120.0
C12—C11—H11120.0C47—C46—C45120.02 (19)
C10—C11—H11120.0C51—C46—C45119.97 (19)
C11—C12—C13120.0C46—C47—C48120.0
C11—C12—H12120.0C46—C47—H47120.0
C13—C12—H12120.0C48—C47—H47120.0
C14—C13—C12120.0C47—C48—C49120.0
C14—C13—H13120.0C47—C48—H48120.0
C12—C13—H13120.0C49—C48—H48120.0
C13—C14—C9120.0C50—C49—C48120.0
C13—C14—H14120.0C50—C49—H49120.0
C9—C14—H14120.0C48—C49—H49120.0
C16—C15—Sn1110.42 (18)C49—C50—C51120.0
C16—C15—H15A109.6C49—C50—H50120.0
Sn1—C15—H15A109.6C51—C50—H50120.0
C16—C15—H15B109.6C50—C51—C46120.0
Sn1—C15—H15B109.6C50—C51—H51120.0
H15A—C15—H15B108.1C46—C51—H51120.0
C17—C16—C21120.0O6—C52—O5124.0 (3)
C17—C16—C15119.98 (18)O6—C52—C53119.5 (3)
C21—C16—C15119.98 (18)O5—C52—C53116.4 (3)
C18—C17—C16120.0C54—C53—C52121.9 (3)
C18—C17—H17120.0C54—C53—H53119.0
C16—C17—H17120.0C52—C53—H53119.0
C17—C18—C19120.0C53—C54—C55126.4 (3)
C17—C18—H18120.0C53—C54—H54116.8
C19—C18—H18120.0C55—C54—H54116.8
C20—C19—C18120.0C56—C55—C60120.0
C20—C19—H19120.0C56—C55—C54117.85 (18)
C18—C19—H19120.0C60—C55—C54122.14 (18)
C19—C20—C21120.0C57—C56—C55120.0
C19—C20—H20120.0C57—C56—H56120.0
C21—C20—H20120.0C55—C56—H56120.0
C20—C21—C16120.0C56—C57—C58120.0
C20—C21—H21120.0C56—C57—H57120.0
C16—C21—H21120.0C58—C57—H57120.0
O1—C22—O2122.5 (3)C57—C58—C59120.0
O1—C22—C23117.2 (3)C57—C58—N2119.3 (2)
O2—C22—C23120.2 (3)C59—C58—N2120.7 (2)
C24—C23—C22121.6 (3)C60—C59—C58120.0
C24—C23—H23119.2C60—C59—H59120.0
C22—C23—H23119.2C58—C59—H59120.0
C23—C24—C25126.7 (3)C59—C60—C55120.0
C23—C24—H24116.6C59—C60—H60120.0
C25—C24—H24116.6C55—C60—H60120.0
C1—Sn1—O1—C22175.8 (2)C28—C29—C30—C250.0
C15—Sn1—O1—C2258.9 (2)C26—C25—C30—C290.0
C8—Sn1—O1—C22−67.1 (2)C24—C25—C30—C29−178.1 (2)
C45—Sn2—O5—C5262.7 (3)C45—Sn2—C31—C32178.15 (17)
C38—Sn2—O5—C52−174.9 (3)C38—Sn2—C31—C327.8 (2)
C31—Sn2—O5—C52−61.9 (3)O5—Sn2—C31—C32−83.74 (19)
C15—Sn1—C1—C294.9 (2)O6ii—Sn2—C31—C3290.06 (18)
C8—Sn1—C1—C2−95.0 (2)Sn2—C31—C32—C3377.7 (2)
O1—Sn1—C1—C2−0.6 (2)Sn2—C31—C32—C37−97.25 (18)
O2i—Sn1—C1—C2179.2 (2)C37—C32—C33—C340.0
Sn1—C1—C2—C3−85.2 (2)C31—C32—C33—C34−175.0 (2)
Sn1—C1—C2—C793.0 (2)C32—C33—C34—C350.0
C7—C2—C3—C40.0C33—C34—C35—C360.0
C1—C2—C3—C4178.2 (2)C34—C35—C36—C370.0
C2—C3—C4—C50.0C35—C36—C37—C320.0
C3—C4—C5—C60.0C33—C32—C37—C360.0
C4—C5—C6—C70.0C31—C32—C37—C36175.0 (2)
C5—C6—C7—C20.0C45—Sn2—C38—C3952.1 (2)
C3—C2—C7—C60.0C31—Sn2—C38—C39−137.34 (19)
C1—C2—C7—C6−178.2 (2)O5—Sn2—C38—C39−43.3 (2)
C1—Sn1—C8—C922.8 (2)O6ii—Sn2—C38—C39136.2 (2)
C15—Sn1—C8—C9−168.14 (16)Sn2—C38—C39—C4085.3 (2)
O1—Sn1—C8—C9−70.14 (18)Sn2—C38—C39—C44−94.2 (2)
O2i—Sn1—C8—C9102.75 (18)C44—C39—C40—C410.0
Sn1—C8—C9—C1086.16 (19)C38—C39—C40—C41−179.5 (2)
Sn1—C8—C9—C14−92.93 (18)C39—C40—C41—C420.0
C14—C9—C10—C110.0C40—C41—C42—C430.0
C8—C9—C10—C11−179.1 (2)C41—C42—C43—C440.0
C9—C10—C11—C120.0C42—C43—C44—C390.0
C10—C11—C12—C130.0C40—C39—C44—C430.0
C11—C12—C13—C140.0C38—C39—C44—C43179.5 (2)
C12—C13—C14—C90.0C38—Sn2—C45—C46−5.7 (3)
C10—C9—C14—C130.0C31—Sn2—C45—C46−175.18 (18)
C8—C9—C14—C13179.1 (2)O5—Sn2—C45—C4687.2 (2)
C1—Sn1—C15—C16−22.7 (2)O6ii—Sn2—C45—C46−86.7 (2)
C8—Sn1—C15—C16168.22 (17)Sn2—C45—C46—C47−84.2 (2)
O1—Sn1—C15—C1670.77 (19)Sn2—C45—C46—C5194.3 (2)
O2i—Sn1—C15—C16−101.91 (19)C51—C46—C47—C480.0
Sn1—C15—C16—C17−83.3 (2)C45—C46—C47—C48178.5 (2)
Sn1—C15—C16—C2194.47 (19)C46—C47—C48—C490.0
C21—C16—C17—C180.0C47—C48—C49—C500.0
C15—C16—C17—C18177.8 (2)C48—C49—C50—C510.0
C16—C17—C18—C190.0C49—C50—C51—C460.0
C17—C18—C19—C200.0C47—C46—C51—C500.0
C18—C19—C20—C210.0C45—C46—C51—C50−178.5 (2)
C19—C20—C21—C160.0Sn2iv—O6—C52—O5−176.0 (2)
C17—C16—C21—C200.0Sn2iv—O6—C52—C533.1 (5)
C15—C16—C21—C20−177.8 (2)Sn2—O5—C52—O62.2 (4)
Sn1—O1—C22—O24.7 (4)Sn2—O5—C52—C53−176.9 (2)
Sn1—O1—C22—C23−175.23 (19)O6—C52—C53—C54−167.7 (3)
Sn1iii—O2—C22—O1−175.1 (2)O5—C52—C53—C5411.4 (5)
Sn1iii—O2—C22—C234.8 (5)C52—C53—C54—C55176.5 (3)
O1—C22—C23—C24−2.4 (4)C53—C54—C55—C56−169.4 (3)
O2—C22—C23—C24177.7 (3)C53—C54—C55—C6011.8 (5)
C22—C23—C24—C25177.8 (3)C60—C55—C56—C570.0
C23—C24—C25—C26−179.2 (3)C54—C55—C56—C57−178.8 (2)
C23—C24—C25—C30−1.0 (4)C55—C56—C57—C580.0
C30—C25—C26—C270.0C56—C57—C58—C590.0
C24—C25—C26—C27178.2 (2)C56—C57—C58—N2178.0 (2)
C25—C26—C27—C280.0O7'—N2—C58—C57177.1 (10)
C26—C27—C28—C290.0O7—N2—C58—C57−167.7 (10)
C26—C27—C28—N1179.1 (2)O8'—N2—C58—C57−3.0 (10)
O3—N1—C28—C29−18.7 (4)O8—N2—C58—C5712.3 (10)
O3'—N1—C28—C298.5 (4)O7'—N2—C58—C59−4.9 (10)
O4—N1—C28—C29160.8 (5)O7—N2—C58—C5910.2 (10)
O4'—N1—C28—C29−171.4 (4)O8'—N2—C58—C59175.0 (10)
O3—N1—C28—C27162.2 (4)O8—N2—C58—C59−169.8 (10)
O3'—N1—C28—C27−170.6 (4)C57—C58—C59—C600.0
O4—N1—C28—C27−18.3 (5)N2—C58—C59—C60−177.9 (2)
O4'—N1—C28—C279.5 (4)C58—C59—C60—C550.0
C27—C28—C29—C300.0C56—C55—C60—C590.0
N1—C28—C29—C30−179.1 (2)C54—C55—C60—C59178.7 (3)
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1/2, y−1/2, −z+3/2.
Acknowledgements top

The authors thank the University of Malaya for funding this study (grant No. FS339/2008A).

references
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