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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1103.
Published online 2008 July 31. doi:  10.1107/S1600536808023787
PMCID: PMC2962005

Octa-n-butyl-1κ 2 C,2κ 2 C,3κ 2 C,4κ 2 C-tetra­kis(μ-2-hydroxy­benzoato)-1:2κ 2 O:O;2:3κ2 O:O′;3:4κ 2 O:O;1:4κ 2 O:O′-di-μ 3-oxido-1:2:3κ 3 O:O:O;1:3:4κ 3 O:O:O-tetra­tin(IV)

Abstract

In the centrosymmetric tetra­nuclear title compound, [Sn4(C4H9)8(C7H5O3)4O2], one of the two independent Sn atoms is five-coordinate in a cis-C2SnO3 trigonal-bipyramidal geometry [C—Sn—C = 142.7 (1)°]; the geometry is distorted owing to a long Sn(...)O(double bond) inter­action [Sn(...)O = 2.862 (1) Å]. The other Sn atom has a bent R 2Sn skeleton [C—Sn—C = 144.0 (1)°], but the geometry is best regarded as being a trans-C2SnO4 octa­hedron as the Sn–O(single bond) inter­action is shorter [Sn—O = 2.674 (1) Å].

Related literature

For a review of the structural chemistry of organotin carboxyl­ates, see: Tiekink (1991 [triangle], 1994 [triangle]). For a description of carboxyl­ato-distannoxanes, see: Ng et al. (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1103-scheme1.jpg

Experimental

Crystal data

  • [Sn4(C4H9)8(C7H5O3)4O2]
  • M r = 1512.10
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1103-efi1.jpg
  • a = 11.4549 (2) Å
  • b = 12.1610 (2) Å
  • c = 13.4436 (2) Å
  • α = 106.300 (1)°
  • β = 92.532 (1)°
  • γ = 115.204 (1)°
  • V = 1597.18 (5) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.60 mm−1
  • T = 100 (2) K
  • 0.38 × 0.30 × 0.18 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.581, T max = 0.761
  • 9253 measured reflections
  • 7210 independent reflections
  • 6583 reflections with I > 2σ(I)
  • R int = 0.008

Refinement

  • R[F 2 > 2σ(F 2)] = 0.018
  • wR(F 2) = 0.067
  • S = 1.17
  • 7210 reflections
  • 352 parameters
  • H-atom parameters constrained
  • Δρmax = 0.91 e Å−3
  • Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023787/tk2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023787/tk2287Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for funding this study (SF022/2007 A, FS339/2008 A) and also for the purchase of the diffractometer.

supplementary crystallographic information

Comment

Diorganotin dicarboxylates are conveniently synthesized by condensing a diorganotin oxide with a carboxylic acid; occasionally, only one molar portion of the acid is used up to afford a tetranuclear distannoxane. The strucutural chemistry of distannoxanes has been reviewed (Ng et al., 1991; Tiekink, 1991; 1994). The title compound (Scheme I, Fig. 1) is formed in a 1:2 condensation between di-n-butyltin oxide and 2-hydroxybenzoic acid. The hydroxyl-H atoms form intramolecular hydrogen bonds to the more weakly bound O atoms (Table 1).

Experimental

Dibutyltin oxide (2 g, 8 mmol) and salicylic acid (2.2 g, 16 mmol) were acid heated in ethanol (100 ml) until the reactants dissolved completely. Slow evaporation of the filtered solution yielded colorless crystals.

Refinement

Carbon-bound H-atoms were placed in 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 1.2–1.5Ueq(C). The hydroxy H-atoms were similarly constrained (O–H 0.84 Å) but the hybridization of the oxygen atoms was assumed to be sp2.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) plot of [Sn2(C4H9)4(C7H5O3)2O]2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The unlabelled atoms are related by a center of inversion.

Crystal data

[Sn4(C4H9)8(C7H5O3)4O2]Z = 1
Mr = 1512.10F000 = 764
Triclinic, P1Dx = 1.572 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 11.4549 (2) ÅCell parameters from 8563 reflections
b = 12.1610 (2) Åθ = 2.1–30.4º
c = 13.4436 (2) ŵ = 1.61 mm1
α = 106.300 (1)ºT = 100 (2) K
β = 92.532 (1)ºBlock, colorless
γ = 115.204 (1)º0.38 × 0.30 × 0.18 mm
V = 1597.18 (5) Å3

Data collection

Bruker SMART APEX diffractometer7210 independent reflections
Radiation source: fine-focus sealed tube6583 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.008
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −7→14
Tmin = 0.581, Tmax = 0.761k = −15→15
9253 measured reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.067  w = 1/[σ2(Fo2) + (0.0396P)2 + 0.6175P] where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
7210 reflectionsΔρmax = 0.91 e Å3
352 parametersΔρmin = −0.86 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
Sn10.474718 (13)0.580180 (13)0.753402 (10)0.01404 (5)
Sn20.456706 (13)0.604166 (12)0.476911 (10)0.01191 (5)
O10.41023 (18)0.72441 (17)0.74041 (13)0.0253 (4)
O20.40862 (16)0.75903 (15)0.58632 (12)0.0191 (3)
O30.37161 (16)0.95576 (15)0.57647 (12)0.0214 (3)
H30.39930.90350.54660.032*
O40.54344 (15)0.43088 (14)0.72857 (11)0.0163 (3)
O50.51748 (16)0.45675 (15)0.89385 (12)0.0201 (3)
O60.55126 (18)0.31818 (17)0.99204 (13)0.0265 (4)
H60.52720.37490.99370.040*
O70.48810 (14)0.54280 (13)0.59784 (11)0.0140 (3)
C10.2821 (2)0.4578 (2)0.76932 (18)0.0209 (4)
H1A0.23820.38720.70110.025*
H1B0.29120.41810.82230.025*
C20.1914 (2)0.5184 (2)0.80106 (18)0.0214 (4)
H2A0.16750.54390.74260.026*
H2B0.23870.59720.86330.026*
C30.0665 (2)0.4265 (2)0.8274 (2)0.0274 (5)
H3A0.01950.34750.76520.033*
H3B0.09050.40130.88600.033*
C4−0.0249 (3)0.4862 (3)0.8588 (2)0.0366 (6)
H4A−0.10340.42400.87520.055*
H4B−0.05080.50940.80030.055*
H4C0.02060.56370.92100.055*
C50.6564 (2)0.7396 (2)0.84066 (17)0.0197 (4)
H5A0.70110.78310.79120.024*
H5B0.63610.80130.89310.024*
C60.7543 (2)0.7138 (2)0.89931 (18)0.0228 (4)
H6A0.71750.68460.95770.027*
H6B0.76690.64370.85040.027*
C70.8873 (2)0.8329 (2)0.94411 (18)0.0239 (5)
H7A0.92830.85630.88500.029*
H7B0.87340.90570.98650.029*
C80.9803 (3)0.8134 (3)1.0124 (2)0.0369 (6)
H8A1.06370.89251.03860.055*
H8B0.99600.74250.97060.055*
H8C0.94140.79251.07220.055*
C90.2521 (2)0.4950 (2)0.41335 (16)0.0172 (4)
H9A0.21970.55100.39340.021*
H9B0.23800.42390.34850.021*
C100.1726 (2)0.4388 (2)0.49052 (17)0.0183 (4)
H10A0.18090.51040.55270.022*
H10B0.21040.38940.51520.022*
C110.0273 (2)0.3510 (2)0.44359 (19)0.0252 (5)
H11A0.01810.27780.38240.030*
H11B−0.01100.39950.41800.030*
C12−0.0483 (2)0.2992 (3)0.5246 (2)0.0330 (6)
H12A−0.14100.24320.49200.050*
H12B−0.04060.37140.58470.050*
H12C−0.01150.24980.54920.050*
C130.6307 (2)0.76707 (19)0.47831 (16)0.0160 (4)
H13A0.67720.73800.42470.019*
H13B0.60550.82660.45680.019*
C140.7264 (2)0.8419 (2)0.58388 (16)0.0171 (4)
H14A0.68340.87760.63700.021*
H14B0.74880.78240.60820.021*
C150.8518 (2)0.9512 (2)0.57547 (18)0.0231 (5)
H15A0.82871.00880.54880.028*
H15B0.89560.91490.52370.028*
C160.9473 (2)1.0299 (2)0.6806 (2)0.0314 (5)
H16A1.02581.09910.67090.047*
H16B0.97250.97400.70650.047*
H16C0.90501.06740.73190.047*
C170.5490 (2)0.4027 (2)0.81372 (16)0.0154 (4)
C180.5934 (2)0.30563 (19)0.81605 (16)0.0155 (4)
C190.5912 (2)0.2678 (2)0.90565 (17)0.0210 (4)
C200.6303 (3)0.1737 (2)0.9064 (2)0.0295 (5)
H200.62810.14720.96660.035*
C210.6721 (3)0.1191 (2)0.8199 (2)0.0313 (6)
H210.69900.05560.82150.038*
C220.6754 (2)0.1561 (2)0.73042 (19)0.0250 (5)
H220.70440.11830.67120.030*
C230.6359 (2)0.2481 (2)0.72919 (17)0.0186 (4)
H230.63750.27320.66820.022*
C240.39034 (19)0.78038 (19)0.68108 (17)0.0148 (4)
C250.3413 (2)0.8755 (2)0.72378 (16)0.0167 (4)
C260.3334 (2)0.9564 (2)0.67047 (17)0.0179 (4)
C270.2884 (2)1.0455 (2)0.71614 (18)0.0224 (4)
H270.28291.10050.68010.027*
C280.2519 (2)1.0542 (2)0.81310 (19)0.0266 (5)
H280.22291.11620.84420.032*
C290.2572 (3)0.9720 (2)0.86622 (19)0.0286 (5)
H290.23070.97720.93260.034*
C300.3010 (2)0.8841 (2)0.82159 (19)0.0251 (5)
H300.30420.82800.85740.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01990 (8)0.01605 (8)0.01136 (8)0.01119 (6)0.00618 (5)0.00671 (6)
Sn20.01459 (8)0.01233 (8)0.01148 (8)0.00713 (6)0.00409 (5)0.00591 (5)
O10.0400 (10)0.0301 (9)0.0223 (8)0.0263 (8)0.0132 (7)0.0147 (7)
O20.0282 (8)0.0202 (7)0.0158 (7)0.0162 (7)0.0086 (6)0.0070 (6)
O30.0302 (8)0.0235 (8)0.0191 (7)0.0171 (7)0.0104 (6)0.0109 (6)
O40.0236 (7)0.0180 (7)0.0122 (7)0.0122 (6)0.0061 (6)0.0073 (6)
O50.0297 (8)0.0245 (8)0.0150 (7)0.0177 (7)0.0091 (6)0.0098 (6)
O60.0423 (10)0.0318 (9)0.0164 (8)0.0234 (8)0.0087 (7)0.0128 (7)
O70.0192 (7)0.0157 (7)0.0119 (6)0.0104 (6)0.0053 (5)0.0072 (5)
C10.0233 (11)0.0226 (11)0.0223 (11)0.0123 (9)0.0092 (9)0.0114 (9)
C20.0211 (11)0.0251 (11)0.0205 (10)0.0128 (9)0.0073 (8)0.0071 (9)
C30.0250 (12)0.0308 (12)0.0275 (12)0.0129 (10)0.0109 (9)0.0101 (10)
C40.0250 (13)0.0423 (15)0.0392 (16)0.0164 (12)0.0111 (11)0.0062 (12)
C50.0256 (11)0.0177 (10)0.0160 (10)0.0100 (9)0.0049 (8)0.0056 (8)
C60.0273 (12)0.0204 (11)0.0196 (10)0.0108 (9)0.0010 (9)0.0057 (9)
C70.0256 (11)0.0223 (11)0.0219 (11)0.0095 (9)0.0047 (9)0.0068 (9)
C80.0357 (14)0.0285 (13)0.0418 (15)0.0128 (12)−0.0047 (12)0.0097 (12)
C90.0166 (10)0.0213 (10)0.0147 (9)0.0089 (8)0.0035 (8)0.0071 (8)
C100.0170 (10)0.0202 (10)0.0182 (10)0.0078 (8)0.0049 (8)0.0079 (8)
C110.0197 (11)0.0267 (12)0.0240 (11)0.0065 (9)0.0041 (9)0.0078 (9)
C120.0210 (12)0.0326 (13)0.0364 (14)0.0031 (10)0.0091 (10)0.0125 (11)
C130.0202 (10)0.0154 (9)0.0148 (9)0.0084 (8)0.0065 (8)0.0075 (8)
C140.0198 (10)0.0152 (9)0.0161 (10)0.0074 (8)0.0043 (8)0.0057 (8)
C150.0206 (11)0.0201 (11)0.0245 (11)0.0056 (9)0.0064 (9)0.0075 (9)
C160.0219 (12)0.0273 (12)0.0337 (13)0.0053 (10)−0.0005 (10)0.0046 (10)
C170.0143 (9)0.0159 (9)0.0153 (10)0.0051 (8)0.0029 (7)0.0071 (8)
C180.0157 (9)0.0149 (9)0.0171 (10)0.0075 (8)0.0019 (7)0.0063 (8)
C190.0266 (11)0.0201 (10)0.0180 (10)0.0114 (9)0.0025 (8)0.0080 (9)
C200.0454 (15)0.0299 (13)0.0231 (12)0.0236 (12)0.0022 (10)0.0134 (10)
C210.0398 (14)0.0286 (13)0.0336 (13)0.0237 (12)−0.0009 (11)0.0101 (11)
C220.0294 (12)0.0228 (11)0.0260 (12)0.0168 (10)0.0041 (9)0.0051 (9)
C230.0200 (10)0.0180 (10)0.0193 (10)0.0096 (9)0.0036 (8)0.0070 (8)
C240.0125 (9)0.0123 (9)0.0200 (10)0.0049 (8)0.0049 (7)0.0067 (8)
C250.0185 (10)0.0172 (10)0.0159 (10)0.0096 (8)0.0044 (8)0.0050 (8)
C260.0194 (10)0.0195 (10)0.0172 (10)0.0099 (8)0.0057 (8)0.0078 (8)
C270.0273 (12)0.0220 (11)0.0261 (11)0.0154 (10)0.0093 (9)0.0125 (9)
C280.0326 (13)0.0279 (12)0.0274 (12)0.0219 (11)0.0098 (10)0.0071 (10)
C290.0425 (14)0.0348 (13)0.0210 (11)0.0258 (12)0.0156 (10)0.0124 (10)
C300.0350 (13)0.0290 (12)0.0224 (11)0.0210 (11)0.0109 (10)0.0132 (10)

Geometric parameters (Å, °)

Sn1—C12.134 (2)C9—H9A0.9900
Sn1—C52.130 (2)C9—H9B0.9900
Sn1—O12.217 (2)C10—C111.525 (3)
Sn1—O42.220 (1)C10—H10A0.9900
Sn1—O72.039 (1)C10—H10B0.9900
Sn2—C92.127 (2)C11—C121.528 (3)
Sn2—C132.124 (2)C11—H11A0.9900
Sn2—O22.327 (2)C11—H11B0.9900
Sn2—O4i2.674 (1)C12—H12A0.9800
Sn2—O72.046 (1)C12—H12B0.9800
Sn2—O7i2.148 (1)C12—H12C0.9800
Sn2—Sn2i3.2797 (3)C13—C141.527 (3)
O1—C241.254 (3)C13—H13A0.9900
O2—C241.272 (3)C13—H13B0.9900
O3—C261.355 (3)C14—C151.522 (3)
O3—H30.8400C14—H14A0.9900
O4—C171.290 (2)C14—H14B0.9900
O5—C171.249 (3)C15—C161.524 (3)
O6—C191.349 (3)C15—H15A0.9900
O6—H60.8400C15—H15B0.9900
O7—Sn2i2.1481 (14)C16—H16A0.9800
C1—C21.523 (3)C16—H16B0.9800
C1—H1A0.9900C16—H16C0.9800
C1—H1B0.9900C17—C181.478 (3)
C2—C31.526 (3)C18—C191.403 (3)
C2—H2A0.9900C18—C231.404 (3)
C2—H2B0.9900C19—C201.396 (3)
C3—C41.522 (3)C20—C211.381 (4)
C3—H3A0.9900C20—H200.9500
C3—H3B0.9900C21—C221.395 (4)
C4—H4A0.9800C21—H210.9500
C4—H4B0.9800C22—C231.378 (3)
C4—H4C0.9800C22—H220.9500
C5—C61.529 (3)C23—H230.9500
C5—H5A0.9900C24—C251.481 (3)
C5—H5B0.9900C25—C261.398 (3)
C6—C71.526 (3)C25—C301.403 (3)
C6—H6A0.9900C26—C271.396 (3)
C6—H6B0.9900C27—C281.376 (3)
C7—C81.511 (3)C27—H270.9500
C7—H7A0.9900C28—C291.400 (3)
C7—H7B0.9900C28—H280.9500
C8—H8A0.9800C29—C301.371 (3)
C8—H8B0.9800C29—H290.9500
C8—H8C0.9800C30—H300.9500
C9—C101.524 (3)
O7—Sn1—C5106.97 (7)Sn2—C9—H9A109.0
O7—Sn1—C1110.04 (7)C10—C9—H9B109.0
C1—Sn1—C5142.7 (1)Sn2—C9—H9B109.0
O7—Sn1—O188.26 (6)H9A—C9—H9B107.8
C5—Sn1—O186.54 (8)C9—C10—C11113.68 (18)
C1—Sn1—O190.33 (8)C9—C10—H10A108.8
O7—Sn1—O478.77 (5)C11—C10—H10A108.8
C5—Sn1—O496.61 (7)C9—C10—H10B108.8
C1—Sn1—O494.63 (7)C11—C10—H10B108.8
O1—Sn1—O4167.02 (6)H10A—C10—H10B107.7
O7—Sn2—C13109.41 (7)C10—C11—C12111.6 (2)
O7—Sn2—C9105.66 (7)C10—C11—H11A109.3
C9—Sn2—C13144.0 (1)C12—C11—H11A109.3
O7—Sn2—O7i77.15 (6)C10—C11—H11B109.3
C13—Sn2—O7i98.31 (7)C12—C11—H11B109.3
C9—Sn2—O7i97.06 (7)H11A—C11—H11B108.0
O7—Sn2—O292.54 (5)C11—C12—H12A109.5
C13—Sn2—O283.38 (7)C11—C12—H12B109.5
C9—Sn2—O287.28 (7)H12A—C12—H12B109.5
O7i—Sn2—O2169.55 (5)C11—C12—H12C109.5
O7—Sn2—O4i144.40 (5)H12A—C12—H12C109.5
C13—Sn2—O4i77.34 (6)H12B—C12—H12C109.5
C9—Sn2—O4i78.99 (6)C14—C13—Sn2115.51 (13)
O7i—Sn2—O4i67.25 (5)C14—C13—H13A108.4
O2—Sn2—O4i123.06 (5)Sn2—C13—H13A108.4
O7—Sn2—Sn2i39.68 (4)C14—C13—H13B108.4
C13—Sn2—Sn2i107.57 (6)Sn2—C13—H13B108.4
C9—Sn2—Sn2i104.41 (6)H13A—C13—H13B107.5
O7i—Sn2—Sn2i37.46 (4)C15—C14—C13111.74 (17)
O2—Sn2—Sn2i132.20 (4)C15—C14—H14A109.3
O4i—Sn2—Sn2i104.71 (3)C13—C14—H14A109.3
C24—O1—Sn1145.23 (14)C15—C14—H14B109.3
C24—O2—Sn2131.75 (13)C13—C14—H14B109.3
C26—O3—H3120.0H14A—C14—H14B107.9
C17—O4—Sn1109.71 (13)C14—C15—C16112.79 (19)
C19—O6—H6120.0C14—C15—H15A109.0
Sn1—O7—Sn2137.90 (7)C16—C15—H15A109.0
Sn1—O7—Sn2i119.21 (6)C14—C15—H15B109.0
Sn2—O7—Sn2i102.85 (6)C16—C15—H15B109.0
C2—C1—Sn1117.60 (15)H15A—C15—H15B107.8
C2—C1—H1A107.9C15—C16—H16A109.5
Sn1—C1—H1A107.9C15—C16—H16B109.5
C2—C1—H1B107.9H16A—C16—H16B109.5
Sn1—C1—H1B107.9C15—C16—H16C109.5
H1A—C1—H1B107.2H16A—C16—H16C109.5
C1—C2—C3112.06 (19)H16B—C16—H16C109.5
C1—C2—H2A109.2O5—C17—O4120.69 (19)
C3—C2—H2A109.2O5—C17—C18119.94 (18)
C1—C2—H2B109.2O4—C17—C18119.37 (18)
C3—C2—H2B109.2C19—C18—C23118.82 (19)
H2A—C2—H2B107.9C19—C18—C17119.86 (19)
C4—C3—C2112.4 (2)C23—C18—C17121.30 (19)
C4—C3—H3A109.1O6—C19—C20118.1 (2)
C2—C3—H3A109.1O6—C19—C18122.4 (2)
C4—C3—H3B109.1C20—C19—C18119.6 (2)
C2—C3—H3B109.1C21—C20—C19120.3 (2)
H3A—C3—H3B107.9C21—C20—H20119.8
C3—C4—H4A109.5C19—C20—H20119.8
C3—C4—H4B109.5C20—C21—C22120.8 (2)
H4A—C4—H4B109.5C20—C21—H21119.6
C3—C4—H4C109.5C22—C21—H21119.6
H4A—C4—H4C109.5C23—C22—C21119.0 (2)
H4B—C4—H4C109.5C23—C22—H22120.5
C6—C5—Sn1118.38 (15)C21—C22—H22120.5
C6—C5—H5A107.7C22—C23—C18121.5 (2)
Sn1—C5—H5A107.7C22—C23—H23119.3
C6—C5—H5B107.7C18—C23—H23119.3
Sn1—C5—H5B107.7O1—C24—O2123.73 (19)
H5A—C5—H5B107.1O1—C24—C25117.86 (18)
C7—C6—C5112.48 (19)O2—C24—C25118.40 (18)
C7—C6—H6A109.1C26—C25—C30119.1 (2)
C5—C6—H6A109.1C26—C25—C24122.59 (19)
C7—C6—H6B109.1C30—C25—C24118.34 (19)
C5—C6—H6B109.1O3—C26—C27117.32 (19)
H6A—C6—H6B107.8O3—C26—C25123.03 (19)
C8—C7—C6113.1 (2)C27—C26—C25119.6 (2)
C8—C7—H7A108.9C28—C27—C26120.4 (2)
C6—C7—H7A108.9C28—C27—H27119.8
C8—C7—H7B108.9C26—C27—H27119.8
C6—C7—H7B108.9C27—C28—C29120.4 (2)
H7A—C7—H7B107.8C27—C28—H28119.8
C7—C8—H8A109.5C29—C28—H28119.8
C7—C8—H8B109.5C30—C29—C28119.4 (2)
H8A—C8—H8B109.5C30—C29—H29120.3
C7—C8—H8C109.5C28—C29—H29120.3
H8A—C8—H8C109.5C29—C30—C25121.1 (2)
H8B—C8—H8C109.5C29—C30—H30119.5
C10—C9—Sn2112.74 (13)C25—C30—H30119.5
C10—C9—H9A109.0
O7—Sn1—O1—C24−4.1 (3)O4i—Sn2—C9—C10164.52 (16)
C5—Sn1—O1—C24103.0 (3)Sn2i—Sn2—C9—C1061.98 (15)
C1—Sn1—O1—C24−114.1 (3)Sn2—C9—C10—C11−175.14 (15)
O4—Sn1—O1—C24−1.5 (5)C9—C10—C11—C12−179.0 (2)
O7—Sn2—O2—C24−9.13 (19)O7—Sn2—C13—C14−22.38 (17)
C13—Sn2—O2—C24−118.38 (19)C9—Sn2—C13—C14144.04 (15)
C9—Sn2—O2—C2496.44 (19)O7i—Sn2—C13—C14−101.60 (15)
O7i—Sn2—O2—C24−18.4 (4)O2—Sn2—C13—C1467.99 (15)
O4i—Sn2—O2—C24171.42 (17)O4i—Sn2—C13—C14−165.93 (16)
Sn2i—Sn2—O2—C24−10.6 (2)Sn2i—Sn2—C13—C14−64.28 (15)
O7—Sn1—O4—C17−176.32 (14)Sn2—C13—C14—C15176.22 (14)
C5—Sn1—O4—C1777.63 (14)C13—C14—C15—C16178.31 (19)
C1—Sn1—O4—C17−66.79 (14)Sn1—O4—C17—O50.3 (2)
O1—Sn1—O4—C17−178.9 (2)Sn1—O4—C17—C18−179.56 (14)
C5—Sn1—O7—Sn2−86.37 (12)O5—C17—C18—C194.5 (3)
C1—Sn1—O7—Sn289.20 (12)O4—C17—C18—C19−175.62 (19)
O1—Sn1—O7—Sn2−0.52 (11)O5—C17—C18—C23−176.68 (19)
O4—Sn1—O7—Sn2−179.93 (12)O4—C17—C18—C233.2 (3)
C5—Sn1—O7—Sn2i96.30 (9)C23—C18—C19—O6−179.8 (2)
C1—Sn1—O7—Sn2i−88.14 (9)C17—C18—C19—O6−0.9 (3)
O1—Sn1—O7—Sn2i−177.85 (8)C23—C18—C19—C20−0.4 (3)
O4—Sn1—O7—Sn2i2.74 (7)C17—C18—C19—C20178.5 (2)
C13—Sn2—O7—Sn187.99 (12)O6—C19—C20—C21−180.0 (2)
C9—Sn2—O7—Sn1−83.77 (12)C18—C19—C20—C210.6 (4)
O7i—Sn2—O7—Sn1−177.61 (15)C19—C20—C21—C22−0.4 (4)
O2—Sn2—O7—Sn14.11 (11)C20—C21—C22—C23−0.1 (4)
O4i—Sn2—O7—Sn1−176.69 (7)C21—C22—C23—C180.4 (4)
Sn2i—Sn2—O7—Sn1−177.61 (15)C19—C18—C23—C22−0.1 (3)
C13—Sn2—O7—Sn2i−94.40 (8)C17—C18—C23—C22−178.9 (2)
C9—Sn2—O7—Sn2i93.84 (8)Sn1—O1—C24—O20.2 (4)
O7i—Sn2—O7—Sn2i0.0Sn1—O1—C24—C25179.42 (19)
O2—Sn2—O7—Sn2i−178.28 (6)Sn2—O2—C24—O18.3 (3)
O4i—Sn2—O7—Sn2i0.93 (12)Sn2—O2—C24—C25−170.89 (14)
O7—Sn1—C1—C2−106.97 (16)O1—C24—C25—C26170.7 (2)
C5—Sn1—C1—C266.0 (2)O2—C24—C25—C26−10.0 (3)
O1—Sn1—C1—C2−18.70 (17)O1—C24—C25—C30−9.4 (3)
O4—Sn1—C1—C2173.31 (16)O2—C24—C25—C30169.9 (2)
Sn1—C1—C2—C3−170.46 (16)C30—C25—C26—O3179.1 (2)
C1—C2—C3—C4−179.8 (2)C24—C25—C26—O3−1.0 (3)
O7—Sn1—C5—C6−104.35 (16)C30—C25—C26—C271.3 (3)
C1—Sn1—C5—C682.5 (2)C24—C25—C26—C27−178.9 (2)
O1—Sn1—C5—C6168.54 (17)O3—C26—C27—C28−178.0 (2)
O4—Sn1—C5—C6−24.11 (17)C25—C26—C27—C280.0 (3)
Sn1—C5—C6—C7171.31 (15)C26—C27—C28—C29−1.2 (4)
C5—C6—C7—C8173.7 (2)C27—C28—C29—C301.0 (4)
O7—Sn2—C9—C1020.85 (16)C28—C29—C30—C250.3 (4)
C13—Sn2—C9—C10−145.86 (15)C26—C25—C30—C29−1.4 (4)
O7i—Sn2—C9—C1099.42 (15)C24—C25—C30—C29178.7 (2)
O2—Sn2—C9—C10−71.03 (15)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.842.022.638 (2)130
O6—H6···O50.841.912.548 (2)132

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2287).

References

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  • Ng, S. W., Chen, W. & Kumar Das, V. G. (1991). J. Organomet. Chem.412, 39–45.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tiekink, E. R. T. (1991). Appl. Organomet. Chem.5, 1–23.
  • Tiekink, E. R. T. (1994). Trends Organomet. Chem.1, 71–116.
  • Westrip, S. P. (2008). publCIF In preparation.

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