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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m978.
Published online 2010 July 21. doi:  10.1107/S1600536810028321
PMCID: PMC3007486

catena-Poly[[tris­(4-fluoro­benz­yl)tin(IV)]-μ-2-[(piperidin-1-yl)carbothio­ylsulfan­yl]acetato-κ2 O:O′]

Abstract

Adjacent units of the title polymeric complex, [Sn(C7H6F)3(C8H12NO2S2)], are bridged by the carboxyl­ate ion into a helical chain running along the b axis. The Sn(IV) atom shows a distorted trans-C3SnO2 trigonal-bipyramidal coordination and is displaced by 0.113 (2) Å out of the C3Sn girdle in the direction of the covalently bonded O atom. The ring is disordered of two positions with an occupancy of 0.631 (4) for the major occupied site.

Related literature

For a comment on the repeat distance of carboxyl­ate-bridged trialkyl­tin carboxyl­ates, see: Ng et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m978-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6F)3(C8H12NO2S2)]
  • M r = 664.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m978-efi1.jpg
  • a = 11.8016 (7) Å
  • b = 10.4572 (6) Å
  • c = 23.0334 (13) Å
  • β = 94.013 (1)°
  • V = 2835.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.10 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.735, T max = 0.811
  • 25437 measured reflections
  • 6498 independent reflections
  • 5328 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.077
  • S = 1.05
  • 6498 reflections
  • 371 parameters
  • 17 restraints
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −1.19 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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, 2010 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028321/bt5300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028321/bt5300Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

Trialkyltin carboxylates generally adopt linear carboxylate-bridged motifs; the repeat distance of such polymers is independent of the nature of the carboxylate group. This feature of trialkyltin carboxylates is also borne out in tris(4-fluorobenzyl)tin (N-pentamethylenecarbamothio)sulfanylacetate (Scheme I), whose repeat distance, i.e., half the b-axis, of 5.23 Å, falls within the range of repeat distances reported (Ng et al., 1989). The tin atom shows trans-C3SnO2 trigonal bipyramidal coordination; the tin atom is displaced by 0.113 (2) Å out of the C3Sn girdle in the direction of the covalently-bonded oxygen atom. The O-Sn-O angle is close to linearity (Table 1).

Experimental

Tris(4-fluorobenzyl)tin hydroxide was prepared by hydrolysis of tris(4-fluorobenzyl)tin chloride in dilute sodium hydroxide. The hydroxide (1.0 g, 2.2 mmol) and N-piperinyldithiocarbamylacetic acid (0.48 g, 2.2 mmol) were heated in ethanol for an hour. The solution was filtered and then set aside for the growth of crystals.

Refinement

Hydrogen 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 carboxylate ion is disordered in the C–N(CH2)5 portion only; the sulfur atoms are ordered. Pairs of carbon-sulfur single-bond distances, carbon-sulfur double-bond distances, carbonsulfur-nitrogen distances, carbonmethylene-nitrogen distances and carbon-carbon (methylene) distances were restrained to within 0.01 Å of each other. The displacement parameters of the minor (primed) atoms were restrained to be similar to those of the major (unprimed) atoms. The two C(S2)–N(C2) fragments were restrained to be within 0.01 Å of a plane. The pairs of non-bonded sulfursingle bond-nitrogen and sulfurdouble bond-nitrogen distances were also restrained, though with a much tighter restraint.

The final difference Fourier map had a hole in the vicinity of O1.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of polymeric [Sn(C7H6F)3(C8H12NO2S2)]n; ellipsoids are drawn at the 70% probability level and H atoms are of arbitrary radius. The disorder is not shown. Symmetry code is given in Table ...

Crystal data

[Sn(C7H6F)3(C8H12NO2S2)]F(000) = 1344
Mr = 664.35Dx = 1.556 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9852 reflections
a = 11.8016 (7) Åθ = 2.4–28.3°
b = 10.4572 (6) ŵ = 1.10 mm1
c = 23.0334 (13) ÅT = 100 K
β = 94.013 (1)°Prism, colorless
V = 2835.6 (3) Å30.30 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer6498 independent reflections
Radiation source: fine-focus sealed tube5328 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.735, Tmax = 0.811k = −13→13
25437 measured reflectionsl = −29→29

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0254P)2 + 5.3214P] where P = (Fo2 + 2Fc2)/3
6498 reflections(Δ/σ)max = 0.001
371 parametersΔρmax = 0.50 e Å3
17 restraintsΔρmin = −1.19 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.710443 (15)0.543605 (18)0.737119 (9)0.01476 (6)
S10.57734 (6)0.05444 (7)0.62134 (3)0.01883 (15)
S20.68919 (7)0.25659 (8)0.55248 (4)0.02778 (18)
F10.20300 (17)0.7560 (2)0.79264 (11)0.0494 (6)
F20.2292 (2)0.5457 (3)0.56053 (13)0.0778 (10)
F31.0169 (2)0.7386 (2)0.52170 (10)0.0508 (6)
O10.61265 (18)0.39691 (19)0.68910 (10)0.0219 (5)
O20.71042 (17)0.22277 (19)0.71464 (9)0.0199 (4)
N10.7199 (2)0.0057 (3)0.54087 (13)0.0219 (9)0.631 (4)
N1'0.6619 (3)0.0131 (4)0.52047 (19)0.0219 (9)0.37
C10.6237 (2)0.5024 (3)0.81369 (13)0.0203 (6)
H1A0.61410.40880.81740.024*
H1B0.66990.53300.84850.024*
C20.5100 (2)0.5657 (3)0.81084 (13)0.0194 (6)
C30.4159 (3)0.5111 (3)0.78054 (14)0.0244 (7)
H30.42310.42940.76320.029*
C40.3121 (3)0.5734 (4)0.77516 (16)0.0318 (8)
H40.24790.53470.75510.038*
C50.3044 (3)0.6923 (4)0.79952 (16)0.0316 (8)
C60.3936 (3)0.7503 (3)0.83053 (16)0.0306 (8)
H60.38530.83220.84750.037*
C70.4965 (3)0.6853 (3)0.83628 (14)0.0236 (7)
H70.55900.72330.85800.028*
C80.6459 (3)0.6860 (3)0.67581 (14)0.0212 (6)
H8A0.63630.76710.69710.025*
H8B0.70370.70110.64740.025*
C90.5355 (2)0.6548 (3)0.64269 (13)0.0192 (6)
C100.4343 (3)0.7070 (4)0.65835 (15)0.0309 (8)
H100.43560.76840.68880.037*
C110.3307 (3)0.6717 (5)0.63062 (18)0.0463 (11)
H110.26170.70760.64200.056*
C120.3303 (3)0.5845 (5)0.58683 (19)0.0475 (11)
C130.4278 (3)0.5319 (4)0.56833 (16)0.0375 (9)
H130.42530.47250.53700.045*
C140.5303 (3)0.5679 (3)0.59670 (14)0.0249 (7)
H140.59880.53240.58450.030*
C150.8782 (2)0.4800 (3)0.71871 (13)0.0187 (6)
H15A0.93180.49670.75290.022*
H15B0.87690.38670.71140.022*
C160.9180 (2)0.5479 (3)0.66665 (13)0.0183 (6)
C170.8872 (3)0.5034 (3)0.61081 (14)0.0242 (7)
H170.84260.42800.60620.029*
C180.9200 (3)0.5665 (3)0.56162 (15)0.0324 (8)
H180.89830.53540.52370.039*
C190.9847 (3)0.6754 (3)0.56939 (16)0.0323 (8)
C201.0173 (3)0.7237 (3)0.62352 (16)0.0287 (7)
H201.06170.79940.62770.034*
C210.9836 (2)0.6587 (3)0.67181 (14)0.0222 (6)
H211.00580.69060.70950.027*
C220.6302 (2)0.2774 (3)0.68712 (12)0.0163 (6)
C230.5386 (2)0.2056 (3)0.65075 (13)0.0189 (6)
H23A0.51140.26150.61800.023*
H23B0.47380.19150.67510.023*
C240.6704 (3)0.1026 (4)0.56691 (15)0.0166 (13)0.631 (4)
C250.7999 (3)0.0258 (5)0.49474 (17)0.0273 (10)0.631 (4)
H25A0.8750−0.01030.50770.033*0.631 (4)
H25B0.80970.11870.48840.033*0.631 (4)
C260.7582 (5)−0.0356 (5)0.4389 (2)0.0273 (11)0.631 (4)
H26A0.8159−0.02550.41000.033*0.631 (4)
H26B0.68780.00760.42340.033*0.631 (4)
C270.7341 (5)−0.1788 (5)0.4475 (2)0.0275 (14)0.631 (4)
H27A0.6973−0.21500.41120.033*0.631 (4)
H27B0.8064−0.22490.45660.033*0.631 (4)
C280.6562 (5)−0.1965 (5)0.4974 (2)0.0292 (11)0.631 (4)
H28A0.5804−0.16070.48570.035*0.631 (4)
H28B0.6470−0.28890.50500.035*0.631 (4)
C290.7039 (3)−0.1307 (4)0.55303 (17)0.0224 (9)0.631 (4)
H29A0.6506−0.14110.58400.027*0.631 (4)
H29B0.7774−0.16990.56660.027*0.631 (4)
C24'0.6478 (3)0.1059 (6)0.5589 (3)0.029 (3)0.369 (4)
C25'0.7185 (5)0.0395 (8)0.4665 (3)0.0273 (10)0.37
H25C0.74720.12850.46720.033*0.369 (4)
H25D0.66320.03020.43240.033*0.369 (4)
C26'0.8152 (7)−0.0511 (8)0.4610 (4)0.0273 (11)0.37
H26C0.8744−0.03490.49270.033*0.369 (4)
H26D0.8491−0.03650.42350.033*0.369 (4)
C27'0.7748 (9)−0.1904 (9)0.4642 (4)0.0275 (14)0.37
H27C0.7178−0.20820.43150.033*0.369 (4)
H27D0.8398−0.24910.46090.033*0.369 (4)
C28'0.7223 (7)−0.2116 (8)0.5220 (4)0.0292 (11)0.37
H28C0.6947−0.30070.52440.035*0.369 (4)
H28D0.7801−0.19720.55460.035*0.369 (4)
C29'0.6248 (5)−0.1199 (6)0.5267 (3)0.0224 (9)0.37
H29C0.5644−0.13950.49590.027*0.369 (4)
H29D0.5925−0.13080.56490.027*0.369 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01313 (9)0.01198 (9)0.01910 (10)0.00144 (8)0.00059 (7)0.00057 (8)
S10.0223 (3)0.0147 (3)0.0196 (4)−0.0040 (3)0.0021 (3)−0.0018 (3)
S20.0371 (4)0.0163 (4)0.0304 (5)−0.0072 (3)0.0054 (4)0.0006 (3)
F10.0236 (10)0.0570 (15)0.0692 (16)0.0201 (10)0.0158 (10)0.0259 (13)
F20.0422 (14)0.109 (2)0.076 (2)−0.0369 (16)−0.0362 (13)0.0325 (18)
F30.0663 (16)0.0503 (14)0.0387 (13)−0.0086 (12)0.0230 (12)0.0114 (11)
O10.0226 (11)0.0145 (10)0.0276 (12)0.0009 (8)−0.0042 (9)−0.0019 (9)
O20.0204 (10)0.0144 (10)0.0238 (11)−0.0009 (8)−0.0049 (8)0.0033 (9)
N10.029 (2)0.0191 (16)0.018 (2)−0.0064 (18)0.0059 (16)−0.0010 (15)
N1'0.029 (2)0.0191 (16)0.018 (2)−0.0064 (18)0.0059 (16)−0.0010 (15)
C10.0197 (14)0.0210 (14)0.0204 (15)−0.0020 (11)0.0023 (12)0.0036 (12)
C20.0194 (14)0.0190 (15)0.0200 (15)−0.0025 (11)0.0038 (11)0.0052 (12)
C30.0199 (15)0.0256 (16)0.0275 (17)−0.0024 (12)0.0013 (13)0.0032 (13)
C40.0148 (15)0.046 (2)0.034 (2)−0.0019 (14)0.0005 (13)0.0118 (16)
C50.0184 (15)0.038 (2)0.040 (2)0.0098 (14)0.0113 (14)0.0173 (16)
C60.0315 (18)0.0217 (16)0.041 (2)0.0036 (13)0.0173 (16)0.0063 (15)
C70.0202 (15)0.0235 (16)0.0282 (17)−0.0050 (12)0.0091 (13)0.0018 (13)
C80.0239 (15)0.0146 (14)0.0244 (16)0.0028 (12)−0.0032 (12)0.0069 (12)
C90.0203 (14)0.0169 (14)0.0201 (15)0.0011 (11)−0.0004 (12)0.0063 (12)
C100.0258 (16)0.039 (2)0.0282 (18)0.0087 (15)0.0018 (14)0.0041 (15)
C110.0193 (17)0.074 (3)0.046 (2)0.0072 (18)−0.0001 (16)0.018 (2)
C120.0280 (19)0.068 (3)0.044 (2)−0.0182 (19)−0.0180 (17)0.022 (2)
C130.050 (2)0.033 (2)0.0270 (18)−0.0134 (18)−0.0155 (16)0.0071 (16)
C140.0317 (17)0.0224 (17)0.0198 (16)0.0013 (13)−0.0029 (13)0.0035 (12)
C150.0153 (13)0.0154 (15)0.0257 (16)0.0013 (11)0.0031 (11)−0.0023 (12)
C160.0139 (12)0.0161 (13)0.0251 (15)0.0020 (11)0.0029 (11)−0.0029 (12)
C170.0246 (15)0.0193 (14)0.0286 (17)−0.0020 (12)0.0016 (13)−0.0034 (13)
C180.0383 (19)0.034 (2)0.0250 (18)−0.0007 (15)0.0039 (15)−0.0038 (15)
C190.0365 (19)0.0315 (19)0.0306 (19)0.0003 (15)0.0145 (15)0.0069 (15)
C200.0232 (16)0.0233 (16)0.041 (2)−0.0021 (13)0.0110 (14)0.0004 (15)
C210.0175 (14)0.0209 (15)0.0284 (17)−0.0005 (12)0.0036 (12)−0.0066 (13)
C220.0183 (13)0.0146 (14)0.0162 (14)0.0004 (11)0.0016 (11)−0.0016 (11)
C230.0197 (14)0.0130 (14)0.0237 (16)0.0012 (11)−0.0007 (12)−0.0037 (12)
C240.025 (3)0.014 (3)0.012 (3)−0.007 (2)0.004 (2)−0.001 (2)
C250.031 (2)0.026 (2)0.026 (2)−0.007 (2)0.0096 (17)−0.001 (2)
C260.033 (3)0.033 (2)0.016 (3)−0.006 (3)0.0051 (18)−0.002 (2)
C270.029 (4)0.032 (2)0.022 (3)−0.007 (3)0.001 (2)−0.009 (2)
C280.035 (3)0.025 (2)0.028 (3)−0.011 (2)0.010 (2)−0.007 (2)
C290.033 (2)0.018 (2)0.017 (2)−0.0037 (19)0.0049 (16)−0.0008 (17)
C24'0.034 (6)0.023 (7)0.030 (7)−0.003 (5)−0.006 (5)−0.001 (5)
C25'0.031 (2)0.026 (2)0.026 (2)−0.007 (2)0.0096 (17)−0.001 (2)
C26'0.033 (3)0.033 (2)0.016 (3)−0.006 (3)0.0051 (18)−0.002 (2)
C27'0.029 (4)0.032 (2)0.022 (3)−0.007 (3)0.001 (2)−0.009 (2)
C28'0.035 (3)0.025 (2)0.028 (3)−0.011 (2)0.010 (2)−0.007 (2)
C29'0.033 (2)0.018 (2)0.017 (2)−0.0037 (19)0.0049 (16)−0.0008 (17)

Geometric parameters (Å, °)

Sn1—C12.144 (3)C13—H130.9500
Sn1—C82.155 (3)C14—H140.9500
Sn1—C152.158 (3)C15—C161.498 (4)
Sn1—O12.175 (2)C15—H15A0.9900
Sn1—O2i2.339 (2)C15—H15B0.9900
S1—C24'1.793 (7)C16—C171.392 (4)
S1—C231.792 (3)C16—C211.394 (4)
S1—C241.796 (5)C17—C181.390 (5)
S2—C24'1.659 (7)C17—H170.9500
S2—C241.662 (5)C18—C191.376 (5)
F1—C51.369 (4)C18—H180.9500
F2—C121.362 (4)C19—C201.375 (5)
F3—C191.358 (4)C20—C211.385 (5)
O1—C221.268 (3)C20—H200.9500
O2—C221.241 (3)C21—H210.9500
O2—Sn1ii2.339 (2)C22—C231.518 (4)
N1—C241.333 (6)C23—H23A0.9900
N1—C291.468 (5)C23—H23B0.9900
N1—C251.485 (5)C25—C261.490 (6)
N1'—C24'1.332 (8)C25—H25A0.9900
N1'—C29'1.468 (7)C25—H25B0.9900
N1'—C25'1.479 (7)C26—C271.540 (6)
C1—C21.494 (4)C26—H26A0.9900
C1—H1A0.9900C26—H26B0.9900
C1—H1B0.9900C27—C281.530 (6)
C2—C31.392 (4)C27—H27A0.9900
C2—C71.395 (4)C27—H27B0.9900
C3—C41.386 (4)C28—C291.527 (6)
C3—H30.9500C28—H28A0.9900
C4—C51.369 (5)C28—H28B0.9900
C4—H40.9500C29—H29A0.9900
C5—C61.371 (5)C29—H29B0.9900
C6—C71.389 (4)C25'—C26'1.495 (8)
C6—H60.9500C25'—H25C0.9900
C7—H70.9500C25'—H25D0.9900
C8—C91.499 (4)C26'—C27'1.535 (9)
C8—H8A0.9900C26'—H26C0.9900
C8—H8B0.9900C26'—H26D0.9900
C9—C101.384 (4)C27'—C28'1.525 (8)
C9—C141.394 (4)C27'—H27C0.9900
C10—C111.389 (5)C27'—H27D0.9900
C10—H100.9500C28'—C29'1.507 (8)
C11—C121.359 (6)C28'—H28C0.9900
C11—H110.9500C28'—H28D0.9900
C12—C131.370 (6)C29'—H29C0.9900
C13—C141.386 (5)C29'—H29D0.9900
C1—Sn1—C8120.72 (12)F3—C19—C18118.8 (3)
C1—Sn1—C15126.65 (11)C20—C19—C18122.6 (3)
C8—Sn1—C15111.80 (12)C19—C20—C21118.1 (3)
C1—Sn1—O190.56 (10)C19—C20—H20121.0
C8—Sn1—O190.20 (10)C21—C20—H20121.0
C15—Sn1—O198.28 (10)C20—C21—C16121.9 (3)
C1—Sn1—O2i88.16 (10)C20—C21—H21119.1
C8—Sn1—O2i82.46 (10)C16—C21—H21119.1
C15—Sn1—O2i89.94 (9)O2—C22—O1123.7 (3)
O1—Sn1—O2i170.59 (7)O2—C22—C23122.8 (3)
C24'—S1—C23100.5 (2)O1—C22—C23113.3 (2)
C23—S1—C24101.60 (18)C22—C23—S1117.0 (2)
C22—O1—Sn1129.16 (19)C22—C23—H23A108.0
C22—O2—Sn1ii151.17 (19)S1—C23—H23A108.0
C24—N1—C29125.9 (4)C22—C23—H23B108.0
C24—N1—C25122.3 (4)S1—C23—H23B108.0
C29—N1—C25111.8 (4)H23A—C23—H23B107.3
C24'—N1'—C29'125.0 (5)N1—C24—S2125.3 (3)
C24'—N1'—C25'120.6 (6)N1—C24—S1114.2 (3)
C29'—N1'—C25'114.5 (5)S2—C24—S1120.5 (3)
C2—C1—Sn1110.7 (2)N1—C25—C26111.6 (3)
C2—C1—H1A109.5N1—C25—H25A109.3
Sn1—C1—H1A109.5C26—C25—H25A109.3
C2—C1—H1B109.5N1—C25—H25B109.3
Sn1—C1—H1B109.5C26—C25—H25B109.3
H1A—C1—H1B108.1H25A—C25—H25B108.0
C3—C2—C7117.9 (3)C25—C26—C27111.1 (4)
C3—C2—C1121.5 (3)C25—C26—H26A109.4
C7—C2—C1120.5 (3)C27—C26—H26A109.4
C4—C3—C2121.4 (3)C25—C26—H26B109.4
C4—C3—H3119.3C27—C26—H26B109.4
C2—C3—H3119.3H26A—C26—H26B108.0
C5—C4—C3118.3 (3)C28—C27—C26109.9 (4)
C5—C4—H4120.9C28—C27—H27A109.7
C3—C4—H4120.9C26—C27—H27A109.7
C4—C5—F1118.5 (3)C28—C27—H27B109.7
C4—C5—C6123.0 (3)C26—C27—H27B109.7
F1—C5—C6118.5 (3)H27A—C27—H27B108.2
C5—C6—C7117.8 (3)C29—C28—C27111.7 (4)
C5—C6—H6121.1C29—C28—H28A109.3
C7—C6—H6121.1C27—C28—H28A109.3
C6—C7—C2121.5 (3)C29—C28—H28B109.3
C6—C7—H7119.2C27—C28—H28B109.3
C2—C7—H7119.2H28A—C28—H28B107.9
C9—C8—Sn1116.0 (2)N1—C29—C28108.8 (3)
C9—C8—H8A108.3N1—C29—H29A109.9
Sn1—C8—H8A108.3C28—C29—H29A109.9
C9—C8—H8B108.3N1—C29—H29B109.9
Sn1—C8—H8B108.3C28—C29—H29B109.9
H8A—C8—H8B107.4H29A—C29—H29B108.3
C10—C9—C14117.6 (3)N1'—C24'—S2125.5 (5)
C10—C9—C8121.1 (3)N1'—C24'—S1113.6 (5)
C14—C9—C8121.2 (3)S2—C24'—S1120.9 (4)
C9—C10—C11121.5 (4)N1'—C25'—C26'110.2 (5)
C9—C10—H10119.2N1'—C25'—H25C109.6
C11—C10—H10119.2C26'—C25'—H25C109.6
C12—C11—C10118.5 (4)N1'—C25'—H25D109.6
C12—C11—H11120.8C26'—C25'—H25D109.6
C10—C11—H11120.8H25C—C25'—H25D108.1
C11—C12—F2119.1 (4)C25'—C26'—C27'110.9 (8)
C11—C12—C13122.8 (3)C25'—C26'—H26C109.5
F2—C12—C13118.1 (4)C27'—C26'—H26C109.5
C12—C13—C14117.9 (4)C25'—C26'—H26D109.5
C12—C13—H13121.0C27'—C26'—H26D109.5
C14—C13—H13121.0H26C—C26'—H26D108.1
C13—C14—C9121.7 (3)C28'—C27'—C26'109.0 (8)
C13—C14—H14119.2C28'—C27'—H27C109.9
C9—C14—H14119.2C26'—C27'—H27C109.9
C16—C15—Sn1110.79 (19)C28'—C27'—H27D109.9
C16—C15—H15A109.5C26'—C27'—H27D109.9
Sn1—C15—H15A109.5H27C—C27'—H27D108.3
C16—C15—H15B109.5C29'—C28'—C27'109.2 (8)
Sn1—C15—H15B109.5C29'—C28'—H28C109.8
H15A—C15—H15B108.1C27'—C28'—H28C109.8
C17—C16—C21117.7 (3)C29'—C28'—H28D109.8
C17—C16—C15120.3 (3)C27'—C28'—H28D109.8
C21—C16—C15122.0 (3)H28C—C28'—H28D108.3
C18—C17—C16121.7 (3)N1'—C29'—C28'111.2 (5)
C18—C17—H17119.2N1'—C29'—H29C109.4
C16—C17—H17119.2C28'—C29'—H29C109.4
C19—C18—C17118.1 (3)N1'—C29'—H29D109.4
C19—C18—H18121.0C28'—C29'—H29D109.4
C17—C18—H18121.0H29C—C29'—H29D108.0
F3—C19—C20118.6 (3)
C1—Sn1—O1—C22−83.6 (3)C19—C20—C21—C16−0.3 (5)
C8—Sn1—O1—C22155.7 (3)C17—C16—C21—C200.2 (4)
C15—Sn1—O1—C2243.6 (3)C15—C16—C21—C20−177.9 (3)
C8—Sn1—C1—C210.2 (3)Sn1ii—O2—C22—O1149.7 (3)
C15—Sn1—C1—C2178.85 (19)Sn1ii—O2—C22—C23−26.1 (6)
O1—Sn1—C1—C2−80.4 (2)Sn1—O1—C22—O20.8 (4)
O2i—Sn1—C1—C290.3 (2)Sn1—O1—C22—C23177.03 (18)
Sn1—C1—C2—C382.4 (3)O2—C22—C23—S1−27.3 (4)
Sn1—C1—C2—C7−94.3 (3)O1—C22—C23—S1156.4 (2)
C7—C2—C3—C40.6 (5)C24'—S1—C23—C22−80.7 (2)
C1—C2—C3—C4−176.3 (3)C24—S1—C23—C22−70.5 (2)
C2—C3—C4—C51.3 (5)C29—N1—C24—S2−179.80 (10)
C3—C4—C5—F1177.8 (3)C25—N1—C24—S20.15 (17)
C3—C4—C5—C6−2.2 (5)C29—N1—C24—S10.16 (15)
C4—C5—C6—C71.2 (5)C25—N1—C24—S1−179.89 (8)
F1—C5—C6—C7−178.9 (3)C24'—S2—C24—N1100.1 (16)
C5—C6—C7—C20.9 (5)C24'—S2—C24—S1−79.9 (16)
C3—C2—C7—C6−1.7 (4)C24'—S1—C24—N1−100.3 (15)
C1—C2—C7—C6175.2 (3)C23—S1—C24—N1174.76 (15)
C1—Sn1—C8—C9−67.4 (3)C24'—S1—C24—S279.7 (15)
C15—Sn1—C8—C9122.4 (2)C23—S1—C24—S2−5.27 (16)
O1—Sn1—C8—C923.4 (2)C24—N1—C25—C26−119.8 (4)
O2i—Sn1—C8—C9−150.7 (2)C29—N1—C25—C2660.2 (4)
Sn1—C8—C9—C10101.0 (3)N1—C25—C26—C27−55.1 (6)
Sn1—C8—C9—C14−76.1 (3)C25—C26—C27—C2852.1 (6)
C14—C9—C10—C111.9 (5)C26—C27—C28—C29−53.8 (6)
C8—C9—C10—C11−175.3 (3)C24—N1—C29—C28120.1 (4)
C9—C10—C11—C12−0.6 (6)C25—N1—C29—C28−59.9 (3)
C10—C11—C12—F2177.8 (4)C27—C28—C29—N157.6 (5)
C10—C11—C12—C13−1.1 (6)C29'—N1'—C24'—S2−179.98 (10)
C11—C12—C13—C141.4 (6)C25'—N1'—C24'—S20.02 (17)
F2—C12—C13—C14−177.6 (3)C29'—N1'—C24'—S10.01 (15)
C12—C13—C14—C90.0 (5)C25'—N1'—C24'—S1−179.99 (8)
C10—C9—C14—C13−1.6 (5)C24—S2—C24'—N1'−98.2 (16)
C8—C9—C14—C13175.6 (3)C24—S2—C24'—S181.8 (16)
C1—Sn1—C15—C16−169.27 (19)C23—S1—C24'—N1'−164.49 (17)
C8—Sn1—C15—C160.3 (2)C24—S1—C24'—N1'98.5 (15)
O1—Sn1—C15—C1693.8 (2)C23—S1—C24'—S215.51 (17)
O2i—Sn1—C15—C16−81.6 (2)C24—S1—C24'—S2−81.5 (15)
Sn1—C15—C16—C17−84.4 (3)C24'—N1'—C25'—C26'125.9 (6)
Sn1—C15—C16—C2193.6 (3)C29'—N1'—C25'—C26'−54.1 (6)
C21—C16—C17—C18−0.1 (5)N1'—C25'—C26'—C27'55.3 (9)
C15—C16—C17—C18178.0 (3)C25'—C26'—C27'—C28'−58.9 (10)
C16—C17—C18—C190.1 (5)C26'—C27'—C28'—C29'58.6 (10)
C17—C18—C19—F3−179.7 (3)C24'—N1'—C29'—C28'−124.7 (6)
C17—C18—C19—C20−0.3 (5)C25'—N1'—C29'—C28'55.3 (6)
F3—C19—C20—C21179.8 (3)C27'—C28'—C29'—N1'−56.7 (9)
C18—C19—C20—C210.4 (5)

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5300).

References

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  • Ng, S. W., Chen, W. & Kumar Das, V. G. (1989). J. Organomet. Chem.346, 59–64.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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