PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m112.
Published online 2010 January 9. doi:  10.1107/S1600536809055135
PMCID: PMC2979966

(μ-2,3-Dihydroxy­butane-1,4-dithiol­ato)bis­[triphenyl­tin(IV)]

Abstract

In the title compound, [Sn2(C6H5)6(C4H8O2S2)], the geometry around the Sn atoms is distorted tetra­hedral. The hydr­oxy groups are involved in O—H(...)O hydrogen bonding, which connects mol­ecules into centrosymmetric dimers.

Related literature

For related structures, see: Basu Baul (2008 [triangle]); Ma & Zhang (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m112-scheme1.jpg

Experimental

Crystal data

  • [Sn2(C6H5)6(C4H8O2S2)]
  • M r = 852.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m112-efi1.jpg
  • a = 10.4806 (4) Å
  • b = 12.3774 (5) Å
  • c = 14.9797 (6) Å
  • α = 104.656 (1)°
  • β = 90.470 (1)°
  • γ = 95.521 (1)°
  • V = 1870.19 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.48 mm−1
  • T = 293 K
  • 0.25 × 0.22 × 0.21 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.709, T max = 0.746
  • 21325 measured reflections
  • 6551 independent reflections
  • 5739 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.057
  • S = 1.06
  • 6551 reflections
  • 417 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055135/gk2249sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055135/gk2249Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (20271025) and the Director Foundation of the National Natural Science Foundation Committee of China (20741008) for financial support.

supplementary crystallographic information

Comment

Since some triphenyltin(IV) compounds have been found to exhibit antimicrobial activity, varieties of triorganotin(IV) compounds have been synthesized and studied in the context of their antimicrobial potential (Basu Baul, 2008). 1,4-dithioerythritol is a protective agent for preventing oxidation of thiol groups and a reagent for the reduction of disulfide groups in proteins. Our interest has been focused on studying the reaction under a mild condition and hoping to obtain a new organotin complex with potential biological activities. Here, we have synthesized the title compound and present its crystal structure. The title compound, which is shown in Fig.1 forms a dimer structure by O—H···O hydrogen bonding. The ligand is coordinated to Sn atoms by the sulfur atoms. The Sn—S bond distances in the compound (Sn(1)—S(1) = 2.416 (7) Å; Sn(2)—S(2) = 2.4087 (8) Å) are comparable to those found in related organotin complexes (Ma et al., 2006). The Sn atom assumes a distorted tetrahedron geometry defined by three carbon atoms of the three phenyl groups and one sulfur atom of the dithioerythriol fragment.

Experimental

The reaction was carried out under nitrogen atmosphere. 1,4-Dithioerythritol (1 mmol) and sodium ethoxide (2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenyltin chloride (2 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from ether to yield colourless blocks of compound (yield 81%;. m.p.355 K). Anal. Calcd (%) for C40H38O2S2Sn2 (Mr = 852.20): C, 56.37; H, 4.49; Found (%): C, 56.01; H, 4.05.

Refinement

The H atoms were positioned geometrically, with methylene C—H distances of 0.97 Å, methine C—H distances of 0.98 Å, hydroxy O—H distances of 0.82 Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O).

Figures

Fig. 1.
The molecular structure of the compound, showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
Fig. 2.
The dimer structure of the compound via O—H···O hydrogen-bonding. Hydrogen bonds are shown with dashed lines.

Crystal data

[Sn2(C6H5)6(C4H8O2S2)]Z = 2
Mr = 852.20F(000) = 852
Triclinic, P1Dx = 1.513 Mg m3
a = 10.4806 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.3774 (5) ÅCell parameters from 6651 reflections
c = 14.9797 (6) Åθ = 2.4–28.1°
α = 104.656 (1)°µ = 1.48 mm1
β = 90.470 (1)°T = 293 K
γ = 95.521 (1)°Block, colorless
V = 1870.19 (13) Å30.25 × 0.22 × 0.21 mm

Data collection

Siemens SMART CCD area-detector diffractometer6551 independent reflections
Radiation source: fine-focus sealed tube5739 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→12
Tmin = 0.709, Tmax = 0.746k = −14→14
21325 measured reflectionsl = −17→17

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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0235P)2 + 0.9814P] where P = (Fo2 + 2Fc2)/3
6551 reflections(Δ/σ)max = 0.001
417 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.51 e Å3

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

xyzUiso*/Ueq
Sn10.268290 (16)0.706634 (14)0.364645 (12)0.04754 (6)
Sn20.148861 (17)1.096900 (14)0.869657 (12)0.05017 (6)
S10.32886 (8)0.88504 (6)0.33085 (5)0.06081 (18)
S20.26878 (8)1.17374 (6)0.75957 (5)0.0673 (2)
O10.14670 (17)0.89633 (14)0.49766 (13)0.0532 (4)
H10.07170.88680.47900.080*
O20.08474 (18)1.11808 (17)0.59391 (15)0.0680 (6)
H20.08451.16620.64290.102*
C10.3363 (3)0.9801 (2)0.44574 (18)0.0538 (6)
H1A0.38550.94940.48690.065*
H1B0.38111.05150.44330.065*
C20.2049 (2)0.9995 (2)0.48472 (17)0.0468 (6)
H2A0.15251.02220.43940.056*
C30.2131 (2)1.0918 (2)0.57454 (17)0.0480 (6)
H30.26371.15830.56470.058*
C40.2726 (3)1.0593 (2)0.65489 (17)0.0534 (6)
H4A0.36061.04410.64200.064*
H4B0.22560.99170.66390.064*
C50.3487 (2)0.5930 (2)0.25173 (17)0.0495 (6)
C60.2951 (3)0.4833 (2)0.2183 (2)0.0592 (7)
H60.22030.45880.24350.071*
C70.3508 (3)0.4094 (2)0.1481 (2)0.0711 (9)
H70.31380.33580.12670.085*
C80.4600 (3)0.4441 (3)0.1101 (2)0.0763 (9)
H80.49770.39430.06310.092*
C90.5134 (3)0.5517 (3)0.1412 (2)0.0813 (10)
H90.58750.57570.11500.098*
C100.4586 (3)0.6258 (3)0.2114 (2)0.0676 (8)
H100.49640.69920.23190.081*
C110.3686 (3)0.7025 (2)0.48780 (19)0.0553 (6)
C120.3202 (3)0.7338 (3)0.5750 (2)0.0703 (8)
H120.24060.76160.58250.084*
C130.3891 (4)0.7242 (3)0.6515 (2)0.0896 (11)
H130.35440.74380.70960.107*
C140.5063 (5)0.6865 (4)0.6420 (3)0.1076 (15)
H140.55250.68070.69350.129*
C150.5558 (4)0.6574 (5)0.5573 (3)0.1245 (19)
H150.63670.63180.55090.149*
C160.4885 (4)0.6649 (4)0.4801 (3)0.0962 (13)
H160.52420.64450.42240.115*
C170.0695 (2)0.6466 (2)0.35832 (18)0.0491 (6)
C180.0085 (3)0.6228 (3)0.4331 (2)0.0695 (8)
H180.05300.63740.48960.083*
C19−0.1188 (4)0.5772 (3)0.4252 (3)0.0876 (11)
H19−0.15870.56050.47600.105*
C20−0.1855 (3)0.5567 (3)0.3428 (3)0.0843 (11)
H20−0.27080.52640.33770.101*
C21−0.1268 (3)0.5806 (3)0.2681 (3)0.0754 (9)
H21−0.17240.56760.21220.090*
C220.0002 (3)0.6243 (2)0.2755 (2)0.0601 (7)
H220.03990.63910.22400.072*
C230.0050 (3)1.2060 (2)0.91919 (18)0.0540 (6)
C24−0.1185 (3)1.1839 (3)0.8829 (2)0.0702 (8)
H24−0.14091.11880.83650.084*
C25−0.2100 (4)1.2566 (4)0.9142 (3)0.0866 (11)
H25−0.29291.24070.88850.104*
C26−0.1792 (5)1.3503 (4)0.9816 (3)0.0985 (13)
H26−0.24111.39871.00320.118*
C27−0.0575 (5)1.3747 (4)1.0187 (3)0.1061 (14)
H27−0.03641.44011.06490.127*
C280.0348 (4)1.3026 (3)0.9878 (2)0.0831 (10)
H280.11751.31971.01360.100*
C290.2827 (3)1.1052 (2)0.97950 (19)0.0562 (7)
C300.4117 (3)1.1355 (2)0.9722 (2)0.0643 (7)
H300.44091.15330.91870.077*
C310.4979 (4)1.1397 (3)1.0439 (3)0.0791 (10)
H310.58461.16041.03840.095*
C320.4560 (4)1.1139 (3)1.1217 (3)0.0842 (11)
H320.51471.11571.16910.101*
C330.3296 (4)1.0853 (3)1.1320 (2)0.0867 (11)
H330.30201.06861.18620.104*
C340.2418 (3)1.0812 (3)1.0608 (2)0.0748 (9)
H340.15511.06221.06770.090*
C350.0722 (3)0.9308 (2)0.8010 (2)0.0586 (7)
C360.1106 (4)0.8400 (3)0.8278 (3)0.0833 (10)
H360.16680.85090.87830.100*
C370.0645 (5)0.7317 (3)0.7786 (3)0.1062 (14)
H370.09060.67030.79650.127*
C38−0.0173 (5)0.7151 (3)0.7056 (3)0.1021 (15)
H38−0.04720.64240.67340.123*
C39−0.0565 (4)0.8034 (3)0.6785 (3)0.0960 (13)
H39−0.11310.79140.62800.115*
C40−0.0119 (4)0.9115 (3)0.7263 (2)0.0767 (9)
H40−0.03920.97210.70780.092*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.04155 (11)0.04929 (11)0.04692 (10)0.00313 (8)0.00315 (7)0.00384 (8)
Sn20.05062 (12)0.04580 (11)0.04939 (11)0.00212 (8)−0.00149 (8)0.00462 (8)
S10.0731 (5)0.0534 (4)0.0516 (4)0.0025 (3)0.0115 (3)0.0066 (3)
S20.0790 (5)0.0557 (4)0.0538 (4)−0.0181 (4)0.0069 (4)−0.0015 (3)
O10.0422 (10)0.0448 (10)0.0654 (11)−0.0024 (8)−0.0035 (9)0.0034 (8)
O20.0453 (11)0.0628 (13)0.0823 (14)0.0190 (9)−0.0079 (10)−0.0113 (10)
C10.0486 (16)0.0477 (15)0.0582 (16)−0.0006 (12)0.0023 (12)0.0028 (12)
C20.0427 (14)0.0410 (13)0.0520 (14)0.0033 (11)−0.0068 (11)0.0037 (11)
C30.0398 (14)0.0417 (13)0.0562 (15)0.0013 (10)−0.0028 (11)0.0021 (11)
C40.0485 (15)0.0536 (15)0.0513 (14)0.0056 (12)−0.0014 (12)0.0007 (12)
C50.0468 (15)0.0491 (14)0.0481 (14)0.0067 (12)0.0008 (11)0.0035 (11)
C60.0567 (17)0.0518 (16)0.0659 (17)0.0019 (13)0.0031 (14)0.0103 (13)
C70.081 (2)0.0490 (17)0.072 (2)0.0083 (15)−0.0087 (17)−0.0047 (14)
C80.080 (2)0.069 (2)0.068 (2)0.0217 (18)0.0108 (17)−0.0089 (16)
C90.070 (2)0.081 (2)0.082 (2)0.0082 (18)0.0277 (18)−0.0009 (18)
C100.0588 (19)0.0565 (17)0.075 (2)−0.0015 (14)0.0154 (15)−0.0033 (14)
C110.0533 (16)0.0550 (16)0.0534 (15)0.0082 (13)−0.0033 (12)0.0052 (12)
C120.066 (2)0.082 (2)0.0578 (17)0.0133 (16)−0.0049 (15)0.0072 (15)
C130.098 (3)0.108 (3)0.0561 (19)0.011 (2)−0.0100 (19)0.0087 (19)
C140.116 (4)0.127 (4)0.076 (3)0.040 (3)−0.035 (2)0.009 (2)
C150.101 (3)0.167 (5)0.097 (3)0.076 (3)−0.026 (3)−0.005 (3)
C160.077 (2)0.134 (3)0.070 (2)0.047 (2)−0.0063 (19)−0.001 (2)
C170.0416 (14)0.0411 (13)0.0598 (15)0.0053 (11)0.0068 (12)0.0037 (11)
C180.0582 (19)0.076 (2)0.0694 (19)0.0011 (15)0.0096 (15)0.0120 (16)
C190.066 (2)0.088 (3)0.106 (3)−0.0014 (19)0.033 (2)0.022 (2)
C200.0483 (19)0.062 (2)0.129 (3)−0.0027 (15)0.007 (2)0.002 (2)
C210.057 (2)0.0603 (19)0.097 (3)0.0046 (15)−0.0134 (18)−0.0009 (17)
C220.0535 (17)0.0537 (16)0.0671 (18)0.0019 (13)0.0014 (14)0.0055 (13)
C230.0578 (17)0.0542 (16)0.0509 (15)0.0075 (13)0.0031 (13)0.0143 (12)
C240.063 (2)0.079 (2)0.0688 (19)0.0119 (17)0.0007 (16)0.0176 (16)
C250.066 (2)0.111 (3)0.093 (3)0.026 (2)0.0131 (19)0.038 (2)
C260.100 (3)0.100 (3)0.106 (3)0.048 (3)0.037 (3)0.030 (3)
C270.125 (4)0.081 (3)0.098 (3)0.030 (3)0.020 (3)−0.010 (2)
C280.083 (2)0.074 (2)0.078 (2)0.0142 (19)−0.0018 (18)−0.0088 (18)
C290.0599 (18)0.0490 (15)0.0561 (16)0.0098 (13)−0.0048 (13)0.0054 (12)
C300.0617 (19)0.0603 (17)0.0657 (18)0.0093 (14)−0.0032 (15)0.0055 (14)
C310.069 (2)0.070 (2)0.088 (2)0.0108 (17)−0.0189 (19)0.0005 (18)
C320.095 (3)0.072 (2)0.077 (2)0.016 (2)−0.034 (2)0.0019 (18)
C330.110 (3)0.085 (2)0.064 (2)0.005 (2)−0.012 (2)0.0192 (18)
C340.075 (2)0.083 (2)0.066 (2)−0.0013 (18)−0.0056 (17)0.0210 (17)
C350.0666 (19)0.0454 (15)0.0589 (16)−0.0021 (13)0.0115 (14)0.0070 (12)
C360.109 (3)0.0557 (19)0.084 (2)0.0129 (19)0.014 (2)0.0147 (17)
C370.154 (4)0.055 (2)0.108 (3)0.011 (2)0.031 (3)0.018 (2)
C380.139 (4)0.055 (2)0.091 (3)−0.030 (2)0.041 (3)−0.007 (2)
C390.113 (3)0.073 (3)0.080 (2)−0.031 (2)0.001 (2)−0.0059 (19)
C400.092 (3)0.0554 (18)0.073 (2)−0.0120 (17)−0.0061 (18)0.0047 (15)

Geometric parameters (Å, °)

Sn1—C112.130 (3)C17—C181.376 (4)
Sn1—C172.137 (3)C17—C221.384 (4)
Sn1—C52.144 (2)C18—C191.390 (5)
Sn1—S12.4159 (8)C18—H180.9300
Sn2—C352.129 (3)C19—C201.367 (5)
Sn2—C292.130 (3)C19—H190.9300
Sn2—C232.133 (3)C20—C211.365 (5)
Sn2—S22.4086 (8)C20—H200.9300
S1—C11.818 (3)C21—C221.381 (4)
S2—C41.832 (3)C21—H210.9300
O1—C21.420 (3)C22—H220.9300
O1—H10.8200C23—C281.373 (4)
O2—C31.429 (3)C23—C241.375 (4)
O2—H20.8200C24—C251.382 (5)
C1—C21.518 (4)C24—H240.9300
C1—H1A0.9700C25—C261.341 (6)
C1—H1B0.9700C25—H250.9300
C2—C31.525 (3)C26—C271.362 (6)
C2—H2A0.9800C26—H260.9300
C3—C41.510 (4)C27—C281.382 (5)
C3—H30.9800C27—H270.9300
C4—H4A0.9700C28—H280.9300
C4—H4B0.9700C29—C301.380 (4)
C5—C101.379 (4)C29—C341.386 (4)
C5—C61.385 (4)C30—C311.385 (4)
C6—C71.382 (4)C30—H300.9300
C6—H60.9300C31—C321.350 (5)
C7—C81.363 (5)C31—H310.9300
C7—H70.9300C32—C331.358 (5)
C8—C91.357 (5)C32—H320.9300
C8—H80.9300C33—C341.391 (5)
C9—C101.378 (4)C33—H330.9300
C9—H90.9300C34—H340.9300
C10—H100.9300C35—C401.376 (4)
C11—C161.377 (4)C35—C361.378 (4)
C11—C121.381 (4)C36—C371.393 (5)
C12—C131.384 (5)C36—H360.9300
C12—H120.9300C37—C381.347 (6)
C13—C141.351 (6)C37—H370.9300
C13—H130.9300C38—C391.356 (6)
C14—C151.352 (6)C38—H380.9300
C14—H140.9300C39—C401.382 (4)
C15—C161.377 (5)C39—H390.9300
C15—H150.9300C40—H400.9300
C16—H160.9300
C11—Sn1—C17114.46 (11)C11—C16—H16119.8
C11—Sn1—C5107.59 (10)C15—C16—H16119.8
C17—Sn1—C5104.55 (10)C18—C17—C22118.1 (3)
C11—Sn1—S1108.60 (8)C18—C17—Sn1122.1 (2)
C17—Sn1—S1118.70 (7)C22—C17—Sn1119.7 (2)
C5—Sn1—S1101.47 (7)C17—C18—C19120.7 (3)
C35—Sn2—C29113.96 (11)C17—C18—H18119.7
C35—Sn2—C23113.26 (11)C19—C18—H18119.7
C29—Sn2—C23109.18 (10)C20—C19—C18120.1 (3)
C35—Sn2—S2107.68 (8)C20—C19—H19119.9
C29—Sn2—S2105.19 (8)C18—C19—H19119.9
C23—Sn2—S2107.00 (7)C21—C20—C19119.9 (3)
C1—S1—Sn1101.39 (9)C21—C20—H20120.0
C4—S2—Sn2106.59 (10)C19—C20—H20120.0
C2—O1—H1109.5C20—C21—C22120.0 (3)
C3—O2—H2109.5C20—C21—H21120.0
C2—C1—S1112.91 (18)C22—C21—H21120.0
C2—C1—H1A109.0C21—C22—C17121.2 (3)
S1—C1—H1A109.0C21—C22—H22119.4
C2—C1—H1B109.0C17—C22—H22119.4
S1—C1—H1B109.0C28—C23—C24118.0 (3)
H1A—C1—H1B107.8C28—C23—Sn2120.2 (2)
O1—C2—C1108.2 (2)C24—C23—Sn2121.8 (2)
O1—C2—C3111.3 (2)C23—C24—C25121.2 (3)
C1—C2—C3111.7 (2)C23—C24—H24119.4
O1—C2—H2A108.5C25—C24—H24119.4
C1—C2—H2A108.5C26—C25—C24120.0 (4)
C3—C2—H2A108.5C26—C25—H25120.0
O2—C3—C4110.3 (2)C24—C25—H25120.0
O2—C3—C2106.32 (19)C25—C26—C27120.2 (4)
C4—C3—C2113.8 (2)C25—C26—H26119.9
O2—C3—H3108.7C27—C26—H26119.9
C4—C3—H3108.7C26—C27—C28120.3 (4)
C2—C3—H3108.7C26—C27—H27119.8
C3—C4—S2109.57 (18)C28—C27—H27119.8
C3—C4—H4A109.8C23—C28—C27120.4 (4)
S2—C4—H4A109.8C23—C28—H28119.8
C3—C4—H4B109.8C27—C28—H28119.8
S2—C4—H4B109.8C30—C29—C34118.3 (3)
H4A—C4—H4B108.2C30—C29—Sn2121.2 (2)
C10—C5—C6117.3 (2)C34—C29—Sn2120.5 (2)
C10—C5—Sn1121.06 (19)C29—C30—C31120.6 (3)
C6—C5—Sn1121.6 (2)C29—C30—H30119.7
C7—C6—C5121.1 (3)C31—C30—H30119.7
C7—C6—H6119.5C32—C31—C30120.0 (4)
C5—C6—H6119.5C32—C31—H31120.0
C8—C7—C6120.1 (3)C30—C31—H31120.0
C8—C7—H7119.9C31—C32—C33121.1 (3)
C6—C7—H7119.9C31—C32—H32119.4
C9—C8—C7119.7 (3)C33—C32—H32119.4
C9—C8—H8120.1C32—C33—C34119.6 (4)
C7—C8—H8120.1C32—C33—H33120.2
C8—C9—C10120.4 (3)C34—C33—H33120.2
C8—C9—H9119.8C29—C34—C33120.4 (3)
C10—C9—H9119.8C29—C34—H34119.8
C9—C10—C5121.3 (3)C33—C34—H34119.8
C9—C10—H10119.4C40—C35—C36118.7 (3)
C5—C10—H10119.4C40—C35—Sn2120.7 (2)
C16—C11—C12117.8 (3)C36—C35—Sn2120.5 (3)
C16—C11—Sn1118.1 (2)C35—C36—C37119.6 (4)
C12—C11—Sn1124.1 (2)C35—C36—H36120.2
C11—C12—C13120.7 (3)C37—C36—H36120.2
C11—C12—H12119.7C38—C37—C36120.6 (4)
C13—C12—H12119.7C38—C37—H37119.7
C14—C13—C12120.4 (4)C36—C37—H37119.7
C14—C13—H13119.8C37—C38—C39120.6 (4)
C12—C13—H13119.8C37—C38—H38119.7
C13—C14—C15119.6 (4)C39—C38—H38119.7
C13—C14—H14120.2C38—C39—C40119.6 (4)
C15—C14—H14120.2C38—C39—H39120.2
C14—C15—C16121.1 (4)C40—C39—H39120.2
C14—C15—H15119.5C35—C40—C39120.9 (4)
C16—C15—H15119.5C35—C40—H40119.6
C11—C16—C15120.5 (4)C39—C40—H40119.6
C11—Sn1—S1—C1−39.43 (12)C22—C17—C18—C190.4 (5)
C17—Sn1—S1—C193.60 (12)Sn1—C17—C18—C19−175.9 (3)
C5—Sn1—S1—C1−152.61 (12)C17—C18—C19—C20−0.9 (5)
C35—Sn2—S2—C4−6.64 (13)C18—C19—C20—C210.3 (6)
C29—Sn2—S2—C4115.25 (12)C19—C20—C21—C220.7 (5)
C23—Sn2—S2—C4−128.71 (12)C20—C21—C22—C17−1.2 (5)
Sn1—S1—C1—C2−73.4 (2)C18—C17—C22—C210.6 (4)
S1—C1—C2—O165.3 (2)Sn1—C17—C22—C21177.0 (2)
S1—C1—C2—C3−171.81 (18)C35—Sn2—C23—C28159.8 (3)
O1—C2—C3—O2−70.6 (3)C29—Sn2—C23—C2831.7 (3)
C1—C2—C3—O2168.3 (2)S2—Sn2—C23—C28−81.7 (3)
O1—C2—C3—C451.1 (3)C35—Sn2—C23—C24−21.5 (3)
C1—C2—C3—C4−70.0 (3)C29—Sn2—C23—C24−149.7 (2)
O2—C3—C4—S2−57.5 (2)S2—Sn2—C23—C2497.0 (2)
C2—C3—C4—S2−176.88 (18)C28—C23—C24—C250.2 (5)
Sn2—S2—C4—C3121.26 (17)Sn2—C23—C24—C25−178.5 (3)
C11—Sn1—C5—C10−83.1 (3)C23—C24—C25—C26−0.6 (6)
C17—Sn1—C5—C10154.8 (2)C24—C25—C26—C270.8 (6)
S1—Sn1—C5—C1030.8 (2)C25—C26—C27—C28−0.7 (7)
C11—Sn1—C5—C694.9 (2)C24—C23—C28—C27−0.1 (5)
C17—Sn1—C5—C6−27.2 (2)Sn2—C23—C28—C27178.6 (3)
S1—Sn1—C5—C6−151.2 (2)C26—C27—C28—C230.3 (7)
C10—C5—C6—C70.8 (4)C35—Sn2—C29—C30109.8 (2)
Sn1—C5—C6—C7−177.2 (2)C23—Sn2—C29—C30−122.4 (2)
C5—C6—C7—C8−0.4 (5)S2—Sn2—C29—C30−7.9 (2)
C6—C7—C8—C9−0.3 (5)C35—Sn2—C29—C34−70.8 (3)
C7—C8—C9—C100.5 (6)C23—Sn2—C29—C3457.0 (3)
C8—C9—C10—C50.0 (6)S2—Sn2—C29—C34171.5 (2)
C6—C5—C10—C9−0.6 (5)C34—C29—C30—C311.1 (4)
Sn1—C5—C10—C9177.4 (3)Sn2—C29—C30—C31−179.5 (2)
C17—Sn1—C11—C16136.9 (3)C29—C30—C31—C320.1 (5)
C5—Sn1—C11—C1621.2 (3)C30—C31—C32—C33−1.1 (5)
S1—Sn1—C11—C16−87.9 (3)C31—C32—C33—C340.8 (6)
C17—Sn1—C11—C12−42.2 (3)C30—C29—C34—C33−1.4 (5)
C5—Sn1—C11—C12−157.9 (3)Sn2—C29—C34—C33179.2 (3)
S1—Sn1—C11—C1293.0 (3)C32—C33—C34—C290.5 (6)
C16—C11—C12—C13−1.9 (5)C29—Sn2—C35—C40−177.6 (2)
Sn1—C11—C12—C13177.2 (3)C23—Sn2—C35—C4056.8 (3)
C11—C12—C13—C141.6 (6)S2—Sn2—C35—C40−61.3 (3)
C12—C13—C14—C15−0.5 (7)C29—Sn2—C35—C36−0.6 (3)
C13—C14—C15—C16−0.3 (8)C23—Sn2—C35—C36−126.2 (3)
C12—C11—C16—C151.1 (6)S2—Sn2—C35—C36115.7 (2)
Sn1—C11—C16—C15−178.0 (4)C40—C35—C36—C370.5 (5)
C14—C15—C16—C110.0 (8)Sn2—C35—C36—C37−176.5 (3)
C11—Sn1—C17—C188.9 (3)C35—C36—C37—C38−0.3 (6)
C5—Sn1—C17—C18126.3 (2)C36—C37—C38—C390.0 (7)
S1—Sn1—C17—C18−121.6 (2)C37—C38—C39—C400.0 (6)
C11—Sn1—C17—C22−167.4 (2)C36—C35—C40—C39−0.5 (5)
C5—Sn1—C17—C22−49.9 (2)Sn2—C35—C40—C39176.5 (3)
S1—Sn1—C17—C2262.2 (2)C38—C39—C40—C350.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.952.745 (3)163
O2—H2···C22i0.822.803.493 (3)143

Symmetry codes: (i) −x, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2249).

References

  • Basu Baul, T. (2008). Appl. Organomet. Chem.22, 195–241.
  • Ma, C. & Zhang, Q. (2006). Eur. J. Inorg. Chem. pp. 3244–3254.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography