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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m938.
Published online 2010 July 17. doi:  10.1107/S1600536810027303
PMCID: PMC3007498

Di-n-butyl­bis­(N-cyclo­hexyl-N-ethyl­dithio­carbamato-κ2 S,S′)tin(IV)

Abstract

The SnIV atom in the title compound, [Sn(C4H9)2(C9H16NS2)2], is chelated by the two dithio­carbamate ions in a six-coordinate skew-trapezoidal-bipyramidal geometry. The two butyl groups are disordered over two positions in a 1:1 ratio.

Related literature

For a discussion on six-coordinate, skew-trapezoidal-bipyram­idal diorganotin(IV) bis­(chelates), see: Ng et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m938-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C9H16NS2)2]
  • M r = 637.67
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m938-efi1.jpg
  • a = 10.2809 (4) Å
  • b = 12.5462 (4) Å
  • c = 13.3823 (5) Å
  • α = 103.103 (1)°
  • β = 108.125 (1)°
  • γ = 90.655 (1)°
  • V = 1591.5 (1) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.08 mm−1
  • T = 293 K
  • 0.35 × 0.25 × 0.25 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.703, T max = 0.774
  • 20772 measured reflections
  • 7294 independent reflections
  • 6264 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.125
  • S = 1.03
  • 7294 reflections
  • 316 parameters
  • 56 restraints
  • H-atom parameters constrained
  • Δρmax = 1.65 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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/S1600536810027303/zs2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027303/zs2050Isup2.hkl

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

Acknowledgments

We thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Diorganotin(IV) bis(chelates) generally adopt six-coordinate geometries at tin, a geometry for which the carbon–tin–carbon bond angle is about 135° (Ng et al., 1987). The dithiocarbamate ion is an example of a chelating ligand that imposes such a geometry on the tin atom in diorganotin(IV) compounds. The angle at tin is generally unafffected by the size of the organic group bonded to the metal atom or the steric size of the dithiocarbamate ion. In the title compound (I) (Scheme I, Fig. 1), this angle is 145.4 (2)° and the angle formed by the formally neutral sulfur atom is opened up to 144.13 (3)°.

Experimental

Cabon disulfide (30 mmol) was dropped into an ethanol solution (100 ml) of N-cyclohexyl-N-ethylamine (30 mmol). The solution was kept at 273 K for an hour. Dibutyltin dichloride (15 mmol) dissolved in ethanol (100 ml) was added to give a white precipitate. This was collected and recrystallized from a chloroform/ethanol (1/1) mixture.

Refinement

The carbon atoms of the butyl chains (except for the carbon atoms connected to the tin atom) show large thermal ellipsoids. The disorder could not be refined, and was assumed to be a 1:1 disorder. The 1,2-related carbon-carbon distances were restrained to 1.54±0.01 Å and the 1,3-related ones to 2.51±0.01 Å. The temperature factors of the primed atoms were set to those of the unprimed ones; the anisotropic temperature factors of the disordered atoms were restrained to be nearly isotropic. Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C). The final difference Fourier map had a peak in the vicinity of Sn1.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of (I) at the 50% probability level. The disorder in the butyl chains is not shown.

Crystal data

[Sn(C4H9)2(C9H16NS2)2]Z = 2
Mr = 637.67F(000) = 668
Triclinic, P1Dx = 1.331 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2809 (4) ÅCell parameters from 7406 reflections
b = 12.5462 (4) Åθ = 2.6–26.6°
c = 13.3823 (5) ŵ = 1.08 mm1
α = 103.103 (1)°T = 293 K
β = 108.125 (1)°Block, colorless
γ = 90.655 (1)°0.35 × 0.25 × 0.25 mm
V = 1591.5 (1) Å3

Data collection

Bruker SMART CCD diffractometer7294 independent reflections
Radiation source: fine-focus sealed tube6264 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.703, Tmax = 0.774k = −16→16
20772 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0681P)2 + 0.9862P] where P = (Fo2 + 2Fc2)/3
7294 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 1.65 e Å3
56 restraintsΔρmin = −0.44 e Å3

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

xyzUiso*/UeqOcc. (<1)
Sn10.42811 (2)0.309809 (17)0.227305 (19)0.05422 (10)
S10.36710 (10)0.17378 (7)0.04359 (7)0.0581 (2)
S20.30272 (14)0.09498 (9)0.21583 (9)0.0814 (3)
S30.52115 (11)0.43790 (7)0.13954 (7)0.0623 (2)
S40.54453 (12)0.52211 (7)0.36982 (8)0.0670 (3)
N10.2738 (3)−0.0314 (2)0.0204 (2)0.0509 (6)
N20.6358 (3)0.6359 (2)0.2562 (2)0.0563 (7)
C10.6110 (4)0.2555 (3)0.3212 (3)0.0633 (9)
H1A0.61360.17800.29070.076*0.50
H1B0.68950.29470.31580.076*0.50
H1C0.62390.18350.28200.076*0.50
H1D0.68830.30520.32860.076*0.50
C20.625 (3)0.2722 (19)0.4410 (9)0.065 (3)0.50
H2A0.62110.34930.47230.078*0.50
H2B0.54900.23090.44780.078*0.50
C30.761 (4)0.234 (3)0.5023 (15)0.082 (4)0.50
H3A0.83650.27480.49500.098*0.50
H3B0.76410.15670.47160.098*0.50
C40.775 (7)0.252 (5)0.6223 (16)0.114 (5)0.50
H4A0.86210.23130.66070.171*0.50
H4B0.70260.20810.62960.171*0.50
H4C0.76770.32820.65180.171*0.50
C2'0.613 (3)0.249 (2)0.4344 (9)0.065 (3)0.50
H2'A0.56500.30740.46340.078*0.50
H2'B0.56640.17920.42980.078*0.50
C3'0.761 (4)0.258 (3)0.5103 (14)0.082 (4)0.50
H3'A0.80510.32990.52070.098*0.50
H3'B0.81180.20330.47830.098*0.50
C4'0.762 (7)0.240 (5)0.6199 (18)0.114 (5)0.50
H4'A0.85510.24200.66580.171*0.50
H4'B0.71520.16910.60920.171*0.50
H4'C0.71600.29610.65340.171*0.50
C50.2343 (4)0.3697 (4)0.2261 (4)0.0931 (15)
H5A0.23530.44230.21230.112*0.50
H5B0.16500.32300.16410.112*0.50
H5C0.22680.43860.20420.112*0.50
H5D0.16070.31720.17450.112*0.50
C60.1859 (17)0.379 (3)0.3209 (12)0.121 (4)0.50
H6A0.25090.42680.38460.146*0.50
H6B0.17850.30680.33540.146*0.50
C70.0420 (10)0.4260 (15)0.2955 (10)0.135 (4)0.50
H7A0.04910.49740.28020.162*0.50
H7B−0.02330.37740.23230.162*0.50
C8−0.0064 (13)0.4363 (14)0.3911 (11)0.138 (4)0.50
H8A−0.09220.46890.37780.207*0.50
H8B0.06060.48190.45400.207*0.50
H8C−0.01860.36480.40310.207*0.50
C6'0.2218 (15)0.387 (3)0.3376 (10)0.121 (4)0.50
H6'A0.30500.42750.39040.146*0.50
H6'B0.21340.31590.35360.146*0.50
C7'0.0965 (11)0.4501 (14)0.3491 (13)0.135 (4)0.50
H7'A0.11240.48500.42490.162*0.50
H7'B0.08650.50730.30980.162*0.50
C8'−0.0339 (12)0.3750 (14)0.3060 (13)0.138 (4)0.50
H8'A−0.11010.41730.30980.207*0.50
H8'B−0.02720.32200.34870.207*0.50
H8'C−0.04750.33760.23200.207*0.50
C90.3098 (3)0.0674 (3)0.0880 (3)0.0513 (7)
C100.2289 (4)−0.1252 (3)0.0557 (3)0.0516 (7)
H100.2508−0.10090.13450.062*
C110.0772 (4)−0.1549 (3)0.0106 (4)0.0732 (11)
H11A0.0505−0.1835−0.06730.088*
H11B0.0294−0.08990.02510.088*
C120.0375 (4)−0.2408 (4)0.0621 (5)0.0866 (14)
H12A0.0563−0.20920.13890.104*
H12B−0.0604−0.26200.02990.104*
C130.1141 (4)−0.3410 (3)0.0475 (4)0.0741 (11)
H13A0.0918−0.39070.08690.089*
H13B0.0854−0.3787−0.02870.089*
C140.2659 (4)−0.3117 (3)0.0872 (4)0.0748 (11)
H14A0.3121−0.37720.07100.090*
H14B0.2964−0.28340.16530.090*
C150.3059 (4)−0.2258 (3)0.0350 (4)0.0719 (11)
H15A0.4041−0.20550.06530.086*
H15B0.2835−0.2560−0.04230.086*
C160.2768 (4)−0.0508 (3)−0.0916 (3)0.0628 (9)
H16A0.2857−0.1282−0.11760.075*
H16B0.3576−0.0099−0.09130.075*
C170.1515 (5)−0.0186 (5)−0.1699 (4)0.0913 (14)
H17A0.1607−0.0339−0.24090.137*
H17B0.14320.0585−0.14630.137*
H17C0.0709−0.0599−0.17220.137*
C180.5741 (3)0.5428 (3)0.2578 (3)0.0504 (7)
C190.6807 (4)0.7283 (3)0.3531 (3)0.0683 (10)
H190.65620.70440.41020.082*
C200.6089 (6)0.8281 (4)0.3381 (6)0.118 (2)
H20A0.51040.80960.31400.142*
H20B0.63120.85540.28270.142*
C210.6511 (6)0.9177 (5)0.4444 (6)0.127 (2)
H21A0.60800.98390.43140.153*
H21B0.61870.89350.49710.153*
C220.8011 (6)0.9428 (4)0.4886 (5)0.1024 (17)
H22A0.83150.97740.44080.123*
H22B0.82430.99460.55870.123*
C230.8737 (7)0.8449 (5)0.5006 (6)0.129 (3)
H23A0.85280.81580.55570.154*
H23B0.97190.86480.52480.154*
C240.8344 (5)0.7562 (4)0.3952 (5)0.107 (2)
H24A0.86370.78190.34180.128*
H24B0.88040.69100.40750.128*
C250.6604 (4)0.6495 (3)0.1565 (3)0.0649 (9)
H25A0.66850.72730.15940.078*
H25B0.58090.61600.09480.078*
C260.7854 (5)0.6009 (4)0.1381 (4)0.0879 (13)
H26A0.79460.61420.07270.132*
H26B0.77680.52310.13170.132*
H26C0.86510.63400.19820.132*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.05327 (15)0.04494 (14)0.06159 (16)−0.00580 (9)0.02086 (11)0.00446 (10)
S10.0651 (5)0.0473 (4)0.0591 (5)−0.0115 (4)0.0193 (4)0.0092 (4)
S20.1208 (9)0.0606 (6)0.0617 (6)−0.0339 (6)0.0472 (6)−0.0101 (4)
S30.0791 (6)0.0469 (4)0.0528 (5)−0.0110 (4)0.0154 (4)0.0054 (3)
S40.0905 (7)0.0472 (4)0.0623 (5)−0.0179 (4)0.0334 (5)0.0003 (4)
N10.0617 (16)0.0433 (13)0.0463 (14)−0.0040 (11)0.0205 (12)0.0045 (11)
N20.0621 (16)0.0435 (14)0.0628 (17)−0.0069 (12)0.0213 (13)0.0106 (12)
C10.068 (2)0.059 (2)0.062 (2)0.0050 (17)0.0214 (17)0.0114 (16)
C20.077 (4)0.043 (8)0.071 (3)−0.001 (5)0.024 (3)0.007 (3)
C30.092 (3)0.072 (11)0.079 (4)0.009 (7)0.026 (3)0.015 (5)
C40.135 (10)0.124 (10)0.074 (3)0.007 (8)0.015 (4)0.036 (4)
C2'0.077 (4)0.043 (8)0.071 (3)−0.001 (5)0.024 (3)0.007 (3)
C3'0.092 (3)0.072 (11)0.079 (4)0.009 (7)0.026 (3)0.015 (5)
C4'0.135 (10)0.124 (10)0.074 (3)0.007 (8)0.015 (4)0.036 (4)
C50.061 (2)0.086 (3)0.114 (4)−0.004 (2)0.025 (2)−0.006 (3)
C60.078 (8)0.148 (7)0.139 (7)−0.012 (9)0.059 (6)0.002 (7)
C70.061 (7)0.148 (10)0.171 (13)−0.010 (7)0.044 (7)−0.021 (9)
C80.107 (7)0.180 (12)0.127 (9)0.003 (7)0.056 (7)0.010 (7)
C6'0.078 (8)0.148 (7)0.139 (7)−0.012 (9)0.059 (6)0.002 (7)
C7'0.061 (7)0.148 (10)0.171 (13)−0.010 (7)0.044 (7)−0.021 (9)
C8'0.107 (7)0.180 (12)0.127 (9)0.003 (7)0.056 (7)0.010 (7)
C90.0493 (16)0.0474 (16)0.0535 (17)−0.0075 (13)0.0177 (14)0.0039 (13)
C100.0616 (19)0.0418 (15)0.0483 (16)−0.0053 (13)0.0161 (14)0.0077 (12)
C110.054 (2)0.070 (2)0.113 (3)0.0130 (17)0.033 (2)0.047 (2)
C120.057 (2)0.084 (3)0.136 (4)0.006 (2)0.035 (3)0.058 (3)
C130.076 (3)0.053 (2)0.090 (3)−0.0098 (18)0.018 (2)0.0249 (19)
C140.067 (2)0.060 (2)0.105 (3)0.0150 (18)0.025 (2)0.038 (2)
C150.056 (2)0.062 (2)0.109 (3)0.0129 (17)0.033 (2)0.036 (2)
C160.087 (3)0.0499 (18)0.0525 (19)−0.0011 (17)0.0286 (18)0.0061 (14)
C170.100 (4)0.104 (4)0.061 (2)−0.012 (3)0.013 (2)0.020 (2)
C180.0471 (16)0.0411 (15)0.0593 (18)−0.0013 (12)0.0149 (14)0.0084 (13)
C190.083 (3)0.0443 (17)0.073 (2)−0.0192 (17)0.029 (2)0.0007 (16)
C200.078 (3)0.082 (3)0.143 (5)0.021 (3)0.003 (3)−0.027 (3)
C210.106 (4)0.079 (3)0.162 (6)0.002 (3)0.041 (4)−0.036 (4)
C220.109 (4)0.059 (3)0.120 (4)−0.021 (3)0.033 (3)−0.010 (3)
C230.112 (4)0.080 (3)0.129 (5)0.000 (3)−0.016 (4)−0.027 (3)
C240.078 (3)0.072 (3)0.121 (4)0.011 (2)−0.009 (3)−0.019 (3)
C250.080 (2)0.0527 (19)0.067 (2)−0.0031 (17)0.0260 (19)0.0206 (16)
C260.086 (3)0.091 (3)0.095 (3)−0.006 (2)0.046 (3)0.017 (3)

Geometric parameters (Å, °)

Sn1—C12.128 (4)C6'—C7'1.551 (9)
Sn1—C52.134 (4)C6'—H6'A0.9700
Sn1—S32.5292 (9)C6'—H6'B0.9700
Sn1—S12.5425 (9)C7'—C8'1.504 (9)
Sn1—S42.8927 (9)C7'—H7'A0.9700
Sn1—S22.9257 (10)C7'—H7'B0.9700
S1—C91.744 (3)C8'—H8'A0.9600
S2—C91.691 (3)C8'—H8'B0.9600
S3—C181.743 (3)C8'—H8'C0.9600
S4—C181.693 (4)C10—C111.494 (5)
N1—C91.329 (4)C10—C151.516 (5)
N1—C161.472 (4)C10—H100.9800
N1—C101.482 (4)C11—C121.519 (5)
N2—C181.330 (4)C11—H11A0.9700
N2—C191.474 (5)C11—H11B0.9700
N2—C251.479 (5)C12—C131.499 (6)
C1—C21.529 (8)C12—H12A0.9700
C1—C2'1.530 (9)C12—H12B0.9700
C1—H1A0.9700C13—C141.496 (6)
C1—H1B0.9700C13—H13A0.9700
C1—H1C0.9700C13—H13B0.9700
C1—H1D0.9700C14—C151.526 (5)
C2—C31.527 (9)C14—H14A0.9700
C2—H2A0.9700C14—H14B0.9700
C2—H2B0.9700C15—H15A0.9700
C3—C41.530 (10)C15—H15B0.9700
C3—H3A0.9700C16—C171.512 (6)
C3—H3B0.9700C16—H16A0.9700
C4—H4A0.9600C16—H16B0.9700
C4—H4B0.9600C17—H17A0.9600
C4—H4C0.9600C17—H17B0.9600
C2'—C3'1.526 (9)C17—H17C0.9600
C2'—H2'A0.9700C19—C201.481 (7)
C2'—H2'B0.9700C19—C241.510 (6)
C3'—C4'1.531 (10)C19—H190.9800
C3'—H3'A0.9700C20—C211.534 (8)
C3'—H3'B0.9700C20—H20A0.9700
C4'—H4'A0.9600C20—H20B0.9700
C4'—H4'B0.9600C21—C221.471 (8)
C4'—H4'C0.9600C21—H21A0.9700
C5—C61.484 (9)C21—H21B0.9700
C5—C6'1.505 (9)C22—C231.459 (8)
C5—H5A0.9700C22—H22A0.9700
C5—H5B0.9700C22—H22B0.9700
C5—H5C0.9700C23—C241.521 (7)
C5—H5D0.9700C23—H23A0.9700
C6—C71.567 (9)C23—H23B0.9700
C6—H6A0.9700C24—H24A0.9700
C6—H6B0.9700C24—H24B0.9700
C7—C81.491 (9)C25—C261.493 (6)
C7—H7A0.9700C25—H25A0.9700
C7—H7B0.9700C25—H25B0.9700
C8—H8A0.9600C26—H26A0.9600
C8—H8B0.9600C26—H26B0.9600
C8—H8C0.9600C26—H26C0.9600
C1—Sn1—C5145.4 (2)C8'—C7'—C6'111.6 (10)
C1—Sn1—S3102.1 (1)C8'—C7'—H7'A109.3
C5—Sn1—S3102.5 (2)C6'—C7'—H7'A109.3
C1—Sn1—S1103.7 (1)C8'—C7'—H7'B109.3
C5—Sn1—S1102.1 (1)C6'—C7'—H7'B109.3
S3—Sn1—S185.37 (3)H7'A—C7'—H7'B108.0
C1—Sn1—S483.1 (1)C7'—C8'—H8'A109.5
C5—Sn1—S485.3 (1)C7'—C8'—H8'B109.5
S3—Sn1—S465.63 (3)H8'A—C8'—H8'B109.5
S1—Sn1—S4151.00 (3)C7'—C8'—H8'C109.5
C1—Sn1—S284.4 (1)H8'A—C8'—H8'C109.5
C5—Sn1—S286.2 (2)H8'B—C8'—H8'C109.5
S3—Sn1—S2150.15 (3)N1—C9—S2123.0 (2)
S1—Sn1—S264.83 (3)N1—C9—S1118.8 (2)
S4—Sn1—S2144.13 (3)S2—C9—S1118.26 (18)
C9—S1—Sn194.1 (1)N1—C10—C11113.2 (3)
C9—S2—Sn182.6 (1)N1—C10—C15113.6 (3)
C18—S3—Sn193.3 (1)C11—C10—C15110.6 (3)
C18—S4—Sn182.4 (1)N1—C10—H10106.3
C9—N1—C16121.2 (3)C11—C10—H10106.3
C9—N1—C10120.7 (3)C15—C10—H10106.3
C16—N1—C10118.2 (3)C10—C11—C12109.9 (3)
C18—N2—C19121.2 (3)C10—C11—H11A109.7
C18—N2—C25120.6 (3)C12—C11—H11A109.7
C19—N2—C25118.2 (3)C10—C11—H11B109.7
C2—C1—Sn1114.1 (11)C12—C11—H11B109.7
C2'—C1—Sn1114.9 (11)H11A—C11—H11B108.2
C2—C1—H1A108.7C13—C12—C11112.1 (4)
Sn1—C1—H1A108.7C13—C12—H12A109.2
C2—C1—H1B108.7C11—C12—H12A109.2
C2'—C1—H1B117.4C13—C12—H12B109.2
Sn1—C1—H1B108.7C11—C12—H12B109.2
H1A—C1—H1B107.6H12A—C12—H12B107.9
C2—C1—H1C118.2C14—C13—C12111.3 (3)
C2'—C1—H1C108.5C14—C13—H13A109.4
Sn1—C1—H1C108.5C12—C13—H13A109.4
C2'—C1—H1D108.5C14—C13—H13B109.4
Sn1—C1—H1D108.5C12—C13—H13B109.4
H1C—C1—H1D107.5H13A—C13—H13B108.0
C3—C2—C1110.4 (8)C13—C14—C15111.7 (3)
C3—C2—H2A109.6C13—C14—H14A109.3
C1—C2—H2A109.6C15—C14—H14A109.3
C3—C2—H2B109.6C13—C14—H14B109.3
C1—C2—H2B109.6C15—C14—H14B109.3
H2A—C2—H2B108.1H14A—C14—H14B107.9
C2—C3—C4110.1 (9)C10—C15—C14109.5 (3)
C2—C3—H3A109.6C10—C15—H15A109.8
C4—C3—H3A109.6C14—C15—H15A109.8
C2—C3—H3B109.6C10—C15—H15B109.8
C4—C3—H3B109.6C14—C15—H15B109.8
H3A—C3—H3B108.2H15A—C15—H15B108.2
C3—C4—H4A109.5N1—C16—C17114.3 (3)
C3—C4—H4B109.5N1—C16—H16A108.7
H4A—C4—H4B109.5C17—C16—H16A108.7
C3—C4—H4C109.5N1—C16—H16B108.7
H4A—C4—H4C109.5C17—C16—H16B108.7
H4B—C4—H4C109.5H16A—C16—H16B107.6
C3'—C2'—C1110.7 (8)C16—C17—H17A109.5
C3'—C2'—H2'A109.5C16—C17—H17B109.5
C1—C2'—H2'A109.5H17A—C17—H17B109.5
C3'—C2'—H2'B109.5C16—C17—H17C109.5
C1—C2'—H2'B109.5H17A—C17—H17C109.5
H2'A—C2'—H2'B108.1H17B—C17—H17C109.5
C2'—C3'—C4'110.1 (9)N2—C18—S4122.8 (3)
C2'—C3'—H3'A109.6N2—C18—S3118.6 (3)
C4'—C3'—H3'A109.6S4—C18—S3118.62 (18)
C2'—C3'—H3'B109.6N2—C19—C20113.3 (4)
C4'—C3'—H3'B109.6N2—C19—C24113.1 (4)
H3'A—C3'—H3'B108.1C20—C19—C24110.3 (4)
C3'—C4'—H4'A109.5N2—C19—H19106.5
C3'—C4'—H4'B109.5C20—C19—H19106.5
H4'A—C4'—H4'B109.5C24—C19—H19106.5
C3'—C4'—H4'C109.5C19—C20—C21110.8 (5)
H4'A—C4'—H4'C109.5C19—C20—H20A109.5
H4'B—C4'—H4'C109.5C21—C20—H20A109.5
C6—C5—Sn1121.0 (6)C19—C20—H20B109.5
C6'—C5—Sn1109.5 (5)C21—C20—H20B109.5
C6—C5—H5A107.1H20A—C20—H20B108.1
C6'—C5—H5A105.6C22—C21—C20111.5 (5)
Sn1—C5—H5A107.1C22—C21—H21A109.3
C6—C5—H5B107.1C20—C21—H21A109.3
C6'—C5—H5B120.2C22—C21—H21B109.3
Sn1—C5—H5B107.1C20—C21—H21B109.3
H5A—C5—H5B106.8H21A—C21—H21B108.0
C6—C5—H5C109.8C23—C22—C21112.4 (5)
C6'—C5—H5C109.8C23—C22—H22A109.1
Sn1—C5—H5C109.8C21—C22—H22A109.1
C6'—C5—H5D109.8C23—C22—H22B109.1
Sn1—C5—H5D109.8C21—C22—H22B109.1
H5C—C5—H5D108.2H22A—C22—H22B107.9
C5—C6—C7108.7 (8)C22—C23—C24112.2 (5)
C5—C6—H6A109.9C22—C23—H23A109.2
C7—C6—H6A109.9C24—C23—H23A109.2
C5—C6—H6B109.9C22—C23—H23B109.2
C7—C6—H6B109.9C24—C23—H23B109.2
H6A—C6—H6B108.3H23A—C23—H23B107.9
C8—C7—C6108.9 (8)C19—C24—C23109.9 (5)
C8—C7—H7A109.9C19—C24—H24A109.7
C6—C7—H7A109.9C23—C24—H24A109.7
C8—C7—H7B109.9C19—C24—H24B109.7
C6—C7—H7B109.9C23—C24—H24B109.7
H7A—C7—H7B108.3H24A—C24—H24B108.2
C7—C8—H8A109.5N2—C25—C26114.8 (3)
C7—C8—H8B109.5N2—C25—H25A108.6
H8A—C8—H8B109.5C26—C25—H25A108.6
C7—C8—H8C109.5N2—C25—H25B108.6
H8A—C8—H8C109.5C26—C25—H25B108.6
H8B—C8—H8C109.5H25A—C25—H25B107.5
C5—C6'—C7'112.6 (9)C25—C26—H26A109.5
C5—C6'—H6'A109.1C25—C26—H26B109.5
C7'—C6'—H6'A109.1H26A—C26—H26B109.5
C5—C6'—H6'B109.1C25—C26—H26C109.5
C7'—C6'—H6'B109.1H26A—C26—H26C109.5
H6'A—C6'—H6'B107.8H26B—C26—H26C109.5
C1—Sn1—S1—C974.03 (16)C5—C6—C7—C8−179.4 (18)
C5—Sn1—S1—C9−82.86 (19)C6—C5—C6'—C7'−44 (8)
S3—Sn1—S1—C9175.33 (12)Sn1—C5—C6'—C7'169.4 (12)
S4—Sn1—S1—C9174.78 (12)C5—C6'—C7'—C8'82 (2)
S2—Sn1—S1—C9−2.95 (12)C16—N1—C9—S2177.7 (3)
C1—Sn1—S2—C9−104.97 (16)C10—N1—C9—S2−1.9 (5)
C5—Sn1—S2—C9108.35 (19)C16—N1—C9—S1−2.3 (5)
S3—Sn1—S2—C9−0.38 (16)C10—N1—C9—S1178.0 (2)
S1—Sn1—S2—C93.06 (12)Sn1—S2—C9—N1175.3 (3)
S4—Sn1—S2—C9−175.06 (12)Sn1—S2—C9—S1−4.59 (18)
C1—Sn1—S3—C18−76.12 (15)Sn1—S1—C9—N1−174.7 (3)
C5—Sn1—S3—C1879.37 (17)Sn1—S1—C9—S25.2 (2)
S1—Sn1—S3—C18−179.20 (11)C9—N1—C10—C11105.0 (4)
S4—Sn1—S3—C180.51 (11)C16—N1—C10—C11−74.7 (4)
S2—Sn1—S3—C18−176.08 (12)C9—N1—C10—C15−127.7 (4)
C1—Sn1—S4—C18106.08 (15)C16—N1—C10—C1552.6 (4)
C5—Sn1—S4—C18−106.54 (19)N1—C10—C11—C12−172.5 (4)
S3—Sn1—S4—C18−0.52 (12)C15—C10—C11—C1258.7 (5)
S1—Sn1—S4—C180.08 (15)C10—C11—C12—C13−56.3 (6)
S2—Sn1—S4—C18176.58 (12)C11—C12—C13—C1454.0 (6)
C5—Sn1—C1—C2−8.3 (11)C12—C13—C14—C15−54.1 (6)
S3—Sn1—C1—C2126.2 (10)N1—C10—C15—C14172.6 (3)
S1—Sn1—C1—C2−145.7 (10)C11—C10—C15—C14−58.8 (5)
S4—Sn1—C1—C263.0 (10)C13—C14—C15—C1056.3 (5)
S2—Sn1—C1—C2−83.3 (10)C9—N1—C16—C17−82.1 (4)
C5—Sn1—C1—C2'4.1 (11)C10—N1—C16—C1797.6 (4)
S3—Sn1—C1—C2'138.6 (10)C19—N2—C18—S4−0.9 (5)
S1—Sn1—C1—C2'−133.3 (10)C25—N2—C18—S4179.4 (3)
S4—Sn1—C1—C2'75.4 (10)C19—N2—C18—S3178.9 (3)
S2—Sn1—C1—C2'−70.9 (10)C25—N2—C18—S3−0.8 (5)
C2'—C1—C2—C385 (11)Sn1—S4—C18—N2−179.4 (3)
Sn1—C1—C2—C3−178.4 (15)Sn1—S4—C18—S30.79 (17)
C1—C2—C3—C4179 (2)Sn1—S3—C18—N2179.3 (3)
C2—C1—C2'—C3'−67 (11)Sn1—S3—C18—S4−0.9 (2)
Sn1—C1—C2'—C3'−155.8 (14)C18—N2—C19—C20−116.4 (5)
C1—C2'—C3'—C4'−175 (2)C25—N2—C19—C2063.2 (5)
C1—Sn1—C5—C6−4.2 (17)C18—N2—C19—C24117.0 (4)
S3—Sn1—C5—C6−138.5 (17)C25—N2—C19—C24−63.3 (5)
S1—Sn1—C5—C6133.6 (17)N2—C19—C20—C21175.2 (5)
S4—Sn1—C5—C6−74.8 (17)C24—C19—C20—C21−56.8 (7)
S2—Sn1—C5—C670.3 (17)C19—C20—C21—C2255.0 (8)
C1—Sn1—C5—C6'4.7 (14)C20—C21—C22—C23−53.6 (9)
S3—Sn1—C5—C6'−129.6 (14)C21—C22—C23—C2454.7 (9)
S1—Sn1—C5—C6'142.5 (14)N2—C19—C24—C23−174.8 (5)
S4—Sn1—C5—C6'−65.9 (14)C20—C19—C24—C2357.0 (7)
S2—Sn1—C5—C6'79.3 (14)C22—C23—C24—C19−55.9 (8)
C6'—C5—C6—C7142 (11)C18—N2—C25—C26−82.2 (5)
Sn1—C5—C6—C7179.4 (11)C19—N2—C25—C2698.1 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2050).

References

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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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