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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m314.
Published online 2010 February 20. doi:  10.1107/S1600536810005933
PMCID: PMC2983683

catena-Poly[[tris­(4-fluoro­benz­yl)tin(IV)]{μ-[(N,N-diisopropylcar­bamo­thioyl)sulfanyl]acetato-κ2 O:O′}]

Abstract

In the title compound, [Sn(C7H6F)3(C9H16NO2S2)]n, the Sn atom is coordinated in a slightly distorted, trans-C3SnO2 trigonal-bipyramidal environment. Symmetry-related Sn atoms are bridged by diisopropyl­dithio­carbamoylacetato ligands, forming a one-dimensional polymer along [001].

Related literature

Trialkyl­tin carboxyl­ates are generally carboxyl­ate-bridged polymers; see: Ng et al. (1988 [triangle]). For the direct synthesis of substituted tribenzyl­tin chlorides, see: Sisido et al. (1961 [triangle]). For the synthesis of dithio­carbamoylacetic acids, see: Nachmias (1952 [triangle]). For background to the triorganotin derivatives of dithio­carbamylacetic acids, see: Ng & Kumar Das (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m314-scheme1.jpg

Experimental

Crystal data

  • [Sn(C7H6F)3(C9H16NO2S2)]
  • M r = 680.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m314-efi1.jpg
  • a = 11.2496 (2) Å
  • b = 25.7598 (5) Å
  • c = 11.4216 (2) Å
  • β = 105.427 (1)°
  • V = 3190.58 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.98 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.759, T max = 0.909
  • 21159 measured reflections
  • 7090 independent reflections
  • 5217 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.159
  • S = 1.09
  • 7090 reflections
  • 352 parameters
  • H-atom parameters constrained
  • Δρmax = 1.27 e Å−3
  • Δρmin = −1.18 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]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005933/lh2996sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005933/lh2996Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR and PS338/2009C) for supporting this study.

supplementary crystallographic information

Comment

Part of the one-dimensional polymer of the title compound is shown in Fig. 1.

Experimental

Diisopropyldithiocarbomylacetic acid was synthesized from diisopropylamine, carbon disulfide and chloroacetic acid (Nachmias, 1952). Tri(p-fluorobenzyl)tin chloride was prepared by direct synthesis from p-fluorobenzyl chloride and tin powder in a mixture of toluene and water (Sisido et al., 1961). The triorganotin chloride was hydrolyzed with dilute sodium hydroxide solution to give tri(p-fluorobenzyl)tin hydroxide. The carboxylic acid (0.10 g, 0.43 mmol) and the organotin hydroxide (0.20 g, 0.43 mmol) were heated in ethanol (100 ml) for 1 hour. After filtering the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C). The final difference Fourier map had a peak/hole in the vicinity of Sn1. The magnitudes decreased when the 2θ limit was lowered to 50 °. The Sn<-O bridging bond is somewhat long [Sn1-O1 2.500 (4)Å] and may lead to inefficient packing and hence the reason for the larger than normal voids in the structure [ca. 142 Å3].

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of a portion of polymeric Sn(C7H6F)3(C9H16N2O2S2) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius [symmetry code: (i) x, -y+1/2, z+1/2].

Crystal data

[Sn(C7H6F)3(C9H16NO2S2)]F(000) = 1384
Mr = 680.39Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5664 reflections
a = 11.2496 (2) Åθ = 2.4–28.3°
b = 25.7598 (5) ŵ = 0.98 mm1
c = 11.4216 (2) ÅT = 293 K
β = 105.427 (1)°Block, colorless
V = 3190.58 (10) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer7090 independent reflections
Radiation source: fine-focus sealed tube5217 reflections with I > 2σ(I)
graphiteRint = 0.050
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.759, Tmax = 0.909k = −31→33
21159 measured reflectionsl = −14→14

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0769P)2 + 3.6716P] where P = (Fo2 + 2Fc2)/3
7090 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 1.26 e Å3
0 restraintsΔρmin = −1.18 e Å3

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

xyzUiso*/Ueq
Sn10.66161 (3)0.225810 (13)0.57255 (3)0.03172 (13)
S10.70901 (16)0.42111 (6)0.37053 (14)0.0515 (4)
S20.45463 (17)0.38461 (7)0.35217 (17)0.0594 (4)
F11.1949 (5)0.1403 (3)0.9730 (5)0.131 (2)
F21.0347 (5)0.05335 (19)0.3995 (7)0.123 (2)
F30.1222 (4)0.1519 (2)0.2507 (4)0.0944 (15)
O10.6613 (4)0.26909 (14)0.3765 (3)0.0399 (9)
O20.6790 (3)0.32296 (14)0.2303 (3)0.0395 (8)
N10.5111 (5)0.47966 (18)0.2933 (4)0.0499 (12)
C10.8474 (5)0.2552 (2)0.6297 (5)0.0398 (12)
H1A0.87770.25870.55810.048*
H1B0.84440.28970.66260.048*
C20.9392 (5)0.2243 (2)0.7210 (5)0.0379 (12)
C31.0029 (6)0.1843 (3)0.6852 (6)0.0578 (17)
H30.98810.17600.60330.069*
C41.0897 (7)0.1561 (3)0.7722 (9)0.081 (2)
H41.13290.12910.74850.097*
C51.1106 (6)0.1685 (4)0.8913 (7)0.075 (2)
C61.0492 (6)0.2071 (3)0.9296 (6)0.065 (2)
H61.06400.21481.01180.078*
C70.9642 (5)0.2348 (3)0.8437 (5)0.0491 (15)
H70.92190.26170.86920.059*
C80.6182 (5)0.1582 (2)0.4614 (5)0.0432 (13)
H8A0.56950.13510.49690.052*
H8B0.56760.16850.38210.052*
C90.7277 (5)0.1289 (2)0.4448 (5)0.0434 (13)
C100.7677 (6)0.1362 (2)0.3425 (6)0.0534 (15)
H100.72430.15860.28240.064*
C110.8708 (7)0.1112 (3)0.3262 (8)0.070 (2)
H110.89770.11640.25680.084*
C120.9309 (7)0.0787 (3)0.4153 (10)0.078 (2)
C130.8933 (8)0.0695 (3)0.5164 (8)0.077 (2)
H130.93570.04600.57430.093*
C140.7925 (7)0.0953 (3)0.5329 (6)0.0645 (19)
H140.76760.09010.60340.077*
C150.4941 (5)0.2654 (2)0.5752 (5)0.0413 (13)
H15A0.48390.26590.65690.050*
H15B0.49620.30100.54780.050*
C160.3905 (5)0.2365 (2)0.4919 (5)0.0384 (13)
C170.3326 (6)0.1950 (3)0.5316 (5)0.0514 (15)
H170.35470.18610.61340.062*
C180.2426 (6)0.1667 (3)0.4506 (7)0.0626 (18)
H180.20410.13910.47790.075*
C190.2107 (6)0.1796 (3)0.3309 (6)0.0590 (17)
C200.2654 (6)0.2200 (3)0.2879 (6)0.0579 (18)
H200.24350.22820.20570.070*
C210.3534 (5)0.2481 (3)0.3690 (5)0.0484 (14)
H210.38980.27610.34040.058*
C220.6819 (5)0.3121 (2)0.3390 (5)0.0356 (12)
C230.7238 (6)0.3564 (2)0.4291 (5)0.0434 (13)
H23A0.80990.35070.47090.052*
H23B0.67760.35420.48950.052*
C240.5468 (6)0.4321 (2)0.3331 (5)0.0438 (13)
C250.6014 (7)0.5209 (2)0.2852 (6)0.0654 (19)
H250.68220.50910.33400.078*
C260.5775 (10)0.5729 (3)0.3367 (7)0.104 (4)
H26A0.57540.56860.41960.157*
H26B0.49980.58640.28990.157*
H26C0.64220.59670.33320.157*
C270.6113 (10)0.5271 (3)0.1567 (7)0.092 (3)
H27A0.62930.49400.12640.138*
H27B0.67630.55110.15570.138*
H27C0.53480.54000.10620.138*
C280.3806 (7)0.4941 (3)0.2433 (6)0.0628 (18)
H280.38110.52910.20980.075*
C290.3171 (9)0.4989 (4)0.3436 (8)0.106 (3)
H29A0.23240.50840.30960.159*
H29B0.35740.52510.40010.159*
H29C0.32100.46630.38500.159*
C300.3161 (7)0.4601 (3)0.1383 (7)0.078 (2)
H30A0.36250.45970.07880.117*
H30B0.23500.47360.10220.117*
H30C0.30980.42550.16680.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0307 (2)0.0347 (2)0.02739 (18)−0.00011 (16)0.00355 (13)−0.00373 (14)
S10.0613 (10)0.0373 (8)0.0522 (9)0.0002 (7)0.0088 (7)−0.0025 (7)
S20.0637 (11)0.0510 (10)0.0694 (11)0.0104 (8)0.0281 (9)0.0142 (8)
F10.084 (3)0.184 (6)0.113 (4)0.071 (4)0.003 (3)0.070 (4)
F20.085 (3)0.071 (3)0.226 (7)0.025 (3)0.063 (4)−0.010 (4)
F30.068 (3)0.118 (4)0.085 (3)−0.044 (3)0.001 (2)−0.019 (3)
O10.048 (2)0.036 (2)0.0333 (19)0.0021 (17)0.0058 (16)0.0027 (16)
O20.051 (2)0.039 (2)0.0285 (18)0.0038 (18)0.0116 (16)−0.0028 (15)
N10.072 (4)0.038 (3)0.037 (2)0.011 (3)0.010 (2)0.003 (2)
C10.031 (3)0.050 (3)0.037 (3)−0.006 (3)0.006 (2)0.004 (2)
C20.027 (3)0.050 (3)0.034 (3)−0.002 (2)0.004 (2)0.005 (2)
C30.056 (4)0.063 (4)0.053 (4)0.008 (3)0.013 (3)−0.009 (3)
C40.064 (5)0.068 (5)0.105 (7)0.031 (4)0.012 (4)0.001 (5)
C50.048 (4)0.102 (6)0.066 (5)0.022 (4)−0.001 (3)0.034 (4)
C60.046 (4)0.111 (6)0.035 (3)0.015 (4)0.005 (3)0.014 (4)
C70.035 (3)0.073 (4)0.036 (3)0.006 (3)0.004 (2)−0.006 (3)
C80.043 (3)0.043 (3)0.043 (3)−0.009 (3)0.009 (2)−0.014 (2)
C90.049 (3)0.033 (3)0.045 (3)−0.007 (3)0.008 (3)−0.011 (2)
C100.060 (4)0.040 (3)0.063 (4)0.003 (3)0.021 (3)0.002 (3)
C110.071 (5)0.050 (4)0.101 (6)−0.001 (4)0.044 (4)−0.003 (4)
C120.051 (4)0.039 (4)0.143 (8)0.010 (3)0.021 (5)−0.013 (5)
C130.085 (6)0.041 (4)0.092 (6)0.020 (4)0.001 (5)0.001 (4)
C140.087 (5)0.041 (4)0.062 (4)0.007 (4)0.013 (4)−0.001 (3)
C150.040 (3)0.047 (3)0.036 (3)0.006 (3)0.009 (2)−0.002 (2)
C160.030 (3)0.048 (3)0.037 (3)0.012 (2)0.009 (2)0.004 (2)
C170.049 (4)0.064 (4)0.043 (3)0.003 (3)0.015 (3)0.010 (3)
C180.053 (4)0.068 (5)0.069 (5)−0.013 (4)0.019 (3)0.011 (4)
C190.041 (3)0.070 (5)0.063 (4)−0.011 (3)0.009 (3)−0.007 (4)
C200.040 (3)0.088 (5)0.039 (3)−0.004 (3)−0.003 (3)0.003 (3)
C210.044 (3)0.060 (4)0.037 (3)−0.008 (3)0.004 (3)0.007 (3)
C220.032 (3)0.040 (3)0.032 (3)0.007 (2)0.003 (2)0.000 (2)
C230.052 (3)0.041 (3)0.032 (3)0.007 (3)0.002 (2)−0.002 (2)
C240.065 (4)0.036 (3)0.032 (3)0.003 (3)0.016 (3)−0.003 (2)
C250.093 (5)0.037 (4)0.056 (4)−0.002 (4)0.002 (4)0.004 (3)
C260.179 (10)0.046 (4)0.062 (5)0.012 (5)−0.013 (6)−0.010 (4)
C270.143 (8)0.066 (5)0.076 (5)−0.024 (5)0.044 (6)0.006 (4)
C280.079 (5)0.054 (4)0.054 (4)0.021 (4)0.015 (3)0.009 (3)
C290.133 (8)0.113 (8)0.085 (6)0.074 (7)0.050 (6)0.019 (5)
C300.073 (5)0.088 (6)0.066 (5)0.010 (4)0.004 (4)0.023 (4)

Geometric parameters (Å, °)

Sn1—C82.133 (5)C12—C131.352 (12)
Sn1—C152.151 (5)C13—C141.369 (10)
Sn1—C12.155 (5)C13—H130.9300
Sn1—O2i2.162 (3)C14—H140.9300
Sn1—O12.500 (4)C15—C161.493 (8)
S1—C241.782 (6)C15—H15A0.9700
S1—C231.787 (6)C15—H15B0.9700
S2—C241.655 (6)C16—C211.387 (8)
F1—C51.351 (8)C16—C171.389 (8)
F2—C121.391 (8)C17—C181.383 (9)
F3—C191.361 (7)C17—H170.9300
O1—C221.232 (6)C18—C191.359 (9)
O2—C221.265 (6)C18—H180.9300
O2—Sn1ii2.162 (3)C19—C201.366 (9)
N1—C241.332 (7)C20—C211.368 (8)
N1—C281.474 (8)C20—H200.9300
N1—C251.490 (9)C21—H210.9300
C1—C21.488 (7)C22—C231.525 (7)
C1—H1A0.9700C23—H23A0.9700
C1—H1B0.9700C23—H23B0.9700
C2—C31.378 (8)C25—C271.510 (10)
C2—C71.382 (8)C25—C261.516 (10)
C3—C41.396 (10)C25—H250.9800
C3—H30.9300C26—H26A0.9600
C4—C51.356 (11)C26—H26B0.9600
C4—H40.9300C26—H26C0.9600
C5—C61.349 (11)C27—H27A0.9600
C6—C71.373 (9)C27—H27B0.9600
C6—H60.9300C27—H27C0.9600
C7—H70.9300C28—C301.506 (10)
C8—C91.500 (8)C28—C291.508 (10)
C8—H8A0.9700C28—H280.9800
C8—H8B0.9700C29—H29A0.9600
C9—C101.372 (8)C29—H29B0.9600
C9—C141.380 (9)C29—H29C0.9600
C10—C111.382 (9)C30—H30A0.9600
C10—H100.9300C30—H30B0.9600
C11—C121.351 (11)C30—H30C0.9600
C11—H110.9300
C8—Sn1—C15109.5 (2)Sn1—C15—H15B110.3
C8—Sn1—C1121.1 (2)H15A—C15—H15B108.6
C15—Sn1—C1127.8 (2)C21—C16—C17117.0 (5)
C8—Sn1—O2i88.72 (19)C21—C16—C15120.8 (5)
C15—Sn1—O2i98.59 (18)C17—C16—C15122.1 (5)
C1—Sn1—O2i94.94 (17)C18—C17—C16120.7 (6)
C8—Sn1—O183.41 (18)C18—C17—H17119.6
C15—Sn1—O190.48 (18)C16—C17—H17119.6
C1—Sn1—O183.39 (17)C19—C18—C17119.7 (6)
O2i—Sn1—O1169.58 (13)C19—C18—H18120.2
C24—S1—C23103.0 (3)C17—C18—H18120.2
C22—O1—Sn1139.2 (3)C18—C19—F3120.0 (6)
C22—O2—Sn1ii131.5 (3)C18—C19—C20121.6 (6)
C24—N1—C28123.0 (6)F3—C19—C20118.4 (6)
C24—N1—C25121.9 (6)C21—C20—C19118.3 (6)
C28—N1—C25114.9 (5)C21—C20—H20120.9
C2—C1—Sn1117.4 (4)C19—C20—H20120.9
C2—C1—H1A107.9C20—C21—C16122.7 (6)
Sn1—C1—H1A107.9C20—C21—H21118.6
C2—C1—H1B107.9C16—C21—H21118.6
Sn1—C1—H1B107.9O1—C22—O2125.6 (5)
H1A—C1—H1B107.2O1—C22—C23119.4 (5)
C3—C2—C7117.8 (5)O2—C22—C23114.8 (5)
C3—C2—C1120.7 (5)C22—C23—S1117.6 (4)
C7—C2—C1121.5 (5)C22—C23—H23A107.9
C2—C3—C4119.8 (6)S1—C23—H23A107.9
C2—C3—H3120.1C22—C23—H23B107.9
C4—C3—H3120.1S1—C23—H23B107.9
C5—C4—C3119.6 (7)H23A—C23—H23B107.2
C5—C4—H4120.2N1—C24—S2125.6 (5)
C3—C4—H4120.2N1—C24—S1115.1 (5)
C4—C5—F1118.0 (8)S2—C24—S1119.3 (3)
C4—C5—C6122.1 (6)N1—C25—C27111.3 (6)
F1—C5—C6119.9 (7)N1—C25—C26114.3 (7)
C5—C6—C7118.1 (6)C27—C25—C26110.5 (6)
C5—C6—H6120.9N1—C25—H25106.7
C7—C6—H6120.9C27—C25—H25106.7
C6—C7—C2122.5 (6)C26—C25—H25106.7
C6—C7—H7118.8C25—C26—H26A109.5
C2—C7—H7118.8C25—C26—H26B109.5
C9—C8—Sn1114.9 (4)H26A—C26—H26B109.5
C9—C8—H8A108.5C25—C26—H26C109.5
Sn1—C8—H8A108.5H26A—C26—H26C109.5
C9—C8—H8B108.5H26B—C26—H26C109.5
Sn1—C8—H8B108.5C25—C27—H27A109.5
H8A—C8—H8B107.5C25—C27—H27B109.5
C10—C9—C14118.6 (6)H27A—C27—H27B109.5
C10—C9—C8120.3 (6)C25—C27—H27C109.5
C14—C9—C8121.1 (6)H27A—C27—H27C109.5
C9—C10—C11121.9 (7)H27B—C27—H27C109.5
C9—C10—H10119.1N1—C28—C30112.4 (6)
C11—C10—H10119.1N1—C28—C29110.5 (6)
C12—C11—C10117.2 (7)C30—C28—C29115.4 (8)
C12—C11—H11121.4N1—C28—H28105.9
C10—C11—H11121.4C30—C28—H28105.9
C11—C12—C13123.0 (7)C29—C28—H28105.9
C11—C12—F2117.5 (9)C28—C29—H29A109.5
C13—C12—F2119.5 (8)C28—C29—H29B109.5
C12—C13—C14119.4 (7)H29A—C29—H29B109.5
C12—C13—H13120.3C28—C29—H29C109.5
C14—C13—H13120.3H29A—C29—H29C109.5
C13—C14—C9120.0 (7)H29B—C29—H29C109.5
C13—C14—H14120.0C28—C30—H30A109.5
C9—C14—H14120.0C28—C30—H30B109.5
C16—C15—Sn1107.0 (3)H30A—C30—H30B109.5
C16—C15—H15A110.3C28—C30—H30C109.5
Sn1—C15—H15A110.3H30A—C30—H30C109.5
C16—C15—H15B110.3H30B—C30—H30C109.5
C8—Sn1—O1—C22−176.6 (5)C1—Sn1—C15—C16162.0 (3)
C15—Sn1—O1—C2273.8 (5)O2i—Sn1—C15—C16−94.8 (4)
C1—Sn1—O1—C22−54.2 (5)O1—Sn1—C15—C1680.0 (4)
O2i—Sn1—O1—C22−135.5 (7)Sn1—C15—C16—C21−87.7 (6)
C8—Sn1—C1—C2−70.7 (5)Sn1—C15—C16—C1788.0 (6)
C15—Sn1—C1—C2125.7 (4)C21—C16—C17—C180.2 (9)
O2i—Sn1—C1—C220.8 (4)C15—C16—C17—C18−175.6 (6)
O1—Sn1—C1—C2−148.9 (4)C16—C17—C18—C190.3 (10)
Sn1—C1—C2—C386.3 (6)C17—C18—C19—F3−180.0 (6)
Sn1—C1—C2—C7−94.2 (6)C17—C18—C19—C20−0.1 (11)
C7—C2—C3—C4−0.3 (10)C18—C19—C20—C21−0.6 (11)
C1—C2—C3—C4179.2 (6)F3—C19—C20—C21179.3 (6)
C2—C3—C4—C50.0 (12)C19—C20—C21—C161.2 (10)
C3—C4—C5—F1179.7 (7)C17—C16—C21—C20−1.0 (9)
C3—C4—C5—C60.5 (13)C15—C16—C21—C20174.9 (6)
C4—C5—C6—C7−0.8 (13)Sn1—O1—C22—O2177.0 (3)
F1—C5—C6—C7−179.9 (7)Sn1—O1—C22—C231.7 (8)
C5—C6—C7—C20.5 (11)Sn1ii—O2—C22—O1−8.5 (8)
C3—C2—C7—C60.0 (9)Sn1ii—O2—C22—C23166.9 (3)
C1—C2—C7—C6−179.5 (6)O1—C22—C23—S1−162.0 (4)
C15—Sn1—C8—C9176.0 (4)O2—C22—C23—S122.3 (6)
C1—Sn1—C8—C99.6 (5)C24—S1—C23—C2272.4 (5)
O2i—Sn1—C8—C9−85.4 (4)C28—N1—C24—S2−9.3 (8)
O1—Sn1—C8—C987.8 (4)C25—N1—C24—S2176.7 (4)
Sn1—C8—C9—C10−97.9 (6)C28—N1—C24—S1171.9 (4)
Sn1—C8—C9—C1480.2 (6)C25—N1—C24—S1−2.1 (7)
C14—C9—C10—C11−0.4 (10)C23—S1—C24—N1176.2 (4)
C8—C9—C10—C11177.7 (6)C23—S1—C24—S2−2.6 (4)
C9—C10—C11—C120.3 (11)C24—N1—C25—C27100.4 (7)
C10—C11—C12—C131.0 (12)C28—N1—C25—C27−74.0 (8)
C10—C11—C12—F2180.0 (6)C24—N1—C25—C26−133.4 (6)
C11—C12—C13—C14−2.2 (13)C28—N1—C25—C2652.1 (7)
F2—C12—C13—C14178.8 (7)C24—N1—C28—C30−56.2 (8)
C12—C13—C14—C92.1 (12)C25—N1—C28—C30118.2 (7)
C10—C9—C14—C13−0.8 (10)C24—N1—C28—C2974.3 (8)
C8—C9—C14—C13−178.9 (6)C25—N1—C28—C29−111.4 (7)
C8—Sn1—C15—C16−3.1 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2996).

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