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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m87.
Published online 2007 December 6. doi:  10.1107/S1600536807064288
PMCID: PMC2914963

Di-tert-butyl­chlorido(pyrrolidine-1-dithio­carboxyl­ato-κ2 S,S′)tin(IV)

Abstract

The title compound, [Sn(C4H9)2(C5H8NS2)Cl], contains two mol­ecules in the asymmetric unit, with similar conformations. In both mol­ecules, the Sn atom adopts a distorted trigonal-bipyramidal geometry arising from two C atoms, one Cl atom and two S atoms from the bidentate dithio­carbamate ligand, with one Sn—S bond much longer than the other. One C atom of the pyrrolidine ring is disordered equally over two sites.

Related literature

For related structures, see: Ng et al. (1989 [triangle]); Furue et al. (1970 [triangle]); Hall & Tiekink (1995 [triangle]); Jung & Sohn (1988 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00m87-scheme1.jpg

Experimental

Crystal data

  • [Sn(C4H9)2(C5H8NS2)Cl]
  • M r = 414.61
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m87-efi1.jpg
  • a = 12.399 (3) Å
  • b = 25.159 (5) Å
  • c = 12.104 (2) Å
  • β = 97.764 (3)°
  • V = 3741.2 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.72 mm−1
  • T = 293 (2) K
  • 0.47 × 0.34 × 0.29 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Siemens, 1996 [triangle]) T min = 0.500, T max = 0.636
  • 24292 measured reflections
  • 9079 independent reflections
  • 4691 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.118
  • S = 1.00
  • 9079 reflections
  • 325 parameters
  • H-atom parameters constrained
  • Δρmax = 0.99 e Å−3
  • Δρmin = −0.46 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, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064288/xu2363sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064288/xu2363Isup2.hkl

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

Acknowledgments

We acknowledge the financial support of the Natural Science Foundation of China.

supplementary crystallographic information

Comment

Chlorodialkyltin(IV) derivatives of monobasic chelating ligands generally exist as six-coordinate compounds arising from chloride-ion bridging (Ng et al., 1989). An example of such a compound is chloride-bridged, dimeric chlorodimethyl(N,N-dimethyldithiocarbamato)tin, whose crystal structure has been known for a long time (Furue et al., 1970). Replacing the methyl group on tin by the phenyl group interferes with the bridging, as noted in chlorobis(N-cyclohexyl-N-ethyldithiocarbamato)diphenyltin (Hall & Tiekink, 1995).

The sterically bulky t-butyl group in the title compound, (I), is also expected to disrupt bridging, and a molecular species results (Fig. 1). There are two molecules in the asymmetric unit, with similar geometries. In both cases, the tin(IV) atom adopts a distorted C2ClS2Sn-trigonal bipyramidal geometry (Table 1). The formally double-bonded sulfur atom occupies one of the apical sites and the chloride ion the other in the axially most-electronegative configuration. Othwerwise, the geometrical parameters for (I) may be regarded as normal (Allen et al., 1987) and are similar to those found in the other R2ClSnS2CNR'2 mentioned above.

Experimental

The title compound was synthesized by the method described in the literature (Jung & Sohn, 1988). Recrystallization from a 1:1 v/v mixture of dichloromethane-hexane yielded colourless blocks of (I). M.P. 439 K. Analysis. Calc. for C26H52N2S4ClSn2: C 37.66, H 6.32; N 3.38%. Found: C 34.43, H 6.18, N 3.52%.

Refinement

Some of the carbon atoms of the t-butyl groups show significant anisotropic displacements. Attempts to model this as disorder over two or more sites were not successful. Atom C4 is disordered over two positions in a 0.50 (3):0.50 (3) ratio.

The hydrogen atoms were geometrically placed (C–H = 0.96–0.97 Å), and refined as riding with U(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.

Figures

Fig. 1.
The molecular structure of the Sn2 molecule in (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms). The long Sn—S contact is shown as a double dashed line.

Crystal data

[Sn(C4H9)2(C5H8NS2)Cl]F000 = 1680
Mr = 414.61Dx = 1.472 Mg m3
Monoclinic, P21/cMelting point: 439 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 12.399 (3) ÅCell parameters from 4903 reflections
b = 25.159 (5) Åθ = 2.3–23.7º
c = 12.104 (2) ŵ = 1.72 mm1
β = 97.764 (3)ºT = 293 (2) K
V = 3741.2 (13) Å3Block, colourless
Z = 80.47 × 0.34 × 0.29 mm

Data collection

Siemens SMART CCD diffractometer9079 independent reflections
Radiation source: fine-focus sealed tube4691 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 293(2) Kθmax = 28.4º
ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Siemens, 1996)h = −15→16
Tmin = 0.500, Tmax = 0.636k = −33→33
24292 measured reflectionsl = −16→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.118  w = 1/[σ2(Fo2) + (0.0411P)2 + 2.9577P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
9079 reflectionsΔρmax = 0.99 e Å3
325 parametersΔρmin = −0.46 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/UeqOcc. (<1)
Sn10.19927 (3)0.129544 (14)0.43807 (3)0.05039 (12)
C10.4091 (4)0.1000 (2)0.3436 (4)0.0530 (13)
C20.5521 (4)0.0316 (2)0.3531 (5)0.0656 (16)
H2A0.50500.00130.33310.079*
H2B0.57180.03230.43340.079*
C30.6511 (6)0.0297 (3)0.2947 (7)0.122 (3)
H3A0.71390.01830.34590.147*
H3B0.64020.00490.23290.147*
C4A0.6687 (15)0.0843 (9)0.253 (2)0.084 (7)*0.50 (3)
H4A10.71600.10440.30880.101*0.50 (3)
H4A20.70160.08300.18530.101*0.50 (3)
C4B0.6406 (14)0.0636 (8)0.2067 (18)0.076 (6)*0.50 (3)
H4B10.61140.04500.13890.091*0.50 (3)
H4B20.71080.07840.19660.091*0.50 (3)
C50.5605 (4)0.1089 (2)0.2330 (5)0.0652 (15)
H5A0.52720.10310.15670.078*
H5B0.56460.14680.24760.078*
C60.2373 (5)0.2007 (2)0.5401 (5)0.0728 (17)
C70.2331 (6)0.2489 (3)0.4688 (7)0.107 (3)
H7A0.16290.25130.42450.161*
H7B0.28840.24660.42060.161*
H7C0.24520.27990.51500.161*
C80.1499 (8)0.2060 (3)0.6171 (7)0.148 (4)
H8A0.14940.17460.66210.222*
H8B0.07990.21030.57310.222*
H8C0.16530.23640.66440.222*
C90.3471 (7)0.1940 (3)0.6056 (8)0.166 (5)
H9A0.34740.16290.65150.249*
H9B0.36410.22460.65200.249*
H9C0.40040.19010.55560.249*
C100.0631 (5)0.1179 (3)0.3061 (5)0.0694 (17)
C110.0560 (7)0.1630 (3)0.2258 (7)0.138 (4)
H11A0.12370.16640.19620.207*
H11B0.04140.19530.26340.207*
H11C−0.00170.15650.16610.207*
C120.0851 (9)0.0686 (3)0.2428 (9)0.189 (6)
H12A0.15170.07290.21150.284*
H12B0.02620.06270.18400.284*
H12C0.09140.03870.29250.284*
C13−0.0373 (7)0.1138 (6)0.3534 (8)0.251 (8)
H13A−0.03220.08480.40550.377*
H13B−0.09640.10740.29510.377*
H13C−0.05000.14620.39120.377*
N10.4993 (3)0.08164 (16)0.3120 (4)0.0540 (11)
S10.34854 (12)0.06438 (6)0.44053 (13)0.0652 (4)
S20.34882 (13)0.15709 (6)0.29081 (14)0.0707 (4)
Cl10.13750 (14)0.07141 (7)0.58121 (14)0.0856 (5)
Sn20.76534 (3)0.139079 (15)0.85114 (3)0.05640 (13)
C140.7473 (4)0.0294 (2)0.9603 (4)0.0560 (14)
C150.8512 (5)−0.0358 (2)1.0835 (5)0.0699 (16)
H15A0.8583−0.01771.15480.084*
H15B0.9170−0.03031.04980.084*
C160.8299 (6)−0.0941 (3)1.0971 (7)0.098 (2)
H16A0.8627−0.11481.04290.117*
H16B0.8592−0.10601.17130.117*
C170.7135 (6)−0.0995 (3)1.0794 (7)0.109 (3)
H17A0.6839−0.09421.14870.130*
H17B0.6933−0.13481.05160.130*
C180.6694 (5)−0.0577 (2)0.9943 (5)0.0731 (17)
H18A0.6606−0.07190.91910.088*
H18B0.6002−0.04371.01010.088*
C190.6519 (5)0.1953 (2)0.9113 (5)0.0738 (17)
C200.5356 (6)0.1769 (4)0.8820 (9)0.170 (5)
H20A0.51860.17390.80250.255*
H20B0.48760.20230.90920.255*
H20C0.52670.14290.91570.255*
C210.6793 (8)0.1989 (3)1.0358 (6)0.128 (3)
H21A0.75300.21101.05440.192*
H21B0.67180.16441.06810.192*
H21C0.63080.22341.06450.192*
C220.6713 (8)0.2495 (3)0.8622 (7)0.133 (3)
H22A0.65600.24780.78240.199*
H22B0.74580.25970.88350.199*
H22C0.62420.27520.88970.199*
C230.7730 (6)0.1232 (3)0.6746 (5)0.0767 (18)
C240.6554 (7)0.1218 (4)0.6157 (6)0.129 (3)
H24A0.61630.09390.64680.194*
H24B0.65560.11550.53750.194*
H24C0.62080.15530.62580.194*
C250.8356 (7)0.1679 (3)0.6291 (7)0.130 (3)
H25A0.79910.20100.63770.194*
H25B0.83970.16180.55150.194*
H25C0.90780.16940.66930.194*
C260.8287 (8)0.0714 (3)0.6631 (7)0.140 (4)
H26A0.78910.04360.69400.210*
H26B0.90130.07300.70210.210*
H26C0.83150.06430.58560.210*
N20.7552 (3)−0.01685 (17)1.0098 (4)0.0564 (11)
S30.85602 (11)0.07357 (6)0.98437 (14)0.0682 (4)
S40.63452 (12)0.04916 (7)0.87493 (14)0.0756 (5)
Cl20.92997 (15)0.19225 (7)0.89949 (19)0.1153 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.0460 (2)0.0545 (2)0.0514 (2)0.00284 (17)0.00948 (16)0.00291 (18)
C10.045 (3)0.055 (3)0.062 (4)−0.001 (2)0.017 (3)−0.005 (3)
C20.061 (4)0.067 (4)0.070 (4)0.017 (3)0.013 (3)0.005 (3)
C30.099 (6)0.154 (8)0.127 (7)0.070 (6)0.065 (5)0.029 (6)
C50.063 (4)0.075 (4)0.062 (4)0.003 (3)0.025 (3)0.002 (3)
C60.083 (5)0.059 (4)0.075 (4)0.004 (3)0.007 (4)−0.014 (3)
C70.124 (7)0.066 (4)0.131 (7)−0.003 (4)0.016 (5)−0.013 (5)
C80.219 (11)0.107 (6)0.140 (8)−0.004 (7)0.104 (8)−0.043 (6)
C90.147 (8)0.129 (7)0.192 (10)0.018 (6)−0.091 (8)−0.068 (7)
C100.059 (4)0.081 (4)0.065 (4)−0.011 (3)−0.006 (3)0.007 (3)
C110.130 (7)0.132 (7)0.132 (7)−0.007 (6)−0.056 (6)0.028 (6)
C120.200 (11)0.130 (7)0.198 (11)0.039 (7)−0.118 (9)−0.075 (8)
C130.050 (5)0.57 (3)0.123 (8)−0.049 (10)−0.010 (5)0.051 (12)
N10.050 (3)0.058 (3)0.056 (3)0.007 (2)0.016 (2)0.001 (2)
S10.0643 (10)0.0593 (9)0.0771 (11)0.0141 (7)0.0283 (8)0.0201 (8)
S20.0653 (10)0.0629 (9)0.0900 (12)0.0163 (7)0.0326 (9)0.0275 (8)
Cl10.0828 (12)0.0949 (12)0.0859 (12)0.0063 (9)0.0361 (9)0.0295 (10)
Sn20.0486 (2)0.0586 (2)0.0612 (3)−0.00115 (17)0.00451 (18)0.00429 (19)
C140.048 (3)0.068 (4)0.052 (3)−0.002 (3)0.009 (3)0.000 (3)
C150.068 (4)0.064 (4)0.078 (4)0.003 (3)0.011 (3)0.012 (3)
C160.105 (6)0.075 (5)0.116 (6)0.009 (4)0.024 (5)0.023 (4)
C170.105 (6)0.055 (4)0.171 (8)−0.008 (4)0.040 (6)0.014 (5)
C180.067 (4)0.066 (4)0.089 (5)−0.024 (3)0.017 (3)−0.009 (4)
C190.083 (5)0.068 (4)0.072 (5)0.013 (3)0.016 (3)−0.008 (3)
C200.073 (6)0.157 (9)0.279 (14)0.034 (6)0.022 (7)−0.076 (9)
C210.226 (10)0.084 (5)0.081 (6)0.014 (6)0.049 (6)−0.005 (4)
C220.204 (10)0.085 (5)0.115 (7)0.061 (6)0.046 (6)0.025 (5)
C230.092 (5)0.075 (4)0.068 (4)0.005 (4)0.029 (4)0.003 (3)
C240.147 (8)0.175 (8)0.061 (5)−0.006 (7)−0.002 (5)−0.008 (5)
C250.174 (9)0.121 (7)0.109 (7)−0.010 (6)0.077 (6)0.022 (5)
C260.212 (10)0.089 (6)0.138 (8)0.040 (6)0.092 (7)−0.001 (5)
N20.053 (3)0.057 (3)0.060 (3)−0.003 (2)0.009 (2)0.002 (2)
S30.0478 (8)0.0676 (9)0.0841 (11)−0.0126 (7)−0.0103 (8)0.0192 (8)
S40.0508 (9)0.0848 (11)0.0855 (12)−0.0142 (8)−0.0108 (8)0.0149 (9)
Cl20.0780 (12)0.0915 (12)0.167 (2)−0.0381 (10)−0.0170 (12)0.0282 (13)

Geometric parameters (Å, °)

Sn1—S12.4696 (15)C13—H13B0.9600
Sn1—S22.8264 (16)C13—H13C0.9600
Sn1—C62.190 (6)Sn2—S32.4681 (15)
Sn1—C102.182 (5)Sn2—S42.8209 (16)
Sn1—Cl12.4669 (16)Sn2—Cl22.4447 (17)
C1—N11.313 (6)Sn2—C192.187 (6)
C1—S21.704 (5)Sn2—C232.189 (6)
C1—S11.726 (5)C14—N21.306 (6)
C2—N11.475 (6)C14—S41.697 (5)
C2—C31.498 (8)C14—S31.741 (5)
C2—H2A0.9700C15—N21.468 (7)
C2—H2B0.9700C15—C161.502 (8)
C3—C4B1.357 (14)C15—H15A0.9700
C3—C4A1.487 (18)C15—H15B0.9700
C3—H3A0.9700C16—C171.437 (9)
C3—H3B0.9700C16—H16A0.9700
C4A—C51.467 (14)C16—H16B0.9700
C4A—H4A10.9700C17—C181.521 (9)
C4A—H4A20.9700C17—H17A0.9700
C4B—C51.573 (16)C17—H17B0.9700
C4B—H4B10.9700C18—N21.473 (6)
C4B—H4B20.9700C18—H18A0.9700
C5—N11.469 (6)C18—H18B0.9700
C5—H5A0.9700C19—C211.502 (9)
C5—H5B0.9700C19—C201.510 (10)
C6—C71.484 (8)C19—C221.520 (9)
C6—C91.490 (9)C20—H20A0.9600
C6—C81.528 (9)C20—H20B0.9600
C7—H7A0.9600C20—H20C0.9600
C7—H7B0.9600C21—H21A0.9600
C7—H7C0.9600C21—H21B0.9600
C8—H8A0.9600C21—H21C0.9600
C8—H8B0.9600C22—H22A0.9600
C8—H8C0.9600C22—H22B0.9600
C9—H9A0.9600C22—H22C0.9600
C9—H9B0.9600C23—C261.490 (9)
C9—H9C0.9600C23—C251.512 (9)
C10—C131.443 (10)C23—C241.534 (10)
C10—C111.489 (9)C24—H24A0.9600
C10—C121.502 (10)C24—H24B0.9600
C11—H11A0.9600C24—H24C0.9600
C11—H11B0.9600C25—H25A0.9600
C11—H11C0.9600C25—H25B0.9600
C12—H12A0.9600C25—H25C0.9600
C12—H12B0.9600C26—H26A0.9600
C12—H12C0.9600C26—H26B0.9600
C13—H13A0.9600C26—H26C0.9600
C10—Sn1—C6127.5 (2)H13A—C13—H13C109.5
C10—Sn1—Cl198.75 (17)H13B—C13—H13C109.5
C6—Sn1—Cl198.76 (18)C1—N1—C5124.1 (4)
C10—Sn1—S1115.12 (18)C1—N1—C2123.9 (4)
C6—Sn1—S1115.61 (17)C5—N1—C2112.0 (4)
Cl1—Sn1—S184.33 (5)C1—S1—Sn192.39 (18)
C10—Sn1—S294.56 (17)C1—S2—Sn181.30 (18)
C6—Sn1—S292.62 (18)C19—Sn2—C23123.9 (2)
Cl1—Sn1—S2151.72 (5)C19—Sn2—Cl296.91 (18)
S1—Sn1—S267.41 (5)C23—Sn2—Cl2100.86 (19)
N1—C1—S2122.3 (4)C19—Sn2—S3118.09 (18)
N1—C1—S1118.8 (4)C23—Sn2—S3116.12 (18)
S2—C1—S1118.9 (3)Cl2—Sn2—S385.24 (6)
N1—C2—C3102.8 (5)C19—Sn2—S494.58 (18)
N1—C2—H2A111.2C23—Sn2—S493.15 (18)
C3—C2—H2A111.2Cl2—Sn2—S4152.55 (6)
N1—C2—H2B111.2S3—Sn2—S467.37 (5)
C3—C2—H2B111.2N2—C14—S4123.0 (4)
H2A—C2—H2B109.1N2—C14—S3118.9 (4)
C4B—C3—C4A32.8 (7)S4—C14—S3118.1 (3)
C4B—C3—C2110.7 (8)N2—C15—C16104.1 (5)
C4A—C3—C2107.2 (8)N2—C15—H15A110.9
C4B—C3—H3A132.1C16—C15—H15A110.9
C4A—C3—H3A110.3N2—C15—H15B110.9
C2—C3—H3A110.3C16—C15—H15B110.9
C4B—C3—H3B79.0H15A—C15—H15B108.9
C4A—C3—H3B110.3C17—C16—C15105.4 (6)
C2—C3—H3B110.3C17—C16—H16A110.7
H3A—C3—H3B108.5C15—C16—H16A110.7
C5—C4A—C3105.9 (12)C17—C16—H16B110.7
C5—C4A—H4A1110.6C15—C16—H16B110.7
C3—C4A—H4A1110.6H16A—C16—H16B108.8
C5—C4A—H4A2110.6C16—C17—C18107.3 (6)
C3—C4A—H4A2110.6C16—C17—H17A110.3
H4A1—C4A—H4A2108.7C18—C17—H17A110.3
C3—C4B—C5107.0 (11)C16—C17—H17B110.3
C3—C4B—H4B1110.3C18—C17—H17B110.3
C5—C4B—H4B1110.3H17A—C17—H17B108.5
C3—C4B—H4B2110.3N2—C18—C17102.1 (5)
C5—C4B—H4B2110.3N2—C18—H18A111.4
H4B1—C4B—H4B2108.6C17—C18—H18A111.3
C4A—C5—N1103.5 (7)N2—C18—H18B111.3
C4A—C5—C4B30.8 (7)C17—C18—H18B111.3
N1—C5—C4B100.9 (6)H18A—C18—H18B109.2
C4A—C5—H5A111.1C21—C19—C20109.5 (7)
N1—C5—H5A111.1C21—C19—C22108.2 (6)
C4B—C5—H5A84.1C20—C19—C22112.3 (7)
C4A—C5—H5B111.1C21—C19—Sn2107.7 (5)
N1—C5—H5B111.1C20—C19—Sn2111.2 (5)
C4B—C5—H5B137.0C22—C19—Sn2107.9 (5)
H5A—C5—H5B109.0C19—C20—H20A109.5
C7—C6—C9111.1 (7)C19—C20—H20B109.5
C7—C6—C8108.2 (6)H20A—C20—H20B109.5
C9—C6—C8110.9 (7)C19—C20—H20C109.5
C7—C6—Sn1110.6 (4)H20A—C20—H20C109.5
C9—C6—Sn1108.6 (4)H20B—C20—H20C109.5
C8—C6—Sn1107.4 (5)C19—C21—H21A109.5
C6—C7—H7A109.5C19—C21—H21B109.5
C6—C7—H7B109.5H21A—C21—H21B109.5
H7A—C7—H7B109.5C19—C21—H21C109.5
C6—C7—H7C109.5H21A—C21—H21C109.5
H7A—C7—H7C109.5H21B—C21—H21C109.5
H7B—C7—H7C109.5C19—C22—H22A109.5
C6—C8—H8A109.5C19—C22—H22B109.5
C6—C8—H8B109.5H22A—C22—H22B109.5
H8A—C8—H8B109.5C19—C22—H22C109.5
C6—C8—H8C109.5H22A—C22—H22C109.5
H8A—C8—H8C109.5H22B—C22—H22C109.5
H8B—C8—H8C109.5C26—C23—C25110.5 (6)
C6—C9—H9A109.5C26—C23—C24111.1 (7)
C6—C9—H9B109.5C25—C23—C24110.5 (6)
H9A—C9—H9B109.5C26—C23—Sn2109.4 (5)
C6—C9—H9C109.5C25—C23—Sn2108.2 (5)
H9A—C9—H9C109.5C24—C23—Sn2107.1 (4)
H9B—C9—H9C109.5C23—C24—H24A109.5
C13—C10—C11109.7 (8)C23—C24—H24B109.5
C13—C10—C12111.6 (8)H24A—C24—H24B109.5
C11—C10—C12107.2 (7)C23—C24—H24C109.5
C13—C10—Sn1110.0 (5)H24A—C24—H24C109.5
C11—C10—Sn1110.3 (4)H24B—C24—H24C109.5
C12—C10—Sn1107.9 (4)C23—C25—H25A109.5
C10—C11—H11A109.5C23—C25—H25B109.5
C10—C11—H11B109.5H25A—C25—H25B109.5
H11A—C11—H11B109.5C23—C25—H25C109.5
C10—C11—H11C109.5H25A—C25—H25C109.5
H11A—C11—H11C109.5H25B—C25—H25C109.5
H11B—C11—H11C109.5C23—C26—H26A109.5
C10—C12—H12A109.5C23—C26—H26B109.5
C10—C12—H12B109.5H26A—C26—H26B109.5
H12A—C12—H12B109.5C23—C26—H26C109.5
C10—C12—H12C109.5H26A—C26—H26C109.5
H12A—C12—H12C109.5H26B—C26—H26C109.5
H12B—C12—H12C109.5C14—N2—C15125.0 (4)
C10—C13—H13A109.5C14—N2—C18123.7 (5)
C10—C13—H13B109.5C15—N2—C18111.3 (4)
H13A—C13—H13B109.5C14—S3—Sn292.45 (19)
C10—C13—H13C109.5C14—S4—Sn281.93 (19)
N1—C2—C3—C4B−17.3 (14)C10—Sn1—S2—C1−115.9 (2)
N1—C2—C3—C4A17.2 (13)C6—Sn1—S2—C1116.2 (2)
C4B—C3—C4A—C572.6 (19)Cl1—Sn1—S2—C12.2 (2)
C2—C3—C4A—C5−29.0 (19)S1—Sn1—S2—C1−0.57 (18)
C4A—C3—C4B—C5−63.5 (17)N2—C15—C16—C17−26.0 (8)
C2—C3—C4B—C526.4 (19)C15—C16—C17—C1832.6 (8)
C3—C4A—C5—N128.0 (18)C16—C17—C18—N2−25.7 (7)
C3—C4A—C5—C4B−60.7 (17)C23—Sn2—C19—C21−174.5 (5)
C3—C4B—C5—C4A74.0 (19)Cl2—Sn2—C19—C21−66.4 (5)
C3—C4B—C5—N1−24.2 (17)S3—Sn2—C19—C2121.9 (5)
C10—Sn1—C6—C7−48.4 (6)S4—Sn2—C19—C2188.6 (5)
Cl1—Sn1—C6—C7−156.6 (5)C23—Sn2—C19—C2065.6 (7)
S1—Sn1—C6—C7115.6 (5)Cl2—Sn2—C19—C20173.7 (6)
S2—Sn1—C6—C749.4 (5)S3—Sn2—C19—C20−98.1 (6)
C10—Sn1—C6—C9−170.5 (6)S4—Sn2—C19—C20−31.3 (6)
Cl1—Sn1—C6—C981.3 (6)C23—Sn2—C19—C22−57.9 (6)
S1—Sn1—C6—C9−6.6 (6)Cl2—Sn2—C19—C2250.1 (5)
S2—Sn1—C6—C9−72.7 (6)S3—Sn2—C19—C22138.4 (4)
C10—Sn1—C6—C869.4 (6)S4—Sn2—C19—C22−154.8 (5)
Cl1—Sn1—C6—C8−38.7 (5)C19—Sn2—C23—C26−160.5 (5)
S1—Sn1—C6—C8−126.6 (5)Cl2—Sn2—C23—C2693.5 (5)
S2—Sn1—C6—C8167.2 (5)S3—Sn2—C23—C263.5 (6)
C6—Sn1—C10—C13−71.1 (8)S4—Sn2—C23—C26−62.8 (5)
Cl1—Sn1—C10—C1337.1 (8)C19—Sn2—C23—C2579.1 (6)
S1—Sn1—C10—C13124.9 (8)Cl2—Sn2—C23—C25−26.9 (5)
S2—Sn1—C10—C13−167.9 (8)S3—Sn2—C23—C25−116.9 (5)
C6—Sn1—C10—C1150.0 (6)S4—Sn2—C23—C25176.8 (5)
Cl1—Sn1—C10—C11158.2 (5)C19—Sn2—C23—C24−40.0 (6)
S1—Sn1—C10—C11−113.9 (5)Cl2—Sn2—C23—C24−146.0 (5)
S2—Sn1—C10—C11−46.8 (5)S3—Sn2—C23—C24124.0 (4)
C6—Sn1—C10—C12166.9 (6)S4—Sn2—C23—C2457.7 (5)
Cl1—Sn1—C10—C12−84.9 (6)S4—C14—N2—C15179.5 (4)
S1—Sn1—C10—C122.9 (6)S3—C14—N2—C15−1.7 (8)
S2—Sn1—C10—C1270.1 (6)S4—C14—N2—C182.3 (8)
S2—C1—N1—C52.9 (7)S3—C14—N2—C18−178.9 (4)
S1—C1—N1—C5−178.0 (4)C16—C15—N2—C14−167.6 (5)
S2—C1—N1—C2−178.1 (4)C16—C15—N2—C1810.0 (7)
S1—C1—N1—C21.0 (7)C17—C18—N2—C14−173.5 (6)
C4A—C5—N1—C1161.3 (13)C17—C18—N2—C158.9 (6)
C4B—C5—N1—C1−167.3 (11)N2—C14—S3—Sn2176.6 (4)
C4A—C5—N1—C2−17.8 (13)S4—C14—S3—Sn2−4.5 (3)
C4B—C5—N1—C213.6 (11)C19—Sn2—S3—C1485.4 (3)
C3—C2—N1—C1−178.7 (6)C23—Sn2—S3—C14−79.5 (3)
C3—C2—N1—C50.4 (7)Cl2—Sn2—S3—C14−179.3 (2)
N1—C1—S1—Sn1179.9 (4)S4—Sn2—S3—C142.58 (18)
S2—C1—S1—Sn1−1.0 (3)N2—C14—S4—Sn2−177.2 (5)
C10—Sn1—S1—C184.8 (3)S3—C14—S4—Sn24.0 (3)
C6—Sn1—S1—C1−81.1 (3)C19—Sn2—S4—C14−121.3 (3)
Cl1—Sn1—S1—C1−178.15 (18)C23—Sn2—S4—C14114.4 (3)
S2—Sn1—S1—C10.56 (18)Cl2—Sn2—S4—C14−6.7 (3)
N1—C1—S2—Sn1179.9 (5)S3—Sn2—S4—C14−2.67 (19)
S1—C1—S2—Sn10.9 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2363).

References

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