Abstract
The dinuclear centrosymmetric title compound, [Sn2(C6H5)6(C6H8N2S4)]·CH2Cl2, features a distorted cis-trigonal–bipyramidal coordination geometry for Sn based on a C3S2 donor set. The dinuclear molecule lies across a centre of inversion. The solvent dichloromethane molecule is disordered about a centre of inversion.
Related literature
For a review of tin dithiocarbamates, see: Tiekink (2008 ▶). For a related structure, see: Yin et al. (2002 ▶). For analysis of trigonal–bipyramidal geometries, see: Addison et al. (1984 ▶).
Experimental
Crystal data
[Sn2(C6H5)6(C6H8N2S4)]·CH2Cl2
M r = 1021.37
Monoclinic,
a = 14.681 (5) Å
b = 10.758 (3) Å
c = 13.470 (4) Å
β = 90.379 (6)°
V = 2127.3 (11) Å3
Z = 2
Mo Kα radiation
μ = 1.53 mm−1
T = 98 (2) K
0.35 × 0.15 × 0.01 mm
Data collection
Rigaku AFC12κ/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.354, T max = 1 (expected range = 0.346–0.977)
14400 measured reflections
4389 independent reflections
4021 reflections with I > 2σ(I)
R int = 0.048
Refinement
R[F 2 > 2σ(F 2)] = 0.048
wR(F 2) = 0.113
S = 1.10
4389 reflections
244 parameters
H-atom parameters constrained
Δρmax = 0.77 e Å−3
Δρmin = −1.12 e Å−3
Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025890/ng2481sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025890/ng2481Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Comment
Tin dithiocarbamates continue to attract interest owing to their variety of applications (Tiekink, 2008). The title compound, Ph3SnS2CN(CH2CH2)2NCS2SnPh3, has been reported previously as a methanol solvate (Yin et al., 2002). The present structure (I) has been isolated as a dichloromethane solvate, Fig. 1. The molecule is centrosymmetric so that the Ph3Sn entities lie to either side of the pyrrolidine ring which adopts a chair conformation. The dithiocarbamate ligand coordinates in an asymmetric mode, forming Sn—S1 and Sn—S2 distances of 2.4699 (13) and 3.0715 (13) Å, respectively. The coordination geometry is based on a distorted trigonal bipyramid as indicated by the value of τ = 0.64 (Addison et al., 1984).
Experimental
The title compound was prepared by following a literature procedure (Yin et al., 2002). Colourless crystals were isolated by the slow evaporation of a dichloromethane solution of (I); m.p. 487–489 K (crystal turned opaque at 363–368 K). TGA: two steps, First mass loss 7.2% (onset 388.3 K, midpoint 392.6 K, endset 396.9 K) corresponds to loss CH2Cl2 (8.2% theoretical). Second mass loss 69.3% (onset 558.5 K, midpoint 620 K, endset 680 K), corresponds to decomposition to SnS (total experimental mass loss 76.5% cf. theoretical value 70.5%). IR (cm-1): 1427, 1416 (strong, C═N), 1214 (strong, C—S).
Refinement
The H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The solvent dichloromethane molecule was disordered about a centre of inversion and was modelled with anisotropic displacement parameters.
Figures
Fig. 1.
Molecular structure of (I) showing the crystallographic numbering scheme. Displacement ellipsoids are shown at the 70% probability level. Unlabelled atoms are related by the symmetry operation i: -x, 1-y, 1-z. The disordered dichloromethane molecule is omitted.
Crystal data
| [Sn2(C6H5)6(C6H8N2S4)]·CH2Cl2 | F000 = 1020 |
| Mr = 1021.37 | Dx = 1.594 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71069 Å |
| Hall symbol: -P 2ybc | Cell parameters from 13756 reflections |
| a = 14.681 (5) Å | θ = 2.4–40.7º |
| b = 10.758 (3) Å | µ = 1.53 mm−1 |
| c = 13.470 (4) Å | T = 98 (2) K |
| β = 90.379 (6)º | Plate, colourless |
| V = 2127.3 (11) Å3 | 0.35 × 0.15 × 0.02 mm |
| Z = 2 |
Data collection
| Rigaku AFC12κ/SATURN724 diffractometer | 4389 independent reflections |
| Radiation source: fine-focus sealed tube | 4021 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.048 |
| T = 98(2) K | θmax = 26.5º |
| ω scans | θmin = 2.4º |
| Absorption correction: multi-scan(ABSCOR; Higashi, 1995) | h = −17→18 |
| Tmin = 0.354, Tmax = 1 | k = −13→13 |
| 14400 measured reflections | l = −16→16 |
Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
| wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.04P)2 + 8.4194P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max = 0.001 |
| 4389 reflections | Δρmax = 0.77 e Å−3 |
| 244 parameters | Δρmin = −1.12 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Sn | 0.23132 (2) | 0.37950 (3) | 0.17164 (2) | 0.02056 (11) | |
| S1 | 0.10733 (8) | 0.32408 (10) | 0.28651 (9) | 0.0237 (3) | |
| S2 | 0.12861 (8) | 0.59723 (11) | 0.26696 (9) | 0.0244 (3) | |
| N1 | 0.0190 (3) | 0.4872 (4) | 0.3970 (3) | 0.0250 (9) | |
| C1 | 0.0795 (3) | 0.4757 (4) | 0.3239 (3) | 0.0228 (9) | |
| C2 | −0.0077 (3) | 0.6087 (4) | 0.4381 (4) | 0.0264 (11) | |
| H2A | −0.0745 | 0.6193 | 0.4320 | 0.032* | |
| H2B | 0.0220 | 0.6761 | 0.4002 | 0.032* | |
| C3 | 0.0208 (3) | 0.6161 (4) | 0.5471 (4) | 0.0260 (10) | |
| H3A | 0.0880 | 0.6128 | 0.5525 | 0.031* | |
| H3B | 0.0001 | 0.6961 | 0.5756 | 0.031* | |
| C4 | 0.2559 (3) | 0.1881 (4) | 0.1326 (3) | 0.0212 (9) | |
| C5 | 0.2678 (3) | 0.1546 (5) | 0.0335 (4) | 0.0238 (10) | |
| H5 | 0.2690 | 0.2174 | −0.0160 | 0.029* | |
| C6 | 0.2780 (3) | 0.0316 (5) | 0.0060 (4) | 0.0284 (11) | |
| H6 | 0.2846 | 0.0103 | −0.0620 | 0.034* | |
| C7 | 0.2785 (3) | −0.0610 (4) | 0.0782 (4) | 0.0284 (11) | |
| H7 | 0.2869 | −0.1453 | 0.0596 | 0.034* | |
| C8 | 0.2666 (4) | −0.0303 (5) | 0.1768 (4) | 0.0320 (12) | |
| H8 | 0.2664 | −0.0936 | 0.2259 | 0.038* | |
| C9 | 0.2549 (3) | 0.0934 (4) | 0.2042 (4) | 0.0270 (10) | |
| H9 | 0.2462 | 0.1139 | 0.2721 | 0.032* | |
| C10 | 0.1869 (3) | 0.4710 (4) | 0.0402 (3) | 0.0231 (10) | |
| C11 | 0.2262 (4) | 0.5821 (5) | 0.0088 (4) | 0.0413 (14) | |
| H11 | 0.2767 | 0.6157 | 0.0442 | 0.050* | |
| C12 | 0.1920 (4) | 0.6440 (5) | −0.0742 (5) | 0.0424 (15) | |
| H12 | 0.2184 | 0.7205 | −0.0944 | 0.051* | |
| C13 | 0.1199 (4) | 0.5948 (4) | −0.1273 (4) | 0.0272 (10) | |
| H13 | 0.0966 | 0.6377 | −0.1836 | 0.033* | |
| C14 | 0.0818 (4) | 0.4841 (5) | −0.0989 (4) | 0.0344 (12) | |
| H14 | 0.0324 | 0.4497 | −0.1356 | 0.041* | |
| C15 | 0.1166 (4) | 0.4223 (5) | −0.0151 (4) | 0.0307 (11) | |
| H15 | 0.0908 | 0.3449 | 0.0038 | 0.037* | |
| C16 | 0.3474 (3) | 0.4550 (4) | 0.2475 (4) | 0.0238 (10) | |
| C17 | 0.4094 (3) | 0.3737 (5) | 0.2921 (4) | 0.0297 (11) | |
| H17 | 0.4011 | 0.2865 | 0.2860 | 0.036* | |
| C18 | 0.4830 (4) | 0.4199 (5) | 0.3453 (4) | 0.0369 (12) | |
| H18 | 0.5247 | 0.3640 | 0.3759 | 0.044* | |
| C19 | 0.4966 (4) | 0.5477 (5) | 0.3543 (4) | 0.0378 (13) | |
| H19 | 0.5475 | 0.5791 | 0.3904 | 0.045* | |
| C20 | 0.4352 (3) | 0.6280 (5) | 0.3103 (4) | 0.0308 (11) | |
| H20 | 0.4439 | 0.7151 | 0.3165 | 0.037* | |
| C21 | 0.3608 (3) | 0.5833 (4) | 0.2570 (4) | 0.0247 (10) | |
| H21 | 0.3191 | 0.6397 | 0.2270 | 0.030* | |
| C22 | 0.5409 (12) | 0.0134 (14) | 0.5721 (11) | 0.066 (4) | 0.50 |
| H22A | 0.6046 | 0.0434 | 0.5764 | 0.080* | 0.50 |
| H22B | 0.5172 | 0.0006 | 0.6400 | 0.080* | 0.50 |
| Cl1 | 0.4667 (2) | 0.1259 (2) | 0.4994 (2) | 0.0958 (9) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn | 0.02652 (19) | 0.01628 (17) | 0.01887 (18) | −0.00089 (12) | −0.00114 (13) | 0.00000 (11) |
| S1 | 0.0281 (6) | 0.0167 (5) | 0.0263 (6) | −0.0002 (4) | 0.0029 (5) | −0.0026 (4) |
| S2 | 0.0294 (6) | 0.0191 (5) | 0.0247 (6) | 0.0000 (5) | 0.0020 (5) | −0.0025 (4) |
| N1 | 0.027 (2) | 0.0180 (19) | 0.030 (2) | 0.0038 (16) | 0.0035 (17) | 0.0006 (16) |
| C1 | 0.024 (2) | 0.023 (2) | 0.021 (2) | 0.0046 (18) | −0.0024 (18) | −0.0055 (18) |
| C2 | 0.025 (2) | 0.019 (2) | 0.035 (3) | 0.0045 (18) | 0.010 (2) | −0.0009 (19) |
| C3 | 0.024 (2) | 0.018 (2) | 0.036 (3) | 0.0017 (18) | 0.007 (2) | −0.001 (2) |
| C4 | 0.026 (2) | 0.015 (2) | 0.023 (2) | 0.0014 (17) | 0.0030 (18) | −0.0032 (17) |
| C5 | 0.024 (2) | 0.027 (2) | 0.021 (2) | 0.0037 (19) | 0.0010 (18) | −0.0005 (19) |
| C6 | 0.032 (3) | 0.030 (3) | 0.023 (3) | 0.001 (2) | −0.001 (2) | −0.008 (2) |
| C7 | 0.029 (3) | 0.018 (2) | 0.038 (3) | −0.0012 (19) | −0.002 (2) | −0.007 (2) |
| C8 | 0.043 (3) | 0.021 (2) | 0.032 (3) | 0.001 (2) | 0.007 (2) | 0.006 (2) |
| C9 | 0.035 (3) | 0.024 (2) | 0.022 (2) | 0.001 (2) | 0.003 (2) | 0.0007 (19) |
| C10 | 0.032 (2) | 0.018 (2) | 0.019 (2) | 0.0025 (18) | 0.0003 (19) | −0.0009 (17) |
| C11 | 0.057 (4) | 0.033 (3) | 0.034 (3) | −0.019 (3) | −0.024 (3) | 0.012 (2) |
| C12 | 0.060 (4) | 0.029 (3) | 0.039 (3) | −0.014 (3) | −0.013 (3) | 0.013 (2) |
| C13 | 0.041 (3) | 0.022 (2) | 0.019 (2) | 0.006 (2) | −0.001 (2) | −0.0006 (19) |
| C14 | 0.039 (3) | 0.029 (3) | 0.035 (3) | −0.004 (2) | −0.016 (2) | 0.002 (2) |
| C15 | 0.038 (3) | 0.024 (2) | 0.030 (3) | −0.007 (2) | −0.009 (2) | 0.003 (2) |
| C16 | 0.018 (2) | 0.027 (2) | 0.026 (3) | −0.0031 (18) | −0.0007 (18) | −0.0023 (19) |
| C17 | 0.028 (3) | 0.031 (3) | 0.030 (3) | 0.001 (2) | −0.004 (2) | 0.001 (2) |
| C18 | 0.029 (3) | 0.036 (3) | 0.045 (3) | 0.002 (2) | −0.006 (2) | 0.004 (3) |
| C19 | 0.032 (3) | 0.040 (3) | 0.041 (3) | −0.011 (2) | −0.005 (2) | −0.005 (3) |
| C20 | 0.026 (3) | 0.032 (3) | 0.034 (3) | −0.009 (2) | −0.002 (2) | −0.003 (2) |
| C21 | 0.023 (2) | 0.023 (2) | 0.027 (3) | −0.0027 (19) | 0.0017 (19) | 0.0021 (19) |
| C22 | 0.102 (12) | 0.050 (8) | 0.048 (9) | 0.001 (8) | 0.023 (8) | 0.001 (7) |
| Cl1 | 0.155 (3) | 0.0477 (11) | 0.0854 (17) | 0.0173 (13) | 0.0274 (17) | 0.0024 (11) |
Geometric parameters (Å, °)
| Sn—C10 | 2.125 (5) | C10—C15 | 1.373 (7) |
| Sn—C16 | 2.141 (5) | C10—C11 | 1.394 (7) |
| Sn—C4 | 2.157 (4) | C11—C12 | 1.392 (8) |
| Sn—S1 | 2.4699 (13) | C11—H11 | 0.9500 |
| Sn—S2 | 3.0715 (13) | C12—C13 | 1.378 (8) |
| S1—C1 | 1.756 (5) | C12—H12 | 0.9500 |
| S2—C1 | 1.680 (5) | C13—C14 | 1.370 (7) |
| N1—C1 | 1.337 (6) | C13—H13 | 0.9500 |
| N1—C3i | 1.466 (6) | C14—C15 | 1.403 (7) |
| N1—C2 | 1.473 (6) | C14—H14 | 0.9500 |
| C2—C3 | 1.527 (7) | C15—H15 | 0.9500 |
| C2—H2A | 0.9900 | C16—C17 | 1.396 (7) |
| C2—H2B | 0.9900 | C16—C21 | 1.400 (7) |
| C3—N1i | 1.466 (6) | C17—C18 | 1.385 (7) |
| C3—H3A | 0.9900 | C17—H17 | 0.9500 |
| C3—H3B | 0.9900 | C18—C19 | 1.395 (8) |
| C4—C5 | 1.394 (6) | C18—H18 | 0.9500 |
| C4—C9 | 1.403 (7) | C19—C20 | 1.380 (8) |
| C5—C6 | 1.382 (7) | C19—H19 | 0.9500 |
| C5—H5 | 0.9500 | C20—C21 | 1.389 (7) |
| C6—C7 | 1.392 (7) | C20—H20 | 0.9500 |
| C6—H6 | 0.9500 | C21—H21 | 0.9500 |
| C7—C8 | 1.380 (7) | C22—Cl1ii | 1.784 (15) |
| C7—H7 | 0.9500 | C22—Cl1 | 1.896 (16) |
| C8—C9 | 1.392 (7) | C22—H22A | 0.9900 |
| C8—H8 | 0.9500 | C22—H22B | 0.9900 |
| C9—H9 | 0.9500 | Cl1—C22ii | 1.784 (15) |
| C10—Sn—C16 | 117.43 (18) | C8—C9—H9 | 119.7 |
| C10—Sn—C4 | 106.86 (18) | C4—C9—H9 | 119.7 |
| C16—Sn—C4 | 110.16 (18) | C15—C10—C11 | 118.3 (5) |
| C10—Sn—S1 | 114.23 (13) | C15—C10—Sn | 120.1 (4) |
| C16—Sn—S1 | 112.36 (13) | C11—C10—Sn | 121.7 (4) |
| C4—Sn—S1 | 92.74 (12) | C12—C11—C10 | 120.4 (5) |
| C10—Sn—S2 | 81.15 (12) | C12—C11—H11 | 119.8 |
| C16—Sn—S2 | 84.41 (13) | C10—C11—H11 | 119.8 |
| C4—Sn—S2 | 156.03 (12) | C13—C12—C11 | 120.3 (5) |
| S1—Sn—S2 | 63.66 (4) | C13—C12—H12 | 119.9 |
| C1—S1—Sn | 97.41 (16) | C11—C12—H12 | 119.9 |
| C1—S2—Sn | 79.09 (16) | C14—C13—C12 | 120.2 (5) |
| C1—N1—C3i | 125.3 (4) | C14—C13—H13 | 119.9 |
| C1—N1—C2 | 122.6 (4) | C12—C13—H13 | 119.9 |
| C3i—N1—C2 | 111.8 (4) | C13—C14—C15 | 119.3 (5) |
| N1—C1—S2 | 123.6 (4) | C13—C14—H14 | 120.4 |
| N1—C1—S1 | 117.0 (4) | C15—C14—H14 | 120.4 |
| S2—C1—S1 | 119.4 (3) | C10—C15—C14 | 121.6 (5) |
| N1—C2—C3 | 109.6 (4) | C10—C15—H15 | 119.2 |
| N1—C2—H2A | 109.7 | C14—C15—H15 | 119.2 |
| C3—C2—H2A | 109.7 | C17—C16—C21 | 119.2 (5) |
| N1—C2—H2B | 109.7 | C17—C16—Sn | 118.9 (4) |
| C3—C2—H2B | 109.7 | C21—C16—Sn | 121.9 (4) |
| H2A—C2—H2B | 108.2 | C18—C17—C16 | 120.2 (5) |
| N1i—C3—C2 | 110.3 (4) | C18—C17—H17 | 119.9 |
| N1i—C3—H3A | 109.6 | C16—C17—H17 | 119.9 |
| C2—C3—H3A | 109.6 | C17—C18—C19 | 120.6 (5) |
| N1i—C3—H3B | 109.6 | C17—C18—H18 | 119.7 |
| C2—C3—H3B | 109.6 | C19—C18—H18 | 119.7 |
| H3A—C3—H3B | 108.1 | C20—C19—C18 | 119.1 (5) |
| C5—C4—C9 | 118.2 (4) | C20—C19—H19 | 120.4 |
| C5—C4—Sn | 120.2 (3) | C18—C19—H19 | 120.4 |
| C9—C4—Sn | 121.5 (3) | C19—C20—C21 | 121.0 (5) |
| C6—C5—C4 | 121.2 (5) | C19—C20—H20 | 119.5 |
| C6—C5—H5 | 119.4 | C21—C20—H20 | 119.5 |
| C4—C5—H5 | 119.4 | C20—C21—C16 | 119.8 (5) |
| C5—C6—C7 | 119.8 (5) | C20—C21—H21 | 120.1 |
| C5—C6—H6 | 120.1 | C16—C21—H21 | 120.1 |
| C7—C6—H6 | 120.1 | Cl1ii—C22—Cl1 | 102.9 (8) |
| C8—C7—C6 | 120.1 (5) | Cl1ii—C22—H22A | 111.2 |
| C8—C7—H7 | 120.0 | Cl1—C22—H22A | 111.2 |
| C6—C7—H7 | 120.0 | Cl1ii—C22—H22B | 111.2 |
| C7—C8—C9 | 120.0 (5) | Cl1—C22—H22B | 111.2 |
| C7—C8—H8 | 120.0 | H22A—C22—H22B | 109.1 |
| C9—C8—H8 | 120.0 | C22ii—Cl1—C22 | 77.1 (8) |
| C8—C9—C4 | 120.6 (5) | ||
| C10—Sn—S1—C1 | −69.6 (2) | Sn—C4—C9—C8 | 176.9 (4) |
| C16—Sn—S1—C1 | 67.4 (2) | C16—Sn—C10—C15 | 175.8 (4) |
| C4—Sn—S1—C1 | −179.5 (2) | C4—Sn—C10—C15 | 51.5 (4) |
| S2—Sn—S1—C1 | −3.88 (16) | S1—Sn—C10—C15 | −49.5 (4) |
| C10—Sn—S2—C1 | 126.8 (2) | S2—Sn—C10—C15 | −105.3 (4) |
| C16—Sn—S2—C1 | −114.3 (2) | C16—Sn—C10—C11 | −5.6 (5) |
| C4—Sn—S2—C1 | 15.0 (4) | C4—Sn—C10—C11 | −129.8 (5) |
| S1—Sn—S2—C1 | 4.10 (17) | S1—Sn—C10—C11 | 129.2 (4) |
| C3i—N1—C1—S2 | −175.8 (4) | S2—Sn—C10—C11 | 73.4 (4) |
| C2—N1—C1—S2 | −2.8 (7) | C15—C10—C11—C12 | 2.7 (9) |
| C3i—N1—C1—S1 | 4.6 (7) | Sn—C10—C11—C12 | −176.0 (5) |
| C2—N1—C1—S1 | 177.6 (4) | C10—C11—C12—C13 | −1.2 (10) |
| Sn—S2—C1—N1 | 174.5 (4) | C11—C12—C13—C14 | −0.4 (9) |
| Sn—S2—C1—S1 | −5.9 (2) | C12—C13—C14—C15 | 0.5 (8) |
| Sn—S1—C1—N1 | −173.0 (3) | C11—C10—C15—C14 | −2.6 (8) |
| Sn—S1—C1—S2 | 7.3 (3) | Sn—C10—C15—C14 | 176.1 (4) |
| C1—N1—C2—C3 | −116.5 (5) | C13—C14—C15—C10 | 1.1 (8) |
| C3i—N1—C2—C3 | 57.4 (5) | C10—Sn—C16—C17 | −143.2 (4) |
| N1—C2—C3—N1i | −56.4 (5) | C4—Sn—C16—C17 | −20.6 (4) |
| C10—Sn—C4—C5 | 18.7 (4) | S1—Sn—C16—C17 | 81.2 (4) |
| C16—Sn—C4—C5 | −110.0 (4) | S2—Sn—C16—C17 | 139.8 (4) |
| S1—Sn—C4—C5 | 135.0 (4) | C10—Sn—C16—C21 | 39.4 (5) |
| S2—Sn—C4—C5 | 125.3 (3) | C4—Sn—C16—C21 | 162.0 (4) |
| C10—Sn—C4—C9 | −157.4 (4) | S1—Sn—C16—C21 | −96.1 (4) |
| C16—Sn—C4—C9 | 74.0 (4) | S2—Sn—C16—C21 | −37.6 (4) |
| S1—Sn—C4—C9 | −41.1 (4) | C21—C16—C17—C18 | 0.2 (8) |
| S2—Sn—C4—C9 | −50.8 (6) | Sn—C16—C17—C18 | −177.2 (4) |
| C9—C4—C5—C6 | 0.3 (7) | C16—C17—C18—C19 | −0.5 (9) |
| Sn—C4—C5—C6 | −175.9 (4) | C17—C18—C19—C20 | 0.6 (9) |
| C4—C5—C6—C7 | −1.4 (7) | C18—C19—C20—C21 | −0.4 (9) |
| C5—C6—C7—C8 | 1.6 (8) | C19—C20—C21—C16 | 0.0 (8) |
| C6—C7—C8—C9 | −0.5 (8) | C17—C16—C21—C20 | 0.0 (7) |
| C7—C8—C9—C4 | −0.6 (8) | Sn—C16—C21—C20 | 177.4 (4) |
| C5—C4—C9—C8 | 0.7 (7) | Cl1ii—C22—Cl1—C22ii | 0.000 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2481).
References
- Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356.
- Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
- Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
- Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Tiekink, E. R. T. (2008). Appl. Organomet. Chem.22, 553–550.
- Yin, H.-D., Ma, C.-L., Wang, Y., Fang, H.-X. & Shao, J.-X. (2002). Chin. J. Chem.60, 897–903.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025890/ng2481sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025890/ng2481Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

