metal-organic compounds
The Sn atom in the title compound, [Sn(CH3)2(C15H9Cl2O2)2], has a highly distorted octahedral coordination that may be best described as skew-trapezoid planar for the carboxylates. The ligands are asymmetrically coordinated to the Sn atoms with Sn—O covalent bonds and dative bonds. The mean Sn—C distance for the methyl groups is 2.094 (6) Å, with a bent C—Sn—C angle of 145.77 (11)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014710/lh6234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014710/lh6234Isup2.hkl |
CCDC reference: 245149
Computing details top
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Crystal data top
[Sn(CH3)2(C15H9Cl2O2)2] | Z = 2 |
Mr = 733.00 | F(000) = 732 |
Triclinic, P1 | Dx = 1.625 Mg m−3 |
Hall symbol: -P 1 | Melting point: 473-476 K K |
a = 8.4740 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2770 (12) Å | Cell parameters from 12446 reflections |
c = 19.472 (4) Å | θ = 3.1–27.3° |
α = 95.817 (6)° | µ = 1.25 mm−1 |
β = 99.748 (7)° | T = 173 K |
γ = 114.116 (8)° | Prism, colorless |
V = 1497.7 (4) Å3 | 0.14 × 0.12 × 0.10 mm |
Data collection top
Nonius KappaCCD diffractometer | 6683 independent reflections |
Radiation source: fine-focus sealed tube | 5570 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and φ scans | θmax = 27.3°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −10→10 |
Tmin = 0.845, Tmax = 0.886 | k = −13→13 |
12446 measured reflections | l = −25→25 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.4509P] where P = (Fo2 + 2Fc2)/3 |
6683 reflections | (Δ/σ)max = 0.01 |
372 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.26139 (2) | 0.005495 (17) | 0.417574 (9) | 0.02159 (7) | |
Cl1 | −0.24802 (11) | −0.55145 (9) | −0.01231 (4) | 0.0531 (2) | |
Cl2 | −0.71382 (10) | 0.12751 (9) | 0.03621 (4) | 0.0447 (2) | |
Cl3 | 0.02708 (9) | 0.65950 (7) | 0.62064 (4) | 0.03262 (16) | |
Cl4 | 1.05421 (10) | 0.80855 (8) | 0.90539 (4) | 0.04376 (19) | |
O1 | 0.0518 (2) | 0.02613 (19) | 0.35061 (9) | 0.0303 (4) | |
O2 | 0.0772 (2) | −0.16400 (18) | 0.29998 (9) | 0.0281 (4) | |
O3 | 0.2828 (2) | 0.19300 (18) | 0.48343 (9) | 0.0262 (4) | |
O4 | 0.4908 (2) | 0.13198 (18) | 0.53037 (9) | 0.0281 (4) | |
C1 | 0.1230 (3) | −0.1579 (3) | 0.46970 (15) | 0.0305 (6) | |
H1A | 0.2003 | −0.1499 | 0.5150 | 0.046* | |
H1B | 0.0860 | −0.2531 | 0.4401 | 0.046* | |
H1C | 0.0178 | −0.1476 | 0.4784 | 0.046* | |
C2 | 0.4616 (4) | 0.0795 (3) | 0.36113 (15) | 0.0339 (6) | |
H2A | 0.5746 | 0.1453 | 0.3941 | 0.051* | |
H2B | 0.4300 | 0.1312 | 0.3256 | 0.051* | |
H2C | 0.4737 | −0.0036 | 0.3374 | 0.051* | |
C3 | 0.0026 (3) | −0.0817 (3) | 0.29848 (13) | 0.0243 (5) | |
C4 | −0.1431 (3) | −0.1031 (3) | 0.23630 (13) | 0.0245 (5) | |
C5 | −0.2237 (3) | −0.0140 (3) | 0.24145 (13) | 0.0251 (5) | |
H5 | −0.1886 | 0.0465 | 0.2868 | 0.030* | |
C6 | −0.1736 (3) | −0.2153 (3) | 0.17416 (13) | 0.0239 (5) | |
C7 | −0.0449 (4) | −0.1902 (3) | 0.13481 (14) | 0.0316 (6) | |
H7 | 0.0605 | −0.1016 | 0.1476 | 0.038* | |
C8 | −0.0681 (4) | −0.2928 (3) | 0.07707 (15) | 0.0352 (6) | |
H8 | 0.0197 | −0.2742 | 0.0501 | 0.042* | |
C9 | −0.2200 (4) | −0.4219 (3) | 0.05950 (14) | 0.0319 (6) | |
C10 | −0.3494 (4) | −0.4506 (3) | 0.09780 (15) | 0.0325 (6) | |
H10 | −0.4533 | −0.5402 | 0.0852 | 0.039* | |
C11 | −0.3258 (3) | −0.3467 (3) | 0.15506 (14) | 0.0272 (6) | |
H11 | −0.4147 | −0.3657 | 0.1815 | 0.033* | |
C12 | −0.3553 (3) | 0.0060 (3) | 0.18972 (14) | 0.0264 (6) | |
C13 | −0.4555 (3) | −0.0855 (3) | 0.12429 (14) | 0.0298 (6) | |
H13 | −0.4474 | −0.1740 | 0.1119 | 0.036* | |
C14 | −0.5661 (4) | −0.0489 (3) | 0.07751 (15) | 0.0323 (6) | |
H14 | −0.6332 | −0.1116 | 0.0333 | 0.039* | |
C15 | −0.5780 (3) | 0.0799 (3) | 0.09582 (14) | 0.0305 (6) | |
C16 | −0.4836 (4) | 0.1716 (3) | 0.16014 (15) | 0.0331 (6) | |
H16 | −0.4937 | 0.2593 | 0.1724 | 0.040* | |
C17 | −0.3743 (4) | 0.1337 (3) | 0.20629 (14) | 0.0302 (6) | |
H17 | −0.3098 | 0.1964 | 0.2508 | 0.036* | |
C18 | 0.4145 (3) | 0.2129 (3) | 0.53461 (13) | 0.0228 (5) | |
C19 | 0.4681 (3) | 0.3310 (2) | 0.59681 (13) | 0.0218 (5) | |
C20 | 0.6116 (3) | 0.3532 (3) | 0.64726 (13) | 0.0245 (5) | |
H20 | 0.6584 | 0.2846 | 0.6398 | 0.029* | |
C21 | 0.3564 (3) | 0.4112 (2) | 0.60124 (13) | 0.0202 (5) | |
C22 | 0.3138 (3) | 0.4765 (2) | 0.54587 (13) | 0.0222 (5) | |
H22 | 0.3540 | 0.4683 | 0.5037 | 0.027* | |
C23 | 0.2135 (3) | 0.5529 (2) | 0.55209 (13) | 0.0223 (5) | |
H23 | 0.1870 | 0.5989 | 0.5148 | 0.027* | |
C24 | 0.1520 (3) | 0.5620 (2) | 0.61307 (14) | 0.0231 (5) | |
C25 | 0.1876 (3) | 0.4945 (3) | 0.66803 (14) | 0.0263 (6) | |
H25 | 0.1433 | 0.4997 | 0.7094 | 0.032* | |
C26 | 0.2894 (3) | 0.4193 (3) | 0.66109 (13) | 0.0241 (5) | |
H26 | 0.3140 | 0.3721 | 0.6982 | 0.029* | |
C27 | 0.7075 (3) | 0.4645 (3) | 0.71148 (13) | 0.0250 (5) | |
C28 | 0.8130 (4) | 0.4355 (3) | 0.76525 (14) | 0.0321 (6) | |
H28 | 0.8128 | 0.3425 | 0.7607 | 0.038* | |
C29 | 0.9181 (4) | 0.5401 (3) | 0.82526 (15) | 0.0359 (7) | |
H29 | 0.9889 | 0.5189 | 0.8616 | 0.043* | |
C30 | 0.9188 (3) | 0.6749 (3) | 0.83167 (14) | 0.0310 (6) | |
C31 | 0.8164 (4) | 0.7075 (3) | 0.77893 (15) | 0.0317 (6) | |
H31 | 0.8187 | 0.8012 | 0.7837 | 0.038* | |
C32 | 0.7115 (3) | 0.6032 (3) | 0.71965 (14) | 0.0279 (6) | |
H32 | 0.6408 | 0.6254 | 0.6837 | 0.034* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02230 (10) | 0.01842 (9) | 0.02110 (10) | 0.00858 (7) | 0.00058 (7) | −0.00027 (7) |
Cl1 | 0.0521 (5) | 0.0577 (5) | 0.0428 (5) | 0.0328 (4) | −0.0090 (4) | −0.0255 (4) |
Cl2 | 0.0458 (4) | 0.0523 (4) | 0.0395 (4) | 0.0335 (4) | −0.0083 (3) | 0.0011 (3) |
Cl3 | 0.0314 (4) | 0.0343 (3) | 0.0356 (4) | 0.0202 (3) | 0.0061 (3) | −0.0025 (3) |
Cl4 | 0.0360 (4) | 0.0483 (4) | 0.0279 (4) | 0.0082 (3) | −0.0025 (3) | −0.0134 (3) |
O1 | 0.0349 (10) | 0.0286 (9) | 0.0233 (10) | 0.0173 (9) | −0.0067 (8) | −0.0060 (8) |
O2 | 0.0296 (10) | 0.0250 (9) | 0.0269 (10) | 0.0137 (8) | −0.0016 (8) | −0.0007 (7) |
O3 | 0.0265 (9) | 0.0241 (9) | 0.0237 (9) | 0.0123 (8) | −0.0036 (8) | −0.0037 (7) |
O4 | 0.0281 (10) | 0.0256 (9) | 0.0290 (10) | 0.0145 (8) | −0.0001 (8) | −0.0038 (8) |
C1 | 0.0222 (13) | 0.0295 (14) | 0.0345 (16) | 0.0074 (12) | 0.0017 (12) | 0.0083 (12) |
C2 | 0.0310 (15) | 0.0336 (15) | 0.0305 (15) | 0.0072 (13) | 0.0085 (12) | 0.0054 (12) |
C3 | 0.0257 (13) | 0.0222 (12) | 0.0200 (13) | 0.0079 (11) | 0.0011 (11) | 0.0010 (10) |
C4 | 0.0264 (13) | 0.0234 (13) | 0.0194 (13) | 0.0090 (11) | 0.0007 (11) | 0.0021 (10) |
C5 | 0.0267 (13) | 0.0275 (13) | 0.0188 (13) | 0.0114 (11) | 0.0017 (11) | 0.0024 (10) |
C6 | 0.0268 (13) | 0.0239 (12) | 0.0187 (13) | 0.0122 (11) | −0.0015 (10) | 0.0006 (10) |
C7 | 0.0284 (14) | 0.0312 (14) | 0.0296 (15) | 0.0105 (12) | 0.0019 (12) | −0.0001 (12) |
C8 | 0.0358 (16) | 0.0426 (16) | 0.0286 (15) | 0.0205 (14) | 0.0060 (13) | 0.0009 (13) |
C9 | 0.0357 (16) | 0.0340 (15) | 0.0255 (14) | 0.0220 (13) | −0.0056 (12) | −0.0060 (12) |
C10 | 0.0353 (15) | 0.0226 (13) | 0.0322 (16) | 0.0124 (12) | −0.0072 (13) | 0.0003 (11) |
C11 | 0.0279 (14) | 0.0264 (13) | 0.0228 (13) | 0.0106 (12) | −0.0009 (11) | 0.0020 (11) |
C12 | 0.0260 (13) | 0.0285 (13) | 0.0233 (14) | 0.0121 (12) | 0.0031 (11) | 0.0023 (11) |
C13 | 0.0300 (14) | 0.0291 (14) | 0.0278 (15) | 0.0155 (12) | −0.0026 (12) | −0.0012 (11) |
C14 | 0.0312 (15) | 0.0337 (15) | 0.0272 (15) | 0.0156 (13) | −0.0046 (12) | −0.0028 (12) |
C15 | 0.0263 (14) | 0.0391 (15) | 0.0279 (15) | 0.0183 (13) | 0.0010 (12) | 0.0058 (12) |
C16 | 0.0367 (16) | 0.0345 (15) | 0.0327 (16) | 0.0224 (13) | 0.0049 (13) | 0.0007 (12) |
C17 | 0.0331 (15) | 0.0326 (14) | 0.0235 (14) | 0.0160 (13) | 0.0021 (12) | −0.0011 (11) |
C18 | 0.0218 (12) | 0.0192 (12) | 0.0226 (13) | 0.0056 (10) | 0.0030 (10) | 0.0017 (10) |
C19 | 0.0215 (12) | 0.0180 (11) | 0.0238 (13) | 0.0081 (10) | 0.0028 (10) | 0.0023 (10) |
C20 | 0.0265 (13) | 0.0215 (12) | 0.0258 (14) | 0.0127 (11) | 0.0026 (11) | 0.0015 (10) |
C21 | 0.0189 (12) | 0.0155 (11) | 0.0196 (12) | 0.0040 (10) | 0.0000 (10) | −0.0023 (9) |
C22 | 0.0215 (12) | 0.0214 (12) | 0.0196 (13) | 0.0060 (10) | 0.0053 (10) | 0.0006 (10) |
C23 | 0.0224 (13) | 0.0194 (12) | 0.0226 (13) | 0.0082 (11) | 0.0020 (10) | 0.0016 (10) |
C24 | 0.0178 (12) | 0.0194 (12) | 0.0288 (14) | 0.0071 (10) | 0.0048 (10) | −0.0037 (10) |
C25 | 0.0252 (13) | 0.0253 (13) | 0.0233 (14) | 0.0072 (11) | 0.0058 (11) | −0.0012 (11) |
C26 | 0.0242 (13) | 0.0230 (12) | 0.0206 (13) | 0.0080 (11) | 0.0006 (10) | 0.0022 (10) |
C27 | 0.0232 (13) | 0.0279 (13) | 0.0219 (13) | 0.0124 (11) | 0.0004 (11) | −0.0013 (10) |
C28 | 0.0369 (16) | 0.0316 (14) | 0.0290 (15) | 0.0195 (13) | 0.0011 (12) | 0.0022 (12) |
C29 | 0.0352 (16) | 0.0438 (16) | 0.0257 (15) | 0.0207 (14) | −0.0058 (12) | −0.0001 (13) |
C30 | 0.0237 (13) | 0.0367 (15) | 0.0239 (14) | 0.0092 (12) | 0.0014 (11) | −0.0069 (12) |
C31 | 0.0280 (14) | 0.0274 (14) | 0.0326 (16) | 0.0091 (12) | 0.0014 (12) | −0.0027 (12) |
C32 | 0.0253 (13) | 0.0267 (13) | 0.0283 (14) | 0.0115 (12) | −0.0013 (11) | 0.0016 (11) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.089 (3) | C12—C17 | 1.399 (4) |
Sn1—C2 | 2.100 (3) | C12—C13 | 1.403 (4) |
Sn1—O1 | 2.116 (2) | C13—C14 | 1.385 (4) |
Sn1—O3 | 2.127 (2) | C13—H13 | 0.9500 |
Sn1—O4 | 2.491 (2) | C14—C15 | 1.384 (4) |
Sn1—O2 | 2.544 (2) | C14—H14 | 0.9500 |
Cl1—C9 | 1.743 (3) | C15—C16 | 1.379 (4) |
Cl2—C15 | 1.742 (3) | C16—C17 | 1.379 (4) |
Cl3—C24 | 1.743 (2) | C16—H16 | 0.9500 |
Cl4—C30 | 1.737 (3) | C17—H17 | 0.9500 |
O1—C3 | 1.297 (3) | C18—C19 | 1.487 (3) |
O2—C3 | 1.246 (3) | C19—C20 | 1.348 (3) |
O3—C18 | 1.294 (3) | C19—C21 | 1.495 (3) |
O4—C18 | 1.249 (3) | C20—C27 | 1.463 (3) |
C1—H1A | 0.9800 | C20—H20 | 0.9500 |
C1—H1B | 0.9800 | C21—C26 | 1.389 (4) |
C1—H1C | 0.9800 | C21—C22 | 1.398 (3) |
C2—H2A | 0.9800 | C22—C23 | 1.384 (3) |
C2—H2B | 0.9800 | C22—H22 | 0.9500 |
C2—H2C | 0.9800 | C23—C24 | 1.384 (4) |
C3—C4 | 1.502 (3) | C23—H23 | 0.9500 |
C4—C5 | 1.353 (3) | C24—C25 | 1.389 (4) |
C4—C6 | 1.493 (3) | C25—C26 | 1.386 (3) |
C5—C12 | 1.466 (3) | C25—H25 | 0.9500 |
C5—H5 | 0.9500 | C26—H26 | 0.9500 |
C6—C7 | 1.392 (4) | C27—C28 | 1.396 (4) |
C6—C11 | 1.393 (4) | C27—C32 | 1.404 (3) |
C7—C8 | 1.389 (4) | C28—C29 | 1.387 (4) |
C7—H7 | 0.9500 | C28—H28 | 0.9500 |
C8—C9 | 1.378 (4) | C29—C30 | 1.376 (4) |
C8—H8 | 0.9500 | C29—H29 | 0.9500 |
C9—C10 | 1.379 (4) | C30—C31 | 1.387 (4) |
C10—C11 | 1.390 (4) | C31—C32 | 1.377 (4) |
C10—H10 | 0.9500 | C31—H31 | 0.9500 |
C11—H11 | 0.9500 | C32—H32 | 0.9500 |
C1—Sn1—C2 | 145.77 (11) | C14—C13—C12 | 121.1 (2) |
C1—Sn1—O1 | 101.90 (9) | C14—C13—H13 | 119.5 |
C2—Sn1—O1 | 100.97 (10) | C12—C13—H13 | 119.5 |
C1—Sn1—O3 | 101.12 (9) | C15—C14—C13 | 119.4 (2) |
C2—Sn1—O3 | 106.20 (9) | C15—C14—H14 | 120.3 |
O1—Sn1—O3 | 84.27 (6) | C13—C14—H14 | 120.3 |
C1—Sn1—O4 | 89.28 (9) | C16—C15—C14 | 121.3 (2) |
C2—Sn1—O4 | 89.19 (9) | C16—C15—Cl2 | 119.4 (2) |
O1—Sn1—O4 | 140.23 (6) | C14—C15—Cl2 | 119.3 (2) |
O3—Sn1—O4 | 56.03 (6) | C15—C16—C17 | 118.8 (2) |
C1—Sn1—O2 | 88.61 (9) | C15—C16—H16 | 120.6 |
C2—Sn1—O2 | 83.70 (9) | C17—C16—H16 | 120.6 |
O1—Sn1—O2 | 55.55 (6) | C16—C17—C12 | 122.1 (3) |
O3—Sn1—O2 | 139.83 (6) | C16—C17—H17 | 118.9 |
O4—Sn1—O2 | 164.02 (5) | C12—C17—H17 | 118.9 |
C3—O1—Sn1 | 101.33 (14) | O4—C18—O3 | 119.1 (2) |
C3—O2—Sn1 | 82.90 (14) | O4—C18—C19 | 122.4 (2) |
C18—O3—Sn1 | 100.18 (14) | O3—C18—C19 | 118.5 (2) |
C18—O4—Sn1 | 84.58 (14) | C20—C19—C18 | 116.7 (2) |
Sn1—C1—H1A | 109.5 | C20—C19—C21 | 124.6 (2) |
Sn1—C1—H1B | 109.5 | C18—C19—C21 | 118.7 (2) |
H1A—C1—H1B | 109.5 | C19—C20—C27 | 131.1 (2) |
Sn1—C1—H1C | 109.5 | C19—C20—H20 | 114.4 |
H1A—C1—H1C | 109.5 | C27—C20—H20 | 114.4 |
H1B—C1—H1C | 109.5 | C26—C21—C22 | 118.7 (2) |
Sn1—C2—H2A | 109.5 | C26—C21—C19 | 119.6 (2) |
Sn1—C2—H2B | 109.5 | C22—C21—C19 | 121.7 (2) |
H2A—C2—H2B | 109.5 | C23—C22—C21 | 120.5 (2) |
Sn1—C2—H2C | 109.5 | C23—C22—H22 | 119.8 |
H2A—C2—H2C | 109.5 | C21—C22—H22 | 119.8 |
H2B—C2—H2C | 109.5 | C22—C23—C24 | 119.5 (2) |
O2—C3—O1 | 120.2 (2) | C22—C23—H23 | 120.2 |
O2—C3—C4 | 121.1 (2) | C24—C23—H23 | 120.2 |
O1—C3—C4 | 118.7 (2) | C23—C24—C25 | 121.2 (2) |
C5—C4—C6 | 127.8 (2) | C23—C24—Cl3 | 119.19 (19) |
C5—C4—C3 | 116.8 (2) | C25—C24—Cl3 | 119.6 (2) |
C6—C4—C3 | 115.3 (2) | C26—C25—C24 | 118.4 (2) |
C4—C5—C12 | 131.6 (2) | C26—C25—H25 | 120.8 |
C4—C5—H5 | 114.2 | C24—C25—H25 | 120.8 |
C12—C5—H5 | 114.2 | C25—C26—C21 | 121.6 (2) |
C7—C6—C11 | 118.5 (2) | C25—C26—H26 | 119.2 |
C7—C6—C4 | 119.5 (2) | C21—C26—H26 | 119.2 |
C11—C6—C4 | 122.0 (2) | C28—C27—C32 | 118.0 (2) |
C8—C7—C6 | 121.0 (3) | C28—C27—C20 | 118.0 (2) |
C8—C7—H7 | 119.5 | C32—C27—C20 | 123.7 (2) |
C6—C7—H7 | 119.5 | C29—C28—C27 | 121.1 (2) |
C9—C8—C7 | 119.1 (3) | C29—C28—H28 | 119.4 |
C9—C8—H8 | 120.5 | C27—C28—H28 | 119.4 |
C7—C8—H8 | 120.5 | C30—C29—C28 | 119.4 (2) |
C8—C9—C10 | 121.3 (3) | C30—C29—H29 | 120.3 |
C8—C9—Cl1 | 119.1 (2) | C28—C29—H29 | 120.3 |
C10—C9—Cl1 | 119.6 (2) | C29—C30—C31 | 120.9 (2) |
C9—C10—C11 | 119.2 (3) | C29—C30—Cl4 | 119.9 (2) |
C9—C10—H10 | 120.4 | C31—C30—Cl4 | 119.2 (2) |
C11—C10—H10 | 120.4 | C32—C31—C30 | 119.6 (2) |
C10—C11—C6 | 120.9 (3) | C32—C31—H31 | 120.2 |
C10—C11—H11 | 119.6 | C30—C31—H31 | 120.2 |
C6—C11—H11 | 119.6 | C31—C32—C27 | 121.0 (2) |
C17—C12—C13 | 117.4 (2) | C31—C32—H32 | 119.5 |
C17—C12—C5 | 115.9 (2) | C27—C32—H32 | 119.5 |
C13—C12—C5 | 126.6 (2) | ||
C1—Sn1—O1—C3 | −80.61 (17) | C17—C12—C13—C14 | 1.3 (4) |
C2—Sn1—O1—C3 | 73.75 (17) | C5—C12—C13—C14 | −175.0 (3) |
O3—Sn1—O1—C3 | 179.19 (16) | C12—C13—C14—C15 | −0.2 (4) |
O4—Sn1—O1—C3 | 175.91 (14) | C13—C14—C15—C16 | −0.8 (4) |
O2—Sn1—O1—C3 | −0.68 (14) | C13—C14—C15—Cl2 | 178.7 (2) |
C1—Sn1—O2—C3 | 106.17 (16) | C14—C15—C16—C17 | 0.7 (4) |
C2—Sn1—O2—C3 | −107.24 (17) | Cl2—C15—C16—C17 | −178.9 (2) |
O1—Sn1—O2—C3 | 0.70 (15) | C15—C16—C17—C12 | 0.5 (4) |
O3—Sn1—O2—C3 | 0.49 (19) | C13—C12—C17—C16 | −1.4 (4) |
O4—Sn1—O2—C3 | −171.3 (2) | C5—C12—C17—C16 | 175.2 (3) |
C1—Sn1—O3—C18 | 79.62 (16) | Sn1—O4—C18—O3 | −3.0 (2) |
C2—Sn1—O3—C18 | −79.55 (17) | Sn1—O4—C18—C19 | 176.4 (2) |
O1—Sn1—O3—C18 | −179.34 (15) | Sn1—O3—C18—O4 | 3.6 (3) |
O4—Sn1—O3—C18 | −1.88 (14) | Sn1—O3—C18—C19 | −175.89 (18) |
O2—Sn1—O3—C18 | −179.18 (13) | O4—C18—C19—C20 | 3.9 (4) |
C1—Sn1—O4—C18 | −102.03 (16) | O3—C18—C19—C20 | −176.7 (2) |
C2—Sn1—O4—C18 | 112.17 (16) | O4—C18—C19—C21 | −173.0 (2) |
O1—Sn1—O4—C18 | 5.87 (19) | O3—C18—C19—C21 | 6.4 (3) |
O3—Sn1—O4—C18 | 1.92 (14) | C18—C19—C20—C27 | 174.8 (3) |
O2—Sn1—O4—C18 | 175.6 (2) | C21—C19—C20—C27 | −8.5 (5) |
Sn1—O2—C3—O1 | −1.1 (2) | C20—C19—C21—C26 | −51.7 (3) |
Sn1—O2—C3—C4 | 177.9 (2) | C18—C19—C21—C26 | 125.0 (3) |
Sn1—O1—C3—O2 | 1.3 (3) | C20—C19—C21—C22 | 129.6 (3) |
Sn1—O1—C3—C4 | −177.67 (19) | C18—C19—C21—C22 | −53.7 (3) |
O2—C3—C4—C5 | 176.0 (2) | C26—C21—C22—C23 | 2.8 (4) |
O1—C3—C4—C5 | −5.1 (4) | C19—C21—C22—C23 | −178.5 (2) |
O2—C3—C4—C6 | −7.6 (4) | C21—C22—C23—C24 | −1.4 (4) |
O1—C3—C4—C6 | 171.3 (2) | C22—C23—C24—C25 | −0.7 (4) |
C6—C4—C5—C12 | −2.9 (5) | C22—C23—C24—Cl3 | 179.58 (19) |
C3—C4—C5—C12 | 173.0 (3) | C23—C24—C25—C26 | 1.1 (4) |
C5—C4—C6—C7 | 107.7 (3) | Cl3—C24—C25—C26 | −179.11 (18) |
C3—C4—C6—C7 | −68.3 (3) | C24—C25—C26—C21 | 0.4 (4) |
C5—C4—C6—C11 | −73.9 (4) | C22—C21—C26—C25 | −2.3 (4) |
C3—C4—C6—C11 | 110.2 (3) | C19—C21—C26—C25 | 178.9 (2) |
C11—C6—C7—C8 | 0.9 (4) | C19—C20—C27—C28 | 159.5 (3) |
C4—C6—C7—C8 | 179.4 (2) | C19—C20—C27—C32 | −26.1 (5) |
C6—C7—C8—C9 | −1.0 (4) | C32—C27—C28—C29 | 0.4 (4) |
C7—C8—C9—C10 | 0.4 (4) | C20—C27—C28—C29 | 175.1 (3) |
C7—C8—C9—Cl1 | −179.3 (2) | C27—C28—C29—C30 | −0.3 (5) |
C8—C9—C10—C11 | 0.3 (4) | C28—C29—C30—C31 | −0.2 (5) |
Cl1—C9—C10—C11 | 179.89 (19) | C28—C29—C30—Cl4 | −178.3 (2) |
C9—C10—C11—C6 | −0.3 (4) | C29—C30—C31—C32 | 0.6 (4) |
C7—C6—C11—C10 | −0.3 (4) | Cl4—C30—C31—C32 | 178.7 (2) |
C4—C6—C11—C10 | −178.7 (2) | C30—C31—C32—C27 | −0.5 (4) |
C4—C5—C12—C17 | −163.1 (3) | C28—C27—C32—C31 | 0.0 (4) |
C4—C5—C12—C13 | 13.2 (5) | C20—C27—C32—C31 | −174.4 (3) |