Acta Cryst. (2011). E67, m74 [ doi:10.1107/S160053681005107X ]
The title compound, [Sn(C10H13)3(C7H4ClO2)], crystallized with two independent molecules per asymmetric unit. In each molecule, the SnIV atom is four-coordinate and possesses a distorted tetrahedral geometry. One of the phenyl rings of one molecule is equally disordered over two positions.
The title compound was synthesized by the reaction of bis[tri(2-phenyl- 2-methylpropyl)tin]oxide (1.05 g, 1 mmol) and 4-chlorobenzoic acid (0.16 g, 1 mmol) in benzene (50 ml). Water was removed with a Dean-Stark trap.The condensation was complete in about 4 h. The resulting clear solution was evaporated under reduced pressure. The white solid obtained was purified by recrystallization from ethanol. The crystals of title compound were obtained from dichloromethane-ethanol(V/V, 1:1) by slow evaporation at 298 K.
One of the phenyl rings (C38-C43) in Molecule B is positionally disordered; occupancies 0.50 (3) / 0.50 (3). Like phenyl ring (C69-C74) they were refined as idealized hexagons. The hydrogen atoms were placed at calculated positions (C–H = 0.93, 0.96 and 0.97 Å, for CH, CH3 and CH2 H-atoms, respectively) and refined as riding with Uiso(H) = k × Ueq(C), where k = 1.5 for CH3 H-atoms, and = 1.2 for all other H-atoms.
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./su2232fig1thm.gif)
| Fig. 1. A view of the molecular structure of the two independent molecules (A and B) of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. |
| [Sn(C10H13)3(C7H4ClO2)] | V = 3405.7 (10) Å3 |
| Mr = 673.85 | Z = 4 |
| Triclinic, P1 | F(000) = 1392 |
| a = 9.948 (2) Å | Dx = 1.314 Mg m−3 |
| b = 18.228 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
| c = 19.039 (3) Å | µ = 0.86 mm−1 |
| α = 84.737 (2)° | T = 296 K |
| β = 82.862 (2)° | Block, colorless |
| γ = 86.127 (2)° | 0.49 × 0.38 × 0.27 mm |
| Bruker APEX CCD area-detector diffractometer | 15434 independent reflections |
| Radiation source: fine-focus sealed tube | 12635 reflections with I > 2σ(I) |
| graphite | Rint = 0.014 |
| φ and ω scans | θmax = 28.8°, θmin = 1.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996)) | h = −13→13 |
| Tmin = 0.677, Tmax = 0.801 | k = −20→24 |
| 21577 measured reflections | l = −18→25 |
| 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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0332P)2 + 0.9695P] where P = (Fo2 + 2Fc2)/3 |
| 15434 reflections | (Δ/σ)max = 0.004 |
| 770 parameters | Δρmax = 0.41 e Å−3 |
| 0 restraints | Δρmin = −0.32 e Å−3 |
| [Sn(C10H13)3(C7H4ClO2)] | γ = 86.127 (2)° |
| Mr = 673.85 | V = 3405.7 (10) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 9.948 (2) Å | Mo Kα radiation |
| b = 18.228 (3) Å | µ = 0.86 mm−1 |
| c = 19.039 (3) Å | T = 296 K |
| α = 84.737 (2)° | 0.49 × 0.38 × 0.27 mm |
| β = 82.862 (2)° |
| Bruker APEX CCD area-detector diffractometer | 15434 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996)) | 12635 reflections with I > 2σ(I) |
| Tmin = 0.677, Tmax = 0.801 | Rint = 0.014 |
| 21577 measured reflections | θmax = 28.8° |
| R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
| wR(F2) = 0.072 | Δρmax = 0.41 e Å−3 |
| S = 1.01 | Δρmin = −0.32 e Å−3 |
| 15434 reflections | Absolute structure: ? |
| 770 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Sn1 | 0.604277 (13) | 0.315748 (7) | 0.287103 (7) | 0.04180 (4) | |
| Cl1 | 0.73721 (8) | 0.62779 (4) | −0.08746 (3) | 0.07544 (18) | |
| O1 | 0.46507 (17) | 0.44265 (10) | 0.21057 (9) | 0.0707 (5) | |
| O2 | 0.66981 (15) | 0.38564 (8) | 0.19820 (8) | 0.0548 (4) | |
| C1 | 0.7017 (3) | 0.01782 (15) | 0.32657 (16) | 0.0816 (8) | |
| H1 | 0.7471 | −0.0196 | 0.3525 | 0.098* | |
| C2 | 0.7492 (3) | 0.03787 (14) | 0.25798 (16) | 0.0737 (7) | |
| H2 | 0.8277 | 0.0141 | 0.2371 | 0.088* | |
| C3 | 0.6821 (2) | 0.09319 (13) | 0.21890 (13) | 0.0586 (6) | |
| H3 | 0.7157 | 0.1057 | 0.1718 | 0.070* | |
| C4 | 0.5656 (2) | 0.13042 (11) | 0.24853 (11) | 0.0451 (4) | |
| C5 | 0.5196 (3) | 0.10867 (13) | 0.31887 (12) | 0.0600 (6) | |
| H5 | 0.4416 | 0.1322 | 0.3406 | 0.072* | |
| C6 | 0.5870 (3) | 0.05312 (15) | 0.35704 (14) | 0.0762 (8) | |
| H6 | 0.5539 | 0.0396 | 0.4040 | 0.091* | |
| C7 | 0.4892 (2) | 0.19172 (12) | 0.20678 (11) | 0.0483 (5) | |
| C8 | 0.3590 (3) | 0.16053 (15) | 0.18770 (15) | 0.0699 (7) | |
| H8A | 0.3102 | 0.1981 | 0.1606 | 0.105* | |
| H8B | 0.3029 | 0.1451 | 0.2305 | 0.105* | |
| H8C | 0.3830 | 0.1191 | 0.1601 | 0.105* | |
| C9 | 0.5728 (3) | 0.21961 (15) | 0.13734 (12) | 0.0652 (6) | |
| H9A | 0.5225 | 0.2594 | 0.1140 | 0.098* | |
| H9B | 0.5915 | 0.1801 | 0.1069 | 0.098* | |
| H9C | 0.6567 | 0.2368 | 0.1478 | 0.098* | |
| C10 | 0.4468 (2) | 0.25806 (11) | 0.25148 (11) | 0.0468 (5) | |
| H10A | 0.3874 | 0.2406 | 0.2931 | 0.056* | |
| H10B | 0.3934 | 0.2936 | 0.2237 | 0.056* | |
| C11 | 0.3907 (6) | 0.1524 (2) | 0.51005 (19) | 0.1123 (15) | |
| H11 | 0.3868 | 0.1043 | 0.5309 | 0.135* | |
| C12 | 0.5056 (4) | 0.18836 (19) | 0.50590 (18) | 0.1009 (11) | |
| H12 | 0.5816 | 0.1650 | 0.5239 | 0.121* | |
| C13 | 0.5110 (3) | 0.26048 (15) | 0.47461 (15) | 0.0729 (7) | |
| H13 | 0.5911 | 0.2846 | 0.4722 | 0.088* | |
| C14 | 0.4011 (2) | 0.29679 (12) | 0.44727 (11) | 0.0484 (5) | |
| C15 | 0.2850 (3) | 0.25851 (17) | 0.45227 (15) | 0.0771 (8) | |
| H15 | 0.2081 | 0.2809 | 0.4344 | 0.092* | |
| C16 | 0.2822 (5) | 0.1866 (2) | 0.4839 (2) | 0.1098 (13) | |
| H16 | 0.2028 | 0.1617 | 0.4869 | 0.132* | |
| C17 | 0.4086 (2) | 0.37643 (12) | 0.41580 (12) | 0.0509 (5) | |
| C18 | 0.3972 (3) | 0.42612 (14) | 0.47749 (15) | 0.0792 (8) | |
| H18A | 0.4038 | 0.4767 | 0.4589 | 0.119* | |
| H18B | 0.4692 | 0.4123 | 0.5061 | 0.119* | |
| H18C | 0.3113 | 0.4204 | 0.5060 | 0.119* | |
| C19 | 0.2935 (3) | 0.40007 (17) | 0.37064 (16) | 0.0782 (8) | |
| H19A | 0.3066 | 0.4490 | 0.3486 | 0.117* | |
| H19B | 0.2082 | 0.3996 | 0.4004 | 0.117* | |
| H19C | 0.2935 | 0.3664 | 0.3347 | 0.117* | |
| C20 | 0.5458 (2) | 0.38822 (12) | 0.36990 (12) | 0.0515 (5) | |
| H20A | 0.6162 | 0.3836 | 0.4013 | 0.062* | |
| H20B | 0.5436 | 0.4385 | 0.3482 | 0.062* | |
| C21 | 0.8805 (3) | 0.3999 (2) | 0.4923 (2) | 0.0913 (10) | |
| H21 | 0.8717 | 0.4261 | 0.5325 | 0.110* | |
| C22 | 0.8680 (3) | 0.3258 (2) | 0.49907 (16) | 0.0895 (9) | |
| H22 | 0.8509 | 0.3011 | 0.5439 | 0.107* | |
| C23 | 0.8808 (3) | 0.28671 (15) | 0.43886 (14) | 0.0681 (7) | |
| H23 | 0.8707 | 0.2361 | 0.4442 | 0.082* | |
| C24 | 0.9080 (2) | 0.32119 (13) | 0.37143 (12) | 0.0508 (5) | |
| C25 | 0.9195 (2) | 0.39718 (14) | 0.36699 (15) | 0.0649 (6) | |
| H25 | 0.9369 | 0.4228 | 0.3226 | 0.078* | |
| C26 | 0.9056 (3) | 0.43545 (17) | 0.4271 (2) | 0.0846 (9) | |
| H26 | 0.9136 | 0.4862 | 0.4226 | 0.102* | |
| C27 | 0.9225 (2) | 0.27742 (13) | 0.30628 (13) | 0.0565 (5) | |
| C28 | 1.0252 (3) | 0.21041 (18) | 0.31650 (19) | 0.0896 (10) | |
| H28A | 1.0357 | 0.1832 | 0.2751 | 0.134* | |
| H28B | 0.9921 | 0.1789 | 0.3573 | 0.134* | |
| H28C | 1.1113 | 0.2276 | 0.3234 | 0.134* | |
| C29 | 0.7861 (2) | 0.24628 (12) | 0.29662 (13) | 0.0537 (5) | |
| H29A | 0.7653 | 0.2102 | 0.3365 | 0.064* | |
| H29B | 0.8021 | 0.2193 | 0.2545 | 0.064* | |
| C30 | 0.9746 (3) | 0.32333 (19) | 0.23819 (15) | 0.0869 (9) | |
| H30A | 0.9818 | 0.2935 | 0.1987 | 0.130* | |
| H30B | 1.0621 | 0.3402 | 0.2428 | 0.130* | |
| H30C | 0.9124 | 0.3650 | 0.2303 | 0.130* | |
| C31 | 0.5783 (2) | 0.43568 (12) | 0.17908 (12) | 0.0509 (5) | |
| C32 | 0.6222 (2) | 0.48453 (11) | 0.11350 (11) | 0.0455 (4) | |
| C33 | 0.5337 (2) | 0.54120 (13) | 0.09034 (13) | 0.0627 (6) | |
| H33 | 0.4493 | 0.5492 | 0.1164 | 0.075* | |
| C34 | 0.5693 (3) | 0.58594 (13) | 0.02913 (14) | 0.0645 (6) | |
| H34 | 0.5100 | 0.6242 | 0.0142 | 0.077* | |
| C35 | 0.6932 (2) | 0.57295 (12) | −0.00921 (11) | 0.0518 (5) | |
| C36 | 0.7831 (2) | 0.51753 (12) | 0.01252 (12) | 0.0557 (5) | |
| H36 | 0.8670 | 0.5096 | −0.0140 | 0.067* | |
| C37 | 0.7472 (2) | 0.47360 (11) | 0.07437 (11) | 0.0507 (5) | |
| H37 | 0.8080 | 0.4363 | 0.0897 | 0.061* | |
| Sn2 | 0.864862 (13) | 0.777477 (7) | 0.166474 (7) | 0.04119 (4) | |
| Cl2 | 1.21565 (12) | 0.98019 (7) | 0.49069 (6) | 0.1369 (4) | |
| O3 | 0.91890 (15) | 0.82223 (8) | 0.25439 (8) | 0.0523 (3) | |
| O4 | 1.02901 (19) | 0.90537 (9) | 0.18023 (9) | 0.0666 (4) | |
| C38 | 1.1546 (9) | 0.5307 (8) | 0.2238 (9) | 0.092 (5) | 0.50 (3) |
| H38 | 1.2373 | 0.5062 | 0.2098 | 0.110* | 0.50 (3) |
| C39 | 1.0408 (13) | 0.5189 (5) | 0.1916 (7) | 0.081 (3) | 0.50 (3) |
| H39 | 1.0474 | 0.4866 | 0.1562 | 0.097* | 0.50 (3) |
| C40 | 0.9171 (10) | 0.5555 (5) | 0.2125 (6) | 0.0628 (19) | 0.50 (3) |
| H40 | 0.8409 | 0.5476 | 0.1910 | 0.075* | 0.50 (3) |
| C41 | 0.9072 (6) | 0.6038 (6) | 0.2655 (7) | 0.049 (2) | 0.50 (3) |
| C42 | 1.0210 (9) | 0.6156 (7) | 0.2977 (7) | 0.071 (2) | 0.50 (3) |
| H42 | 1.0144 | 0.6480 | 0.3331 | 0.085* | 0.50 (3) |
| C43 | 1.1447 (7) | 0.5791 (9) | 0.2768 (9) | 0.094 (5) | 0.50 (3) |
| H43 | 1.2208 | 0.5869 | 0.2983 | 0.113* | 0.50 (3) |
| C38B | 1.1937 (14) | 0.5613 (10) | 0.2515 (7) | 0.092 (5) | 0.50 (3) |
| H38B | 1.2840 | 0.5437 | 0.2451 | 0.110* | 0.50 (3) |
| C39B | 1.1001 (19) | 0.5360 (6) | 0.2123 (6) | 0.090 (5) | 0.50 (3) |
| H39B | 1.1277 | 0.5014 | 0.1797 | 0.108* | 0.50 (3) |
| C40B | 0.9652 (17) | 0.5623 (5) | 0.2220 (5) | 0.068 (3) | 0.50 (3) |
| H40B | 0.9025 | 0.5453 | 0.1958 | 0.081* | 0.50 (3) |
| C41B | 0.9240 (10) | 0.6139 (5) | 0.2708 (6) | 0.048 (2) | 0.50 (3) |
| C42B | 1.0176 (8) | 0.6393 (8) | 0.3100 (5) | 0.065 (2) | 0.50 (3) |
| H42B | 0.9900 | 0.6739 | 0.3426 | 0.078* | 0.50 (3) |
| C43B | 1.1525 (9) | 0.6130 (10) | 0.3003 (6) | 0.097 (3) | 0.50 (3) |
| H43B | 1.2151 | 0.6299 | 0.3266 | 0.117* | 0.50 (3) |
| C44 | 0.7717 (2) | 0.64468 (12) | 0.28278 (12) | 0.0544 (5) | |
| C45 | 0.6689 (3) | 0.58349 (15) | 0.30042 (17) | 0.0876 (9) | |
| H45A | 0.6762 | 0.5526 | 0.2618 | 0.131* | |
| H45B | 0.5785 | 0.6057 | 0.3075 | 0.131* | |
| H45C | 0.6884 | 0.5543 | 0.3429 | 0.131* | |
| C46 | 0.7348 (2) | 0.69228 (13) | 0.21576 (14) | 0.0607 (6) | |
| H46A | 0.6454 | 0.7157 | 0.2277 | 0.073* | |
| H46B | 0.7264 | 0.6588 | 0.1799 | 0.073* | |
| C47 | 0.7527 (3) | 0.69160 (15) | 0.34550 (14) | 0.0841 (9) | |
| H47A | 0.6597 | 0.7098 | 0.3533 | 0.126* | |
| H47B | 0.8101 | 0.7325 | 0.3357 | 0.126* | |
| H47C | 0.7763 | 0.6623 | 0.3872 | 0.126* | |
| C48 | 1.0285 (3) | 0.93124 (17) | −0.08335 (16) | 0.0843 (9) | |
| H48 | 1.0146 | 0.9763 | −0.1093 | 0.101* | |
| C49 | 0.9673 (3) | 0.87071 (18) | −0.09744 (15) | 0.0829 (9) | |
| H49 | 0.9128 | 0.8742 | −0.1340 | 0.100* | |
| C50 | 0.9850 (3) | 0.80381 (15) | −0.05796 (12) | 0.0648 (6) | |
| H50 | 0.9422 | 0.7631 | −0.0686 | 0.078* | |
| C51 | 1.0653 (2) | 0.79638 (11) | −0.00293 (11) | 0.0466 (5) | |
| C52 | 1.1298 (3) | 0.85856 (12) | 0.00955 (13) | 0.0599 (6) | |
| H52 | 1.1862 | 0.8554 | 0.0453 | 0.072* | |
| C53 | 1.1111 (3) | 0.92511 (14) | −0.03039 (16) | 0.0761 (8) | |
| H53 | 1.1550 | 0.9660 | −0.0212 | 0.091* | |
| C54 | 1.0854 (2) | 0.72398 (11) | 0.04284 (11) | 0.0466 (5) | |
| C55 | 0.9899 (3) | 0.66574 (13) | 0.02947 (14) | 0.0616 (6) | |
| H55A | 1.0028 | 0.6224 | 0.0611 | 0.092* | |
| H55B | 1.0095 | 0.6532 | −0.0188 | 0.092* | |
| H55C | 0.8976 | 0.6850 | 0.0376 | 0.092* | |
| C56 | 1.0625 (2) | 0.73692 (12) | 0.12250 (11) | 0.0477 (5) | |
| H56A | 1.1275 | 0.7715 | 0.1310 | 0.057* | |
| H56B | 1.0843 | 0.6906 | 0.1491 | 0.057* | |
| C57 | 1.2327 (2) | 0.69289 (14) | 0.02523 (14) | 0.0640 (6) | |
| H57A | 1.2944 | 0.7281 | 0.0346 | 0.096* | |
| H57B | 1.2484 | 0.6836 | −0.0240 | 0.096* | |
| H57C | 1.2469 | 0.6477 | 0.0541 | 0.096* | |
| C58 | 0.3713 (4) | 0.8062 (3) | 0.2973 (2) | 0.1182 (14) | |
| H58 | 0.3213 | 0.7935 | 0.3408 | 0.142* | |
| C59 | 0.3491 (3) | 0.7741 (2) | 0.2395 (2) | 0.1112 (13) | |
| H59 | 0.2820 | 0.7404 | 0.2429 | 0.133* | |
| C60 | 0.4263 (3) | 0.79108 (19) | 0.17427 (18) | 0.0894 (9) | |
| H60 | 0.4104 | 0.7680 | 0.1347 | 0.107* | |
| C61 | 0.5253 (2) | 0.84136 (14) | 0.16742 (15) | 0.0635 (6) | |
| C62 | 0.5415 (3) | 0.87479 (18) | 0.22809 (18) | 0.0864 (9) | |
| H62 | 0.6051 | 0.9104 | 0.2252 | 0.104* | |
| C63 | 0.4664 (4) | 0.8570 (2) | 0.2926 (2) | 0.1160 (13) | |
| H63 | 0.4809 | 0.8796 | 0.3326 | 0.139* | |
| C64 | 0.6140 (2) | 0.86029 (14) | 0.09763 (14) | 0.0657 (7) | |
| C65 | 0.6132 (3) | 0.8012 (2) | 0.04466 (16) | 0.0994 (11) | |
| H65A | 0.5255 | 0.8027 | 0.0283 | 0.149* | |
| H65B | 0.6329 | 0.7533 | 0.0678 | 0.149* | |
| H65C | 0.6809 | 0.8110 | 0.0049 | 0.149* | |
| C66 | 0.7623 (2) | 0.86803 (12) | 0.11013 (13) | 0.0562 (5) | |
| H66A | 0.7647 | 0.9114 | 0.1358 | 0.067* | |
| H66B | 0.8147 | 0.8776 | 0.0641 | 0.067* | |
| C67 | 0.5596 (3) | 0.9349 (2) | 0.0646 (2) | 0.1180 (14) | |
| H67A | 0.5629 | 0.9722 | 0.0967 | 0.177* | |
| H67B | 0.4675 | 0.9312 | 0.0557 | 0.177* | |
| H67C | 0.6144 | 0.9480 | 0.0206 | 0.177* | |
| C68 | 0.9972 (2) | 0.87762 (11) | 0.23994 (12) | 0.0493 (5) | |
| C69 | 1.04683 (17) | 0.90457 (8) | 0.30302 (7) | 0.0532 (5) | |
| C70 | 1.01267 (16) | 0.87067 (8) | 0.37072 (8) | 0.0631 (6) | |
| H70 | 0.9553 | 0.8318 | 0.3773 | 0.076* | |
| C71 | 1.0643 (2) | 0.89490 (10) | 0.42856 (7) | 0.0785 (8) | |
| H71 | 1.0414 | 0.8722 | 0.4739 | 0.094* | |
| C72 | 1.1501 (2) | 0.95302 (11) | 0.41871 (10) | 0.0818 (9) | |
| C73 | 1.18427 (19) | 0.98692 (9) | 0.35101 (12) | 0.0963 (10) | |
| H73 | 1.2417 | 1.0258 | 0.3444 | 0.116* | |
| C74 | 1.13263 (19) | 0.96270 (9) | 0.29316 (9) | 0.0807 (8) | |
| H74 | 1.1555 | 0.9854 | 0.2479 | 0.097* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.03670 (7) | 0.04200 (8) | 0.04561 (8) | −0.00403 (5) | −0.00482 (5) | 0.00344 (6) |
| Cl1 | 0.0915 (5) | 0.0763 (4) | 0.0553 (3) | −0.0088 (3) | −0.0132 (3) | 0.0210 (3) |
| O1 | 0.0563 (10) | 0.0771 (11) | 0.0692 (11) | 0.0049 (8) | 0.0091 (8) | 0.0164 (9) |
| O2 | 0.0527 (8) | 0.0510 (8) | 0.0558 (9) | −0.0009 (7) | −0.0007 (7) | 0.0117 (7) |
| C1 | 0.103 (2) | 0.0613 (16) | 0.0789 (19) | 0.0170 (15) | −0.0220 (17) | 0.0023 (14) |
| C2 | 0.0795 (18) | 0.0616 (15) | 0.0777 (18) | 0.0185 (13) | −0.0063 (14) | −0.0135 (13) |
| C3 | 0.0654 (14) | 0.0573 (13) | 0.0518 (13) | 0.0030 (11) | −0.0014 (11) | −0.0094 (10) |
| C4 | 0.0473 (11) | 0.0444 (10) | 0.0452 (11) | −0.0073 (8) | −0.0067 (9) | −0.0079 (9) |
| C5 | 0.0613 (14) | 0.0635 (14) | 0.0514 (13) | 0.0002 (11) | 0.0020 (11) | 0.0009 (11) |
| C6 | 0.097 (2) | 0.0717 (17) | 0.0542 (14) | 0.0043 (15) | −0.0057 (14) | 0.0117 (13) |
| C7 | 0.0442 (11) | 0.0582 (12) | 0.0429 (11) | −0.0048 (9) | −0.0071 (8) | −0.0029 (9) |
| C8 | 0.0620 (15) | 0.0800 (17) | 0.0749 (17) | −0.0060 (13) | −0.0244 (13) | −0.0214 (14) |
| C9 | 0.0691 (15) | 0.0804 (17) | 0.0428 (12) | 0.0039 (13) | −0.0037 (11) | 0.0032 (11) |
| C10 | 0.0387 (10) | 0.0514 (11) | 0.0504 (11) | −0.0035 (8) | −0.0068 (9) | −0.0010 (9) |
| C11 | 0.189 (5) | 0.069 (2) | 0.073 (2) | −0.035 (3) | 0.010 (3) | 0.0125 (17) |
| C12 | 0.132 (3) | 0.077 (2) | 0.087 (2) | 0.014 (2) | −0.014 (2) | 0.0174 (18) |
| C13 | 0.0693 (16) | 0.0705 (16) | 0.0755 (18) | −0.0048 (13) | −0.0086 (13) | 0.0132 (14) |
| C14 | 0.0466 (11) | 0.0555 (12) | 0.0418 (11) | −0.0082 (9) | 0.0048 (9) | −0.0061 (9) |
| C15 | 0.0679 (17) | 0.090 (2) | 0.0731 (17) | −0.0314 (15) | 0.0046 (13) | −0.0049 (15) |
| C16 | 0.130 (3) | 0.103 (3) | 0.095 (3) | −0.068 (3) | 0.020 (2) | −0.001 (2) |
| C17 | 0.0491 (12) | 0.0491 (11) | 0.0525 (12) | −0.0009 (9) | 0.0016 (9) | −0.0049 (9) |
| C18 | 0.103 (2) | 0.0593 (15) | 0.0722 (17) | −0.0045 (14) | 0.0114 (15) | −0.0180 (13) |
| C19 | 0.0573 (15) | 0.091 (2) | 0.0809 (19) | 0.0226 (14) | −0.0057 (13) | 0.0009 (15) |
| C20 | 0.0537 (12) | 0.0478 (11) | 0.0526 (12) | −0.0121 (9) | −0.0008 (10) | −0.0018 (9) |
| C21 | 0.074 (2) | 0.116 (3) | 0.089 (2) | −0.0017 (19) | −0.0143 (17) | −0.039 (2) |
| C22 | 0.084 (2) | 0.126 (3) | 0.0592 (17) | −0.0057 (19) | −0.0140 (15) | 0.0006 (18) |
| C23 | 0.0628 (15) | 0.0705 (16) | 0.0704 (17) | −0.0047 (12) | −0.0136 (12) | 0.0058 (13) |
| C24 | 0.0325 (10) | 0.0615 (13) | 0.0593 (13) | −0.0035 (9) | −0.0116 (9) | −0.0008 (10) |
| C25 | 0.0554 (14) | 0.0649 (15) | 0.0751 (17) | −0.0092 (11) | −0.0093 (12) | −0.0037 (13) |
| C26 | 0.0687 (18) | 0.0724 (18) | 0.117 (3) | −0.0072 (14) | −0.0133 (18) | −0.0259 (19) |
| C27 | 0.0374 (11) | 0.0688 (14) | 0.0646 (14) | −0.0027 (10) | −0.0085 (10) | −0.0102 (11) |
| C28 | 0.0515 (15) | 0.104 (2) | 0.120 (3) | 0.0240 (14) | −0.0254 (16) | −0.043 (2) |
| C29 | 0.0440 (11) | 0.0519 (12) | 0.0670 (14) | −0.0028 (9) | −0.0138 (10) | −0.0044 (10) |
| C30 | 0.0629 (16) | 0.131 (3) | 0.0669 (17) | −0.0331 (17) | 0.0078 (13) | −0.0100 (17) |
| C31 | 0.0543 (13) | 0.0457 (11) | 0.0517 (12) | −0.0048 (9) | −0.0060 (10) | 0.0018 (9) |
| C32 | 0.0506 (11) | 0.0412 (10) | 0.0450 (11) | −0.0030 (8) | −0.0080 (9) | −0.0013 (8) |
| C33 | 0.0549 (13) | 0.0612 (14) | 0.0659 (15) | 0.0085 (11) | 0.0015 (11) | 0.0077 (11) |
| C34 | 0.0645 (15) | 0.0567 (13) | 0.0685 (15) | 0.0103 (11) | −0.0124 (12) | 0.0121 (11) |
| C35 | 0.0638 (14) | 0.0476 (11) | 0.0452 (11) | −0.0095 (10) | −0.0131 (10) | 0.0038 (9) |
| C36 | 0.0551 (13) | 0.0568 (13) | 0.0525 (13) | −0.0018 (10) | −0.0025 (10) | 0.0036 (10) |
| C37 | 0.0535 (12) | 0.0448 (11) | 0.0522 (12) | 0.0032 (9) | −0.0073 (10) | 0.0016 (9) |
| Sn2 | 0.04279 (8) | 0.03930 (7) | 0.04131 (7) | −0.00511 (5) | −0.00827 (5) | 0.00398 (5) |
| Cl2 | 0.1463 (9) | 0.1429 (9) | 0.1476 (9) | 0.0149 (7) | −0.0835 (8) | −0.0799 (8) |
| O3 | 0.0610 (9) | 0.0521 (8) | 0.0458 (8) | −0.0142 (7) | −0.0103 (7) | −0.0005 (6) |
| O4 | 0.0869 (12) | 0.0566 (9) | 0.0570 (10) | −0.0177 (8) | −0.0170 (9) | 0.0134 (8) |
| C38 | 0.056 (5) | 0.082 (7) | 0.121 (9) | 0.018 (5) | 0.004 (5) | 0.045 (7) |
| C39 | 0.089 (6) | 0.057 (4) | 0.082 (5) | 0.014 (4) | 0.017 (4) | 0.021 (3) |
| C40 | 0.065 (4) | 0.050 (3) | 0.070 (4) | −0.006 (3) | −0.004 (4) | 0.005 (3) |
| C41 | 0.054 (4) | 0.044 (4) | 0.050 (4) | −0.026 (3) | −0.010 (3) | 0.021 (3) |
| C42 | 0.082 (5) | 0.055 (5) | 0.076 (5) | −0.011 (3) | −0.027 (4) | 0.018 (4) |
| C43 | 0.061 (5) | 0.098 (9) | 0.117 (9) | 0.002 (5) | −0.027 (5) | 0.046 (8) |
| C38B | 0.086 (6) | 0.088 (7) | 0.084 (6) | 0.029 (7) | 0.012 (5) | 0.032 (5) |
| C39B | 0.109 (10) | 0.065 (6) | 0.080 (5) | 0.028 (6) | 0.021 (6) | 0.012 (4) |
| C40B | 0.095 (7) | 0.047 (3) | 0.059 (4) | −0.005 (4) | 0.003 (4) | −0.003 (3) |
| C41B | 0.058 (4) | 0.036 (3) | 0.046 (4) | 0.002 (4) | −0.002 (4) | 0.012 (3) |
| C42B | 0.068 (4) | 0.064 (6) | 0.062 (4) | −0.004 (3) | −0.009 (3) | 0.012 (3) |
| C43B | 0.083 (5) | 0.109 (9) | 0.094 (6) | 0.005 (5) | −0.018 (4) | 0.033 (5) |
| C44 | 0.0599 (13) | 0.0444 (11) | 0.0563 (13) | −0.0136 (10) | −0.0004 (10) | 0.0091 (10) |
| C45 | 0.091 (2) | 0.0698 (17) | 0.099 (2) | −0.0373 (15) | −0.0052 (17) | 0.0250 (16) |
| C46 | 0.0522 (13) | 0.0543 (13) | 0.0747 (16) | −0.0137 (10) | −0.0131 (11) | 0.0144 (11) |
| C47 | 0.120 (2) | 0.0626 (16) | 0.0604 (16) | −0.0126 (16) | 0.0248 (16) | −0.0009 (13) |
| C48 | 0.104 (2) | 0.0670 (18) | 0.0664 (18) | 0.0137 (16) | 0.0183 (16) | 0.0239 (14) |
| C49 | 0.096 (2) | 0.092 (2) | 0.0553 (15) | 0.0049 (17) | −0.0111 (14) | 0.0174 (15) |
| C50 | 0.0762 (16) | 0.0685 (15) | 0.0492 (13) | −0.0085 (12) | −0.0099 (12) | 0.0033 (11) |
| C51 | 0.0498 (11) | 0.0455 (11) | 0.0419 (10) | −0.0027 (9) | 0.0035 (9) | −0.0015 (8) |
| C52 | 0.0678 (15) | 0.0526 (13) | 0.0575 (14) | −0.0125 (11) | 0.0010 (11) | −0.0011 (11) |
| C53 | 0.099 (2) | 0.0473 (13) | 0.0752 (18) | −0.0141 (13) | 0.0203 (16) | −0.0004 (12) |
| C54 | 0.0491 (11) | 0.0420 (10) | 0.0482 (11) | −0.0054 (8) | −0.0044 (9) | −0.0006 (9) |
| C55 | 0.0700 (15) | 0.0491 (12) | 0.0668 (15) | −0.0146 (11) | −0.0055 (12) | −0.0055 (11) |
| C56 | 0.0470 (11) | 0.0488 (11) | 0.0459 (11) | −0.0011 (9) | −0.0074 (9) | 0.0043 (9) |
| C57 | 0.0588 (14) | 0.0598 (14) | 0.0694 (16) | 0.0056 (11) | 0.0039 (12) | −0.0052 (12) |
| C58 | 0.066 (2) | 0.169 (4) | 0.107 (3) | 0.013 (2) | 0.012 (2) | 0.011 (3) |
| C59 | 0.0548 (18) | 0.151 (4) | 0.125 (3) | −0.026 (2) | −0.018 (2) | 0.027 (3) |
| C60 | 0.0628 (17) | 0.115 (3) | 0.093 (2) | −0.0183 (17) | −0.0315 (16) | 0.0139 (19) |
| C61 | 0.0438 (12) | 0.0681 (15) | 0.0785 (17) | 0.0053 (11) | −0.0207 (11) | 0.0067 (13) |
| C62 | 0.080 (2) | 0.085 (2) | 0.092 (2) | 0.0026 (16) | 0.0016 (17) | −0.0195 (17) |
| C63 | 0.105 (3) | 0.136 (3) | 0.103 (3) | 0.006 (3) | 0.017 (2) | −0.036 (3) |
| C64 | 0.0574 (14) | 0.0727 (16) | 0.0669 (15) | −0.0016 (12) | −0.0240 (12) | 0.0164 (13) |
| C65 | 0.091 (2) | 0.148 (3) | 0.0671 (18) | −0.023 (2) | −0.0320 (17) | −0.011 (2) |
| C66 | 0.0546 (13) | 0.0517 (12) | 0.0609 (14) | −0.0042 (10) | −0.0144 (10) | 0.0135 (10) |
| C67 | 0.081 (2) | 0.121 (3) | 0.143 (3) | 0.0079 (19) | −0.040 (2) | 0.068 (2) |
| C68 | 0.0541 (12) | 0.0400 (10) | 0.0541 (12) | 0.0013 (9) | −0.0128 (10) | 0.0007 (9) |
| C69 | 0.0560 (13) | 0.0418 (11) | 0.0643 (14) | 0.0009 (9) | −0.0172 (11) | −0.0057 (10) |
| C70 | 0.0671 (15) | 0.0653 (15) | 0.0605 (14) | −0.0072 (12) | −0.0156 (12) | −0.0107 (12) |
| C71 | 0.089 (2) | 0.087 (2) | 0.0639 (16) | 0.0057 (16) | −0.0214 (15) | −0.0193 (15) |
| C72 | 0.0799 (19) | 0.0754 (18) | 0.102 (2) | 0.0116 (15) | −0.0426 (17) | −0.0402 (17) |
| C73 | 0.104 (2) | 0.0684 (18) | 0.130 (3) | −0.0220 (17) | −0.048 (2) | −0.0192 (19) |
| C74 | 0.094 (2) | 0.0596 (15) | 0.095 (2) | −0.0239 (14) | −0.0317 (17) | 0.0033 (14) |
| Sn1—O2 | 2.0869 (14) | O4—C68 | 1.214 (3) |
| Sn1—C20 | 2.149 (2) | C38—C39 | 1.3900 |
| Sn1—C29 | 2.153 (2) | C38—C43 | 1.3900 |
| Sn1—C10 | 2.153 (2) | C38—H38 | 0.9300 |
| Cl1—C35 | 1.742 (2) | C39—C40 | 1.3900 |
| O1—C31 | 1.213 (3) | C39—H39 | 0.9300 |
| O2—C31 | 1.305 (2) | C40—C41 | 1.3900 |
| C1—C2 | 1.358 (4) | C40—H40 | 0.9300 |
| C1—C6 | 1.363 (4) | C41—C42 | 1.3900 |
| C1—H1 | 0.9300 | C41—C44 | 1.510 (6) |
| C2—C3 | 1.382 (3) | C42—C43 | 1.3900 |
| C2—H2 | 0.9300 | C42—H42 | 0.9300 |
| C3—C4 | 1.387 (3) | C43—H43 | 0.9300 |
| C3—H3 | 0.9300 | C38B—C39B | 1.3900 |
| C4—C5 | 1.391 (3) | C38B—C43B | 1.3900 |
| C4—C7 | 1.527 (3) | C38B—H38B | 0.9300 |
| C5—C6 | 1.377 (3) | C39B—C40B | 1.3900 |
| C5—H5 | 0.9300 | C39B—H39B | 0.9300 |
| C6—H6 | 0.9300 | C40B—C41B | 1.3900 |
| C7—C9 | 1.536 (3) | C40B—H40B | 0.9300 |
| C7—C8 | 1.545 (3) | C41B—C42B | 1.3900 |
| C7—C10 | 1.548 (3) | C41B—C44 | 1.576 (8) |
| C8—H8A | 0.9600 | C42B—C43B | 1.3900 |
| C8—H8B | 0.9600 | C42B—H42B | 0.9300 |
| C8—H8C | 0.9600 | C43B—H43B | 0.9300 |
| C9—H9A | 0.9600 | C44—C47 | 1.518 (3) |
| C9—H9B | 0.9600 | C44—C46 | 1.545 (3) |
| C9—H9C | 0.9600 | C44—C45 | 1.550 (3) |
| C10—H10A | 0.9700 | C45—H45A | 0.9600 |
| C10—H10B | 0.9700 | C45—H45B | 0.9600 |
| C11—C16 | 1.337 (6) | C45—H45C | 0.9600 |
| C11—C12 | 1.346 (5) | C46—H46A | 0.9700 |
| C11—H11 | 0.9300 | C46—H46B | 0.9700 |
| C12—C13 | 1.394 (4) | C47—H47A | 0.9600 |
| C12—H12 | 0.9300 | C47—H47B | 0.9600 |
| C13—C14 | 1.372 (3) | C47—H47C | 0.9600 |
| C13—H13 | 0.9300 | C48—C49 | 1.359 (4) |
| C14—C15 | 1.378 (3) | C48—C53 | 1.370 (4) |
| C14—C17 | 1.522 (3) | C48—H48 | 0.9300 |
| C15—C16 | 1.392 (5) | C49—C50 | 1.385 (4) |
| C15—H15 | 0.9300 | C49—H49 | 0.9300 |
| C16—H16 | 0.9300 | C50—C51 | 1.386 (3) |
| C17—C19 | 1.532 (3) | C50—H50 | 0.9300 |
| C17—C18 | 1.536 (3) | C51—C52 | 1.392 (3) |
| C17—C20 | 1.543 (3) | C51—C54 | 1.529 (3) |
| C18—H18A | 0.9600 | C52—C53 | 1.386 (3) |
| C18—H18B | 0.9600 | C52—H52 | 0.9300 |
| C18—H18C | 0.9600 | C53—H53 | 0.9300 |
| C19—H19A | 0.9600 | C54—C55 | 1.530 (3) |
| C19—H19B | 0.9600 | C54—C56 | 1.543 (3) |
| C19—H19C | 0.9600 | C54—C57 | 1.543 (3) |
| C20—H20A | 0.9700 | C55—H55A | 0.9600 |
| C20—H20B | 0.9700 | C55—H55B | 0.9600 |
| C21—C26 | 1.348 (5) | C55—H55C | 0.9600 |
| C21—C22 | 1.358 (5) | C56—H56A | 0.9700 |
| C21—H21 | 0.9300 | C56—H56B | 0.9700 |
| C22—C23 | 1.392 (4) | C57—H57A | 0.9600 |
| C22—H22 | 0.9300 | C57—H57B | 0.9600 |
| C23—C24 | 1.380 (3) | C57—H57C | 0.9600 |
| C23—H23 | 0.9300 | C58—C59 | 1.340 (6) |
| C24—C25 | 1.392 (3) | C58—C63 | 1.358 (6) |
| C24—C27 | 1.522 (3) | C58—H58 | 0.9300 |
| C25—C26 | 1.382 (4) | C59—C60 | 1.398 (5) |
| C25—H25 | 0.9300 | C59—H59 | 0.9300 |
| C26—H26 | 0.9300 | C60—C61 | 1.377 (4) |
| C27—C30 | 1.530 (4) | C60—H60 | 0.9300 |
| C27—C29 | 1.544 (3) | C61—C62 | 1.386 (4) |
| C27—C28 | 1.553 (3) | C61—C64 | 1.526 (4) |
| C28—H28A | 0.9600 | C62—C63 | 1.379 (5) |
| C28—H28B | 0.9600 | C62—H62 | 0.9300 |
| C28—H28C | 0.9600 | C63—H63 | 0.9300 |
| C29—H29A | 0.9700 | C64—C67 | 1.539 (4) |
| C29—H29B | 0.9700 | C64—C66 | 1.541 (3) |
| C30—H30A | 0.9600 | C64—C65 | 1.542 (4) |
| C30—H30B | 0.9600 | C65—H65A | 0.9600 |
| C30—H30C | 0.9600 | C65—H65B | 0.9600 |
| C31—C32 | 1.502 (3) | C65—H65C | 0.9600 |
| C32—C37 | 1.380 (3) | C66—H66A | 0.9700 |
| C32—C33 | 1.388 (3) | C66—H66B | 0.9700 |
| C33—C34 | 1.382 (3) | C67—H67A | 0.9600 |
| C33—H33 | 0.9300 | C67—H67B | 0.9600 |
| C34—C35 | 1.370 (3) | C67—H67C | 0.9600 |
| C34—H34 | 0.9300 | C68—C69 | 1.489 (2) |
| C35—C36 | 1.373 (3) | C69—C70 | 1.3900 |
| C36—C37 | 1.384 (3) | C69—C74 | 1.3900 |
| C36—H36 | 0.9300 | C70—C71 | 1.3900 |
| C37—H37 | 0.9300 | C70—H70 | 0.9300 |
| Sn2—O3 | 2.0711 (15) | C71—C72 | 1.3900 |
| Sn2—C56 | 2.150 (2) | C71—H71 | 0.9300 |
| Sn2—C66 | 2.153 (2) | C72—C73 | 1.3900 |
| Sn2—C46 | 2.161 (2) | C73—C74 | 1.3900 |
| Cl2—C72 | 1.7144 (14) | C73—H73 | 0.9300 |
| O3—C68 | 1.305 (2) | C74—H74 | 0.9300 |
| O2—Sn1—C20 | 104.55 (7) | C40—C39—H39 | 120.0 |
| O2—Sn1—C29 | 100.11 (8) | C38—C39—H39 | 120.0 |
| C20—Sn1—C29 | 116.27 (9) | C39—C40—C41 | 120.0 |
| O2—Sn1—C10 | 103.32 (7) | C39—C40—H40 | 120.0 |
| C20—Sn1—C10 | 117.51 (8) | C41—C40—H40 | 120.0 |
| C29—Sn1—C10 | 112.11 (8) | C40—C41—C42 | 120.0 |
| C31—O2—Sn1 | 114.39 (13) | C40—C41—C44 | 117.1 (5) |
| C2—C1—C6 | 119.3 (3) | C42—C41—C44 | 122.8 (5) |
| C2—C1—H1 | 120.3 | C43—C42—C41 | 120.0 |
| C6—C1—H1 | 120.3 | C43—C42—H42 | 120.0 |
| C1—C2—C3 | 120.8 (2) | C41—C42—H42 | 120.0 |
| C1—C2—H2 | 119.6 | C42—C43—C38 | 120.0 |
| C3—C2—H2 | 119.6 | C42—C43—H43 | 120.0 |
| C2—C3—C4 | 121.3 (2) | C38—C43—H43 | 120.0 |
| C2—C3—H3 | 119.4 | C39B—C38B—C43B | 120.0 |
| C4—C3—H3 | 119.4 | C39B—C38B—H38B | 120.0 |
| C3—C4—C5 | 116.6 (2) | C43B—C38B—H38B | 120.0 |
| C3—C4—C7 | 122.52 (19) | C40B—C39B—C38B | 120.0 |
| C5—C4—C7 | 120.85 (19) | C40B—C39B—H39B | 120.0 |
| C6—C5—C4 | 121.5 (2) | C38B—C39B—H39B | 120.0 |
| C6—C5—H5 | 119.2 | C41B—C40B—C39B | 120.0 |
| C4—C5—H5 | 119.2 | C41B—C40B—H40B | 120.0 |
| C1—C6—C5 | 120.5 (3) | C39B—C40B—H40B | 120.0 |
| C1—C6—H6 | 119.7 | C42B—C41B—C40B | 120.0 |
| C5—C6—H6 | 119.7 | C42B—C41B—C44 | 118.9 (5) |
| C4—C7—C9 | 112.39 (18) | C40B—C41B—C44 | 121.1 (5) |
| C4—C7—C8 | 108.18 (19) | C43B—C42B—C41B | 120.0 |
| C9—C7—C8 | 108.05 (19) | C43B—C42B—H42B | 120.0 |
| C4—C7—C10 | 111.39 (17) | C41B—C42B—H42B | 120.0 |
| C9—C7—C10 | 108.58 (18) | C42B—C43B—C38B | 120.0 |
| C8—C7—C10 | 108.11 (17) | C42B—C43B—H43B | 120.0 |
| C7—C8—H8A | 109.5 | C38B—C43B—H43B | 120.0 |
| C7—C8—H8B | 109.5 | C41—C44—C47 | 118.6 (5) |
| H8A—C8—H8B | 109.5 | C41—C44—C46 | 109.1 (5) |
| C7—C8—H8C | 109.5 | C47—C44—C46 | 109.3 (2) |
| H8A—C8—H8C | 109.5 | C41—C44—C45 | 104.9 (4) |
| H8B—C8—H8C | 109.5 | C47—C44—C45 | 106.3 (2) |
| C7—C9—H9A | 109.5 | C46—C44—C45 | 108.2 (2) |
| C7—C9—H9B | 109.5 | C41—C44—C41B | 10.5 (5) |
| H9A—C9—H9B | 109.5 | C47—C44—C41B | 109.3 (4) |
| C7—C9—H9C | 109.5 | C46—C44—C41B | 109.9 (5) |
| H9A—C9—H9C | 109.5 | C45—C44—C41B | 113.6 (5) |
| H9B—C9—H9C | 109.5 | C44—C45—H45A | 109.5 |
| C7—C10—Sn1 | 118.18 (13) | C44—C45—H45B | 109.5 |
| C7—C10—H10A | 107.8 | H45A—C45—H45B | 109.5 |
| Sn1—C10—H10A | 107.8 | C44—C45—H45C | 109.5 |
| C7—C10—H10B | 107.8 | H45A—C45—H45C | 109.5 |
| Sn1—C10—H10B | 107.8 | H45B—C45—H45C | 109.5 |
| H10A—C10—H10B | 107.1 | C44—C46—Sn2 | 120.39 (15) |
| C16—C11—C12 | 119.4 (3) | C44—C46—H46A | 107.2 |
| C16—C11—H11 | 120.3 | Sn2—C46—H46A | 107.2 |
| C12—C11—H11 | 120.3 | C44—C46—H46B | 107.2 |
| C11—C12—C13 | 120.1 (4) | Sn2—C46—H46B | 107.2 |
| C11—C12—H12 | 119.9 | H46A—C46—H46B | 106.9 |
| C13—C12—H12 | 119.9 | C44—C47—H47A | 109.5 |
| C14—C13—C12 | 121.7 (3) | C44—C47—H47B | 109.5 |
| C14—C13—H13 | 119.1 | H47A—C47—H47B | 109.5 |
| C12—C13—H13 | 119.1 | C44—C47—H47C | 109.5 |
| C13—C14—C15 | 116.7 (2) | H47A—C47—H47C | 109.5 |
| C13—C14—C17 | 120.5 (2) | H47B—C47—H47C | 109.5 |
| C15—C14—C17 | 122.7 (2) | C49—C48—C53 | 119.2 (3) |
| C14—C15—C16 | 120.4 (3) | C49—C48—H48 | 120.4 |
| C14—C15—H15 | 119.8 | C53—C48—H48 | 120.4 |
| C16—C15—H15 | 119.8 | C48—C49—C50 | 120.8 (3) |
| C11—C16—C15 | 121.6 (3) | C48—C49—H49 | 119.6 |
| C11—C16—H16 | 119.2 | C50—C49—H49 | 119.6 |
| C15—C16—H16 | 119.2 | C49—C50—C51 | 121.3 (3) |
| C14—C17—C19 | 112.3 (2) | C49—C50—H50 | 119.4 |
| C14—C17—C18 | 107.98 (19) | C51—C50—H50 | 119.4 |
| C19—C17—C18 | 108.4 (2) | C50—C51—C52 | 117.0 (2) |
| C14—C17—C20 | 110.80 (17) | C50—C51—C54 | 122.9 (2) |
| C19—C17—C20 | 108.98 (19) | C52—C51—C54 | 120.0 (2) |
| C18—C17—C20 | 108.27 (19) | C53—C52—C51 | 121.1 (3) |
| C17—C18—H18A | 109.5 | C53—C52—H52 | 119.5 |
| C17—C18—H18B | 109.5 | C51—C52—H52 | 119.5 |
| H18A—C18—H18B | 109.5 | C48—C53—C52 | 120.6 (3) |
| C17—C18—H18C | 109.5 | C48—C53—H53 | 119.7 |
| H18A—C18—H18C | 109.5 | C52—C53—H53 | 119.7 |
| H18B—C18—H18C | 109.5 | C51—C54—C55 | 112.55 (19) |
| C17—C19—H19A | 109.5 | C51—C54—C56 | 110.77 (17) |
| C17—C19—H19B | 109.5 | C55—C54—C56 | 108.40 (17) |
| H19A—C19—H19B | 109.5 | C51—C54—C57 | 108.67 (17) |
| C17—C19—H19C | 109.5 | C55—C54—C57 | 108.13 (19) |
| H19A—C19—H19C | 109.5 | C56—C54—C57 | 108.20 (18) |
| H19B—C19—H19C | 109.5 | C54—C55—H55A | 109.5 |
| C17—C20—Sn1 | 117.25 (14) | C54—C55—H55B | 109.5 |
| C17—C20—H20A | 108.0 | H55A—C55—H55B | 109.5 |
| Sn1—C20—H20A | 108.0 | C54—C55—H55C | 109.5 |
| C17—C20—H20B | 108.0 | H55A—C55—H55C | 109.5 |
| Sn1—C20—H20B | 108.0 | H55B—C55—H55C | 109.5 |
| H20A—C20—H20B | 107.2 | C54—C56—Sn2 | 118.35 (14) |
| C26—C21—C22 | 119.8 (3) | C54—C56—H56A | 107.7 |
| C26—C21—H21 | 120.1 | Sn2—C56—H56A | 107.7 |
| C22—C21—H21 | 120.1 | C54—C56—H56B | 107.7 |
| C21—C22—C23 | 120.0 (3) | Sn2—C56—H56B | 107.7 |
| C21—C22—H22 | 120.0 | H56A—C56—H56B | 107.1 |
| C23—C22—H22 | 120.0 | C54—C57—H57A | 109.5 |
| C24—C23—C22 | 121.7 (3) | C54—C57—H57B | 109.5 |
| C24—C23—H23 | 119.1 | H57A—C57—H57B | 109.5 |
| C22—C23—H23 | 119.1 | C54—C57—H57C | 109.5 |
| C23—C24—C25 | 116.3 (2) | H57A—C57—H57C | 109.5 |
| C23—C24—C27 | 120.9 (2) | H57B—C57—H57C | 109.5 |
| C25—C24—C27 | 122.8 (2) | C59—C58—C63 | 120.3 (4) |
| C26—C25—C24 | 121.4 (3) | C59—C58—H58 | 119.8 |
| C26—C25—H25 | 119.3 | C63—C58—H58 | 119.8 |
| C24—C25—H25 | 119.3 | C58—C59—C60 | 120.3 (4) |
| C21—C26—C25 | 120.7 (3) | C58—C59—H59 | 119.9 |
| C21—C26—H26 | 119.7 | C60—C59—H59 | 119.9 |
| C25—C26—H26 | 119.7 | C61—C60—C59 | 121.2 (3) |
| C24—C27—C30 | 112.5 (2) | C61—C60—H60 | 119.4 |
| C24—C27—C29 | 110.85 (18) | C59—C60—H60 | 119.4 |
| C30—C27—C29 | 109.2 (2) | C60—C61—C62 | 116.3 (3) |
| C24—C27—C28 | 109.4 (2) | C60—C61—C64 | 123.0 (3) |
| C30—C27—C28 | 107.7 (2) | C62—C61—C64 | 120.7 (3) |
| C29—C27—C28 | 107.0 (2) | C63—C62—C61 | 122.1 (3) |
| C27—C28—H28A | 109.5 | C63—C62—H62 | 118.9 |
| C27—C28—H28B | 109.5 | C61—C62—H62 | 118.9 |
| H28A—C28—H28B | 109.5 | C58—C63—C62 | 119.6 (4) |
| C27—C28—H28C | 109.5 | C58—C63—H63 | 120.2 |
| H28A—C28—H28C | 109.5 | C62—C63—H63 | 120.2 |
| H28B—C28—H28C | 109.5 | C61—C64—C67 | 108.2 (2) |
| C27—C29—Sn1 | 122.42 (15) | C61—C64—C66 | 111.2 (2) |
| C27—C29—H29A | 106.7 | C67—C64—C66 | 108.1 (2) |
| Sn1—C29—H29A | 106.7 | C61—C64—C65 | 112.2 (2) |
| C27—C29—H29B | 106.7 | C67—C64—C65 | 109.2 (3) |
| Sn1—C29—H29B | 106.7 | C66—C64—C65 | 107.9 (2) |
| H29A—C29—H29B | 106.6 | C64—C65—H65A | 109.5 |
| C27—C30—H30A | 109.5 | C64—C65—H65B | 109.5 |
| C27—C30—H30B | 109.5 | H65A—C65—H65B | 109.5 |
| H30A—C30—H30B | 109.5 | C64—C65—H65C | 109.5 |
| C27—C30—H30C | 109.5 | H65A—C65—H65C | 109.5 |
| H30A—C30—H30C | 109.5 | H65B—C65—H65C | 109.5 |
| H30B—C30—H30C | 109.5 | C64—C66—Sn2 | 118.38 (15) |
| O1—C31—O2 | 123.5 (2) | C64—C66—H66A | 107.7 |
| O1—C31—C32 | 121.4 (2) | Sn2—C66—H66A | 107.7 |
| O2—C31—C32 | 115.01 (18) | C64—C66—H66B | 107.7 |
| C37—C32—C33 | 118.80 (19) | Sn2—C66—H66B | 107.7 |
| C37—C32—C31 | 121.85 (19) | H66A—C66—H66B | 107.1 |
| C33—C32—C31 | 119.33 (19) | C64—C67—H67A | 109.5 |
| C34—C33—C32 | 120.9 (2) | C64—C67—H67B | 109.5 |
| C34—C33—H33 | 119.5 | H67A—C67—H67B | 109.5 |
| C32—C33—H33 | 119.5 | C64—C67—H67C | 109.5 |
| C35—C34—C33 | 118.9 (2) | H67A—C67—H67C | 109.5 |
| C35—C34—H34 | 120.5 | H67B—C67—H67C | 109.5 |
| C33—C34—H34 | 120.5 | O4—C68—O3 | 123.7 (2) |
| C34—C35—C36 | 121.5 (2) | O4—C68—C69 | 121.73 (19) |
| C34—C35—Cl1 | 119.21 (17) | O3—C68—C69 | 114.57 (18) |
| C36—C35—Cl1 | 119.31 (18) | C70—C69—C74 | 120.0 |
| C35—C36—C37 | 119.1 (2) | C70—C69—C68 | 120.91 (13) |
| C35—C36—H36 | 120.4 | C74—C69—C68 | 119.04 (13) |
| C37—C36—H36 | 120.4 | C71—C70—C69 | 120.0 |
| C32—C37—C36 | 120.7 (2) | C71—C70—H70 | 120.0 |
| C32—C37—H37 | 119.6 | C69—C70—H70 | 120.0 |
| C36—C37—H37 | 119.6 | C72—C71—C70 | 120.0 |
| O3—Sn2—C56 | 98.90 (7) | C72—C71—H71 | 120.0 |
| O3—Sn2—C66 | 104.34 (8) | C70—C71—H71 | 120.0 |
| C56—Sn2—C66 | 119.33 (8) | C71—C72—C73 | 120.0 |
| O3—Sn2—C46 | 101.53 (8) | C71—C72—Cl2 | 118.97 (14) |
| C56—Sn2—C46 | 114.20 (9) | C73—C72—Cl2 | 121.01 (14) |
| C66—Sn2—C46 | 114.63 (9) | C74—C73—C72 | 120.0 |
| C68—O3—Sn2 | 114.93 (13) | C74—C73—H73 | 120.0 |
| C39—C38—C43 | 120.0 | C72—C73—H73 | 120.0 |
| C39—C38—H38 | 120.0 | C73—C74—C69 | 120.0 |
| C43—C38—H38 | 120.0 | C73—C74—H74 | 120.0 |
| C40—C39—C38 | 120.0 | C69—C74—H74 | 120.0 |
| C20—Sn1—O2—C31 | −59.08 (17) | C39—C38—C43—C42 | 0.0 |
| C29—Sn1—O2—C31 | −179.79 (15) | C43B—C38B—C39B—C40B | 0.0 |
| C10—Sn1—O2—C31 | 64.41 (16) | C38B—C39B—C40B—C41B | 0.0 |
| C6—C1—C2—C3 | −0.3 (5) | C39B—C40B—C41B—C42B | 0.0 |
| C1—C2—C3—C4 | 0.7 (4) | C39B—C40B—C41B—C44 | −180.0 (9) |
| C2—C3—C4—C5 | −0.7 (3) | C40B—C41B—C42B—C43B | 0.0 |
| C2—C3—C4—C7 | −180.0 (2) | C44—C41B—C42B—C43B | 180.0 (9) |
| C3—C4—C5—C6 | 0.2 (4) | C41B—C42B—C43B—C38B | 0.0 |
| C7—C4—C5—C6 | 179.6 (2) | C39B—C38B—C43B—C42B | 0.0 |
| C2—C1—C6—C5 | −0.1 (5) | C40—C41—C44—C47 | 173.6 (4) |
| C4—C5—C6—C1 | 0.1 (4) | C42—C41—C44—C47 | −9.7 (9) |
| C3—C4—C7—C9 | −14.2 (3) | C40—C41—C44—C46 | −60.5 (6) |
| C5—C4—C7—C9 | 166.5 (2) | C42—C41—C44—C46 | 116.2 (6) |
| C3—C4—C7—C8 | 105.0 (2) | C40—C41—C44—C45 | 55.2 (6) |
| C5—C4—C7—C8 | −74.2 (3) | C42—C41—C44—C45 | −128.0 (6) |
| C3—C4—C7—C10 | −136.3 (2) | C40—C41—C44—C41B | −157 (5) |
| C5—C4—C7—C10 | 44.4 (3) | C42—C41—C44—C41B | 20 (5) |
| C4—C7—C10—Sn1 | 61.6 (2) | C42B—C41B—C44—C41 | −161 (5) |
| C9—C7—C10—Sn1 | −62.7 (2) | C40B—C41B—C44—C41 | 19 (5) |
| C8—C7—C10—Sn1 | −179.66 (16) | C42B—C41B—C44—C47 | −7.6 (6) |
| O2—Sn1—C10—C7 | 80.87 (16) | C40B—C41B—C44—C47 | 172.4 (5) |
| C20—Sn1—C10—C7 | −164.65 (14) | C42B—C41B—C44—C46 | 112.4 (5) |
| C29—Sn1—C10—C7 | −26.05 (18) | C40B—C41B—C44—C46 | −67.7 (7) |
| C16—C11—C12—C13 | 0.0 (6) | C42B—C41B—C44—C45 | −126.2 (4) |
| C11—C12—C13—C14 | −0.1 (5) | C40B—C41B—C44—C45 | 53.8 (7) |
| C12—C13—C14—C15 | 0.0 (4) | C41—C44—C46—Sn2 | −60.3 (5) |
| C12—C13—C14—C17 | 177.8 (3) | C47—C44—C46—Sn2 | 70.8 (3) |
| C13—C14—C15—C16 | 0.1 (4) | C45—C44—C46—Sn2 | −173.79 (19) |
| C17—C14—C15—C16 | −177.7 (3) | C41B—C44—C46—Sn2 | −49.2 (5) |
| C12—C11—C16—C15 | 0.1 (6) | O3—Sn2—C46—C44 | −40.3 (2) |
| C14—C15—C16—C11 | −0.1 (5) | C56—Sn2—C46—C44 | 65.0 (2) |
| C13—C14—C17—C19 | 164.4 (2) | C66—Sn2—C46—C44 | −152.14 (18) |
| C15—C14—C17—C19 | −18.0 (3) | C53—C48—C49—C50 | 1.5 (4) |
| C13—C14—C17—C18 | −76.2 (3) | C48—C49—C50—C51 | 0.1 (4) |
| C15—C14—C17—C18 | 101.5 (3) | C49—C50—C51—C52 | −1.6 (4) |
| C13—C14—C17—C20 | 42.2 (3) | C49—C50—C51—C54 | 178.8 (2) |
| C15—C14—C17—C20 | −140.1 (2) | C50—C51—C52—C53 | 1.6 (3) |
| C14—C17—C20—Sn1 | 53.8 (2) | C54—C51—C52—C53 | −178.8 (2) |
| C19—C17—C20—Sn1 | −70.3 (2) | C49—C48—C53—C52 | −1.5 (4) |
| C18—C17—C20—Sn1 | 172.01 (16) | C51—C52—C53—C48 | −0.1 (4) |
| O2—Sn1—C20—C17 | 133.45 (16) | C50—C51—C54—C55 | −9.5 (3) |
| C29—Sn1—C20—C17 | −117.26 (17) | C52—C51—C54—C55 | 170.8 (2) |
| C10—Sn1—C20—C17 | 19.6 (2) | C50—C51—C54—C56 | −131.1 (2) |
| C26—C21—C22—C23 | −0.2 (5) | C52—C51—C54—C56 | 49.3 (3) |
| C21—C22—C23—C24 | 0.9 (4) | C50—C51—C54—C57 | 110.2 (2) |
| C22—C23—C24—C25 | −1.1 (4) | C52—C51—C54—C57 | −69.4 (3) |
| C22—C23—C24—C27 | 179.6 (2) | C51—C54—C56—Sn2 | 62.7 (2) |
| C23—C24—C25—C26 | 0.6 (3) | C55—C54—C56—Sn2 | −61.3 (2) |
| C27—C24—C25—C26 | 179.9 (2) | C57—C54—C56—Sn2 | −178.29 (14) |
| C22—C21—C26—C25 | −0.3 (5) | O3—Sn2—C56—C54 | −157.89 (15) |
| C24—C25—C26—C21 | 0.1 (4) | C66—Sn2—C56—C54 | −45.84 (19) |
| C23—C24—C27—C30 | −170.9 (2) | C46—Sn2—C56—C54 | 95.12 (16) |
| C25—C24—C27—C30 | 9.9 (3) | C63—C58—C59—C60 | 1.8 (6) |
| C23—C24—C27—C29 | 66.5 (3) | C58—C59—C60—C61 | −0.7 (6) |
| C25—C24—C27—C29 | −112.7 (2) | C59—C60—C61—C62 | −1.3 (4) |
| C23—C24—C27—C28 | −51.2 (3) | C59—C60—C61—C64 | 178.6 (3) |
| C25—C24—C27—C28 | 129.6 (2) | C60—C61—C62—C63 | 2.3 (5) |
| C24—C27—C29—Sn1 | 56.8 (3) | C64—C61—C62—C63 | −177.6 (3) |
| C30—C27—C29—Sn1 | −67.7 (3) | C59—C58—C63—C62 | −0.8 (6) |
| C28—C27—C29—Sn1 | 175.97 (18) | C61—C62—C63—C58 | −1.3 (6) |
| O2—Sn1—C29—C27 | 58.4 (2) | C60—C61—C64—C67 | 102.1 (3) |
| C20—Sn1—C29—C27 | −53.5 (2) | C62—C61—C64—C67 | −77.9 (3) |
| C10—Sn1—C29—C27 | 167.32 (17) | C60—C61—C64—C66 | −139.3 (3) |
| Sn1—O2—C31—O1 | 1.4 (3) | C62—C61—C64—C66 | 40.6 (3) |
| Sn1—O2—C31—C32 | −177.74 (14) | C60—C61—C64—C65 | −18.4 (3) |
| O1—C31—C32—C37 | −175.2 (2) | C62—C61—C64—C65 | 161.6 (3) |
| O2—C31—C32—C37 | 4.0 (3) | C61—C64—C66—Sn2 | 54.9 (3) |
| O1—C31—C32—C33 | 3.2 (3) | C67—C64—C66—Sn2 | 173.4 (2) |
| O2—C31—C32—C33 | −177.7 (2) | C65—C64—C66—Sn2 | −68.5 (3) |
| C37—C32—C33—C34 | 0.2 (4) | O3—Sn2—C66—C64 | −120.47 (19) |
| C31—C32—C33—C34 | −178.2 (2) | C56—Sn2—C66—C64 | 130.46 (19) |
| C32—C33—C34—C35 | 0.9 (4) | C46—Sn2—C66—C64 | −10.3 (2) |
| C33—C34—C35—C36 | −1.2 (4) | Sn2—O3—C68—O4 | 5.3 (3) |
| C33—C34—C35—Cl1 | 178.6 (2) | Sn2—O3—C68—C69 | −174.14 (12) |
| C34—C35—C36—C37 | 0.4 (4) | O4—C68—C69—C70 | −178.03 (17) |
| Cl1—C35—C36—C37 | −179.38 (18) | O3—C68—C69—C70 | 1.5 (2) |
| C33—C32—C37—C36 | −1.0 (3) | O4—C68—C69—C74 | −0.5 (3) |
| C31—C32—C37—C36 | 177.4 (2) | O3—C68—C69—C74 | 179.02 (14) |
| C35—C36—C37—C32 | 0.7 (3) | C74—C69—C70—C71 | 0.0 |
| C56—Sn2—O3—C68 | 64.39 (15) | C68—C69—C70—C71 | 177.53 (17) |
| C66—Sn2—O3—C68 | −59.10 (16) | C69—C70—C71—C72 | 0.0 |
| C46—Sn2—O3—C68 | −178.52 (15) | C70—C71—C72—C73 | 0.0 |
| C43—C38—C39—C40 | 0.0 | C70—C71—C72—Cl2 | −178.37 (15) |
| C38—C39—C40—C41 | 0.0 | C71—C72—C73—C74 | 0.0 |
| C39—C40—C41—C42 | 0.0 | Cl2—C72—C73—C74 | 178.34 (15) |
| C39—C40—C41—C44 | 176.9 (9) | C72—C73—C74—C69 | 0.0 |
| C40—C41—C42—C43 | 0.0 | C70—C69—C74—C73 | 0.0 |
| C44—C41—C42—C43 | −176.7 (10) | C68—C69—C74—C73 | −177.58 (16) |
| C41—C42—C43—C38 | 0.0 |
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.
Bomfim, J. A. S., Filgueiras, C. A. L., Howie, R. A., Low, J. N., Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2002). Polyhedron, 21, 1667–1676.
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Several structures of tris(2-methyl-2-phenylpropyl)tin carboxylates have been reported, such as tris(2-methyl-2-phenylpropyl)tin arylcarboxylate with an organogermyl substituent (Fang et al., 2001), acetate (Bomfim et al., 2002), pyridine-3-carboxylate (Tian et al., 2005) and 4-Formyl-2-methoxyphenolato (Dong, 2008). The tin(IV) atoms in these complexes all possess tetrahedral geometry.
In the two independent molecules (A and B) of the title compound, each tin(IV) atom also has a distorted tetrahedral coordination sphere (Fig. 1).
In the title compound, the C–Sn–C angles vary from 112.11 (8)° to 117.51 (8)° in molecule A and from 114.20 (9)° to 119.33 (8)° in molecule B. The O–Sn–C angle ranges from 100.11 (8)° to 104.55 (7)° in molecule A and 98.90 (7)°to 104.34 (8)° in molecule B.
The three Sn–C distances are almost equal [from 2.149 (2) to 2.153 (2) Å in molecule A and 2.150 (2) - 2.161 (2) Å in molecule B]. The Sn–O bond distances [2.0869 (14) and 2.0711 (15) Å in A and B, respectively] are similar to the values found in the carboxylate structures mentioned above.