Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013600/ww6030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013600/ww6030Isup2.hkl |
CCDC reference: 197442
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.008 Å
- Disorder of main residue
- R factor = 0.048
- wR factor = 0.117
- Data-to-parameter ratio = 18.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(10') PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(11C) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(11D) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(35') PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(36C) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(36D) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(10') PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(11C) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(11D) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(35') PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(36C) PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(36D)
12 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
The ligand was prepared by heating equimolar quantities of phthalic anhydride and D-phenylalanine contained in a Pyrex test tube in a paraffin oil bath at 353–358 K. The title compound was prepared by the method reported in the literature (Gielen, El Khloufi, Biesemans, Kayser & Willem, 1993; Gielen, El Khloufi, Biesemans & Willem, 1993). Equimolar amounts of dibutyltin(IV) oxide and phenylalanine were dissolved in a mixture of toluene (150 ml) and ethanol (50 ml). The solution was refluxed for 6 h and the ternary azeotrope water/toluene/ethanol was distilled off with a Dean–Stark funnel. The excess solvent was removed by rotary evaporator. On slow evaporation of the remaining solution at room temperature, crystals were formed which were washed with ethanol. Crystals suitable for X-ray crystallographic study were grown from chloroform.
The C atoms C10, C11, C35 and C36 of the ligands, and C44 and C45 of a butyl group were disordered over two sites with inequivalent site-occupancy factors. The distances N—C and C—C involving these atoms were restrained using the command DFIX in SHELXL97 during the refinements. H atoms were included in the refinements at geometrically idealized positions, with C—H = 0.95–1.00 Å. The isotropic displacement parameters of the H atoms were set equal to 1.2 and 1.5 times the Ueq of the non-methyl and methyl C atoms to which they were bonded, respectively. The final difference map was essentially featureless with some electron density in the vicinity of the Sn atoms.
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: TEXSAN (Molecular Structure Corportaion, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. ORTEPII (Johnson, 1976) drawing of (I, with displacement ellipsoids plotted at the 40% probability level. H atoms have been omitted for clarity. |
[Sn4(C4H9)8(C17H12NO4)4O2] | F(000) = 1092 |
Mr = 2140.76 | Dx = 1.498 Mg m−3 |
Triclinic, P1 | Melting point: 483 K K |
a = 13.0412 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.6473 (3) Å | Cell parameters from 19979 reflections |
c = 15.6097 (5) Å | θ = 1.0–27.4° |
α = 103.5885 (11)° | µ = 1.11 mm−1 |
β = 94.9563 (13)° | T = 120 K |
γ = 115.8557 (17)° | Prismatic, colourless |
V = 2372.76 (11) Å3 | 0.13 × 0.13 × 0.13 mm |
Z = 1 |
Nonius KappaCCD diffractometer | 10658 independent reflections |
Radiation source: fine-focus sealed tube | 8196 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and ϕ scans | θmax = 27.4°, θmin = 3.4° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −16→15 |
Tmin = 0.874, Tmax = 0.874 | k = −17→17 |
19979 measured reflections | l = −20→20 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.042P)2 + 6.64P] where P = (Fo2 + 2Fc2)/3 |
10658 reflections | (Δ/σ)max = 0.001 |
589 parameters | Δρmax = 1.43 e Å−3 |
22 restraints | Δρmin = −1.37 e Å−3 |
[Sn4(C4H9)8(C17H12NO4)4O2] | γ = 115.8557 (17)° |
Mr = 2140.76 | V = 2372.76 (11) Å3 |
Triclinic, P1 | Z = 1 |
a = 13.0412 (3) Å | Mo Kα radiation |
b = 13.6473 (3) Å | µ = 1.11 mm−1 |
c = 15.6097 (5) Å | T = 120 K |
α = 103.5885 (11)° | 0.13 × 0.13 × 0.13 mm |
β = 94.9563 (13)° |
Nonius KappaCCD diffractometer | 10658 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 8196 reflections with I > 2σ(I) |
Tmin = 0.874, Tmax = 0.874 | Rint = 0.032 |
19979 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 22 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.43 e Å−3 |
10658 reflections | Δρmin = −1.37 e Å−3 |
589 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.83863 (2) | 0.35482 (2) | 0.291756 (18) | 0.02523 (9) | |
Sn2 | 1.07690 (2) | 0.43025 (3) | 0.491702 (19) | 0.02761 (9) | |
O1 | 0.6320 (3) | 0.6384 (4) | 0.1757 (3) | 0.0641 (12) | |
O2 | 0.3923 (4) | 0.3612 (4) | 0.2891 (3) | 0.0647 (12) | |
O3 | 0.7769 (3) | 0.4805 (3) | 0.34296 (19) | 0.0314 (7) | |
O4 | 0.6514 (3) | 0.3982 (3) | 0.2102 (2) | 0.0399 (8) | |
O5 | 1.0006 (3) | 0.1057 (3) | 0.0798 (4) | 0.0688 (14) | |
O6 | 0.7571 (5) | −0.0524 (5) | 0.2568 (3) | 0.0782 (16) | |
O7 | 0.9144 (3) | 0.2350 (3) | 0.2654 (2) | 0.0320 (7) | |
O8 | 1.0659 (3) | 0.2866 (3) | 0.3757 (2) | 0.0349 (8) | |
O9 | 0.9430 (2) | 0.4365 (3) | 0.41729 (19) | 0.0296 (7) | |
N1 | 0.5333 (3) | 0.5155 (4) | 0.2559 (3) | 0.0424 (11) | |
N2 | 0.9043 (4) | 0.0346 (3) | 0.1861 (3) | 0.0447 (12) | |
C1 | 0.5439 (4) | 0.5631 (4) | 0.1845 (3) | 0.0402 (12) | |
C2 | 0.4264 (4) | 0.5013 (4) | 0.1240 (3) | 0.0319 (10) | |
C3 | 0.3863 (5) | 0.5134 (5) | 0.0443 (3) | 0.0413 (12) | |
H3 | 0.4356 | 0.5712 | 0.0210 | 0.050* | |
C4 | 0.2710 (5) | 0.4379 (5) | −0.0008 (3) | 0.0478 (14) | |
H4 | 0.2411 | 0.4441 | −0.0559 | 0.057* | |
C5 | 0.1997 (4) | 0.3540 (5) | 0.0337 (4) | 0.0441 (13) | |
H5 | 0.1217 | 0.3031 | 0.0014 | 0.053* | |
C6 | 0.2388 (4) | 0.3422 (4) | 0.1140 (3) | 0.0384 (11) | |
H6 | 0.1893 | 0.2850 | 0.1378 | 0.046* | |
C7 | 0.3538 (4) | 0.4179 (4) | 0.1581 (3) | 0.0312 (10) | |
C8 | 0.4228 (5) | 0.4232 (4) | 0.2418 (3) | 0.0401 (12) | |
C9 | 0.6884 (4) | 0.4674 (4) | 0.2870 (3) | 0.0335 (10) | |
C10 | 0.6557 (7) | 0.5628 (8) | 0.3070 (7) | 0.0272 (17) | 0.362 (9) |
H10 | 0.7106 | 0.6294 | 0.2892 | 0.033* | 0.362 (9) |
C11 | 0.6521 (12) | 0.5994 (9) | 0.4070 (7) | 0.0329 (16) | 0.362 (9) |
H11A | 0.5894 | 0.5345 | 0.4203 | 0.039* | 0.362 (9) |
H11B | 0.7271 | 0.6174 | 0.4443 | 0.039* | 0.362 (9) |
C10' | 0.6204 (5) | 0.5253 (6) | 0.3302 (4) | 0.0272 (17) | 0.64 |
H10' | 0.5784 | 0.4841 | 0.3717 | 0.033* | 0.638 (9) |
C11' | 0.6988 (6) | 0.6518 (6) | 0.3833 (5) | 0.0329 (16) | 0.64 |
H11C | 0.7637 | 0.6591 | 0.4267 | 0.039* | 0.638 (9) |
H11D | 0.7330 | 0.6947 | 0.3411 | 0.039* | 0.638 (9) |
C12 | 0.6311 (4) | 0.7029 (4) | 0.4338 (3) | 0.0392 (12) | |
C13 | 0.6055 (5) | 0.7001 (5) | 0.5179 (3) | 0.0500 (14) | |
H13 | 0.6202 | 0.6511 | 0.5456 | 0.060* | |
C14 | 0.5603 (5) | 0.7646 (6) | 0.5621 (4) | 0.0606 (18) | |
H14 | 0.5454 | 0.7619 | 0.6202 | 0.073* | |
C15 | 0.5367 (6) | 0.8327 (7) | 0.5228 (5) | 0.076 (2) | |
H15 | 0.5028 | 0.8765 | 0.5524 | 0.092* | |
C16 | 0.5621 (6) | 0.8386 (5) | 0.4387 (5) | 0.073 (2) | |
H16 | 0.5475 | 0.8880 | 0.4115 | 0.088* | |
C17 | 0.6082 (5) | 0.7726 (5) | 0.3952 (4) | 0.0475 (13) | |
H17 | 0.6244 | 0.7758 | 0.3375 | 0.057* | |
C18 | 0.9178 (4) | 0.4364 (4) | 0.1963 (3) | 0.0299 (10) | |
H18A | 0.8649 | 0.4608 | 0.1691 | 0.036* | |
H18B | 0.9909 | 0.5065 | 0.2297 | 0.036* | |
C19 | 0.9468 (4) | 0.3672 (4) | 0.1198 (3) | 0.0371 (11) | |
H19A | 0.9880 | 0.4170 | 0.0838 | 0.045* | |
H19B | 1.0010 | 0.3438 | 0.1462 | 0.045* | |
C20 | 0.8415 (4) | 0.2611 (4) | 0.0570 (3) | 0.0377 (11) | |
H20A | 0.8003 | 0.2107 | 0.0927 | 0.045* | |
H20B | 0.8688 | 0.2188 | 0.0123 | 0.045* | |
C21 | 0.7552 (5) | 0.2881 (5) | 0.0067 (4) | 0.0526 (15) | |
H21A | 0.6895 | 0.2167 | −0.0326 | 0.079* | |
H21B | 0.7949 | 0.3364 | −0.0300 | 0.079* | |
H21C | 0.7264 | 0.3285 | 0.0505 | 0.079* | |
C22 | 0.6808 (4) | 0.2132 (4) | 0.2937 (3) | 0.0346 (10) | |
H22A | 0.6998 | 0.1733 | 0.3329 | 0.042* | |
H22B | 0.6301 | 0.2425 | 0.3211 | 0.042* | |
C23 | 0.6124 (4) | 0.1265 (4) | 0.2013 (3) | 0.0349 (11) | |
H23A | 0.6578 | 0.0884 | 0.1769 | 0.042* | |
H23B | 0.6012 | 0.1670 | 0.1592 | 0.042* | |
C24 | 0.4925 (4) | 0.0357 (4) | 0.2065 (4) | 0.0463 (13) | |
H24A | 0.4480 | 0.0746 | 0.2313 | 0.056* | |
H24B | 0.4489 | −0.0145 | 0.1446 | 0.056* | |
C25 | 0.4982 (5) | −0.0377 (5) | 0.2637 (4) | 0.0522 (14) | |
H25A | 0.4189 | −0.0930 | 0.2639 | 0.078* | |
H25B | 0.5395 | 0.0109 | 0.3256 | 0.078* | |
H25C | 0.5400 | −0.0785 | 0.2386 | 0.078* | |
C26 | 0.9141 (4) | 0.0416 (4) | 0.0989 (4) | 0.0385 (12) | |
C27 | 0.7978 (4) | −0.0438 (4) | 0.0408 (3) | 0.0293 (10) | |
C28 | 0.7608 (5) | −0.0749 (5) | −0.0515 (3) | 0.0413 (12) | |
H28 | 0.8116 | −0.0412 | −0.0883 | 0.050* | |
C29 | 0.6454 (5) | −0.1581 (5) | −0.0882 (4) | 0.0536 (17) | |
H29 | 0.6169 | −0.1819 | −0.1515 | 0.064* | |
C30 | 0.5715 (5) | −0.2068 (5) | −0.0352 (4) | 0.0518 (15) | |
H30 | 0.4932 | −0.2633 | −0.0625 | 0.062* | |
C31 | 0.6101 (4) | −0.1741 (4) | 0.0580 (4) | 0.0442 (13) | |
H31 | 0.5598 | −0.2072 | 0.0953 | 0.053* | |
C32 | 0.7242 (4) | −0.0918 (4) | 0.0936 (3) | 0.0315 (10) | |
C33 | 0.7908 (5) | −0.0382 (5) | 0.1891 (3) | 0.0435 (13) | |
C34 | 0.9917 (4) | 0.2186 (4) | 0.3039 (3) | 0.0318 (10) | |
C35 | 0.9684 (8) | 0.0948 (6) | 0.2820 (5) | 0.0270 (17) | 0.428 (9) |
H35 | 0.9213 | 0.0569 | 0.3230 | 0.032* | 0.428 (9) |
C36 | 1.0816 (8) | 0.0857 (7) | 0.2877 (8) | 0.0269 (17) | 0.428 (9) |
H36A | 1.1251 | 0.1200 | 0.2445 | 0.032* | 0.428 (9) |
H36B | 1.1310 | 0.1295 | 0.3492 | 0.032* | 0.428 (9) |
C35' | 1.0132 (6) | 0.1217 (5) | 0.2538 (4) | 0.0270 (17) | 0.57 |
H35' | 1.0781 | 0.1522 | 0.2219 | 0.032* | 0.572 (9) |
C36' | 1.0455 (8) | 0.0661 (6) | 0.3193 (5) | 0.0269 (17) | 0.57 |
H36C | 1.1199 | 0.1228 | 0.3623 | 0.032* | 0.572 (9) |
H36D | 0.9841 | 0.0408 | 0.3542 | 0.032* | 0.572 (9) |
C37 | 1.0579 (4) | −0.0366 (4) | 0.2669 (3) | 0.0418 (13) | |
C38 | 0.9608 (4) | −0.1407 (4) | 0.2563 (3) | 0.0375 (11) | |
H38 | 0.8942 | −0.1414 | 0.2771 | 0.045* | |
C39 | 0.9592 (4) | −0.2434 (4) | 0.2159 (3) | 0.0378 (11) | |
H39 | 0.8922 | −0.3134 | 0.2100 | 0.045* | |
C40 | 1.0536 (5) | −0.2448 (4) | 0.1843 (3) | 0.0399 (12) | |
H40 | 1.0513 | −0.3154 | 0.1555 | 0.048* | |
C41 | 1.1511 (4) | −0.1439 (5) | 0.1947 (3) | 0.0441 (13) | |
H41 | 1.2173 | −0.1443 | 0.1738 | 0.053* | |
C42 | 1.1533 (5) | −0.0399 (5) | 0.2361 (4) | 0.0447 (13) | |
H42 | 1.2214 | 0.0298 | 0.2432 | 0.054* | |
C43 | 1.2339 (5) | 0.5324 (5) | 0.4571 (3) | 0.0428 (12) | |
H43A | 1.2765 | 0.6088 | 0.5027 | 0.051* | |
H43B | 1.2850 | 0.4958 | 0.4534 | 0.051* | |
C44 | 1.1969 (5) | 0.5429 (5) | 0.3630 (4) | 0.0304 (16) | 0.690 (11) |
H44A | 1.1580 | 0.4662 | 0.3176 | 0.036* | 0.690 (11) |
H44B | 1.1404 | 0.5732 | 0.3666 | 0.036* | 0.690 (11) |
C45 | 1.3024 (5) | 0.6218 (6) | 0.3331 (4) | 0.0381 (18) | 0.690 (11) |
H45A | 1.3431 | 0.6978 | 0.3793 | 0.046* | 0.690 (11) |
H45B | 1.3577 | 0.5901 | 0.3272 | 0.046* | 0.690 (11) |
C44' | 1.2717 (12) | 0.5424 (11) | 0.3695 (6) | 0.0304 (16) | 0.31 |
H44C | 1.2346 | 0.4660 | 0.3238 | 0.036* | 0.310 (11) |
H44D | 1.3574 | 0.5736 | 0.3789 | 0.036* | 0.310 (11) |
C45' | 1.2353 (14) | 0.6217 (13) | 0.3366 (7) | 0.0381 (18) | 0.31 |
H45C | 1.2747 | 0.6982 | 0.3822 | 0.046* | 0.310 (11) |
H45D | 1.1501 | 0.5919 | 0.3312 | 0.046* | 0.310 (11) |
C46 | 1.2650 (5) | 0.6342 (5) | 0.2442 (3) | 0.0479 (13) | |
H46A | 1.3333 | 0.6876 | 0.2272 | 0.072* | |
H46B | 1.2086 | 0.6636 | 0.2497 | 0.072* | |
H46C | 1.2287 | 0.5595 | 0.1978 | 0.072* | |
C47 | 0.9960 (4) | 0.2985 (4) | 0.5514 (3) | 0.0353 (11) | |
H47A | 1.0397 | 0.2545 | 0.5492 | 0.042* | |
H47B | 1.0002 | 0.3336 | 0.6156 | 0.042* | |
C48 | 0.8682 (4) | 0.2165 (4) | 0.5045 (3) | 0.0362 (11) | |
H48A | 0.8230 | 0.2592 | 0.5108 | 0.043* | |
H48B | 0.8632 | 0.1857 | 0.4393 | 0.043* | |
C49 | 0.8138 (5) | 0.1172 (4) | 0.5433 (3) | 0.0412 (12) | |
H49A | 0.8328 | 0.1475 | 0.6100 | 0.049* | |
H49B | 0.7278 | 0.0793 | 0.5230 | 0.049* | |
C50 | 0.8561 (5) | 0.0292 (5) | 0.5151 (4) | 0.0451 (12) | |
H50A | 0.8195 | −0.0320 | 0.5424 | 0.068* | |
H50B | 0.9411 | 0.0660 | 0.5355 | 0.068* | |
H50C | 0.8350 | −0.0032 | 0.4492 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02180 (15) | 0.02678 (16) | 0.02023 (15) | 0.01259 (13) | −0.00571 (11) | −0.00337 (12) |
Sn2 | 0.02511 (16) | 0.02775 (17) | 0.02360 (16) | 0.01525 (13) | −0.00731 (12) | −0.00429 (12) |
O1 | 0.033 (2) | 0.061 (3) | 0.061 (3) | 0.005 (2) | 0.0067 (18) | −0.012 (2) |
O2 | 0.106 (4) | 0.056 (3) | 0.041 (2) | 0.048 (3) | 0.001 (2) | 0.014 (2) |
O3 | 0.0308 (16) | 0.0357 (17) | 0.0239 (15) | 0.0209 (14) | −0.0066 (12) | −0.0036 (13) |
O4 | 0.0344 (17) | 0.044 (2) | 0.0308 (17) | 0.0230 (16) | −0.0111 (14) | −0.0088 (15) |
O5 | 0.031 (2) | 0.040 (2) | 0.131 (4) | 0.0120 (18) | 0.007 (2) | 0.031 (3) |
O6 | 0.122 (4) | 0.140 (5) | 0.035 (2) | 0.109 (4) | 0.033 (2) | 0.038 (3) |
O7 | 0.0335 (17) | 0.0356 (18) | 0.0253 (15) | 0.0230 (15) | −0.0064 (13) | −0.0025 (13) |
O8 | 0.0301 (16) | 0.0317 (17) | 0.0320 (17) | 0.0179 (14) | −0.0083 (13) | −0.0105 (14) |
O9 | 0.0265 (15) | 0.0298 (16) | 0.0242 (15) | 0.0165 (13) | −0.0093 (12) | −0.0076 (13) |
N1 | 0.040 (2) | 0.042 (2) | 0.037 (2) | 0.027 (2) | −0.0164 (18) | −0.0095 (19) |
N2 | 0.048 (3) | 0.037 (2) | 0.037 (2) | 0.027 (2) | −0.0215 (19) | −0.0152 (19) |
C1 | 0.025 (2) | 0.042 (3) | 0.042 (3) | 0.017 (2) | 0.001 (2) | −0.007 (2) |
C2 | 0.028 (2) | 0.031 (2) | 0.031 (2) | 0.015 (2) | −0.0021 (18) | 0.0005 (19) |
C3 | 0.048 (3) | 0.042 (3) | 0.032 (2) | 0.020 (3) | 0.005 (2) | 0.012 (2) |
C4 | 0.053 (3) | 0.060 (4) | 0.032 (3) | 0.036 (3) | −0.007 (2) | 0.004 (3) |
C5 | 0.029 (2) | 0.047 (3) | 0.042 (3) | 0.020 (2) | −0.012 (2) | −0.006 (2) |
C6 | 0.032 (2) | 0.032 (3) | 0.043 (3) | 0.013 (2) | 0.005 (2) | 0.001 (2) |
C7 | 0.030 (2) | 0.031 (2) | 0.032 (2) | 0.017 (2) | −0.0014 (19) | 0.0042 (19) |
C8 | 0.051 (3) | 0.039 (3) | 0.032 (3) | 0.030 (3) | −0.004 (2) | 0.001 (2) |
C9 | 0.025 (2) | 0.037 (3) | 0.032 (2) | 0.014 (2) | −0.0087 (18) | 0.004 (2) |
C10 | 0.031 (4) | 0.031 (4) | 0.022 (3) | 0.020 (3) | −0.001 (3) | 0.003 (3) |
C11 | 0.028 (4) | 0.031 (4) | 0.032 (4) | 0.014 (3) | −0.002 (3) | 0.000 (3) |
C10' | 0.031 (4) | 0.031 (4) | 0.022 (3) | 0.020 (3) | −0.001 (3) | 0.003 (3) |
C11' | 0.028 (4) | 0.031 (4) | 0.032 (4) | 0.014 (3) | −0.002 (3) | 0.000 (3) |
C12 | 0.035 (3) | 0.044 (3) | 0.033 (2) | 0.023 (2) | −0.003 (2) | −0.004 (2) |
C13 | 0.067 (4) | 0.040 (3) | 0.030 (3) | 0.020 (3) | −0.003 (3) | 0.005 (2) |
C14 | 0.041 (3) | 0.076 (5) | 0.037 (3) | 0.012 (3) | 0.007 (2) | −0.002 (3) |
C15 | 0.059 (4) | 0.090 (5) | 0.065 (4) | 0.054 (4) | −0.010 (3) | −0.033 (4) |
C16 | 0.091 (5) | 0.045 (4) | 0.077 (5) | 0.039 (4) | −0.026 (4) | 0.006 (3) |
C17 | 0.048 (3) | 0.047 (3) | 0.036 (3) | 0.013 (3) | 0.002 (2) | 0.012 (2) |
C18 | 0.026 (2) | 0.033 (2) | 0.029 (2) | 0.0147 (19) | 0.0002 (18) | 0.0067 (19) |
C19 | 0.035 (3) | 0.043 (3) | 0.034 (2) | 0.020 (2) | 0.006 (2) | 0.009 (2) |
C20 | 0.042 (3) | 0.037 (3) | 0.027 (2) | 0.019 (2) | 0.003 (2) | −0.001 (2) |
C21 | 0.048 (3) | 0.061 (4) | 0.035 (3) | 0.027 (3) | −0.008 (2) | −0.008 (3) |
C22 | 0.029 (2) | 0.038 (3) | 0.029 (2) | 0.014 (2) | −0.0007 (19) | 0.004 (2) |
C23 | 0.028 (2) | 0.028 (2) | 0.034 (2) | 0.007 (2) | −0.0066 (19) | 0.000 (2) |
C24 | 0.033 (3) | 0.034 (3) | 0.049 (3) | 0.004 (2) | −0.008 (2) | 0.004 (2) |
C25 | 0.042 (3) | 0.044 (3) | 0.063 (4) | 0.015 (3) | 0.008 (3) | 0.015 (3) |
C26 | 0.027 (2) | 0.027 (2) | 0.052 (3) | 0.014 (2) | −0.006 (2) | 0.000 (2) |
C27 | 0.027 (2) | 0.026 (2) | 0.029 (2) | 0.0141 (19) | −0.0041 (18) | −0.0005 (18) |
C28 | 0.053 (3) | 0.053 (3) | 0.028 (2) | 0.035 (3) | 0.008 (2) | 0.011 (2) |
C29 | 0.067 (4) | 0.050 (3) | 0.035 (3) | 0.041 (3) | −0.026 (3) | −0.015 (3) |
C30 | 0.031 (3) | 0.038 (3) | 0.068 (4) | 0.016 (2) | −0.018 (3) | −0.005 (3) |
C31 | 0.031 (3) | 0.034 (3) | 0.065 (4) | 0.015 (2) | 0.007 (2) | 0.013 (3) |
C32 | 0.033 (2) | 0.031 (2) | 0.029 (2) | 0.018 (2) | −0.0008 (19) | 0.0031 (19) |
C33 | 0.066 (4) | 0.055 (3) | 0.027 (2) | 0.046 (3) | 0.005 (2) | 0.009 (2) |
C34 | 0.025 (2) | 0.029 (2) | 0.036 (2) | 0.0165 (19) | −0.0053 (19) | −0.0045 (19) |
C35 | 0.021 (4) | 0.031 (4) | 0.022 (4) | 0.015 (3) | −0.001 (2) | −0.007 (3) |
C36 | 0.032 (5) | 0.026 (3) | 0.018 (4) | 0.013 (3) | −0.003 (3) | 0.003 (3) |
C35' | 0.021 (4) | 0.031 (4) | 0.022 (4) | 0.015 (3) | −0.001 (2) | −0.007 (3) |
C36' | 0.032 (5) | 0.026 (3) | 0.018 (4) | 0.013 (3) | −0.003 (3) | 0.003 (3) |
C37 | 0.045 (3) | 0.032 (3) | 0.039 (3) | 0.023 (2) | −0.020 (2) | −0.003 (2) |
C38 | 0.039 (3) | 0.044 (3) | 0.031 (2) | 0.026 (2) | 0.000 (2) | 0.006 (2) |
C39 | 0.040 (3) | 0.031 (3) | 0.036 (3) | 0.017 (2) | −0.001 (2) | 0.005 (2) |
C40 | 0.048 (3) | 0.039 (3) | 0.030 (2) | 0.025 (3) | −0.001 (2) | −0.001 (2) |
C41 | 0.037 (3) | 0.064 (4) | 0.031 (3) | 0.026 (3) | 0.008 (2) | 0.011 (3) |
C42 | 0.041 (3) | 0.039 (3) | 0.044 (3) | 0.012 (2) | −0.011 (2) | 0.016 (2) |
C43 | 0.049 (3) | 0.039 (3) | 0.035 (3) | 0.020 (2) | 0.010 (2) | 0.002 (2) |
C44 | 0.023 (3) | 0.031 (3) | 0.028 (3) | 0.012 (3) | −0.004 (2) | −0.002 (3) |
C45 | 0.029 (4) | 0.032 (3) | 0.041 (4) | 0.011 (3) | −0.002 (3) | 0.001 (3) |
C44' | 0.023 (3) | 0.031 (3) | 0.028 (3) | 0.012 (3) | −0.004 (2) | −0.002 (3) |
C45' | 0.029 (4) | 0.032 (3) | 0.041 (4) | 0.011 (3) | −0.002 (3) | 0.001 (3) |
C46 | 0.051 (3) | 0.044 (3) | 0.048 (3) | 0.023 (3) | 0.009 (3) | 0.013 (3) |
C47 | 0.038 (3) | 0.033 (3) | 0.026 (2) | 0.016 (2) | −0.0066 (19) | 0.0023 (19) |
C48 | 0.028 (2) | 0.035 (3) | 0.040 (3) | 0.014 (2) | −0.001 (2) | 0.006 (2) |
C49 | 0.041 (3) | 0.044 (3) | 0.035 (3) | 0.017 (2) | 0.007 (2) | 0.011 (2) |
C50 | 0.054 (3) | 0.039 (3) | 0.040 (3) | 0.021 (3) | 0.002 (2) | 0.013 (2) |
Sn1—O9 | 2.031 (3) | C22—H22B | 0.9900 |
Sn1—C22 | 2.131 (5) | C23—C24 | 1.539 (7) |
Sn1—C18 | 2.137 (5) | C23—H23A | 0.9900 |
Sn1—O3 | 2.214 (3) | C23—H23B | 0.9900 |
Sn1—O7 | 2.232 (3) | C24—C25 | 1.509 (8) |
Sn2—O9 | 2.057 (3) | C24—H24A | 0.9900 |
Sn2—C43 | 2.117 (5) | C24—H24B | 0.9900 |
Sn2—C47 | 2.125 (5) | C25—H25A | 0.9800 |
Sn2—O9i | 2.157 (3) | C25—H25B | 0.9800 |
Sn2—O8 | 2.277 (3) | C25—H25C | 0.9800 |
Sn2—O3i | 2.725 (3) | C26—C27 | 1.485 (6) |
O1—C1 | 1.209 (6) | C27—C32 | 1.369 (7) |
O2—C8 | 1.213 (7) | C27—C28 | 1.379 (6) |
O3—C9 | 1.304 (5) | C28—C29 | 1.392 (8) |
O4—C9 | 1.237 (5) | C28—H28 | 0.9500 |
O5—C26 | 1.202 (6) | C29—C30 | 1.375 (9) |
O6—C33 | 1.204 (7) | C29—H29 | 0.9500 |
O7—C34 | 1.258 (5) | C30—C31 | 1.394 (8) |
O8—C34 | 1.263 (5) | C30—H30 | 0.9500 |
O9—Sn2i | 2.157 (3) | C31—C32 | 1.375 (7) |
N1—C8 | 1.394 (7) | C31—H31 | 0.9500 |
N1—C1 | 1.404 (7) | C32—C33 | 1.490 (6) |
N1—C10' | 1.490 (5) | C34—C35' | 1.522 (6) |
N1—C10 | 1.497 (6) | C34—C35 | 1.526 (7) |
N2—C33 | 1.390 (7) | C35—C36 | 1.531 (7) |
N2—C26 | 1.399 (7) | C35—H35 | 1.0000 |
N2—C35' | 1.491 (5) | C36—C37 | 1.506 (7) |
N2—C35 | 1.491 (6) | C36—H36A | 0.9900 |
C1—C2 | 1.483 (6) | C36—H36B | 0.9900 |
C2—C7 | 1.381 (7) | C35'—C36' | 1.539 (7) |
C2—C3 | 1.382 (7) | C35'—H35' | 1.0000 |
C3—C4 | 1.394 (7) | C36'—C37 | 1.530 (6) |
C3—H3 | 0.9500 | C36'—H36C | 0.9900 |
C4—C5 | 1.383 (8) | C36'—H36D | 0.9900 |
C4—H4 | 0.9500 | C37—C42 | 1.386 (8) |
C5—C6 | 1.383 (7) | C37—C38 | 1.390 (7) |
C5—H5 | 0.9500 | C38—C39 | 1.385 (7) |
C6—C7 | 1.388 (6) | C38—H38 | 0.9500 |
C6—H6 | 0.9500 | C39—C40 | 1.371 (7) |
C7—C8 | 1.489 (6) | C39—H39 | 0.9500 |
C9—C10 | 1.514 (7) | C40—C41 | 1.369 (8) |
C9—C10' | 1.527 (6) | C40—H40 | 0.9500 |
C10—C11 | 1.534 (8) | C41—C42 | 1.402 (8) |
C10—H10 | 1.0000 | C41—H41 | 0.9500 |
C11—C12 | 1.525 (7) | C42—H42 | 0.9500 |
C11—H11A | 0.9900 | C43—C44' | 1.509 (7) |
C11—H11B | 0.9900 | C43—C44 | 1.565 (6) |
C10'—C11' | 1.534 (6) | C43—H43A | 0.9900 |
C10'—H10' | 1.0000 | C43—H43B | 0.9900 |
C11'—C12 | 1.513 (6) | C44—C45 | 1.525 (6) |
C11'—H11C | 0.9900 | C44—H44A | 0.9900 |
C11'—H11D | 0.9900 | C44—H44B | 0.9900 |
C12—C17 | 1.357 (7) | C45—C46 | 1.502 (6) |
C12—C13 | 1.387 (7) | C45—H45A | 0.9900 |
C13—C14 | 1.354 (9) | C45—H45B | 0.9900 |
C13—H13 | 0.9500 | C44'—C45' | 1.527 (8) |
C14—C15 | 1.350 (10) | C44'—H44C | 0.9900 |
C14—H14 | 0.9500 | C44'—H44D | 0.9900 |
C15—C16 | 1.393 (11) | C45'—C46 | 1.553 (7) |
C15—H15 | 0.9500 | C45'—H45C | 0.9900 |
C16—C17 | 1.375 (9) | C45'—H45D | 0.9900 |
C16—H16 | 0.9500 | C46—H46A | 0.9800 |
C17—H17 | 0.9500 | C46—H46B | 0.9800 |
C18—C19 | 1.524 (6) | C46—H46C | 0.9800 |
C18—H18A | 0.9900 | C47—C48 | 1.531 (6) |
C18—H18B | 0.9900 | C47—H47A | 0.9900 |
C19—C20 | 1.519 (7) | C47—H47B | 0.9900 |
C19—H19A | 0.9900 | C48—C49 | 1.526 (7) |
C19—H19B | 0.9900 | C48—H48A | 0.9900 |
C20—C21 | 1.538 (7) | C48—H48B | 0.9900 |
C20—H20A | 0.9900 | C49—C50 | 1.521 (7) |
C20—H20B | 0.9900 | C49—H49A | 0.9900 |
C21—H21A | 0.9800 | C49—H49B | 0.9900 |
C21—H21B | 0.9800 | C50—H50A | 0.9800 |
C21—H21C | 0.9800 | C50—H50B | 0.9800 |
C22—C23 | 1.527 (6) | C50—H50C | 0.9800 |
C22—H22A | 0.9900 | ||
O9—Sn1—C22 | 110.61 (15) | C25—C24—C23 | 114.3 (4) |
O9—Sn1—C18 | 111.03 (15) | C25—C24—H24A | 108.7 |
C22—Sn1—C18 | 138.35 (17) | C23—C24—H24A | 108.7 |
O9—Sn1—O3 | 79.76 (11) | C25—C24—H24B | 108.7 |
C22—Sn1—O3 | 93.41 (16) | C23—C24—H24B | 108.7 |
C18—Sn1—O3 | 93.34 (15) | H24A—C24—H24B | 107.6 |
O9—Sn1—O7 | 90.66 (11) | C24—C25—H25A | 109.5 |
C22—Sn1—O7 | 87.22 (16) | C24—C25—H25B | 109.5 |
C18—Sn1—O7 | 92.81 (15) | H25A—C25—H25B | 109.5 |
O3—Sn1—O7 | 169.99 (11) | C24—C25—H25C | 109.5 |
O9—Sn2—C43 | 107.76 (16) | H25A—C25—H25C | 109.5 |
O9—Sn2—C47 | 105.90 (15) | H25B—C25—H25C | 109.5 |
C43—Sn2—C47 | 144.66 (19) | O5—C26—N2 | 124.8 (5) |
O9—Sn2—O9i | 76.86 (11) | O5—C26—C27 | 130.2 (5) |
C43—Sn2—O9i | 99.18 (16) | N2—C26—C27 | 105.0 (4) |
C47—Sn2—O9i | 98.61 (16) | C32—C27—C28 | 121.5 (4) |
O9—Sn2—O8 | 91.08 (11) | C32—C27—C26 | 109.2 (4) |
C43—Sn2—O8 | 84.67 (16) | C28—C27—C26 | 129.3 (5) |
C47—Sn2—O8 | 84.24 (16) | C27—C28—C29 | 116.7 (5) |
O9i—Sn2—O8 | 167.93 (10) | C27—C28—H28 | 121.7 |
O9—Sn2—O3i | 143.48 (10) | C29—C28—H28 | 121.7 |
C43—Sn2—O3i | 81.00 (15) | C30—C29—C28 | 121.9 (5) |
C47—Sn2—O3i | 78.41 (14) | C30—C29—H29 | 119.1 |
O9i—Sn2—O3i | 66.68 (9) | C28—C29—H29 | 119.1 |
O8—Sn2—O3i | 125.36 (10) | C29—C30—C31 | 120.7 (5) |
C9—O3—Sn1 | 113.0 (3) | C29—C30—H30 | 119.6 |
C34—O7—Sn1 | 139.1 (3) | C31—C30—H30 | 119.6 |
C34—O8—Sn2 | 134.8 (3) | C32—C31—C30 | 116.9 (5) |
Sn1—O9—Sn2 | 137.14 (14) | C32—C31—H31 | 121.5 |
Sn1—O9—Sn2i | 119.72 (13) | C30—C31—H31 | 121.5 |
Sn2—O9—Sn2i | 103.14 (11) | C27—C32—C31 | 122.2 (4) |
C8—N1—C1 | 111.6 (4) | C27—C32—C33 | 107.7 (4) |
C8—N1—C10' | 113.8 (5) | C31—C32—C33 | 130.1 (5) |
C1—N1—C10' | 133.0 (5) | O6—C33—N2 | 125.1 (5) |
C8—N1—C10 | 140.4 (6) | O6—C33—C32 | 129.0 (6) |
C1—N1—C10 | 105.2 (6) | N2—C33—C32 | 105.9 (4) |
C33—N2—C26 | 111.9 (4) | O7—C34—O8 | 124.9 (4) |
C33—N2—C35' | 135.9 (5) | O7—C34—C35' | 118.6 (4) |
C26—N2—C35' | 111.3 (5) | O8—C34—C35' | 115.6 (4) |
C33—N2—C35 | 105.7 (5) | O7—C34—C35 | 116.1 (4) |
C26—N2—C35 | 141.1 (6) | O8—C34—C35 | 115.6 (4) |
O1—C1—N1 | 125.9 (5) | N2—C35—C34 | 108.0 (5) |
O1—C1—C2 | 128.3 (5) | N2—C35—C36 | 105.5 (6) |
N1—C1—C2 | 105.8 (4) | C34—C35—C36 | 111.9 (6) |
C7—C2—C3 | 120.8 (4) | N2—C35—H35 | 110.4 |
C7—C2—C1 | 108.4 (4) | C34—C35—H35 | 110.4 |
C3—C2—C1 | 130.8 (5) | C36—C35—H35 | 110.4 |
C2—C3—C4 | 117.8 (5) | C37—C36—C35 | 111.6 (6) |
C2—C3—H3 | 121.1 | C37—C36—H36A | 109.3 |
C4—C3—H3 | 121.1 | C35—C36—H36A | 109.3 |
C5—C4—C3 | 120.7 (5) | C37—C36—H36B | 109.3 |
C5—C4—H4 | 119.7 | C35—C36—H36B | 109.3 |
C3—C4—H4 | 119.7 | H36A—C36—H36B | 108.0 |
C6—C5—C4 | 121.8 (5) | N2—C35'—C34 | 108.2 (4) |
C6—C5—H5 | 119.1 | N2—C35'—C36' | 109.5 (6) |
C4—C5—H5 | 119.1 | C34—C35'—C36' | 111.0 (5) |
C5—C6—C7 | 116.9 (5) | N2—C35'—H35' | 109.3 |
C5—C6—H6 | 121.6 | C34—C35'—H35' | 109.3 |
C7—C6—H6 | 121.6 | C36'—C35'—H35' | 109.3 |
C2—C7—C6 | 122.0 (4) | C37—C36'—C35' | 110.2 (5) |
C2—C7—C8 | 108.2 (4) | C37—C36'—H36C | 109.6 |
C6—C7—C8 | 129.7 (5) | C35'—C36'—H36C | 109.6 |
O2—C8—N1 | 125.7 (5) | C37—C36'—H36D | 109.6 |
O2—C8—C7 | 128.5 (5) | C35'—C36'—H36D | 109.6 |
N1—C8—C7 | 105.8 (4) | H36C—C36'—H36D | 108.1 |
O4—C9—O3 | 122.2 (4) | C42—C37—C38 | 117.3 (4) |
O4—C9—C10 | 118.6 (5) | C42—C37—C36 | 106.0 (6) |
O3—C9—C10 | 116.7 (4) | C38—C37—C36 | 135.4 (6) |
O4—C9—C10' | 122.6 (4) | C42—C37—C36' | 129.5 (6) |
O3—C9—C10' | 114.0 (4) | C38—C37—C36' | 113.1 (6) |
N1—C10—C9 | 107.5 (5) | C39—C38—C37 | 121.3 (5) |
N1—C10—C11 | 105.6 (8) | C39—C38—H38 | 119.4 |
C9—C10—C11 | 110.7 (7) | C37—C38—H38 | 119.4 |
N1—C10—H10 | 110.9 | C40—C39—C38 | 120.5 (5) |
C9—C10—H10 | 110.9 | C40—C39—H39 | 119.7 |
C11—C10—H10 | 110.9 | C38—C39—H39 | 119.7 |
C12—C11—C10 | 113.5 (7) | C41—C40—C39 | 119.7 (5) |
C12—C11—H11A | 108.9 | C41—C40—H40 | 120.2 |
C10—C11—H11A | 108.9 | C39—C40—H40 | 120.2 |
C12—C11—H11B | 108.9 | C40—C41—C42 | 119.9 (5) |
C10—C11—H11B | 108.9 | C40—C41—H41 | 120.1 |
H11A—C11—H11B | 107.7 | C42—C41—H41 | 120.1 |
N1—C10'—C9 | 107.1 (4) | C37—C42—C41 | 121.3 (5) |
N1—C10'—C11' | 109.4 (5) | C37—C42—H42 | 119.3 |
C9—C10'—C11' | 112.8 (5) | C41—C42—H42 | 119.3 |
N1—C10'—H10' | 109.1 | C44'—C43—Sn2 | 134.7 (6) |
C9—C10'—H10' | 109.1 | C44—C43—Sn2 | 105.9 (3) |
C11'—C10'—H10' | 109.1 | C44'—C43—H43A | 108.2 |
C12—C11'—C10' | 111.4 (5) | C44—C43—H43A | 110.6 |
C12—C11'—H11C | 109.4 | Sn2—C43—H43A | 110.6 |
C10'—C11'—H11C | 109.4 | C44'—C43—H43B | 77.3 |
C12—C11'—H11D | 109.4 | C44—C43—H43B | 110.6 |
C10'—C11'—H11D | 109.4 | Sn2—C43—H43B | 110.6 |
H11C—C11'—H11D | 108.0 | H43A—C43—H43B | 108.7 |
C17—C12—C13 | 117.8 (5) | C45—C44—C43 | 111.1 (4) |
C17—C12—C11' | 113.1 (5) | C45—C44—H44A | 109.4 |
C13—C12—C11' | 128.5 (5) | C43—C44—H44A | 109.4 |
C17—C12—C11 | 139.5 (6) | C45—C44—H44B | 109.4 |
C13—C12—C11 | 100.9 (6) | C43—C44—H44B | 109.4 |
C14—C13—C12 | 122.4 (6) | H44A—C44—H44B | 108.0 |
C14—C13—H13 | 118.8 | C46—C45—C44 | 110.4 (5) |
C12—C13—H13 | 118.8 | C46—C45—H45A | 109.6 |
C15—C14—C13 | 119.4 (6) | C44—C45—H45A | 109.6 |
C15—C14—H14 | 120.3 | C46—C45—H45B | 109.6 |
C13—C14—H14 | 120.3 | C44—C45—H45B | 109.6 |
C14—C15—C16 | 119.8 (5) | H45A—C45—H45B | 108.1 |
C14—C15—H15 | 120.1 | C43—C44'—C45' | 108.8 (7) |
C16—C15—H15 | 120.1 | C43—C44'—H44C | 109.9 |
C17—C16—C15 | 119.7 (6) | C45'—C44'—H44C | 109.9 |
C17—C16—H16 | 120.2 | C43—C44'—H44D | 109.9 |
C15—C16—H16 | 120.2 | C45'—C44'—H44D | 109.9 |
C12—C17—C16 | 120.8 (6) | H44C—C44'—H44D | 108.3 |
C12—C17—H17 | 119.6 | C44'—C45'—C46 | 113.3 (8) |
C16—C17—H17 | 119.6 | C44'—C45'—H45C | 108.9 |
C19—C18—Sn1 | 117.4 (3) | C46—C45'—H45C | 108.9 |
C19—C18—H18A | 108.0 | C44'—C45'—H45D | 108.9 |
Sn1—C18—H18A | 108.0 | C46—C45'—H45D | 108.9 |
C19—C18—H18B | 108.0 | H45C—C45'—H45D | 107.7 |
Sn1—C18—H18B | 108.0 | C45—C46—H46A | 109.5 |
H18A—C18—H18B | 107.2 | C45—C46—H46B | 109.5 |
C20—C19—C18 | 114.5 (4) | H46A—C46—H46B | 109.5 |
C20—C19—H19A | 108.6 | C45—C46—H46C | 109.5 |
C18—C19—H19A | 108.6 | C45'—C46—H46C | 110.9 |
C20—C19—H19B | 108.6 | H46A—C46—H46C | 109.5 |
C18—C19—H19B | 108.6 | H46B—C46—H46C | 109.5 |
H19A—C19—H19B | 107.6 | C48—C47—Sn2 | 113.0 (3) |
C19—C20—C21 | 113.2 (4) | C48—C47—H47A | 109.0 |
C19—C20—H20A | 108.9 | Sn2—C47—H47A | 109.0 |
C21—C20—H20A | 108.9 | C48—C47—H47B | 109.0 |
C19—C20—H20B | 108.9 | Sn2—C47—H47B | 109.0 |
C21—C20—H20B | 108.9 | H47A—C47—H47B | 107.8 |
H20A—C20—H20B | 107.8 | C49—C48—C47 | 112.5 (4) |
C20—C21—H21A | 109.5 | C49—C48—H48A | 109.1 |
C20—C21—H21B | 109.5 | C47—C48—H48A | 109.1 |
H21A—C21—H21B | 109.5 | C49—C48—H48B | 109.1 |
C20—C21—H21C | 109.5 | C47—C48—H48B | 109.1 |
H21A—C21—H21C | 109.5 | H48A—C48—H48B | 107.8 |
H21B—C21—H21C | 109.5 | C50—C49—C48 | 112.8 (4) |
C23—C22—Sn1 | 114.8 (3) | C50—C49—H49A | 109.0 |
C23—C22—H22A | 108.6 | C48—C49—H49A | 109.0 |
Sn1—C22—H22A | 108.6 | C50—C49—H49B | 109.0 |
C23—C22—H22B | 108.6 | C48—C49—H49B | 109.0 |
Sn1—C22—H22B | 108.6 | H49A—C49—H49B | 107.8 |
H22A—C22—H22B | 107.5 | C49—C50—H50A | 109.5 |
C22—C23—C24 | 111.7 (4) | C49—C50—H50B | 109.5 |
C22—C23—H23A | 109.3 | H50A—C50—H50B | 109.5 |
C24—C23—H23A | 109.3 | C49—C50—H50C | 109.5 |
C22—C23—H23B | 109.3 | H50A—C50—H50C | 109.5 |
C24—C23—H23B | 109.3 | H50B—C50—H50C | 109.5 |
H23A—C23—H23B | 107.9 | ||
O9—Sn1—O3—C9 | −175.4 (3) | C18—C19—C20—C21 | 62.6 (6) |
C22—Sn1—O3—C9 | −65.0 (3) | O9—Sn1—C22—C23 | −163.3 (3) |
C18—Sn1—O3—C9 | 73.8 (3) | C18—Sn1—C22—C23 | 17.5 (5) |
O7—Sn1—O3—C9 | −158.4 (6) | O3—Sn1—C22—C23 | 116.4 (3) |
O9—Sn1—O7—C34 | −2.8 (5) | O7—Sn1—C22—C23 | −73.6 (3) |
C22—Sn1—O7—C34 | −113.4 (5) | Sn1—C22—C23—C24 | −172.5 (3) |
C18—Sn1—O7—C34 | 108.3 (5) | C22—C23—C24—C25 | −63.1 (6) |
O3—Sn1—O7—C34 | −19.6 (10) | C33—N2—C26—O5 | 173.6 (5) |
O9—Sn2—O8—C34 | −15.1 (5) | C35'—N2—C26—O5 | 3.2 (7) |
C43—Sn2—O8—C34 | −122.8 (5) | C35—N2—C26—O5 | 9.5 (10) |
C47—Sn2—O8—C34 | 90.8 (5) | C33—N2—C26—C27 | −5.9 (5) |
O9i—Sn2—O8—C34 | −13.6 (9) | C35'—N2—C26—C27 | −176.3 (4) |
O3i—Sn2—O8—C34 | 162.1 (4) | C35—N2—C26—C27 | −169.9 (6) |
C22—Sn1—O9—Sn2 | 92.8 (3) | O5—C26—C27—C32 | −176.2 (5) |
C18—Sn1—O9—Sn2 | −87.7 (3) | N2—C26—C27—C32 | 3.2 (5) |
O3—Sn1—O9—Sn2 | −177.4 (3) | O5—C26—C27—C28 | 3.2 (9) |
O7—Sn1—O9—Sn2 | 5.5 (3) | N2—C26—C27—C28 | −177.4 (5) |
C22—Sn1—O9—Sn2i | −87.5 (2) | C32—C27—C28—C29 | −0.5 (7) |
C18—Sn1—O9—Sn2i | 92.0 (2) | C26—C27—C28—C29 | −179.8 (4) |
O3—Sn1—O9—Sn2i | 2.30 (16) | C27—C28—C29—C30 | 0.2 (8) |
O7—Sn1—O9—Sn2i | −174.78 (18) | C28—C29—C30—C31 | 0.0 (8) |
C43—Sn2—O9—Sn1 | 84.1 (3) | C29—C30—C31—C32 | 0.1 (8) |
C47—Sn2—O9—Sn1 | −84.9 (3) | C28—C27—C32—C31 | 0.5 (7) |
O9i—Sn2—O9—Sn1 | 179.7 (3) | C26—C27—C32—C31 | 180.0 (4) |
O8—Sn2—O9—Sn1 | −0.6 (3) | C28—C27—C32—C33 | −179.1 (4) |
O3i—Sn2—O9—Sn1 | −176.85 (16) | C26—C27—C32—C33 | 0.4 (5) |
C43—Sn2—O9—Sn2i | −95.59 (18) | C30—C31—C32—C27 | −0.3 (7) |
C47—Sn2—O9—Sn2i | 95.35 (17) | C30—C31—C32—C33 | 179.2 (5) |
O9i—Sn2—O9—Sn2i | 0.0 | C26—N2—C33—O6 | −174.1 (5) |
O8—Sn2—O9—Sn2i | 179.67 (14) | C35'—N2—C33—O6 | −7.0 (9) |
O3i—Sn2—O9—Sn2i | 3.4 (3) | C35—N2—C33—O6 | −4.4 (7) |
C8—N1—C1—O1 | −174.5 (5) | C26—N2—C33—C32 | 6.1 (5) |
C10'—N1—C1—O1 | −10.7 (8) | C35'—N2—C33—C32 | 173.2 (5) |
C10—N1—C1—O1 | −9.5 (7) | C35—N2—C33—C32 | 175.8 (4) |
C8—N1—C1—C2 | 5.0 (5) | C27—C32—C33—O6 | 176.3 (5) |
C10'—N1—C1—C2 | 168.8 (5) | C31—C32—C33—O6 | −3.2 (9) |
C10—N1—C1—C2 | 169.9 (4) | C27—C32—C33—N2 | −3.8 (5) |
O1—C1—C2—C7 | 176.7 (5) | C31—C32—C33—N2 | 176.6 (5) |
N1—C1—C2—C7 | −2.7 (5) | Sn1—O7—C34—O8 | −9.6 (8) |
O1—C1—C2—C3 | −1.1 (9) | Sn1—O7—C34—C35' | −178.3 (4) |
N1—C1—C2—C3 | 179.5 (5) | Sn1—O7—C34—C35 | 148.4 (5) |
C7—C2—C3—C4 | −0.9 (7) | Sn2—O8—C34—O7 | 21.2 (8) |
C1—C2—C3—C4 | 176.7 (5) | Sn2—O8—C34—C35' | −169.8 (4) |
C2—C3—C4—C5 | 0.2 (8) | Sn2—O8—C34—C35 | −136.9 (5) |
C3—C4—C5—C6 | 0.6 (8) | C33—N2—C35—C34 | −108.3 (6) |
C4—C5—C6—C7 | −0.7 (7) | C26—N2—C35—C34 | 56.4 (10) |
C3—C2—C7—C6 | 0.8 (7) | C35'—N2—C35—C34 | 68.2 (8) |
C1—C2—C7—C6 | −177.2 (4) | C33—N2—C35—C36 | 131.9 (6) |
C3—C2—C7—C8 | 177.7 (4) | C26—N2—C35—C36 | −63.5 (9) |
C1—C2—C7—C8 | −0.3 (5) | C35'—N2—C35—C36 | −51.7 (7) |
C5—C6—C7—C2 | 0.0 (7) | O7—C34—C35—N2 | 34.3 (8) |
C5—C6—C7—C8 | −176.2 (5) | O8—C34—C35—N2 | −165.6 (5) |
C1—N1—C8—O2 | 174.5 (5) | C35'—C34—C35—N2 | −68.2 (7) |
C10'—N1—C8—O2 | 7.4 (7) | O7—C34—C35—C36 | 150.0 (6) |
C10—N1—C8—O2 | 17.7 (11) | O8—C34—C35—C36 | −49.9 (9) |
C1—N1—C8—C7 | −5.2 (5) | C35'—C34—C35—C36 | 47.5 (8) |
C10'—N1—C8—C7 | −172.3 (4) | N2—C35—C36—C37 | −63.3 (9) |
C10—N1—C8—C7 | −162.0 (7) | C34—C35—C36—C37 | 179.5 (6) |
C2—C7—C8—O2 | −176.4 (5) | C33—N2—C35'—C34 | −63.9 (8) |
C6—C7—C8—O2 | 0.2 (9) | C26—N2—C35'—C34 | 103.2 (5) |
C2—C7—C8—N1 | 3.3 (5) | C35—N2—C35'—C34 | −68.8 (7) |
C6—C7—C8—N1 | 179.9 (5) | C33—N2—C35'—C36' | 57.2 (8) |
Sn1—O3—C9—O4 | −6.2 (6) | C26—N2—C35'—C36' | −135.6 (5) |
Sn1—O3—C9—C10 | −168.0 (6) | C35—N2—C35'—C36' | 52.3 (8) |
Sn1—O3—C9—C10' | 161.8 (4) | O7—C34—C35'—N2 | −24.8 (8) |
C8—N1—C10—C9 | 51.0 (12) | O8—C34—C35'—N2 | 165.5 (5) |
C1—N1—C10—C9 | −106.7 (7) | C35—C34—C35'—N2 | 68.4 (7) |
C10'—N1—C10—C9 | 71.5 (8) | O7—C34—C35'—C36' | −145.1 (6) |
C8—N1—C10—C11 | −67.3 (10) | O8—C34—C35'—C36' | 45.2 (8) |
C1—N1—C10—C11 | 135.0 (6) | C35—C34—C35'—C36' | −51.9 (8) |
C10'—N1—C10—C11 | −46.8 (8) | N2—C35'—C36'—C37 | 56.4 (8) |
O4—C9—C10—N1 | 36.1 (10) | C34—C35'—C36'—C37 | 175.9 (5) |
O3—C9—C10—N1 | −161.4 (6) | C35—C36—C37—C42 | 154.9 (7) |
C10'—C9—C10—N1 | −70.3 (8) | C35—C36—C37—C38 | −10.9 (13) |
O4—C9—C10—C11 | 151.0 (7) | C35—C36—C37—C36' | −53.9 (9) |
O3—C9—C10—C11 | −46.5 (10) | C35'—C36'—C37—C42 | 84.4 (8) |
C10'—C9—C10—C11 | 44.6 (9) | C35'—C36'—C37—C38 | −101.1 (7) |
N1—C10—C11—C12 | −69.4 (11) | C35'—C36'—C37—C36 | 47.5 (9) |
C9—C10—C11—C12 | 174.5 (8) | C42—C37—C38—C39 | −0.4 (7) |
C8—N1—C10'—C9 | 96.2 (6) | C36—C37—C38—C39 | 164.2 (8) |
C1—N1—C10'—C9 | −67.4 (7) | C36'—C37—C38—C39 | −175.7 (5) |
C10—N1—C10'—C9 | −69.7 (8) | C37—C38—C39—C40 | −0.7 (7) |
C8—N1—C10'—C11' | −141.3 (5) | C38—C39—C40—C41 | 1.5 (7) |
C1—N1—C10'—C11' | 55.2 (7) | C39—C40—C41—C42 | −1.0 (7) |
C10—N1—C10'—C11' | 52.9 (8) | C38—C37—C42—C41 | 0.9 (7) |
O4—C9—C10'—N1 | −19.3 (8) | C36—C37—C42—C41 | −167.9 (6) |
O3—C9—C10'—N1 | 172.7 (5) | C36'—C37—C42—C41 | 175.2 (5) |
C10—C9—C10'—N1 | 70.6 (7) | C40—C41—C42—C37 | −0.2 (8) |
O4—C9—C10'—C11' | −139.8 (6) | O9—Sn2—C43—C44' | −48.3 (8) |
O3—C9—C10'—C11' | 52.2 (7) | C47—Sn2—C43—C44' | 113.3 (8) |
C10—C9—C10'—C11' | −49.8 (8) | O9i—Sn2—C43—C44' | −127.3 (8) |
N1—C10'—C11'—C12 | 67.3 (7) | O8—Sn2—C43—C44' | 41.1 (8) |
C9—C10'—C11'—C12 | −173.6 (5) | O3i—Sn2—C43—C44' | 168.2 (8) |
C10'—C11'—C12—C17 | −105.4 (6) | O9—Sn2—C43—C44 | −20.8 (4) |
C10'—C11'—C12—C13 | 84.4 (8) | C47—Sn2—C43—C44 | 140.8 (4) |
C10'—C11'—C12—C11 | 41.8 (8) | O9i—Sn2—C43—C44 | −99.9 (3) |
C10—C11—C12—C17 | 4.2 (16) | O8—Sn2—C43—C44 | 68.6 (3) |
C10—C11—C12—C13 | 166.9 (8) | O3i—Sn2—C43—C44 | −164.3 (4) |
C10—C11—C12—C11' | −45.7 (7) | C44'—C43—C44—C45 | −37.0 (9) |
C17—C12—C13—C14 | −0.7 (8) | Sn2—C43—C44—C45 | 176.1 (4) |
C11'—C12—C13—C14 | 169.1 (6) | C43—C44—C45—C46 | −178.0 (5) |
C11—C12—C13—C14 | −168.1 (7) | C44—C43—C44'—C45' | 36.6 (8) |
C12—C13—C14—C15 | 1.4 (9) | Sn2—C43—C44'—C45' | 84.2 (12) |
C13—C14—C15—C16 | −1.9 (10) | C43—C44'—C45'—C46 | −177.5 (9) |
C14—C15—C16—C17 | 1.7 (10) | C44—C45—C46—C45' | 36.4 (10) |
C13—C12—C17—C16 | 0.5 (8) | C44'—C45'—C46—C45 | −36.7 (9) |
C11'—C12—C17—C16 | −170.9 (5) | O9—Sn2—C47—C48 | 18.6 (4) |
C11—C12—C17—C16 | 161.2 (10) | C43—Sn2—C47—C48 | −143.2 (3) |
C15—C16—C17—C12 | −1.0 (10) | O9i—Sn2—C47—C48 | 97.3 (3) |
O9—Sn1—C18—C19 | 117.1 (3) | O8—Sn2—C47—C48 | −70.9 (3) |
C22—Sn1—C18—C19 | −63.7 (4) | O3i—Sn2—C47—C48 | 161.2 (4) |
O3—Sn1—C18—C19 | −162.6 (3) | Sn2—C47—C48—C49 | 175.7 (3) |
O7—Sn1—C18—C19 | 25.3 (3) | C47—C48—C49—C50 | −73.9 (5) |
Sn1—C18—C19—C20 | 62.6 (5) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn4(C4H9)8(C17H12NO4)4O2] |
Mr | 2140.76 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 13.0412 (3), 13.6473 (3), 15.6097 (5) |
α, β, γ (°) | 103.5885 (11), 94.9563 (13), 115.8557 (17) |
V (Å3) | 2372.76 (11) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.11 |
Crystal size (mm) | 0.13 × 0.13 × 0.13 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.874, 0.874 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19979, 10658, 8196 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.117, 1.08 |
No. of reflections | 10658 |
No. of parameters | 589 |
No. of restraints | 22 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.43, −1.37 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corportaion, 1994).
Sn1—O9 | 2.031 (3) | O4—C9 | 1.237 (5) |
Sn1—C22 | 2.131 (5) | O5—C26 | 1.202 (6) |
Sn1—C18 | 2.137 (5) | O6—C33 | 1.204 (7) |
Sn1—O3 | 2.214 (3) | O7—C34 | 1.258 (5) |
Sn1—O7 | 2.232 (3) | O8—C34 | 1.263 (5) |
Sn2—O9 | 2.057 (3) | N1—C8 | 1.394 (7) |
Sn2—C43 | 2.117 (5) | N1—C1 | 1.404 (7) |
Sn2—C47 | 2.125 (5) | N1—C10' | 1.490 (5) |
Sn2—O9i | 2.157 (3) | N1—C10 | 1.497 (6) |
Sn2—O8 | 2.277 (3) | N2—C33 | 1.390 (7) |
Sn2—O3i | 2.725 (3) | N2—C26 | 1.399 (7) |
O1—C1 | 1.209 (6) | N2—C35' | 1.491 (5) |
O2—C8 | 1.213 (7) | N2—C35 | 1.491 (6) |
O3—C9 | 1.304 (5) | ||
O9—Sn1—C22 | 110.61 (15) | C43—Sn2—O3i | 81.00 (15) |
O9—Sn1—C18 | 111.03 (15) | C47—Sn2—O3i | 78.41 (14) |
C22—Sn1—C18 | 138.35 (17) | O9i—Sn2—O3i | 66.68 (9) |
O9—Sn1—O3 | 79.76 (11) | O8—Sn2—O3i | 125.36 (10) |
C22—Sn1—O3 | 93.41 (16) | C9—O3—Sn1 | 113.0 (3) |
C18—Sn1—O3 | 93.34 (15) | C34—O7—Sn1 | 139.1 (3) |
O9—Sn1—O7 | 90.66 (11) | C34—O8—Sn2 | 134.8 (3) |
C22—Sn1—O7 | 87.22 (16) | Sn1—O9—Sn2 | 137.14 (14) |
C18—Sn1—O7 | 92.81 (15) | Sn1—O9—Sn2i | 119.72 (13) |
O3—Sn1—O7 | 169.99 (11) | Sn2—O9—Sn2i | 103.14 (11) |
O9—Sn2—C43 | 107.76 (16) | C8—N1—C1 | 111.6 (4) |
O9—Sn2—C47 | 105.90 (15) | C8—N1—C10' | 113.8 (5) |
C43—Sn2—C47 | 144.66 (19) | C1—N1—C10' | 133.0 (5) |
O9—Sn2—O9i | 76.86 (11) | C8—N1—C10 | 140.4 (6) |
C43—Sn2—O9i | 99.18 (16) | C1—N1—C10 | 105.2 (6) |
C47—Sn2—O9i | 98.61 (16) | C33—N2—C26 | 111.9 (4) |
O9—Sn2—O8 | 91.08 (11) | C33—N2—C35' | 135.9 (5) |
C43—Sn2—O8 | 84.67 (16) | C26—N2—C35' | 111.3 (5) |
C47—Sn2—O8 | 84.24 (16) | C33—N2—C35 | 105.7 (5) |
O9i—Sn2—O8 | 167.93 (10) | C26—N2—C35 | 141.1 (6) |
O9—Sn2—O3i | 143.48 (10) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Organotin compounds are widely used in the biosphere as fungicides, pesticides, antifouling coating materials, PVC stabilizers, catalysts in polymer chemistry, precursors for forming SnO2 films on glass, wood preservatives and antitumourous agents (Molloy et al., 1986; Barbieri et al., 1982; Danish, Alt et al., 1995; Crowe et al., 1980). It has been reported that diorganotin complexes with the derivatives of carboxylic acids and amino acids show maximum antitumour activity, low mammalian toxicity and have less nephrotoxicity unlike cis-platin (Sandhu & Verma, 1987; Gielen, El Khloufi, Biesemans, Kayser & Willem, 1993; Gielen, El Khloufi, Biesemans & Willem, 1993; Danish, Ali et al., 1995). In order to develop new types of organotin biocides, based on carboxylates and amino acids containing compounds, we have synthesized a new dimeric organotin(IV)carboxylate, tetrabutylbis(N-phthaloylphenylalaninato)distannoxane dimer, (I), the crystal structure of which has been reported in this paper.
The structure of (I) (Fig. 1) is composed of centrosymmetric dimers lying about inversion centers. The structure contains N-phthaloylphenylalaninate anions one of which acting as a monodentate ligand bridges the two Sn atoms via O3 and forms a four-membered ring Sn1/O3/Sn2i/O9 [symmetry code: (i) −x + 2, −y + 1, −z + 1], and a second anion that acts as a bidentate ligand and bridges the two Sn atoms resulting in a six-membered ring Sn1/O7/C34/O8/Sn2/O9. There is a central four-membered ring Sn2/O9/Sn2i/O9i with Sn1/O3/Sn2i/O9 and Sn1i/O3i/O9i/Sn2 rings flanking it on opposite sides. The endocyclic Sn atoms of the Sn2O2 core are six-coordinate in a C2SnO4 skew-trapezoidal bipyramidal environment, wherein Sn2 is coordinated to two α-C atoms of the n-butyl groups at axial positions and two bridging O atoms and two O atoms of the anions forming the basal plane. This basal plane (Sn2/O8/O9/O3i/O9i) is essentially planar, with a maximum deviation of any atom from the plane of 0.024 (3) Å, and C43 and C47 lie 2.043 (6) and 1.999 (5) Å, respectively, above and below this plane, with the angle C—Sn—C = 144.66 (19)°. The endocyclic Sn—O distances in the Sn2O2 core, 2.057 (3) and 2.157 (3) Å, although significantly different from each other, are similar to the corresponding distances reported in similar structures, e.g. the tetrabutylbis(N-phthaloylglycinato)distannoxane dimer (Parvez et al., 2000), bis[1,1,3,3-tetrabutyl-1,3-bis(picolinato N-oxide)] distannoxane hydrate (Ng, 1998) and the tetrabutylbis(N,N-diethylthiocarbamoylthio)distannoxane dimer (Ng & Kumar Das, 1995). The exocyclic distances Sn2—O8 [2.277 (3) Å] and Sn2—O3i [2.725 (3) Å] indicate strong and relatively weak Sn···O interactions similar to those observed in the above-mentioned complexes. The exocyclic Sn1 atom is essentially five-coordinate in a distorted trigonal bipyramidal geometry, with a C—Sn—C angle of 138.35 (17)°; the Sn1—O distances are in the range 2.031 (3)–2.232(3 Å. The Sn—C distances in (I) lie in the narrow range 2.117 (3)—2.137 (5) Å [mean 2.128 (7) Å] and agree with the values reported for related structures. It is interesting to note that the central portion of the dimer comprising of Sn4O8C2 is somewhat flattened wherein three four-membered and two six-membered rings are fused; the maximum deviation of any atom from the plane of these atoms is 0.134 (3) Å. A search of the Cambridge Structural Database (updated April 2002' Allen & Kennard, 1993), resulted in 78 hits containing similar fused-ring systems.
As a result of different modes of coordination of the two ligands, the C9—O3 distance [1.304 (5) Å] in the carboxyl group of the monodentate ligand is significantly longer than C9—O4 [1.237 (5) Å], which is clearly a double bond. The corresponding distances C34—O7 and C34—O8 in the bidentate ligand [1.258 (5) and 1.263 (5) Å, respectively] represent a delocalized system, with bond distances lying between those observed for the monodentate ligand. The mean planes of the phthalimido and the phenyl groups in the monodentate and bidentate ligands are inclined at 82.90 (14) and 62.18 (13)°, respectively.
Even at temperature as low as 120 (2) K, the C atoms C10, C11, C35 and C36 of the ligands and C44 and C45 of a butyl group were found to be disordered. Therefore, the distances N—C and C—C involving these atoms were restrained during the refinements. The rest of the molecular dimensions in the ligands were normal.