metal-organic compounds
The crystal structure of the title compound, [Sn(C4H9)2(C13H7F2O3)2], contains discrete molecules in which the central Sn atoms are asymmetrically coordinated to two carboxylates and by two C atoms of two n-butyl groups. The Sn—C distances are identical within 3σ limits [mean Sn—C 2.118 (2) Å]. The Sn—O distances are significantly different from each other, with the mean value for the shorter distances being 2.098 (3) Å, while the longer Sn—O distances are 2.570 (3) and 2.686 (3) Å. The geometry around the Sn atom is highly distorted octahedral, that may be best described as one based on skew-trapezoidal planar geometry. The hydroxyl groups and the carboxylate O atoms are hydrogen bonded, forming six-membered rings and exhibit an S(6) pattern of hydrogen bonding.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012655/ww6028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012655/ww6028Isup2.hkl |
CCDC reference: 193717
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.007 Å
- Disorder in main residue
- R factor = 0.050
- wR factor = 0.148
- Data-to-parameter ratio = 16.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
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).
Di-n-butylbis(2',4'-difluoro-4-hydroxybiphenyl-3-carboxylato-O,O')tin(IV) top
Crystal data top
[Sn(C4H9)2(C13H7F2O3)2] | F(000) = 1480 |
Mr = 731.29 | Dx = 1.537 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3676 (1) Å | Cell parameters from 12703 reflections |
b = 9.2278 (1) Å | θ = 1.0–27.4° |
c = 33.3643 (5) Å | µ = 0.88 mm−1 |
β = 98.0917 (6)° | T = 170 K |
V = 3160.19 (7) Å3 | Block, colourless |
Z = 4 | 0.15 × 0.13 × 0.09 mm |
Data collection top
Nonius KappaCCD diffractometer | 6945 independent reflections |
Radiation source: fine-focus sealed tube | 5776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scans | θmax = 27.4°, θmin = 1.2° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −13→13 |
Tmin = 0.879, Tmax = 0.928 | k = −11→11 |
12703 measured reflections | l = −42→42 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.075P)2 + 5.5P] where P = (Fo2 + 2Fc2)/3 |
6945 reflections | (Δ/σ)max = 0.001 |
426 parameters | Δρmax = 0.83 e Å−3 |
6 restraints | Δρmin = −0.67 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.67984 (3) | 0.33183 (3) | 0.071834 (8) | 0.03496 (12) | |
O1 | 0.5688 (3) | 0.3806 (4) | 0.11788 (9) | 0.0393 (7) | |
O2 | 0.4269 (3) | 0.4063 (4) | 0.06245 (9) | 0.0459 (8) | |
O3 | 0.1926 (3) | 0.5048 (5) | 0.06815 (9) | 0.0512 (9) | |
H3 | 0.2560 | 0.4847 | 0.0560 | 0.077* | |
O4 | 0.8196 (3) | 0.3062 (3) | 0.12343 (9) | 0.0365 (7) | |
O5 | 0.9149 (3) | 0.2445 (4) | 0.07122 (9) | 0.0439 (8) | |
O6 | 1.1496 (4) | 0.1297 (5) | 0.08294 (12) | 0.0620 (11) | |
H6 | 1.0810 | 0.1611 | 0.0693 | 0.093* | |
F1 | 0.2407 (5) | 0.7550 (5) | 0.24465 (16) | 0.0476 (14) | 0.50 |
F1' | 0.4536 (6) | 0.3052 (5) | 0.24164 (18) | 0.0545 (15) | 0.50 |
F2 | 0.4238 (3) | 0.5263 (5) | 0.36243 (9) | 0.0779 (12) | |
F3 | 1.0329 (5) | 0.4270 (5) | 0.24355 (15) | 0.0456 (13) | 0.50 |
F3' | 1.2614 (6) | −0.0120 (6) | 0.27009 (19) | 0.0616 (17) | 0.50 |
F4 | 1.1577 (4) | 0.2725 (5) | 0.37427 (10) | 0.0766 (10) | |
C1 | 0.6299 (5) | 0.1230 (6) | 0.04806 (14) | 0.0430 (11) | |
H1A | 0.6749 | 0.0488 | 0.0664 | 0.052* | |
H1B | 0.5349 | 0.1082 | 0.0470 | 0.052* | |
C2 | 0.6670 (4) | 0.1022 (5) | 0.00557 (13) | 0.0406 (10) | |
H2A | 0.7618 | 0.1190 | 0.0067 | 0.049* | |
H2B | 0.6492 | 0.0005 | −0.0029 | 0.049* | |
C3 | 0.5949 (5) | 0.2017 (5) | −0.02604 (14) | 0.0459 (12) | |
H3A | 0.6173 | 0.3034 | −0.0186 | 0.055* | |
H3B | 0.5001 | 0.1895 | −0.0260 | 0.055* | |
C4 | 0.6265 (7) | 0.1734 (7) | −0.06853 (16) | 0.0599 (15) | |
H4A | 0.5785 | 0.2422 | −0.0875 | 0.090* | |
H4B | 0.6010 | 0.0742 | −0.0767 | 0.090* | |
H4C | 0.7202 | 0.1855 | −0.0688 | 0.090* | |
C5 | 0.7022 (4) | 0.5391 (5) | 0.04660 (14) | 0.0428 (11) | |
H5A | 0.6430 | 0.5453 | 0.0207 | 0.051* | |
H5B | 0.6731 | 0.6125 | 0.0650 | 0.051* | |
C6 | 0.8383 (4) | 0.5799 (5) | 0.03869 (15) | 0.0469 (12) | |
H6A | 0.9007 | 0.5683 | 0.0638 | 0.056* | |
H6B | 0.8657 | 0.5150 | 0.0178 | 0.056* | |
C7 | 0.8390 (5) | 0.7360 (7) | 0.02438 (18) | 0.0610 (15) | |
H7A | 0.7904 | 0.7422 | −0.0033 | 0.073* | |
H7B | 0.7929 | 0.7968 | 0.0423 | 0.073* | |
C8 | 0.9747 (6) | 0.7957 (8) | 0.0241 (3) | 0.088 (2) | |
H8A | 0.9690 | 0.8925 | 0.0119 | 0.132* | |
H8B | 1.0235 | 0.7314 | 0.0083 | 0.132* | |
H8C | 1.0195 | 0.8021 | 0.0520 | 0.132* | |
C9 | 0.4536 (4) | 0.4167 (5) | 0.10005 (13) | 0.0382 (10) | |
C10 | 0.3590 (4) | 0.4700 (5) | 0.12576 (13) | 0.0334 (9) | |
C11 | 0.2337 (4) | 0.5136 (5) | 0.10830 (13) | 0.0377 (10) | |
C12 | 0.1497 (4) | 0.5694 (5) | 0.13323 (14) | 0.0408 (10) | |
H12 | 0.0661 | 0.6031 | 0.1217 | 0.049* | |
C13 | 0.1856 (4) | 0.5769 (5) | 0.17433 (14) | 0.0371 (10) | |
H13 | 0.1257 | 0.6138 | 0.1908 | 0.044* | |
C14 | 0.3095 (4) | 0.5309 (4) | 0.19248 (12) | 0.0312 (9) | |
C15 | 0.3943 (4) | 0.4785 (5) | 0.16778 (12) | 0.0320 (9) | |
H15 | 0.4786 | 0.4474 | 0.1795 | 0.038* | |
C16 | 0.3444 (4) | 0.5313 (5) | 0.23746 (12) | 0.0318 (9) | |
C17 | 0.3069 (4) | 0.6414 (5) | 0.26151 (14) | 0.0394 (10) | |
H17 | 0.2602 | 0.7207 | 0.2484 | 0.047* | 0.50 |
C18 | 0.3325 (5) | 0.6440 (6) | 0.30303 (15) | 0.0494 (13) | |
H18 | 0.3049 | 0.7224 | 0.3182 | 0.059* | |
C19 | 0.3990 (4) | 0.5295 (7) | 0.32144 (14) | 0.0487 (13) | |
C20 | 0.4421 (4) | 0.4160 (6) | 0.30000 (15) | 0.0470 (12) | |
H20 | 0.4894 | 0.3371 | 0.3132 | 0.056* | |
C21 | 0.4132 (4) | 0.4225 (4) | 0.25889 (14) | 0.0375 (10) | |
H21 | 0.4434 | 0.3454 | 0.2438 | 0.045* | 0.50 |
C22 | 0.9192 (4) | 0.2558 (5) | 0.10911 (14) | 0.0371 (10) | |
C23 | 1.0330 (4) | 0.2077 (5) | 0.13726 (14) | 0.0359 (10) | |
C24 | 1.1418 (5) | 0.1451 (5) | 0.12266 (16) | 0.0439 (11) | |
C25 | 1.2464 (5) | 0.0992 (6) | 0.15055 (17) | 0.0522 (13) | |
H25 | 1.3197 | 0.0559 | 0.1411 | 0.063* | |
C26 | 1.2455 (4) | 0.1154 (6) | 0.19142 (17) | 0.0498 (13) | |
H26 | 1.3180 | 0.0823 | 0.2097 | 0.060* | |
C27 | 1.1398 (4) | 0.1798 (5) | 0.20687 (14) | 0.0353 (9) | |
C28 | 1.0341 (4) | 0.2237 (5) | 0.17911 (13) | 0.0325 (9) | |
H28 | 0.9607 | 0.2656 | 0.1888 | 0.039* | |
C29 | 1.1419 (4) | 0.2016 (4) | 0.25104 (14) | 0.0339 (9) | |
C30 | 1.0871 (4) | 0.3204 (4) | 0.26718 (14) | 0.0366 (10) | |
H30 | 1.0440 | 0.3893 | 0.2488 | 0.044* | 0.50 |
C31 | 1.0900 (5) | 0.3469 (6) | 0.30785 (16) | 0.0482 (12) | |
H31 | 1.0505 | 0.4306 | 0.3174 | 0.058* | |
C32 | 1.1525 (5) | 0.2468 (7) | 0.33397 (15) | 0.0532 (14) | |
C33 | 1.2088 (5) | 0.1258 (7) | 0.32107 (17) | 0.0568 (15) | |
H33 | 1.2517 | 0.0571 | 0.3396 | 0.068* | |
C34 | 1.2005 (5) | 0.1078 (5) | 0.28005 (16) | 0.0456 (12) | |
H34 | 1.2388 | 0.0227 | 0.2708 | 0.055* | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03349 (17) | 0.0466 (2) | 0.02440 (16) | 0.01009 (13) | 0.00265 (11) | −0.00081 (13) |
O1 | 0.0328 (15) | 0.058 (2) | 0.0273 (14) | 0.0129 (14) | 0.0037 (12) | −0.0047 (14) |
O2 | 0.0435 (17) | 0.066 (2) | 0.0267 (15) | 0.0127 (16) | 0.0000 (13) | −0.0045 (16) |
O3 | 0.0389 (17) | 0.076 (3) | 0.0346 (17) | 0.0122 (17) | −0.0074 (13) | −0.0064 (17) |
O4 | 0.0306 (14) | 0.0469 (19) | 0.0303 (15) | 0.0099 (13) | −0.0010 (11) | 0.0005 (13) |
O5 | 0.0422 (17) | 0.056 (2) | 0.0335 (16) | 0.0121 (15) | 0.0067 (13) | 0.0047 (16) |
O6 | 0.050 (2) | 0.090 (3) | 0.046 (2) | 0.028 (2) | 0.0093 (17) | −0.002 (2) |
F1 | 0.063 (3) | 0.037 (3) | 0.044 (3) | 0.023 (3) | 0.007 (3) | −0.008 (2) |
F1' | 0.062 (4) | 0.043 (3) | 0.057 (4) | 0.015 (3) | 0.003 (3) | 0.002 (3) |
F2 | 0.063 (2) | 0.140 (4) | 0.0291 (15) | −0.015 (2) | 0.0012 (13) | 0.0067 (19) |
F3 | 0.048 (3) | 0.041 (3) | 0.046 (3) | 0.014 (2) | 0.002 (2) | 0.003 (3) |
F3' | 0.087 (4) | 0.032 (3) | 0.061 (4) | 0.030 (3) | −0.005 (3) | 0.005 (3) |
F4 | 0.087 (3) | 0.101 (3) | 0.0403 (17) | −0.013 (2) | 0.0031 (16) | 0.0029 (19) |
C1 | 0.049 (3) | 0.046 (3) | 0.033 (2) | 0.003 (2) | 0.0033 (19) | −0.009 (2) |
C2 | 0.044 (2) | 0.042 (3) | 0.034 (2) | 0.005 (2) | 0.0022 (18) | −0.010 (2) |
C3 | 0.066 (3) | 0.038 (3) | 0.033 (2) | 0.002 (2) | 0.005 (2) | 0.001 (2) |
C4 | 0.081 (4) | 0.061 (4) | 0.038 (3) | −0.011 (3) | 0.009 (3) | −0.012 (3) |
C5 | 0.056 (3) | 0.038 (3) | 0.032 (2) | 0.013 (2) | 0.0001 (19) | −0.002 (2) |
C6 | 0.046 (3) | 0.044 (3) | 0.047 (3) | 0.005 (2) | −0.008 (2) | 0.010 (2) |
C7 | 0.066 (4) | 0.060 (4) | 0.052 (3) | 0.002 (3) | −0.007 (3) | 0.011 (3) |
C8 | 0.081 (5) | 0.073 (5) | 0.111 (6) | −0.001 (4) | 0.020 (4) | 0.037 (4) |
C9 | 0.034 (2) | 0.047 (3) | 0.033 (2) | 0.0065 (19) | 0.0025 (17) | −0.001 (2) |
C10 | 0.0281 (19) | 0.039 (2) | 0.033 (2) | 0.0036 (17) | 0.0030 (16) | −0.0029 (19) |
C11 | 0.033 (2) | 0.044 (3) | 0.034 (2) | 0.0039 (19) | −0.0018 (17) | 0.001 (2) |
C12 | 0.0257 (19) | 0.051 (3) | 0.045 (2) | 0.0082 (19) | 0.0014 (17) | 0.001 (2) |
C13 | 0.030 (2) | 0.042 (3) | 0.039 (2) | 0.0042 (18) | 0.0062 (17) | 0.001 (2) |
C14 | 0.0308 (19) | 0.029 (2) | 0.033 (2) | −0.0003 (16) | 0.0029 (16) | 0.0023 (17) |
C15 | 0.0274 (19) | 0.036 (2) | 0.032 (2) | 0.0049 (16) | 0.0005 (15) | −0.0020 (18) |
C16 | 0.0263 (18) | 0.038 (2) | 0.032 (2) | −0.0029 (16) | 0.0050 (15) | −0.0019 (18) |
C17 | 0.038 (2) | 0.041 (3) | 0.040 (2) | −0.0009 (19) | 0.0083 (19) | −0.007 (2) |
C18 | 0.038 (2) | 0.072 (4) | 0.040 (3) | −0.006 (2) | 0.008 (2) | −0.018 (3) |
C19 | 0.036 (2) | 0.081 (4) | 0.029 (2) | −0.017 (2) | 0.0032 (18) | 0.002 (2) |
C20 | 0.030 (2) | 0.064 (3) | 0.045 (3) | −0.006 (2) | −0.0026 (19) | 0.018 (3) |
C21 | 0.029 (2) | 0.036 (2) | 0.047 (3) | 0.0010 (18) | 0.0030 (18) | 0.001 (2) |
C22 | 0.032 (2) | 0.041 (3) | 0.040 (2) | 0.0038 (18) | 0.0064 (17) | 0.003 (2) |
C23 | 0.029 (2) | 0.037 (2) | 0.041 (2) | 0.0046 (17) | 0.0032 (17) | 0.0025 (19) |
C24 | 0.041 (2) | 0.043 (3) | 0.048 (3) | 0.010 (2) | 0.006 (2) | 0.000 (2) |
C25 | 0.035 (2) | 0.062 (3) | 0.058 (3) | 0.021 (2) | 0.003 (2) | −0.007 (3) |
C26 | 0.035 (2) | 0.050 (3) | 0.060 (3) | 0.014 (2) | −0.011 (2) | −0.002 (3) |
C27 | 0.031 (2) | 0.029 (2) | 0.043 (2) | 0.0005 (17) | −0.0024 (17) | −0.0021 (19) |
C28 | 0.0265 (18) | 0.027 (2) | 0.042 (2) | −0.0005 (16) | 0.0009 (16) | 0.0001 (19) |
C29 | 0.0295 (19) | 0.026 (2) | 0.044 (2) | −0.0028 (15) | −0.0049 (17) | 0.0020 (18) |
C30 | 0.032 (2) | 0.030 (2) | 0.046 (3) | −0.0052 (17) | 0.0002 (18) | 0.005 (2) |
C31 | 0.044 (3) | 0.051 (3) | 0.051 (3) | −0.004 (2) | 0.009 (2) | −0.005 (2) |
C32 | 0.051 (3) | 0.067 (4) | 0.039 (3) | −0.018 (3) | −0.001 (2) | 0.005 (3) |
C33 | 0.053 (3) | 0.060 (4) | 0.052 (3) | −0.001 (3) | −0.012 (2) | 0.023 (3) |
C34 | 0.045 (3) | 0.032 (2) | 0.055 (3) | 0.002 (2) | −0.008 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.095 (3) | C8—H8C | 0.9800 |
Sn1—O4 | 2.101 (3) | C9—C10 | 1.475 (6) |
Sn1—C5 | 2.116 (5) | C10—C15 | 1.400 (6) |
Sn1—C1 | 2.120 (5) | C10—C11 | 1.406 (5) |
Sn1—O5 | 2.570 (3) | C11—C12 | 1.385 (6) |
Sn1—O2 | 2.686 (3) | C12—C13 | 1.371 (6) |
O1—C9 | 1.300 (5) | C12—H12 | 0.9500 |
O2—C9 | 1.250 (5) | C13—C14 | 1.406 (6) |
O3—C11 | 1.350 (5) | C13—H13 | 0.9500 |
O3—H3 | 0.8400 | C14—C15 | 1.375 (6) |
O4—C22 | 1.285 (5) | C14—C16 | 1.493 (6) |
O5—C22 | 1.263 (5) | C15—H15 | 0.9500 |
O6—C24 | 1.346 (6) | C16—C21 | 1.373 (6) |
O6—H6 | 0.8400 | C16—C17 | 1.384 (6) |
F1—C17 | 1.334 (4) | C17—C18 | 1.373 (7) |
F1'—C21 | 1.321 (4) | C17—H17 | 0.9498 |
F2—C19 | 1.356 (5) | C18—C19 | 1.361 (8) |
F3—C30 | 1.334 (4) | C18—H18 | 0.9500 |
F3'—C34 | 1.338 (4) | C19—C20 | 1.378 (8) |
F4—C32 | 1.359 (6) | C20—C21 | 1.363 (6) |
C1—C2 | 1.532 (6) | C20—H20 | 0.9500 |
C1—H1A | 0.9900 | C21—H21 | 0.9491 |
C1—H1B | 0.9900 | C22—C23 | 1.469 (6) |
C2—C3 | 1.514 (7) | C23—C28 | 1.403 (6) |
C2—H2A | 0.9900 | C23—C24 | 1.414 (6) |
C2—H2B | 0.9900 | C24—C25 | 1.392 (7) |
C3—C4 | 1.521 (7) | C25—C26 | 1.373 (7) |
C3—H3A | 0.9900 | C25—H25 | 0.9500 |
C3—H3B | 0.9900 | C26—C27 | 1.407 (7) |
C4—H4A | 0.9800 | C26—H26 | 0.9500 |
C4—H4B | 0.9800 | C27—C28 | 1.392 (6) |
C4—H4C | 0.9800 | C27—C29 | 1.484 (6) |
C5—C6 | 1.518 (5) | C28—H28 | 0.9500 |
C5—H5A | 0.9900 | C29—C34 | 1.375 (6) |
C5—H5B | 0.9900 | C29—C30 | 1.379 (6) |
C6—C7 | 1.518 (8) | C30—C31 | 1.375 (7) |
C6—H6A | 0.9900 | C30—H30 | 0.9496 |
C6—H6B | 0.9900 | C31—C32 | 1.368 (8) |
C7—C8 | 1.513 (5) | C31—H31 | 0.9500 |
C7—H7A | 0.9900 | C32—C33 | 1.358 (9) |
C7—H7B | 0.9900 | C33—C34 | 1.369 (8) |
C8—H8A | 0.9800 | C33—H33 | 0.9500 |
C8—H8B | 0.9800 | C34—H34 | 0.9505 |
O1—Sn1—O4 | 79.05 (11) | C13—C12—C11 | 120.9 (4) |
O1—Sn1—C5 | 101.55 (15) | C13—C12—H12 | 119.5 |
O4—Sn1—C5 | 109.03 (15) | C11—C12—H12 | 119.5 |
O1—Sn1—C1 | 109.83 (17) | C12—C13—C14 | 121.2 (4) |
O4—Sn1—C1 | 107.93 (16) | C12—C13—H13 | 119.4 |
C5—Sn1—C1 | 135.04 (18) | C14—C13—H13 | 119.4 |
O1—Sn1—O5 | 133.88 (10) | C15—C14—C13 | 118.1 (4) |
O4—Sn1—O5 | 54.97 (11) | C15—C14—C16 | 121.2 (4) |
C5—Sn1—O5 | 97.07 (14) | C13—C14—C16 | 120.6 (4) |
C1—Sn1—O5 | 83.90 (16) | C14—C15—C10 | 121.4 (4) |
O1—Sn1—O2 | 53.28 (10) | C14—C15—H15 | 119.3 |
O4—Sn1—O2 | 132.33 (10) | C10—C15—H15 | 119.3 |
C5—Sn1—O2 | 83.23 (14) | C21—C16—C17 | 113.7 (4) |
C1—Sn1—O2 | 90.36 (16) | C21—C16—C14 | 123.8 (4) |
O5—Sn1—O2 | 172.17 (10) | C17—C16—C14 | 122.4 (4) |
C9—O1—Sn1 | 106.5 (3) | F1—C17—C18 | 115.2 (5) |
C9—O2—Sn1 | 80.1 (2) | F1—C17—C16 | 120.2 (4) |
C11—O3—H3 | 109.5 | C18—C17—C16 | 124.6 (4) |
C22—O4—Sn1 | 103.5 (3) | C18—C17—H17 | 117.7 |
C22—O5—Sn1 | 82.3 (2) | C16—C17—H17 | 117.8 |
C24—O6—H6 | 109.5 | C19—C18—C17 | 117.1 (5) |
C2—C1—Sn1 | 112.3 (3) | C19—C18—H18 | 121.5 |
C2—C1—H1A | 109.1 | C17—C18—H18 | 121.5 |
Sn1—C1—H1A | 109.1 | F2—C19—C18 | 119.0 (5) |
C2—C1—H1B | 109.1 | F2—C19—C20 | 118.6 (5) |
Sn1—C1—H1B | 109.1 | C18—C19—C20 | 122.5 (4) |
H1A—C1—H1B | 107.9 | C21—C20—C19 | 116.6 (5) |
C3—C2—C1 | 113.9 (4) | C21—C20—H20 | 121.7 |
C3—C2—H2A | 108.8 | C19—C20—H20 | 121.7 |
C1—C2—H2A | 108.8 | F1'—C21—C20 | 111.3 (5) |
C3—C2—H2B | 108.8 | F1'—C21—C16 | 123.1 (5) |
C1—C2—H2B | 108.8 | C20—C21—C16 | 125.5 (4) |
H2A—C2—H2B | 107.7 | C20—C21—H21 | 117.2 |
C2—C3—C4 | 113.3 (4) | C16—C21—H21 | 117.3 |
C2—C3—H3A | 108.9 | O5—C22—O4 | 119.0 (4) |
C4—C3—H3A | 108.9 | O5—C22—C23 | 121.8 (4) |
C2—C3—H3B | 108.9 | O4—C22—C23 | 119.1 (4) |
C4—C3—H3B | 108.9 | C28—C23—C24 | 119.4 (4) |
H3A—C3—H3B | 107.7 | C28—C23—C22 | 119.9 (4) |
C3—C4—H4A | 109.5 | C24—C23—C22 | 120.7 (4) |
C3—C4—H4B | 109.5 | O6—C24—C25 | 118.5 (4) |
H4A—C4—H4B | 109.5 | O6—C24—C23 | 122.9 (4) |
C3—C4—H4C | 109.5 | C25—C24—C23 | 118.6 (5) |
H4A—C4—H4C | 109.5 | C26—C25—C24 | 121.1 (4) |
H4B—C4—H4C | 109.5 | C26—C25—H25 | 119.4 |
C6—C5—Sn1 | 116.7 (3) | C24—C25—H25 | 119.4 |
C6—C5—H5A | 108.1 | C25—C26—C27 | 121.6 (4) |
Sn1—C5—H5A | 108.1 | C25—C26—H26 | 119.2 |
C6—C5—H5B | 108.1 | C27—C26—H26 | 119.2 |
Sn1—C5—H5B | 108.1 | C28—C27—C26 | 117.4 (4) |
H5A—C5—H5B | 107.3 | C28—C27—C29 | 121.4 (4) |
C7—C6—C5 | 109.6 (4) | C26—C27—C29 | 121.2 (4) |
C7—C6—H6A | 109.8 | C27—C28—C23 | 121.8 (4) |
C5—C6—H6A | 109.8 | C27—C28—H28 | 119.1 |
C7—C6—H6B | 109.8 | C23—C28—H28 | 119.1 |
C5—C6—H6B | 109.8 | C34—C29—C30 | 113.0 (4) |
H6A—C6—H6B | 108.2 | C34—C29—C27 | 123.9 (4) |
C8—C7—C6 | 113.2 (5) | C30—C29—C27 | 123.1 (4) |
C8—C7—H7A | 108.9 | F3—C30—C31 | 113.7 (5) |
C6—C7—H7A | 108.9 | F3—C30—C29 | 121.2 (5) |
C8—C7—H7B | 108.9 | C31—C30—C29 | 125.0 (4) |
C6—C7—H7B | 108.9 | C31—C30—H30 | 117.4 |
H7A—C7—H7B | 107.8 | C29—C30—H30 | 117.5 |
C7—C8—H8A | 109.5 | C32—C31—C30 | 116.8 (5) |
C7—C8—H8B | 109.5 | C32—C31—H31 | 121.6 |
H8A—C8—H8B | 109.5 | C30—C31—H31 | 121.6 |
C7—C8—H8C | 109.5 | C33—C32—F4 | 119.8 (5) |
H8A—C8—H8C | 109.5 | C33—C32—C31 | 122.7 (5) |
H8B—C8—H8C | 109.5 | F4—C32—C31 | 117.5 (6) |
O2—C9—O1 | 119.9 (4) | C32—C33—C34 | 116.5 (5) |
O2—C9—C10 | 122.6 (4) | C32—C33—H33 | 121.7 |
O1—C9—C10 | 117.5 (4) | C34—C33—H33 | 121.7 |
C15—C10—C11 | 119.6 (4) | F3'—C34—C33 | 112.5 (5) |
C15—C10—C9 | 120.0 (4) | F3'—C34—C29 | 121.5 (5) |
C11—C10—C9 | 120.4 (4) | C33—C34—C29 | 126.0 (5) |
O3—C11—C12 | 118.8 (4) | C33—C34—H34 | 116.9 |
O3—C11—C10 | 122.5 (4) | C29—C34—H34 | 117.1 |
C12—C11—C10 | 118.7 (4) | ||
O4—Sn1—O1—C9 | 177.2 (3) | C21—C16—C17—F1 | 179.2 (5) |
C5—Sn1—O1—C9 | 69.7 (3) | C14—C16—C17—F1 | −2.3 (7) |
C1—Sn1—O1—C9 | −77.6 (3) | C21—C16—C17—C18 | −1.1 (7) |
O5—Sn1—O1—C9 | −178.5 (3) | C14—C16—C17—C18 | 177.5 (4) |
O2—Sn1—O1—C9 | −2.7 (3) | F1—C17—C18—C19 | 179.6 (5) |
O1—Sn1—O2—C9 | 2.7 (3) | C16—C17—C18—C19 | −0.2 (7) |
O4—Sn1—O2—C9 | 2.5 (4) | C17—C18—C19—F2 | −178.6 (4) |
C5—Sn1—O2—C9 | −107.2 (3) | C17—C18—C19—C20 | 1.2 (7) |
C1—Sn1—O2—C9 | 117.4 (3) | F2—C19—C20—C21 | 179.0 (4) |
O1—Sn1—O4—C22 | 173.7 (3) | C18—C19—C20—C21 | −0.8 (7) |
C5—Sn1—O4—C22 | −87.8 (3) | C19—C20—C21—F1' | −177.0 (5) |
C1—Sn1—O4—C22 | 66.2 (3) | C19—C20—C21—C16 | −0.7 (7) |
O5—Sn1—O4—C22 | −2.5 (3) | C17—C16—C21—F1' | 177.4 (5) |
O2—Sn1—O4—C22 | 173.9 (3) | C14—C16—C21—F1' | −1.1 (7) |
O1—Sn1—O5—C22 | −2.7 (4) | C17—C16—C21—C20 | 1.6 (6) |
O4—Sn1—O5—C22 | 2.5 (3) | C14—C16—C21—C20 | −177.0 (4) |
C5—Sn1—O5—C22 | 110.8 (3) | Sn1—O5—C22—O4 | −3.8 (4) |
C1—Sn1—O5—C22 | −114.4 (3) | Sn1—O5—C22—C23 | 173.8 (4) |
O1—Sn1—C1—C2 | 159.0 (3) | Sn1—O4—C22—O5 | 4.8 (5) |
O4—Sn1—C1—C2 | −116.5 (3) | Sn1—O4—C22—C23 | −172.9 (4) |
C5—Sn1—C1—C2 | 27.5 (5) | O5—C22—C23—C28 | 179.4 (4) |
O5—Sn1—C1—C2 | −66.4 (3) | O4—C22—C23—C28 | −3.0 (7) |
O2—Sn1—C1—C2 | 108.3 (3) | O5—C22—C23—C24 | −0.7 (7) |
Sn1—C1—C2—C3 | −63.8 (5) | O4—C22—C23—C24 | 176.9 (4) |
C1—C2—C3—C4 | −176.4 (4) | C28—C23—C24—O6 | −178.2 (5) |
O1—Sn1—C5—C6 | 133.7 (3) | C22—C23—C24—O6 | 1.9 (8) |
O4—Sn1—C5—C6 | 51.4 (4) | C28—C23—C24—C25 | 0.9 (7) |
C1—Sn1—C5—C6 | −92.3 (4) | C22—C23—C24—C25 | −179.0 (5) |
O5—Sn1—C5—C6 | −3.9 (4) | O6—C24—C25—C26 | 178.4 (5) |
O2—Sn1—C5—C6 | −176.0 (4) | C23—C24—C25—C26 | −0.8 (8) |
Sn1—C5—C6—C7 | −174.8 (3) | C24—C25—C26—C27 | −0.5 (9) |
C5—C6—C7—C8 | 168.0 (6) | C25—C26—C27—C28 | 1.5 (8) |
Sn1—O2—C9—O1 | −4.0 (4) | C25—C26—C27—C29 | −177.7 (5) |
Sn1—O2—C9—C10 | 175.6 (5) | C26—C27—C28—C23 | −1.3 (7) |
Sn1—O1—C9—O2 | 5.3 (6) | C29—C27—C28—C23 | 177.9 (4) |
Sn1—O1—C9—C10 | −174.3 (3) | C24—C23—C28—C27 | 0.1 (7) |
O2—C9—C10—C15 | 179.6 (5) | C22—C23—C28—C27 | −179.9 (4) |
O1—C9—C10—C15 | −0.8 (7) | C28—C27—C29—C34 | 146.3 (5) |
O2—C9—C10—C11 | −0.9 (7) | C26—C27—C29—C34 | −34.4 (7) |
O1—C9—C10—C11 | 178.7 (4) | C28—C27—C29—C30 | −35.0 (6) |
C15—C10—C11—O3 | −178.3 (4) | C26—C27—C29—C30 | 144.3 (5) |
C9—C10—C11—O3 | 2.2 (7) | C34—C29—C30—F3 | 175.9 (5) |
C15—C10—C11—C12 | 2.5 (7) | C27—C29—C30—F3 | −2.9 (7) |
C9—C10—C11—C12 | −177.0 (4) | C34—C29—C30—C31 | 0.7 (6) |
O3—C11—C12—C13 | 178.2 (5) | C27—C29—C30—C31 | −178.1 (4) |
C10—C11—C12—C13 | −2.6 (7) | F3—C30—C31—C32 | −175.5 (5) |
C11—C12—C13—C14 | 1.3 (7) | C29—C30—C31—C32 | 0.0 (7) |
C12—C13—C14—C15 | 0.2 (7) | C30—C31—C32—C33 | −0.5 (8) |
C12—C13—C14—C16 | −176.3 (4) | C30—C31—C32—F4 | 179.1 (4) |
C13—C14—C15—C10 | −0.3 (6) | F4—C32—C33—C34 | −179.5 (5) |
C16—C14—C15—C10 | 176.2 (4) | C31—C32—C33—C34 | 0.1 (8) |
C11—C10—C15—C14 | −1.0 (7) | C32—C33—C34—F3' | 178.4 (6) |
C9—C10—C15—C14 | 178.4 (4) | C32—C33—C34—C29 | 0.8 (8) |
C15—C14—C16—C21 | −37.7 (6) | C30—C29—C34—F3' | −178.6 (5) |
C13—C14—C16—C21 | 138.8 (4) | C27—C29—C34—F3' | 0.2 (8) |
C15—C14—C16—C17 | 143.9 (4) | C30—C29—C34—C33 | −1.1 (7) |
C13—C14—C16—C17 | −39.6 (6) | C27—C29—C34—C33 | 177.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.84 | 1.90 | 2.626 (4) | 144 |
O6—H6···O5 | 0.84 | 1.89 | 2.631 (5) | 146 |