Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100018898/av1061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100018898/av1061Isup2.hkl |
CCDC reference: 162548
Bis(tri-n-butyltin)oxide was purchased from Aldrich Chemical Co. and used without further purification. N-(Phosphonomethyl)glycine was isolated by acidifying a solution of commercial "Roundup" with concentrated HCl and allowing the free acid to crystallize. IR spectra were recorded as KBr pellets on a Perkin-Elmer Model 1725 F T—IR instrument. The elemental analyses were performed at the School of Chemical Sciences, Universiti Sains Malaysia, Penang. To a stirred solution of glyphosate (0.85 g, 5 mmol) in 95% ethanol (50 ml) was added dicyclohexylamine (1 ml) followed by bis(tri-n-butyltin)oxide (4.5 g, 7.5 mmol). After refluxing for 3–4 h, the mixture was concentrated to ca 10 ml with a rotatory evaporator before allowing it to stand in the freezer overnight. A white solid (3.1 g, 60%) was obtained on filtration. Recrystallization in methanol afforded crystals (m.p. 359–361 K) of tris-tri-n-butyltin N-(phosphonomethyl)glycinate which were suitable for X-ray crystallographic studies. Elemental analysis: Calculated (found) for C39H86NO5PSn3: C 45.20 (45.23), H 8.38 (8.43), N 1.35 (1.18%). IR (KBr,ν, cm-1) 1578 s (CO2asym); 1404 (CO2sym); 1138 (PO3asym); 877 (PO3sym); 1065 (O—P—O bending-stretching); 3300 (NH stretch).
The butyl groups coordinated to Sn2 were disordered and were modelled by pairs of isotropic atoms with occupation 0.5. The hydrogen atoms were constrained to have C—H = 0.95 Å and Uiso = 1.2Ueq for the atom to which they are attached. The weighting scheme employed was w = 1/[σcs(F2)+0.03 F2]2. The largest peaks and holes in the final difference map were close to the tin atoms.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR97 (Cascarano et al., 1996) and KRYSTAL (Hazell, 1995); program(s) used to refine structure: modified ORFLS (Busing et al., 1962) and KRYSTAL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL; software used to prepare material for publication: KRYSTAL.
[Sn3(C4H9)9(C3H5O5P)] | F(000) = 1064 |
Mr = 1036.20 | Dx = 1.424 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2y1 | Cell parameters from 6517 reflections |
a = 10.2144 (7) Å | θ = 1.9–29.8° |
b = 18.018 (1) Å | µ = 1.61 mm−1 |
c = 13.1304 (9) Å | T = 120 K |
β = 90.177 (1)° | Needle, colourless |
V = 2416.6 (2) Å3 | 0.47 × 0.16 × 0.15 mm |
Z = 2 |
Siemens SMART CCD diffractometer | 13624 independent reflections |
Radiation source: x-ray tube | 12628 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω rotation scans with narrow frames | θmax = 29.8°, θmin = 1.9° |
Absorption correction: integration (XPREP; Siemens, 1995) | h = −14→14 |
Tmin = 0.501, Tmax = 0.799 | k = −25→25 |
28299 measured reflections | l = −18→18 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | Weighting scheme based on measured s.u.'s |
R[F2 > 2σ(F2)] = 0.029 | (Δ/σ)max = 0.002 |
wR(F2) = 0.071 | Δρmax = 2.2 (1) e Å−3 |
S = 1.12 | Δρmin = −1.1 (1) e Å−3 |
12628 reflections | Extinction correction: B-C type 1 Lorentzian isotropic Becker and Coppens (1974) |
431 parameters | Extinction coefficient: 56 (6) |
0 restraints | Absolute structure: Rogers (1981) |
0 constraints | Rogers parameter: 0.73 (3) |
[Sn3(C4H9)9(C3H5O5P)] | V = 2416.6 (2) Å3 |
Mr = 1036.20 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.2144 (7) Å | µ = 1.61 mm−1 |
b = 18.018 (1) Å | T = 120 K |
c = 13.1304 (9) Å | 0.47 × 0.16 × 0.15 mm |
β = 90.177 (1)° |
Siemens SMART CCD diffractometer | 13624 independent reflections |
Absorption correction: integration (XPREP; Siemens, 1995) | 12628 reflections with I > 2σ(I) |
Tmin = 0.501, Tmax = 0.799 | Rint = 0.032 |
28299 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.071 | Δρmax = 2.2 (1) e Å−3 |
S = 1.12 | Δρmin = −1.1 (1) e Å−3 |
12628 reflections | Absolute structure: Rogers (1981) |
431 parameters | Rogers parameter: 0.73 (3) |
0 restraints |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | −0.13286 (2) | −0.07770 | 0.57743 (2) | 0.0182 (1) | |
Sn2 | −0.30283 (2) | 0.21062 (2) | 0.50253 (2) | 0.0215 (1) | |
Sn3 | 0.31729 (2) | −0.09175 (2) | 0.83472 (2) | 0.0299 (1) | |
P1 | 0.19697 (8) | −0.12219 (5) | 0.60470 (7) | 0.0196 (4) | |
O1 | 0.0614 (2) | −0.1294 (1) | 0.5600 (2) | 0.022 (1) | |
O2 | 0.1898 (2) | −0.1193 (1) | 0.7220 (2) | 0.028 (1) | |
O3 | −0.2918 (2) | 0.3182 (1) | 0.4305 (2) | 0.027 (1) | |
O4 | −0.3164 (2) | 0.0881 (2) | 0.5750 (2) | 0.036 (2) | |
O5 | −0.3427 (2) | −0.0341 (1) | 0.5918 (2) | 0.026 (1) | |
N1 | −0.6002 (3) | −0.0286 (2) | 0.6094 (2) | 0.022 (1) | |
C1 | −0.7312 (3) | −0.0352 (2) | 0.5655 (3) | 0.023 (2) | |
C2 | −0.5328 (3) | 0.0392 (2) | 0.5792 (3) | 0.026 (2) | |
C3 | −0.3847 (3) | 0.0316 (2) | 0.5827 (3) | 0.024 (2) | |
C4 | −0.1346 (4) | −0.0412 (2) | 0.4220 (3) | 0.031 (2) | |
C5 | −0.0060 (4) | −0.0422 (2) | 0.3657 (3) | 0.030 (2) | |
C6 | −0.0137 (4) | −0.0197 (3) | 0.2546 (3) | 0.038 (2) | |
C7 | 0.1156 (6) | −0.0221 (4) | 0.2006 (4) | 0.066 (4) | |
C8 | −0.2155 (4) | −0.1841 (2) | 0.6090 (3) | 0.028 (2) | |
C9 | −0.1506 (5) | −0.2296 (2) | 0.6932 (3) | 0.043 (3) | |
C10 | −0.2206 (7) | −0.3041 (3) | 0.7136 (4) | 0.060 (3) | |
C11 | −0.2168 (8) | −0.3563 (3) | 0.6241 (4) | 0.074 (4) | |
C12 | −0.0736 (3) | −0.0043 (2) | 0.6973 (3) | 0.024 (2) | |
C13 | −0.1255 (4) | −0.0237 (2) | 0.8011 (3) | 0.033 (2) | |
C14 | −0.0780 (5) | 0.0294 (2) | 0.8843 (3) | 0.039 (2) | |
C15 | −0.1311 (6) | 0.0117 (3) | 0.9892 (4) | 0.057 (3) | |
C28 | 0.3272 (4) | 0.0264 (3) | 0.8453 (3) | 0.036 (2) | |
C29 | 0.4670 (4) | 0.0560 (3) | 0.8529 (3) | 0.036 (2) | |
C30 | 0.4757 (4) | 0.1401 (3) | 0.8617 (3) | 0.038 (2) | |
C31 | 0.6140 (5) | 0.1687 (3) | 0.8683 (4) | 0.048 (3) | |
C32 | 0.2067 (4) | −0.1373 (3) | 0.9587 (3) | 0.049 (3) | |
C33 | 0.1218 (5) | −0.2050 (3) | 0.9344 (3) | 0.044 (2) | |
C34 | 0.0431 (5) | −0.2332 (3) | 1.0246 (4) | 0.050 (3) | |
C35 | −0.0500 (6) | −0.2948 (3) | 0.9959 (5) | 0.064 (3) | |
C36 | 0.4932 (4) | −0.1521 (3) | 0.8063 (3) | 0.038 (2) | |
C37 | 0.5532 (4) | −0.1851 (3) | 0.9027 (4) | 0.046 (3) | |
C38 | 0.5912 (4) | −0.1273 (3) | 0.9807 (4) | 0.049 (3) | |
C39 | 0.6601 (5) | −0.1593 (4) | 1.0756 (4) | 0.060 (3) | |
C16A | −0.1080 (6) | 0.2113 (4) | 0.5524 (5) | 0.023 (1)* | 0.5 |
C17A | −0.0853 (8) | 0.2412 (5) | 0.6615 (6) | 0.035 (2)* | 0.5 |
C18A | 0.0576 (9) | 0.2530 (5) | 0.6888 (7) | 0.036 (2)* | 0.5 |
C19A | 0.1390 (11) | 0.1812 (6) | 0.6870 (8) | 0.045 (2)* | 0.5 |
C16B | −0.1416 (7) | 0.2177 (4) | 0.6106 (6) | 0.026 (1)* | 0.5 |
C17B | −0.0114 (7) | 0.1865 (4) | 0.5743 (6) | 0.030 (2)* | 0.5 |
C18B | 0.0952 (9) | 0.1819 (5) | 0.6554 (7) | 0.036 (2)* | 0.5 |
C19B | 0.1342 (9) | 0.2552 (5) | 0.7019 (7) | 0.040 (2)* | 0.5 |
C20A | −0.4723 (7) | 0.2447 (4) | 0.5967 (6) | 0.028 (1)* | 0.5 |
C21A | −0.5072 (8) | 0.3270 (5) | 0.6109 (7) | 0.029 (2)* | 0.5 |
C22A | −0.4129 (9) | 0.3695 (6) | 0.6732 (7) | 0.038 (2)* | 0.5 |
C23A | −0.4619 (11) | 0.4476 (7) | 0.6923 (8) | 0.047 (2)* | 0.5 |
C20B | −0.4934 (7) | 0.2268 (4) | 0.5567 (6) | 0.027 (1)* | 0.5 |
C21B | −0.5302 (7) | 0.3061 (4) | 0.5826 (6) | 0.026 (1)* | 0.5 |
C22B | −0.4495 (9) | 0.3388 (5) | 0.6649 (7) | 0.038 (2)* | 0.5 |
C23B | −0.4921 (12) | 0.4160 (7) | 0.6968 (9) | 0.058 (3)* | 0.5 |
C24A | −0.3607 (7) | 0.1559 (4) | 0.3663 (6) | 0.029 (2)* | 0.5 |
C25A | −0.2686 (9) | 0.1644 (5) | 0.2777 (7) | 0.038 (2)* | 0.5 |
C26A | −0.2941 (10) | 0.1114 (5) | 0.1893 (8) | 0.044 (2)* | 0.5 |
C27A | −0.4311 (11) | 0.1159 (6) | 0.1500 (9) | 0.053 (2)* | 0.5 |
C24B | −0.2683 (8) | 0.1580 (4) | 0.3582 (6) | 0.032 (2)* | 0.5 |
C25B | −0.3963 (8) | 0.1339 (5) | 0.3045 (6) | 0.035 (2)* | 0.5 |
C26B | −0.3716 (10) | 0.1032 (5) | 0.1964 (7) | 0.042 (2)* | 0.5 |
C27B | −0.5017 (9) | 0.0884 (5) | 0.1455 (7) | 0.042 (2)* | 0.5 |
HN1 | −0.5496 | −0.0699 | 0.5879 | 0.027* | |
H1a | −0.7256 | −0.0338 | 0.4933 | 0.028* | |
H1b | −0.7841 | 0.0047 | 0.5885 | 0.028* | |
H2a | −0.5579 | 0.0780 | 0.6241 | 0.031* | |
H2b | −0.5583 | 0.0514 | 0.5117 | 0.031* | |
H4a | −0.1660 | 0.0084 | 0.4213 | 0.037* | |
H4b | −0.1938 | −0.0722 | 0.3857 | 0.037* | |
H5a | 0.0281 | −0.0913 | 0.3689 | 0.036* | |
H5b | 0.0523 | −0.0092 | 0.3993 | 0.036* | |
H6a | −0.0466 | 0.0296 | 0.2510 | 0.046* | |
H6b | −0.0723 | −0.0523 | 0.2207 | 0.046* | |
H7a | 0.1108 | −0.0079 | 0.1310 | 0.079* | |
H7b | 0.1485 | −0.0713 | 0.2042 | 0.079* | |
H7c | 0.1743 | 0.0106 | 0.2345 | 0.079* | |
H8a | −0.2118 | −0.2124 | 0.5480 | 0.034* | |
H8b | −0.3043 | −0.1766 | 0.6276 | 0.034* | |
H9a | −0.1509 | −0.2013 | 0.7542 | 0.052* | |
H9b | −0.0628 | −0.2397 | 0.6739 | 0.052* | |
H10a | −0.3095 | −0.2942 | 0.7297 | 0.073* | |
H10b | −0.1793 | −0.3276 | 0.7700 | 0.073* | |
H11a | −0.2599 | −0.4021 | 0.6367 | 0.089* | |
H11b | −0.1279 | −0.3662 | 0.6080 | 0.089* | |
H11c | −0.2581 | −0.3328 | 0.5678 | 0.089* | |
H12a | −0.1031 | 0.0442 | 0.6807 | 0.028* | |
H12b | 0.0193 | −0.0046 | 0.7008 | 0.028* | |
H13a | −0.0977 | −0.0725 | 0.8179 | 0.040* | |
H13b | −0.2185 | −0.0221 | 0.7988 | 0.040* | |
H14a | −0.1045 | 0.0783 | 0.8666 | 0.047* | |
H14b | 0.0148 | 0.0271 | 0.8871 | 0.047* | |
H15a | −0.1016 | 0.0447 | 1.0409 | 0.069* | |
H15b | −0.1047 | −0.0372 | 1.0070 | 0.069* | |
H15c | −0.2240 | 0.0140 | 0.9864 | 0.069* | |
H28a | 0.2805 | 0.0416 | 0.9042 | 0.044* | |
H28b | 0.2871 | 0.0470 | 0.7864 | 0.044* | |
H29a | 0.5132 | 0.0411 | 0.7937 | 0.043* | |
H29b | 0.5072 | 0.0348 | 0.9114 | 0.043* | |
H30a | 0.4302 | 0.1551 | 0.9213 | 0.046* | |
H30b | 0.4350 | 0.1615 | 0.8035 | 0.046* | |
H31a | 0.6195 | 0.2212 | 0.8738 | 0.057* | |
H31b | 0.6595 | 0.1537 | 0.8087 | 0.057* | |
H31c | 0.6547 | 0.1474 | 0.9265 | 0.057* | |
H32a | 0.1508 | −0.0994 | 0.9835 | 0.058* | |
H32b | 0.2670 | −0.1513 | 1.0105 | 0.058* | |
H33a | 0.1772 | −0.2439 | 0.9116 | 0.052* | |
H33b | 0.0624 | −0.1920 | 0.8815 | 0.052* | |
H34a | −0.0060 | −0.1931 | 1.0518 | 0.061* | |
H34b | 0.1022 | −0.2513 | 1.0749 | 0.061* | |
H35a | −0.0991 | −0.3124 | 1.0523 | 0.076* | |
H35b | −0.0009 | −0.3349 | 0.9687 | 0.076* | |
H35c | −0.1090 | −0.2768 | 0.9457 | 0.076* | |
H36a | 0.5551 | −0.1195 | 0.7763 | 0.046* | |
H36b | 0.4740 | −0.1914 | 0.7603 | 0.046* | |
H37a | 0.6294 | −0.2121 | 0.8843 | 0.055* | |
H37b | 0.4913 | −0.2178 | 0.9326 | 0.055* | |
H38a | 0.5141 | −0.1024 | 1.0022 | 0.059* | |
H38b | 0.6487 | −0.0928 | 0.9493 | 0.059* | |
H39a | 0.6840 | −0.1229 | 1.1247 | 0.072* | |
H39b | 0.7373 | −0.1841 | 1.0541 | 0.072* | |
H39c | 0.6027 | −0.1938 | 1.1070 | 0.072* | |
H16Aa | −0.0591 | 0.2413 | 0.5068 | 0.027* | 0.5 |
H16Ab | −0.0764 | 0.1617 | 0.5500 | 0.027* | 0.5 |
H17Aa | −0.1214 | 0.2067 | 0.7084 | 0.042* | 0.5 |
H17Ab | −0.1294 | 0.2874 | 0.6677 | 0.042* | 0.5 |
H18Aa | 0.0622 | 0.2735 | 0.7554 | 0.044* | 0.5 |
H18Ab | 0.0943 | 0.2869 | 0.6414 | 0.044* | 0.5 |
H19Aa | 0.2285 | 0.1885 | 0.7041 | 0.054* | 0.5 |
H19Ab | 0.1344 | 0.1606 | 0.6204 | 0.054* | 0.5 |
H19Ac | 0.1023 | 0.1472 | 0.7344 | 0.054* | 0.5 |
H16Ba | −0.1661 | 0.1913 | 0.6702 | 0.032* | 0.5 |
H16Bb | −0.1288 | 0.2685 | 0.6269 | 0.032* | 0.5 |
H17Ba | 0.0196 | 0.2173 | 0.5208 | 0.036* | 0.5 |
H17Bb | −0.0264 | 0.1378 | 0.5489 | 0.036* | 0.5 |
H18Ba | 0.1707 | 0.1605 | 0.6252 | 0.043* | 0.5 |
H18Bb | 0.0646 | 0.1506 | 0.7084 | 0.043* | 0.5 |
H19Ba | 0.2006 | 0.2523 | 0.7525 | 0.048* | 0.5 |
H19Bb | 0.0586 | 0.2766 | 0.7320 | 0.048* | 0.5 |
H19Bc | 0.1647 | 0.2865 | 0.6488 | 0.048* | 0.5 |
H20Aa | −0.4573 | 0.2252 | 0.6629 | 0.034* | 0.5 |
H20Ab | −0.5472 | 0.2217 | 0.5676 | 0.034* | 0.5 |
H21Aa | −0.5904 | 0.3298 | 0.6427 | 0.035* | 0.5 |
H21Ab | −0.5118 | 0.3494 | 0.5454 | 0.035* | 0.5 |
H22Aa | −0.3316 | 0.3719 | 0.6385 | 0.045* | 0.5 |
H22AB | −0.4011 | 0.3451 | 0.7367 | 0.045* | 0.5 |
H23Aa | −0.4013 | 0.4750 | 0.7324 | 0.056* | 0.5 |
H23Ab | −0.5432 | 0.4452 | 0.7270 | 0.056* | 0.5 |
H23Ac | −0.4737 | 0.4721 | 0.6288 | 0.056* | 0.5 |
H20Ba | −0.5033 | 0.1978 | 0.6166 | 0.032* | 0.5 |
H20Bb | −0.5525 | 0.2097 | 0.5059 | 0.032* | 0.5 |
H21Ba | −0.6192 | 0.3068 | 0.6034 | 0.032* | 0.5 |
H21Bb | −0.5203 | 0.3356 | 0.5232 | 0.032* | 0.5 |
H22Ba | −0.3615 | 0.3414 | 0.6419 | 0.046* | 0.5 |
H22Bb | −0.4542 | 0.3071 | 0.7226 | 0.046* | 0.5 |
H23Ba | −0.4403 | 0.4370 | 0.7496 | 0.070* | 0.5 |
H23Bb | −0.5801 | 0.4134 | 0.7197 | 0.070* | 0.5 |
H23Bc | −0.4874 | 0.4476 | 0.6391 | 0.070* | 0.5 |
H24Aa | −0.4436 | 0.1751 | 0.3464 | 0.035* | 0.5 |
H24Ab | −0.3687 | 0.1044 | 0.3808 | 0.035* | 0.5 |
H25Aa | −0.1820 | 0.1562 | 0.3016 | 0.046* | 0.5 |
H25Ab | −0.2761 | 0.2137 | 0.2528 | 0.046* | 0.5 |
H26Aa | −0.2779 | 0.0621 | 0.2118 | 0.053* | 0.5 |
H26Ab | −0.2358 | 0.1233 | 0.1354 | 0.053* | 0.5 |
H27Aa | −0.4470 | 0.0829 | 0.0949 | 0.064* | 0.5 |
H27Ab | −0.4473 | 0.1652 | 0.1275 | 0.064* | 0.5 |
H27Ac | −0.4894 | 0.1040 | 0.2038 | 0.064* | 0.5 |
H24Ba | −0.2154 | 0.1153 | 0.3690 | 0.039* | 0.5 |
H24Bb | −0.2233 | 0.1919 | 0.3153 | 0.039* | 0.5 |
H25Ba | −0.4527 | 0.1757 | 0.2995 | 0.042* | 0.5 |
H25Bb | −0.4371 | 0.0964 | 0.3441 | 0.042* | 0.5 |
H26Ba | −0.3231 | 0.0583 | 0.2008 | 0.050* | 0.5 |
H26Bb | −0.3238 | 0.1385 | 0.1578 | 0.050* | 0.5 |
H27Ba | −0.4865 | 0.0695 | 0.0790 | 0.051* | 0.5 |
H27Bb | −0.5502 | 0.1333 | 0.1411 | 0.051* | 0.5 |
H27Bc | −0.5496 | 0.0531 | 0.1841 | 0.051* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0147 (1) | 0.0171 (1) | 0.0229 (1) | −0.0012 (1) | 0.0029 (1) | −0.0022 (1) |
Sn2 | 0.0174 (1) | 0.0239 (1) | 0.0230 (1) | −0.0053 (1) | −0.0003 (1) | 0.0019 (1) |
Sn3 | 0.0197 (1) | 0.0451 (2) | 0.0248 (1) | 0.0025 (1) | 0.0001 (1) | 0.0022 (1) |
P1 | 0.0154 (3) | 0.0194 (4) | 0.0242 (4) | 0.0031 (3) | 0.0035 (3) | 0.0010 (3) |
O1 | 0.017 (1) | 0.021 (1) | 0.029 (1) | 0.003 (1) | 0.003 (1) | 0.000 (1) |
O2 | 0.022 (1) | 0.036 (1) | 0.025 (1) | −0.002 (1) | 0.003 (1) | 0.002 (1) |
O3 | 0.021 (1) | 0.023 (1) | 0.037 (1) | −0.006 (1) | 0.006 (1) | 0.002 (1) |
O4 | 0.020 (1) | 0.034 (1) | 0.053 (2) | −0.003 (1) | 0.002 (1) | 0.021 (1) |
O5 | 0.016 (1) | 0.029 (1) | 0.035 (1) | 0.004 (1) | 0.004 (1) | −0.003 (1) |
N1 | 0.013 (1) | 0.025 (1) | 0.029 (2) | 0.000 (1) | 0.002 (1) | 0.007 (1) |
C1 | 0.017 (1) | 0.023 (2) | 0.030 (2) | 0.001 (1) | −0.001 (1) | 0.006 (1) |
C2 | 0.017 (1) | 0.029 (2) | 0.032 (2) | 0.000 (1) | 0.002 (1) | 0.010 (1) |
C3 | 0.017 (1) | 0.035 (2) | 0.019 (2) | 0.000 (1) | 0.004 (1) | 0.008 (1) |
C4 | 0.027 (2) | 0.041 (2) | 0.026 (2) | 0.010 (1) | −0.002 (1) | −0.001 (2) |
C5 | 0.025 (2) | 0.043 (2) | 0.022 (2) | −0.002 (1) | 0.001 (1) | 0.005 (2) |
C6 | 0.046 (2) | 0.046 (2) | 0.022 (2) | 0.000 (2) | 0.000 (2) | 0.002 (2) |
C7 | 0.049 (3) | 0.121 (6) | 0.028 (3) | −0.022 (3) | 0.004 (2) | 0.002 (3) |
C8 | 0.028 (2) | 0.025 (2) | 0.033 (2) | −0.007 (1) | 0.007 (1) | −0.007 (1) |
C9 | 0.074 (3) | 0.026 (2) | 0.029 (2) | −0.019 (2) | 0.002 (2) | 0.000 (2) |
C10 | 0.109 (5) | 0.041 (3) | 0.032 (2) | −0.040 (3) | 0.000 (3) | 0.006 (2) |
C11 | 0.155 (7) | 0.024 (2) | 0.042 (3) | −0.028 (3) | −0.003 (3) | 0.002 (2) |
C12 | 0.019 (1) | 0.023 (2) | 0.030 (2) | 0.001 (1) | −0.001 (1) | −0.004 (1) |
C13 | 0.040 (2) | 0.029 (2) | 0.031 (2) | −0.003 (2) | 0.000 (2) | −0.002 (2) |
C14 | 0.054 (3) | 0.038 (2) | 0.026 (2) | −0.008 (2) | −0.002 (2) | −0.006 (2) |
C15 | 0.086 (4) | 0.055 (3) | 0.030 (2) | −0.019 (3) | −0.004 (2) | −0.006 (2) |
C28 | 0.027 (2) | 0.052 (3) | 0.031 (2) | 0.005 (2) | −0.001 (2) | −0.003 (2) |
C29 | 0.027 (2) | 0.052 (2) | 0.030 (2) | −0.001 (2) | −0.003 (2) | 0.004 (2) |
C30 | 0.035 (2) | 0.049 (2) | 0.031 (2) | 0.001 (2) | −0.003 (2) | 0.007 (2) |
C31 | 0.047 (3) | 0.051 (3) | 0.046 (3) | −0.009 (2) | −0.007 (2) | 0.006 (2) |
C32 | 0.034 (2) | 0.087 (4) | 0.026 (2) | −0.005 (2) | 0.004 (2) | 0.003 (2) |
C33 | 0.052 (3) | 0.044 (2) | 0.035 (2) | 0.012 (2) | 0.017 (2) | 0.009 (2) |
C34 | 0.036 (2) | 0.075 (3) | 0.041 (3) | 0.007 (2) | 0.006 (2) | 0.019 (2) |
C35 | 0.072 (4) | 0.050 (3) | 0.069 (3) | 0.005 (3) | 0.020 (3) | 0.024 (3) |
C36 | 0.029 (2) | 0.049 (2) | 0.037 (2) | 0.006 (2) | 0.001 (2) | 0.007 (2) |
C37 | 0.032 (2) | 0.051 (3) | 0.055 (3) | 0.007 (2) | −0.002 (2) | 0.020 (2) |
C38 | 0.032 (2) | 0.071 (3) | 0.045 (3) | −0.009 (2) | −0.007 (2) | 0.022 (2) |
C39 | 0.041 (3) | 0.094 (4) | 0.047 (3) | 0.005 (3) | −0.004 (2) | 0.027 (3) |
Sn1—C4 | 2.144 (4) | C13—H13a | 0.950 |
Sn1—C8 | 2.135 (4) | C13—H13b | 0.950 |
Sn1—C12 | 2.142 (3) | C14—H14a | 0.950 |
Sn1—O1 | 2.205 (2) | C14—H14b | 0.950 |
Sn1—O5 | 2.292 (2) | C15—H15a | 0.950 |
Sn2—C16A | 2.093 (6) | C15—H15b | 0.950 |
Sn2—C20A | 2.217 (8) | C15—H15c | 0.950 |
Sn2—C24A | 2.124 (8) | C28—H28a | 0.950 |
Sn2—C16B | 2.174 (7) | C28—H28b | 0.950 |
Sn2—C20B | 2.095 (7) | C29—H29a | 0.950 |
Sn2—C24B | 2.149 (8) | C29—H29b | 0.950 |
Sn2—O3 | 2.160 (3) | C30—H30a | 0.950 |
Sn2—O4 | 2.408 (3) | C30—H30b | 0.950 |
Sn3—C28 | 2.136 (5) | C31—H31a | 0.950 |
Sn3—C32 | 2.147 (5) | C31—H31b | 0.950 |
Sn3—C36 | 2.134 (4) | C31—H31c | 0.950 |
Sn3—O2 | 2.030 (3) | C32—H32a | 0.950 |
P1—O1 | 1.508 (2) | C32—H32b | 0.950 |
P1—O2 | 1.543 (3) | C33—H33a | 0.950 |
P1—O3i | 1.519 (2) | C33—H33b | 0.950 |
P1—C1ii | 1.806 (3) | C34—H34a | 0.950 |
N1—C1 | 1.460 (4) | C34—H34b | 0.950 |
N1—C2 | 1.458 (4) | C35—H35a | 0.950 |
C2—C3 | 1.519 (4) | C35—H35b | 0.950 |
O4—C3 | 1.239 (4) | C35—H35c | 0.950 |
O5—C3 | 1.263 (4) | C36—H36a | 0.950 |
C4—C5 | 1.510 (5) | C36—H36b | 0.950 |
C5—C6 | 1.517 (5) | C37—H37a | 0.950 |
C6—C7 | 1.501 (7) | C37—H37b | 0.950 |
C8—C9 | 1.527 (6) | C38—H38a | 0.950 |
C9—C10 | 1.545 (6) | C38—H38b | 0.950 |
C10—C11 | 1.505 (7) | C39—H39a | 0.950 |
C12—C13 | 1.505 (5) | C39—H39b | 0.950 |
C13—C14 | 1.530 (6) | C39—H39c | 0.950 |
C14—C15 | 1.516 (7) | C16A—H16Aa | 0.950 |
C28—C29 | 1.527 (6) | C16A—H16Ab | 0.950 |
C29—C30 | 1.522 (7) | C17A—H17Aa | 0.950 |
C30—C31 | 1.506 (6) | C17A—H17Ab | 0.950 |
C32—C33 | 1.530 (7) | C18A—H18Aa | 0.950 |
C33—C34 | 1.521 (6) | C18A—H18Ab | 0.950 |
C34—C35 | 1.509 (8) | C19A—H19Aa | 0.950 |
C36—C37 | 1.525 (6) | C19A—H19Ab | 0.950 |
C37—C38 | 1.510 (8) | C19A—H19Ac | 0.950 |
C38—C39 | 1.540 (7) | C16B—H16Ba | 0.950 |
C16A—C17A | 1.548 (11) | C16B—H16Bb | 0.950 |
C17A—C18A | 1.517 (12) | C17B—H17Ba | 0.950 |
C18A—C19A | 1.538 (14) | C17B—H17Bb | 0.950 |
C16B—C17B | 1.522 (10) | C18B—H18Ba | 0.950 |
C17B—C18B | 1.522 (12) | C18B—H18Bb | 0.950 |
C18B—C19B | 1.508 (13) | C19B—H19Ba | 0.950 |
C20A—C21A | 1.536 (11) | C19B—H19Bb | 0.950 |
C21A—C22A | 1.477 (13) | C19B—H19Bc | 0.950 |
C22A—C23A | 1.515 (15) | C20A—H20Aa | 0.950 |
C20B—C21B | 1.515 (11) | C20A—H20Ab | 0.950 |
C21B—C22B | 1.480 (12) | C21A—H21Aa | 0.950 |
C22B—C23B | 1.518 (16) | C21A—H21Ab | 0.950 |
C24A—C25A | 1.507 (12) | C22A—H22Aa | 0.950 |
C25A—C26A | 1.524 (13) | C22A—H22AB | 0.950 |
C26A—C27A | 1.493 (14) | C23A—H23Aa | 0.950 |
C24B—C25B | 1.546 (11) | C23A—H23Ab | 0.950 |
C25B—C26B | 1.544 (13) | C23A—H23Ac | 0.950 |
C26B—C27B | 1.509 (13) | C20B—H20Ba | 0.950 |
N1—HN1 | 0.950 | C20B—H20Bb | 0.950 |
C1—H1a | 0.950 | C21B—H21Ba | 0.950 |
C1—H1b | 0.950 | C21B—H21Bb | 0.950 |
C2—H2a | 0.950 | C22B—H22Ba | 0.950 |
C2—H2b | 0.950 | C22B—H22Bb | 0.950 |
C4—H4a | 0.950 | C23B—H23Bc | 0.950 |
C4—H4b | 0.950 | C24A—H24Aa | 0.950 |
C5—H5a | 0.950 | C24A—H24Ab | 0.950 |
C5—H5b | 0.950 | C25A—H25Aa | 0.950 |
C6—H6a | 0.950 | C25A—H25Ab | 0.950 |
C6—H6b | 0.950 | C26A—H26Aa | 0.950 |
C7—H7a | 0.950 | C26A—H26Ab | 0.950 |
C7—H7b | 0.950 | C27A—H27Aa | 0.950 |
C7—H7c | 0.950 | C27A—H27Ab | 0.950 |
C8—H8a | 0.950 | C27A—H27Ac | 0.950 |
C8—H8b | 0.950 | C24B—H24Ba | 0.950 |
C9—H9a | 0.950 | C24B—H24Bb | 0.950 |
C9—H9b | 0.950 | C25B—H25Ba | 0.950 |
C10—H10a | 0.950 | C25B—H25Bb | 0.950 |
C10—H10b | 0.950 | C26B—H26Ba | 0.950 |
C11—H11a | 0.950 | C26B—H26Bb | 0.950 |
C11—H11b | 0.950 | C27B—H27Ba | 0.950 |
C11—H11c | 0.950 | C27B—H27Bb | 0.950 |
C12—H12a | 0.950 | C27B—H27Bc | 0.950 |
C12—H12b | 0.950 | ||
C4—Sn1—C8 | 117.2 (2) | C14—C15—H15a | 113.8 |
C4—Sn1—C12 | 120.8 (1) | H15b—C15—H15c | 109.5 |
C4—Sn1—O1 | 92.0 (1) | C14—C15—H15b | 108.4 |
C4—Sn1—O5 | 88.2 (1) | C14—C15—H15c | 108.4 |
C8—Sn1—C12 | 121.5 (1) | H28a—C28—H28b | 109.5 |
C8—Sn1—O1 | 89.8 (1) | C29—C28—H28a | 108.5 |
C8—Sn1—O5 | 85.5 (1) | C29—C28—H28b | 108.5 |
O1—Sn1—C12 | 94.9 (1) | H29a—C29—H29b | 109.5 |
O1—Sn1—O5 | 174.85 (9) | C30—C29—H29a | 108.3 |
O5—Sn1—C12 | 89.4 (1) | C28—C29—H29a | 108.3 |
C16A—Sn2—C20A | 124.5 (3) | C30—C29—H29b | 108.3 |
C16A—Sn2—C24A | 121.9 (3) | C28—C29—H29b | 108.3 |
C20A—Sn2—C24A | 112.5 (3) | H30a—C30—H30b | 109.5 |
O3—Sn2—C16A | 94.6 (2) | C31—C30—H30a | 108.4 |
O3—Sn2—C20A | 92.1 (2) | C29—C30—H30a | 108.4 |
O3—Sn2—C24A | 93.6 (2) | C31—C30—H30b | 108.4 |
O4—Sn2—C16A | 86.4 (2) | C29—C30—H30b | 108.4 |
O4—Sn2—C20A | 89.3 (2) | H31a—C31—H31b | 108.4 |
O4—Sn2—C24A | 83.7 (2) | H31a—C31—H31c | 108.4 |
O3—Sn2—O4 | 177.3 (1) | C30—C31—H31a | 113.5 |
C16B—Sn2—C20B | 118.2 (3) | H31b—C31—H31c | 109.5 |
C16B—Sn2—C24B | 118.4 (3) | C30—C31—H31b | 108.4 |
C20B—Sn2—C24B | 121.1 (3) | C30—C31—H31c | 108.4 |
O3—Sn2—C16B | 101.1 (2) | H32a—C32—H32b | 109.5 |
O3—Sn2—C20B | 94.2 (2) | C33—C32—H32a | 107.7 |
O3—Sn2—C24B | 90.1 (2) | C33—C32—H32b | 107.7 |
O4—Sn2—C16B | 80.8 (2) | H33a—C33—H33b | 109.5 |
O4—Sn2—C20B | 86.5 (2) | C34—C33—H33a | 108.4 |
O4—Sn2—C24B | 87.4 (2) | C32—C33—H33a | 108.4 |
C28—Sn3—C32 | 110.9 (2) | C34—C33—H33b | 108.4 |
C28—Sn3—C36 | 118.7 (2) | C32—C33—H33b | 108.4 |
C32—Sn3—C36 | 112.5 (2) | H34a—C34—H34b | 109.5 |
O2—Sn3—C28 | 108.8 (1) | C35—C34—H34a | 108.7 |
O2—Sn3—C32 | 97.0 (1) | C33—C34—H34a | 108.7 |
O2—Sn3—C36 | 106.6 (1) | C35—C34—H34b | 108.7 |
Sn1—C4—C5 | 117.2 (2) | C33—C34—H34b | 108.7 |
Sn1—C8—C9 | 116.9 (3) | H35a—C35—H35b | 108.7 |
Sn1—C12—C13 | 115.0 (2) | H35a—C35—H35c | 108.7 |
Sn1—O1—P1 | 138.5 (1) | C34—C35—H35a | 112.7 |
Sn1—O5—C3 | 129.1 (2) | H35b—C35—H35c | 109.5 |
Sn2—C16A—C17A | 115.5 (5) | C34—C35—H35b | 108.7 |
Sn2—C20A—C21A | 121.1 (5) | C34—C35—H35c | 108.7 |
Sn2—C24A—C25A | 115.5 (5) | H36a—C36—H36b | 109.5 |
Sn2—O3—P1iii | 143.3 (2) | C37—C36—H36a | 108.6 |
Sn2—O4—C3 | 145.0 (2) | C37—C36—H36b | 108.6 |
Sn2—C16B—C17B | 115.8 (5) | H37a—C37—H37b | 109.5 |
Sn2—C20B—C21B | 116.1 (5) | C38—C37—H37a | 108.5 |
Sn2—C24B—C25B | 112.7 (5) | C36—C37—H37a | 108.5 |
Sn3—C28—C29 | 113.4 (3) | C38—C37—H37b | 108.5 |
Sn3—C32—C33 | 116.5 (3) | C36—C37—H37b | 108.5 |
Sn3—C36—C37 | 113.0 (3) | H38a—C38—H38b | 109.5 |
Sn3—O2—P1 | 134.7 (2) | C37—C38—H38a | 108.3 |
O1—P1—O3i | 113.9 (1) | C39—C38—H38a | 108.3 |
O1—P1—O2 | 110.2 (1) | C37—C38—H38b | 108.3 |
O1—P1—C1ii | 109.7 (1) | C39—C38—H38b | 108.3 |
O2—P1—O3i | 111.1 (2) | H39a—C39—H39b | 108.3 |
O3i—P1—C1ii | 105.5 (2) | H39a—C39—H39c | 108.3 |
O2—P1—C1ii | 106.0 (2) | C38—C39—H39a | 114.0 |
C1—N1—C2 | 113.2 (3) | H39b—C39—H39c | 109.5 |
P1iv—C1—N1 | 109.3 (2) | C38—C39—H39b | 108.3 |
N1—C2—C3 | 112.8 (3) | C38—C39—H39c | 108.3 |
O4—C3—O5 | 125.9 (3) | H16Aa—C16A—H16Ab | 109.5 |
O4—C3—C2 | 118.9 (3) | C17A—C16A—H16Aa | 107.9 |
O5—C3—C2 | 115.2 (3) | C17A—C16A—H16Ab | 107.9 |
C4—C5—C6 | 115.2 (3) | H17Aa—C17A—H17Ab | 109.5 |
C5—C6—C7 | 113.8 (4) | C18A—C17A—H17Aa | 108.3 |
C8—C9—C10 | 113.1 (4) | C16A—C17A—H17Aa | 108.3 |
C9—C10—C11 | 113.2 (4) | C18A—C17A—H17Ab | 108.3 |
C12—C13—C14 | 112.9 (3) | C16A—C17A—H17Ab | 108.3 |
C13—C14—C15 | 113.8 (4) | H18Aa—C18A—H18Ab | 109.5 |
C28—C29—C30 | 114.0 (4) | C17A—C18A—H18Aa | 108.5 |
C29—C30—C31 | 113.6 (4) | C19A—C18A—H18Aa | 108.5 |
C32—C33—C34 | 113.9 (4) | C17A—C18A—H18Ab | 108.5 |
C33—C34—C35 | 112.7 (5) | C19A—C18A—H18Ab | 108.5 |
C36—C37—C38 | 113.4 (4) | H19Aa—C19A—H19Ab | 108.5 |
C37—C38—C39 | 114.0 (5) | H19Aa—C19A—H19Ac | 108.5 |
C16A—C17A—C18A | 114.1 (7) | H19Ab—C19A—H19Ac | 109.5 |
C17A—C18A—C19A | 113.5 (8) | C18A—C19A—H19Aa | 113.5 |
C20A—C21A—C22A | 114.6 (7) | C18A—C19A—H19Ab | 108.5 |
C21A—C22A—C23A | 111.0 (8) | C18A—C19A—H19Ac | 108.5 |
C24A—C25A—C26A | 114.8 (7) | H16Ba—C16B—H16Bb | 109.5 |
C25A—C26A—C27A | 112.8 (8) | C17B—C16B—H16Ba | 107.9 |
C16B—C17B—C18B | 115.1 (7) | C17B—C16B—H16Bb | 107.9 |
C17B—C18B—C19B | 115.0 (7) | H17Ba—C17B—H17Bb | 109.5 |
C20B—C21B—C22B | 113.6 (7) | C16B—C17B—H17Ba | 108.0 |
C21B—C22B—C23B | 114.0 (8) | C18B—C17B—H17Ba | 108.0 |
C24B—C25B—C26B | 112.3 (7) | C16B—C17B—H17Bb | 108.0 |
C25B—C26B—C27B | 109.0 (8) | C18B—C17B—H17Bb | 108.0 |
Sn1—C4—H4a | 107.5 | H18Ba—C18B—H18Bb | 109.5 |
Sn1—C4—H4b | 107.5 | C17B—C18B—H18Ba | 108.1 |
Sn1—C8—H8a | 107.6 | C17B—C18B—H18Bb | 108.1 |
Sn1—C8—H8b | 107.6 | C19B—C18B—H18Ba | 108.1 |
Sn1—C12—H12a | 108.1 | C19B—C18B—H18Bb | 108.1 |
Sn1—C12—H12b | 108.1 | H19Ba—C19B—H19Bb | 108.1 |
Sn2—C16A—H16Aa | 107.9 | H19Ba—C19B—H19Bc | 108.1 |
Sn2—C16A—H16Ab | 107.9 | H19Bb—C19B—H19Bc | 109.5 |
Sn2—C16B—H16Ba | 107.9 | C18B—C19B—H19Ba | 115.0 |
Sn2—C16B—H16Bb | 107.9 | C18B—C19B—H19Bb | 108.1 |
Sn2—C20A—H20Aa | 106.5 | C18B—C19B—H19Bc | 108.1 |
Sn2—C20A—H20Ab | 106.5 | H20Aa—C20A—H20Ab | 109.5 |
Sn2—C20B—H20Ba | 107.8 | C21A—C20A—H20Aa | 106.5 |
Sn2—C20B—H20Bb | 107.8 | C21A—C20A—H20Ab | 106.5 |
Sn2—C24B—H24Ba | 108.7 | H21Aa—C21A—H21Ab | 109.5 |
Sn2—C24B—H24Bb | 108.7 | C22A—C21A—H21Aa | 108.2 |
Sn3—C28—H28a | 108.5 | C20A—C21A—H21Aa | 108.2 |
Sn3—C28—H28b | 108.5 | C22A—C21A—H21Ab | 108.2 |
Sn3—C32—H32a | 107.7 | C20A—C21A—H21Ab | 108.2 |
Sn3—C32—H32b | 107.7 | H22Aa—C22A—H22AB | 109.5 |
Sn3—C36—H36a | 108.6 | C21A—C22A—H22Aa | 109.1 |
Sn3—C36—H36b | 108.6 | C23A—C22A—H22Aa | 109.1 |
C2—N1—HN1 | 108.5 | C21A—C22A—H22AB | 109.1 |
C1—N1—HN1 | 108.5 | C23A—C22A—H22AB | 109.1 |
H1a—C1—H1b | 109.5 | H23Aa—C23A—H23Ab | 109.1 |
N1—C1—H1a | 109.5 | H23Aa—C23A—H23Ac | 109.1 |
N1—C1—H1b | 109.5 | H23Ab—C23A—H23Ac | 109.5 |
P1iv—C1—H1a | 109.5 | C22A—C23A—H23Ab | 109.1 |
P1iv—C1—H1b | 109.5 | C22A—C23A—H23Ac | 109.1 |
H2a—C2—H2b | 109.5 | C22A—C23A—H23Aa | 111.0 |
N1—C2—H2a | 108.6 | H20Ba—C20B—H20Bb | 109.5 |
C3—C2—H2a | 108.6 | C21B—C20B—H20Ba | 107.8 |
N1—C2—H2b | 108.6 | C21B—C20B—H20Bb | 107.8 |
C3—C2—H2b | 108.6 | H21Ba—C21B—H21Bb | 109.5 |
H4a—C4—H4b | 109.5 | C22B—C21B—H21Ba | 108.4 |
C5—C4—H4a | 107.5 | C20B—C21B—H21Ba | 108.4 |
C5—C4—H4b | 107.5 | C22B—C21B—H21Bb | 108.4 |
H5a—C5—H5b | 109.5 | C20B—C21B—H21Bb | 108.4 |
C4—C5—H5a | 108.0 | H22Ba—C22B—H22Bb | 109.5 |
C6—C5—H5a | 108.0 | C21B—C22B—H22Ba | 108.3 |
C4—C5—H5b | 108.0 | C23B—C22B—H22Ba | 108.3 |
C6—C5—H5b | 108.0 | C21B—C22B—H22Bb | 108.3 |
H6a—C6—H6b | 109.5 | C23B—C22B—H22Bb | 108.3 |
C7—C6—H6a | 108.4 | H23Ba—C23B—H23Bb | 108.3 |
C5—C6—H6a | 108.4 | H23Ba—C23B—H23Bc | 108.3 |
C7—C6—H6b | 108.4 | H23Bb—C23B—H23Bc | 109.5 |
C5—C6—H6b | 108.4 | C22B—C23B—H23Bb | 108.3 |
H7a—C7—H7b | 108.4 | C22B—C23B—H23Bc | 108.3 |
H7a—C7—H7c | 108.4 | C22B—C23B—H23Ba | 114.0 |
C6—C7—H7a | 113.8 | H24Aa—C24A—H24Ab | 109.5 |
H7b—C7—H7c | 109.5 | C25A—C24A—H24Aa | 107.9 |
C6—C7—H7b | 108.4 | C25A—C24A—H24Ab | 107.9 |
C6—C7—H7c | 108.4 | H25Aa—C25A—H25Ab | 109.5 |
H8a—C8—H8b | 109.5 | C24A—C25A—H25Ab | 108.1 |
C9—C8—H8a | 107.6 | C26A—C25A—H25Ab | 108.1 |
C9—C8—H8b | 107.6 | C24A—C25A—H25Aa | 108.1 |
H9a—C9—H9b | 109.5 | C26A—C25A—H25Aa | 108.1 |
C8—C9—H9a | 108.6 | H26Aa—C26A—H26Ab | 109.5 |
C10—C9—H9a | 108.6 | C27A—C26A—H26Aa | 108.6 |
C8—C9—H9b | 108.6 | C25A—C26A—H26Aa | 108.6 |
C10—C9—H9b | 108.6 | C27A—C26A—H26Ab | 108.6 |
H10a—C10—H10b | 109.5 | C25A—C26A—H26Ab | 108.6 |
C11—C10—H10a | 108.5 | H27Aa—C27A—H27Ab | 108.6 |
C9—C10—H10a | 108.5 | H27Aa—C27A—H27Ac | 108.6 |
C11—C10—H10b | 108.5 | H27Ab—C27A—H27Ac | 109.5 |
C9—C10—H10b | 108.5 | C26A—C27A—H27Aa | 112.8 |
H11a—C11—H11b | 108.5 | C26A—C27A—H27Ab | 108.6 |
H11a—C11—H11c | 108.5 | C26A—C27A—H27Ac | 108.6 |
C10—C11—H11a | 113.2 | H24Ba—C24B—H24Bb | 109.5 |
H11b—C11—H11c | 109.5 | C25B—C24B—H24Ba | 108.7 |
C10—C11—H11b | 108.5 | C25B—C24B—H24Bb | 108.7 |
C10—C11—H11c | 108.5 | H25Ba—C25B—H25Bb | 109.5 |
H12a—C12—H12b | 109.5 | C26B—C25B—H25Ba | 108.8 |
C13—C12—H12a | 108.1 | C24B—C25B—H25Ba | 108.8 |
C13—C12—H12b | 108.1 | C26B—C25B—H25Bb | 108.8 |
H13a—C13—H13b | 109.5 | C24B—C25B—H25Bb | 108.8 |
C12—C13—H13a | 108.6 | H26Ba—C26B—H26Bb | 109.5 |
C14—C13—H13a | 108.6 | C27B—C26B—H26Ba | 109.6 |
C12—C13—H13b | 108.6 | C25B—C26B—H26Ba | 109.6 |
C14—C13—H13b | 108.6 | C27B—C26B—H26Bb | 109.6 |
H14a—C14—H14b | 109.5 | C25B—C26B—H26Bb | 109.6 |
C15—C14—H14a | 108.4 | H27Ba—C27B—H27Bb | 109.6 |
C13—C14—H14a | 108.4 | H27Ba—C27B—H27Bc | 109.6 |
C15—C14—H14b | 108.4 | H27Bb—C27B—H27Bc | 109.5 |
C13—C14—H14b | 108.4 | C26B—C27B—H27Ba | 109.0 |
H15a—C15—H15b | 108.4 | C26B—C27B—H27Bb | 109.6 |
H15a—C15—H15c | 108.4 | C26B—C27B—H27Bc | 109.6 |
O1iv—P1iv—C1—N1 | 179.8 (3) | N1—C2—C3—O4 | −168.4 (3) |
P1iv—C1—N1—C2 | 178.2 (2) | N1—C2—C3—O5 | 12.6 (4) |
C1—N1—C2—C3 | −154.1 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x+1, y, z; (iii) −x, y+1/2, −z+1; (iv) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Sn3(C4H9)9(C3H5O5P)] |
Mr | 1036.20 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 120 |
a, b, c (Å) | 10.2144 (7), 18.018 (1), 13.1304 (9) |
β (°) | 90.177 (1) |
V (Å3) | 2416.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.61 |
Crystal size (mm) | 0.47 × 0.16 × 0.15 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Integration (XPREP; Siemens, 1995) |
Tmin, Tmax | 0.501, 0.799 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28299, 13624, 12628 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.699 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.071, 1.12 |
No. of reflections | 12628 |
No. of parameters | 431 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.2 (1), −1.1 (1) |
Absolute structure | Rogers (1981) |
Rogers parameter | 0.73 (3) |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SIR97 (Cascarano et al., 1996) and KRYSTAL (Hazell, 1995), modified ORFLS (Busing et al., 1962) and KRYSTAL, ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL, KRYSTAL.
Sn1—C4 | 2.144 (4) | Sn2—C20B | 2.095 (7) |
Sn1—C8 | 2.135 (4) | Sn2—C24B | 2.149 (8) |
Sn1—C12 | 2.142 (3) | Sn2—O3 | 2.160 (3) |
Sn1—O1 | 2.205 (2) | Sn2—O4 | 2.408 (3) |
Sn1—O5 | 2.292 (2) | Sn3—C28 | 2.136 (5) |
Sn2—C16A | 2.093 (6) | Sn3—C32 | 2.147 (5) |
Sn2—C20A | 2.217 (8) | Sn3—C36 | 2.134 (4) |
Sn2—C24A | 2.124 (8) | Sn3—O2 | 2.030 (3) |
Sn2—C16B | 2.174 (7) |
Organotin(IV) compounds have been used as marine anti-fouling agents, agricultural fungicides, miticides and surface disinfectants (Davies & Smith, 1982). An interesting development is the synthesis of organotin compounds in which the organotin moiety is bonded to ligands which exhibit biocidal activity. One such ligand system is the widely used commercial herbicide, glyphosate, N-(phosphonomethyl)glycine, which forms complexes in which the carboxylate oxygen atoms, the phosphonate oxygen atoms or the nitrogen atom can coordinate to a metal atom (Appleton et al., 1994; Franz et al., 1997). The incorporation of organotin and phosphorus portions in one molecule leads to the possibility that each fragment may make a contribution to the compound's overall biocidal activity. We here report the synthesis and the crystal structure of the glyphosphate complex with bistributyltin oxide, (I). \sch
Regardless of the proportions of glyphosate and bis(tri-n-butyltin)oxide used, we obtained a product of which was shown by elemental microanalysis to be the 3:1 (tin:ligand) adduct (n-Bu3Sn)3(OCOCH2NHCH2PO3). The structure determination showed all five oxygen atoms of the glyphosate to be bonded to tin atoms (Fig. 1) to give a polymeric structure. The glyphosate moiety, together with Sn1 and Sn2, forms a two-dimensional network with the Sn3 atoms situated alternately above and below the plane of the network (Fig. 2). Sn1 and Sn2 are penta-coordinated to two oxygen atoms and to three n-butyl groups at the corners of a trigonal bipyramid with the oxygen atoms in the axial positions whereas Sn3 is tetrahedrally coordinated to one oxygen atom and to three n-butyl groups. The n-butyl groups around Sn2 are disordered. There is a wide spread in the Sn—O bond distances, 2.030 (3) to 2.408 (3) Å, the P—O distances are in the range 1.508 (3)–1.543 (3) Å and the C—O distances are 1.239 (4) and 1.263 (4) Å. The Sn—O distances for oxygen atoms trans to carboxylate groups are shorter than those trans to phosphonate groups and dSn—O decreases with increasing dC/P—O (ΔSn—O simeq -4.6ΔC/P—O). Only one hydrogen atom was observed on the nitrogen atom, in agreement with the observation of an NH stretching frequency of 3300 cm-1 together with the absence of ν(+NH)bands. The intramolecular contacts N1···O5(-1 - x, 1/2 + y,1 - z) [2.643 (4) Å] and N1···O3(-1 - x, 1/2 + y, 1 - z) [3.018 (4) Å] can be attributed to hydrogen bonding. The backbone of the glyphosate group is a nonplanar zigzag chain; O1—P1—C1—N1—C2 and N1—C2—C3—O4 form nearly planar groups with the C1—N1—C2—C3 torsion angle -154.1 (3)°. Comparison of the IR-spectra with that observed by Rajendram & Hoggard (1994) for glyphosate shows that the symmetric and asymmetric C—O stretching vibrations are lowered on bonding, from 1734 to 1578 cm-1 and from 1485 to 1404 cm-1. Similarly the symmetric and asymmetric P—O stretching frequencies and the O—P—O bending-stretching frequencies are lowered from 1160, 917 and 1095 cm-1 to 1138, 877 and 1065 cm-1. The sharp ν(N—H) stretching band observed at 3300 cm-1 (3230 cm-1 for glyphosate) and the absence of ν(+NH) indicate that the N amino atom in the ligand is neither protonated nor involved in coordination to the tin atoms. Δν = νasym(OCO) - νsym(OCO) is expected to be about 200 cm-1 for a bridging of chelating carboxyl group (Deacon & Phillips, 1980; Micera et al., 1984), the value found here is 174 cm-1.