The structure of 6I,6II-dideoxy-6I-(p-methylbenzylthio)-6II- phenylthio-β-cyclodextrin tetradecahydrate, C56H82O33S2·14H2O, has been determined. Of the two substituents, only the phenylthio moiety is included in the cavity of adjacent disubstituted β-cyclodextrin (β-CD) units, forming a helical polymer.
Supporting information
CCDC reference: 209915
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.014 Å
- Disorder in solvent or counterion
- R factor = 0.096
- wR factor = 0.255
- Data-to-parameter ratio = 10.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25
Weighted R factor given 0.255
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.118
PLAT_213 Alert C Atom O6F has ADP max/min Ratio ........... 3.30 prolate
PLAT_302 Alert C Anion/Solvent Disorder ....................... 7.00 Perc.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 28.28
From the CIF: _reflns_number_total 9891
Count of symmetry unique reflns 9945
Completeness (_total/calc) 99.46%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
The title compound was synthesized as described elsewhere (Fujita et al., 2003). Colourless crystals were obtained from a water–acetonitrile (4:1) solution. The structure has been determined at low temperature (173 K).
H atoms were treated as riding atoms. The positions of the H atoms of the crystal water molecules were calculated with the program HYDROGEN (Nardelli, 1999) and included into the refinement with constrained atomic coordinates. A disorder of the phenyl ring was resolved by two sets of atomic coordinates and isotropic refinement.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) and HYDROGEN (Nardelli, 1999); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and IUCr SHELXL97 template.
6
I,6
II-dideoxy-6
I-(
p-methylbenzylthio)-6
II-phenylthio-
β-cyclodextrin tetradecahydrate
top
Crystal data top
C56H82O33S2·14H2O | Dx = 1.442 Mg m−3 |
Mr = 1599.56 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 34217 reflections |
a = 14.4635 (7) Å | θ = 1.6–24.7° |
b = 17.337 (1) Å | µ = 0.18 mm−1 |
c = 29.388 (2) Å | T = 173 K |
V = 7369.1 (7) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
F(000) = 3416 | |
Data collection top
Stoe IPDS 2 diffractometer | 4958 reflections with I > 2σ(I) |
Radiation source: sealed tube X-ray tube 12 x 0.4mm long-fine-focus | Rint = 0.118 |
Plane graphite monochromator | θmax = 28.3°, θmin = 1.6° |
Detector resolution: 6.67 pixels mm-1 | h = −18→19 |
rotation method scans | k = −23→20 |
34217 measured reflections | l = −39→38 |
9891 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.096 | H-atom parameters constrained |
wR(F2) = 0.255 | w = 1/[σ2(Fo2) + (0.1146P)2 + 1.2217P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.003 |
9891 reflections | Δρmax = 0.71 e Å−3 |
941 parameters | Δρmin = −0.46 e Å−3 |
700 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0116 (9) |
Crystal data top
C56H82O33S2·14H2O | V = 7369.1 (7) Å3 |
Mr = 1599.56 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.4635 (7) Å | µ = 0.18 mm−1 |
b = 17.337 (1) Å | T = 173 K |
c = 29.388 (2) Å | 0.30 × 0.20 × 0.20 mm |
Data collection top
Stoe IPDS 2 diffractometer | 4958 reflections with I > 2σ(I) |
34217 measured reflections | Rint = 0.118 |
9891 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.096 | 700 restraints |
wR(F2) = 0.255 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.71 e Å−3 |
9891 reflections | Δρmin = −0.46 e Å−3 |
941 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O4G | −0.0983 (4) | −0.3773 (3) | 0.13131 (19) | 0.0361 (13) | |
C1A | −0.1657 (6) | −0.4349 (5) | 0.1211 (3) | 0.043 (2) | |
H1A | −0.1861 | −0.4600 | 0.1500 | 0.052* | |
O5A | −0.2436 (4) | −0.4007 (3) | 0.0996 (2) | 0.0427 (14) | |
C2A | −0.1217 (6) | −0.4947 (5) | 0.0908 (3) | 0.041 (2) | |
H2A | −0.1683 | −0.5363 | 0.0852 | 0.049* | |
O2A | −0.0447 (4) | −0.5285 (3) | 0.1139 (2) | 0.0472 (15) | |
H2OA | −0.0209 | −0.4958 | 0.1314 | 0.057* | |
C3A | −0.0965 (6) | −0.4597 (5) | 0.0452 (3) | 0.041 (2) | |
H3A | −0.0470 | −0.4201 | 0.0496 | 0.049* | |
O3A | −0.0625 (5) | −0.5202 (4) | 0.0168 (2) | 0.0520 (17) | |
H3OA | −0.0459 | −0.5018 | −0.0083 | 0.062* | |
C4A | −0.1806 (6) | −0.4220 (5) | 0.0245 (3) | 0.0380 (19) | |
H4A | −0.2281 | −0.4624 | 0.0178 | 0.046* | |
C5A | −0.2206 (6) | −0.3637 (5) | 0.0574 (3) | 0.044 (2) | |
H5A | −0.1736 | −0.3226 | 0.0632 | 0.052* | |
C6A | −0.3099 (6) | −0.3263 (6) | 0.0416 (3) | 0.047 (2) | |
H6A1 | −0.3588 | −0.3662 | 0.0410 | 0.057* | |
H6A2 | −0.3011 | −0.3079 | 0.0100 | 0.057* | |
C7A | −0.2561 (8) | −0.1815 (6) | 0.0661 (6) | 0.091 (5) | |
H7A1 | −0.2084 | −0.1901 | 0.0897 | 0.109* | |
H7A2 | −0.2279 | −0.1929 | 0.0361 | 0.109* | |
O4F | 0.0314 (4) | −0.1889 (3) | 0.20543 (18) | 0.0353 (13) | |
C1G | 0.0060 (6) | −0.2482 (5) | 0.2366 (3) | 0.0353 (18) | |
H1G | 0.0233 | −0.2317 | 0.2680 | 0.042* | |
O5G | −0.0912 (4) | −0.2616 (3) | 0.23503 (19) | 0.0382 (13) | |
C2G | 0.0587 (6) | −0.3214 (5) | 0.2248 (3) | 0.0375 (19) | |
H2G | 0.0467 | −0.3607 | 0.2491 | 0.045* | |
O2G | 0.1551 (5) | −0.3040 (4) | 0.2244 (2) | 0.0473 (15) | |
H2OG | 0.1771 | −0.3140 | 0.1986 | 0.057* | |
C3G | 0.0268 (6) | −0.3537 (4) | 0.1797 (3) | 0.0311 (17) | |
H3G | 0.0480 | −0.3173 | 0.1555 | 0.037* | |
O3G | 0.0665 (4) | −0.4281 (3) | 0.1699 (2) | 0.0385 (14) | |
H3OG | 0.1243 | −0.4240 | 0.1681 | 0.046* | |
C4G | −0.0780 (6) | −0.3596 (5) | 0.1762 (3) | 0.040 (2) | |
H4G | −0.1005 | −0.4020 | 0.1964 | 0.048* | |
C5G | −0.1228 (6) | −0.2838 (4) | 0.1904 (3) | 0.0313 (17) | |
H5G | −0.1039 | −0.2430 | 0.1682 | 0.038* | |
C6G | −0.2273 (7) | −0.2858 (6) | 0.1926 (3) | 0.044 (2) | |
H6G1 | −0.2505 | −0.2354 | 0.2036 | 0.053* | |
H6G2 | −0.2526 | −0.2946 | 0.1617 | 0.053* | |
O6G | −0.2585 (4) | −0.3457 (3) | 0.2225 (2) | 0.0432 (14) | |
H6OG | −0.2571 | −0.3298 | 0.2494 | 0.052* | |
O4E | 0.0994 (4) | 0.0374 (3) | 0.15288 (19) | 0.0397 (14) | |
C1F | 0.1068 (7) | 0.0399 (5) | 0.2014 (3) | 0.044 (2) | |
H1F | 0.1256 | 0.0930 | 0.2109 | 0.053* | |
O5F | 0.0229 (5) | 0.0213 (3) | 0.2222 (2) | 0.0514 (18) | |
C2F | 0.1807 (7) | −0.0166 (5) | 0.2156 (3) | 0.045 (2) | |
H2F | 0.1893 | −0.0129 | 0.2493 | 0.055* | |
O2F | 0.2652 (5) | 0.0030 (4) | 0.1941 (2) | 0.0527 (17) | |
H2OF | 0.3092 | −0.0190 | 0.2075 | 0.063* | |
C3F | 0.1523 (7) | −0.0974 (5) | 0.2040 (3) | 0.042 (2) | |
H3F | 0.1496 | −0.1016 | 0.1701 | 0.050* | |
O3F | 0.2193 (5) | −0.1527 (3) | 0.2200 (2) | 0.0481 (16) | |
H3OF | 0.1974 | −0.1974 | 0.2177 | 0.058* | |
C4F | 0.0580 (7) | −0.1156 (5) | 0.2222 (3) | 0.041 (2) | |
H4F | 0.0622 | −0.1189 | 0.2561 | 0.049* | |
C5F | −0.0118 (7) | −0.0538 (5) | 0.2102 (4) | 0.052 (3) | |
H5F | −0.0221 | −0.0551 | 0.1766 | 0.062* | |
C6F | −0.1060 (8) | −0.0630 (6) | 0.2339 (5) | 0.069 (4) | |
H6F1 | −0.1480 | −0.0212 | 0.2239 | 0.083* | |
H6F2 | −0.1340 | −0.1129 | 0.2250 | 0.083* | |
O6F | −0.0960 (7) | −0.0604 (5) | 0.2816 (3) | 0.095 (4) | |
H6OF | −0.0881 | −0.0145 | 0.2899 | 0.114* | |
O4D | 0.0773 (4) | 0.1220 (3) | 0.00996 (19) | 0.0370 (13) | |
C1E | 0.0940 (7) | 0.1836 (5) | 0.0415 (3) | 0.044 (2) | |
H1E | 0.0962 | 0.2332 | 0.0242 | 0.053* | |
O5E | 0.0229 (5) | 0.1883 (3) | 0.0734 (2) | 0.0505 (16) | |
C2E | 0.1871 (7) | 0.1707 (6) | 0.0635 (4) | 0.049 (2) | |
H2E | 0.2038 | 0.2171 | 0.0821 | 0.059* | |
O2E | 0.2546 (5) | 0.1596 (4) | 0.0295 (2) | 0.0596 (19) | |
H2OE | 0.2968 | 0.1311 | 0.0395 | 0.071* | |
C3E | 0.1842 (6) | 0.1002 (6) | 0.0943 (3) | 0.045 (2) | |
H3E | 0.1727 | 0.0537 | 0.0749 | 0.054* | |
O3E | 0.2702 (5) | 0.0902 (5) | 0.1170 (2) | 0.065 (2) | |
H3OE | 0.2608 | 0.0847 | 0.1450 | 0.078* | |
C4E | 0.1050 (7) | 0.1080 (5) | 0.1277 (3) | 0.044 (2) | |
H4E | 0.1172 | 0.1519 | 0.1489 | 0.052* | |
C5E | 0.0157 (7) | 0.1217 (6) | 0.1023 (3) | 0.051 (2) | |
H5E | 0.0057 | 0.0761 | 0.0820 | 0.062* | |
C6E | −0.0758 (16) | 0.1345 (8) | 0.1296 (5) | 0.131 (9) | |
H6E1 | −0.1284 | 0.1442 | 0.1088 | 0.158* | |
H6E2 | −0.0902 | 0.0891 | 0.1487 | 0.158* | |
O6E | −0.0578 (10) | 0.1993 (11) | 0.1566 (4) | 0.174 (8) | |
H6OE | −0.0711 | 0.2395 | 0.1420 | 0.208* | |
O4C | −0.0057 (4) | 0.0125 (3) | −0.11787 (19) | 0.0375 (13) | |
C1D | 0.0024 (6) | 0.0919 (5) | −0.1253 (3) | 0.040 (2) | |
H1D | −0.0137 | 0.1041 | −0.1576 | 0.048* | |
O5D | −0.0569 (4) | 0.1336 (3) | −0.0956 (2) | 0.0432 (15) | |
C2D | 0.1037 (6) | 0.1135 (5) | −0.1161 (3) | 0.042 (2) | |
H2D | 0.1110 | 0.1695 | −0.1236 | 0.051* | |
O2D | 0.1637 (4) | 0.0720 (4) | −0.1450 (2) | 0.0472 (15) | |
H2OD | 0.1528 | 0.0246 | −0.1426 | 0.057* | |
C3D | 0.1276 (5) | 0.1035 (5) | −0.0662 (3) | 0.038 (2) | |
H3D | 0.1276 | 0.0472 | −0.0589 | 0.045* | |
O3D | 0.2182 (4) | 0.1329 (4) | −0.0598 (2) | 0.0506 (17) | |
H3OD | 0.2327 | 0.1292 | −0.0322 | 0.061* | |
C4D | 0.0582 (6) | 0.1433 (5) | −0.0363 (3) | 0.0380 (19) | |
H4D | 0.0651 | 0.2004 | −0.0397 | 0.046* | |
C5D | −0.0407 (6) | 0.1203 (5) | −0.0483 (3) | 0.040 (2) | |
H5D | −0.0508 | 0.0646 | −0.0411 | 0.048* | |
C6D | −0.1114 (7) | 0.1694 (7) | −0.0233 (4) | 0.058 (3) | |
H6D1 | −0.1745 | 0.1531 | −0.0321 | 0.069* | |
H6D2 | −0.1046 | 0.1618 | 0.0099 | 0.069* | |
O6D | −0.0988 (6) | 0.2504 (5) | −0.0342 (3) | 0.078 (3) | |
H6OD | −0.1287 | 0.2775 | −0.0156 | 0.094* | |
O4B | −0.1047 (4) | −0.2218 (3) | −0.1301 (2) | 0.0445 (15) | |
C1C | −0.1208 (6) | −0.1840 (6) | −0.1724 (3) | 0.047 (2) | |
H1C | −0.1516 | −0.2208 | −0.1938 | 0.056* | |
O5C | −0.1782 (4) | −0.1191 (4) | −0.1663 (2) | 0.0462 (15) | |
C2C | −0.0277 (7) | −0.1610 (5) | −0.1919 (3) | 0.046 (2) | |
H2C | −0.0382 | −0.1376 | −0.2226 | 0.055* | |
O2C | 0.0326 (5) | −0.2250 (4) | −0.1972 (3) | 0.0609 (19) | |
H2OC | 0.0064 | −0.2651 | −0.1876 | 0.073* | |
C3C | 0.0173 (6) | −0.1003 (5) | −0.1617 (3) | 0.041 (2) | |
H3C | 0.0356 | −0.1248 | −0.1322 | 0.050* | |
O3C | 0.0975 (4) | −0.0698 (4) | −0.1830 (2) | 0.0453 (15) | |
H3OC | 0.1429 | −0.0987 | −0.1777 | 0.054* | |
C4C | −0.0478 (6) | −0.0349 (5) | −0.1521 (3) | 0.040 (2) | |
H4C | −0.0563 | −0.0038 | −0.1805 | 0.048* | |
C5C | −0.1424 (6) | −0.0625 (5) | −0.1353 (3) | 0.044 (2) | |
H5C | −0.1352 | −0.0864 | −0.1045 | 0.053* | |
C6C | −0.2140 (7) | −0.0008 (6) | −0.1330 (4) | 0.054 (3) | |
H6C1 | −0.1889 | 0.0438 | −0.1160 | 0.065* | |
H6C2 | −0.2289 | 0.0167 | −0.1642 | 0.065* | |
O6C | −0.2952 (4) | −0.0265 (4) | −0.1116 (2) | 0.0574 (19) | |
H6OC | −0.3344 | 0.0093 | −0.1113 | 0.069* | |
O4A | −0.1532 (4) | −0.3864 (3) | −0.0167 (2) | 0.0389 (13) | |
C1B | −0.1873 (6) | −0.4151 (5) | −0.0579 (3) | 0.041 (2) | |
H1B | −0.2158 | −0.4667 | −0.0519 | 0.049* | |
O5B | −0.2571 (4) | −0.3658 (3) | −0.0767 (2) | 0.0454 (15) | |
C2B | −0.1101 (7) | −0.4260 (6) | −0.0913 (3) | 0.051 (2) | |
H2B | −0.1360 | −0.4516 | −0.1190 | 0.061* | |
O2B | −0.0419 (5) | −0.4750 (4) | −0.0727 (2) | 0.0613 (19) | |
H2OB | −0.0086 | −0.4925 | −0.0937 | 0.074* | |
C3B | −0.0702 (6) | −0.3488 (6) | −0.1054 (3) | 0.043 (2) | |
H3B | −0.0406 | −0.3243 | −0.0783 | 0.052* | |
O3B | −0.0022 (5) | −0.3589 (4) | −0.1397 (2) | 0.0593 (19) | |
H3OB | 0.0498 | −0.3462 | −0.1293 | 0.071* | |
C4B | −0.1465 (6) | −0.2967 (5) | −0.1223 (3) | 0.043 (2) | |
H4B | −0.1721 | −0.3172 | −0.1515 | 0.052* | |
C5B | −0.2222 (6) | −0.2907 (5) | −0.0875 (3) | 0.043 (2) | |
H5B | −0.1973 | −0.2661 | −0.0593 | 0.051* | |
C6B | −0.3053 (6) | −0.2437 (6) | −0.1050 (3) | 0.045 (2) | |
H6B1 | −0.3386 | −0.2758 | −0.1275 | 0.054* | |
H6B2 | −0.2808 | −0.1982 | −0.1215 | 0.054* | |
C7B | −0.4608 (6) | −0.2894 (6) | −0.0517 (3) | 0.046 (2) | |
C8B | −0.5061 (12) | −0.3079 (14) | −0.0122 (7) | 0.069 (7)* | 0.50 |
H8B | −0.4976 | −0.2731 | 0.0123 | 0.083* | 0.50 |
C9B | −0.5635 (15) | −0.3713 (14) | −0.0033 (8) | 0.064 (6)* | 0.50 |
H9B | −0.5912 | −0.3776 | 0.0258 | 0.077* | 0.50 |
C10B | −0.5789 (15) | −0.4241 (14) | −0.0371 (7) | 0.069 (7)* | 0.50 |
H10B | −0.6164 | −0.4681 | −0.0315 | 0.082* | 0.50 |
C11B | −0.5396 (14) | −0.4127 (11) | −0.0792 (8) | 0.057 (6)* | 0.50 |
H11B | −0.5511 | −0.4471 | −0.1037 | 0.069* | 0.50 |
C12B | −0.4815 (14) | −0.3481 (9) | −0.0844 (6) | 0.038 (5)* | 0.50 |
H12B | −0.4526 | −0.3428 | −0.1133 | 0.045* | 0.50 |
C13B | −0.5065 (9) | −0.2751 (9) | −0.0107 (4) | 0.024 (3)* | 0.50 |
H13B | −0.5005 | −0.2272 | 0.0047 | 0.029* | 0.50 |
C14B | −0.5616 (11) | −0.3348 (9) | 0.0066 (6) | 0.039 (4)* | 0.50 |
H14B | −0.5955 | −0.3274 | 0.0340 | 0.047* | 0.50 |
C15B | −0.5665 (13) | −0.4040 (11) | −0.0160 (7) | 0.046 (5)* | 0.50 |
H15B | −0.5995 | −0.4464 | −0.0035 | 0.055* | 0.50 |
C16B | −0.5217 (14) | −0.4103 (12) | −0.0579 (7) | 0.053 (5)* | 0.50 |
H16B | −0.5343 | −0.4547 | −0.0758 | 0.063* | 0.50 |
C17B | −0.4596 (19) | −0.3560 (11) | −0.0756 (9) | 0.079 (10)* | 0.50 |
H17B | −0.4212 | −0.3650 | −0.1012 | 0.095* | 0.50 |
C8A | −0.2851 (8) | −0.0980 (6) | 0.0671 (5) | 0.065 (3) | |
C9A | −0.3112 (8) | −0.0612 (7) | 0.0292 (4) | 0.063 (3) | |
H9A | −0.3164 | −0.0898 | 0.0018 | 0.076* | |
C10A | −0.3310 (9) | 0.0175 (7) | 0.0284 (5) | 0.073 (3) | |
H10A | −0.3471 | 0.0416 | 0.0005 | 0.088* | |
C11A | −0.3276 (8) | 0.0599 (6) | 0.0670 (5) | 0.065 (3) | |
C12A | −0.3041 (9) | 0.0198 (7) | 0.1079 (5) | 0.078 (4) | |
H12A | −0.3025 | 0.0469 | 0.1360 | 0.093* | |
C13A | −0.2839 (9) | −0.0577 (6) | 0.1069 (4) | 0.062 (3) | |
H13A | −0.2689 | −0.0836 | 0.1344 | 0.074* | |
C14A | −0.3483 (12) | 0.1454 (7) | 0.0690 (8) | 0.124 (7) | |
H141 | −0.3443 | 0.1632 | 0.1005 | 0.149* | |
H142 | −0.4107 | 0.1549 | 0.0573 | 0.149* | |
H143 | −0.3033 | 0.1734 | 0.0503 | 0.149* | |
S6B | −0.38706 (17) | −0.21042 (15) | −0.06456 (8) | 0.0476 (6) | |
S6A | −0.34991 (16) | −0.24698 (14) | 0.07551 (8) | 0.0457 (6) | |
O1W | 0.409 (2) | −0.1579 (13) | 0.2695 (5) | 0.311 (17) | |
H1W | 0.3586 | −0.1530 | 0.2550 | 0.373* | |
H2W | 0.4036 | −0.1322 | 0.2937 | 0.373* | |
O2W | −0.5219 (6) | −0.8337 (4) | −0.0323 (3) | 0.072 (2) | |
H3W | −0.5373 | −0.8749 | −0.0192 | 0.086* | |
H4W | −0.4734 | −0.8423 | −0.0471 | 0.086* | |
O3W | −0.3807 (7) | −0.8129 (5) | −0.1626 (3) | 0.079 (2) | |
H5W | −0.4060 | −0.8460 | −0.1794 | 0.095* | |
H6W | −0.4215 | −0.7813 | −0.1545 | 0.095* | |
O4W | −0.2251 (7) | −0.7413 (6) | −0.1987 (3) | 0.093 (3) | |
H7W | −0.2635 | −0.7710 | −0.1864 | 0.112* | |
H8W | −0.1805 | −0.7355 | −0.1807 | 0.112* | |
O5W | −0.0961 (11) | −0.7043 (7) | −0.1344 (4) | 0.139 (5) | |
H9W | −0.0956 | −0.7410 | −0.1156 | 0.167* | |
H10W | −0.1162 | −0.6650 | −0.1209 | 0.167* | |
O6W | −0.6291 (9) | −0.8205 (8) | −0.1139 (5) | 0.148 (6) | |
H11W | −0.6857 | −0.8089 | −0.1122 | 0.177* | |
H12W | −0.6255 | −0.8654 | −0.1243 | 0.177* | |
O7W | 0.7427 (10) | 0.1173 (10) | 0.2151 (6) | 0.188 (8) | |
H13W | 0.7656 | 0.1378 | 0.2384 | 0.226* | |
H14W | 0.7497 | 0.0694 | 0.2172 | 0.226* | |
O8W | 0.4216 (14) | −0.0188 (14) | 0.2339 (7) | 0.262 (13) | |
H15W | 0.4385 | 0.0028 | 0.2583 | 0.314* | |
H16W | 0.4546 | −0.0583 | 0.2305 | 0.314* | |
O9W | 0.3823 (17) | 0.3575 (19) | 0.2314 (6) | 0.329 (19) | |
H17W | 0.4406 | 0.3525 | 0.2305 | 0.395* | |
H18W | 0.3682 | 0.3663 | 0.2588 | 0.395* | |
O10W | −0.3511 (5) | 0.1195 (5) | −0.0790 (3) | 0.073 (2) | |
H19W | −0.3014 | 0.0942 | −0.0793 | 0.088* | |
H20W | −0.3507 | 0.1489 | −0.1018 | 0.088* | |
O11W | 0.630 (2) | −0.0129 (14) | 0.2222 (7) | 0.271 (13) | |
H21W | 0.6457 | 0.0339 | 0.2274 | 0.326* | |
H22W | 0.6452 | −0.0381 | 0.2457 | 0.326* | |
O12W | 0.588 (3) | 0.2103 (13) | 0.1898 (8) | 0.36 (2) | |
H23W | 0.6135 | 0.1673 | 0.1941 | 0.429* | |
H24W | 0.6254 | 0.2447 | 0.1987 | 0.429* | |
O13W | 0.4908 (15) | 0.0715 (19) | 0.1505 (8) | 0.35 (2) | |
H25W | 0.5408 | 0.0756 | 0.1648 | 0.422* | |
H26W | 0.4636 | 0.1139 | 0.1512 | 0.422* | |
O14W | 0.814 (3) | 0.370 (2) | 0.1809 (13) | 0.269 (16)* | 0.70 |
H27W | 0.8277 | 0.3771 | 0.2090 | 0.323* | |
H28W | 0.7695 | 0.4015 | 0.1758 | 0.323* | |
O15W | 0.728 (4) | 0.302 (4) | 0.205 (2) | 0.21 (3)* | 0.30 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4G | 0.046 (3) | 0.025 (3) | 0.038 (3) | −0.007 (3) | 0.006 (3) | −0.006 (2) |
C1A | 0.043 (5) | 0.037 (5) | 0.050 (5) | −0.007 (4) | 0.008 (4) | −0.007 (4) |
O5A | 0.033 (3) | 0.045 (4) | 0.050 (3) | −0.003 (3) | 0.003 (3) | −0.002 (3) |
C2A | 0.038 (5) | 0.035 (5) | 0.049 (5) | 0.000 (4) | 0.005 (4) | −0.002 (4) |
O2A | 0.051 (4) | 0.035 (3) | 0.056 (4) | 0.004 (3) | 0.000 (3) | −0.006 (3) |
C3A | 0.036 (5) | 0.037 (5) | 0.048 (5) | 0.002 (4) | 0.002 (4) | −0.003 (4) |
O3A | 0.059 (4) | 0.037 (3) | 0.060 (4) | −0.001 (3) | 0.020 (3) | −0.015 (3) |
C4A | 0.041 (5) | 0.029 (4) | 0.044 (5) | 0.001 (4) | 0.005 (4) | −0.011 (4) |
C5A | 0.041 (5) | 0.038 (5) | 0.051 (5) | 0.003 (4) | 0.000 (4) | −0.008 (4) |
C6A | 0.037 (5) | 0.059 (6) | 0.045 (5) | 0.010 (4) | −0.001 (4) | −0.020 (5) |
C7A | 0.052 (7) | 0.039 (6) | 0.182 (15) | 0.005 (5) | 0.000 (9) | 0.004 (8) |
O4F | 0.046 (3) | 0.023 (3) | 0.036 (3) | −0.006 (2) | 0.013 (3) | −0.001 (2) |
C1G | 0.039 (5) | 0.033 (4) | 0.033 (4) | −0.006 (4) | 0.010 (4) | 0.002 (4) |
O5G | 0.041 (3) | 0.037 (3) | 0.037 (3) | −0.004 (3) | 0.007 (3) | 0.000 (2) |
C2G | 0.043 (5) | 0.032 (4) | 0.037 (5) | −0.001 (4) | 0.006 (4) | 0.000 (4) |
O2G | 0.050 (4) | 0.048 (4) | 0.044 (3) | 0.001 (3) | −0.002 (3) | −0.005 (3) |
C3G | 0.044 (5) | 0.021 (4) | 0.028 (4) | 0.004 (3) | 0.006 (3) | −0.006 (3) |
O3G | 0.037 (3) | 0.026 (3) | 0.053 (4) | 0.005 (2) | 0.007 (3) | −0.004 (3) |
C4G | 0.046 (5) | 0.034 (5) | 0.040 (5) | 0.007 (4) | 0.004 (4) | 0.001 (4) |
C5G | 0.045 (5) | 0.022 (4) | 0.026 (4) | −0.001 (3) | 0.004 (3) | −0.001 (3) |
C6G | 0.051 (6) | 0.043 (5) | 0.039 (5) | −0.006 (4) | 0.005 (4) | −0.001 (4) |
O6G | 0.044 (4) | 0.035 (3) | 0.050 (3) | −0.003 (3) | 0.009 (3) | −0.004 (3) |
O4E | 0.055 (4) | 0.023 (3) | 0.041 (3) | 0.001 (3) | 0.013 (3) | 0.000 (2) |
C1F | 0.065 (6) | 0.029 (4) | 0.039 (5) | −0.005 (4) | 0.019 (4) | −0.009 (4) |
O5F | 0.073 (5) | 0.022 (3) | 0.059 (4) | −0.007 (3) | 0.041 (4) | −0.007 (3) |
C2F | 0.061 (6) | 0.039 (5) | 0.037 (5) | −0.021 (5) | 0.013 (4) | −0.002 (4) |
O2F | 0.064 (5) | 0.040 (4) | 0.054 (4) | −0.012 (3) | 0.003 (3) | 0.005 (3) |
C3F | 0.062 (6) | 0.034 (5) | 0.030 (4) | −0.008 (4) | −0.004 (4) | 0.005 (3) |
O3F | 0.053 (4) | 0.031 (3) | 0.060 (4) | −0.008 (3) | −0.016 (3) | 0.011 (3) |
C4F | 0.061 (6) | 0.025 (4) | 0.037 (4) | −0.004 (4) | 0.005 (4) | −0.005 (3) |
C5F | 0.068 (7) | 0.029 (5) | 0.058 (6) | −0.001 (5) | 0.026 (5) | −0.012 (4) |
C6F | 0.066 (7) | 0.033 (5) | 0.108 (10) | −0.005 (5) | 0.044 (7) | −0.004 (6) |
O6F | 0.151 (9) | 0.063 (5) | 0.071 (5) | −0.044 (6) | 0.081 (6) | −0.024 (4) |
O4D | 0.040 (3) | 0.029 (3) | 0.042 (3) | 0.002 (2) | −0.001 (2) | 0.000 (2) |
C1E | 0.067 (6) | 0.019 (4) | 0.046 (5) | −0.013 (4) | −0.003 (5) | −0.007 (3) |
O5E | 0.071 (4) | 0.034 (3) | 0.047 (4) | 0.018 (3) | 0.006 (3) | −0.002 (3) |
C2E | 0.046 (5) | 0.043 (5) | 0.059 (6) | −0.015 (4) | −0.011 (5) | 0.009 (5) |
O2E | 0.051 (4) | 0.077 (5) | 0.051 (4) | −0.024 (4) | −0.012 (3) | 0.021 (4) |
C3E | 0.034 (5) | 0.054 (6) | 0.048 (5) | −0.005 (4) | 0.000 (4) | 0.011 (4) |
O3E | 0.055 (4) | 0.086 (6) | 0.053 (4) | −0.005 (4) | 0.000 (3) | 0.027 (4) |
C4E | 0.069 (6) | 0.024 (4) | 0.037 (4) | 0.007 (4) | 0.015 (4) | 0.007 (3) |
C5E | 0.053 (6) | 0.045 (5) | 0.056 (6) | 0.004 (5) | 0.026 (5) | 0.001 (5) |
C6E | 0.27 (3) | 0.061 (8) | 0.064 (8) | 0.046 (12) | 0.079 (12) | 0.013 (7) |
O6E | 0.158 (12) | 0.31 (2) | 0.058 (6) | 0.125 (14) | 0.003 (7) | 0.018 (9) |
O4C | 0.043 (3) | 0.029 (3) | 0.040 (3) | −0.003 (2) | −0.004 (3) | −0.002 (2) |
C1D | 0.040 (5) | 0.035 (5) | 0.044 (5) | 0.001 (4) | −0.007 (4) | −0.003 (4) |
O5D | 0.033 (3) | 0.040 (3) | 0.057 (4) | 0.005 (3) | −0.006 (3) | −0.006 (3) |
C2D | 0.041 (5) | 0.040 (5) | 0.045 (5) | 0.002 (4) | 0.002 (4) | 0.000 (4) |
O2D | 0.047 (4) | 0.043 (4) | 0.052 (4) | −0.001 (3) | 0.010 (3) | −0.009 (3) |
C3D | 0.022 (4) | 0.033 (4) | 0.059 (5) | 0.003 (3) | −0.006 (4) | −0.014 (4) |
O3D | 0.027 (3) | 0.056 (4) | 0.068 (4) | −0.005 (3) | 0.000 (3) | −0.018 (3) |
C4D | 0.039 (5) | 0.033 (4) | 0.042 (5) | 0.009 (4) | 0.000 (4) | 0.003 (4) |
C5D | 0.036 (5) | 0.029 (4) | 0.054 (5) | −0.002 (4) | −0.002 (4) | −0.005 (4) |
C6D | 0.034 (5) | 0.068 (7) | 0.072 (7) | 0.013 (5) | −0.007 (5) | −0.013 (6) |
O6D | 0.068 (5) | 0.069 (5) | 0.097 (6) | 0.043 (5) | −0.024 (5) | −0.028 (5) |
O4B | 0.043 (3) | 0.040 (3) | 0.050 (4) | −0.015 (3) | −0.006 (3) | −0.009 (3) |
C1C | 0.042 (5) | 0.056 (6) | 0.042 (5) | −0.007 (4) | −0.006 (4) | −0.007 (4) |
O5C | 0.043 (3) | 0.048 (4) | 0.048 (3) | −0.010 (3) | −0.004 (3) | −0.001 (3) |
C2C | 0.046 (5) | 0.044 (5) | 0.048 (5) | 0.002 (4) | −0.001 (4) | −0.002 (4) |
O2C | 0.055 (4) | 0.054 (4) | 0.073 (5) | −0.012 (4) | 0.007 (4) | −0.020 (4) |
C3C | 0.038 (5) | 0.042 (5) | 0.044 (5) | −0.006 (4) | 0.013 (4) | 0.001 (4) |
O3C | 0.033 (3) | 0.051 (4) | 0.051 (4) | −0.001 (3) | 0.006 (3) | −0.002 (3) |
C4C | 0.036 (5) | 0.047 (5) | 0.036 (4) | −0.007 (4) | 0.000 (4) | −0.009 (4) |
C5C | 0.042 (5) | 0.050 (5) | 0.039 (5) | −0.014 (4) | 0.003 (4) | −0.012 (4) |
C6C | 0.032 (5) | 0.061 (6) | 0.069 (7) | 0.000 (4) | −0.001 (5) | −0.005 (5) |
O6C | 0.036 (4) | 0.076 (5) | 0.060 (4) | −0.009 (3) | 0.005 (3) | 0.005 (4) |
O4A | 0.039 (3) | 0.032 (3) | 0.046 (3) | −0.001 (3) | −0.003 (3) | −0.008 (3) |
C1B | 0.041 (5) | 0.038 (5) | 0.045 (5) | −0.005 (4) | −0.014 (4) | −0.006 (4) |
O5B | 0.039 (3) | 0.041 (3) | 0.057 (4) | −0.009 (3) | −0.006 (3) | −0.003 (3) |
C2B | 0.059 (6) | 0.046 (5) | 0.047 (5) | 0.009 (5) | −0.012 (5) | −0.019 (4) |
O2B | 0.072 (5) | 0.057 (4) | 0.055 (4) | 0.031 (4) | 0.000 (4) | −0.010 (4) |
C3B | 0.033 (5) | 0.053 (5) | 0.042 (5) | −0.003 (4) | 0.000 (4) | −0.011 (4) |
O3B | 0.044 (4) | 0.074 (5) | 0.059 (4) | −0.006 (3) | −0.001 (3) | −0.025 (4) |
C4B | 0.031 (4) | 0.037 (5) | 0.061 (6) | −0.007 (4) | −0.005 (4) | −0.017 (4) |
C5B | 0.033 (5) | 0.041 (5) | 0.054 (5) | −0.011 (4) | −0.002 (4) | −0.002 (4) |
C6B | 0.040 (5) | 0.048 (5) | 0.047 (5) | 0.000 (4) | −0.009 (4) | −0.007 (4) |
C7B | 0.035 (5) | 0.064 (6) | 0.038 (5) | 0.003 (4) | −0.007 (4) | 0.000 (4) |
C8A | 0.061 (7) | 0.045 (6) | 0.090 (9) | 0.010 (5) | −0.005 (6) | −0.005 (6) |
C9A | 0.068 (7) | 0.065 (7) | 0.057 (6) | 0.007 (6) | −0.016 (6) | −0.024 (6) |
C10A | 0.062 (8) | 0.072 (8) | 0.085 (9) | 0.014 (6) | 0.005 (7) | 0.021 (7) |
C11A | 0.057 (7) | 0.042 (6) | 0.096 (9) | 0.013 (5) | 0.015 (7) | 0.015 (6) |
C12A | 0.086 (9) | 0.062 (8) | 0.085 (9) | 0.002 (7) | 0.017 (7) | −0.034 (7) |
C13A | 0.090 (8) | 0.045 (6) | 0.051 (6) | 0.011 (6) | 0.003 (6) | 0.003 (5) |
C14A | 0.103 (12) | 0.055 (8) | 0.22 (2) | 0.021 (8) | 0.050 (14) | 0.012 (11) |
S6B | 0.0433 (13) | 0.0538 (14) | 0.0457 (13) | 0.0064 (11) | −0.0075 (11) | −0.0111 (11) |
S6A | 0.0415 (12) | 0.0462 (13) | 0.0493 (13) | 0.0112 (11) | 0.0004 (10) | −0.0091 (11) |
O1W | 0.55 (4) | 0.29 (2) | 0.096 (10) | −0.24 (3) | −0.101 (18) | −0.008 (13) |
O2W | 0.101 (6) | 0.041 (4) | 0.073 (5) | −0.019 (4) | 0.022 (5) | −0.003 (4) |
O3W | 0.092 (6) | 0.069 (5) | 0.075 (5) | −0.008 (5) | −0.009 (5) | 0.016 (4) |
O4W | 0.090 (6) | 0.116 (8) | 0.074 (5) | −0.014 (6) | −0.011 (5) | 0.035 (6) |
O5W | 0.221 (15) | 0.095 (8) | 0.101 (8) | 0.012 (9) | −0.076 (9) | 0.009 (6) |
O6W | 0.134 (10) | 0.135 (10) | 0.174 (12) | −0.063 (9) | −0.022 (9) | 0.084 (9) |
O7W | 0.141 (12) | 0.217 (15) | 0.206 (15) | 0.034 (11) | −0.079 (11) | −0.153 (13) |
O8W | 0.221 (19) | 0.34 (3) | 0.228 (19) | 0.11 (2) | −0.181 (17) | −0.112 (19) |
O9W | 0.28 (3) | 0.56 (5) | 0.152 (14) | −0.31 (3) | 0.029 (16) | −0.06 (2) |
O10W | 0.060 (5) | 0.094 (6) | 0.066 (5) | 0.018 (4) | 0.007 (4) | −0.001 (4) |
O11W | 0.38 (4) | 0.25 (2) | 0.175 (16) | 0.09 (3) | 0.08 (2) | 0.032 (17) |
O12W | 0.67 (6) | 0.185 (19) | 0.22 (2) | −0.02 (3) | −0.22 (3) | 0.043 (16) |
O13W | 0.167 (18) | 0.63 (6) | 0.26 (2) | −0.08 (3) | 0.027 (17) | −0.28 (3) |
Geometric parameters (Å, º) top
O4G—C4G | 1.387 (10) | C6D—H6D1 | 0.9900 |
O4G—C1A | 1.428 (10) | C6D—H6D2 | 0.9900 |
C1A—O5A | 1.420 (11) | O6D—H6OD | 0.8400 |
C1A—C2A | 1.509 (12) | O4B—C1C | 1.427 (11) |
C1A—H1A | 1.0000 | O4B—C4B | 1.450 (10) |
O5A—C5A | 1.437 (11) | C1C—O5C | 1.409 (12) |
C2A—O2A | 1.431 (11) | C1C—C2C | 1.517 (13) |
C2A—C3A | 1.514 (12) | C1C—H1C | 1.0000 |
C2A—H2A | 1.0000 | O5C—C5C | 1.437 (10) |
O2A—H2OA | 0.8400 | C2C—O2C | 1.420 (12) |
C3A—O3A | 1.428 (10) | C2C—C3C | 1.522 (13) |
C3A—C4A | 1.509 (13) | C2C—H2C | 1.0000 |
C3A—H3A | 1.0000 | O2C—H2OC | 0.8400 |
O3A—H3OA | 0.8400 | C3C—O3C | 1.420 (10) |
C4A—O4A | 1.415 (11) | C3C—C4C | 1.501 (13) |
C4A—C5A | 1.514 (12) | C3C—H3C | 1.0000 |
C4A—H4A | 1.0000 | O3C—H3OC | 0.8400 |
C5A—C6A | 1.517 (13) | C4C—C5C | 1.530 (12) |
C5A—H5A | 1.0000 | C4C—H4C | 1.0000 |
C6A—S6A | 1.793 (9) | C5C—C6C | 1.490 (14) |
C6A—H6A1 | 0.9900 | C5C—H5C | 1.0000 |
C6A—H6A2 | 0.9900 | C6C—O6C | 1.405 (12) |
C7A—C8A | 1.508 (16) | C6C—H6C1 | 0.9900 |
C7A—S6A | 1.790 (12) | C6C—H6C2 | 0.9900 |
C7A—H7A1 | 0.9900 | O6C—H6OC | 0.8400 |
C7A—H7A2 | 0.9900 | O4A—C1B | 1.399 (10) |
O4F—C4F | 1.417 (10) | C1B—O5B | 1.434 (10) |
O4F—C1G | 1.424 (9) | C1B—C2B | 1.498 (14) |
C1G—O5G | 1.426 (10) | C1B—H1B | 1.0000 |
C1G—C2G | 1.520 (12) | O5B—C5B | 1.432 (11) |
C1G—H1G | 1.0000 | C2B—O2B | 1.412 (12) |
O5G—C5G | 1.442 (9) | C2B—C3B | 1.515 (14) |
C2G—O2G | 1.428 (11) | C2B—H2B | 1.0000 |
C2G—C3G | 1.510 (11) | O2B—H2OB | 0.8400 |
C2G—H2G | 1.0000 | C3B—O3B | 1.418 (11) |
O2G—H2OG | 0.8400 | C3B—C4B | 1.510 (13) |
C3G—O3G | 1.442 (9) | C3B—H3B | 1.0000 |
C3G—C4G | 1.523 (12) | O3B—H3OB | 0.8400 |
C3G—H3G | 1.0000 | C4B—C5B | 1.503 (13) |
O3G—H3OG | 0.8400 | C4B—H4B | 1.0000 |
C4G—C5G | 1.523 (11) | C5B—C6B | 1.540 (13) |
C4G—H4G | 1.0000 | C5B—H5B | 1.0000 |
C5G—C6G | 1.513 (13) | C6B—S6B | 1.774 (10) |
C5G—H5G | 1.0000 | C6B—H6B1 | 0.9900 |
C6G—O6G | 1.432 (10) | C6B—H6B2 | 0.9900 |
C6G—H6G1 | 0.9900 | C7B—C17B | 1.351 (17) |
C6G—H6G2 | 0.9900 | C7B—C8B | 1.371 (16) |
O6G—H6OG | 0.8400 | C7B—C13B | 1.397 (13) |
O4E—C1F | 1.429 (10) | C7B—C12B | 1.432 (15) |
O4E—C4E | 1.432 (9) | C7B—S6B | 1.776 (10) |
C1F—O5F | 1.396 (11) | C8B—C9B | 1.402 (18) |
C1F—C2F | 1.509 (14) | C8B—H8B | 0.9500 |
C1F—H1F | 1.0000 | C9B—C10B | 1.369 (18) |
O5F—C5F | 1.440 (11) | C9B—H9B | 0.9500 |
C2F—O2F | 1.418 (11) | C10B—C11B | 1.375 (18) |
C2F—C3F | 1.499 (12) | C10B—H10B | 0.9500 |
C2F—H2F | 1.0000 | C11B—C12B | 1.408 (16) |
O2F—H2OF | 0.8400 | C11B—H11B | 0.9500 |
C3F—O3F | 1.442 (11) | C12B—H12B | 0.9500 |
C3F—C4F | 1.499 (13) | C13B—C14B | 1.402 (16) |
C3F—H3F | 1.0000 | C13B—H13B | 0.9500 |
O3F—H3OF | 0.8400 | C14B—C15B | 1.374 (17) |
C4F—C5F | 1.514 (13) | C14B—H14B | 0.9500 |
C4F—H4F | 1.0000 | C15B—C16B | 1.397 (17) |
C5F—C6F | 1.538 (14) | C15B—H15B | 0.9500 |
C5F—H5F | 1.0000 | C16B—C17B | 1.400 (18) |
C6F—O6F | 1.411 (16) | C16B—H16B | 0.9500 |
C6F—H6F1 | 0.9900 | C17B—H17B | 0.9500 |
C6F—H6F2 | 0.9900 | C8A—C9A | 1.336 (16) |
O6F—H6OF | 0.8400 | C8A—C13A | 1.364 (16) |
O4D—C1E | 1.435 (9) | C9A—C10A | 1.395 (17) |
O4D—C4D | 1.435 (10) | C9A—H9A | 0.9500 |
C1E—O5E | 1.393 (11) | C10A—C11A | 1.350 (18) |
C1E—C2E | 1.511 (14) | C10A—H10A | 0.9500 |
C1E—H1E | 1.0000 | C11A—C12A | 1.431 (18) |
O5E—C5E | 1.436 (11) | C11A—C14A | 1.513 (16) |
C2E—O2E | 1.411 (13) | C12A—C13A | 1.376 (16) |
C2E—C3E | 1.521 (13) | C12A—H12A | 0.9500 |
C2E—H2E | 1.0000 | C13A—H13A | 0.9500 |
O2E—H2OE | 0.8400 | C14A—H141 | 0.9800 |
C3E—O3E | 1.422 (11) | C14A—H142 | 0.9800 |
C3E—C4E | 1.516 (13) | C14A—H143 | 0.9800 |
C3E—H3E | 1.0000 | O1W—H1W | 0.8461 |
O3E—H3OE | 0.8400 | O1W—H2W | 0.8430 |
C4E—C5E | 1.512 (15) | O2W—H3W | 0.8403 |
C4E—H4E | 1.0000 | O2W—H4W | 0.8399 |
C5E—C6E | 1.56 (2) | O3W—H5W | 0.8403 |
C5E—H5E | 1.0000 | O3W—H6W | 0.8404 |
C6E—O6E | 1.40 (2) | O4W—H7W | 0.8398 |
C6E—H6E1 | 0.9900 | O4W—H8W | 0.8404 |
C6E—H6E2 | 0.9900 | O5W—H9W | 0.8422 |
O6E—H6OE | 0.8400 | O5W—H10W | 0.8405 |
O4C—C1D | 1.400 (10) | O6W—H11W | 0.8442 |
O4C—C4C | 1.435 (10) | O6W—H12W | 0.8389 |
C1D—O5D | 1.420 (11) | O7W—H13W | 0.8397 |
C1D—C2D | 1.536 (13) | O7W—H14W | 0.8383 |
C1D—H1D | 1.0000 | O8W—H15W | 0.8453 |
O5D—C5D | 1.427 (11) | O8W—H16W | 0.8414 |
C2D—O2D | 1.412 (10) | O9W—H17W | 0.8483 |
C2D—C3D | 1.517 (13) | O9W—H18W | 0.8465 |
C2D—H2D | 1.0000 | O10W—H19W | 0.8411 |
O2D—H2OD | 0.8400 | O10W—H20W | 0.8425 |
C3D—O3D | 1.418 (9) | O11W—H21W | 0.8566 |
C3D—C4D | 1.503 (11) | O11W—H22W | 0.8465 |
C3D—H3D | 1.0000 | O12W—H23W | 0.8389 |
O3D—H3OD | 0.8400 | O12W—H24W | 0.8417 |
C4D—C5D | 1.526 (12) | O13W—H25W | 0.8406 |
C4D—H4D | 1.0000 | O13W—H26W | 0.8338 |
C5D—C6D | 1.520 (13) | O14W—H27W | 0.8594 |
C5D—H5D | 1.0000 | O14W—H28W | 0.8543 |
C6D—O6D | 1.452 (14) | | |
| | | |
C4G—O4G—C1A | 120.0 (7) | O3D—C3D—C2D | 107.4 (7) |
O5A—C1A—O4G | 110.1 (7) | C4D—C3D—C2D | 111.2 (7) |
O5A—C1A—C2A | 111.0 (7) | O3D—C3D—H3D | 108.8 |
O4G—C1A—C2A | 108.5 (7) | C4D—C3D—H3D | 108.8 |
O5A—C1A—H1A | 109.1 | C2D—C3D—H3D | 108.8 |
O4G—C1A—H1A | 109.1 | C3D—O3D—H3OD | 109.5 |
C2A—C1A—H1A | 109.1 | O4D—C4D—C3D | 107.9 (7) |
C1A—O5A—C5A | 112.8 (7) | O4D—C4D—C5D | 109.5 (7) |
O2A—C2A—C1A | 109.2 (7) | C3D—C4D—C5D | 111.7 (7) |
O2A—C2A—C3A | 113.4 (7) | O4D—C4D—H4D | 109.2 |
C1A—C2A—C3A | 110.4 (7) | C3D—C4D—H4D | 109.2 |
O2A—C2A—H2A | 107.9 | C5D—C4D—H4D | 109.2 |
C1A—C2A—H2A | 107.9 | O5D—C5D—C6D | 105.7 (8) |
C3A—C2A—H2A | 107.9 | O5D—C5D—C4D | 109.7 (7) |
C2A—O2A—H2OA | 109.5 | C6D—C5D—C4D | 111.9 (7) |
O3A—C3A—C4A | 111.1 (7) | O5D—C5D—H5D | 109.8 |
O3A—C3A—C2A | 107.7 (7) | C6D—C5D—H5D | 109.8 |
C4A—C3A—C2A | 109.7 (7) | C4D—C5D—H5D | 109.8 |
O3A—C3A—H3A | 109.4 | O6D—C6D—C5D | 110.5 (9) |
C4A—C3A—H3A | 109.4 | O6D—C6D—H6D1 | 109.5 |
C2A—C3A—H3A | 109.4 | C5D—C6D—H6D1 | 109.5 |
C3A—O3A—H3OA | 109.5 | O6D—C6D—H6D2 | 109.5 |
O4A—C4A—C3A | 108.1 (7) | C5D—C6D—H6D2 | 109.5 |
O4A—C4A—C5A | 111.2 (7) | H6D1—C6D—H6D2 | 108.1 |
C3A—C4A—C5A | 109.8 (7) | C6D—O6D—H6OD | 109.5 |
O4A—C4A—H4A | 109.3 | C1C—O4B—C4B | 118.7 (7) |
C3A—C4A—H4A | 109.3 | O5C—C1C—O4B | 110.6 (7) |
C5A—C4A—H4A | 109.3 | O5C—C1C—C2C | 111.2 (8) |
O5A—C5A—C4A | 110.0 (7) | O4B—C1C—C2C | 107.7 (7) |
O5A—C5A—C6A | 104.9 (7) | O5C—C1C—H1C | 109.1 |
C4A—C5A—C6A | 114.6 (7) | O4B—C1C—H1C | 109.1 |
O5A—C5A—H5A | 109.0 | C2C—C1C—H1C | 109.1 |
C4A—C5A—H5A | 109.0 | C1C—O5C—C5C | 114.4 (7) |
C6A—C5A—H5A | 109.0 | O2C—C2C—C1C | 112.4 (8) |
C5A—C6A—S6A | 115.7 (6) | O2C—C2C—C3C | 110.0 (8) |
C5A—C6A—H6A1 | 108.4 | C1C—C2C—C3C | 110.0 (8) |
S6A—C6A—H6A1 | 108.4 | O2C—C2C—H2C | 108.1 |
C5A—C6A—H6A2 | 108.4 | C1C—C2C—H2C | 108.1 |
S6A—C6A—H6A2 | 108.4 | C3C—C2C—H2C | 108.1 |
H6A1—C6A—H6A2 | 107.4 | C2C—O2C—H2OC | 109.5 |
C8A—C7A—S6A | 113.3 (8) | O3C—C3C—C4C | 108.4 (7) |
C8A—C7A—H7A1 | 108.9 | O3C—C3C—C2C | 110.4 (7) |
S6A—C7A—H7A1 | 108.9 | C4C—C3C—C2C | 111.3 (8) |
C8A—C7A—H7A2 | 108.9 | O3C—C3C—H3C | 108.9 |
S6A—C7A—H7A2 | 108.9 | C4C—C3C—H3C | 108.9 |
H7A1—C7A—H7A2 | 107.7 | C2C—C3C—H3C | 108.9 |
C4F—O4F—C1G | 119.6 (6) | C3C—O3C—H3OC | 109.5 |
O4F—C1G—O5G | 110.6 (7) | O4C—C4C—C3C | 107.3 (7) |
O4F—C1G—C2G | 109.1 (6) | O4C—C4C—C5C | 109.4 (7) |
O5G—C1G—C2G | 110.6 (7) | C3C—C4C—C5C | 112.7 (7) |
O4F—C1G—H1G | 108.8 | O4C—C4C—H4C | 109.1 |
O5G—C1G—H1G | 108.8 | C3C—C4C—H4C | 109.1 |
C2G—C1G—H1G | 108.8 | C5C—C4C—H4C | 109.1 |
C1G—O5G—C5G | 112.6 (6) | O5C—C5C—C6C | 105.6 (8) |
O2G—C2G—C3G | 111.6 (7) | O5C—C5C—C4C | 109.3 (7) |
O2G—C2G—C1G | 108.4 (7) | C6C—C5C—C4C | 114.3 (8) |
C3G—C2G—C1G | 110.8 (7) | O5C—C5C—H5C | 109.1 |
O2G—C2G—H2G | 108.7 | C6C—C5C—H5C | 109.1 |
C3G—C2G—H2G | 108.7 | C4C—C5C—H5C | 109.1 |
C1G—C2G—H2G | 108.7 | O6C—C6C—C5C | 112.0 (9) |
C2G—O2G—H2OG | 109.5 | O6C—C6C—H6C1 | 109.2 |
O3G—C3G—C2G | 112.7 (7) | C5C—C6C—H6C1 | 109.2 |
O3G—C3G—C4G | 108.8 (6) | O6C—C6C—H6C2 | 109.2 |
C2G—C3G—C4G | 112.8 (7) | C5C—C6C—H6C2 | 109.2 |
O3G—C3G—H3G | 107.4 | H6C1—C6C—H6C2 | 107.9 |
C2G—C3G—H3G | 107.4 | C6C—O6C—H6OC | 109.5 |
C4G—C3G—H3G | 107.4 | C1B—O4A—C4A | 119.1 (6) |
C3G—O3G—H3OG | 109.5 | O4A—C1B—O5B | 111.7 (7) |
O4G—C4G—C5G | 111.1 (7) | O4A—C1B—C2B | 110.4 (7) |
O4G—C4G—C3G | 106.9 (7) | O5B—C1B—C2B | 110.3 (7) |
C5G—C4G—C3G | 110.3 (7) | O4A—C1B—H1B | 108.1 |
O4G—C4G—H4G | 109.5 | O5B—C1B—H1B | 108.1 |
C5G—C4G—H4G | 109.5 | C2B—C1B—H1B | 108.1 |
C3G—C4G—H4G | 109.5 | C5B—O5B—C1B | 112.3 (6) |
O5G—C5G—C6G | 106.5 (6) | O2B—C2B—C1B | 110.1 (8) |
O5G—C5G—C4G | 110.2 (7) | O2B—C2B—C3B | 111.7 (8) |
C6G—C5G—C4G | 114.7 (7) | C1B—C2B—C3B | 110.6 (7) |
O5G—C5G—H5G | 108.5 | O2B—C2B—H2B | 108.1 |
C6G—C5G—H5G | 108.5 | C1B—C2B—H2B | 108.1 |
C4G—C5G—H5G | 108.5 | C3B—C2B—H2B | 108.1 |
O6G—C6G—C5G | 110.9 (8) | C2B—O2B—H2OB | 109.5 |
O6G—C6G—H6G1 | 109.5 | O3B—C3B—C4B | 110.4 (8) |
C5G—C6G—H6G1 | 109.5 | O3B—C3B—C2B | 110.5 (7) |
O6G—C6G—H6G2 | 109.5 | C4B—C3B—C2B | 109.9 (7) |
C5G—C6G—H6G2 | 109.5 | O3B—C3B—H3B | 108.7 |
H6G1—C6G—H6G2 | 108.0 | C4B—C3B—H3B | 108.7 |
C6G—O6G—H6OG | 109.5 | C2B—C3B—H3B | 108.7 |
C1F—O4E—C4E | 119.0 (6) | C3B—O3B—H3OB | 109.5 |
O5F—C1F—O4E | 111.4 (8) | O4B—C4B—C5B | 110.4 (7) |
O5F—C1F—C2F | 110.2 (7) | O4B—C4B—C3B | 106.4 (7) |
O4E—C1F—C2F | 108.0 (7) | C5B—C4B—C3B | 110.5 (8) |
O5F—C1F—H1F | 109.1 | O4B—C4B—H4B | 109.8 |
O4E—C1F—H1F | 109.1 | C5B—C4B—H4B | 109.8 |
C2F—C1F—H1F | 109.1 | C3B—C4B—H4B | 109.8 |
C1F—O5F—C5F | 113.9 (6) | O5B—C5B—C4B | 110.1 (7) |
O2F—C2F—C3F | 111.0 (8) | O5B—C5B—C6B | 106.2 (7) |
O2F—C2F—C1F | 109.4 (7) | C4B—C5B—C6B | 112.2 (8) |
C3F—C2F—C1F | 110.4 (8) | O5B—C5B—H5B | 109.4 |
O2F—C2F—H2F | 108.7 | C4B—C5B—H5B | 109.4 |
C3F—C2F—H2F | 108.7 | C6B—C5B—H5B | 109.4 |
C1F—C2F—H2F | 108.7 | C5B—C6B—S6B | 117.9 (7) |
C2F—O2F—H2OF | 109.5 | C5B—C6B—H6B1 | 107.8 |
O3F—C3F—C4F | 110.8 (7) | S6B—C6B—H6B1 | 107.8 |
O3F—C3F—C2F | 111.2 (8) | C5B—C6B—H6B2 | 107.8 |
C4F—C3F—C2F | 111.4 (8) | S6B—C6B—H6B2 | 107.8 |
O3F—C3F—H3F | 107.8 | H6B1—C6B—H6B2 | 107.2 |
C4F—C3F—H3F | 107.8 | C17B—C7B—C8B | 104.2 (16) |
C2F—C3F—H3F | 107.8 | C17B—C7B—C13B | 127.2 (15) |
C3F—O3F—H3OF | 109.5 | C8B—C7B—C12B | 107.5 (14) |
O4F—C4F—C3F | 108.2 (7) | C13B—C7B—C12B | 127.3 (12) |
O4F—C4F—C5F | 111.9 (8) | C17B—C7B—S6B | 122.8 (12) |
C3F—C4F—C5F | 112.0 (7) | C8B—C7B—S6B | 130.4 (12) |
O4F—C4F—H4F | 108.2 | C13B—C7B—S6B | 109.3 (8) |
C3F—C4F—H4F | 108.2 | C12B—C7B—S6B | 122.1 (9) |
C5F—C4F—H4F | 108.2 | C7B—C8B—C9B | 129 (2) |
O5F—C5F—C4F | 110.5 (8) | C7B—C8B—H8B | 115.6 |
O5F—C5F—C6F | 107.0 (7) | C9B—C8B—H8B | 115.6 |
C4F—C5F—C6F | 114.4 (8) | C10B—C9B—C8B | 119 (2) |
O5F—C5F—H5F | 108.2 | C10B—C9B—H9B | 120.6 |
C4F—C5F—H5F | 108.2 | C8B—C9B—H9B | 120.6 |
C6F—C5F—H5F | 108.2 | C9B—C10B—C11B | 119 (2) |
O6F—C6F—C5F | 110.8 (11) | C9B—C10B—H10B | 120.3 |
O6F—C6F—H6F1 | 109.5 | C11B—C10B—H10B | 120.3 |
C5F—C6F—H6F1 | 109.5 | C10B—C11B—C12B | 117 (2) |
O6F—C6F—H6F2 | 109.5 | C10B—C11B—H11B | 121.3 |
C5F—C6F—H6F2 | 109.5 | C12B—C11B—H11B | 121.3 |
H6F1—C6F—H6F2 | 108.1 | C11B—C12B—C7B | 128.1 (17) |
C6F—O6F—H6OF | 109.5 | C11B—C12B—H12B | 116.0 |
C1E—O4D—C4D | 116.9 (6) | C7B—C12B—H12B | 116.0 |
O5E—C1E—O4D | 110.7 (7) | C7B—C13B—C14B | 116.9 (13) |
O5E—C1E—C2E | 112.3 (7) | C7B—C13B—H13B | 121.6 |
O4D—C1E—C2E | 108.5 (8) | C14B—C13B—H13B | 121.6 |
O5E—C1E—H1E | 108.4 | C15B—C14B—C13B | 119.9 (15) |
O4D—C1E—H1E | 108.4 | C15B—C14B—H14B | 120.1 |
C2E—C1E—H1E | 108.4 | C13B—C14B—H14B | 120.1 |
C1E—O5E—C5E | 113.8 (6) | C14B—C15B—C16B | 118.1 (18) |
O2E—C2E—C1E | 109.4 (8) | C14B—C15B—H15B | 121.0 |
O2E—C2E—C3E | 109.3 (8) | C16B—C15B—H15B | 121.0 |
C1E—C2E—C3E | 110.4 (7) | C15B—C16B—C17B | 125 (2) |
O2E—C2E—H2E | 109.2 | C15B—C16B—H16B | 117.5 |
C1E—C2E—H2E | 109.2 | C17B—C16B—H16B | 117.5 |
C3E—C2E—H2E | 109.2 | C7B—C17B—C16B | 112 (2) |
C2E—O2E—H2OE | 109.5 | C7B—C17B—H17B | 124.0 |
O3E—C3E—C4E | 111.5 (8) | C16B—C17B—H17B | 124.0 |
O3E—C3E—C2E | 110.7 (7) | C9A—C8A—C13A | 118.3 (10) |
C4E—C3E—C2E | 109.5 (8) | C9A—C8A—C7A | 121.4 (13) |
O3E—C3E—H3E | 108.4 | C13A—C8A—C7A | 120.3 (13) |
C4E—C3E—H3E | 108.4 | C8A—C9A—C10A | 122.6 (11) |
C2E—C3E—H3E | 108.4 | C8A—C9A—H9A | 118.7 |
C3E—O3E—H3OE | 109.5 | C10A—C9A—H9A | 118.7 |
O4E—C4E—C5E | 110.0 (8) | C11A—C10A—C9A | 120.7 (12) |
O4E—C4E—C3E | 107.5 (7) | C11A—C10A—H10A | 119.6 |
C5E—C4E—C3E | 109.8 (7) | C9A—C10A—H10A | 119.6 |
O4E—C4E—H4E | 109.8 | C10A—C11A—C12A | 116.8 (10) |
C5E—C4E—H4E | 109.8 | C10A—C11A—C14A | 123.9 (14) |
C3E—C4E—H4E | 109.8 | C12A—C11A—C14A | 119.4 (14) |
O5E—C5E—C4E | 111.0 (8) | C13A—C12A—C11A | 120.4 (11) |
O5E—C5E—C6E | 104.5 (8) | C13A—C12A—H12A | 119.8 |
C4E—C5E—C6E | 119.4 (10) | C11A—C12A—H12A | 119.8 |
O5E—C5E—H5E | 107.1 | C8A—C13A—C12A | 121.1 (12) |
C4E—C5E—H5E | 107.1 | C8A—C13A—H13A | 119.5 |
C6E—C5E—H5E | 107.1 | C12A—C13A—H13A | 119.5 |
O6E—C6E—C5E | 104.3 (16) | C11A—C14A—H141 | 109.5 |
O6E—C6E—H6E1 | 110.9 | C11A—C14A—H142 | 109.5 |
C5E—C6E—H6E1 | 110.9 | H141—C14A—H142 | 109.5 |
O6E—C6E—H6E2 | 110.9 | C11A—C14A—H143 | 109.5 |
C5E—C6E—H6E2 | 110.9 | H141—C14A—H143 | 109.5 |
H6E1—C6E—H6E2 | 108.9 | H142—C14A—H143 | 109.5 |
C6E—O6E—H6OE | 109.5 | C6B—S6B—C7B | 107.0 (4) |
C1D—O4C—C4C | 119.4 (7) | C7A—S6A—C6A | 98.9 (6) |
O4C—C1D—O5D | 110.7 (7) | H1W—O1W—H2W | 107.1 |
O4C—C1D—C2D | 107.0 (7) | H3W—O2W—H4W | 107.9 |
O5D—C1D—C2D | 110.1 (7) | H5W—O3W—H6W | 107.9 |
O4C—C1D—H1D | 109.6 | H7W—O4W—H8W | 107.9 |
O5D—C1D—H1D | 109.6 | H9W—O5W—H10W | 107.7 |
C2D—C1D—H1D | 109.6 | H11W—O6W—H12W | 107.7 |
C1D—O5D—C5D | 114.7 (6) | H13W—O7W—H14W | 108.2 |
O2D—C2D—C3D | 112.5 (7) | H15W—O8W—H16W | 107.3 |
O2D—C2D—C1D | 110.9 (7) | H17W—O9W—H18W | 106.6 |
C3D—C2D—C1D | 111.0 (7) | H19W—O10W—H20W | 107.6 |
O2D—C2D—H2D | 107.4 | H21W—O11W—H22W | 105.9 |
C3D—C2D—H2D | 107.4 | H23W—O12W—H24W | 107.9 |
C1D—C2D—H2D | 107.4 | H25W—O13W—H26W | 108.5 |
C2D—O2D—H2OD | 109.5 | H27W—O14W—H28W | 104.9 |
O3D—C3D—C4D | 112.0 (7) | | |
| | | |
C4G—O4G—C1A—O5A | 113.7 (8) | C1D—C2D—C3D—C4D | −50.6 (10) |
C4G—O4G—C1A—C2A | −124.6 (8) | C1E—O4D—C4D—C3D | 123.5 (8) |
O4G—C1A—O5A—C5A | 60.9 (9) | C1E—O4D—C4D—C5D | −114.7 (8) |
C2A—C1A—O5A—C5A | −59.2 (9) | O3D—C3D—C4D—O4D | −68.3 (9) |
O5A—C1A—C2A—O2A | −179.1 (7) | C2D—C3D—C4D—O4D | 171.7 (7) |
O4G—C1A—C2A—O2A | 59.8 (9) | O3D—C3D—C4D—C5D | 171.3 (7) |
O5A—C1A—C2A—C3A | 55.6 (9) | C2D—C3D—C4D—C5D | 51.3 (10) |
O4G—C1A—C2A—C3A | −65.5 (9) | C1D—O5D—C5D—C6D | −179.5 (7) |
O2A—C2A—C3A—O3A | 61.8 (9) | C1D—O5D—C5D—C4D | 59.7 (9) |
C1A—C2A—C3A—O3A | −175.3 (7) | O4D—C4D—C5D—O5D | −173.7 (6) |
O2A—C2A—C3A—C4A | −177.1 (7) | C3D—C4D—C5D—O5D | −54.2 (9) |
C1A—C2A—C3A—C4A | −54.2 (10) | O4D—C4D—C5D—C6D | 69.4 (9) |
O3A—C3A—C4A—O4A | −64.2 (9) | C3D—C4D—C5D—C6D | −171.1 (8) |
C2A—C3A—C4A—O4A | 176.8 (7) | O5D—C5D—C6D—O6D | −60.5 (9) |
O3A—C3A—C4A—C5A | 174.4 (7) | C4D—C5D—C6D—O6D | 58.9 (11) |
C2A—C3A—C4A—C5A | 55.4 (9) | C4B—O4B—C1C—O5C | 109.9 (8) |
C1A—O5A—C5A—C4A | 60.2 (9) | C4B—O4B—C1C—C2C | −128.4 (8) |
C1A—O5A—C5A—C6A | −176.1 (7) | O4B—C1C—O5C—C5C | 58.6 (9) |
O4A—C4A—C5A—O5A | −177.2 (7) | C2C—C1C—O5C—C5C | −61.1 (10) |
C3A—C4A—C5A—O5A | −57.7 (9) | O5C—C1C—C2C—O2C | 178.3 (7) |
O4A—C4A—C5A—C6A | 64.9 (10) | O4B—C1C—C2C—O2C | 57.0 (10) |
C3A—C4A—C5A—C6A | −175.6 (8) | O5C—C1C—C2C—C3C | 55.5 (10) |
O5A—C5A—C6A—S6A | 68.2 (9) | O4B—C1C—C2C—C3C | −65.9 (10) |
C4A—C5A—C6A—S6A | −171.1 (7) | O2C—C2C—C3C—O3C | 64.5 (10) |
C4F—O4F—C1G—O5G | 108.0 (8) | C1C—C2C—C3C—O3C | −171.2 (7) |
C4F—O4F—C1G—C2G | −130.2 (8) | O2C—C2C—C3C—C4C | −175.1 (7) |
O4F—C1G—O5G—C5G | 59.0 (8) | C1C—C2C—C3C—C4C | −50.8 (10) |
C2G—C1G—O5G—C5G | −62.0 (8) | C1D—O4C—C4C—C3C | 128.3 (8) |
O4F—C1G—C2G—O2G | 55.1 (9) | C1D—O4C—C4C—C5C | −109.1 (9) |
O5G—C1G—C2G—O2G | 176.9 (6) | O3C—C3C—C4C—O4C | −67.7 (9) |
O4F—C1G—C2G—C3G | −67.7 (9) | C2C—C3C—C4C—O4C | 170.7 (7) |
O5G—C1G—C2G—C3G | 54.1 (9) | O3C—C3C—C4C—C5C | 171.8 (7) |
O2G—C2G—C3G—O3G | 66.4 (9) | C2C—C3C—C4C—C5C | 50.2 (10) |
C1G—C2G—C3G—O3G | −172.7 (6) | C1C—O5C—C5C—C6C | −178.6 (7) |
O2G—C2G—C3G—C4G | −169.9 (7) | C1C—O5C—C5C—C4C | 58.0 (10) |
C1G—C2G—C3G—C4G | −49.0 (9) | O4C—C4C—C5C—O5C | −171.2 (7) |
C1A—O4G—C4G—C5G | −103.6 (8) | C3C—C4C—C5C—O5C | −51.9 (10) |
C1A—O4G—C4G—C3G | 136.0 (7) | O4C—C4C—C5C—C6C | 70.6 (10) |
O3G—C3G—C4G—O4G | −63.9 (8) | C3C—C4C—C5C—C6C | −170.1 (8) |
C2G—C3G—C4G—O4G | 170.2 (6) | O5C—C5C—C6C—O6C | 67.9 (10) |
O3G—C3G—C4G—C5G | 175.1 (6) | C4C—C5C—C6C—O6C | −171.8 (8) |
C2G—C3G—C4G—C5G | 49.3 (9) | C3A—C4A—O4A—C1B | 113.3 (8) |
C1G—O5G—C5G—C6G | −172.8 (7) | C5A—C4A—O4A—C1B | −126.2 (8) |
C1G—O5G—C5G—C4G | 62.3 (8) | C4A—O4A—C1B—O5B | 105.3 (8) |
O4G—C4G—C5G—O5G | −172.6 (6) | C4A—O4A—C1B—C2B | −131.6 (8) |
C3G—C4G—C5G—O5G | −54.3 (9) | O4A—C1B—O5B—C5B | 62.5 (9) |
O4G—C4G—C5G—C6G | 67.3 (9) | C2B—C1B—O5B—C5B | −60.7 (9) |
C3G—C4G—C5G—C6G | −174.3 (7) | O4A—C1B—C2B—O2B | 56.4 (10) |
O5G—C5G—C6G—O6G | −65.9 (8) | O5B—C1B—C2B—O2B | −179.6 (7) |
C4G—C5G—C6G—O6G | 56.1 (9) | O4A—C1B—C2B—C3B | −67.6 (10) |
C4E—O4E—C1F—O5F | 111.2 (8) | O5B—C1B—C2B—C3B | 56.4 (9) |
C4E—O4E—C1F—C2F | −127.6 (8) | O2B—C2B—C3B—O3B | 61.6 (10) |
O4E—C1F—O5F—C5F | 58.6 (10) | C1B—C2B—C3B—O3B | −175.4 (7) |
C2F—C1F—O5F—C5F | −61.3 (10) | O2B—C2B—C3B—C4B | −176.4 (7) |
O5F—C1F—C2F—O2F | 179.9 (7) | C1B—C2B—C3B—C4B | −53.4 (10) |
O4E—C1F—C2F—O2F | 58.0 (9) | C1C—O4B—C4B—C5B | −109.6 (9) |
O5F—C1F—C2F—C3F | 57.4 (9) | C1C—O4B—C4B—C3B | 130.4 (8) |
O4E—C1F—C2F—C3F | −64.5 (9) | O3B—C3B—C4B—O4B | −64.3 (9) |
O2F—C2F—C3F—O3F | 62.3 (10) | C2B—C3B—C4B—O4B | 173.5 (7) |
C1F—C2F—C3F—O3F | −176.2 (7) | O3B—C3B—C4B—C5B | 175.7 (7) |
O2F—C2F—C3F—C4F | −173.5 (7) | C2B—C3B—C4B—C5B | 53.6 (9) |
C1F—C2F—C3F—C4F | −52.1 (9) | C1B—O5B—C5B—C4B | 60.9 (9) |
C1G—O4F—C4F—C3F | 124.0 (8) | C1B—O5B—C5B—C6B | −177.4 (7) |
C1G—O4F—C4F—C5F | −112.1 (8) | O4B—C4B—C5B—O5B | −174.4 (7) |
O3F—C3F—C4F—O4F | −62.5 (9) | C3B—C4B—C5B—O5B | −56.9 (9) |
C2F—C3F—C4F—O4F | 173.1 (7) | O4B—C4B—C5B—C6B | 67.4 (9) |
O3F—C3F—C4F—C5F | 173.7 (7) | C3B—C4B—C5B—C6B | −175.0 (7) |
C2F—C3F—C4F—C5F | 49.4 (10) | O5B—C5B—C6B—S6B | 75.1 (9) |
C1F—O5F—C5F—C4F | 57.8 (10) | C4B—C5B—C6B—S6B | −164.5 (6) |
C1F—O5F—C5F—C6F | −177.1 (9) | C17B—C7B—C8B—C9B | −18.2 (18) |
O4F—C4F—C5F—O5F | −172.1 (7) | C13B—C7B—C8B—C9B | 149 (3) |
C3F—C4F—C5F—O5F | −50.5 (10) | C12B—C7B—C8B—C9B | −0.2 (15) |
O4F—C4F—C5F—C6F | 67.0 (11) | S6B—C7B—C8B—C9B | −179.5 (11) |
C3F—C4F—C5F—C6F | −171.4 (8) | C7B—C8B—C9B—C10B | 0.1 (19) |
O5F—C5F—C6F—O6F | −62.6 (11) | C8B—C9B—C10B—C11B | −1 (3) |
C4F—C5F—C6F—O6F | 60.2 (11) | C9B—C10B—C11B—C12B | 3 (3) |
C4D—O4D—C1E—O5E | 112.5 (8) | C10B—C11B—C12B—C7B | −3 (3) |
C4D—O4D—C1E—C2E | −123.9 (7) | C17B—C7B—C12B—C11B | 83 (5) |
O4D—C1E—O5E—C5E | 64.4 (10) | C8B—C7B—C12B—C11B | 2 (3) |
C2E—C1E—O5E—C5E | −57.0 (10) | C13B—C7B—C12B—C11B | −13 (3) |
O5E—C1E—C2E—O2E | 174.8 (7) | S6B—C7B—C12B—C11B | −178.9 (17) |
O4D—C1E—C2E—O2E | 52.2 (9) | C17B—C7B—C13B—C14B | −3.9 (18) |
O5E—C1E—C2E—C3E | 54.5 (10) | C8B—C7B—C13B—C14B | −19 (2) |
O4D—C1E—C2E—C3E | −68.2 (10) | C12B—C7B—C13B—C14B | 18.2 (17) |
O2E—C2E—C3E—O3E | 62.8 (10) | S6B—C7B—C13B—C14B | −174.6 (9) |
C1E—C2E—C3E—O3E | −176.8 (8) | C7B—C13B—C14B—C15B | 1.8 (15) |
O2E—C2E—C3E—C4E | −173.9 (8) | C13B—C14B—C15B—C16B | −5 (2) |
C1E—C2E—C3E—C4E | −53.5 (11) | C14B—C15B—C16B—C17B | 11 (3) |
C1F—O4E—C4E—C5E | −118.1 (9) | C8B—C7B—C17B—C16B | 15 (2) |
C1F—O4E—C4E—C3E | 122.4 (8) | C13B—C7B—C17B—C16B | 8 (3) |
O3E—C3E—C4E—O4E | −62.7 (10) | C12B—C7B—C17B—C16B | −89 (5) |
C2E—C3E—C4E—O4E | 174.5 (7) | S6B—C7B—C17B—C16B | 177.9 (14) |
O3E—C3E—C4E—C5E | 177.7 (8) | C15B—C16B—C17B—C7B | −12 (3) |
C2E—C3E—C4E—C5E | 54.9 (10) | S6A—C7A—C8A—C9A | −90.9 (15) |
C1E—O5E—C5E—C4E | 58.1 (10) | S6A—C7A—C8A—C13A | 90.1 (14) |
C1E—O5E—C5E—C6E | −171.9 (10) | C13A—C8A—C9A—C10A | 4.4 (19) |
O4E—C4E—C5E—O5E | −174.4 (6) | C7A—C8A—C9A—C10A | −174.6 (12) |
C3E—C4E—C5E—O5E | −56.3 (10) | C8A—C9A—C10A—C11A | −2 (2) |
O4E—C4E—C5E—C6E | 63.9 (12) | C9A—C10A—C11A—C12A | −0.8 (18) |
C3E—C4E—C5E—C6E | −177.9 (9) | C9A—C10A—C11A—C14A | −179.9 (13) |
O5E—C5E—C6E—O6E | −65.7 (13) | C10A—C11A—C12A—C13A | 1.7 (18) |
C4E—C5E—C6E—O6E | 59.1 (14) | C14A—C11A—C12A—C13A | −179.2 (13) |
C4C—O4C—C1D—O5D | 111.0 (8) | C9A—C8A—C13A—C12A | −3.5 (19) |
C4C—O4C—C1D—C2D | −129.0 (7) | C7A—C8A—C13A—C12A | 175.6 (12) |
O4C—C1D—O5D—C5D | 58.5 (9) | C11A—C12A—C13A—C8A | 0 (2) |
C2D—C1D—O5D—C5D | −59.6 (9) | C5B—C6B—S6B—C7B | −80.0 (7) |
O4C—C1D—C2D—O2D | 58.9 (9) | C17B—C7B—S6B—C6B | −9.8 (16) |
O5D—C1D—C2D—O2D | 179.3 (7) | C8B—C7B—S6B—C6B | 148.5 (11) |
O4C—C1D—C2D—C3D | −67.0 (9) | C13B—C7B—S6B—C6B | 161.3 (7) |
O5D—C1D—C2D—C3D | 53.5 (9) | C12B—C7B—S6B—C6B | −30.7 (13) |
O2D—C2D—C3D—O3D | 61.7 (9) | C8A—C7A—S6A—C6A | 148.7 (12) |
C1D—C2D—C3D—O3D | −173.4 (7) | C5A—C6A—S6A—C7A | 63.7 (9) |
O2D—C2D—C3D—C4D | −175.6 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O3G | 0.84 | 2.06 | 2.89 (1) | 166 |
O3A—H3OA···O2B | 0.84 | 1.95 | 2.76 (1) | 162 |
O2B—H2OB···O13Wi | 0.84 | 2.16 | 2.87 (2) | 143 |
O3B—H3OB···S6Aii | 0.84 | 2.69 | 3.431 (7) | 149 |
O2C—H2OC···O3B | 0.84 | 2.16 | 2.92 (1) | 150 |
O3C—H3OC···O6Gii | 0.84 | 2.17 | 2.798 (9) | 132 |
O6C—H6OC···O10W | 0.84 | 2.15 | 2.82 (1) | 137 |
O2D—H2OD···O3C | 0.84 | 2.18 | 2.87 (1) | 139 |
O3D—H3OD···O2E | 0.84 | 1.91 | 2.72 (1) | 159 |
O6D—H6OD···O2Wii | 0.84 | 2.31 | 2.67 (1) | 106 |
O2E—H2OE···O3E | 0.84 | 2.42 | 2.85 (1) | 113 |
O3E—H3OE···O2F | 0.84 | 2.02 | 2.72 (1) | 141 |
O6E—H6OE···O6Wii | 0.84 | 1.83 | 2.65 (2) | 166 |
O2F—H2OF···O8W | 0.84 | 1.80 | 2.57 (2) | 152 |
O3F—H3OF···O2G | 0.84 | 1.96 | 2.79 (1) | 169 |
O6F—H6OF···O3Giii | 0.84 | 1.93 | 2.73 (1) | 159 |
O2G—H2OG···O5Cii | 0.84 | 2.57 | 3.24 (1) | 137 |
O3G—H3OG···O6Cii | 0.84 | 2.20 | 2.75 (1) | 123 |
O6G—H6OG···O4Wiv | 0.84 | 1.98 | 2.77 (1) | 158 |
O1W—H1W···O3F | 0.85 | 2.26 | 3.10 (3) | 173 |
O1W—H2W···O2Dv | 0.84 | 2.30 | 3.10 (3) | 160 |
O2W—H3W···O3Avi | 0.84 | 1.86 | 2.64 (1) | 154 |
O2W—H4W···O10Wvii | 0.84 | 2.11 | 2.94 (1) | 171 |
O3W—H5W···O6Fviii | 0.84 | 1.99 | 2.76 (1) | 153 |
O3W—H6W···O6Ei | 0.84 | 2.43 | 3.24 (2) | 161 |
O4W—H7W···O3W | 0.84 | 1.97 | 2.78 (1) | 161 |
O4W—H8W···O5W | 0.84 | 1.91 | 2.73 (2) | 167 |
O5W—H9W···O5Dvii | 0.84 | 2.32 | 3.09 (1) | 151 |
O5W—H9W···O6Dvii | 0.84 | 2.40 | 3.05 (2) | 135 |
O5W—H10W···O3Ei | 0.84 | 2.10 | 2.81 (2) | 143 |
O6W—H11W···O3Dix | 0.84 | 2.31 | 2.84 (2) | 121 |
O6W—H12W···O2Avi | 0.84 | 2.20 | 2.89 (2) | 139 |
O7W—H13W···O2Gx | 0.84 | 1.88 | 2.69 (1) | 161 |
O7W—H14W···O11W | 0.84 | 2.25 | 2.79 (3) | 123 |
O8W—H15W···O3Cv | 0.85 | 2.14 | 2.90 (2) | 149 |
O8W—H16W···O1W | 0.84 | 2.18 | 2.64 (3) | 114 |
O9W—H17W···O1Wx | 0.85 | 2.18 | 3.03 (4) | 178 |
O9W—H18W···O11Wx | 0.85 | 2.17 | 2.64 (4) | 115 |
O10W—H19W···O6C | 0.84 | 2.30 | 2.82 (1) | 121 |
O10W—H20W···O3Wxi | 0.84 | 1.95 | 2.76 (1) | 159 |
O11W—H21W···O7W | 0.86 | 2.05 | 2.79 (3) | 145 |
O11W—H22W···O9Wxii | 0.85 | 1.97 | 2.64 (4) | 134 |
O12W—H23W···O7W | 0.84 | 2.15 | 2.85 (4) | 141 |
O12W—H24W···O1Wx | 0.84 | 1.99 | 2.58 (3) | 126 |
O13W—H25W···O12W | 0.84 | 2.54 | 3.02 (4) | 117 |
O13W—H25W···O11W | 0.84 | 2.62 | 3.26 (4) | 134 |
O13W—H26W···O5Wii | 0.83 | 1.86 | 2.67 (4) | 163 |
O14W—H27W···O3Fx | 0.86 | 2.25 | 2.98 (4) | 142 |
O14W—H28W···O2Dxiii | 0.85 | 1.84 | 2.61 (4) | 151 |
Symmetry codes: (i) x−1/2, −y−1/2, −z; (ii) x+1/2, −y−1/2, −z; (iii) −x, y+1/2, −z+1/2; (iv) −x−1/2, −y−1, z+1/2; (v) −x+1/2, −y, z+1/2; (vi) x−1/2, −y−3/2, −z; (vii) x, y−1, z; (viii) −x−1/2, −y−1, z−1/2; (ix) x−1, y−1, z; (x) −x+1, y+1/2, −z+1/2; (xi) x, y+1, z; (xii) −x+1, y−1/2, −z+1/2; (xiii) x+1/2, −y+1/2, −z. |
Experimental details
Crystal data |
Chemical formula | C56H82O33S2·14H2O |
Mr | 1599.56 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 14.4635 (7), 17.337 (1), 29.388 (2) |
V (Å3) | 7369.1 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34217, 9891, 4958 |
Rint | 0.118 |
(sin θ/λ)max (Å−1) | 0.667 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.096, 0.255, 1.10 |
No. of reflections | 9891 |
No. of parameters | 941 |
No. of restraints | 700 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.71, −0.46 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O3G | 0.84 | 2.06 | 2.89 (1) | 166 |
O3A—H3OA···O2B | 0.84 | 1.95 | 2.76 (1) | 162 |
O2B—H2OB···O13Wi | 0.84 | 2.16 | 2.87 (2) | 143 |
O3B—H3OB···S6Aii | 0.84 | 2.69 | 3.431 (7) | 149 |
O2C—H2OC···O3B | 0.84 | 2.16 | 2.92 (1) | 150 |
O3C—H3OC···O6Gii | 0.84 | 2.17 | 2.798 (9) | 132 |
O6C—H6OC···O10W | 0.84 | 2.15 | 2.82 (1) | 137 |
O2D—H2OD···O3C | 0.84 | 2.18 | 2.87 (1) | 139 |
O3D—H3OD···O2E | 0.84 | 1.91 | 2.72 (1) | 159 |
O6D—H6OD···O2Wii | 0.84 | 2.31 | 2.67 (1) | 106 |
O2E—H2OE···O3E | 0.84 | 2.42 | 2.85 (1) | 113 |
O3E—H3OE···O2F | 0.84 | 2.02 | 2.72 (1) | 141 |
O6E—H6OE···O6Wii | 0.84 | 1.83 | 2.65 (2) | 166 |
O2F—H2OF···O8W | 0.84 | 1.80 | 2.57 (2) | 152 |
O3F—H3OF···O2G | 0.84 | 1.96 | 2.79 (1) | 169 |
O6F—H6OF···O3Giii | 0.84 | 1.93 | 2.73 (1) | 159 |
O2G—H2OG···O5Cii | 0.84 | 2.57 | 3.24 (1) | 137 |
O3G—H3OG···O6Cii | 0.84 | 2.20 | 2.75 (1) | 123 |
O6G—H6OG···O4Wiv | 0.84 | 1.98 | 2.77 (1) | 158 |
O1W—H1W···O3F | 0.85 | 2.26 | 3.10 (3) | 173 |
O1W—H2W···O2Dv | 0.84 | 2.30 | 3.10 (3) | 160 |
O2W—H3W···O3Avi | 0.84 | 1.86 | 2.64 (1) | 154 |
O2W—H4W···O10Wvii | 0.84 | 2.11 | 2.94 (1) | 171 |
O3W—H5W···O6Fviii | 0.84 | 1.99 | 2.76 (1) | 153 |
O3W—H6W···O6Ei | 0.84 | 2.43 | 3.24 (2) | 161 |
O4W—H7W···O3W | 0.84 | 1.97 | 2.78 (1) | 161 |
O4W—H8W···O5W | 0.84 | 1.91 | 2.73 (2) | 167 |
O5W—H9W···O5Dvii | 0.84 | 2.32 | 3.09 (1) | 151 |
O5W—H9W···O6Dvii | 0.84 | 2.40 | 3.05 (2) | 135 |
O5W—H10W···O3Ei | 0.84 | 2.10 | 2.81 (2) | 143 |
O6W—H11W···O3Dix | 0.84 | 2.31 | 2.84 (2) | 121 |
O6W—H12W···O2Avi | 0.84 | 2.20 | 2.89 (2) | 139 |
O7W—H13W···O2Gx | 0.84 | 1.88 | 2.69 (1) | 161 |
O7W—H14W···O11W | 0.84 | 2.25 | 2.79 (3) | 123 |
O8W—H15W···O3Cv | 0.85 | 2.14 | 2.90 (2) | 149 |
O8W—H16W···O1W | 0.84 | 2.18 | 2.64 (3) | 114 |
O9W—H17W···O1Wx | 0.85 | 2.18 | 3.03 (4) | 178 |
O9W—H18W···O11Wx | 0.85 | 2.17 | 2.64 (4) | 115 |
O10W—H19W···O6C | 0.84 | 2.30 | 2.82 (1) | 121 |
O10W—H20W···O3Wxi | 0.84 | 1.95 | 2.76 (1) | 159 |
O11W—H21W···O7W | 0.86 | 2.05 | 2.79 (3) | 145 |
O11W—H22W···O9Wxii | 0.85 | 1.97 | 2.64 (4) | 134 |
O12W—H23W···O7W | 0.84 | 2.15 | 2.85 (4) | 141 |
O12W—H24W···O1Wx | 0.84 | 1.99 | 2.58 (3) | 126 |
O13W—H25W···O12W | 0.84 | 2.54 | 3.02 (4) | 117 |
O13W—H25W···O11W | 0.84 | 2.62 | 3.26 (4) | 134 |
O13W—H26W···O5Wii | 0.83 | 1.86 | 2.67 (4) | 163 |
O14W—H27W···O3Fx | 0.86 | 2.25 | 2.98 (4) | 142 |
O14W—H28W···O2Dxiii | 0.85 | 1.84 | 2.61 (4) | 151 |
Symmetry codes: (i) x−1/2, −y−1/2, −z; (ii) x+1/2, −y−1/2, −z; (iii) −x, y+1/2, −z+1/2; (iv) −x−1/2, −y−1, z+1/2; (v) −x+1/2, −y, z+1/2; (vi) x−1/2, −y−3/2, −z; (vii) x, y−1, z; (viii) −x−1/2, −y−1, z−1/2; (ix) x−1, y−1, z; (x) −x+1, y+1/2, −z+1/2; (xi) x, y+1, z; (xii) −x+1, y−1/2, −z+1/2; (xiii) x+1/2, −y+1/2, −z. |
As compared to the abundance of cyclodextrin (CD) inclusion compounds which have been determined by X-ray crystallography (Saenger, 1984; Harata, 1996), relatively few structures of substituted CD's other than O-methylated derivatives have been elucidated (Harata, 1998). In the case of β-CD's monosubstituted at the primary carbon (C-6), the tethered substituent of one β-CD unit, such as t-butylthio (Hirotsu et al., 1982; Fujita et al., 1985), phenylthio and phenylsulfinyl (Kamitori et al., 1987), azido (Charpin et al., 1990), 2-hydroxypropyloxy (Harata et al., 1991) and (6-aminohexyl)amino (Mentzafos et al., 1996), is included in the cavity of another substituted β-CD. This simultaneous functioning of a molecule as host and guest provides unique three-dimensional self-assemblies, most notably helical polymers (Hirotsu et al., 1982; Kamitori et al., 1987). We report herein the X-ray crystallographic study of 6I,6II-dideoxy-6I-(p-methylbenzylthio)-6II-phenylthio-β-cyclo- dextrin, (I), a β-CD derivative carrying two different substituents at the primary C-6 of vicinal glucopyranosyl residues, with the unique result that exclusively the phenylthio moiety is intermolecularly included into the cavity of another unit, making it a unique case of guest differentiation. The molecular structure of (I) is shown in Fig. 1. The β-CD-macrocycle has an approximate sevenfold axis and a round shape, with all glucose residues in the 4C1 chair conformation. The secondary hydroxyl groups between neighbouring glucose residues form intramolecular hydrogen bonds, which may maintain the round shape of the cyclodextrin ring; the seven glycosidic O4 atoms are coplanar within 0.11 Å. The heptagon composed of seven O4 atoms is approximately regular since the side lengths of the heptagon are in the range 4.33 (7)–4.46 (7) Å and the O—O—O angles vary from 124.8 (2) to 133.5 (2)°. The glucose residues are inclined to the perpendicular axis of the O4 atoms plane to make the hydrophobic cavity smaller at the primary hydroxyl site. The packing of the disubstituted β-CD macrocycles is unique in such as of the two residues that may be included intermoleculary into the cavity of another molecule, exclusively the phenylthio group is selected for penetrating the cavity from the wider secondary hydroxyl group side (Fig. 2), thereby providing a most interesting case of guest differentiation by a β-CD cavity. The methylbenzylthio moiety, on the other hand, is partially spread over the top of its own primary hydroxyl group side, thus capping in part the narrower opening of the β-CD macrocycle, making this supramolecular self-assembly a unique example of crystal engineering. The guest host staples surrounded by crystal water molecules run parallel to the x axis. As seen in Fig. 3 the hydrophobic cores are clearely separated from the hydrophilic surface and the crystal water molecules.