Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019640/fl6057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019640/fl6057IIIsup2.hkl |
CCDC reference: 225772
Data collection: R3M Software (Siemens, 1983); cell refinement: R3M Software; data reduction: R3M Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997); software used to prepare material for publication: SHELXL97; PLATON (Spek, 1990).
C20H28Cl2O7 | F(000) = 952 |
Mr = 451.34 | Dx = 1.341 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 14.863 (3) Å | θ = 2.8–14.5° |
b = 18.069 (4) Å | µ = 0.33 mm−1 |
c = 8.351 (3) Å | T = 153 K |
β = 94.49 (1)° | Rod, colourless |
V = 2235.9 (10) Å3 | 0.58 × 0.08 × 0.07 mm |
Z = 4 |
Siemens/Nicolet R3m 4-circle diffractometer | Rint = 0.061 |
Radiation source: fine-focus sealed tube | θmax = 24.7°, θmin = 1.8° |
Graphite monochromator | h = −17→17 |
ω scan | k = 0→21 |
4099 measured reflections | l = 0→9 |
3955 independent reflections | 3 standard reflections every 97 reflections |
2500 reflections with I > 2σ(I) | intensity decay: 10% |
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)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0835P)2] where P = Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
3955 reflections | Δρmax = 0.41 e Å−3 |
503 parameters | Δρmin = −0.40 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.07 (14) |
Experimental. Crystal decay was monitored by collection of 3 standards and scaled accordingly. A standard 0.8 mm diameter collimator was used. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.72350 (17) | 0.37896 (15) | 0.3228 (3) | 0.0381 (7) | |
Cl2 | 0.69403 (16) | 0.52727 (17) | 0.2041 (3) | 0.0381 (7) | |
Cl1' | −0.19083 (17) | 0.04666 (15) | 0.0953 (3) | 0.0348 (6) | |
Cl2' | −0.16490 (16) | 0.14624 (18) | −0.1662 (3) | 0.0377 (7) | |
O1 | 0.6720 (4) | 0.5618 (4) | 0.5348 (7) | 0.0293 (17) | |
O2 | 0.6409 (5) | 0.4416 (4) | 0.5823 (8) | 0.0374 (19) | |
O3 | 0.8512 (4) | 0.5671 (4) | 0.4422 (8) | 0.0247 (16) | |
H3O | 0.8044 | 0.5900 | 0.4079 | 0.037* | |
O4 | 0.8803 (4) | 0.4752 (4) | 0.2692 (7) | 0.0289 (16) | |
O5 | 0.8422 (4) | 0.4619 (4) | 0.6885 (8) | 0.0306 (17) | |
O6 | 1.1177 (4) | 0.4656 (4) | 0.4056 (8) | 0.0366 (19) | |
O7 | 0.9689 (5) | 0.5358 (6) | 0.0000 (9) | 0.066 (3) | |
H7O | 0.9132 | 0.5405 | 0.0084 | 0.100* | |
O1' | −0.3200 (4) | 0.2253 (4) | −0.0416 (8) | 0.0338 (18) | |
O2' | −0.3620 (4) | 0.1127 (4) | 0.0422 (9) | 0.0407 (19) | |
O3' | −0.1503 (4) | 0.2647 (4) | 0.0906 (8) | 0.0275 (16) | |
H3'O | −0.2031 | 0.2809 | 0.0926 | 0.041* | |
O4' | −0.0562 (4) | 0.1684 (4) | 0.1420 (7) | 0.0226 (15) | |
O5' | −0.2649 (4) | 0.2130 (4) | 0.3092 (7) | 0.0301 (16) | |
O6' | 0.0515 (4) | 0.2450 (4) | 0.5135 (7) | 0.0264 (16) | |
O7' | 0.1218 (4) | 0.1133 (4) | 0.2546 (7) | 0.0276 (16) | |
H7'O | 0.1004 | 0.0839 | 0.1838 | 0.041* | |
C1 | 0.6785 (6) | 0.4899 (6) | 0.5158 (12) | 0.029 (2) | |
C2 | 0.7372 (6) | 0.4729 (6) | 0.3726 (11) | 0.025 (2) | |
C3 | 0.8398 (6) | 0.4924 (6) | 0.4121 (11) | 0.025 (2) | |
C4 | 0.8837 (6) | 0.4438 (6) | 0.5472 (11) | 0.026 (2) | |
H4 | 0.8708 | 0.3908 | 0.5203 | 0.031* | |
C5 | 0.9860 (6) | 0.4553 (6) | 0.5621 (11) | 0.027 (2) | |
H5A | 1.0141 | 0.4198 | 0.6413 | 0.032* | |
H5B | 0.9999 | 0.5059 | 0.6019 | 0.032* | |
C6 | 1.0259 (6) | 0.4442 (6) | 0.4005 (12) | 0.032 (3) | |
H6 | 1.0198 | 0.3911 | 0.3675 | 0.039* | |
C7 | 0.9748 (6) | 0.4935 (6) | 0.2736 (12) | 0.032 (2) | |
H7 | 0.9839 | 0.5468 | 0.3026 | 0.038* | |
C8 | 1.0044 (7) | 0.4796 (7) | 0.1093 (11) | 0.038 (3) | |
H8A | 1.0711 | 0.4798 | 0.1131 | 0.045* | |
H8B | 0.9827 | 0.4304 | 0.0710 | 0.045* | |
C9 | 0.6165 (7) | 0.5953 (7) | 0.6560 (12) | 0.036 (3) | |
C10 | 0.6290 (9) | 0.6767 (7) | 0.6345 (14) | 0.057 (4) | |
H10A | 0.6068 | 0.6909 | 0.5252 | 0.085* | |
H10B | 0.6932 | 0.6890 | 0.6522 | 0.085* | |
H10C | 0.5951 | 0.7036 | 0.7121 | 0.085* | |
C11 | 0.5182 (6) | 0.5728 (7) | 0.6132 (12) | 0.048 (3) | |
H11A | 0.4995 | 0.5891 | 0.5037 | 0.072* | |
H11B | 0.4795 | 0.5960 | 0.6887 | 0.072* | |
H11C | 0.5127 | 0.5189 | 0.6199 | 0.072* | |
C12 | 0.6495 (7) | 0.5694 (8) | 0.8241 (11) | 0.051 (4) | |
H12A | 0.6400 | 0.5159 | 0.8328 | 0.076* | |
H12B | 0.6158 | 0.5951 | 0.9036 | 0.076* | |
H12C | 0.7140 | 0.5804 | 0.8439 | 0.076* | |
C13 | 0.8339 (8) | 0.4024 (7) | 0.7946 (13) | 0.047 (3) | |
H13A | 0.8048 | 0.4195 | 0.8893 | 0.070* | |
H13B | 0.8940 | 0.3828 | 0.8281 | 0.070* | |
H13C | 0.7972 | 0.3634 | 0.7406 | 0.070* | |
C14 | 1.1776 (6) | 0.4141 (7) | 0.4889 (13) | 0.042 (3) | |
H14A | 1.1547 | 0.3631 | 0.4704 | 0.050* | |
H14B | 1.1802 | 0.4241 | 0.6057 | 0.050* | |
C16 | 1.3390 (4) | 0.3759 (4) | 0.5026 (8) | 0.047 (3) | |
H16 | 1.3268 | 0.3443 | 0.5892 | 0.057* | |
C17 | 1.4249 (4) | 0.3776 (4) | 0.4475 (9) | 0.054 (3) | |
H17 | 1.4713 | 0.3471 | 0.4964 | 0.065* | |
C18 | 1.4427 (3) | 0.4238 (4) | 0.3207 (9) | 0.042 (3) | |
H18 | 1.5014 | 0.4249 | 0.2831 | 0.051* | |
C19 | 1.3748 (4) | 0.4684 (4) | 0.2492 (7) | 0.043 (3) | |
H19 | 1.3870 | 0.5000 | 0.1626 | 0.051* | |
C20 | 1.2890 (4) | 0.4668 (4) | 0.3043 (8) | 0.038 (3) | |
H20 | 1.2425 | 0.4972 | 0.2554 | 0.046* | |
C15 | 1.2711 (3) | 0.4205 (4) | 0.4311 (8) | 0.031 (2) | |
C1' | −0.3079 (6) | 0.1574 (7) | 0.0150 (11) | 0.028 (2) | |
C2' | −0.2044 (5) | 0.1392 (6) | 0.0306 (10) | 0.021 (2) | |
C3' | −0.1466 (5) | 0.1924 (5) | 0.1467 (11) | 0.021 (2) | |
C4' | −0.1741 (6) | 0.1854 (6) | 0.3188 (10) | 0.022 (2) | |
H4' | −0.1739 | 0.1320 | 0.3505 | 0.027* | |
C5' | −0.1091 (6) | 0.2275 (6) | 0.4320 (11) | 0.028 (2) | |
H5'A | −0.1249 | 0.2196 | 0.5437 | 0.033* | |
H5'B | −0.1144 | 0.2810 | 0.4081 | 0.033* | |
C6' | −0.0112 (5) | 0.2024 (6) | 0.4167 (11) | 0.025 (2) | |
H6' | −0.0048 | 0.1490 | 0.4470 | 0.030* | |
C7' | 0.0085 (5) | 0.2124 (5) | 0.2415 (10) | 0.023 (2) | |
H7' | 0.0009 | 0.2658 | 0.2117 | 0.027* | |
C8' | 0.1013 (6) | 0.1874 (5) | 0.2057 (11) | 0.024 (2) | |
H8'A | 0.1069 | 0.1916 | 0.0887 | 0.029* | |
H8'B | 0.1464 | 0.2211 | 0.2606 | 0.029* | |
C9' | −0.4149 (6) | 0.2548 (7) | −0.0747 (12) | 0.039 (3) | |
C10' | −0.4011 (8) | 0.3293 (8) | −0.1374 (18) | 0.074 (5) | |
H10D | −0.3691 | 0.3596 | −0.0540 | 0.111* | |
H10E | −0.4597 | 0.3518 | −0.1696 | 0.111* | |
H10F | −0.3652 | 0.3262 | −0.2308 | 0.111* | |
C11' | −0.4629 (7) | 0.2087 (9) | −0.2004 (13) | 0.070 (5) | |
H11D | −0.4718 | 0.1588 | −0.1580 | 0.106* | |
H11E | −0.4270 | 0.2056 | −0.2937 | 0.106* | |
H11F | −0.5217 | 0.2309 | −0.2326 | 0.106* | |
C12' | −0.4612 (6) | 0.2547 (7) | 0.0804 (12) | 0.041 (3) | |
H12D | −0.4686 | 0.2036 | 0.1164 | 0.062* | |
H12E | −0.5206 | 0.2782 | 0.0626 | 0.062* | |
H12F | −0.4244 | 0.2822 | 0.1627 | 0.062* | |
C13' | −0.3111 (6) | 0.1921 (9) | 0.4497 (12) | 0.055 (4) | |
H13D | −0.3728 | 0.2116 | 0.4394 | 0.083* | |
H13E | −0.2786 | 0.2126 | 0.5463 | 0.083* | |
H13F | −0.3129 | 0.1380 | 0.4579 | 0.083* | |
C14' | 0.0442 (7) | 0.2313 (7) | 0.6802 (10) | 0.034 (3) | |
H14C | 0.0388 | 0.1773 | 0.6981 | 0.040* | |
H14D | −0.0111 | 0.2552 | 0.7141 | 0.040* | |
C16' | 0.1166 (4) | 0.3213 (4) | 0.8791 (8) | 0.032 (3) | |
H16' | 0.0607 | 0.3468 | 0.8792 | 0.039* | |
C17' | 0.1904 (5) | 0.3449 (3) | 0.9785 (8) | 0.040 (3) | |
H17' | 0.1850 | 0.3865 | 1.0466 | 0.049* | |
C18' | 0.2722 (4) | 0.3075 (4) | 0.9784 (8) | 0.043 (3) | |
H18' | 0.3226 | 0.3236 | 1.0464 | 0.052* | |
C19' | 0.2801 (3) | 0.2466 (4) | 0.8789 (9) | 0.054 (4) | |
H19' | 0.3360 | 0.2210 | 0.8788 | 0.065* | |
C20' | 0.2063 (4) | 0.2230 (3) | 0.7795 (8) | 0.038 (3) | |
H20' | 0.2117 | 0.1814 | 0.7115 | 0.046* | |
C15' | 0.1245 (4) | 0.2604 (4) | 0.7796 (7) | 0.028 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0289 (13) | 0.0337 (16) | 0.0507 (17) | −0.0057 (13) | −0.0020 (12) | −0.0122 (14) |
Cl2 | 0.0348 (13) | 0.0546 (19) | 0.0237 (12) | 0.0054 (14) | −0.0061 (10) | 0.0035 (13) |
Cl1' | 0.0348 (14) | 0.0327 (16) | 0.0373 (15) | −0.0017 (12) | 0.0049 (11) | −0.0069 (13) |
Cl2' | 0.0308 (13) | 0.064 (2) | 0.0194 (12) | −0.0019 (14) | 0.0080 (10) | −0.0025 (13) |
O1 | 0.035 (4) | 0.031 (5) | 0.022 (4) | 0.009 (3) | 0.006 (3) | −0.005 (3) |
O2 | 0.043 (4) | 0.041 (5) | 0.029 (4) | −0.001 (4) | 0.012 (3) | 0.005 (4) |
O3 | 0.020 (3) | 0.028 (4) | 0.026 (4) | 0.009 (3) | 0.001 (3) | 0.001 (3) |
O4 | 0.024 (3) | 0.034 (4) | 0.029 (4) | −0.006 (3) | 0.005 (3) | −0.004 (3) |
O5 | 0.023 (3) | 0.036 (4) | 0.033 (4) | −0.001 (3) | 0.004 (3) | 0.007 (4) |
O6 | 0.023 (4) | 0.043 (5) | 0.045 (4) | 0.004 (3) | 0.005 (3) | 0.015 (4) |
O7 | 0.069 (6) | 0.092 (8) | 0.036 (4) | 0.010 (6) | −0.008 (4) | 0.016 (6) |
O1' | 0.022 (3) | 0.046 (5) | 0.033 (4) | −0.002 (3) | 0.002 (3) | 0.014 (4) |
O2' | 0.020 (4) | 0.043 (5) | 0.059 (5) | −0.008 (4) | 0.002 (3) | −0.002 (4) |
O3' | 0.012 (3) | 0.033 (4) | 0.037 (4) | 0.003 (3) | −0.001 (3) | 0.005 (3) |
O4' | 0.017 (3) | 0.030 (4) | 0.020 (3) | 0.000 (3) | −0.002 (2) | −0.003 (3) |
O5' | 0.024 (3) | 0.041 (4) | 0.026 (4) | 0.002 (3) | 0.007 (3) | −0.003 (3) |
O6' | 0.019 (3) | 0.036 (4) | 0.024 (3) | −0.008 (3) | −0.002 (3) | 0.003 (3) |
O7' | 0.024 (3) | 0.032 (4) | 0.027 (4) | 0.006 (3) | 0.006 (3) | −0.002 (3) |
C1 | 0.024 (5) | 0.036 (7) | 0.027 (6) | 0.016 (5) | 0.000 (4) | 0.000 (5) |
C2 | 0.022 (5) | 0.029 (6) | 0.024 (5) | 0.011 (4) | −0.003 (4) | −0.001 (5) |
C3 | 0.024 (5) | 0.027 (6) | 0.024 (5) | 0.002 (4) | 0.003 (4) | −0.010 (5) |
C4 | 0.023 (5) | 0.030 (6) | 0.024 (5) | 0.007 (5) | 0.005 (4) | 0.000 (5) |
C5 | 0.019 (5) | 0.038 (6) | 0.024 (5) | −0.001 (5) | 0.002 (4) | 0.003 (5) |
C6 | 0.026 (5) | 0.034 (7) | 0.038 (6) | 0.003 (5) | 0.009 (4) | 0.004 (5) |
C7 | 0.026 (5) | 0.033 (6) | 0.037 (6) | 0.007 (5) | 0.009 (4) | 0.003 (5) |
C8 | 0.037 (6) | 0.042 (7) | 0.034 (6) | −0.002 (5) | 0.008 (5) | −0.002 (6) |
C9 | 0.035 (6) | 0.053 (8) | 0.021 (5) | 0.004 (6) | 0.009 (4) | 0.001 (5) |
C10 | 0.074 (9) | 0.062 (10) | 0.037 (7) | 0.004 (8) | 0.017 (6) | −0.018 (7) |
C11 | 0.033 (6) | 0.069 (10) | 0.042 (7) | 0.015 (6) | −0.003 (5) | −0.022 (6) |
C12 | 0.042 (6) | 0.090 (11) | 0.020 (5) | 0.018 (7) | 0.003 (5) | 0.006 (6) |
C13 | 0.048 (7) | 0.055 (9) | 0.039 (7) | −0.010 (6) | 0.016 (5) | 0.015 (6) |
C14 | 0.025 (5) | 0.054 (8) | 0.044 (7) | 0.009 (6) | −0.007 (5) | 0.016 (6) |
C16 | 0.029 (6) | 0.051 (8) | 0.060 (8) | 0.008 (6) | −0.006 (5) | 0.020 (7) |
C17 | 0.038 (6) | 0.054 (8) | 0.070 (9) | 0.013 (7) | 0.002 (6) | 0.023 (8) |
C18 | 0.030 (6) | 0.041 (7) | 0.056 (8) | 0.004 (6) | 0.003 (5) | −0.003 (6) |
C19 | 0.039 (6) | 0.054 (8) | 0.036 (6) | 0.001 (6) | 0.007 (5) | 0.011 (6) |
C20 | 0.027 (5) | 0.041 (7) | 0.046 (7) | 0.005 (5) | 0.004 (5) | −0.002 (6) |
C15 | 0.027 (5) | 0.039 (7) | 0.027 (5) | −0.007 (5) | −0.004 (4) | 0.002 (5) |
C1' | 0.018 (5) | 0.047 (7) | 0.018 (5) | −0.004 (5) | −0.004 (4) | −0.006 (5) |
C2' | 0.015 (4) | 0.030 (6) | 0.018 (4) | 0.008 (4) | −0.001 (3) | 0.004 (4) |
C3' | 0.013 (4) | 0.022 (5) | 0.027 (5) | 0.002 (4) | 0.000 (4) | −0.010 (4) |
C4' | 0.023 (5) | 0.027 (6) | 0.017 (5) | 0.001 (4) | 0.002 (4) | −0.006 (4) |
C5' | 0.026 (5) | 0.039 (7) | 0.019 (5) | −0.003 (5) | 0.004 (4) | −0.012 (5) |
C6' | 0.010 (4) | 0.029 (6) | 0.036 (6) | −0.005 (4) | −0.001 (4) | −0.004 (5) |
C7' | 0.020 (5) | 0.019 (5) | 0.027 (5) | −0.002 (4) | −0.001 (4) | 0.004 (4) |
C8' | 0.015 (4) | 0.028 (6) | 0.030 (5) | 0.004 (4) | 0.001 (4) | 0.003 (5) |
C9' | 0.024 (5) | 0.067 (9) | 0.024 (6) | 0.015 (6) | −0.007 (4) | 0.012 (6) |
C10' | 0.042 (7) | 0.070 (10) | 0.110 (12) | 0.018 (7) | 0.010 (7) | 0.071 (10) |
C11' | 0.034 (6) | 0.142 (15) | 0.034 (7) | 0.030 (9) | −0.003 (5) | 0.003 (9) |
C12' | 0.026 (5) | 0.058 (8) | 0.041 (6) | 0.009 (6) | 0.006 (5) | −0.002 (6) |
C13' | 0.012 (5) | 0.120 (13) | 0.035 (6) | −0.014 (6) | 0.010 (4) | 0.010 (7) |
C14' | 0.037 (6) | 0.045 (7) | 0.020 (5) | −0.011 (5) | 0.005 (4) | −0.008 (5) |
C16' | 0.023 (5) | 0.034 (6) | 0.037 (6) | 0.010 (5) | −0.013 (4) | −0.001 (5) |
C17' | 0.061 (8) | 0.025 (6) | 0.033 (6) | −0.003 (6) | −0.011 (5) | −0.004 (5) |
C18' | 0.029 (6) | 0.054 (8) | 0.043 (7) | 0.005 (6) | −0.015 (5) | −0.012 (6) |
C19' | 0.028 (6) | 0.069 (10) | 0.065 (8) | −0.005 (6) | 0.000 (6) | −0.005 (8) |
C20' | 0.040 (6) | 0.040 (7) | 0.034 (6) | 0.010 (6) | 0.002 (5) | −0.009 (6) |
C15' | 0.034 (5) | 0.020 (6) | 0.026 (5) | −0.001 (5) | −0.015 (4) | 0.003 (4) |
Cl1—C2 | 1.756 (11) | C13—H13C | 0.9800 |
Cl2—C2 | 1.792 (9) | C14—C15 | 1.510 (11) |
Cl1'—C2' | 1.764 (10) | C14—H14A | 0.9900 |
Cl2'—C2' | 1.793 (8) | C14—H14B | 0.9900 |
O1—C1 | 1.313 (12) | C16—C17 | 1.3900 |
O1—C9 | 1.485 (11) | C16—C15 | 1.3900 |
O2—C1 | 1.197 (12) | C16—H16 | 0.9500 |
O3—C3 | 1.382 (11) | C17—C18 | 1.3900 |
O3—H3O | 0.8400 | C17—H17 | 0.9500 |
O4—C3 | 1.411 (11) | C18—C19 | 1.3900 |
O4—C7 | 1.441 (11) | C18—H18 | 0.9500 |
O5—C13 | 1.405 (12) | C19—C20 | 1.3900 |
O5—C4 | 1.412 (11) | C19—H19 | 0.9500 |
O6—C6 | 1.415 (11) | C20—C15 | 1.3900 |
O6—C14 | 1.430 (12) | C20—H20 | 0.9500 |
O7—C8 | 1.437 (13) | C1'—C2' | 1.569 (12) |
O7—H7O | 0.8400 | C2'—C3' | 1.572 (12) |
O1'—C1' | 1.322 (13) | C3'—C4' | 1.530 (12) |
O1'—C9' | 1.514 (11) | C4'—C5' | 1.504 (12) |
O2'—C1' | 1.175 (12) | C4'—H4' | 1.0000 |
O3'—C3' | 1.387 (11) | C5'—C6' | 1.539 (12) |
O3'—H3'O | 0.8400 | C5'—H5'A | 0.9900 |
O4'—C3' | 1.416 (10) | C5'—H5'B | 0.9900 |
O4'—C7' | 1.458 (10) | C6'—C7' | 1.525 (12) |
O5'—C4' | 1.436 (10) | C6'—H6' | 1.0000 |
O5'—C13' | 1.455 (11) | C7'—C8' | 1.504 (12) |
O6'—C6' | 1.414 (10) | C7'—H7' | 1.0000 |
O6'—C14' | 1.427 (10) | C8'—H8'A | 0.9900 |
O7'—C8' | 1.426 (11) | C8'—H8'B | 0.9900 |
O7'—H7'O | 0.8400 | C9'—C10' | 1.464 (16) |
C1—C2 | 1.565 (13) | C9'—C11' | 1.479 (17) |
C2—C3 | 1.575 (12) | C9'—C12' | 1.514 (13) |
C3—C4 | 1.533 (13) | C10'—H10D | 0.9800 |
C4—C5 | 1.529 (12) | C10'—H10E | 0.9800 |
C4—H4 | 1.0000 | C10'—H10F | 0.9800 |
C5—C6 | 1.530 (12) | C11'—H11D | 0.9800 |
C5—H5A | 0.9900 | C11'—H11E | 0.9800 |
C5—H5B | 0.9900 | C11'—H11F | 0.9800 |
C6—C7 | 1.539 (14) | C12'—H12D | 0.9800 |
C6—H6 | 1.0000 | C12'—H12E | 0.9800 |
C7—C8 | 1.494 (13) | C12'—H12F | 0.9800 |
C7—H7 | 1.0000 | C13'—H13D | 0.9800 |
C8—H8A | 0.9900 | C13'—H13E | 0.9800 |
C8—H8B | 0.9900 | C13'—H13F | 0.9800 |
C9—C10 | 1.495 (17) | C14'—C15' | 1.496 (10) |
C9—C12 | 1.524 (14) | C14'—H14C | 0.9900 |
C9—C11 | 1.531 (14) | C14'—H14D | 0.9900 |
C10—H10A | 0.9800 | C16'—C17' | 1.3900 |
C10—H10B | 0.9800 | C16'—C15' | 1.3900 |
C10—H10C | 0.9800 | C16'—H16' | 0.9500 |
C11—H11A | 0.9800 | C17'—C18' | 1.3900 |
C11—H11B | 0.9800 | C17'—H17' | 0.9500 |
C11—H11C | 0.9800 | C18'—C19' | 1.3900 |
C12—H12A | 0.9800 | C18'—H18' | 0.9500 |
C12—H12B | 0.9800 | C19'—C20' | 1.3900 |
C12—H12C | 0.9800 | C19'—H19' | 0.9500 |
C13—H13A | 0.9800 | C20'—C15' | 1.3900 |
C13—H13B | 0.9800 | C20'—H20' | 0.9500 |
C1—O1—C9 | 122.4 (8) | C15—C20—C19 | 120.0 |
C3—O3—H3O | 109.5 | C15—C20—H20 | 120.0 |
C3—O4—C7 | 114.0 (7) | C19—C20—H20 | 120.0 |
C13—O5—C4 | 114.6 (8) | C20—C15—C16 | 120.0 |
C6—O6—C14 | 113.6 (8) | C20—C15—C14 | 121.7 (6) |
C8—O7—H7O | 109.5 | C16—C15—C14 | 118.3 (6) |
C1'—O1'—C9' | 119.4 (8) | O2'—C1'—O1' | 129.2 (9) |
C3'—O3'—H3'O | 109.5 | O2'—C1'—C2' | 121.4 (10) |
C3'—O4'—C7' | 113.7 (6) | O1'—C1'—C2' | 109.2 (8) |
C4'—O5'—C13' | 111.4 (7) | C1'—C2'—C3' | 114.0 (7) |
C6'—O6'—C14' | 111.4 (7) | C1'—C2'—Cl1' | 108.2 (7) |
C8'—O7'—H7'O | 109.5 | C3'—C2'—Cl1' | 110.3 (6) |
O2—C1—O1 | 128.7 (10) | C1'—C2'—Cl2' | 107.3 (6) |
O2—C1—C2 | 121.3 (10) | C3'—C2'—Cl2' | 108.7 (6) |
O1—C1—C2 | 109.7 (9) | Cl1'—C2'—Cl2' | 108.1 (5) |
C1—C2—C3 | 112.6 (7) | O3'—C3'—O4' | 106.9 (7) |
C1—C2—Cl1 | 108.0 (7) | O3'—C3'—C4' | 112.9 (7) |
C3—C2—Cl1 | 110.9 (6) | O4'—C3'—C4' | 108.9 (7) |
C1—C2—Cl2 | 107.8 (6) | O3'—C3'—C2' | 111.3 (7) |
C3—C2—Cl2 | 108.9 (7) | O4'—C3'—C2' | 105.6 (7) |
Cl1—C2—Cl2 | 108.4 (5) | C4'—C3'—C2' | 110.8 (7) |
O3—C3—O4 | 108.3 (8) | O5'—C4'—C5' | 114.4 (8) |
O3—C3—C4 | 112.7 (8) | O5'—C4'—C3' | 103.7 (7) |
O4—C3—C4 | 108.2 (8) | C5'—C4'—C3' | 110.0 (7) |
O3—C3—C2 | 111.0 (8) | O5'—C4'—H4' | 109.5 |
O4—C3—C2 | 104.1 (7) | C5'—C4'—H4' | 109.5 |
C4—C3—C2 | 112.1 (8) | C3'—C4'—H4' | 109.5 |
O5—C4—C5 | 113.4 (7) | C4'—C5'—C6' | 111.3 (8) |
O5—C4—C3 | 107.1 (7) | C4'—C5'—H5'A | 109.4 |
C5—C4—C3 | 110.2 (8) | C6'—C5'—H5'A | 109.4 |
O5—C4—H4 | 108.7 | C4'—C5'—H5'B | 109.4 |
C5—C4—H4 | 108.7 | C6'—C5'—H5'B | 109.4 |
C3—C4—H4 | 108.7 | H5'A—C5'—H5'B | 108.0 |
C4—C5—C6 | 111.2 (7) | O6'—C6'—C7' | 108.4 (7) |
C4—C5—H5A | 109.4 | O6'—C6'—C5' | 112.2 (8) |
C6—C5—H5A | 109.4 | C7'—C6'—C5' | 107.4 (7) |
C4—C5—H5B | 109.4 | O6'—C6'—H6' | 109.6 |
C6—C5—H5B | 109.4 | C7'—C6'—H6' | 109.6 |
H5A—C5—H5B | 108.0 | C5'—C6'—H6' | 109.6 |
O6—C6—C5 | 112.2 (8) | O4'—C7'—C8' | 107.3 (7) |
O6—C6—C7 | 106.6 (8) | O4'—C7'—C6' | 108.3 (7) |
C5—C6—C7 | 109.1 (8) | C8'—C7'—C6' | 113.8 (7) |
O6—C6—H6 | 109.6 | O4'—C7'—H7' | 109.1 |
C5—C6—H6 | 109.6 | C8'—C7'—H7' | 109.1 |
C7—C6—H6 | 109.6 | C6'—C7'—H7' | 109.1 |
O4—C7—C8 | 107.1 (8) | O7'—C8'—C7' | 113.8 (8) |
O4—C7—C6 | 108.2 (8) | O7'—C8'—H8'A | 108.8 |
C8—C7—C6 | 111.7 (9) | C7'—C8'—H8'A | 108.8 |
O4—C7—H7 | 109.9 | O7'—C8'—H8'B | 108.8 |
C8—C7—H7 | 109.9 | C7'—C8'—H8'B | 108.8 |
C6—C7—H7 | 109.9 | H8'A—C8'—H8'B | 107.7 |
O7—C8—C7 | 110.2 (9) | C10'—C9'—C11' | 109.8 (11) |
O7—C8—H8A | 109.6 | C10'—C9'—C12' | 113.2 (11) |
C7—C8—H8A | 109.6 | C11'—C9'—C12' | 112.3 (10) |
O7—C8—H8B | 109.6 | C10'—C9'—O1' | 103.5 (9) |
C7—C8—H8B | 109.6 | C11'—C9'—O1' | 108.8 (9) |
H8A—C8—H8B | 108.1 | C12'—C9'—O1' | 108.8 (7) |
O1—C9—C10 | 103.8 (8) | C9'—C10'—H10D | 109.5 |
O1—C9—C12 | 110.3 (8) | C9'—C10'—H10E | 109.5 |
C10—C9—C12 | 112.3 (10) | H10D—C10'—H10E | 109.5 |
O1—C9—C11 | 107.7 (8) | C9'—C10'—H10F | 109.5 |
C10—C9—C11 | 111.0 (10) | H10D—C10'—H10F | 109.5 |
C12—C9—C11 | 111.5 (9) | H10E—C10'—H10F | 109.5 |
C9—C10—H10A | 109.5 | C9'—C11'—H11D | 109.5 |
C9—C10—H10B | 109.5 | C9'—C11'—H11E | 109.5 |
H10A—C10—H10B | 109.5 | H11D—C11'—H11E | 109.5 |
C9—C10—H10C | 109.5 | C9'—C11'—H11F | 109.5 |
H10A—C10—H10C | 109.5 | H11D—C11'—H11F | 109.5 |
H10B—C10—H10C | 109.5 | H11E—C11'—H11F | 109.5 |
C9—C11—H11A | 109.5 | C9'—C12'—H12D | 109.5 |
C9—C11—H11B | 109.5 | C9'—C12'—H12E | 109.5 |
H11A—C11—H11B | 109.5 | H12D—C12'—H12E | 109.5 |
C9—C11—H11C | 109.5 | C9'—C12'—H12F | 109.5 |
H11A—C11—H11C | 109.5 | H12D—C12'—H12F | 109.5 |
H11B—C11—H11C | 109.5 | H12E—C12'—H12F | 109.5 |
C9—C12—H12A | 109.5 | O5'—C13'—H13D | 109.5 |
C9—C12—H12B | 109.5 | O5'—C13'—H13E | 109.5 |
H12A—C12—H12B | 109.5 | H13D—C13'—H13E | 109.5 |
C9—C12—H12C | 109.5 | O5'—C13'—H13F | 109.5 |
H12A—C12—H12C | 109.5 | H13D—C13'—H13F | 109.5 |
H12B—C12—H12C | 109.5 | H13E—C13'—H13F | 109.5 |
O5—C13—H13A | 109.5 | O6'—C14'—C15' | 111.2 (7) |
O5—C13—H13B | 109.5 | O6'—C14'—H14C | 109.4 |
H13A—C13—H13B | 109.5 | C15'—C14'—H14C | 109.4 |
O5—C13—H13C | 109.5 | O6'—C14'—H14D | 109.4 |
H13A—C13—H13C | 109.5 | C15'—C14'—H14D | 109.4 |
H13B—C13—H13C | 109.5 | H14C—C14'—H14D | 108.0 |
O6—C14—C15 | 110.4 (8) | C17'—C16'—C15' | 120.0 |
O6—C14—H14A | 109.6 | C17'—C16'—H16' | 120.0 |
C15—C14—H14A | 109.6 | C15'—C16'—H16' | 120.0 |
O6—C14—H14B | 109.6 | C18'—C17'—C16' | 120.0 |
C15—C14—H14B | 109.6 | C18'—C17'—H17' | 120.0 |
H14A—C14—H14B | 108.1 | C16'—C17'—H17' | 120.0 |
C17—C16—C15 | 120.0 | C17'—C18'—C19' | 120.0 |
C17—C16—H16 | 120.0 | C17'—C18'—H18' | 120.0 |
C15—C16—H16 | 120.0 | C19'—C18'—H18' | 120.0 |
C18—C17—C16 | 120.0 | C18'—C19'—C20' | 120.0 |
C18—C17—H17 | 120.0 | C18'—C19'—H19' | 120.0 |
C16—C17—H17 | 120.0 | C20'—C19'—H19' | 120.0 |
C17—C18—C19 | 120.0 | C15'—C20'—C19' | 120.0 |
C17—C18—H18 | 120.0 | C15'—C20'—H20' | 120.0 |
C19—C18—H18 | 120.0 | C19'—C20'—H20' | 120.0 |
C20—C19—C18 | 120.0 | C20'—C15'—C16' | 120.0 |
C20—C19—H19 | 120.0 | C20'—C15'—C14' | 119.3 (6) |
C18—C19—H19 | 120.0 | C16'—C15'—C14' | 120.6 (6) |
C9—O1—C1—O2 | 3.3 (16) | C9'—O1'—C1'—O2' | 2.1 (15) |
C9—O1—C1—C2 | 176.7 (7) | C9'—O1'—C1'—C2' | 177.3 (7) |
O2—C1—C2—C3 | −116.0 (11) | O2'—C1'—C2'—C3' | −124.2 (10) |
O1—C1—C2—C3 | 70.0 (10) | O1'—C1'—C2'—C3' | 60.2 (10) |
O2—C1—C2—Cl1 | 6.9 (11) | O2'—C1'—C2'—Cl1' | −1.1 (11) |
O1—C1—C2—Cl1 | −167.1 (7) | O1'—C1'—C2'—Cl1' | −176.7 (6) |
O2—C1—C2—Cl2 | 123.9 (9) | O2'—C1'—C2'—Cl2' | 115.3 (9) |
O1—C1—C2—Cl2 | −50.1 (9) | O1'—C1'—C2'—Cl2' | −60.3 (9) |
C7—O4—C3—O3 | 57.8 (10) | C7'—O4'—C3'—O3' | 60.5 (9) |
C7—O4—C3—C4 | −64.6 (10) | C7'—O4'—C3'—C4' | −61.9 (9) |
C7—O4—C3—C2 | 176.0 (8) | C7'—O4'—C3'—C2' | 179.0 (7) |
C1—C2—C3—O3 | −62.2 (11) | C1'—C2'—C3'—O3' | −63.1 (10) |
Cl1—C2—C3—O3 | 176.5 (6) | Cl1'—C2'—C3'—O3' | 174.9 (6) |
Cl2—C2—C3—O3 | 57.3 (9) | Cl2'—C2'—C3'—O3' | 56.6 (8) |
C1—C2—C3—O4 | −178.6 (8) | C1'—C2'—C3'—O4' | −178.7 (7) |
Cl1—C2—C3—O4 | 60.2 (8) | Cl1'—C2'—C3'—O4' | 59.3 (8) |
Cl2—C2—C3—O4 | −59.1 (8) | Cl2'—C2'—C3'—O4' | −59.1 (8) |
C1—C2—C3—C4 | 64.8 (10) | C1'—C2'—C3'—C4' | 63.5 (10) |
Cl1—C2—C3—C4 | −56.4 (9) | Cl1'—C2'—C3'—C4' | −58.5 (8) |
Cl2—C2—C3—C4 | −175.7 (7) | Cl2'—C2'—C3'—C4' | −176.8 (6) |
C13—O5—C4—C5 | −91.5 (10) | C13'—O5'—C4'—C5' | −75.9 (11) |
C13—O5—C4—C3 | 146.7 (8) | C13'—O5'—C4'—C3' | 164.2 (8) |
O3—C3—C4—O5 | 60.3 (10) | O3'—C3'—C4'—O5' | 59.8 (9) |
O4—C3—C4—O5 | −179.9 (7) | O4'—C3'—C4'—O5' | 178.4 (7) |
C2—C3—C4—O5 | −65.8 (10) | C2'—C3'—C4'—O5' | −65.8 (9) |
O3—C3—C4—C5 | −63.5 (10) | O3'—C3'—C4'—C5' | −63.1 (10) |
O4—C3—C4—C5 | 56.3 (10) | O4'—C3'—C4'—C5' | 55.6 (10) |
C2—C3—C4—C5 | 170.4 (8) | C2'—C3'—C4'—C5' | 171.3 (8) |
O5—C4—C5—C6 | −173.0 (9) | O5'—C4'—C5'—C6' | −171.3 (8) |
C3—C4—C5—C6 | −52.9 (11) | C3'—C4'—C5'—C6' | −55.0 (11) |
C14—O6—C6—C5 | 74.6 (11) | C14'—O6'—C6'—C7' | −172.9 (8) |
C14—O6—C6—C7 | −166.0 (9) | C14'—O6'—C6'—C5' | 68.7 (10) |
C4—C5—C6—O6 | 170.8 (8) | C4'—C5'—C6'—O6' | 175.7 (8) |
C4—C5—C6—C7 | 53.0 (12) | C4'—C5'—C6'—C7' | 56.6 (11) |
C3—O4—C7—C8 | −174.1 (9) | C3'—O4'—C7'—C8' | −172.0 (7) |
C3—O4—C7—C6 | 65.3 (10) | C3'—O4'—C7'—C6' | 64.7 (9) |
O6—C6—C7—O4 | −177.9 (8) | O6'—C6'—C7'—O4' | 180.0 (7) |
C5—C6—C7—O4 | −56.6 (11) | C5'—C6'—C7'—O4' | −58.6 (10) |
O6—C6—C7—C8 | 64.4 (11) | O6'—C6'—C7'—C8' | 60.7 (11) |
C5—C6—C7—C8 | −174.2 (9) | C5'—C6'—C7'—C8' | −177.9 (8) |
O4—C7—C8—O7 | 72.9 (11) | O4'—C7'—C8'—O7' | −66.2 (9) |
C6—C7—C8—O7 | −168.8 (8) | C6'—C7'—C8'—O7' | 53.7 (11) |
C1—O1—C9—C10 | −179.9 (9) | C1'—O1'—C9'—C10' | −179.0 (10) |
C1—O1—C9—C12 | 59.7 (12) | C1'—O1'—C9'—C11' | −62.3 (11) |
C1—O1—C9—C11 | −62.1 (12) | C1'—O1'—C9'—C12' | 60.3 (12) |
C6—O6—C14—C15 | 155.3 (8) | C6'—O6'—C14'—C15' | 165.3 (8) |
C15—C16—C17—C18 | 0.0 | C15'—C16'—C17'—C18' | 0.0 |
C16—C17—C18—C19 | 0.0 | C16'—C17'—C18'—C19' | 0.0 |
C17—C18—C19—C20 | 0.0 | C17'—C18'—C19'—C20' | 0.0 |
C18—C19—C20—C15 | 0.0 | C18'—C19'—C20'—C15' | 0.0 |
C19—C20—C15—C16 | 0.0 | C19'—C20'—C15'—C16' | 0.0 |
C19—C20—C15—C14 | −176.7 (8) | C19'—C20'—C15'—C14' | −176.0 (7) |
C17—C16—C15—C20 | 0.0 | C17'—C16'—C15'—C20' | 0.0 |
C17—C16—C15—C14 | 176.9 (8) | C17'—C16'—C15'—C14' | 175.9 (7) |
O6—C14—C15—C20 | −5.0 (12) | O6'—C14'—C15'—C20' | −73.8 (10) |
O6—C14—C15—C16 | 178.2 (7) | O6'—C14'—C15'—C16' | 110.3 (8) |