Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020094/rn6020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020094/rn6020Isup2.hkl |
CCDC reference: 251752
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C26H33Cl3O6 | Dx = 1.406 Mg m−3 |
Mr = 547.87 | Melting point: 183 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5719 reflections |
a = 12.1542 (10) Å | θ = 2.6–28.2° |
b = 13.8359 (10) Å | µ = 0.39 mm−1 |
c = 15.3928 (12) Å | T = 218 K |
V = 2588.5 (3) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.25 × 0.15 mm |
F(000) = 1152 |
Bruker SMART CCD area-detector diffractometer | 6052 independent reflections |
Radiation source: fine-focus sealed tube | 5607 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 28.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Shekdrick, 1996) | h = −15→15 |
Tmin = 0.858, Tmax = 0.943 | k = −18→18 |
19067 measured reflections | l = −19→18 |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.3879P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6052 reflections | Δρmax = 0.42 e Å−3 |
334 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2552 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (4) |
Experimental. Spectroscopy analysis, IR absorptions were at 3300, 3100, 3000–2880 1700 and 1650 cm-1 corresponding to alcoholics, aromatics, alkanes and carbonyls groups respectively. 1 HNMR (400 MHz, CD3OD, δ in p.p.m. relative to TMS): 12.3 s (OH-3), 10.27 s(OH-4), 7.3 s (H-9), 4.69 s(OH-6), 4.58 dd (J=12.0, 4.0 Hz) (H-3), 3.74 dd (J=12.0, 4.0 Hz) (H-3'), 2.73 dd (J= 14.4, 12.0 Hz) (H-4a), 2.52 dd (J= 14.4, 4.0 Hz) (H-4 b), 1.63 dd (J= 16.8, 1.6 Hz) (H-7'a), 2.64 dd (J=16.7, 7.2 Hz) (H-7'b), 1.76–1.80 m (H-4'a), 1.87 m (H-4'b), 1.54 m (H-5'a), 1.73 m (H-5'b), 1.6 br dd (J=7.2, 1.6 Hz) (H-1'), 2.16 s (Me- 13), 1.4 s (Me- 12), 1.3 s (Me- 11), 1.14 s (Me- 15), 0.65 s (Me- 14), 0.37 s (Me- 16). 13CNMR (100 MHz, CD3OD, δ in p.p.m. relative to TMS): 193.7 (C-10), 192.3 (C-5), 164.3 (C-8), 163.9 (C-6), 132.5 (C-9a), 120.3 (C-7), 108.6 (C-5a), 108.5 (C-9), 85.1 (C-10a), 82.5 (C-4a), 81.8 (C-2), 72.6 (C-3'), 71.0 (C-6'), 59.7 (C-3), 51.0 (C-1'), 43.4 (C-4), 42.7 (C-5'), 41.7 (C-2'), 38.3 (C-7'), 31.8 (C-4'), 29.5 (C-12), 29.3 (C-14), 25.6 (C-16), 23.2 (C-11), 16.7 (C-15), 8.8 (C-13). |
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 | 0.14600 (5) | 0.21426 (6) | 0.48685 (4) | 0.05800 (19) | |
Cl2 | 0.17171 (4) | 0.30979 (3) | 0.77452 (3) | 0.03287 (11) | |
Cl3 | −0.10033 (8) | −0.05122 (6) | 1.13374 (4) | 0.0712 (2) | |
O1 | −0.00098 (10) | 0.15177 (9) | 0.71287 (8) | 0.0253 (3) | |
O2 | 0.35809 (11) | 0.20335 (10) | 0.82923 (10) | 0.0350 (3) | |
O3 | 0.49673 (12) | 0.05919 (11) | 0.84047 (11) | 0.0378 (3) | |
H3 | 0.471 (3) | 0.110 (2) | 0.851 (2) | 0.060 (9)* | |
O4 | 0.37182 (13) | −0.24529 (10) | 0.75408 (11) | 0.0366 (3) | |
H4 | 0.315 (3) | −0.273 (2) | 0.7373 (19) | 0.054 (8)* | |
O5 | 0.03257 (10) | −0.03869 (10) | 0.75415 (10) | 0.0329 (3) | |
O6 | −0.18840 (12) | 0.16631 (12) | 0.80817 (10) | 0.0381 (3) | |
H6 | −0.140 (2) | 0.1617 (16) | 0.7774 (16) | 0.030 (6)* | |
C2 | 0.01287 (16) | 0.15051 (14) | 0.61839 (12) | 0.0302 (4) | |
C3 | 0.11369 (17) | 0.21335 (16) | 0.59995 (13) | 0.0343 (4) | |
H3A | 0.0965 | 0.2804 | 0.6179 | 0.041* | |
C4 | 0.21449 (15) | 0.18037 (15) | 0.64991 (12) | 0.0298 (4) | |
H4A | 0.2771 | 0.2221 | 0.6358 | 0.036* | |
H4B | 0.2333 | 0.1140 | 0.6333 | 0.036* | |
C5 | 0.29212 (15) | 0.14748 (13) | 0.79701 (12) | 0.0256 (4) | |
C6 | 0.41301 (15) | 0.00402 (14) | 0.81283 (12) | 0.0269 (4) | |
C7 | 0.43410 (15) | −0.09386 (14) | 0.79956 (12) | 0.0283 (4) | |
C8 | 0.34889 (15) | −0.15242 (13) | 0.77080 (12) | 0.0271 (4) | |
C9 | 0.24211 (15) | −0.11614 (13) | 0.76005 (12) | 0.0264 (4) | |
H9 | 0.1840 | −0.1578 | 0.7451 | 0.032* | |
C10 | 0.10886 (14) | 0.01588 (12) | 0.76276 (12) | 0.0243 (3) | |
C11 | 0.02153 (19) | 0.04867 (17) | 0.58136 (14) | 0.0404 (5) | |
H11A | 0.0940 | 0.0227 | 0.5935 | 0.061* | |
H11B | 0.0100 | 0.0507 | 0.5190 | 0.061* | |
H11C | −0.0339 | 0.0078 | 0.6079 | 0.061* | |
C12 | −0.09159 (18) | 0.19806 (18) | 0.58651 (15) | 0.0417 (5) | |
H12A | −0.1544 | 0.1589 | 0.6029 | 0.063* | |
H12B | −0.0890 | 0.2042 | 0.5238 | 0.063* | |
H12C | −0.0984 | 0.2617 | 0.6124 | 0.063* | |
C13 | 0.54647 (17) | −0.13433 (16) | 0.81545 (15) | 0.0382 (5) | |
H13A | 0.5403 | −0.2012 | 0.8337 | 0.057* | |
H13B | 0.5827 | −0.0972 | 0.8606 | 0.057* | |
H13C | 0.5893 | −0.1308 | 0.7624 | 0.057* | |
C14 | 0.0729 (2) | −0.02339 (19) | 0.98105 (17) | 0.0553 (7) | |
H14A | 0.1398 | 0.0094 | 0.9635 | 0.083* | |
H14B | 0.0517 | −0.0694 | 0.9365 | 0.083* | |
H14C | 0.0855 | −0.0573 | 1.0353 | 0.083* | |
C15 | 0.01896 (19) | 0.12707 (17) | 1.05883 (14) | 0.0392 (5) | |
H15A | −0.0440 | 0.1628 | 1.0804 | 0.059* | |
H15B | 0.0697 | 0.1712 | 1.0307 | 0.059* | |
H15C | 0.0557 | 0.0953 | 1.1069 | 0.059* | |
C16 | −0.1547 (2) | 0.25275 (17) | 0.93947 (16) | 0.0468 (6) | |
H16A | −0.0941 | 0.2895 | 0.9152 | 0.070* | |
H16B | −0.1447 | 0.2463 | 1.0017 | 0.070* | |
H16C | −0.2233 | 0.2861 | 0.9279 | 0.070* | |
C1' | −0.05002 (15) | 0.09333 (13) | 0.90162 (12) | 0.0251 (4) | |
H1' | −0.0620 | 0.0367 | 0.8635 | 0.030* | |
C2' | −0.01964 (17) | 0.05123 (14) | 0.99346 (13) | 0.0326 (4) | |
C3' | −0.1224 (2) | −0.00184 (17) | 1.02658 (15) | 0.0464 (6) | |
H3' | −0.1362 | −0.0567 | 0.9868 | 0.056* | |
C4' | −0.2246 (2) | 0.0587 (2) | 1.02856 (17) | 0.0557 (7) | |
H4'1 | −0.2134 | 0.1147 | 1.0665 | 0.067* | |
H4'2 | −0.2860 | 0.0207 | 1.0517 | 0.067* | |
C5' | −0.25110 (19) | 0.0924 (2) | 0.93659 (17) | 0.0495 (6) | |
H5'1 | −0.3187 | 0.1310 | 0.9376 | 0.059* | |
H5'2 | −0.2641 | 0.0359 | 0.8996 | 0.059* | |
C6' | −0.15790 (16) | 0.15282 (15) | 0.89796 (13) | 0.0320 (4) | |
C7' | 0.04840 (15) | 0.14848 (14) | 0.86263 (12) | 0.0264 (4) | |
H7'1 | 0.1115 | 0.1381 | 0.9012 | 0.032* | |
H7'2 | 0.0308 | 0.2175 | 0.8650 | 0.032* | |
C4A | 0.19100 (14) | 0.18490 (12) | 0.74774 (12) | 0.0246 (4) | |
C5A | 0.30869 (14) | 0.04390 (13) | 0.79515 (11) | 0.0247 (3) | |
C9A | 0.22333 (14) | −0.01934 (12) | 0.77161 (12) | 0.0239 (3) | |
C10A | 0.08662 (14) | 0.12577 (12) | 0.76921 (12) | 0.0231 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0452 (3) | 0.1016 (5) | 0.0273 (3) | −0.0136 (3) | 0.0015 (2) | 0.0125 (3) |
Cl2 | 0.0290 (2) | 0.02518 (18) | 0.0444 (3) | −0.00250 (18) | 0.0014 (2) | −0.00183 (18) |
Cl3 | 0.1061 (6) | 0.0671 (4) | 0.0404 (3) | −0.0215 (4) | 0.0037 (4) | 0.0214 (3) |
O1 | 0.0184 (6) | 0.0326 (6) | 0.0249 (6) | 0.0001 (5) | −0.0001 (5) | −0.0002 (5) |
O2 | 0.0264 (7) | 0.0348 (7) | 0.0437 (8) | −0.0062 (6) | −0.0078 (6) | −0.0071 (6) |
O3 | 0.0225 (7) | 0.0420 (8) | 0.0489 (9) | −0.0001 (6) | −0.0099 (6) | −0.0104 (7) |
O4 | 0.0296 (7) | 0.0288 (6) | 0.0514 (9) | 0.0048 (6) | −0.0032 (7) | −0.0010 (6) |
O5 | 0.0207 (6) | 0.0301 (6) | 0.0479 (8) | −0.0031 (5) | −0.0017 (6) | −0.0053 (6) |
O6 | 0.0220 (7) | 0.0571 (9) | 0.0352 (8) | 0.0081 (6) | 0.0003 (6) | 0.0042 (7) |
C2 | 0.0239 (9) | 0.0427 (10) | 0.0242 (9) | 0.0005 (8) | −0.0023 (7) | 0.0005 (8) |
C3 | 0.0295 (10) | 0.0466 (11) | 0.0267 (9) | −0.0034 (9) | 0.0002 (8) | 0.0058 (8) |
C4 | 0.0219 (9) | 0.0399 (10) | 0.0276 (9) | −0.0049 (8) | 0.0032 (7) | 0.0008 (8) |
C5 | 0.0198 (8) | 0.0312 (8) | 0.0258 (8) | −0.0013 (7) | 0.0013 (7) | −0.0028 (7) |
C6 | 0.0186 (8) | 0.0376 (9) | 0.0247 (9) | −0.0003 (7) | −0.0016 (7) | −0.0018 (7) |
C7 | 0.0217 (9) | 0.0383 (9) | 0.0249 (9) | 0.0050 (7) | −0.0010 (7) | 0.0008 (7) |
C8 | 0.0249 (9) | 0.0308 (8) | 0.0257 (8) | 0.0038 (7) | 0.0007 (7) | 0.0018 (7) |
C9 | 0.0213 (8) | 0.0296 (8) | 0.0283 (9) | −0.0025 (7) | 0.0005 (7) | 0.0007 (7) |
C10 | 0.0198 (8) | 0.0265 (8) | 0.0266 (9) | −0.0012 (6) | 0.0000 (7) | −0.0031 (7) |
C11 | 0.0346 (11) | 0.0523 (12) | 0.0342 (11) | −0.0012 (10) | −0.0051 (9) | −0.0098 (9) |
C12 | 0.0298 (10) | 0.0571 (13) | 0.0382 (11) | 0.0044 (10) | −0.0071 (9) | 0.0079 (10) |
C13 | 0.0232 (9) | 0.0468 (11) | 0.0446 (12) | 0.0094 (8) | −0.0050 (8) | −0.0028 (9) |
C14 | 0.0690 (18) | 0.0546 (14) | 0.0423 (13) | 0.0287 (13) | −0.0004 (12) | 0.0124 (11) |
C15 | 0.0392 (12) | 0.0491 (12) | 0.0293 (10) | −0.0028 (10) | −0.0009 (9) | 0.0005 (9) |
C16 | 0.0445 (13) | 0.0477 (12) | 0.0483 (13) | 0.0171 (11) | 0.0013 (11) | −0.0072 (10) |
C1' | 0.0232 (9) | 0.0277 (8) | 0.0244 (9) | −0.0005 (7) | 0.0018 (7) | 0.0007 (7) |
C2' | 0.0371 (11) | 0.0336 (9) | 0.0272 (9) | 0.0026 (8) | 0.0013 (8) | 0.0028 (8) |
C3' | 0.0639 (16) | 0.0427 (11) | 0.0324 (11) | −0.0173 (11) | 0.0038 (10) | 0.0070 (9) |
C4' | 0.0439 (14) | 0.0769 (17) | 0.0463 (14) | −0.0196 (13) | 0.0134 (11) | 0.0089 (13) |
C5' | 0.0266 (11) | 0.0759 (16) | 0.0461 (13) | −0.0101 (11) | 0.0051 (10) | 0.0009 (12) |
C6' | 0.0204 (9) | 0.0440 (10) | 0.0317 (10) | 0.0028 (8) | 0.0027 (8) | −0.0010 (8) |
C7' | 0.0199 (9) | 0.0329 (9) | 0.0266 (9) | −0.0022 (7) | 0.0013 (7) | −0.0029 (7) |
C4A | 0.0201 (8) | 0.0239 (7) | 0.0298 (9) | −0.0019 (7) | 0.0001 (7) | −0.0020 (7) |
C5A | 0.0191 (8) | 0.0311 (8) | 0.0239 (8) | 0.0004 (7) | −0.0010 (7) | −0.0018 (7) |
C9A | 0.0182 (8) | 0.0291 (8) | 0.0243 (8) | 0.0010 (6) | 0.0011 (7) | −0.0005 (7) |
C10A | 0.0159 (7) | 0.0262 (8) | 0.0272 (9) | −0.0013 (6) | 0.0002 (7) | −0.0013 (7) |
Cl1—C3 | 1.785 (2) | C12—H12B | 0.9700 |
Cl2—C4A | 1.7919 (17) | C12—H12C | 0.9700 |
Cl3—C3' | 1.805 (2) | C13—H13A | 0.9700 |
O1—C10A | 1.420 (2) | C13—H13B | 0.9700 |
O1—C2 | 1.464 (2) | C13—H13C | 0.9700 |
O2—C5 | 1.219 (2) | C14—C2' | 1.539 (3) |
O3—C6 | 1.341 (2) | C14—H14A | 0.9700 |
O3—H3 | 0.79 (3) | C14—H14B | 0.9700 |
O4—C8 | 1.340 (2) | C14—H14C | 0.9700 |
O4—H4 | 0.83 (3) | C15—C2' | 1.528 (3) |
O5—C10 | 1.203 (2) | C15—H15A | 0.9700 |
O6—C6' | 1.443 (2) | C15—H15B | 0.9700 |
O6—H6 | 0.76 (3) | C15—H15C | 0.9700 |
C2—C12 | 1.512 (3) | C16—C6' | 1.524 (3) |
C2—C11 | 1.524 (3) | C16—H16A | 0.9700 |
C2—C3 | 1.529 (3) | C16—H16B | 0.9700 |
C3—C4 | 1.517 (3) | C16—H16C | 0.9700 |
C3—H3A | 0.9900 | C1'—C7' | 1.541 (2) |
C4—C4A | 1.534 (3) | C1'—C6' | 1.549 (3) |
C4—H4A | 0.9800 | C1'—C2' | 1.573 (3) |
C4—H4B | 0.9800 | C1'—H1' | 0.9900 |
C5—C5A | 1.448 (2) | C2'—C3' | 1.535 (3) |
C5—C4A | 1.534 (2) | C3'—C4' | 1.499 (4) |
C6—C7 | 1.393 (3) | C3'—H3' | 0.9900 |
C6—C5A | 1.409 (2) | C4'—C5' | 1.525 (4) |
C7—C8 | 1.387 (3) | C4'—H4'1 | 0.9800 |
C7—C13 | 1.496 (3) | C4'—H4'2 | 0.9800 |
C8—C9 | 1.401 (2) | C5'—C6' | 1.528 (3) |
C9—C9A | 1.370 (2) | C5'—H5'1 | 0.9800 |
C9—H9 | 0.9400 | C5'—H5'2 | 0.9800 |
C10—C9A | 1.480 (2) | C7'—C10A | 1.543 (2) |
C10—C10A | 1.547 (2) | C7'—H7'1 | 0.9800 |
C11—H11A | 0.9700 | C7'—H7'2 | 0.9800 |
C11—H11B | 0.9700 | C4A—C10A | 1.545 (2) |
C11—H11C | 0.9700 | C5A—C9A | 1.405 (2) |
C12—H12A | 0.9700 | ||
C10A—O1—C2 | 121.17 (14) | H15A—C15—H15C | 109.5 |
C6—O3—H3 | 106 (2) | H15B—C15—H15C | 109.5 |
C8—O4—H4 | 109 (2) | C6'—C16—H16A | 109.5 |
C6'—O6—H6 | 112.9 (18) | C6'—C16—H16B | 109.5 |
O1—C2—C12 | 102.75 (16) | H16A—C16—H16B | 109.5 |
O1—C2—C11 | 112.99 (16) | C6'—C16—H16C | 109.5 |
C12—C2—C11 | 109.81 (18) | H16A—C16—H16C | 109.5 |
O1—C2—C3 | 105.65 (15) | H16B—C16—H16C | 109.5 |
C12—C2—C3 | 111.43 (17) | C7'—C1'—C6' | 112.33 (15) |
C11—C2—C3 | 113.64 (17) | C7'—C1'—C2' | 110.57 (15) |
C4—C3—C2 | 112.47 (16) | C6'—C1'—C2' | 115.35 (15) |
C4—C3—Cl1 | 108.60 (14) | C7'—C1'—H1' | 105.9 |
C2—C3—Cl1 | 111.19 (14) | C6'—C1'—H1' | 105.9 |
C4—C3—H3A | 108.1 | C2'—C1'—H1' | 105.9 |
C2—C3—H3A | 108.1 | C15—C2'—C3' | 111.07 (18) |
Cl1—C3—H3A | 108.1 | C15—C2'—C14 | 108.55 (19) |
C3—C4—C4A | 109.58 (15) | C3'—C2'—C14 | 108.34 (19) |
C3—C4—H4A | 109.8 | C15—C2'—C1' | 114.18 (16) |
C4A—C4—H4A | 109.8 | C3'—C2'—C1' | 106.54 (17) |
C3—C4—H4B | 109.8 | C14—C2'—C1' | 107.97 (16) |
C4A—C4—H4B | 109.8 | C4'—C3'—C2' | 114.42 (18) |
H4A—C4—H4B | 108.2 | C4'—C3'—Cl3 | 108.41 (17) |
O2—C5—C5A | 122.98 (17) | C2'—C3'—Cl3 | 111.33 (17) |
O2—C5—C4A | 120.93 (16) | C4'—C3'—H3' | 107.5 |
C5A—C5—C4A | 115.83 (15) | C2'—C3'—H3' | 107.5 |
O3—C6—C7 | 117.39 (17) | Cl3—C3'—H3' | 107.5 |
O3—C6—C5A | 121.40 (17) | C3'—C4'—C5' | 109.1 (2) |
C7—C6—C5A | 121.18 (17) | C3'—C4'—H4'1 | 109.9 |
C8—C7—C6 | 118.49 (17) | C5'—C4'—H4'1 | 109.9 |
C8—C7—C13 | 121.00 (17) | C3'—C4'—H4'2 | 109.9 |
C6—C7—C13 | 120.51 (18) | C5'—C4'—H4'2 | 109.9 |
O4—C8—C7 | 117.79 (17) | H4'1—C4'—H4'2 | 108.3 |
O4—C8—C9 | 120.89 (17) | C4'—C5'—C6' | 111.8 (2) |
C7—C8—C9 | 121.32 (16) | C4'—C5'—H5'1 | 109.2 |
C9A—C9—C8 | 119.28 (16) | C6'—C5'—H5'1 | 109.2 |
C9A—C9—H9 | 120.4 | C4'—C5'—H5'2 | 109.2 |
C8—C9—H9 | 120.4 | C6'—C5'—H5'2 | 109.2 |
O5—C10—C9A | 121.86 (15) | H5'1—C5'—H5'2 | 107.9 |
O5—C10—C10A | 119.28 (16) | O6—C6'—C16 | 106.91 (17) |
C9A—C10—C10A | 118.80 (14) | O6—C6'—C5' | 104.66 (17) |
C2—C11—H11A | 109.5 | C16—C6'—C5' | 110.60 (19) |
C2—C11—H11B | 109.5 | O6—C6'—C1' | 108.72 (15) |
H11A—C11—H11B | 109.5 | C16—C6'—C1' | 116.44 (17) |
C2—C11—H11C | 109.5 | C5'—C6'—C1' | 108.83 (17) |
H11A—C11—H11C | 109.5 | C1'—C7'—C10A | 119.73 (15) |
H11B—C11—H11C | 109.5 | C1'—C7'—H7'1 | 107.4 |
C2—C12—H12A | 109.5 | C10A—C7'—H7'1 | 107.4 |
C2—C12—H12B | 109.5 | C1'—C7'—H7'2 | 107.4 |
H12A—C12—H12B | 109.5 | C10A—C7'—H7'2 | 107.4 |
C2—C12—H12C | 109.5 | H7'1—C7'—H7'2 | 106.9 |
H12A—C12—H12C | 109.5 | C4—C4A—C5 | 108.81 (14) |
H12B—C12—H12C | 109.5 | C4—C4A—C10A | 109.95 (14) |
C7—C13—H13A | 109.5 | C5—C4A—C10A | 111.92 (14) |
C7—C13—H13B | 109.5 | C4—C4A—Cl2 | 106.83 (13) |
H13A—C13—H13B | 109.5 | C5—C4A—Cl2 | 108.45 (12) |
C7—C13—H13C | 109.5 | C10A—C4A—Cl2 | 110.72 (11) |
H13A—C13—H13C | 109.5 | C9A—C5A—C6 | 118.06 (16) |
H13B—C13—H13C | 109.5 | C9A—C5A—C5 | 121.27 (16) |
C2'—C14—H14A | 109.5 | C6—C5A—C5 | 120.59 (16) |
C2'—C14—H14B | 109.5 | C9—C9A—C5A | 121.28 (16) |
H14A—C14—H14B | 109.5 | C9—C9A—C10 | 117.80 (15) |
C2'—C14—H14C | 109.5 | C5A—C9A—C10 | 120.85 (15) |
H14A—C14—H14C | 109.5 | O1—C10A—C7' | 106.97 (13) |
H14B—C14—H14C | 109.5 | O1—C10A—C4A | 110.54 (14) |
C2'—C15—H15A | 109.5 | C7'—C10A—C4A | 109.79 (14) |
C2'—C15—H15B | 109.5 | O1—C10A—C10 | 109.93 (14) |
H15A—C15—H15B | 109.5 | C7'—C10A—C10 | 108.20 (14) |
C2'—C15—H15C | 109.5 | C4A—C10A—C10 | 111.28 (13) |
C10A—O1—C2—C12 | −170.99 (15) | C3—C4—C4A—C10A | 54.9 (2) |
C10A—O1—C2—C11 | 70.7 (2) | C3—C4—C4A—Cl2 | −65.35 (17) |
C10A—O1—C2—C3 | −54.1 (2) | O2—C5—C4A—C4 | 99.7 (2) |
O1—C2—C3—C4 | 55.0 (2) | C5A—C5—C4A—C4 | −74.6 (2) |
C12—C2—C3—C4 | 165.87 (18) | O2—C5—C4A—C10A | −138.58 (18) |
C11—C2—C3—C4 | −69.4 (2) | C5A—C5—C4A—C10A | 47.1 (2) |
O1—C2—C3—Cl1 | 177.05 (13) | O2—C5—C4A—Cl2 | −16.1 (2) |
C12—C2—C3—Cl1 | −72.1 (2) | C5A—C5—C4A—Cl2 | 169.54 (13) |
C11—C2—C3—Cl1 | 52.6 (2) | O3—C6—C5A—C9A | −176.14 (17) |
C2—C3—C4—C4A | −59.9 (2) | C7—C6—C5A—C9A | 6.0 (3) |
Cl1—C3—C4—C4A | 176.58 (13) | O3—C6—C5A—C5 | 7.0 (3) |
O3—C6—C7—C8 | −179.87 (17) | C7—C6—C5A—C5 | −170.96 (18) |
C5A—C6—C7—C8 | −1.9 (3) | O2—C5—C5A—C9A | 168.68 (18) |
O3—C6—C7—C13 | −0.3 (3) | C4A—C5—C5A—C9A | −17.1 (3) |
C5A—C6—C7—C13 | 177.68 (18) | O2—C5—C5A—C6 | −14.5 (3) |
C6—C7—C8—O4 | 176.65 (17) | C4A—C5—C5A—C6 | 159.67 (16) |
C13—C7—C8—O4 | −2.9 (3) | C8—C9—C9A—C5A | −0.9 (3) |
C6—C7—C8—C9 | −3.8 (3) | C8—C9—C9A—C10 | −177.90 (16) |
C13—C7—C8—C9 | 176.67 (18) | C6—C5A—C9A—C9 | −4.5 (3) |
O4—C8—C9—C9A | −175.26 (18) | C5—C5A—C9A—C9 | 172.34 (17) |
C7—C8—C9—C9A | 5.2 (3) | C6—C5A—C9A—C10 | 172.39 (16) |
C7'—C1'—C2'—C15 | 56.9 (2) | C5—C5A—C9A—C10 | −10.7 (3) |
C6'—C1'—C2'—C15 | −71.9 (2) | O5—C10—C9A—C9 | 7.1 (3) |
C7'—C1'—C2'—C3' | 179.93 (16) | C10A—C10—C9A—C9 | −175.83 (16) |
C6'—C1'—C2'—C3' | 51.1 (2) | O5—C10—C9A—C5A | −169.90 (18) |
C7'—C1'—C2'—C14 | −63.9 (2) | C10A—C10—C9A—C5A | 7.1 (3) |
C6'—C1'—C2'—C14 | 167.31 (19) | C2—O1—C10A—C7' | 172.50 (15) |
C15—C2'—C3'—C4' | 69.9 (2) | C2—O1—C10A—C4A | 53.0 (2) |
C14—C2'—C3'—C4' | −170.9 (2) | C2—O1—C10A—C10 | −70.24 (19) |
C1'—C2'—C3'—C4' | −55.0 (2) | C1'—C7'—C10A—O1 | 64.04 (19) |
C15—C2'—C3'—Cl3 | −53.4 (2) | C1'—C7'—C10A—C4A | −175.98 (15) |
C14—C2'—C3'—Cl3 | 65.7 (2) | C1'—C7'—C10A—C10 | −54.3 (2) |
C1'—C2'—C3'—Cl3 | −178.32 (14) | C4—C4A—C10A—O1 | −49.68 (19) |
C2'—C3'—C4'—C5' | 60.9 (3) | C5—C4A—C10A—O1 | −170.73 (14) |
Cl3—C3'—C4'—C5' | −174.17 (18) | Cl2—C4A—C10A—O1 | 68.14 (16) |
C3'—C4'—C5'—C6' | −60.0 (3) | C4—C4A—C10A—C7' | −167.46 (15) |
C4'—C5'—C6'—O6 | 171.8 (2) | C5—C4A—C10A—C7' | 71.48 (18) |
C4'—C5'—C6'—C16 | −73.4 (3) | Cl2—C4A—C10A—C7' | −49.65 (16) |
C4'—C5'—C6'—C1' | 55.7 (3) | C4—C4A—C10A—C10 | 72.77 (18) |
C7'—C1'—C6'—O6 | 65.8 (2) | C5—C4A—C10A—C10 | −48.28 (19) |
C2'—C1'—C6'—O6 | −166.30 (16) | Cl2—C4A—C10A—C10 | −169.41 (12) |
C7'—C1'—C6'—C16 | −55.0 (2) | O5—C10—C10A—O1 | −37.2 (2) |
C2'—C1'—C6'—C16 | 72.9 (2) | C9A—C10—C10A—O1 | 145.66 (15) |
C7'—C1'—C6'—C5' | 179.20 (17) | O5—C10—C10A—C7' | 79.3 (2) |
C2'—C1'—C6'—C5' | −52.9 (2) | C9A—C10—C10A—C7' | −97.85 (18) |
C6'—C1'—C7'—C10A | −100.08 (19) | O5—C10—C10A—C4A | −160.03 (17) |
C2'—C1'—C7'—C10A | 129.49 (17) | C9A—C10—C10A—C4A | 22.9 (2) |
C3—C4—C4A—C5 | 177.76 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.79 (3) | 1.91 (3) | 2.617 (2) | 149 (3) |
O4—H4···O6i | 0.83 (3) | 1.89 (3) | 2.717 (2) | 176 (3) |
O6—H6···O1 | 0.76 (3) | 1.96 (3) | 2.717 (2) | 172 (2) |
Symmetry code: (i) −x, y−1/2, −z+3/2. |