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organic compounds
The title compound, C13H14O4, is isolated from the plant Goniothalamus wightii. There are four independent molecules in the asymmetric unit, having similar conformations. Two molecules are linked via O—H
O hydrogen bonds, forming chains along the a axis in the crystal structure.
O hydrogen bonds, forming chains along the a axis in the crystal structure.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046599/ob2083sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046599/ob2083Isup2.hkl |
CCDC reference: 630199
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.007 Å
Alert level B
Alert level C
Alert level G
Computing details top
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and WinGX (Farrugia, 1999).
8-Hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one top
Crystal data top
| C13H14O4 | F(000) = 992 |
| Mr = 234.24 | Dx = 1.323 Mg m−3 |
| Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
| a = 7.1313 (5) Å | Cell parameters from 25 reflections |
| b = 35.442 (3) Å | θ = 20–30° |
| c = 9.3061 (16) Å | µ = 0.81 mm−1 |
| β = 90.454 (9)° | T = 293 K |
| V = 2352.0 (5) Å3 | Prism, colourless |
| Z = 8 | 0.3 × 0.2 × 0.2 mm |
Data collection top
| Enraf–Nonius CAD-4 diffractometer | 3927 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.020 |
| Graphite monochromator | θmax = 67.9°, θmin = 2.5° |
| ω–2θ scans | h = −8→8 |
| Absorption correction: ψ scan (North et al., 1968) | k = 0→42 |
| Tmin = 0.943, Tmax = 0.999 | l = −9→11 |
| 4627 measured reflections | 2 standard reflections every 60 min |
| 4350 independent reflections | intensity decay: none |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0822P)2 + 0.8943P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.147 | (Δ/σ)max < 0.001 |
| S = 1.06 | Δρmax = 0.24 e Å−3 |
| 4350 reflections | Δρmin = −0.23 e Å−3 |
| 542 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 1 restraint | Extinction coefficient: 0.0083 (6) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
| Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (3) |
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 | ||
| C1A | 0.0643 (3) | 0.05926 (6) | 0.2652 (3) | 0.0793 (15) | |
| H1A | 0.0795 | 0.0762 | 0.1898 | 0.095* | |
| C2A | −0.0732 (3) | 0.03152 (6) | 0.2569 (3) | 0.097 (2) | |
| H2A | −0.1499 | 0.0299 | 0.1759 | 0.116* | |
| C3A | −0.0959 (3) | 0.00624 (6) | 0.3696 (3) | 0.104 (3) | |
| H3A | −0.1878 | −0.0123 | 0.3640 | 0.125* | |
| C4A | 0.0189 (3) | 0.00869 (6) | 0.4906 (3) | 0.0925 (19) | |
| H4A | 0.0037 | −0.0082 | 0.5660 | 0.111* | |
| C5A | 0.1564 (3) | 0.03642 (6) | 0.4990 (3) | 0.0772 (14) | |
| H5A | 0.2331 | 0.0381 | 0.5800 | 0.093* | |
| C6A | 0.1791 (3) | 0.06171 (6) | 0.3863 (3) | 0.0577 (10) | |
| C7A | 0.3231 (3) | 0.09256 (6) | 0.3963 (3) | 0.0556 (10) | |
| H7A | 0.3321 | 0.1050 | 0.3025 | 0.067* | |
| C8A | 0.6495 (6) | 0.10154 (16) | 0.4463 (6) | 0.0690 (14) | |
| H8A | 0.7643 | 0.0873 | 0.4675 | 0.083* | |
| C9A | 0.6805 (7) | 0.12476 (16) | 0.3107 (7) | 0.0701 (13) | |
| H91A | 0.8100 | 0.1332 | 0.3102 | 0.084* | |
| H92A | 0.6625 | 0.1084 | 0.2282 | 0.084* | |
| C10A | 0.5561 (7) | 0.15870 (16) | 0.2926 (7) | 0.0733 (15) | |
| C11A | 0.4361 (8) | 0.14961 (16) | 0.5321 (7) | 0.0785 (15) | |
| H11A | 0.4053 | 0.1664 | 0.6122 | 0.094* | |
| C12A | 0.2754 (7) | 0.12240 (15) | 0.5098 (8) | 0.0775 (16) | |
| H12A | 0.2493 | 0.1097 | 0.6009 | 0.093* | |
| C13A | 0.6140 (9) | 0.1286 (2) | 0.5695 (8) | 0.0893 (18) | |
| H13A | 0.5993 | 0.1148 | 0.6587 | 0.107* | |
| H14A | 0.7180 | 0.1460 | 0.5804 | 0.107* | |
| O1A | 0.4984 (4) | 0.07545 (9) | 0.4293 (4) | 0.0625 (8) | |
| O2A | 0.4602 (5) | 0.17218 (10) | 0.4044 (5) | 0.0835 (12) | |
| O3A | 0.1089 (5) | 0.14143 (13) | 0.4617 (9) | 0.130 (3) | |
| H31A | 0.1300 | 0.1641 | 0.4546 | 0.195* | |
| O4A | 0.5451 (6) | 0.17613 (14) | 0.1823 (6) | 0.1009 (16) | |
| C1B | 0.9585 (3) | 0.11424 (6) | 0.9156 (2) | 0.0873 (18) | |
| H1B | 0.8428 | 0.1263 | 0.9197 | 0.105* | |
| C2B | 0.9677 (3) | 0.07609 (6) | 0.8818 (2) | 0.125 (3) | |
| H2B | 0.8583 | 0.0626 | 0.8633 | 0.149* | |
| C3B | 1.1406 (3) | 0.05806 (6) | 0.8758 (2) | 0.141 (4) | |
| H3B | 1.1468 | 0.0325 | 0.8532 | 0.169* | |
| C4B | 1.3042 (3) | 0.07819 (6) | 0.9035 (2) | 0.122 (3) | |
| H4B | 1.4199 | 0.0661 | 0.8995 | 0.146* | |
| C5B | 1.2949 (3) | 0.11635 (6) | 0.9373 (2) | 0.0778 (15) | |
| H5B | 1.4044 | 0.1298 | 0.9559 | 0.093* | |
| C6B | 1.1221 (3) | 0.13437 (6) | 0.9433 (2) | 0.0564 (11) | |
| C7B | 1.1107 (3) | 0.17539 (6) | 0.9841 (2) | 0.0430 (8) | |
| H7B | 1.2378 | 0.1854 | 0.9974 | 0.052* | |
| C8B | 0.9761 (5) | 0.21359 (11) | 1.1732 (4) | 0.0430 (8) | |
| H8B | 0.9063 | 0.2111 | 1.2630 | 0.052* | |
| C9B | 1.1523 (5) | 0.23592 (12) | 1.2034 (4) | 0.0440 (8) | |
| H91B | 1.1249 | 0.2541 | 1.2782 | 0.053* | |
| H92B | 1.2462 | 0.2187 | 1.2416 | 0.053* | |
| C10B | 1.2367 (5) | 0.25668 (11) | 1.0795 (4) | 0.0441 (8) | |
| C11B | 0.9684 (5) | 0.23835 (11) | 0.9295 (4) | 0.0431 (8) | |
| H11B | 0.8938 | 0.2521 | 0.8578 | 0.052* | |
| C12B | 1.0072 (5) | 0.19920 (12) | 0.8730 (4) | 0.0431 (8) | |
| H12B | 0.8871 | 0.1870 | 0.8508 | 0.052* | |
| C13B | 0.8569 (5) | 0.23565 (12) | 1.0670 (4) | 0.0462 (9) | |
| H13B | 0.8305 | 0.2606 | 1.1042 | 0.055* | |
| H14B | 0.7389 | 0.2228 | 1.0495 | 0.055* | |
| O1B | 1.0143 (4) | 0.17648 (8) | 1.1191 (3) | 0.0479 (6) | |
| O2B | 1.1453 (4) | 0.25878 (8) | 0.9537 (3) | 0.0451 (6) | |
| O3B | 1.1172 (4) | 0.19953 (9) | 0.7467 (3) | 0.0535 (7) | |
| H31B | 1.0526 | 0.2065 | 0.6785 | 0.080* | |
| O4B | 1.3868 (4) | 0.27263 (11) | 1.0897 (3) | 0.0641 (9) | |
| C1C | 0.8143 (3) | 0.38168 (6) | 0.6782 (2) | 0.0773 (15) | |
| H1C | 0.9187 | 0.3667 | 0.6603 | 0.093* | |
| C2C | 0.8365 (3) | 0.41991 (6) | 0.7069 (2) | 0.110 (3) | |
| H2C | 0.9558 | 0.4305 | 0.7084 | 0.132* | |
| C3C | 0.6805 (3) | 0.44227 (6) | 0.7336 (2) | 0.116 (3) | |
| H3C | 0.6953 | 0.4678 | 0.7529 | 0.139* | |
| C4C | 0.5022 (3) | 0.42640 (6) | 0.7315 (2) | 0.101 (2) | |
| H4C | 0.3978 | 0.4414 | 0.7494 | 0.122* | |
| C5C | 0.4800 (3) | 0.38817 (6) | 0.7027 (2) | 0.0784 (15) | |
| H5C | 0.3608 | 0.3775 | 0.7013 | 0.094* | |
| C6C | 0.6360 (3) | 0.36581 (6) | 0.6761 (2) | 0.0556 (11) | |
| C7C | 0.6132 (3) | 0.32445 (6) | 0.6356 (2) | 0.0444 (8) | |
| H7C | 0.7378 | 0.3134 | 0.6222 | 0.053* | |
| C8C | 0.4740 (5) | 0.28716 (11) | 0.4468 (4) | 0.0443 (8) | |
| H8C | 0.4028 | 0.2900 | 0.3570 | 0.053* | |
| C9C | 0.6501 (5) | 0.26435 (12) | 0.4151 (4) | 0.0467 (9) | |
| H91C | 0.6206 | 0.2463 | 0.3399 | 0.056* | |
| H92C | 0.7446 | 0.2814 | 0.3779 | 0.056* | |
| C10C | 0.7333 (5) | 0.24330 (12) | 0.5404 (4) | 0.0447 (8) | |
| C11C | 0.4683 (5) | 0.26237 (11) | 0.6886 (4) | 0.0416 (8) | |
| H11C | 0.3944 | 0.2486 | 0.7597 | 0.050* | |
| C12C | 0.5090 (5) | 0.30127 (11) | 0.7475 (4) | 0.0426 (8) | |
| H12C | 0.3894 | 0.3138 | 0.7674 | 0.051* | |
| C13C | 0.3548 (5) | 0.26489 (12) | 0.5514 (4) | 0.0466 (9) | |
| H13C | 0.2368 | 0.2777 | 0.5683 | 0.056* | |
| H14C | 0.3286 | 0.2399 | 0.5139 | 0.056* | |
| O1C | 0.5162 (4) | 0.32416 (8) | 0.5012 (3) | 0.0476 (6) | |
| O2C | 0.6430 (4) | 0.24182 (8) | 0.6658 (3) | 0.0446 (6) | |
| O3C | 0.6170 (4) | 0.30096 (9) | 0.8748 (3) | 0.0516 (7) | |
| H31C | 0.5540 | 0.2925 | 0.9408 | 0.077* | |
| O4C | 0.8803 (5) | 0.22639 (11) | 0.5309 (3) | 0.0663 (9) | |
| C1D | −0.3835 (3) | 0.45678 (6) | 0.1017 (3) | 0.0847 (17) | |
| H1D | −0.3290 | 0.4513 | 0.0137 | 0.102* | |
| C2D | −0.5171 (3) | 0.48520 (6) | 0.1115 (3) | 0.103 (2) | |
| H2D | −0.5520 | 0.4988 | 0.0300 | 0.124* | |
| C3D | −0.5986 (3) | 0.49338 (6) | 0.2431 (3) | 0.100 (2) | |
| H3D | −0.6879 | 0.5124 | 0.2496 | 0.120* | |
| C4D | −0.5464 (3) | 0.47313 (6) | 0.3649 (3) | 0.132 (4) | |
| H4D | −0.6009 | 0.4786 | 0.4529 | 0.159* | |
| C5D | −0.4128 (3) | 0.44470 (6) | 0.3552 (3) | 0.105 (3) | |
| H5D | −0.3780 | 0.4312 | 0.4367 | 0.127* | |
| C6D | −0.3314 (3) | 0.43653 (6) | 0.2236 (3) | 0.0517 (9) | |
| C7D | −0.1840 (3) | 0.40637 (6) | 0.2159 (3) | 0.0498 (9) | |
| H7D | −0.1762 | 0.3941 | 0.3102 | 0.060* | |
| C8D | 0.1465 (7) | 0.39881 (18) | 0.1794 (8) | 0.0804 (18) | |
| H8D | 0.2603 | 0.4135 | 0.1611 | 0.096* | |
| C9D | 0.1762 (7) | 0.37639 (17) | 0.3153 (7) | 0.0775 (15) | |
| H91D | 0.1512 | 0.3926 | 0.3970 | 0.093* | |
| H92D | 0.3067 | 0.3688 | 0.3211 | 0.093* | |
| C10D | 0.0545 (7) | 0.34142 (16) | 0.3268 (8) | 0.0759 (17) | |
| C11D | −0.0562 (9) | 0.3507 (2) | 0.0862 (8) | 0.0889 (18) | |
| H11D | −0.0814 | 0.3339 | 0.0047 | 0.107* | |
| C12D | −0.2225 (8) | 0.37629 (16) | 0.1049 (8) | 0.0789 (16) | |
| H12D | −0.2463 | 0.3889 | 0.0129 | 0.095* | |
| C13D | 0.1161 (10) | 0.3724 (2) | 0.0560 (8) | 0.099 (2) | |
| H13D | 0.1017 | 0.3865 | −0.0329 | 0.119* | |
| H14D | 0.2223 | 0.3555 | 0.0466 | 0.119* | |
| O1D | −0.0089 (4) | 0.42460 (9) | 0.1901 (4) | 0.0651 (9) | |
| O2D | −0.0326 (5) | 0.32787 (11) | 0.2144 (5) | 0.0833 (11) | |
| O3D | −0.3864 (6) | 0.35684 (14) | 0.1428 (9) | 0.138 (3) | |
| H31D | −0.4076 | 0.3402 | 0.0836 | 0.207* | |
| O4D | 0.0435 (6) | 0.32420 (15) | 0.4391 (6) | 0.1080 (17) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1A | 0.067 (3) | 0.088 (4) | 0.082 (4) | −0.015 (3) | 0.002 (3) | −0.003 (3) |
| C2A | 0.080 (4) | 0.108 (5) | 0.102 (5) | −0.024 (4) | −0.004 (3) | −0.016 (4) |
| C3A | 0.088 (4) | 0.079 (4) | 0.146 (7) | −0.027 (3) | 0.036 (4) | −0.037 (4) |
| C4A | 0.111 (5) | 0.061 (3) | 0.106 (5) | −0.021 (3) | 0.034 (4) | 0.003 (3) |
| C5A | 0.095 (4) | 0.058 (3) | 0.078 (3) | −0.014 (3) | 0.007 (3) | 0.008 (3) |
| C6A | 0.058 (2) | 0.050 (2) | 0.066 (3) | −0.003 (2) | 0.012 (2) | −0.002 (2) |
| C7A | 0.046 (2) | 0.052 (2) | 0.069 (3) | 0.0019 (18) | 0.0052 (18) | 0.013 (2) |
| C8A | 0.044 (2) | 0.076 (3) | 0.088 (4) | 0.004 (2) | 0.000 (2) | 0.019 (3) |
| C9A | 0.047 (2) | 0.074 (3) | 0.090 (4) | −0.002 (2) | 0.011 (2) | 0.015 (3) |
| C10A | 0.044 (2) | 0.065 (3) | 0.111 (4) | −0.014 (2) | −0.006 (3) | 0.028 (3) |
| C11A | 0.073 (3) | 0.063 (3) | 0.100 (4) | −0.013 (3) | 0.021 (3) | −0.015 (3) |
| C12A | 0.056 (3) | 0.052 (3) | 0.126 (5) | −0.004 (2) | 0.027 (3) | −0.014 (3) |
| C13A | 0.073 (4) | 0.099 (5) | 0.096 (4) | −0.023 (3) | −0.013 (3) | 0.002 (4) |
| O1A | 0.0497 (16) | 0.0546 (17) | 0.083 (2) | 0.0097 (14) | 0.0099 (15) | 0.0103 (16) |
| O2A | 0.058 (2) | 0.0512 (19) | 0.141 (4) | −0.0030 (16) | 0.012 (2) | 0.005 (2) |
| O3A | 0.046 (2) | 0.062 (2) | 0.282 (8) | 0.0100 (18) | 0.030 (3) | −0.014 (3) |
| O4A | 0.060 (2) | 0.106 (3) | 0.137 (4) | −0.013 (2) | −0.005 (2) | 0.064 (3) |
| C1B | 0.114 (5) | 0.060 (3) | 0.087 (4) | −0.010 (3) | −0.029 (3) | −0.008 (3) |
| C2B | 0.217 (11) | 0.065 (4) | 0.090 (5) | −0.027 (5) | −0.031 (6) | −0.015 (3) |
| C3B | 0.284 (14) | 0.052 (4) | 0.087 (5) | 0.002 (6) | 0.050 (7) | −0.013 (3) |
| C4B | 0.187 (9) | 0.069 (4) | 0.111 (6) | 0.050 (5) | 0.061 (6) | 0.004 (4) |
| C5B | 0.097 (4) | 0.059 (3) | 0.077 (3) | 0.020 (3) | 0.020 (3) | 0.000 (2) |
| C6B | 0.085 (3) | 0.048 (2) | 0.0359 (19) | 0.005 (2) | 0.0032 (19) | −0.0013 (17) |
| C7B | 0.0481 (19) | 0.045 (2) | 0.0356 (17) | 0.0030 (16) | 0.0083 (14) | −0.0023 (15) |
| C8B | 0.0434 (19) | 0.049 (2) | 0.0367 (17) | 0.0037 (16) | 0.0119 (14) | 0.0008 (15) |
| C9B | 0.048 (2) | 0.050 (2) | 0.0334 (17) | 0.0040 (17) | 0.0021 (14) | 0.0012 (15) |
| C10B | 0.045 (2) | 0.052 (2) | 0.0360 (17) | 0.0008 (17) | 0.0052 (14) | −0.0041 (16) |
| C11B | 0.0405 (18) | 0.053 (2) | 0.0357 (17) | 0.0037 (16) | −0.0004 (14) | −0.0016 (16) |
| C12B | 0.0411 (18) | 0.053 (2) | 0.0353 (17) | 0.0011 (17) | 0.0020 (14) | −0.0023 (16) |
| C13B | 0.0390 (18) | 0.056 (2) | 0.0441 (19) | 0.0055 (16) | 0.0066 (15) | −0.0004 (17) |
| O1B | 0.0575 (15) | 0.0472 (15) | 0.0393 (13) | −0.0008 (12) | 0.0116 (11) | 0.0031 (11) |
| O2B | 0.0463 (14) | 0.0531 (15) | 0.0361 (12) | −0.0055 (12) | 0.0039 (10) | 0.0030 (11) |
| O3B | 0.0589 (16) | 0.0682 (18) | 0.0335 (12) | 0.0092 (14) | 0.0069 (11) | −0.0009 (12) |
| O4B | 0.0579 (17) | 0.090 (2) | 0.0444 (15) | −0.0286 (17) | 0.0033 (13) | −0.0002 (15) |
| C1C | 0.101 (4) | 0.066 (3) | 0.065 (3) | −0.029 (3) | −0.002 (3) | 0.007 (2) |
| C2C | 0.176 (8) | 0.069 (4) | 0.085 (4) | −0.053 (5) | −0.008 (5) | 0.009 (3) |
| C3C | 0.238 (11) | 0.056 (3) | 0.053 (3) | −0.024 (5) | −0.005 (5) | 0.000 (3) |
| C4C | 0.166 (7) | 0.066 (4) | 0.072 (4) | 0.034 (4) | 0.007 (4) | −0.003 (3) |
| C5C | 0.106 (4) | 0.060 (3) | 0.069 (3) | 0.017 (3) | 0.011 (3) | 0.000 (2) |
| C6C | 0.083 (3) | 0.046 (2) | 0.038 (2) | −0.007 (2) | −0.0004 (19) | 0.0007 (16) |
| C7C | 0.047 (2) | 0.051 (2) | 0.0349 (17) | −0.0001 (17) | −0.0010 (14) | 0.0007 (16) |
| C8C | 0.046 (2) | 0.052 (2) | 0.0350 (17) | −0.0030 (16) | −0.0065 (14) | 0.0010 (15) |
| C9C | 0.048 (2) | 0.056 (2) | 0.0360 (18) | −0.0028 (17) | 0.0017 (15) | −0.0006 (17) |
| C10C | 0.0436 (19) | 0.056 (2) | 0.0347 (17) | 0.0036 (17) | −0.0001 (14) | −0.0025 (16) |
| C11C | 0.0393 (17) | 0.051 (2) | 0.0348 (17) | −0.0021 (16) | 0.0061 (14) | 0.0042 (15) |
| C12C | 0.0405 (18) | 0.052 (2) | 0.0352 (17) | 0.0015 (16) | 0.0021 (13) | 0.0010 (16) |
| C13C | 0.0397 (18) | 0.058 (2) | 0.0424 (19) | −0.0035 (17) | −0.0010 (15) | −0.0018 (17) |
| O1C | 0.0559 (15) | 0.0488 (14) | 0.0382 (13) | 0.0019 (13) | −0.0036 (11) | 0.0031 (11) |
| O2C | 0.0478 (14) | 0.0511 (15) | 0.0348 (12) | 0.0051 (12) | −0.0001 (10) | 0.0022 (11) |
| O3C | 0.0622 (16) | 0.0602 (16) | 0.0325 (12) | −0.0035 (14) | −0.0003 (11) | −0.0006 (12) |
| O4C | 0.0598 (18) | 0.092 (2) | 0.0476 (15) | 0.0272 (18) | 0.0032 (13) | −0.0038 (15) |
| C1D | 0.121 (5) | 0.068 (3) | 0.065 (3) | 0.024 (3) | 0.005 (3) | 0.010 (3) |
| C2D | 0.127 (6) | 0.062 (3) | 0.121 (6) | 0.020 (4) | −0.016 (5) | 0.030 (4) |
| C3D | 0.088 (4) | 0.069 (4) | 0.143 (7) | 0.027 (3) | 0.011 (4) | 0.006 (4) |
| C4D | 0.136 (7) | 0.161 (8) | 0.099 (5) | 0.077 (7) | 0.026 (5) | −0.006 (5) |
| C5D | 0.106 (5) | 0.146 (7) | 0.065 (3) | 0.064 (5) | 0.018 (3) | 0.015 (4) |
| C6D | 0.053 (2) | 0.047 (2) | 0.055 (2) | −0.0012 (18) | 0.0003 (18) | −0.0010 (18) |
| C7D | 0.046 (2) | 0.047 (2) | 0.056 (2) | −0.0028 (17) | 0.0008 (17) | 0.0048 (18) |
| C8D | 0.039 (2) | 0.080 (4) | 0.123 (5) | −0.011 (2) | 0.006 (3) | 0.037 (4) |
| C9D | 0.051 (3) | 0.075 (3) | 0.106 (4) | −0.005 (2) | −0.015 (3) | 0.015 (3) |
| C10D | 0.047 (2) | 0.067 (3) | 0.114 (5) | 0.020 (2) | 0.013 (3) | 0.035 (3) |
| C11D | 0.086 (4) | 0.085 (4) | 0.096 (4) | 0.030 (3) | −0.011 (3) | −0.024 (3) |
| C12D | 0.065 (3) | 0.064 (3) | 0.108 (4) | 0.011 (3) | −0.018 (3) | −0.026 (3) |
| C13D | 0.088 (4) | 0.113 (5) | 0.097 (5) | 0.036 (4) | 0.032 (4) | 0.009 (4) |
| O1D | 0.0488 (16) | 0.0527 (17) | 0.094 (2) | −0.0091 (13) | −0.0045 (15) | 0.0137 (16) |
| O2D | 0.060 (2) | 0.063 (2) | 0.127 (3) | 0.0033 (17) | −0.005 (2) | −0.001 (2) |
| O3D | 0.054 (2) | 0.071 (3) | 0.288 (8) | −0.004 (2) | −0.032 (3) | −0.054 (4) |
| O4D | 0.075 (3) | 0.111 (3) | 0.138 (4) | 0.029 (2) | 0.018 (2) | 0.064 (3) |
Geometric parameters (Å, º) top
| C1A—C2A | 1.3900 | C1C—C2C | 1.3900 |
| C1A—C6A | 1.3900 | C1C—C6C | 1.3900 |
| C1A—H1A | 0.9300 | C1C—H1C | 0.9300 |
| C2A—C3A | 1.3900 | C2C—C3C | 1.3900 |
| C2A—H2A | 0.9300 | C2C—H2C | 0.9300 |
| C3A—C4A | 1.3900 | C3C—C4C | 1.3900 |
| C3A—H3A | 0.9300 | C3C—H3C | 0.9300 |
| C4A—C5A | 1.3900 | C4C—C5C | 1.3900 |
| C4A—H4A | 0.9300 | C4C—H4C | 0.9300 |
| C5A—C6A | 1.3900 | C5C—C6C | 1.3900 |
| C5A—H5A | 0.9300 | C5C—H5C | 0.9300 |
| C6A—C7A | 1.5027 | C6C—C7C | 1.5219 |
| C7A—O1A | 1.420 (4) | C7C—O1C | 1.425 (3) |
| C7A—C12A | 1.534 (6) | C7C—C12C | 1.524 (4) |
| C7A—H7A | 0.9800 | C7C—H7C | 0.9800 |
| C8A—O1A | 1.428 (6) | C8C—O1C | 1.437 (5) |
| C8A—C13A | 1.516 (9) | C8C—C13C | 1.518 (5) |
| C8A—C9A | 1.524 (7) | C8C—C9C | 1.525 (6) |
| C8A—H8A | 0.9800 | C8C—H8C | 0.9800 |
| C9A—C10A | 1.504 (8) | C9C—C10C | 1.502 (5) |
| C9A—H91A | 0.9700 | C9C—H91C | 0.9700 |
| C9A—H92A | 0.9700 | C9C—H92C | 0.9700 |
| C10A—O4A | 1.200 (7) | C10C—O4C | 1.212 (5) |
| C10A—O2A | 1.338 (8) | C10C—O2C | 1.338 (4) |
| C11A—O2A | 1.444 (8) | C11C—O2C | 1.460 (4) |
| C11A—C13A | 1.510 (9) | C11C—C13C | 1.508 (5) |
| C11A—C12A | 1.511 (7) | C11C—C12C | 1.511 (5) |
| C11A—H11A | 0.9800 | C11C—H11C | 0.9800 |
| C12A—O3A | 1.434 (8) | C12C—O3C | 1.408 (4) |
| C12A—H12A | 0.9800 | C12C—H12C | 0.9800 |
| C13A—H13A | 0.9700 | C13C—H13C | 0.9700 |
| C13A—H14A | 0.9700 | C13C—H14C | 0.9700 |
| O3A—H31A | 0.8200 | O3C—H31C | 0.8200 |
| C1B—C2B | 1.3900 | C1D—C2D | 1.3900 |
| C1B—C6B | 1.3900 | C1D—C6D | 1.3900 |
| C1B—H1B | 0.9300 | C1D—H1D | 0.9300 |
| C2B—C3B | 1.3900 | C2D—C3D | 1.3900 |
| C2B—H2B | 0.9300 | C2D—H2D | 0.9300 |
| C3B—C4B | 1.3900 | C3D—C4D | 1.3900 |
| C3B—H3B | 0.9300 | C3D—H3D | 0.9300 |
| C4B—C5B | 1.3900 | C4D—C5D | 1.3900 |
| C4B—H4B | 0.9300 | C4D—H4D | 0.9300 |
| C5B—C6B | 1.3900 | C5D—C6D | 1.3900 |
| C5B—H5B | 0.9300 | C5D—H5D | 0.9300 |
| C6B—C7B | 1.5050 | C6D—C7D | 1.5012 |
| C7B—O1B | 1.438 (3) | C7D—O1D | 1.428 (4) |
| C7B—C12B | 1.521 (4) | C7D—C12D | 1.508 (6) |
| C7B—H7B | 0.9800 | C7D—H7D | 0.9800 |
| C8B—O1B | 1.435 (5) | C8D—O1D | 1.440 (7) |
| C8B—C9B | 1.510 (5) | C8D—C13D | 1.496 (10) |
| C8B—C13B | 1.515 (5) | C8D—C9D | 1.508 (8) |
| C8B—H8B | 0.9800 | C8D—H8D | 0.9800 |
| C9B—C10B | 1.499 (5) | C9D—C10D | 1.517 (8) |
| C9B—H91B | 0.9700 | C9D—H91D | 0.9700 |
| C9B—H92B | 0.9700 | C9D—H92D | 0.9700 |
| C10B—O4B | 1.214 (5) | C10D—O4D | 1.213 (7) |
| C10B—O2B | 1.337 (5) | C10D—O2D | 1.304 (8) |
| C11B—O2B | 1.470 (5) | C11D—O2D | 1.451 (9) |
| C11B—C12B | 1.510 (6) | C11D—C13D | 1.478 (10) |
| C11B—C13B | 1.516 (5) | C11D—C12D | 1.504 (8) |
| C11B—H11B | 0.9800 | C11D—H11D | 0.9800 |
| C12B—O3B | 1.418 (4) | C12D—O3D | 1.404 (8) |
| C12B—H12B | 0.9800 | C12D—H12D | 0.9800 |
| C13B—H13B | 0.9700 | C13D—H13D | 0.9700 |
| C13B—H14B | 0.9700 | C13D—H14D | 0.9700 |
| O3B—H31B | 0.8200 | O3D—H31D | 0.8200 |
| C2A—C1A—C6A | 120.0 | C2C—C1C—C6C | 120.0 |
| C2A—C1A—H1A | 120.0 | C2C—C1C—H1C | 120.0 |
| C6A—C1A—H1A | 120.0 | C6C—C1C—H1C | 120.0 |
| C1A—C2A—C3A | 120.0 | C3C—C2C—C1C | 120.0 |
| C1A—C2A—H2A | 120.0 | C3C—C2C—H2C | 120.0 |
| C3A—C2A—H2A | 120.0 | C1C—C2C—H2C | 120.0 |
| C4A—C3A—C2A | 120.0 | C4C—C3C—C2C | 120.0 |
| C4A—C3A—H3A | 120.0 | C4C—C3C—H3C | 120.0 |
| C2A—C3A—H3A | 120.0 | C2C—C3C—H3C | 120.0 |
| C5A—C4A—C3A | 120.0 | C3C—C4C—C5C | 120.0 |
| C5A—C4A—H4A | 120.0 | C3C—C4C—H4C | 120.0 |
| C3A—C4A—H4A | 120.0 | C5C—C4C—H4C | 120.0 |
| C4A—C5A—C6A | 120.0 | C6C—C5C—C4C | 120.0 |
| C4A—C5A—H5A | 120.0 | C6C—C5C—H5C | 120.0 |
| C6A—C5A—H5A | 120.0 | C4C—C5C—H5C | 120.0 |
| C5A—C6A—C1A | 120.0 | C5C—C6C—C1C | 120.0 |
| C5A—C6A—C7A | 120.4 | C5C—C6C—C7C | 120.6 |
| C1A—C6A—C7A | 119.6 | C1C—C6C—C7C | 119.3 |
| O1A—C7A—C6A | 107.62 (16) | O1C—C7C—C6C | 105.91 (14) |
| O1A—C7A—C12A | 110.2 (3) | O1C—C7C—C12C | 111.1 (2) |
| C6A—C7A—C12A | 112.9 (2) | C6C—C7C—C12C | 113.72 (17) |
| O1A—C7A—H7A | 108.7 | O1C—C7C—H7C | 108.6 |
| C6A—C7A—H7A | 108.7 | C6C—C7C—H7C | 108.6 |
| C12A—C7A—H7A | 108.7 | C12C—C7C—H7C | 108.6 |
| O1A—C8A—C13A | 111.2 (4) | O1C—C8C—C13C | 111.5 (3) |
| O1A—C8A—C9A | 111.8 (4) | O1C—C8C—C9C | 112.4 (3) |
| C13A—C8A—C9A | 108.1 (5) | C13C—C8C—C9C | 108.3 (3) |
| O1A—C8A—H8A | 108.5 | O1C—C8C—H8C | 108.2 |
| C13A—C8A—H8A | 108.5 | C13C—C8C—H8C | 108.2 |
| C9A—C8A—H8A | 108.5 | C9C—C8C—H8C | 108.2 |
| C10A—C9A—C8A | 115.8 (5) | C10C—C9C—C8C | 115.7 (3) |
| C10A—C9A—H91A | 108.3 | C10C—C9C—H91C | 108.4 |
| C8A—C9A—H91A | 108.3 | C8C—C9C—H91C | 108.4 |
| C10A—C9A—H92A | 108.3 | C10C—C9C—H92C | 108.4 |
| C8A—C9A—H92A | 108.3 | C8C—C9C—H92C | 108.4 |
| H91A—C9A—H92A | 107.4 | H91C—C9C—H92C | 107.4 |
| O4A—C10A—O2A | 116.8 (5) | O4C—C10C—O2C | 117.9 (3) |
| O4A—C10A—C9A | 122.9 (6) | O4C—C10C—C9C | 121.7 (3) |
| O2A—C10A—C9A | 120.2 (5) | O2C—C10C—C9C | 120.4 (3) |
| O2A—C11A—C13A | 111.0 (5) | O2C—C11C—C13C | 111.1 (3) |
| O2A—C11A—C12A | 109.6 (5) | O2C—C11C—C12C | 110.2 (3) |
| C13A—C11A—C12A | 110.6 (5) | C13C—C11C—C12C | 110.7 (3) |
| O2A—C11A—H11A | 108.6 | O2C—C11C—H11C | 108.3 |
| C13A—C11A—H11A | 108.6 | C13C—C11C—H11C | 108.3 |
| C12A—C11A—H11A | 108.6 | C12C—C11C—H11C | 108.3 |
| O3A—C12A—C11A | 111.6 (5) | O3C—C12C—C11C | 113.6 (3) |
| O3A—C12A—C7A | 107.3 (5) | O3C—C12C—C7C | 108.2 (3) |
| C11A—C12A—C7A | 111.3 (4) | C11C—C12C—C7C | 109.7 (3) |
| O3A—C12A—H12A | 108.9 | O3C—C12C—H12C | 108.4 |
| C11A—C12A—H12A | 108.9 | C11C—C12C—H12C | 108.4 |
| C7A—C12A—H12A | 108.9 | C7C—C12C—H12C | 108.4 |
| C11A—C13A—C8A | 106.4 (5) | C11C—C13C—C8C | 105.9 (3) |
| C11A—C13A—H13A | 110.4 | C11C—C13C—H13C | 110.6 |
| C8A—C13A—H13A | 110.4 | C8C—C13C—H13C | 110.6 |
| C11A—C13A—H14A | 110.4 | C11C—C13C—H14C | 110.6 |
| C8A—C13A—H14A | 110.4 | C8C—C13C—H14C | 110.6 |
| H13A—C13A—H14A | 108.6 | H13C—C13C—H14C | 108.7 |
| C7A—O1A—C8A | 114.2 (3) | C7C—O1C—C8C | 114.5 (2) |
| C10A—O2A—C11A | 120.5 (4) | C10C—O2C—C11C | 121.6 (3) |
| C12A—O3A—H31A | 109.5 | C12C—O3C—H31C | 109.5 |
| C2B—C1B—C6B | 120.0 | C2D—C1D—C6D | 120.0 |
| C2B—C1B—H1B | 120.0 | C2D—C1D—H1D | 120.0 |
| C6B—C1B—H1B | 120.0 | C6D—C1D—H1D | 120.0 |
| C1B—C2B—C3B | 120.0 | C3D—C2D—C1D | 120.0 |
| C1B—C2B—H2B | 120.0 | C3D—C2D—H2D | 120.0 |
| C3B—C2B—H2B | 120.0 | C1D—C2D—H2D | 120.0 |
| C2B—C3B—C4B | 120.0 | C2D—C3D—C4D | 120.0 |
| C2B—C3B—H3B | 120.0 | C2D—C3D—H3D | 120.0 |
| C4B—C3B—H3B | 120.0 | C4D—C3D—H3D | 120.0 |
| C5B—C4B—C3B | 120.0 | C5D—C4D—C3D | 120.0 |
| C5B—C4B—H4B | 120.0 | C5D—C4D—H4D | 120.0 |
| C3B—C4B—H4B | 120.0 | C3D—C4D—H4D | 120.0 |
| C6B—C5B—C4B | 120.0 | C4D—C5D—C6D | 120.0 |
| C6B—C5B—H5B | 120.0 | C4D—C5D—H5D | 120.0 |
| C4B—C5B—H5B | 120.0 | C6D—C5D—H5D | 120.0 |
| C5B—C6B—C1B | 120.0 | C5D—C6D—C1D | 120.0 |
| C5B—C6B—C7B | 120.2 | C5D—C6D—C7D | 119.2 |
| C1B—C6B—C7B | 119.7 | C1D—C6D—C7D | 120.8 |
| O1B—C7B—C6B | 105.87 (14) | O1D—C7D—C6D | 107.41 (16) |
| O1B—C7B—C12B | 110.3 (2) | O1D—C7D—C12D | 111.0 (3) |
| C6B—C7B—C12B | 113.02 (17) | C6D—C7D—C12D | 114.3 (2) |
| O1B—C7B—H7B | 109.2 | O1D—C7D—H7D | 107.9 |
| C6B—C7B—H7B | 109.2 | C6D—C7D—H7D | 107.9 |
| C12B—C7B—H7B | 109.2 | C12D—C7D—H7D | 107.9 |
| O1B—C8B—C9B | 112.7 (3) | O1D—C8D—C13D | 110.1 (5) |
| O1B—C8B—C13B | 110.6 (3) | O1D—C8D—C9D | 112.3 (5) |
| C9B—C8B—C13B | 108.2 (3) | C13D—C8D—C9D | 109.5 (6) |
| O1B—C8B—H8B | 108.4 | O1D—C8D—H8D | 108.3 |
| C9B—C8B—H8B | 108.4 | C13D—C8D—H8D | 108.3 |
| C13B—C8B—H8B | 108.4 | C9D—C8D—H8D | 108.3 |
| C10B—C9B—C8B | 116.9 (3) | C8D—C9D—C10D | 114.4 (5) |
| C10B—C9B—H91B | 108.1 | C8D—C9D—H91D | 108.7 |
| C8B—C9B—H91B | 108.1 | C10D—C9D—H91D | 108.7 |
| C10B—C9B—H92B | 108.1 | C8D—C9D—H92D | 108.7 |
| C8B—C9B—H92B | 108.1 | C10D—C9D—H92D | 108.7 |
| H91B—C9B—H92B | 107.3 | H91D—C9D—H92D | 107.6 |
| O4B—C10B—O2B | 117.8 (3) | O4D—C10D—O2D | 118.1 (6) |
| O4B—C10B—C9B | 121.8 (3) | O4D—C10D—C9D | 120.8 (7) |
| O2B—C10B—C9B | 120.3 (3) | O2D—C10D—C9D | 120.9 (5) |
| O2B—C11B—C12B | 110.3 (3) | O2D—C11D—C13D | 110.8 (5) |
| O2B—C11B—C13B | 110.9 (3) | O2D—C11D—C12D | 109.1 (6) |
| C12B—C11B—C13B | 109.5 (3) | C13D—C11D—C12D | 111.4 (6) |
| O2B—C11B—H11B | 108.7 | O2D—C11D—H11D | 108.5 |
| C12B—C11B—H11B | 108.7 | C13D—C11D—H11D | 108.5 |
| C13B—C11B—H11B | 108.7 | C12D—C11D—H11D | 108.5 |
| O3B—C12B—C11B | 112.6 (3) | O3D—C12D—C11D | 113.1 (5) |
| O3B—C12B—C7B | 107.4 (3) | O3D—C12D—C7D | 108.8 (5) |
| C11B—C12B—C7B | 111.2 (3) | C11D—C12D—C7D | 111.5 (4) |
| O3B—C12B—H12B | 108.5 | O3D—C12D—H12D | 107.8 |
| C11B—C12B—H12B | 108.5 | C11D—C12D—H12D | 107.8 |
| C7B—C12B—H12B | 108.5 | C7D—C12D—H12D | 107.8 |
| C8B—C13B—C11B | 106.7 (3) | C11D—C13D—C8D | 107.2 (5) |
| C8B—C13B—H13B | 110.4 | C11D—C13D—H13D | 110.3 |
| C11B—C13B—H13B | 110.4 | C8D—C13D—H13D | 110.3 |
| C8B—C13B—H14B | 110.4 | C11D—C13D—H14D | 110.3 |
| C11B—C13B—H14B | 110.4 | C8D—C13D—H14D | 110.3 |
| H13B—C13B—H14B | 108.6 | H13D—C13D—H14D | 108.5 |
| C8B—O1B—C7B | 115.1 (2) | C7D—O1D—C8D | 113.5 (3) |
| C10B—O2B—C11B | 121.3 (3) | C10D—O2D—C11D | 120.4 (5) |
| C12B—O3B—H31B | 109.5 | C12D—O3D—H31D | 109.5 |
| C6A—C1A—C2A—C3A | 0.0 | C6C—C1C—C2C—C3C | 0.0 |
| C1A—C2A—C3A—C4A | 0.0 | C1C—C2C—C3C—C4C | 0.0 |
| C2A—C3A—C4A—C5A | 0.0 | C2C—C3C—C4C—C5C | 0.0 |
| C3A—C4A—C5A—C6A | 0.0 | C3C—C4C—C5C—C6C | 0.0 |
| C4A—C5A—C6A—C1A | 0.0 | C4C—C5C—C6C—C1C | 0.0 |
| C4A—C5A—C6A—C7A | 178.0 | C4C—C5C—C6C—C7C | −176.3 |
| C2A—C1A—C6A—C5A | 0.0 | C2C—C1C—C6C—C5C | 0.0 |
| C2A—C1A—C6A—C7A | −178.0 | C2C—C1C—C6C—C7C | 176.4 |
| C5A—C6A—C7A—O1A | 53.97 (18) | C5C—C6C—C7C—O1C | 64.06 (15) |
| C1A—C6A—C7A—O1A | −127.99 (18) | C1C—C6C—C7C—O1C | −112.31 (15) |
| C5A—C6A—C7A—C12A | −67.9 (3) | C5C—C6C—C7C—C12C | −58.27 (18) |
| C1A—C6A—C7A—C12A | 110.2 (3) | C1C—C6C—C7C—C12C | 125.37 (18) |
| O1A—C8A—C9A—C10A | 83.1 (6) | O1C—C8C—C9C—C10C | 85.5 (4) |
| C13A—C8A—C9A—C10A | −39.7 (6) | C13C—C8C—C9C—C10C | −38.2 (4) |
| C8A—C9A—C10A—O4A | −168.4 (5) | C8C—C9C—C10C—O4C | −174.7 (4) |
| C8A—C9A—C10A—O2A | 15.7 (7) | C8C—C9C—C10C—O2C | 7.3 (5) |
| O2A—C11A—C12A—O3A | −52.2 (7) | O2C—C11C—C12C—O3C | −55.9 (4) |
| C13A—C11A—C12A—O3A | −174.8 (6) | C13C—C11C—C12C—O3C | −179.2 (3) |
| O2A—C11A—C12A—C7A | 67.6 (6) | O2C—C11C—C12C—C7C | 65.4 (3) |
| C13A—C11A—C12A—C7A | −55.0 (7) | C13C—C11C—C12C—C7C | −57.9 (4) |
| O1A—C7A—C12A—O3A | 173.6 (4) | O1C—C7C—C12C—O3C | 176.8 (3) |
| C6A—C7A—C12A—O3A | −66.1 (4) | C6C—C7C—C12C—O3C | −63.8 (3) |
| O1A—C7A—C12A—C11A | 51.2 (6) | O1C—C7C—C12C—C11C | 52.3 (3) |
| C6A—C7A—C12A—C11A | 171.6 (4) | C6C—C7C—C12C—C11C | 171.7 (2) |
| O2A—C11A—C13A—C8A | −63.8 (6) | O2C—C11C—C13C—C8C | −62.5 (4) |
| C12A—C11A—C13A—C8A | 58.0 (7) | C12C—C11C—C13C—C8C | 60.3 (4) |
| O1A—C8A—C13A—C11A | −60.5 (6) | O1C—C8C—C13C—C11C | −59.5 (4) |
| C9A—C8A—C13A—C11A | 62.7 (5) | C9C—C8C—C13C—C11C | 64.7 (4) |
| C6A—C7A—O1A—C8A | −178.3 (3) | C6C—C7C—O1C—C8C | −177.6 (2) |
| C12A—C7A—O1A—C8A | −54.8 (5) | C12C—C7C—O1C—C8C | −53.7 (4) |
| C13A—C8A—O1A—C7A | 61.4 (5) | C13C—C8C—O1C—C7C | 58.6 (4) |
| C9A—C8A—O1A—C7A | −59.6 (5) | C9C—C8C—O1C—C7C | −63.2 (4) |
| O4A—C10A—O2A—C11A | 168.2 (5) | O4C—C10C—O2C—C11C | 177.9 (4) |
| C9A—C10A—O2A—C11A | −15.7 (7) | C9C—C10C—O2C—C11C | −4.0 (5) |
| C13A—C11A—O2A—C10A | 40.4 (7) | C13C—C11C—O2C—C10C | 32.5 (5) |
| C12A—C11A—O2A—C10A | −82.0 (6) | C12C—C11C—O2C—C10C | −90.5 (4) |
| C6B—C1B—C2B—C3B | 0.0 | C6D—C1D—C2D—C3D | 0.0 |
| C1B—C2B—C3B—C4B | 0.0 | C1D—C2D—C3D—C4D | 0.0 |
| C2B—C3B—C4B—C5B | 0.0 | C2D—C3D—C4D—C5D | 0.0 |
| C3B—C4B—C5B—C6B | 0.0 | C3D—C4D—C5D—C6D | 0.0 |
| C4B—C5B—C6B—C1B | 0.0 | C4D—C5D—C6D—C1D | 0.0 |
| C4B—C5B—C6B—C7B | 178.2 | C4D—C5D—C6D—C7D | 178.5 |
| C2B—C1B—C6B—C5B | 0.0 | C2D—C1D—C6D—C5D | 0.0 |
| C2B—C1B—C6B—C7B | −178.2 | C2D—C1D—C6D—C7D | −178.5 |
| C5B—C6B—C7B—O1B | −114.19 (15) | C5D—C6D—C7D—O1D | −109.66 (19) |
| C1B—C6B—C7B—O1B | 64.00 (15) | C1D—C6D—C7D—O1D | 68.87 (19) |
| C5B—C6B—C7B—C12B | 125.02 (18) | C5D—C6D—C7D—C12D | 126.6 (3) |
| C1B—C6B—C7B—C12B | −56.79 (18) | C1D—C6D—C7D—C12D | −54.8 (3) |
| O1B—C8B—C9B—C10B | 84.9 (4) | O1D—C8D—C9D—C10D | 84.3 (7) |
| C13B—C8B—C9B—C10B | −37.7 (4) | C13D—C8D—C9D—C10D | −38.3 (7) |
| C8B—C9B—C10B—O4B | −173.4 (4) | C8D—C9D—C10D—O4D | −168.7 (5) |
| C8B—C9B—C10B—O2B | 8.1 (5) | C8D—C9D—C10D—O2D | 15.2 (8) |
| O2B—C11B—C12B—O3B | −55.5 (4) | O2D—C11D—C12D—O3D | −53.5 (7) |
| C13B—C11B—C12B—O3B | −177.9 (3) | C13D—C11D—C12D—O3D | −176.2 (6) |
| O2B—C11B—C12B—C7B | 65.1 (3) | O2D—C11D—C12D—C7D | 69.5 (7) |
| C13B—C11B—C12B—C7B | −57.3 (4) | C13D—C11D—C12D—C7D | −53.2 (8) |
| O1B—C7B—C12B—O3B | 175.2 (3) | O1D—C7D—C12D—O3D | 174.4 (4) |
| C6B—C7B—C12B—O3B | −66.6 (3) | C6D—C7D—C12D—O3D | −63.9 (5) |
| O1B—C7B—C12B—C11B | 51.5 (3) | O1D—C7D—C12D—C11D | 49.0 (6) |
| C6B—C7B—C12B—C11B | 169.8 (2) | C6D—C7D—C12D—C11D | 170.7 (4) |
| O1B—C8B—C13B—C11B | −60.5 (4) | O2D—C11D—C13D—C8D | −63.2 (6) |
| C9B—C8B—C13B—C11B | 63.4 (4) | C12D—C11D—C13D—C8D | 58.5 (7) |
| O2B—C11B—C13B—C8B | −61.7 (4) | O1D—C8D—C13D—C11D | −61.7 (6) |
| C12B—C11B—C13B—C8B | 60.3 (4) | C9D—C8D—C13D—C11D | 62.2 (6) |
| C9B—C8B—O1B—C7B | −62.2 (4) | C6D—C7D—O1D—C8D | −179.7 (4) |
| C13B—C8B—O1B—C7B | 59.1 (4) | C12D—C7D—O1D—C8D | −54.0 (5) |
| C6B—C7B—O1B—C8B | −175.7 (2) | C13D—C8D—O1D—C7D | 61.4 (6) |
| C12B—C7B—O1B—C8B | −53.1 (4) | C9D—C8D—O1D—C7D | −60.8 (6) |
| O4B—C10B—O2B—C11B | 176.2 (4) | O4D—C10D—O2D—C11D | 167.5 (5) |
| C9B—C10B—O2B—C11B | −5.2 (5) | C9D—C10D—O2D—C11D | −16.2 (7) |
| C12B—C11B—O2B—C10B | −88.9 (4) | C13D—C11D—O2D—C10D | 40.8 (7) |
| C13B—C11B—O2B—C10B | 32.7 (5) | C12D—C11D—O2D—C10D | −82.3 (6) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3B—H31B···O4C | 0.82 | 1.97 | 2.783 (4) | 173 |
| O3C—H31C···O4Bi | 0.82 | 1.97 | 2.784 (4) | 176 |
| O3D—H31D···O3Cii | 0.82 | 2.40 | 3.185 (7) | 161 |
| Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z−1. |
