Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012036/wn6254sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012036/wn6254Isup2.hkl |
CCDC reference: 242342
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C15H22O2 | F(000) = 1024 |
Mr = 234.33 | Dx = 1.078 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 933 reflections |
a = 11.820 (3) Å | θ = 2.6–27.8° |
b = 10.175 (3) Å | µ = 0.07 mm−1 |
c = 24.169 (7) Å | T = 293 K |
β = 96.512 (4)° | Block, yellow |
V = 2887.9 (13) Å3 | 0.50 × 0.40 × 0.30 mm |
Z = 8 |
Bruker SMART APEX CCD area-detector diffractometer | 5071 independent reflections |
Radiation source: fine-focus sealed tube | 3241 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −14→13 |
Tmin = 0.968, Tmax = 0.979 | k = −12→5 |
13667 measured reflections | l = −28→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0999P)2] where P = (Fo2 + 2Fc2)/3 |
5071 reflections | (Δ/σ)max < 0.001 |
381 parameters | Δρmax = 0.17 e Å−3 |
126 restraints | Δρmin = −0.20 e Å−3 |
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 | Occ. (<1) | |
C1 | 1.08861 (13) | 0.56643 (17) | 0.19344 (6) | 0.0533 (4) | |
C2 | 1.02297 (13) | 0.47358 (16) | 0.16159 (7) | 0.0520 (4) | |
C3 | 0.94189 (13) | 0.51411 (16) | 0.11796 (7) | 0.0490 (4) | |
C4 | 0.93167 (13) | 0.64814 (16) | 0.10963 (6) | 0.0509 (4) | |
H4A | 0.8784 | 0.6768 | 0.0809 | 0.061* | |
C5 | 0.99467 (13) | 0.74411 (16) | 0.14078 (6) | 0.0511 (4) | |
C6 | 1.07390 (14) | 0.69982 (17) | 0.18295 (7) | 0.0549 (4) | |
H6A | 1.1181 | 0.7602 | 0.2047 | 0.066* | |
C7 | 1.17425 (15) | 0.5247 (2) | 0.23785 (8) | 0.0698 (5) | |
H7A | 1.2148 | 0.5902 | 0.2583 | 0.084* | |
C8 | 0.97608 (15) | 0.89020 (17) | 0.12796 (7) | 0.0598 (5) | |
C9 | 1.0498 (4) | 0.9785 (3) | 0.16696 (17) | 0.1046 (14) | 0.724 (4) |
H9A | 1.0343 | 0.9628 | 0.2045 | 0.157* | 0.724 (4) |
H9B | 1.0336 | 1.0687 | 0.1574 | 0.157* | 0.724 (4) |
H9C | 1.1285 | 0.9604 | 0.1639 | 0.157* | 0.724 (4) |
C10 | 1.0040 (3) | 0.9171 (3) | 0.06776 (13) | 0.0907 (11) | 0.724 (4) |
H10A | 0.9519 | 0.8691 | 0.0418 | 0.136* | 0.724 (4) |
H10B | 1.0805 | 0.8893 | 0.0643 | 0.136* | 0.724 (4) |
H10C | 0.9969 | 1.0094 | 0.0600 | 0.136* | 0.724 (4) |
C11 | 0.8503 (3) | 0.9247 (3) | 0.1294 (2) | 0.0997 (12) | 0.724 (4) |
H11A | 0.8303 | 0.9124 | 0.1664 | 0.150* | 0.724 (4) |
H11B | 0.8041 | 0.8686 | 0.1041 | 0.150* | 0.724 (4) |
H11C | 0.8378 | 1.0147 | 0.1184 | 0.150* | 0.724 (4) |
C12 | 0.86921 (14) | 0.41357 (17) | 0.08207 (7) | 0.0587 (5) | |
C13 | 0.94646 (19) | 0.3210 (2) | 0.05301 (9) | 0.0832 (6) | |
H13A | 0.9006 | 0.2574 | 0.0314 | 0.125* | |
H13B | 0.9978 | 0.2767 | 0.0805 | 0.125* | |
H13C | 0.9893 | 0.3711 | 0.0289 | 0.125* | |
C14 | 0.78971 (18) | 0.4807 (2) | 0.03656 (8) | 0.0801 (6) | |
H14A | 0.7469 | 0.4154 | 0.0145 | 0.120* | |
H14B | 0.8338 | 0.5315 | 0.0133 | 0.120* | |
H14C | 0.7384 | 0.5376 | 0.0533 | 0.120* | |
C15 | 0.79614 (17) | 0.3350 (2) | 0.11852 (9) | 0.0796 (6) | |
H15A | 0.7535 | 0.2699 | 0.0962 | 0.119* | |
H15B | 0.7446 | 0.3932 | 0.1344 | 0.119* | |
H15C | 0.8444 | 0.2926 | 0.1478 | 0.119* | |
C16 | 0.58975 (13) | 1.05339 (17) | 0.20125 (6) | 0.0522 (4) | |
C17 | 0.52557 (13) | 1.14762 (16) | 0.16938 (7) | 0.0522 (4) | |
C18 | 0.44494 (13) | 1.10814 (17) | 0.12548 (7) | 0.0547 (4) | |
C19 | 0.43112 (14) | 0.97412 (17) | 0.11782 (7) | 0.0554 (4) | |
H19A | 0.3772 | 0.9465 | 0.0892 | 0.066* | |
C20 | 0.49135 (13) | 0.87693 (17) | 0.14949 (6) | 0.0523 (4) | |
C21 | 0.57269 (14) | 0.92023 (17) | 0.19113 (7) | 0.0543 (4) | |
H21A | 0.6166 | 0.8592 | 0.2127 | 0.065* | |
C22 | 0.67701 (15) | 1.0944 (2) | 0.24484 (7) | 0.0700 (5) | |
H22A | 0.7175 | 1.0284 | 0.2650 | 0.084* | |
C23 | 0.47284 (15) | 0.73051 (18) | 0.13781 (7) | 0.0623 (5) | |
C24 | 0.5780 (3) | 0.6760 (3) | 0.11408 (16) | 0.0932 (12) | 0.750 (5) |
H24A | 0.6436 | 0.6866 | 0.1410 | 0.140* | 0.750 (5) |
H24B | 0.5895 | 0.7228 | 0.0807 | 0.140* | 0.750 (5) |
H24C | 0.5669 | 0.5844 | 0.1057 | 0.140* | 0.750 (5) |
C25 | 0.4617 (4) | 0.6566 (3) | 0.19257 (14) | 0.0966 (12) | 0.750 (5) |
H25A | 0.5275 | 0.6737 | 0.2187 | 0.145* | 0.750 (5) |
H25B | 0.4559 | 0.5639 | 0.1853 | 0.145* | 0.750 (5) |
H25C | 0.3946 | 0.6860 | 0.2079 | 0.145* | 0.750 (5) |
C26 | 0.3682 (3) | 0.7020 (4) | 0.09796 (19) | 0.1014 (14) | 0.750 (5) |
H26A | 0.3756 | 0.7426 | 0.0627 | 0.152* | 0.750 (5) |
H26B | 0.3023 | 0.7366 | 0.1128 | 0.152* | 0.750 (5) |
H26C | 0.3599 | 0.6088 | 0.0931 | 0.152* | 0.750 (5) |
C27 | 0.37622 (16) | 1.20964 (19) | 0.08827 (8) | 0.0718 (6) | |
C28 | 0.4580 (2) | 1.3000 (2) | 0.06132 (9) | 0.0932 (7) | |
H28A | 0.4151 | 1.3603 | 0.0366 | 0.140* | |
H28B | 0.5065 | 1.2480 | 0.0407 | 0.140* | |
H28C | 0.5037 | 1.3483 | 0.0898 | 0.140* | |
C29 | 0.3000 (2) | 1.2890 (2) | 0.12286 (11) | 0.1026 (8) | |
H29A | 0.2468 | 1.2313 | 0.1377 | 0.154* | |
H29B | 0.2594 | 1.3541 | 0.0997 | 0.154* | |
H29C | 0.3461 | 1.3316 | 0.1529 | 0.154* | |
C30 | 0.3003 (2) | 1.1428 (2) | 0.04090 (10) | 0.1076 (9) | |
H30A | 0.2444 | 1.0896 | 0.0562 | 0.161* | |
H30B | 0.3463 | 1.0884 | 0.0199 | 0.161* | |
H30C | 0.2628 | 1.2086 | 0.0169 | 0.161* | |
C9' | 0.9575 (12) | 0.9628 (8) | 0.1834 (4) | 0.096 (3) | 0.276 (4) |
H9'A | 0.8877 | 0.9332 | 0.1961 | 0.144* | 0.276 (4) |
H9'B | 0.9534 | 1.0559 | 0.1769 | 0.144* | 0.276 (4) |
H9'C | 1.0199 | 0.9439 | 0.2112 | 0.144* | 0.276 (4) |
C10' | 1.0859 (8) | 0.9444 (8) | 0.1093 (4) | 0.097 (3) | 0.276 (4) |
H10D | 1.1461 | 0.9376 | 0.1394 | 0.145* | 0.276 (4) |
H10E | 1.0752 | 1.0349 | 0.0988 | 0.145* | 0.276 (4) |
H10F | 1.1057 | 0.8947 | 0.0781 | 0.145* | 0.276 (4) |
C11' | 0.8824 (8) | 0.9193 (8) | 0.0834 (5) | 0.093 (3) | 0.276 (4) |
H11D | 0.8115 | 0.8897 | 0.0948 | 0.139* | 0.276 (4) |
H11E | 0.8964 | 0.8748 | 0.0499 | 0.139* | 0.276 (4) |
H11F | 0.8788 | 1.0123 | 0.0768 | 0.139* | 0.276 (4) |
C24' | 0.5018 (10) | 0.7040 (10) | 0.0759 (4) | 0.095 (3) | 0.250 (5) |
H24D | 0.5713 | 0.7482 | 0.0702 | 0.142* | 0.250 (5) |
H24E | 0.4410 | 0.7364 | 0.0498 | 0.142* | 0.250 (5) |
H24F | 0.5106 | 0.6112 | 0.0704 | 0.142* | 0.250 (5) |
C25' | 0.5429 (13) | 0.6412 (10) | 0.1737 (6) | 0.106 (3) | 0.250 (5) |
H25D | 0.6213 | 0.6523 | 0.1678 | 0.159* | 0.250 (5) |
H25E | 0.5199 | 0.5523 | 0.1651 | 0.159* | 0.250 (5) |
H25F | 0.5339 | 0.6597 | 0.2119 | 0.159* | 0.250 (5) |
C26' | 0.3444 (10) | 0.7010 (11) | 0.1366 (6) | 0.096 (3) | 0.250 (5) |
H26D | 0.3231 | 0.7063 | 0.1737 | 0.143* | 0.250 (5) |
H26E | 0.3288 | 0.6143 | 0.1221 | 0.143* | 0.250 (5) |
H26F | 0.3016 | 0.7642 | 0.1133 | 0.143* | 0.250 (5) |
O1 | 1.19740 (12) | 0.41124 (17) | 0.25056 (6) | 0.0884 (5) | |
O2 | 1.03654 (11) | 0.34378 (12) | 0.17310 (6) | 0.0719 (4) | |
H2A | 1.0894 | 0.3169 | 0.2023 | 0.108* | |
O3 | 0.70205 (12) | 1.20737 (16) | 0.25740 (6) | 0.0901 (5) | |
O4 | 0.54056 (11) | 1.27718 (12) | 0.18079 (5) | 0.0727 (4) | |
H4B | 0.5939 | 1.3034 | 0.2100 | 0.109* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0467 (9) | 0.0578 (11) | 0.0547 (9) | 0.0006 (8) | 0.0022 (7) | 0.0066 (8) |
C2 | 0.0488 (9) | 0.0451 (10) | 0.0623 (10) | 0.0053 (8) | 0.0073 (7) | 0.0092 (8) |
C3 | 0.0467 (9) | 0.0417 (10) | 0.0581 (9) | 0.0009 (7) | 0.0043 (7) | −0.0011 (7) |
C4 | 0.0498 (9) | 0.0457 (10) | 0.0551 (9) | 0.0022 (7) | −0.0029 (7) | 0.0014 (7) |
C5 | 0.0534 (9) | 0.0435 (10) | 0.0554 (9) | −0.0020 (8) | 0.0017 (7) | 0.0002 (7) |
C6 | 0.0534 (10) | 0.0539 (11) | 0.0559 (9) | −0.0054 (8) | −0.0005 (7) | −0.0007 (8) |
C7 | 0.0587 (11) | 0.0797 (15) | 0.0681 (11) | 0.0031 (10) | −0.0046 (9) | 0.0138 (10) |
C8 | 0.0683 (11) | 0.0425 (10) | 0.0662 (10) | −0.0014 (8) | −0.0025 (8) | 0.0009 (8) |
C9 | 0.141 (3) | 0.0478 (18) | 0.114 (3) | −0.011 (2) | −0.033 (3) | −0.0095 (18) |
C10 | 0.129 (3) | 0.0560 (19) | 0.087 (2) | −0.0085 (18) | 0.0137 (19) | 0.0108 (15) |
C11 | 0.091 (2) | 0.0552 (19) | 0.155 (4) | 0.0204 (16) | 0.024 (2) | 0.014 (2) |
C12 | 0.0589 (10) | 0.0434 (10) | 0.0721 (11) | −0.0021 (8) | −0.0006 (8) | −0.0066 (8) |
C13 | 0.0941 (15) | 0.0603 (13) | 0.0948 (15) | 0.0046 (11) | 0.0082 (11) | −0.0210 (11) |
C14 | 0.0851 (14) | 0.0625 (13) | 0.0848 (13) | −0.0053 (11) | −0.0239 (11) | −0.0131 (10) |
C15 | 0.0678 (12) | 0.0631 (13) | 0.1064 (15) | −0.0160 (10) | 0.0039 (11) | −0.0016 (11) |
C16 | 0.0480 (9) | 0.0578 (11) | 0.0499 (9) | −0.0039 (8) | 0.0013 (7) | −0.0022 (8) |
C17 | 0.0513 (9) | 0.0459 (10) | 0.0592 (9) | −0.0079 (8) | 0.0052 (7) | −0.0057 (8) |
C18 | 0.0492 (9) | 0.0503 (10) | 0.0627 (10) | −0.0029 (8) | −0.0016 (7) | 0.0067 (8) |
C19 | 0.0536 (10) | 0.0545 (11) | 0.0553 (9) | −0.0063 (8) | −0.0064 (7) | −0.0012 (8) |
C20 | 0.0516 (9) | 0.0501 (10) | 0.0542 (9) | −0.0014 (8) | 0.0024 (7) | −0.0023 (8) |
C21 | 0.0526 (9) | 0.0537 (11) | 0.0551 (9) | 0.0043 (8) | 0.0001 (7) | 0.0022 (8) |
C22 | 0.0670 (11) | 0.0752 (14) | 0.0639 (11) | −0.0067 (11) | −0.0096 (9) | −0.0056 (10) |
C23 | 0.0662 (11) | 0.0484 (11) | 0.0711 (11) | −0.0023 (9) | 0.0023 (9) | −0.0052 (9) |
C24 | 0.101 (2) | 0.066 (2) | 0.115 (3) | 0.0034 (17) | 0.022 (2) | −0.0256 (19) |
C25 | 0.151 (4) | 0.0518 (18) | 0.089 (2) | −0.021 (2) | 0.019 (2) | 0.0038 (15) |
C26 | 0.107 (3) | 0.060 (2) | 0.127 (3) | −0.0163 (19) | −0.031 (3) | −0.014 (2) |
C27 | 0.0659 (12) | 0.0558 (12) | 0.0878 (13) | −0.0044 (9) | −0.0163 (10) | 0.0166 (10) |
C28 | 0.0971 (16) | 0.0778 (16) | 0.0992 (16) | −0.0110 (13) | −0.0129 (12) | 0.0332 (13) |
C29 | 0.0770 (14) | 0.0794 (17) | 0.149 (2) | 0.0219 (13) | 0.0010 (14) | 0.0192 (15) |
C30 | 0.1063 (17) | 0.0823 (17) | 0.1180 (18) | −0.0140 (14) | −0.0577 (15) | 0.0314 (14) |
C9' | 0.149 (8) | 0.047 (4) | 0.091 (5) | 0.020 (5) | 0.012 (5) | 0.000 (4) |
C10' | 0.112 (6) | 0.056 (5) | 0.122 (6) | −0.008 (4) | 0.014 (5) | 0.022 (4) |
C11' | 0.101 (6) | 0.052 (4) | 0.118 (6) | −0.003 (4) | −0.019 (5) | 0.013 (4) |
C24' | 0.107 (7) | 0.081 (6) | 0.099 (6) | 0.000 (5) | 0.017 (5) | −0.017 (5) |
C25' | 0.133 (7) | 0.057 (5) | 0.121 (7) | −0.009 (6) | −0.013 (6) | 0.001 (5) |
C26' | 0.099 (6) | 0.058 (5) | 0.131 (8) | −0.022 (4) | 0.016 (7) | −0.020 (6) |
O1 | 0.0769 (9) | 0.0895 (12) | 0.0934 (10) | 0.0125 (8) | −0.0144 (7) | 0.0302 (9) |
O2 | 0.0722 (8) | 0.0485 (8) | 0.0914 (9) | 0.0072 (6) | −0.0060 (7) | 0.0162 (6) |
O3 | 0.0902 (10) | 0.0882 (12) | 0.0858 (10) | −0.0215 (8) | −0.0167 (8) | −0.0213 (8) |
O4 | 0.0766 (8) | 0.0500 (8) | 0.0880 (9) | −0.0110 (6) | −0.0060 (6) | −0.0088 (6) |
C1—C6 | 1.388 (2) | C20—C23 | 1.527 (2) |
C1—C2 | 1.397 (2) | C21—H21A | 0.9300 |
C1—C7 | 1.453 (2) | C22—O3 | 1.217 (2) |
C2—O2 | 1.3555 (19) | C22—H22A | 0.9300 |
C2—C3 | 1.404 (2) | C23—C25' | 1.450 (11) |
C3—C4 | 1.382 (2) | C23—C26 | 1.507 (4) |
C3—C12 | 1.539 (2) | C23—C24 | 1.531 (3) |
C4—C5 | 1.395 (2) | C23—C25 | 1.541 (4) |
C4—H4A | 0.9300 | C23—C26' | 1.544 (11) |
C5—C6 | 1.379 (2) | C23—C24' | 1.596 (10) |
C5—C8 | 1.529 (2) | C24—H24A | 0.9600 |
C6—H6A | 0.9300 | C24—H24B | 0.9600 |
C7—O1 | 1.218 (2) | C24—H24C | 0.9600 |
C7—H7A | 0.9300 | C25—H25A | 0.9600 |
C8—C11' | 1.484 (8) | C25—H25B | 0.9600 |
C8—C9 | 1.506 (4) | C25—H25C | 0.9600 |
C8—C10' | 1.525 (9) | C26—H26A | 0.9600 |
C8—C11 | 1.531 (4) | C26—H26B | 0.9600 |
C8—C10 | 1.552 (3) | C26—H26C | 0.9600 |
C8—C9' | 1.567 (9) | C27—C29 | 1.527 (3) |
C9—H9A | 0.9600 | C27—C30 | 1.531 (3) |
C9—H9B | 0.9600 | C27—C28 | 1.532 (3) |
C9—H9C | 0.9600 | C28—H28A | 0.9600 |
C10—H10A | 0.9600 | C28—H28B | 0.9600 |
C10—H10B | 0.9600 | C28—H28C | 0.9600 |
C10—H10C | 0.9600 | C29—H29A | 0.9600 |
C11—H11A | 0.9600 | C29—H29B | 0.9600 |
C11—H11B | 0.9600 | C29—H29C | 0.9600 |
C11—H11C | 0.9600 | C30—H30A | 0.9600 |
C12—C14 | 1.525 (3) | C30—H30B | 0.9600 |
C12—C15 | 1.528 (3) | C30—H30C | 0.9600 |
C12—C13 | 1.536 (3) | C9'—H9'A | 0.9600 |
C13—H13A | 0.9600 | C9'—H9'B | 0.9600 |
C13—H13B | 0.9600 | C9'—H9'C | 0.9600 |
C13—H13C | 0.9600 | C10'—H10D | 0.9600 |
C14—H14A | 0.9600 | C10'—H10E | 0.9600 |
C14—H14B | 0.9600 | C10'—H10F | 0.9600 |
C14—H14C | 0.9600 | C11'—H11D | 0.9600 |
C15—H15A | 0.9600 | C11'—H11E | 0.9600 |
C15—H15B | 0.9600 | C11'—H11F | 0.9600 |
C15—H15C | 0.9600 | C24'—H24D | 0.9600 |
C16—C21 | 1.388 (2) | C24'—H24E | 0.9600 |
C16—C17 | 1.398 (2) | C24'—H24F | 0.9600 |
C16—C22 | 1.450 (2) | C25'—H25D | 0.9600 |
C17—O4 | 1.354 (2) | C25'—H25E | 0.9600 |
C17—C18 | 1.402 (2) | C25'—H25F | 0.9600 |
C18—C19 | 1.383 (2) | C26'—H26D | 0.9600 |
C18—C27 | 1.539 (2) | C26'—H26E | 0.9600 |
C19—C20 | 1.395 (2) | C26'—H26F | 0.9600 |
C19—H19A | 0.9300 | O2—H2A | 0.9300 |
C20—C21 | 1.383 (2) | O4—H4B | 0.9300 |
C6—C1—C2 | 120.69 (15) | O3—C22—C16 | 125.87 (19) |
C6—C1—C7 | 118.88 (17) | O3—C22—H22A | 117.1 |
C2—C1—C7 | 120.43 (17) | C16—C22—H22A | 117.1 |
O2—C2—C1 | 120.03 (15) | C25'—C23—C26 | 129.3 (5) |
O2—C2—C3 | 119.68 (15) | C25'—C23—C20 | 116.2 (4) |
C1—C2—C3 | 120.29 (15) | C26—C23—C20 | 113.3 (2) |
C4—C3—C2 | 116.12 (15) | C25'—C23—C24 | 64.1 (7) |
C4—C3—C12 | 122.68 (14) | C26—C23—C24 | 109.5 (2) |
C2—C3—C12 | 121.20 (15) | C20—C23—C24 | 108.49 (17) |
C3—C4—C5 | 125.42 (15) | C26—C23—C25 | 108.1 (2) |
C3—C4—H4A | 117.3 | C20—C23—C25 | 110.00 (17) |
C5—C4—H4A | 117.3 | C24—C23—C25 | 107.3 (2) |
C6—C5—C4 | 116.49 (15) | C25'—C23—C26' | 112.5 (7) |
C6—C5—C8 | 122.49 (15) | C20—C23—C26' | 108.2 (4) |
C4—C5—C8 | 121.02 (14) | C24—C23—C26' | 139.5 (4) |
C5—C6—C1 | 120.99 (15) | C25—C23—C26' | 75.0 (5) |
C5—C6—H6A | 119.5 | C25'—C23—C24' | 106.6 (7) |
C1—C6—H6A | 119.5 | C26—C23—C24' | 67.4 (4) |
O1—C7—C1 | 125.5 (2) | C20—C23—C24' | 107.3 (4) |
O1—C7—H7A | 117.2 | C24—C23—C24' | 47.0 (4) |
C1—C7—H7A | 117.2 | C25—C23—C24' | 140.5 (4) |
C11'—C8—C9 | 131.7 (4) | C26'—C23—C24' | 105.3 (6) |
C11'—C8—C10' | 107.7 (6) | C23—C24—H24A | 109.5 |
C9—C8—C10' | 61.2 (4) | C23—C24—H24B | 109.5 |
C11'—C8—C5 | 114.8 (3) | C23—C24—H24C | 109.5 |
C9—C8—C5 | 113.18 (18) | C23—C25—H25A | 109.5 |
C10'—C8—C5 | 107.7 (3) | C23—C25—H25B | 109.5 |
C11'—C8—C11 | 47.5 (4) | C23—C25—H25C | 109.5 |
C9—C8—C11 | 110.1 (3) | C23—C26—H26A | 109.5 |
C10'—C8—C11 | 141.7 (3) | C23—C26—H26B | 109.5 |
C5—C8—C11 | 109.64 (17) | C23—C26—H26C | 109.5 |
C11'—C8—C10 | 60.4 (5) | C29—C27—C30 | 108.21 (18) |
C9—C8—C10 | 108.2 (2) | C29—C27—C28 | 110.80 (19) |
C10'—C8—C10 | 51.7 (4) | C30—C27—C28 | 107.02 (18) |
C5—C8—C10 | 108.67 (16) | C29—C27—C18 | 109.87 (17) |
C11—C8—C10 | 106.9 (2) | C30—C27—C18 | 111.37 (16) |
C11'—C8—C9' | 111.1 (6) | C28—C27—C18 | 109.53 (15) |
C9—C8—C9' | 46.4 (4) | C27—C28—H28A | 109.5 |
C10'—C8—C9' | 106.8 (6) | C27—C28—H28B | 109.5 |
C5—C8—C9' | 108.4 (3) | H28A—C28—H28B | 109.5 |
C11—C8—C9' | 69.1 (5) | C27—C28—H28C | 109.5 |
C10—C8—C9' | 141.6 (4) | H28A—C28—H28C | 109.5 |
C8—C9—H9A | 109.5 | H28B—C28—H28C | 109.5 |
C8—C9—H9B | 109.5 | C27—C29—H29A | 109.5 |
C8—C9—H9C | 109.5 | C27—C29—H29B | 109.5 |
C8—C10—H10A | 109.5 | H29A—C29—H29B | 109.5 |
C8—C10—H10B | 109.5 | C27—C29—H29C | 109.5 |
C8—C10—H10C | 109.5 | H29A—C29—H29C | 109.5 |
C8—C11—H11A | 109.5 | H29B—C29—H29C | 109.5 |
C8—C11—H11B | 109.5 | C27—C30—H30A | 109.5 |
C8—C11—H11C | 109.5 | C27—C30—H30B | 109.5 |
C14—C12—C15 | 107.93 (15) | H30A—C30—H30B | 109.5 |
C14—C12—C13 | 107.13 (16) | C27—C30—H30C | 109.5 |
C15—C12—C13 | 110.32 (16) | H30A—C30—H30C | 109.5 |
C14—C12—C3 | 111.58 (15) | H30B—C30—H30C | 109.5 |
C15—C12—C3 | 109.81 (14) | C8—C9'—H9'A | 109.5 |
C13—C12—C3 | 110.03 (14) | C8—C9'—H9'B | 109.5 |
C12—C13—H13A | 109.5 | H9'A—C9'—H9'B | 109.5 |
C12—C13—H13B | 109.5 | C8—C9'—H9'C | 109.5 |
H13A—C13—H13B | 109.5 | H9'A—C9'—H9'C | 109.5 |
C12—C13—H13C | 109.5 | H9'B—C9'—H9'C | 109.5 |
H13A—C13—H13C | 109.5 | C8—C10'—H10D | 109.5 |
H13B—C13—H13C | 109.5 | C8—C10'—H10E | 109.5 |
C12—C14—H14A | 109.5 | H10D—C10'—H10E | 109.5 |
C12—C14—H14B | 109.5 | C8—C10'—H10F | 109.5 |
H14A—C14—H14B | 109.5 | H10D—C10'—H10F | 109.5 |
C12—C14—H14C | 109.5 | H10E—C10'—H10F | 109.5 |
H14A—C14—H14C | 109.5 | C8—C11'—H11D | 109.5 |
H14B—C14—H14C | 109.5 | C8—C11'—H11E | 109.5 |
C12—C15—H15A | 109.5 | H11D—C11'—H11E | 109.5 |
C12—C15—H15B | 109.5 | C8—C11'—H11F | 109.5 |
H15A—C15—H15B | 109.5 | H11D—C11'—H11F | 109.5 |
C12—C15—H15C | 109.5 | H11E—C11'—H11F | 109.5 |
H15A—C15—H15C | 109.5 | C23—C24'—H24D | 109.5 |
H15B—C15—H15C | 109.5 | C23—C24'—H24E | 109.5 |
C21—C16—C17 | 120.90 (15) | H24D—C24'—H24E | 109.5 |
C21—C16—C22 | 119.10 (17) | C23—C24'—H24F | 109.5 |
C17—C16—C22 | 119.99 (17) | H24D—C24'—H24F | 109.5 |
O4—C17—C16 | 120.33 (14) | H24E—C24'—H24F | 109.5 |
O4—C17—C18 | 119.66 (15) | C23—C25'—H25D | 109.5 |
C16—C17—C18 | 120.01 (15) | C23—C25'—H25E | 109.5 |
C19—C18—C17 | 116.33 (15) | H25D—C25'—H25E | 109.5 |
C19—C18—C27 | 122.45 (15) | C23—C25'—H25F | 109.5 |
C17—C18—C27 | 121.21 (16) | H25D—C25'—H25F | 109.5 |
C18—C19—C20 | 125.45 (15) | H25E—C25'—H25F | 109.5 |
C18—C19—H19A | 117.3 | C23—C26'—H26D | 109.5 |
C20—C19—H19A | 117.3 | C23—C26'—H26E | 109.5 |
C21—C20—C19 | 116.29 (16) | H26D—C26'—H26E | 109.5 |
C21—C20—C23 | 121.23 (15) | C23—C26'—H26F | 109.5 |
C19—C20—C23 | 122.44 (15) | H26D—C26'—H26F | 109.5 |
C20—C21—C16 | 120.97 (16) | H26E—C26'—H26F | 109.5 |
C20—C21—H21A | 119.5 | C2—O2—H2A | 119.8 |
C16—C21—H21A | 119.5 | C17—O4—H4B | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1 | 0.93 | 1.89 | 2.6045 (19) | 132 |
O4—H4B···O3 | 0.93 | 1.89 | 2.6029 (19) | 132 |