Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619012567/fn3321sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012567/fn3321Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619012567/fn3321Isup3.cml |
CCDC reference: 1952577
Data collection: SAINT (Bruker, 2017); cell refinement: APEX3 (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008).
C32H30O3 | Z = 2 |
Mr = 462.56 | F(000) = 492 |
Triclinic, P1 | Dx = 1.248 Mg m−3 |
a = 5.954 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.88 (2) Å | Cell parameters from 539 reflections |
c = 26.30 (7) Å | θ = 2.5–25.1° |
α = 89.56 (7)° | µ = 0.08 mm−1 |
β = 86.85 (6)° | T = 100 K |
γ = 87.68 (6)° | Prism, clear light colourless |
V = 1231 (6) Å3 | 0.38 × 0.12 × 0.08 mm |
Bruker D8 Venture Photon 100 CMOS diffractometer | 5226 independent reflections |
Radiation source: IuS | 4335 reflections with I > 2σ(I) |
No monochromator | Rint = 0.065 |
Detector resolution: 0.79 pixels mm-1 | θmax = 26.8°, θmin = 2.3° |
ω and φ scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −9→9 |
Tmin = 0.702, Tmax = 0.745 | l = −33→33 |
54736 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.6514P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.004 |
5226 reflections | Δρmax = 0.31 e Å−3 |
321 parameters | Δρmin = −0.37 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.11500 (17) | 0.59036 (15) | 0.08376 (5) | 0.0340 (3) | |
O2 | 0.89890 (18) | 0.12003 (15) | 0.13185 (4) | 0.0308 (3) | |
O3 | 0.45100 (16) | 0.67774 (12) | 0.05605 (4) | 0.0195 (2) | |
H3 | 0.582 (3) | 0.637 (2) | 0.0638 (7) | 0.029* | |
C1 | 0.4885 (4) | 0.7109 (3) | 0.40948 (7) | 0.0457 (5) | |
H1 | 0.519064 | 0.713965 | 0.444531 | 0.055* | |
C2 | 0.3032 (4) | 0.6288 (3) | 0.39392 (7) | 0.0517 (5) | |
H2 | 0.207458 | 0.573579 | 0.418337 | 0.062* | |
C3 | 0.2562 (3) | 0.6269 (3) | 0.34244 (6) | 0.0417 (4) | |
H3A | 0.126980 | 0.571509 | 0.332440 | 0.050* | |
C4 | 0.3952 (3) | 0.70461 (18) | 0.30538 (6) | 0.0246 (3) | |
C5 | 0.3504 (2) | 0.69506 (17) | 0.24985 (5) | 0.0210 (3) | |
C6 | 0.1686 (2) | 0.6067 (2) | 0.23274 (6) | 0.0263 (3) | |
H6 | 0.062221 | 0.562051 | 0.257013 | 0.032* | |
C7 | 0.1407 (2) | 0.58299 (19) | 0.18109 (5) | 0.0239 (3) | |
H7 | 0.015440 | 0.523160 | 0.170875 | 0.029* | |
C8 | 0.2937 (2) | 0.64567 (16) | 0.14392 (5) | 0.0167 (3) | |
C9 | 0.2845 (2) | 0.59661 (16) | 0.08728 (5) | 0.0161 (3) | |
C10 | 0.2943 (2) | 0.40066 (17) | 0.07844 (5) | 0.0178 (3) | |
H10A | 0.168629 | 0.352800 | 0.099419 | 0.021* | |
H10B | 0.263033 | 0.381764 | 0.042380 | 0.021* | |
C11 | 0.5107 (2) | 0.29412 (17) | 0.08956 (5) | 0.0179 (3) | |
H11 | 0.642503 | 0.345815 | 0.071028 | 0.021* | |
C12 | 0.5520 (2) | 0.28629 (18) | 0.14674 (5) | 0.0227 (3) | |
H12A | 0.556194 | 0.404252 | 0.159275 | 0.027* | |
H12B | 0.421071 | 0.233764 | 0.164498 | 0.027* | |
C13 | 0.7637 (2) | 0.19030 (17) | 0.16233 (5) | 0.0203 (3) | |
C14 | 0.8094 (2) | 0.19095 (17) | 0.21833 (5) | 0.0205 (3) | |
C15 | 1.0030 (3) | 0.1047 (2) | 0.23466 (6) | 0.0277 (3) | |
H15 | 1.099133 | 0.042518 | 0.210840 | 0.033* | |
C16 | 1.0557 (3) | 0.1095 (2) | 0.28562 (6) | 0.0317 (4) | |
H16 | 1.188292 | 0.050601 | 0.295840 | 0.038* | |
C17 | 0.9184 (3) | 0.19882 (19) | 0.32221 (6) | 0.0260 (3) | |
C18 | 0.9749 (3) | 0.2060 (2) | 0.37702 (6) | 0.0312 (4) | |
C19 | 1.1674 (5) | 0.1275 (3) | 0.39442 (8) | 0.0677 (8) | |
H19 | 1.267952 | 0.066923 | 0.371133 | 0.081* | |
C20 | 1.2177 (5) | 0.1354 (4) | 0.44565 (9) | 0.0771 (9) | |
H20 | 1.352458 | 0.081302 | 0.456481 | 0.092* | |
C21 | 1.0763 (4) | 0.2194 (3) | 0.48023 (8) | 0.0583 (6) | |
H21 | 1.107629 | 0.219650 | 0.515264 | 0.070* | |
C22 | 0.6286 (4) | 0.7882 (3) | 0.37356 (7) | 0.0482 (5) | |
H22 | 0.757280 | 0.843554 | 0.383877 | 0.058* | |
C23 | 0.5821 (3) | 0.7855 (3) | 0.32210 (7) | 0.0401 (4) | |
H23 | 0.679745 | 0.839961 | 0.297900 | 0.048* | |
C24 | 0.0542 (2) | 0.66209 (17) | 0.06869 (5) | 0.0183 (3) | |
C25 | 0.0441 (2) | 0.8097 (2) | 0.03301 (6) | 0.0284 (3) | |
H25A | −0.112203 | 0.833463 | 0.024411 | 0.043* | |
H25B | 0.136554 | 0.783205 | 0.001889 | 0.043* | |
H25C | 0.101259 | 0.909638 | 0.049253 | 0.043* | |
C26 | 0.4818 (3) | 0.11474 (18) | 0.06834 (6) | 0.0250 (3) | |
H26A | 0.618396 | 0.044272 | 0.073303 | 0.038* | |
H26B | 0.455857 | 0.122803 | 0.031916 | 0.038* | |
H26C | 0.352878 | 0.063197 | 0.086331 | 0.038* | |
C27 | 0.8375 (4) | 0.2960 (4) | 0.41242 (8) | 0.0761 (9) | |
H27 | 0.705391 | 0.354151 | 0.401649 | 0.091* | |
C28 | 0.8882 (5) | 0.3034 (5) | 0.46354 (9) | 0.0871 (10) | |
H28 | 0.791574 | 0.367121 | 0.486885 | 0.104* | |
C29 | 0.7243 (3) | 0.2826 (2) | 0.30556 (6) | 0.0375 (4) | |
H29 | 0.627046 | 0.343714 | 0.329411 | 0.045* | |
C30 | 0.6705 (3) | 0.2785 (2) | 0.25466 (6) | 0.0342 (4) | |
H30 | 0.536951 | 0.336240 | 0.244515 | 0.041* | |
C31 | 0.4657 (2) | 0.74429 (18) | 0.16047 (5) | 0.0220 (3) | |
H31 | 0.564737 | 0.796467 | 0.136072 | 0.026* | |
C32 | 0.4939 (3) | 0.76713 (19) | 0.21236 (6) | 0.0257 (3) | |
H32 | 0.613537 | 0.833283 | 0.222460 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0122 (5) | 0.0412 (7) | 0.0490 (7) | −0.0047 (4) | −0.0060 (5) | 0.0163 (5) |
O2 | 0.0241 (5) | 0.0410 (6) | 0.0262 (5) | 0.0097 (5) | 0.0001 (4) | 0.0006 (5) |
O3 | 0.0101 (4) | 0.0255 (5) | 0.0228 (5) | −0.0014 (4) | −0.0014 (4) | 0.0070 (4) |
C1 | 0.0565 (12) | 0.0588 (12) | 0.0227 (8) | 0.0011 (10) | −0.0114 (8) | −0.0046 (8) |
C2 | 0.0602 (13) | 0.0718 (14) | 0.0241 (9) | −0.0169 (11) | −0.0019 (8) | 0.0031 (9) |
C3 | 0.0452 (10) | 0.0569 (12) | 0.0244 (8) | −0.0168 (9) | −0.0029 (7) | −0.0001 (8) |
C4 | 0.0279 (8) | 0.0221 (7) | 0.0235 (7) | 0.0042 (6) | −0.0029 (6) | −0.0031 (6) |
C5 | 0.0225 (7) | 0.0187 (7) | 0.0218 (7) | 0.0028 (5) | −0.0016 (5) | −0.0024 (5) |
C6 | 0.0204 (7) | 0.0348 (8) | 0.0235 (7) | −0.0055 (6) | 0.0035 (6) | 0.0005 (6) |
C7 | 0.0162 (6) | 0.0308 (8) | 0.0252 (7) | −0.0063 (6) | −0.0008 (5) | −0.0007 (6) |
C8 | 0.0134 (6) | 0.0153 (6) | 0.0213 (7) | 0.0023 (5) | −0.0028 (5) | 0.0008 (5) |
C9 | 0.0106 (6) | 0.0185 (6) | 0.0193 (6) | −0.0013 (5) | −0.0018 (5) | 0.0033 (5) |
C10 | 0.0149 (6) | 0.0198 (7) | 0.0191 (6) | −0.0025 (5) | −0.0044 (5) | 0.0006 (5) |
C11 | 0.0161 (6) | 0.0173 (6) | 0.0205 (6) | −0.0005 (5) | −0.0019 (5) | 0.0004 (5) |
C12 | 0.0228 (7) | 0.0233 (7) | 0.0219 (7) | 0.0056 (6) | −0.0049 (5) | −0.0025 (5) |
C13 | 0.0187 (7) | 0.0174 (6) | 0.0248 (7) | −0.0009 (5) | −0.0020 (5) | 0.0021 (5) |
C14 | 0.0203 (7) | 0.0180 (6) | 0.0234 (7) | −0.0009 (5) | −0.0031 (5) | 0.0030 (5) |
C15 | 0.0225 (7) | 0.0324 (8) | 0.0274 (8) | 0.0069 (6) | −0.0011 (6) | 0.0030 (6) |
C16 | 0.0237 (8) | 0.0414 (9) | 0.0297 (8) | 0.0083 (7) | −0.0066 (6) | 0.0049 (7) |
C17 | 0.0283 (8) | 0.0245 (7) | 0.0257 (7) | −0.0021 (6) | −0.0064 (6) | 0.0025 (6) |
C18 | 0.0358 (9) | 0.0333 (8) | 0.0256 (8) | −0.0061 (7) | −0.0081 (7) | 0.0036 (6) |
C19 | 0.0842 (17) | 0.0793 (16) | 0.0392 (11) | 0.0431 (14) | −0.0310 (11) | −0.0160 (11) |
C20 | 0.100 (2) | 0.0869 (18) | 0.0451 (13) | 0.0391 (16) | −0.0419 (13) | −0.0106 (12) |
C21 | 0.0713 (15) | 0.0796 (16) | 0.0265 (9) | −0.0125 (12) | −0.0183 (10) | 0.0046 (10) |
C22 | 0.0480 (11) | 0.0655 (13) | 0.0333 (10) | −0.0129 (10) | −0.0152 (8) | −0.0039 (9) |
C23 | 0.0396 (10) | 0.0530 (11) | 0.0292 (9) | −0.0122 (8) | −0.0074 (7) | 0.0004 (8) |
C24 | 0.0135 (6) | 0.0212 (7) | 0.0207 (6) | 0.0005 (5) | −0.0043 (5) | −0.0026 (5) |
C25 | 0.0192 (7) | 0.0295 (8) | 0.0371 (8) | 0.0002 (6) | −0.0099 (6) | 0.0097 (6) |
C26 | 0.0278 (8) | 0.0194 (7) | 0.0280 (7) | −0.0006 (6) | −0.0036 (6) | −0.0036 (6) |
C27 | 0.0483 (13) | 0.149 (3) | 0.0291 (10) | 0.0287 (15) | −0.0095 (9) | −0.0165 (13) |
C28 | 0.0602 (15) | 0.171 (3) | 0.0293 (11) | 0.0173 (18) | −0.0052 (10) | −0.0208 (15) |
C29 | 0.0417 (10) | 0.0431 (10) | 0.0266 (8) | 0.0186 (8) | −0.0052 (7) | −0.0056 (7) |
C30 | 0.0313 (8) | 0.0418 (9) | 0.0287 (8) | 0.0187 (7) | −0.0077 (7) | −0.0023 (7) |
C31 | 0.0222 (7) | 0.0206 (7) | 0.0236 (7) | −0.0063 (5) | −0.0009 (5) | 0.0017 (5) |
C32 | 0.0279 (8) | 0.0238 (7) | 0.0265 (7) | −0.0087 (6) | −0.0054 (6) | −0.0020 (6) |
O1—C24 | 1.221 (3) | C14—C30 | 1.396 (3) |
O2—C13 | 1.223 (3) | C15—H15 | 0.9500 |
O3—H3 | 0.86 (2) | C15—C16 | 1.394 (4) |
O3—C9 | 1.421 (3) | C16—H16 | 0.9500 |
C1—H1 | 0.9500 | C16—C17 | 1.403 (3) |
C1—C2 | 1.383 (4) | C17—C18 | 1.500 (4) |
C1—C22 | 1.380 (4) | C17—C29 | 1.397 (4) |
C2—H2 | 0.9500 | C18—C19 | 1.379 (4) |
C2—C3 | 1.398 (4) | C18—C27 | 1.385 (4) |
C3—H3A | 0.9500 | C19—H19 | 0.9500 |
C3—C4 | 1.398 (3) | C19—C20 | 1.399 (4) |
C4—C5 | 1.502 (4) | C20—H20 | 0.9500 |
C4—C23 | 1.397 (4) | C20—C21 | 1.361 (4) |
C5—C6 | 1.407 (3) | C21—H21 | 0.9500 |
C5—C32 | 1.401 (3) | C21—C28 | 1.370 (5) |
C6—H6 | 0.9500 | C22—H22 | 0.9500 |
C6—C7 | 1.392 (4) | C22—C23 | 1.397 (4) |
C7—H7 | 0.9500 | C23—H23 | 0.9500 |
C7—C8 | 1.400 (3) | C24—C25 | 1.490 (4) |
C8—C9 | 1.547 (4) | C25—H25A | 0.9800 |
C8—C31 | 1.400 (3) | C25—H25B | 0.9800 |
C9—C10 | 1.561 (5) | C25—H25C | 0.9800 |
C9—C24 | 1.548 (4) | C26—H26A | 0.9800 |
C10—H10A | 0.9900 | C26—H26B | 0.9800 |
C10—H10B | 0.9900 | C26—H26C | 0.9800 |
C10—C11 | 1.549 (4) | C27—H27 | 0.9500 |
C11—H11 | 1.0000 | C27—C28 | 1.396 (4) |
C11—C12 | 1.537 (4) | C28—H28 | 0.9500 |
C11—C26 | 1.543 (4) | C29—H29 | 0.9500 |
C12—H12A | 0.9900 | C29—C30 | 1.395 (4) |
C12—H12B | 0.9900 | C30—H30 | 0.9500 |
C12—C13 | 1.518 (4) | C31—H31 | 0.9500 |
C13—C14 | 1.513 (4) | C31—C32 | 1.398 (4) |
C14—C15 | 1.400 (3) | C32—H32 | 0.9500 |
C9—O3—H3 | 108.4 (12) | C15—C16—H16 | 119.1 |
C2—C1—H1 | 120.3 | C15—C16—C17 | 121.83 (19) |
C22—C1—H1 | 120.3 | C17—C16—H16 | 119.1 |
C22—C1—C2 | 119.3 (2) | C16—C17—C18 | 122.18 (19) |
C1—C2—H2 | 119.8 | C29—C17—C16 | 117.2 (2) |
C1—C2—C3 | 120.32 (19) | C29—C17—C18 | 120.66 (16) |
C3—C2—H2 | 119.8 | C19—C18—C17 | 122.04 (18) |
C2—C3—H3A | 119.3 | C19—C18—C27 | 116.8 (2) |
C4—C3—C2 | 121.4 (2) | C27—C18—C17 | 121.2 (2) |
C4—C3—H3A | 119.3 | C18—C19—H19 | 119.3 |
C3—C4—C5 | 121.27 (19) | C18—C19—C20 | 121.3 (2) |
C3—C4—C23 | 117.1 (2) | C20—C19—H19 | 119.3 |
C23—C4—C5 | 121.62 (15) | C19—C20—H20 | 119.5 |
C6—C5—C4 | 121.72 (14) | C21—C20—C19 | 121.0 (3) |
C32—C5—C4 | 121.56 (19) | C21—C20—H20 | 119.5 |
C32—C5—C6 | 116.7 (2) | C20—C21—H21 | 120.6 |
C5—C6—H6 | 119.2 | C20—C21—C28 | 118.7 (2) |
C7—C6—C5 | 121.62 (14) | C28—C21—H21 | 120.6 |
C7—C6—H6 | 119.2 | C1—C22—H22 | 119.8 |
C6—C7—H7 | 119.4 | C1—C22—C23 | 120.3 (2) |
C6—C7—C8 | 121.24 (19) | C23—C22—H22 | 119.8 |
C8—C7—H7 | 119.4 | C4—C23—H23 | 119.2 |
C7—C8—C9 | 121.34 (17) | C22—C23—C4 | 121.55 (18) |
C7—C8—C31 | 117.4 (2) | C22—C23—H23 | 119.2 |
C31—C8—C9 | 121.08 (13) | O1—C24—C9 | 118.7 (2) |
O3—C9—C8 | 111.96 (16) | O1—C24—C25 | 121.71 (16) |
O3—C9—C10 | 111.28 (15) | C25—C24—C9 | 119.60 (14) |
O3—C9—C24 | 106.2 (2) | C24—C25—H25A | 109.5 |
C8—C9—C10 | 113.34 (12) | C24—C25—H25B | 109.5 |
C8—C9—C24 | 107.83 (13) | C24—C25—H25C | 109.5 |
C24—C9—C10 | 105.72 (13) | H25A—C25—H25B | 109.5 |
C9—C10—H10A | 107.4 | H25A—C25—H25C | 109.5 |
C9—C10—H10B | 107.4 | H25B—C25—H25C | 109.5 |
H10A—C10—H10B | 106.9 | C11—C26—H26A | 109.5 |
C11—C10—C9 | 119.81 (15) | C11—C26—H26B | 109.5 |
C11—C10—H10A | 107.4 | C11—C26—H26C | 109.5 |
C11—C10—H10B | 107.4 | H26A—C26—H26B | 109.5 |
C10—C11—H11 | 109.0 | H26A—C26—H26C | 109.5 |
C12—C11—C10 | 112.14 (12) | H26B—C26—H26C | 109.5 |
C12—C11—H11 | 109.0 | C18—C27—H27 | 119.2 |
C12—C11—C26 | 110.89 (15) | C18—C27—C28 | 121.7 (3) |
C26—C11—C10 | 106.81 (18) | C28—C27—H27 | 119.2 |
C26—C11—H11 | 109.0 | C21—C28—C27 | 120.4 (2) |
C11—C12—H12A | 108.0 | C21—C28—H28 | 119.8 |
C11—C12—H12B | 108.0 | C27—C28—H28 | 119.8 |
H12A—C12—H12B | 107.3 | C17—C29—H29 | 119.3 |
C13—C12—C11 | 117.11 (13) | C30—C29—C17 | 121.35 (16) |
C13—C12—H12A | 108.0 | C30—C29—H29 | 119.3 |
C13—C12—H12B | 108.0 | C14—C30—H30 | 119.4 |
O2—C13—C12 | 123.22 (19) | C29—C30—C14 | 121.2 (2) |
O2—C13—C14 | 119.93 (18) | C29—C30—H30 | 119.4 |
C14—C13—C12 | 116.79 (13) | C8—C31—H31 | 119.5 |
C15—C14—C13 | 119.02 (14) | C32—C31—C8 | 121.00 (14) |
C30—C14—C13 | 122.92 (18) | C32—C31—H31 | 119.5 |
C30—C14—C15 | 118.0 (2) | C5—C32—H32 | 119.1 |
C14—C15—H15 | 119.8 | C31—C32—C5 | 121.75 (19) |
C16—C15—C14 | 120.47 (15) | C31—C32—H32 | 119.1 |
C16—C15—H15 | 119.8 | ||
O2—C13—C14—C15 | −2.5 (2) | C11—C12—C13—C14 | 176.89 (11) |
O2—C13—C14—C30 | 175.47 (15) | C12—C13—C14—C15 | −179.79 (13) |
O3—C9—C10—C11 | 61.0 (2) | C12—C13—C14—C30 | −1.8 (2) |
O3—C9—C24—O1 | 167.99 (13) | C13—C14—C15—C16 | 176.96 (14) |
O3—C9—C24—C25 | −11.86 (17) | C13—C14—C30—C29 | −176.88 (16) |
C1—C2—C3—C4 | 1.0 (3) | C14—C15—C16—C17 | 0.3 (3) |
C1—C22—C23—C4 | −0.4 (3) | C15—C14—C30—C29 | 1.1 (3) |
C2—C1—C22—C23 | 0.8 (3) | C15—C16—C17—C18 | −179.41 (15) |
C2—C3—C4—C5 | 177.02 (17) | C15—C16—C17—C29 | 0.4 (3) |
C2—C3—C4—C23 | −0.5 (3) | C16—C17—C18—C19 | 1.2 (3) |
C3—C4—C5—C6 | −0.5 (2) | C16—C17—C18—C27 | 179.6 (2) |
C3—C4—C5—C32 | −177.54 (15) | C16—C17—C29—C30 | −0.4 (3) |
C3—C4—C23—C22 | 0.2 (3) | C17—C18—C19—C20 | −180.0 (2) |
C4—C5—C6—C7 | −173.26 (14) | C17—C18—C27—C28 | 179.9 (3) |
C4—C5—C32—C31 | 173.58 (13) | C17—C29—C30—C14 | −0.3 (3) |
C5—C4—C23—C22 | −177.31 (17) | C18—C17—C29—C30 | 179.40 (16) |
C5—C6—C7—C8 | 0.3 (2) | C18—C19—C20—C21 | 0.8 (5) |
C6—C5—C32—C31 | −3.6 (2) | C18—C27—C28—C21 | −0.7 (5) |
C6—C7—C8—C9 | 170.52 (13) | C19—C18—C27—C28 | −1.6 (4) |
C6—C7—C8—C31 | −4.8 (2) | C19—C20—C21—C28 | −3.1 (5) |
C7—C8—C9—O3 | 178.49 (12) | C20—C21—C28—C27 | 3.0 (5) |
C7—C8—C9—C10 | −54.6 (2) | C22—C1—C2—C3 | −1.1 (3) |
C7—C8—C9—C24 | 62.0 (2) | C23—C4—C5—C6 | 176.89 (15) |
C7—C8—C31—C32 | 5.2 (2) | C23—C4—C5—C32 | −0.1 (2) |
C8—C9—C10—C11 | −66.22 (17) | C24—C9—C10—C11 | 175.88 (11) |
C8—C9—C24—O1 | −71.8 (2) | C26—C11—C12—C13 | 62.7 (2) |
C8—C9—C24—C25 | 108.3 (2) | C27—C18—C19—C20 | 1.5 (4) |
C8—C31—C32—C5 | −1.0 (2) | C29—C17—C18—C19 | −178.7 (2) |
C9—C8—C31—C32 | −170.23 (13) | C29—C17—C18—C27 | −0.3 (3) |
C9—C10—C11—C12 | 68.05 (17) | C30—C14—C15—C16 | −1.1 (2) |
C9—C10—C11—C26 | −170.27 (12) | C31—C8—C9—O3 | −6.32 (17) |
C10—C9—C24—O1 | 49.7 (2) | C31—C8—C9—C10 | 120.56 (17) |
C10—C9—C24—C25 | −130.17 (19) | C31—C8—C9—C24 | −122.8 (2) |
C10—C11—C12—C13 | −177.99 (11) | C32—C5—C6—C7 | 3.9 (2) |
C11—C12—C13—O2 | −0.3 (2) |