The title compound, C21H18O6·2C3H6O, crystallizes as a clathrate complex that includes two acetone guest molecules in a capsular assembly formed by two 2,3,7,8,12,13-hexahydroxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene molecules. Intermolecular hydrogen-bonding and host-guest interactions define this dimeric clathrate complex, which is also part of a two-dimensional extensively hydrogen-bonded sheet involving the clathrate complex and acetone solvent molecules in the extended crystal packing.
Supporting information
CCDC reference: 643099
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.154
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.651 1.000
Tmin(prime) and Tmax expected: 0.957 0.992
RR(prime) = 0.675
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.134
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2003) and POV-RAY (Cason, 2002); software used to prepare material for publication: local program.
2,3,7,8,12,13-Hexahydroxy-10,15-dihydro-5
H-tribenzo[a,d,g]cyclononene
acetone disolvate
top
Crystal data top
C21H18O6·2C3H6O | Z = 2 |
Mr = 482.51 | F(000) = 512 |
Triclinic, P1 | Dx = 1.372 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6680 (2) Å | Cell parameters from 8798 reflections |
b = 11.0804 (3) Å | θ = 1.0–27.5° |
c = 11.0992 (3) Å | µ = 0.10 mm−1 |
α = 79.924 (1)° | T = 150 K |
β = 65.001 (1)° | Block, colourless |
γ = 82.157 (2)° | 0.43 × 0.23 × 0.08 mm |
V = 1167.86 (5) Å3 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 5340 independent reflections |
Radiation source: fine-focus sealed tube | 2750 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.134 |
φ and ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −13→13 |
Tmin = 0.651, Tmax = 1.000 | k = −14→14 |
23276 measured reflections | l = −14→14 |
Refinement top
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3 |
5340 reflections | (Δ/σ)max < 0.001 |
326 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−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 | |
C1 | 0.6400 (2) | 0.6928 (2) | 0.0359 (2) | 0.0266 (5) | |
C2 | 0.5430 (2) | 0.6033 (2) | 0.0942 (2) | 0.0286 (5) | |
H2 | 0.4521 | 0.6239 | 0.0979 | 0.034* | |
C3 | 0.5739 (2) | 0.4869 (2) | 0.1463 (2) | 0.0281 (5) | |
C4 | 0.7079 (2) | 0.4548 (2) | 0.1395 (2) | 0.0277 (5) | |
C5 | 0.8050 (2) | 0.5412 (2) | 0.0793 (2) | 0.0281 (5) | |
H5 | 0.8962 | 0.5190 | 0.0740 | 0.034* | |
C6 | 0.7760 (2) | 0.6595 (2) | 0.0258 (2) | 0.0270 (5) | |
C7 | 0.8920 (2) | 0.7481 (2) | −0.0342 (2) | 0.0287 (5) | |
H7A | 0.9797 | 0.7029 | −0.0870 | 0.034* | |
H7B | 0.8705 | 0.8141 | −0.0967 | 0.034* | |
C8 | 0.9138 (2) | 0.8066 (2) | 0.0690 (2) | 0.0266 (5) | |
C9 | 0.9975 (2) | 0.7419 (2) | 0.1315 (2) | 0.0279 (5) | |
H9 | 1.0403 | 0.6638 | 0.1068 | 0.034* | |
C10 | 1.0196 (2) | 0.7887 (2) | 0.2279 (2) | 0.0275 (5) | |
C11 | 0.9608 (2) | 0.9050 (2) | 0.2616 (2) | 0.0275 (5) | |
C12 | 0.8808 (2) | 0.9705 (2) | 0.1983 (2) | 0.0271 (5) | |
H12 | 0.8426 | 1.0505 | 0.2198 | 0.032* | |
C13 | 0.8543 (2) | 0.9227 (2) | 0.1035 (2) | 0.0263 (5) | |
C14 | 0.7566 (2) | 0.9989 (2) | 0.0472 (2) | 0.0275 (5) | |
H14A | 0.7700 | 1.0873 | 0.0381 | 0.033* | |
H14B | 0.7785 | 0.9780 | −0.0430 | 0.033* | |
C15 | 0.6071 (2) | 0.9750 (2) | 0.1382 (2) | 0.0259 (5) | |
C16 | 0.5469 (2) | 1.0316 (2) | 0.2543 (2) | 0.0266 (5) | |
H16 | 0.5991 | 1.0864 | 0.2685 | 0.032* | |
C17 | 0.4150 (2) | 1.0115 (2) | 0.3494 (2) | 0.0260 (5) | |
C18 | 0.3369 (2) | 0.9337 (2) | 0.3267 (2) | 0.0258 (5) | |
C19 | 0.3931 (2) | 0.8779 (2) | 0.2117 (2) | 0.0279 (5) | |
H19 | 0.3386 | 0.8261 | 0.1966 | 0.034* | |
C20 | 0.5293 (2) | 0.8957 (2) | 0.1161 (2) | 0.0261 (5) | |
C21 | 0.5877 (2) | 0.8221 (2) | −0.0019 (2) | 0.0287 (5) | |
H21A | 0.5147 | 0.8176 | −0.0335 | 0.034* | |
H21B | 0.6649 | 0.8648 | −0.0765 | 0.034* | |
O22 | 0.48092 (16) | 0.39764 (15) | 0.20692 (18) | 0.0380 (4) | |
H22 | 0.4020 | 0.4272 | 0.2128 | 0.046* | |
O23 | 0.74473 (16) | 0.34100 (15) | 0.19177 (17) | 0.0348 (4) | |
H23 | 0.6730 | 0.3042 | 0.2414 | 0.042* | |
O24 | 1.09942 (17) | 0.72756 (15) | 0.29359 (17) | 0.0355 (4) | |
H24 | 1.1267 | 0.6574 | 0.2694 | 0.043* | |
O25 | 0.98041 (16) | 0.95779 (15) | 0.35537 (17) | 0.0342 (4) | |
H25 | 1.0480 | 0.9203 | 0.3693 | 0.041* | |
O26 | 0.35380 (16) | 1.06163 (16) | 0.46696 (16) | 0.0336 (4) | |
H26 | 0.4028 | 1.1156 | 0.4654 | 0.040* | |
O27 | 0.20381 (15) | 0.91070 (15) | 0.42175 (16) | 0.0320 (4) | |
H27 | 0.1805 | 0.9565 | 0.4817 | 0.038* | |
C30 | 0.3924 (2) | 0.6310 (2) | 0.4679 (3) | 0.0372 (6) | |
H30A | 0.3364 | 0.6828 | 0.4252 | 0.056* | |
H30B | 0.3320 | 0.5987 | 0.5596 | 0.056* | |
H30C | 0.4401 | 0.5626 | 0.4166 | 0.056* | |
C31 | 0.4974 (2) | 0.7061 (2) | 0.4715 (2) | 0.0301 (6) | |
C32 | 0.6384 (2) | 0.7056 (2) | 0.3618 (2) | 0.0364 (6) | |
H32A | 0.6944 | 0.7594 | 0.3771 | 0.055* | |
H32B | 0.6321 | 0.7353 | 0.2759 | 0.055* | |
H32C | 0.6820 | 0.6217 | 0.3599 | 0.055* | |
O33 | 0.46572 (17) | 0.76761 (16) | 0.56321 (17) | 0.0392 (4) | |
C40 | −0.0322 (3) | 0.4237 (3) | 0.3639 (3) | 0.0476 (7) | |
H40A | −0.0544 | 0.5127 | 0.3556 | 0.071* | |
H40B | −0.0797 | 0.3880 | 0.4576 | 0.071* | |
H40C | −0.0629 | 0.3872 | 0.3075 | 0.071* | |
C41 | 0.1208 (3) | 0.3980 (2) | 0.3197 (2) | 0.0348 (6) | |
C42 | 0.1718 (3) | 0.2688 (2) | 0.3462 (3) | 0.0454 (7) | |
H42A | 0.2711 | 0.2580 | 0.2895 | 0.068* | |
H42B | 0.1214 | 0.2133 | 0.3258 | 0.068* | |
H42C | 0.1567 | 0.2498 | 0.4407 | 0.068* | |
O43 | 0.20072 (17) | 0.48078 (16) | 0.26624 (18) | 0.0390 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0300 (13) | 0.0268 (13) | 0.0255 (13) | −0.0001 (10) | −0.0133 (11) | −0.0060 (10) |
C2 | 0.0239 (12) | 0.0319 (14) | 0.0325 (14) | 0.0011 (10) | −0.0137 (11) | −0.0077 (11) |
C3 | 0.0243 (12) | 0.0301 (14) | 0.0288 (13) | −0.0047 (10) | −0.0083 (11) | −0.0054 (11) |
C4 | 0.0286 (13) | 0.0256 (13) | 0.0276 (13) | 0.0016 (10) | −0.0112 (11) | −0.0042 (10) |
C5 | 0.0240 (12) | 0.0306 (14) | 0.0293 (14) | 0.0015 (10) | −0.0103 (11) | −0.0074 (11) |
C6 | 0.0286 (13) | 0.0311 (14) | 0.0217 (13) | −0.0025 (10) | −0.0101 (10) | −0.0044 (10) |
C7 | 0.0255 (12) | 0.0309 (14) | 0.0259 (13) | −0.0012 (10) | −0.0070 (11) | −0.0040 (11) |
C8 | 0.0216 (12) | 0.0288 (13) | 0.0254 (13) | −0.0050 (10) | −0.0059 (10) | −0.0008 (10) |
C9 | 0.0234 (12) | 0.0249 (13) | 0.0325 (14) | −0.0004 (10) | −0.0081 (11) | −0.0056 (11) |
C10 | 0.0206 (12) | 0.0311 (14) | 0.0301 (14) | −0.0043 (10) | −0.0101 (11) | −0.0010 (11) |
C11 | 0.0214 (12) | 0.0309 (14) | 0.0284 (13) | −0.0043 (10) | −0.0065 (11) | −0.0066 (11) |
C12 | 0.0235 (12) | 0.0232 (13) | 0.0327 (14) | −0.0021 (10) | −0.0090 (11) | −0.0054 (10) |
C13 | 0.0200 (11) | 0.0291 (14) | 0.0252 (13) | −0.0063 (10) | −0.0044 (10) | −0.0011 (10) |
C14 | 0.0283 (12) | 0.0248 (13) | 0.0269 (13) | −0.0017 (10) | −0.0088 (11) | −0.0034 (10) |
C15 | 0.0256 (12) | 0.0237 (13) | 0.0269 (13) | 0.0019 (10) | −0.0120 (10) | 0.0009 (10) |
C16 | 0.0275 (13) | 0.0216 (12) | 0.0330 (14) | −0.0011 (10) | −0.0149 (11) | −0.0035 (10) |
C17 | 0.0251 (12) | 0.0264 (13) | 0.0279 (13) | 0.0023 (10) | −0.0124 (11) | −0.0060 (10) |
C18 | 0.0218 (12) | 0.0263 (13) | 0.0299 (14) | 0.0011 (10) | −0.0132 (11) | −0.0003 (10) |
C19 | 0.0277 (12) | 0.0272 (13) | 0.0346 (14) | 0.0020 (10) | −0.0188 (11) | −0.0056 (11) |
C20 | 0.0289 (12) | 0.0238 (13) | 0.0284 (13) | 0.0025 (10) | −0.0163 (11) | −0.0015 (10) |
C21 | 0.0293 (13) | 0.0315 (14) | 0.0278 (13) | 0.0002 (10) | −0.0147 (11) | −0.0037 (11) |
O22 | 0.0260 (9) | 0.0316 (10) | 0.0542 (12) | −0.0024 (7) | −0.0160 (9) | −0.0008 (9) |
O23 | 0.0254 (9) | 0.0294 (10) | 0.0407 (11) | −0.0006 (7) | −0.0078 (8) | 0.0018 (8) |
O24 | 0.0373 (10) | 0.0311 (10) | 0.0475 (11) | 0.0042 (8) | −0.0262 (9) | −0.0104 (8) |
O25 | 0.0285 (9) | 0.0397 (11) | 0.0419 (11) | 0.0039 (7) | −0.0191 (8) | −0.0169 (9) |
O26 | 0.0298 (9) | 0.0382 (11) | 0.0353 (10) | −0.0038 (7) | −0.0122 (8) | −0.0131 (8) |
O27 | 0.0234 (9) | 0.0396 (11) | 0.0330 (10) | −0.0013 (7) | −0.0095 (8) | −0.0111 (8) |
C30 | 0.0377 (15) | 0.0353 (15) | 0.0404 (16) | −0.0068 (12) | −0.0178 (13) | −0.0014 (12) |
C31 | 0.0338 (14) | 0.0257 (13) | 0.0316 (14) | −0.0020 (10) | −0.0160 (12) | 0.0009 (11) |
C32 | 0.0360 (14) | 0.0365 (15) | 0.0336 (15) | −0.0047 (11) | −0.0104 (12) | −0.0052 (12) |
O33 | 0.0369 (10) | 0.0448 (11) | 0.0331 (10) | −0.0073 (8) | −0.0081 (8) | −0.0113 (9) |
C40 | 0.0316 (15) | 0.0583 (19) | 0.0501 (18) | −0.0053 (13) | −0.0152 (14) | −0.0027 (15) |
C41 | 0.0331 (14) | 0.0415 (16) | 0.0312 (15) | −0.0014 (12) | −0.0144 (12) | −0.0065 (12) |
C42 | 0.0484 (17) | 0.0374 (17) | 0.0496 (18) | −0.0065 (13) | −0.0205 (15) | 0.0007 (13) |
O43 | 0.0325 (10) | 0.0349 (11) | 0.0493 (12) | −0.0015 (8) | −0.0173 (9) | −0.0037 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.401 (3) | C17—O26 | 1.369 (3) |
C1—C6 | 1.408 (3) | C17—C18 | 1.396 (3) |
C1—C21 | 1.520 (3) | C18—C19 | 1.379 (3) |
C2—C3 | 1.375 (3) | C18—O27 | 1.390 (3) |
C2—H2 | 0.9500 | C19—C20 | 1.406 (3) |
C3—O22 | 1.373 (3) | C19—H19 | 0.9500 |
C3—C4 | 1.398 (3) | C20—C21 | 1.521 (3) |
C4—O23 | 1.372 (3) | C21—H21A | 0.9900 |
C4—C5 | 1.378 (3) | C21—H21B | 0.9900 |
C5—C6 | 1.392 (3) | O22—H22 | 0.8400 |
C5—H5 | 0.9500 | O23—H23 | 0.8400 |
C6—C7 | 1.531 (3) | O24—H24 | 0.8400 |
C7—C8 | 1.521 (3) | O25—H25 | 0.8400 |
C7—H7A | 0.9900 | O26—H26 | 0.8400 |
C7—H7B | 0.9900 | O27—H27 | 0.8400 |
C8—C13 | 1.396 (3) | C30—C31 | 1.500 (3) |
C8—C9 | 1.403 (3) | C30—H30A | 0.9800 |
C9—C10 | 1.382 (3) | C30—H30B | 0.9800 |
C9—H9 | 0.9500 | C30—H30C | 0.9800 |
C10—O24 | 1.382 (3) | C31—O33 | 1.227 (3) |
C10—C11 | 1.394 (3) | C31—C32 | 1.482 (3) |
C11—O25 | 1.379 (3) | C32—H32A | 0.9800 |
C11—C12 | 1.381 (3) | C32—H32B | 0.9800 |
C12—C13 | 1.398 (3) | C32—H32C | 0.9800 |
C12—H12 | 0.9500 | C40—C41 | 1.494 (3) |
C13—C14 | 1.522 (3) | C40—H40A | 0.9800 |
C14—C15 | 1.514 (3) | C40—H40B | 0.9800 |
C14—H14A | 0.9900 | C40—H40C | 0.9800 |
C14—H14B | 0.9900 | C41—O43 | 1.232 (3) |
C15—C16 | 1.393 (3) | C41—C42 | 1.486 (4) |
C15—C20 | 1.404 (3) | C42—H42A | 0.9800 |
C16—C17 | 1.375 (3) | C42—H42B | 0.9800 |
C16—H16 | 0.9500 | C42—H42C | 0.9800 |
| | | |
C2—C1—C6 | 118.1 (2) | O26—C17—C16 | 124.61 (19) |
C2—C1—C21 | 117.3 (2) | O26—C17—C18 | 116.8 (2) |
C6—C1—C21 | 124.4 (2) | C16—C17—C18 | 118.6 (2) |
C3—C2—C1 | 122.7 (2) | C19—C18—O27 | 120.24 (19) |
C3—C2—H2 | 118.7 | C19—C18—C17 | 119.9 (2) |
C1—C2—H2 | 118.7 | O27—C18—C17 | 119.8 (2) |
O22—C3—C2 | 124.4 (2) | C18—C19—C20 | 121.6 (2) |
O22—C3—C4 | 116.4 (2) | C18—C19—H19 | 119.2 |
C2—C3—C4 | 119.2 (2) | C20—C19—H19 | 119.2 |
O23—C4—C5 | 119.4 (2) | C15—C20—C19 | 118.4 (2) |
O23—C4—C3 | 122.1 (2) | C15—C20—C21 | 123.2 (2) |
C5—C4—C3 | 118.5 (2) | C19—C20—C21 | 118.25 (19) |
C4—C5—C6 | 123.2 (2) | C1—C21—C20 | 111.66 (18) |
C4—C5—H5 | 118.4 | C1—C21—H21A | 109.3 |
C6—C5—H5 | 118.4 | C20—C21—H21A | 109.3 |
C5—C6—C1 | 118.2 (2) | C1—C21—H21B | 109.3 |
C5—C6—C7 | 118.0 (2) | C20—C21—H21B | 109.3 |
C1—C6—C7 | 123.7 (2) | H21A—C21—H21B | 107.9 |
C8—C7—C6 | 114.22 (18) | C3—O22—H22 | 109.5 |
C8—C7—H7A | 108.7 | C4—O23—H23 | 109.5 |
C6—C7—H7A | 108.7 | C10—O24—H24 | 109.5 |
C8—C7—H7B | 108.7 | C11—O25—H25 | 109.5 |
C6—C7—H7B | 108.7 | C17—O26—H26 | 109.5 |
H7A—C7—H7B | 107.6 | C18—O27—H27 | 109.5 |
C13—C8—C9 | 118.6 (2) | C31—C30—H30A | 109.5 |
C13—C8—C7 | 122.5 (2) | C31—C30—H30B | 109.5 |
C9—C8—C7 | 118.9 (2) | H30A—C30—H30B | 109.5 |
C10—C9—C8 | 121.9 (2) | C31—C30—H30C | 109.5 |
C10—C9—H9 | 119.1 | H30A—C30—H30C | 109.5 |
C8—C9—H9 | 119.1 | H30B—C30—H30C | 109.5 |
C9—C10—O24 | 123.9 (2) | O33—C31—C32 | 121.0 (2) |
C9—C10—C11 | 119.4 (2) | O33—C31—C30 | 120.1 (2) |
O24—C10—C11 | 116.70 (19) | C32—C31—C30 | 118.9 (2) |
O25—C11—C12 | 118.6 (2) | C31—C32—H32A | 109.5 |
O25—C11—C10 | 122.3 (2) | C31—C32—H32B | 109.5 |
C12—C11—C10 | 119.1 (2) | H32A—C32—H32B | 109.5 |
C11—C12—C13 | 122.0 (2) | C31—C32—H32C | 109.5 |
C11—C12—H12 | 119.0 | H32A—C32—H32C | 109.5 |
C13—C12—H12 | 119.0 | H32B—C32—H32C | 109.5 |
C8—C13—C12 | 119.0 (2) | C41—C40—H40A | 109.5 |
C8—C13—C14 | 123.3 (2) | C41—C40—H40B | 109.5 |
C12—C13—C14 | 117.7 (2) | H40A—C40—H40B | 109.5 |
C15—C14—C13 | 110.69 (18) | C41—C40—H40C | 109.5 |
C15—C14—H14A | 109.5 | H40A—C40—H40C | 109.5 |
C13—C14—H14A | 109.5 | H40B—C40—H40C | 109.5 |
C15—C14—H14B | 109.5 | O43—C41—C42 | 121.5 (2) |
C13—C14—H14B | 109.5 | O43—C41—C40 | 121.4 (2) |
H14A—C14—H14B | 108.1 | C42—C41—C40 | 117.1 (2) |
C16—C15—C20 | 118.7 (2) | C41—C42—H42A | 109.5 |
C16—C15—C14 | 116.96 (19) | C41—C42—H42B | 109.5 |
C20—C15—C14 | 124.3 (2) | H42A—C42—H42B | 109.5 |
C17—C16—C15 | 122.7 (2) | C41—C42—H42C | 109.5 |
C17—C16—H16 | 118.6 | H42A—C42—H42C | 109.5 |
C15—C16—H16 | 118.6 | H42B—C42—H42C | 109.5 |
| | | |
C6—C1—C2—C3 | 2.6 (3) | C9—C8—C13—C12 | 0.4 (3) |
C21—C1—C2—C3 | −172.6 (2) | C7—C8—C13—C12 | −179.3 (2) |
C1—C2—C3—O22 | 178.4 (2) | C9—C8—C13—C14 | −177.2 (2) |
C1—C2—C3—C4 | −1.0 (3) | C7—C8—C13—C14 | 3.2 (3) |
O22—C3—C4—O23 | −0.7 (3) | C11—C12—C13—C8 | −1.9 (3) |
C2—C3—C4—O23 | 178.7 (2) | C11—C12—C13—C14 | 175.8 (2) |
O22—C3—C4—C5 | 179.9 (2) | C8—C13—C14—C15 | 92.5 (3) |
C2—C3—C4—C5 | −0.7 (3) | C12—C13—C14—C15 | −85.1 (2) |
O23—C4—C5—C6 | −178.8 (2) | C13—C14—C15—C16 | 77.4 (2) |
C3—C4—C5—C6 | 0.6 (3) | C13—C14—C15—C20 | −99.4 (2) |
C4—C5—C6—C1 | 1.0 (3) | C20—C15—C16—C17 | 1.1 (3) |
C4—C5—C6—C7 | 178.0 (2) | C14—C15—C16—C17 | −175.9 (2) |
C2—C1—C6—C5 | −2.6 (3) | C15—C16—C17—O26 | 177.5 (2) |
C21—C1—C6—C5 | 172.2 (2) | C15—C16—C17—C18 | −1.8 (3) |
C2—C1—C6—C7 | −179.4 (2) | O26—C17—C18—C19 | −178.6 (2) |
C21—C1—C6—C7 | −4.6 (3) | C16—C17—C18—C19 | 0.8 (3) |
C5—C6—C7—C8 | −79.6 (3) | O26—C17—C18—O27 | 0.0 (3) |
C1—C6—C7—C8 | 97.2 (3) | C16—C17—C18—O27 | 179.3 (2) |
C6—C7—C8—C13 | −96.2 (3) | O27—C18—C19—C20 | −177.6 (2) |
C6—C7—C8—C9 | 84.2 (3) | C17—C18—C19—C20 | 1.0 (3) |
C13—C8—C9—C10 | 1.6 (3) | C16—C15—C20—C19 | 0.6 (3) |
C7—C8—C9—C10 | −178.8 (2) | C14—C15—C20—C19 | 177.4 (2) |
C8—C9—C10—O24 | 179.0 (2) | C16—C15—C20—C21 | −175.5 (2) |
C8—C9—C10—C11 | −2.1 (3) | C14—C15—C20—C21 | 1.2 (3) |
C9—C10—C11—O25 | −179.0 (2) | C18—C19—C20—C15 | −1.6 (3) |
O24—C10—C11—O25 | 0.0 (3) | C18—C19—C20—C21 | 174.7 (2) |
C9—C10—C11—C12 | 0.5 (3) | C2—C1—C21—C20 | 85.6 (2) |
O24—C10—C11—C12 | 179.6 (2) | C6—C1—C21—C20 | −89.3 (3) |
O25—C11—C12—C13 | −179.0 (2) | C15—C20—C21—C1 | 95.1 (3) |
C10—C11—C12—C13 | 1.4 (3) | C19—C20—C21—C1 | −81.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O22—H22···O43 | 0.84 | 2.00 | 2.831 (2) | 168 |
O23—H23···O33i | 0.84 | 2.13 | 2.884 (2) | 150 |
O23—H23···O22 | 0.84 | 2.32 | 2.738 (2) | 112 |
O24—H24···O43ii | 0.84 | 2.01 | 2.818 (2) | 162 |
O25—H25···O27ii | 0.84 | 1.97 | 2.740 (2) | 153 |
O25—H25···O24 | 0.84 | 2.34 | 2.754 (2) | 111 |
O26—H26···O33iii | 0.84 | 1.93 | 2.762 (2) | 172 |
O27—H27···O25iii | 0.84 | 2.16 | 2.911 (2) | 149 |
O27—H27···O26 | 0.84 | 2.25 | 2.704 (2) | 114 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1. |