The title compound, C
38H
50O
6, also known as guttiferone A, was isolated from the medicinal plant
Symphonia globulifera. It is a benzophenone derivative where one aryl group is derivatized to give a bicyclic system which has two prenyl groups attached to the bridgehead. One of the cyclohexane rings in the bicyclic system is in a chair form, while the other has a distorted half-chair conformation. In addition to an intramolecular O—H
O hydrogen bond, intermolecular O—H
O hydrogen bonds link molecules into one-dimensional chains.
Supporting information
CCDC reference: 640409
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.105
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.14 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.67 Ratio
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C36
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 29.13
From the CIF: _reflns_number_total 5171
Count of symmetry unique reflns 5207
Completeness (_total/calc) 99.31%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26 = . S
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: ..
Identification and collection of plant, fractionation of extract and
isolation were made at the Departement of Organic Chemistry, Faculty of
Science, University of Yaounde 1, Cameroon by Bruno Ndjakou Lenta, Silvere
Ngouela and Etienne Tsamo. Crystallisation, NMR , Xray analysis ,
interpretation of data were carried on at Bielefed University by Bruno
Ndjakou Lenta, Norbert Sewald, Krishna Prasad Devkota and Patrice Aime Fokou
.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.
(1
R,5
R,7
R,8S)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8-methyl-1,5,7-tris(3-
methyl-2-butenyl)-8-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione
top
Crystal data top
C38H50O6 | F(000) = 1304 |
Mr = 602.78 | Dx = 1.160 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4991 reflections |
a = 8.786 (1) Å | θ = 1.0–29.1° |
b = 11.449 (1) Å | µ = 0.08 mm−1 |
c = 34.306 (2) Å | T = 173 K |
V = 3450.9 (5) Å3 | Prism, colorless |
Z = 4 | 0.16 × 0.14 × 0.12 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 3899 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 29.1°, θmin = 1.9° |
φ scans | h = −12→12 |
9050 measured reflections | k = −15→15 |
5171 independent reflections | l = −46→46 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.2481P] where P = (Fo2 + 2Fc2)/3 |
5171 reflections | (Δ/σ)max = 0.001 |
400 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.18 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 | |
O1A | 0.67799 (18) | −0.21629 (16) | −0.07016 (4) | 0.0375 (4) | |
H1O | 0.7458 | −0.2652 | −0.0757 | 0.056* | |
O2 | 0.5018 (2) | −0.03885 (17) | −0.04626 (4) | 0.0466 (5) | |
H2O | 0.5171 | −0.0656 | −0.0687 | 0.070* | |
O3A | 0.86545 (17) | −0.06552 (16) | 0.09727 (4) | 0.0375 (4) | |
H3O | 0.8665 | −0.0425 | 0.1205 | 0.056* | |
O4 | 0.40429 (17) | −0.11708 (13) | 0.07929 (4) | 0.0299 (3) | |
O5 | 0.34069 (17) | 0.21458 (13) | 0.15260 (4) | 0.0325 (4) | |
O6 | 0.78963 (16) | 0.01873 (14) | 0.15805 (4) | 0.0299 (3) | |
C1 | 0.8115 (3) | −0.1848 (2) | 0.03061 (6) | 0.0334 (5) | |
H1 | 0.8856 | −0.2158 | 0.0479 | 0.040* | |
C2 | 0.8022 (3) | −0.2267 (2) | −0.00734 (6) | 0.0355 (5) | |
H2 | 0.8678 | −0.2876 | −0.0158 | 0.043* | |
C3 | 0.6972 (3) | −0.17935 (19) | −0.03258 (6) | 0.0290 (5) | |
C4 | 0.6032 (3) | −0.0881 (2) | −0.02065 (6) | 0.0304 (5) | |
C5 | 0.6089 (3) | −0.04798 (19) | 0.01720 (6) | 0.0293 (5) | |
H5 | 0.5428 | 0.0128 | 0.0255 | 0.035* | |
C6 | 0.7129 (2) | −0.09752 (19) | 0.04335 (6) | 0.0268 (4) | |
C7 | 0.7288 (2) | −0.05943 (19) | 0.08380 (6) | 0.0271 (5) | |
C8 | 0.6099 (2) | −0.01620 (17) | 0.10850 (5) | 0.0226 (4) | |
C9 | 0.4490 (2) | −0.04212 (18) | 0.10227 (5) | 0.0236 (4) | |
C10 | 0.3308 (2) | 0.01980 (18) | 0.12740 (5) | 0.0236 (4) | |
C11 | 0.3997 (2) | 0.11934 (18) | 0.15022 (5) | 0.0241 (4) | |
C12 | 0.5401 (2) | 0.08585 (18) | 0.17339 (5) | 0.0237 (4) | |
C13 | 0.6530 (2) | 0.02649 (18) | 0.14614 (5) | 0.0242 (4) | |
C14 | 0.1972 (2) | 0.0602 (2) | 0.10136 (6) | 0.0307 (5) | |
H14A | 0.1484 | −0.0093 | 0.0896 | 0.037* | |
H14B | 0.1204 | 0.0996 | 0.1179 | 0.037* | |
C15 | 0.2445 (3) | 0.1424 (2) | 0.06917 (7) | 0.0386 (6) | |
H15 | 0.2975 | 0.2108 | 0.0770 | 0.046* | |
C16 | 0.2207 (3) | 0.1299 (2) | 0.03130 (7) | 0.0438 (6) | |
C17 | 0.2746 (4) | 0.2221 (3) | 0.00251 (9) | 0.0731 (10) | |
H17A | 0.3229 | 0.2864 | 0.0167 | 0.110* | |
H17B | 0.1873 | 0.2519 | −0.0122 | 0.110* | |
H17C | 0.3483 | 0.1873 | −0.0155 | 0.110* | |
C18 | 0.1421 (4) | 0.0284 (3) | 0.01271 (8) | 0.0608 (8) | |
H18A | 0.1231 | −0.0320 | 0.0324 | 0.091* | |
H18B | 0.2067 | −0.0037 | −0.0080 | 0.091* | |
H18C | 0.0452 | 0.0543 | 0.0016 | 0.091* | |
C19 | 0.6197 (3) | 0.19799 (19) | 0.18872 (6) | 0.0284 (5) | |
H19A | 0.5452 | 0.2453 | 0.2036 | 0.034* | |
H19B | 0.7026 | 0.1756 | 0.2068 | 0.034* | |
C20 | 0.6844 (3) | 0.27072 (19) | 0.15624 (6) | 0.0304 (5) | |
H20 | 0.6140 | 0.2953 | 0.1369 | 0.036* | |
C21 | 0.8268 (3) | 0.30484 (19) | 0.15114 (7) | 0.0337 (5) | |
C22 | 0.9540 (3) | 0.2781 (3) | 0.17891 (8) | 0.0461 (7) | |
H22A | 0.9572 | 0.3379 | 0.1993 | 0.069* | |
H22B | 1.0509 | 0.2777 | 0.1648 | 0.069* | |
H22C | 0.9370 | 0.2014 | 0.1908 | 0.069* | |
C23 | 0.8743 (3) | 0.3757 (2) | 0.11631 (7) | 0.0512 (7) | |
H23A | 0.7903 | 0.3787 | 0.0975 | 0.077* | |
H23B | 0.9633 | 0.3395 | 0.1041 | 0.077* | |
H23C | 0.9001 | 0.4552 | 0.1246 | 0.077* | |
C24 | 0.2731 (2) | −0.06685 (18) | 0.15917 (6) | 0.0252 (4) | |
H24A | 0.1885 | −0.0293 | 0.1735 | 0.030* | |
H24B | 0.2314 | −0.1368 | 0.1460 | 0.030* | |
C25 | 0.3940 (3) | −0.10702 (18) | 0.18896 (5) | 0.0258 (4) | |
H25 | 0.3340 | −0.1402 | 0.2111 | 0.031* | |
C26 | 0.4825 (2) | −0.00143 (18) | 0.20710 (5) | 0.0249 (4) | |
C27 | 0.4929 (2) | −0.20993 (18) | 0.17429 (6) | 0.0275 (5) | |
H27A | 0.5497 | −0.1848 | 0.1508 | 0.033* | |
H27B | 0.5681 | −0.2305 | 0.1946 | 0.033* | |
C28 | 0.4004 (3) | −0.3162 (2) | 0.16449 (7) | 0.0357 (5) | |
H28 | 0.3182 | −0.3329 | 0.1816 | 0.043* | |
C29 | 0.4191 (3) | −0.3898 (2) | 0.13499 (7) | 0.0415 (6) | |
C30 | 0.5374 (3) | −0.3773 (2) | 0.10369 (8) | 0.0522 (7) | |
H30A | 0.5846 | −0.3000 | 0.1055 | 0.078* | |
H30B | 0.4894 | −0.3862 | 0.0781 | 0.078* | |
H30C | 0.6154 | −0.4377 | 0.1070 | 0.078* | |
C31 | 0.3210 (4) | −0.4970 (2) | 0.13093 (10) | 0.0644 (9) | |
H31A | 0.2451 | −0.4982 | 0.1519 | 0.097* | |
H31B | 0.3848 | −0.5670 | 0.1327 | 0.097* | |
H31C | 0.2692 | −0.4955 | 0.1056 | 0.097* | |
C32 | 0.6170 (3) | −0.0437 (2) | 0.23204 (6) | 0.0318 (5) | |
H32A | 0.6614 | 0.0227 | 0.2460 | 0.048* | |
H32B | 0.6944 | −0.0790 | 0.2151 | 0.048* | |
H32C | 0.5811 | −0.1019 | 0.2509 | 0.048* | |
C33 | 0.3751 (3) | 0.06942 (19) | 0.23428 (5) | 0.0297 (5) | |
H33A | 0.4368 | 0.1281 | 0.2484 | 0.036* | |
H33B | 0.3014 | 0.1124 | 0.2178 | 0.036* | |
C34 | 0.2854 (3) | −0.0028 (2) | 0.26450 (6) | 0.0343 (5) | |
H34A | 0.1970 | −0.0402 | 0.2516 | 0.041* | |
H34B | 0.3515 | −0.0654 | 0.2750 | 0.041* | |
C35 | 0.2300 (3) | 0.0736 (2) | 0.29769 (6) | 0.0317 (5) | |
H35 | 0.2998 | 0.0862 | 0.3184 | 0.038* | |
C36 | 0.0972 (3) | 0.1241 (2) | 0.30112 (6) | 0.0397 (6) | |
C37 | 0.0612 (3) | 0.2007 (3) | 0.33590 (8) | 0.0531 (7) | |
H37A | 0.1488 | 0.2021 | 0.3536 | 0.080* | |
H37B | −0.0276 | 0.1694 | 0.3496 | 0.080* | |
H37C | 0.0392 | 0.2802 | 0.3270 | 0.080* | |
C38 | −0.0300 (4) | 0.1075 (4) | 0.27284 (9) | 0.0936 (15) | |
H38A | 0.0097 | 0.0732 | 0.2487 | 0.140* | |
H38B | −0.0768 | 0.1832 | 0.2671 | 0.140* | |
H38C | −0.1064 | 0.0552 | 0.2842 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0370 (9) | 0.0493 (11) | 0.0263 (8) | 0.0056 (9) | 0.0026 (7) | −0.0089 (7) |
O2 | 0.0570 (11) | 0.0550 (11) | 0.0279 (8) | 0.0199 (10) | −0.0025 (8) | 0.0025 (8) |
O3A | 0.0245 (8) | 0.0554 (11) | 0.0327 (8) | 0.0025 (8) | −0.0001 (6) | −0.0161 (8) |
O4 | 0.0273 (8) | 0.0326 (8) | 0.0298 (7) | −0.0031 (7) | −0.0018 (6) | −0.0094 (7) |
O5 | 0.0326 (8) | 0.0234 (8) | 0.0417 (8) | 0.0032 (7) | 0.0049 (7) | −0.0040 (6) |
O6 | 0.0221 (7) | 0.0372 (9) | 0.0303 (7) | −0.0015 (7) | −0.0029 (6) | −0.0067 (6) |
C1 | 0.0299 (12) | 0.0387 (13) | 0.0315 (11) | 0.0088 (11) | −0.0022 (10) | −0.0055 (10) |
C2 | 0.0343 (13) | 0.0395 (13) | 0.0325 (12) | 0.0104 (11) | 0.0026 (10) | −0.0092 (10) |
C3 | 0.0306 (12) | 0.0337 (12) | 0.0227 (10) | −0.0011 (10) | 0.0054 (9) | −0.0036 (8) |
C4 | 0.0314 (12) | 0.0331 (12) | 0.0266 (10) | 0.0015 (11) | 0.0034 (9) | 0.0035 (9) |
C5 | 0.0287 (11) | 0.0288 (11) | 0.0304 (11) | 0.0045 (10) | 0.0074 (9) | −0.0004 (9) |
C6 | 0.0257 (11) | 0.0299 (11) | 0.0248 (10) | −0.0006 (10) | 0.0043 (8) | −0.0032 (8) |
C7 | 0.0235 (10) | 0.0261 (11) | 0.0317 (11) | −0.0021 (9) | 0.0026 (9) | −0.0033 (9) |
C8 | 0.0230 (10) | 0.0216 (10) | 0.0232 (9) | −0.0010 (9) | 0.0022 (8) | −0.0020 (8) |
C9 | 0.0252 (10) | 0.0244 (11) | 0.0214 (10) | 0.0017 (9) | −0.0010 (8) | −0.0003 (8) |
C10 | 0.0209 (10) | 0.0226 (10) | 0.0274 (10) | 0.0001 (9) | 0.0015 (8) | −0.0021 (8) |
C11 | 0.0245 (10) | 0.0223 (10) | 0.0253 (10) | −0.0036 (9) | 0.0078 (8) | −0.0014 (8) |
C12 | 0.0250 (10) | 0.0226 (10) | 0.0237 (10) | −0.0036 (9) | 0.0035 (8) | −0.0038 (8) |
C13 | 0.0232 (10) | 0.0221 (10) | 0.0272 (10) | −0.0024 (9) | 0.0016 (8) | −0.0011 (8) |
C14 | 0.0243 (11) | 0.0324 (12) | 0.0353 (11) | 0.0017 (10) | −0.0007 (9) | −0.0048 (9) |
C15 | 0.0361 (14) | 0.0338 (13) | 0.0459 (14) | 0.0008 (11) | −0.0068 (11) | 0.0054 (10) |
C16 | 0.0419 (14) | 0.0453 (15) | 0.0443 (15) | 0.0114 (13) | −0.0047 (12) | 0.0089 (11) |
C17 | 0.087 (3) | 0.075 (2) | 0.0572 (18) | 0.004 (2) | −0.0079 (18) | 0.0304 (17) |
C18 | 0.073 (2) | 0.065 (2) | 0.0444 (15) | 0.0071 (19) | −0.0131 (14) | −0.0030 (14) |
C19 | 0.0330 (12) | 0.0256 (11) | 0.0268 (10) | −0.0078 (10) | 0.0042 (9) | −0.0057 (8) |
C20 | 0.0392 (13) | 0.0240 (10) | 0.0281 (11) | −0.0052 (10) | 0.0039 (10) | −0.0043 (9) |
C21 | 0.0370 (13) | 0.0261 (11) | 0.0379 (12) | −0.0053 (10) | 0.0102 (10) | −0.0056 (9) |
C22 | 0.0340 (14) | 0.0518 (16) | 0.0526 (15) | −0.0091 (13) | 0.0063 (12) | −0.0060 (13) |
C23 | 0.0592 (18) | 0.0435 (15) | 0.0509 (15) | −0.0131 (15) | 0.0226 (14) | 0.0023 (12) |
C24 | 0.0227 (10) | 0.0231 (10) | 0.0298 (10) | −0.0022 (9) | 0.0042 (8) | −0.0029 (8) |
C25 | 0.0275 (11) | 0.0240 (10) | 0.0260 (10) | −0.0042 (10) | 0.0042 (9) | −0.0011 (8) |
C26 | 0.0267 (11) | 0.0248 (11) | 0.0232 (10) | −0.0027 (9) | 0.0041 (8) | 0.0010 (8) |
C27 | 0.0274 (11) | 0.0209 (10) | 0.0342 (11) | −0.0007 (9) | 0.0004 (9) | −0.0024 (8) |
C28 | 0.0347 (13) | 0.0229 (11) | 0.0494 (14) | −0.0013 (11) | −0.0004 (11) | 0.0024 (10) |
C29 | 0.0426 (14) | 0.0241 (12) | 0.0577 (15) | 0.0052 (11) | −0.0183 (12) | −0.0060 (11) |
C30 | 0.0623 (18) | 0.0447 (16) | 0.0498 (15) | 0.0187 (15) | −0.0088 (14) | −0.0174 (12) |
C31 | 0.070 (2) | 0.0266 (14) | 0.097 (2) | −0.0005 (15) | −0.0272 (18) | −0.0134 (13) |
C32 | 0.0347 (12) | 0.0319 (12) | 0.0288 (11) | −0.0053 (11) | −0.0017 (9) | 0.0001 (9) |
C33 | 0.0375 (12) | 0.0268 (11) | 0.0248 (10) | −0.0047 (10) | 0.0086 (9) | −0.0036 (8) |
C34 | 0.0401 (13) | 0.0310 (12) | 0.0317 (11) | −0.0032 (11) | 0.0122 (10) | −0.0006 (9) |
C35 | 0.0317 (12) | 0.0353 (13) | 0.0280 (11) | −0.0031 (11) | 0.0060 (9) | −0.0007 (9) |
C36 | 0.0395 (14) | 0.0472 (15) | 0.0324 (12) | 0.0053 (13) | 0.0055 (10) | 0.0033 (11) |
C37 | 0.0536 (17) | 0.0486 (17) | 0.0572 (16) | 0.0095 (15) | 0.0181 (14) | −0.0078 (13) |
C38 | 0.070 (2) | 0.158 (4) | 0.0526 (18) | 0.051 (3) | −0.0222 (17) | −0.018 (2) |
Geometric parameters (Å, º) top
O1A—C3 | 1.367 (2) | C21—C22 | 1.500 (4) |
O1A—H1O | 0.8400 | C21—C23 | 1.504 (3) |
O2—C4 | 1.373 (3) | C22—H22A | 0.9800 |
O2—H2O | 0.8400 | C22—H22B | 0.9800 |
O3A—C7 | 1.289 (3) | C22—H22C | 0.9800 |
O3A—H3O | 0.8400 | C23—H23A | 0.9800 |
O4—C9 | 1.230 (2) | C23—H23B | 0.9800 |
O5—C11 | 1.210 (3) | C23—H23C | 0.9800 |
O6—C13 | 1.271 (2) | C24—C25 | 1.544 (3) |
C1—C2 | 1.390 (3) | C24—H24A | 0.9900 |
C1—C6 | 1.393 (3) | C24—H24B | 0.9900 |
C1—H1 | 0.9500 | C25—C27 | 1.548 (3) |
C2—C3 | 1.377 (3) | C25—C26 | 1.566 (3) |
C2—H2 | 0.9500 | C25—H25 | 1.0000 |
C3—C4 | 1.393 (3) | C26—C32 | 1.538 (3) |
C4—C5 | 1.378 (3) | C26—C33 | 1.555 (3) |
C5—C6 | 1.400 (3) | C27—C28 | 1.501 (3) |
C5—H5 | 0.9500 | C27—H27A | 0.9900 |
C6—C7 | 1.461 (3) | C27—H27B | 0.9900 |
C7—C8 | 1.433 (3) | C28—C29 | 1.327 (3) |
C8—C13 | 1.432 (3) | C28—H28 | 0.9500 |
C8—C9 | 1.460 (3) | C29—C30 | 1.501 (4) |
C9—C10 | 1.524 (3) | C29—C31 | 1.506 (4) |
C10—C11 | 1.510 (3) | C30—H30A | 0.9800 |
C10—C14 | 1.546 (3) | C30—H30B | 0.9800 |
C10—C24 | 1.558 (3) | C30—H30C | 0.9800 |
C11—C12 | 1.517 (3) | C31—H31A | 0.9800 |
C12—C13 | 1.523 (3) | C31—H31B | 0.9800 |
C12—C19 | 1.554 (3) | C31—H31C | 0.9800 |
C12—C26 | 1.610 (3) | C32—H32A | 0.9800 |
C14—C15 | 1.509 (3) | C32—H32B | 0.9800 |
C14—H14A | 0.9900 | C32—H32C | 0.9800 |
C14—H14B | 0.9900 | C33—C34 | 1.543 (3) |
C15—C16 | 1.324 (3) | C33—H33A | 0.9900 |
C15—H15 | 0.9500 | C33—H33B | 0.9900 |
C16—C18 | 1.494 (4) | C34—C35 | 1.516 (3) |
C16—C17 | 1.521 (4) | C34—H34A | 0.9900 |
C17—H17A | 0.9800 | C34—H34B | 0.9900 |
C17—H17B | 0.9800 | C35—C36 | 1.307 (4) |
C17—H17C | 0.9800 | C35—H35 | 0.9500 |
C18—H18A | 0.9800 | C36—C38 | 1.492 (4) |
C18—H18B | 0.9800 | C36—C37 | 1.514 (4) |
C18—H18C | 0.9800 | C37—H37A | 0.9800 |
C19—C20 | 1.503 (3) | C37—H37B | 0.9800 |
C19—H19A | 0.9900 | C37—H37C | 0.9800 |
C19—H19B | 0.9900 | C38—H38A | 0.9800 |
C20—C21 | 1.322 (3) | C38—H38B | 0.9800 |
C20—H20 | 0.9500 | C38—H38C | 0.9800 |
| | | |
C3—O1A—H1O | 109.5 | C21—C22—H22C | 109.5 |
C4—O2—H2O | 109.5 | H22A—C22—H22C | 109.5 |
C7—O3A—H3O | 109.5 | H22B—C22—H22C | 109.5 |
C2—C1—C6 | 120.3 (2) | C21—C23—H23A | 109.5 |
C2—C1—H1 | 119.8 | C21—C23—H23B | 109.5 |
C6—C1—H1 | 119.8 | H23A—C23—H23B | 109.5 |
C3—C2—C1 | 119.5 (2) | C21—C23—H23C | 109.5 |
C3—C2—H2 | 120.2 | H23A—C23—H23C | 109.5 |
C1—C2—H2 | 120.2 | H23B—C23—H23C | 109.5 |
O1A—C3—C2 | 123.7 (2) | C25—C24—C10 | 115.40 (17) |
O1A—C3—C4 | 115.8 (2) | C25—C24—H24A | 108.4 |
C2—C3—C4 | 120.5 (2) | C10—C24—H24A | 108.4 |
O2—C4—C5 | 119.3 (2) | C25—C24—H24B | 108.4 |
O2—C4—C3 | 120.34 (19) | C10—C24—H24B | 108.4 |
C5—C4—C3 | 120.3 (2) | H24A—C24—H24B | 107.5 |
C4—C5—C6 | 119.5 (2) | C24—C25—C27 | 113.43 (17) |
C4—C5—H5 | 120.3 | C24—C25—C26 | 112.00 (17) |
C6—C5—H5 | 120.3 | C27—C25—C26 | 115.97 (18) |
C1—C6—C5 | 119.70 (18) | C24—C25—H25 | 104.7 |
C1—C6—C7 | 116.9 (2) | C27—C25—H25 | 104.7 |
C5—C6—C7 | 123.4 (2) | C26—C25—H25 | 104.7 |
O3A—C7—C8 | 119.07 (18) | C32—C26—C33 | 107.30 (16) |
O3A—C7—C6 | 114.42 (19) | C32—C26—C25 | 111.07 (17) |
C8—C7—C6 | 126.50 (19) | C33—C26—C25 | 109.86 (17) |
C13—C8—C7 | 117.27 (18) | C32—C26—C12 | 110.70 (17) |
C13—C8—C9 | 117.24 (18) | C33—C26—C12 | 107.32 (16) |
C7—C8—C9 | 123.29 (18) | C25—C26—C12 | 110.47 (15) |
O4—C9—C8 | 123.01 (18) | C28—C27—C25 | 112.70 (18) |
O4—C9—C10 | 118.00 (18) | C28—C27—H27A | 109.1 |
C8—C9—C10 | 118.83 (17) | C25—C27—H27A | 109.1 |
C11—C10—C9 | 111.78 (17) | C28—C27—H27B | 109.1 |
C11—C10—C14 | 112.22 (18) | C25—C27—H27B | 109.1 |
C9—C10—C14 | 109.25 (15) | H27A—C27—H27B | 107.8 |
C11—C10—C24 | 104.38 (15) | C29—C28—C27 | 128.2 (2) |
C9—C10—C24 | 108.72 (16) | C29—C28—H28 | 115.9 |
C14—C10—C24 | 110.35 (17) | C27—C28—H28 | 115.9 |
O5—C11—C10 | 122.92 (19) | C28—C29—C30 | 124.8 (2) |
O5—C11—C12 | 122.74 (19) | C28—C29—C31 | 121.1 (3) |
C10—C11—C12 | 114.03 (18) | C30—C29—C31 | 114.1 (2) |
C11—C12—C13 | 108.73 (15) | C29—C30—H30A | 109.5 |
C11—C12—C19 | 109.54 (18) | C29—C30—H30B | 109.5 |
C13—C12—C19 | 106.48 (17) | H30A—C30—H30B | 109.5 |
C11—C12—C26 | 106.10 (16) | C29—C30—H30C | 109.5 |
C13—C12—C26 | 111.64 (17) | H30A—C30—H30C | 109.5 |
C19—C12—C26 | 114.27 (16) | H30B—C30—H30C | 109.5 |
O6—C13—C8 | 121.07 (19) | C29—C31—H31A | 109.5 |
O6—C13—C12 | 116.68 (17) | C29—C31—H31B | 109.5 |
C8—C13—C12 | 122.23 (18) | H31A—C31—H31B | 109.5 |
C15—C14—C10 | 113.59 (18) | C29—C31—H31C | 109.5 |
C15—C14—H14A | 108.8 | H31A—C31—H31C | 109.5 |
C10—C14—H14A | 108.8 | H31B—C31—H31C | 109.5 |
C15—C14—H14B | 108.8 | C26—C32—H32A | 109.5 |
C10—C14—H14B | 108.8 | C26—C32—H32B | 109.5 |
H14A—C14—H14B | 107.7 | H32A—C32—H32B | 109.5 |
C16—C15—C14 | 127.4 (2) | C26—C32—H32C | 109.5 |
C16—C15—H15 | 116.3 | H32A—C32—H32C | 109.5 |
C14—C15—H15 | 116.3 | H32B—C32—H32C | 109.5 |
C15—C16—C18 | 125.2 (3) | C34—C33—C26 | 115.68 (18) |
C15—C16—C17 | 120.9 (3) | C34—C33—H33A | 108.4 |
C18—C16—C17 | 114.0 (2) | C26—C33—H33A | 108.4 |
C16—C17—H17A | 109.5 | C34—C33—H33B | 108.4 |
C16—C17—H17B | 109.5 | C26—C33—H33B | 108.4 |
H17A—C17—H17B | 109.5 | H33A—C33—H33B | 107.4 |
C16—C17—H17C | 109.5 | C35—C34—C33 | 111.06 (19) |
H17A—C17—H17C | 109.5 | C35—C34—H34A | 109.4 |
H17B—C17—H17C | 109.5 | C33—C34—H34A | 109.4 |
C16—C18—H18A | 109.5 | C35—C34—H34B | 109.4 |
C16—C18—H18B | 109.5 | C33—C34—H34B | 109.4 |
H18A—C18—H18B | 109.5 | H34A—C34—H34B | 108.0 |
C16—C18—H18C | 109.5 | C36—C35—C34 | 127.6 (2) |
H18A—C18—H18C | 109.5 | C36—C35—H35 | 116.2 |
H18B—C18—H18C | 109.5 | C34—C35—H35 | 116.2 |
C20—C19—C12 | 112.16 (16) | C35—C36—C38 | 123.6 (2) |
C20—C19—H19A | 109.2 | C35—C36—C37 | 120.9 (2) |
C12—C19—H19A | 109.2 | C38—C36—C37 | 115.5 (2) |
C20—C19—H19B | 109.2 | C36—C37—H37A | 109.5 |
C12—C19—H19B | 109.2 | C36—C37—H37B | 109.5 |
H19A—C19—H19B | 107.9 | H37A—C37—H37B | 109.5 |
C21—C20—C19 | 128.3 (2) | C36—C37—H37C | 109.5 |
C21—C20—H20 | 115.8 | H37A—C37—H37C | 109.5 |
C19—C20—H20 | 115.8 | H37B—C37—H37C | 109.5 |
C20—C21—C22 | 124.1 (2) | C36—C38—H38A | 109.5 |
C20—C21—C23 | 121.8 (2) | C36—C38—H38B | 109.5 |
C22—C21—C23 | 114.1 (2) | H38A—C38—H38B | 109.5 |
C21—C22—H22A | 109.5 | C36—C38—H38C | 109.5 |
C21—C22—H22B | 109.5 | H38A—C38—H38C | 109.5 |
H22A—C22—H22B | 109.5 | H38B—C38—H38C | 109.5 |
| | | |
C6—C1—C2—C3 | 1.6 (4) | C26—C12—C13—O6 | −80.1 (2) |
C1—C2—C3—O1A | −178.8 (2) | C11—C12—C13—C8 | −15.3 (3) |
C1—C2—C3—C4 | 1.6 (4) | C19—C12—C13—C8 | −133.2 (2) |
O1A—C3—C4—O2 | −1.6 (3) | C26—C12—C13—C8 | 101.4 (2) |
C2—C3—C4—O2 | 178.1 (2) | C11—C10—C14—C15 | 65.4 (2) |
O1A—C3—C4—C5 | 177.1 (2) | C9—C10—C14—C15 | −59.1 (2) |
C2—C3—C4—C5 | −3.2 (3) | C24—C10—C14—C15 | −178.62 (18) |
O2—C4—C5—C6 | −179.6 (2) | C10—C14—C15—C16 | 124.4 (3) |
C3—C4—C5—C6 | 1.7 (3) | C14—C15—C16—C18 | −0.9 (5) |
C2—C1—C6—C5 | −3.1 (3) | C14—C15—C16—C17 | 179.3 (3) |
C2—C1—C6—C7 | 179.2 (2) | C11—C12—C19—C20 | −66.6 (2) |
C4—C5—C6—C1 | 1.5 (3) | C13—C12—C19—C20 | 50.8 (2) |
C4—C5—C6—C7 | 179.0 (2) | C26—C12—C19—C20 | 174.53 (18) |
C1—C6—C7—O3A | 31.4 (3) | C12—C19—C20—C21 | −122.6 (2) |
C5—C6—C7—O3A | −146.2 (2) | C19—C20—C21—C22 | −1.8 (4) |
C1—C6—C7—C8 | −149.5 (2) | C19—C20—C21—C23 | 178.6 (2) |
C5—C6—C7—C8 | 32.9 (3) | C11—C10—C24—C25 | −55.1 (2) |
O3A—C7—C8—C13 | 4.7 (3) | C9—C10—C24—C25 | 64.3 (2) |
C6—C7—C8—C13 | −174.4 (2) | C14—C10—C24—C25 | −175.85 (17) |
O3A—C7—C8—C9 | −157.9 (2) | C10—C24—C25—C27 | −83.4 (2) |
C6—C7—C8—C9 | 23.0 (3) | C10—C24—C25—C26 | 50.3 (2) |
C13—C8—C9—O4 | −150.92 (19) | C24—C25—C26—C32 | −171.79 (15) |
C7—C8—C9—O4 | 11.7 (3) | C27—C25—C26—C32 | −39.4 (2) |
C13—C8—C9—C10 | 24.5 (3) | C24—C25—C26—C33 | 69.7 (2) |
C7—C8—C9—C10 | −172.91 (19) | C27—C25—C26—C33 | −157.99 (17) |
O4—C9—C10—C11 | −172.73 (17) | C24—C25—C26—C12 | −48.6 (2) |
C8—C9—C10—C11 | 11.7 (3) | C27—C25—C26—C12 | 83.8 (2) |
O4—C9—C10—C14 | −47.9 (2) | C11—C12—C26—C32 | 178.64 (16) |
C8—C9—C10—C14 | 136.48 (19) | C13—C12—C26—C32 | 60.3 (2) |
O4—C9—C10—C24 | 72.6 (2) | C19—C12—C26—C32 | −60.6 (2) |
C8—C9—C10—C24 | −103.0 (2) | C11—C12—C26—C33 | −64.6 (2) |
C9—C10—C11—O5 | 134.6 (2) | C13—C12—C26—C33 | 177.14 (17) |
C14—C10—C11—O5 | 11.4 (3) | C19—C12—C26—C33 | 56.2 (2) |
C24—C10—C11—O5 | −108.1 (2) | C11—C12—C26—C25 | 55.2 (2) |
C9—C10—C11—C12 | −51.6 (2) | C13—C12—C26—C25 | −63.1 (2) |
C14—C10—C11—C12 | −174.77 (16) | C19—C12—C26—C25 | 175.99 (17) |
C24—C10—C11—C12 | 65.7 (2) | C24—C25—C27—C28 | −59.3 (2) |
O5—C11—C12—C13 | −133.6 (2) | C26—C25—C27—C28 | 169.03 (17) |
C10—C11—C12—C13 | 52.6 (2) | C25—C27—C28—C29 | 140.8 (2) |
O5—C11—C12—C19 | −17.6 (3) | C27—C28—C29—C30 | −2.6 (4) |
C10—C11—C12—C19 | 168.63 (15) | C27—C28—C29—C31 | 176.2 (2) |
O5—C11—C12—C26 | 106.2 (2) | C32—C26—C33—C34 | −71.1 (2) |
C10—C11—C12—C26 | −67.6 (2) | C25—C26—C33—C34 | 49.8 (2) |
C7—C8—C13—O6 | −4.7 (3) | C12—C26—C33—C34 | 169.90 (18) |
C9—C8—C13—O6 | 158.98 (19) | C26—C33—C34—C35 | 160.03 (18) |
C7—C8—C13—C12 | 173.66 (19) | C33—C34—C35—C36 | 94.7 (3) |
C9—C8—C13—C12 | −22.6 (3) | C34—C35—C36—C38 | 4.3 (5) |
C11—C12—C13—O6 | 163.19 (18) | C34—C35—C36—C37 | −178.4 (2) |
C19—C12—C13—O6 | 45.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O4i | 0.84 | 1.94 | 2.7732 (19) | 171 |
O3A—H3O···O6 | 0.84 | 1.62 | 2.3934 (18) | 153 |
Symmetry code: (i) x+1/2, −y−1/2, −z. |