Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060965/sj2433sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060965/sj2433Isup2.hkl |
CCDC reference: 673075
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.011 Å
- R factor = 0.078
- wR factor = 0.237
- Data-to-parameter ratio = 7.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C6A - C21A .. 11.44 su PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.53 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C18 - C19 .. 5.37 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O5A - C9A .. 6.06 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O6A - C18A .. 6.12 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C1A - C11A .. 5.88 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C4A - C10A .. 5.20 su
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 25.01 From the CIF: _reflns_number_total 3556 Count of symmetry unique reflns 3556 Completeness (_total/calc) 100.00% 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 C4 ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9A ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A ... S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11A ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 ... R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15A ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1896
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 16 ALERT level G = General alerts; check 16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
For information on ring puckering analysis, see: Cremer & Pople (1975). For previous isolation of the title compound, see: Sun et al. (1988).
2 kg of dried powder from the whole plant, Rabdosia var lophanthoides Hara, was soaked three times with 95% EtOH at room temperature. The ethanolic extracts were evaporated under reduced pressure and the residue was successively fractionated with petroleum ether, EtOAc and n-BuOH. The residue of the petroleum ether fraction was subjected to column chromatography over silica gel. The column was eluted with a petroleum ether-EtOAc mixture and the title compound isolated. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.
H atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.96 Å (CH3), 0.97 Å (CH2) and 0.98(CH) and with the temperature factors Uiso= 1.5 Ueq(CH3) and 1.2 Ueq(CH2, CH).
In the absence of significant anomalous scattering, the absolute configuration could not be reliably determined from the X-ray analyses and the Friedel pairs were merged; stereochemistry was assigned following the work of Sun et al. (1988).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C20H26O6 | F(000) = 1552 |
Mr = 362.41 | Dx = 1.340 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2028 reflections |
a = 12.2614 (15) Å | θ = 2.2–18.1° |
b = 15.6668 (18) Å | µ = 0.10 mm−1 |
c = 18.697 (2) Å | T = 298 K |
V = 3591.7 (8) Å3 | Prismatic, colorless |
Z = 8 | 0.41 × 0.30 × 0.28 mm |
Bruker SMART CCD area-detector diffractometer | 3556 independent reflections |
Radiation source: fine-focus sealed tube | 1970 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −13→14 |
Tmin = 0.961, Tmax = 0.973 | k = −16→18 |
17440 measured reflections | l = −22→18 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.237 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1062P)2 + 2.5318P] where P = (Fo2 + 2Fc2)/3 |
3556 reflections | (Δ/σ)max = 0.001 |
472 parameters | Δρmax = 0.54 e Å−3 |
1896 restraints | Δρmin = −0.56 e Å−3 |
C20H26O6 | V = 3591.7 (8) Å3 |
Mr = 362.41 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.2614 (15) Å | µ = 0.10 mm−1 |
b = 15.6668 (18) Å | T = 298 K |
c = 18.697 (2) Å | 0.41 × 0.30 × 0.28 mm |
Bruker SMART CCD area-detector diffractometer | 3556 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 1970 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.973 | Rint = 0.084 |
17440 measured reflections |
R[F2 > 2σ(F2)] = 0.078 | 1896 restraints |
wR(F2) = 0.237 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.54 e Å−3 |
3556 reflections | Δρmin = −0.56 e Å−3 |
472 parameters |
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 | ||
O1 | 0.3555 (6) | 0.3465 (4) | −0.0342 (3) | 0.0854 (18) | |
O1A | 0.1460 (6) | 0.4505 (4) | 0.0174 (3) | 0.0770 (16) | |
O2 | 0.2908 (4) | 0.4019 (4) | 0.1997 (3) | 0.0642 (14) | |
O2A | 0.2089 (4) | 0.7286 (3) | 0.0555 (3) | 0.0599 (13) | |
O3 | 0.2473 (5) | 0.5342 (4) | 0.2199 (4) | 0.089 (2) | |
O3A | 0.2729 (4) | 0.7432 (4) | 0.1633 (3) | 0.0644 (15) | |
O4 | 0.4497 (6) | 0.6058 (3) | 0.1203 (3) | 0.0697 (16) | |
H4 | 0.4029 | 0.6414 | 0.1108 | 0.105* | |
O4A | 0.0623 (5) | 0.6303 (4) | 0.2404 (3) | 0.0615 (15) | |
H4A | 0.1224 | 0.6081 | 0.2357 | 0.092* | |
O5 | 0.5642 (5) | 0.3563 (4) | 0.2942 (3) | 0.0704 (16) | |
H5 | 0.6109 | 0.3235 | 0.3092 | 0.106* | |
O5A | −0.0730 (4) | 0.8390 (3) | 0.0395 (3) | 0.0554 (14) | |
H5B | −0.1236 | 0.8706 | 0.0284 | 0.083* | |
O6 | 0.2848 (6) | 0.2872 (5) | 0.0616 (4) | 0.105 (2) | |
O6A | 0.2237 (5) | 0.5683 (4) | −0.0221 (4) | 0.0778 (18) | |
C1 | 0.3744 (7) | 0.3381 (5) | 0.1955 (5) | 0.0627 (19) | |
H1A | 0.3433 | 0.2858 | 0.1767 | 0.075* | |
H1B | 0.4017 | 0.3263 | 0.2432 | 0.075* | |
C1A | 0.1156 (6) | 0.7223 (5) | 0.0093 (4) | 0.0555 (18) | |
H1C | 0.1384 | 0.6989 | −0.0364 | 0.067* | |
H1D | 0.0868 | 0.7791 | 0.0007 | 0.067* | |
C3 | 0.3182 (7) | 0.4818 (6) | 0.2136 (4) | 0.0581 (19) | |
C3A | 0.1937 (7) | 0.7400 (5) | 0.1253 (5) | 0.0496 (17) | |
C4 | 0.4375 (6) | 0.5041 (5) | 0.2221 (4) | 0.0453 (16) | |
C4A | 0.0797 (6) | 0.7523 (5) | 0.1533 (4) | 0.0445 (15) | |
C5 | 0.4566 (7) | 0.5961 (5) | 0.1943 (4) | 0.0566 (18) | |
H5A | 0.4037 | 0.6343 | 0.2170 | 0.068* | |
C5A | 0.0716 (7) | 0.7189 (5) | 0.2313 (4) | 0.0545 (17) | |
H5C | 0.1354 | 0.7390 | 0.2581 | 0.065* | |
C6 | 0.5690 (7) | 0.6152 (5) | 0.2241 (4) | 0.0558 (18) | |
C6A | −0.0275 (7) | 0.7649 (5) | 0.2585 (4) | 0.0578 (19) | |
C7 | 0.5801 (8) | 0.5631 (5) | 0.2931 (4) | 0.0617 (19) | |
H7 | 0.5992 | 0.5991 | 0.3341 | 0.074* | |
C7A | −0.0466 (7) | 0.8426 (5) | 0.2124 (4) | 0.0601 (19) | |
H7A | −0.0576 | 0.8938 | 0.2416 | 0.072* | |
C8 | 0.6638 (7) | 0.4907 (5) | 0.2817 (4) | 0.0592 (19) | |
H8A | 0.7243 | 0.5119 | 0.2534 | 0.071* | |
H8B | 0.6923 | 0.4726 | 0.3277 | 0.071* | |
C8A | −0.1419 (6) | 0.8280 (5) | 0.1616 (4) | 0.0501 (17) | |
H8C | −0.1726 | 0.8828 | 0.1482 | 0.060* | |
H8D | −0.1981 | 0.7959 | 0.1862 | 0.060* | |
C9 | 0.6122 (6) | 0.4138 (5) | 0.2436 (4) | 0.0544 (18) | |
H9 | 0.6700 | 0.3832 | 0.2180 | 0.065* | |
C9A | −0.1089 (6) | 0.7800 (5) | 0.0939 (4) | 0.0451 (16) | |
H9A | −0.1730 | 0.7494 | 0.0758 | 0.054* | |
C10 | 0.5252 (6) | 0.4415 (4) | 0.1887 (4) | 0.0416 (15) | |
H10 | 0.5641 | 0.4747 | 0.1523 | 0.050* | |
C10A | −0.0175 (5) | 0.7145 (4) | 0.1078 (3) | 0.0364 (14) | |
H10A | −0.0504 | 0.6702 | 0.1380 | 0.044* | |
C11 | 0.4689 (6) | 0.3660 (5) | 0.1479 (4) | 0.0481 (16) | |
C11A | 0.0259 (6) | 0.6667 (4) | 0.0400 (4) | 0.0415 (14) | |
C12 | 0.5449 (7) | 0.2881 (5) | 0.1368 (5) | 0.0625 (19) | |
H12A | 0.5762 | 0.2723 | 0.1826 | 0.075* | |
H12B | 0.5016 | 0.2403 | 0.1202 | 0.075* | |
C12A | −0.0584 (6) | 0.6565 (5) | −0.0210 (4) | 0.0505 (17) | |
H12C | −0.0933 | 0.7112 | −0.0293 | 0.061* | |
H12D | −0.0203 | 0.6407 | −0.0645 | 0.061* | |
C13 | 0.6370 (7) | 0.3038 (6) | 0.0839 (5) | 0.068 (2) | |
H13A | 0.6829 | 0.3500 | 0.1007 | 0.082* | |
H13B | 0.6816 | 0.2529 | 0.0797 | 0.082* | |
C13A | −0.1465 (7) | 0.5897 (5) | −0.0059 (4) | 0.0597 (19) | |
H13C | −0.1879 | 0.6060 | 0.0362 | 0.072* | |
H13D | −0.1963 | 0.5863 | −0.0461 | 0.072* | |
C14 | 0.5892 (7) | 0.3265 (6) | 0.0117 (5) | 0.073 (2) | |
H14A | 0.5464 | 0.2786 | −0.0056 | 0.088* | |
H14B | 0.6482 | 0.3358 | −0.0219 | 0.088* | |
C14A | −0.0931 (7) | 0.5037 (5) | 0.0062 (5) | 0.063 (2) | |
H14C | −0.0528 | 0.4877 | −0.0364 | 0.076* | |
H14D | −0.1492 | 0.4611 | 0.0141 | 0.076* | |
C15 | 0.5169 (7) | 0.4059 (5) | 0.0133 (4) | 0.0534 (18) | |
C15A | −0.0155 (6) | 0.5047 (5) | 0.0704 (4) | 0.0508 (17) | |
C16 | 0.4396 (8) | 0.4081 (6) | −0.0503 (4) | 0.074 (2) | |
H16A | 0.4085 | 0.4647 | −0.0560 | 0.089* | |
H16B | 0.4776 | 0.3928 | −0.0939 | 0.089* | |
C16A | 0.0601 (8) | 0.4272 (5) | 0.0665 (5) | 0.070 (2) | |
H16C | 0.0899 | 0.4143 | 0.1134 | 0.084* | |
H16D | 0.0208 | 0.3776 | 0.0492 | 0.084* | |
C18 | 0.3476 (8) | 0.3369 (7) | 0.0369 (5) | 0.072 (2) | |
C18A | 0.1552 (8) | 0.5350 (6) | 0.0136 (5) | 0.0597 (19) | |
C19 | 0.4297 (6) | 0.3962 (5) | 0.0736 (4) | 0.0485 (16) | |
H19 | 0.3944 | 0.4518 | 0.0799 | 0.058* | |
C19A | 0.0699 (6) | 0.5773 (4) | 0.0622 (4) | 0.0431 (15) | |
H19A | 0.1043 | 0.5845 | 0.1092 | 0.052* | |
C20 | 0.4656 (7) | 0.5224 (5) | 0.3016 (4) | 0.0589 (18) | |
H20A | 0.4142 | 0.5619 | 0.3231 | 0.071* | |
H20B | 0.4683 | 0.4704 | 0.3297 | 0.071* | |
C20A | 0.0601 (7) | 0.8482 (5) | 0.1686 (4) | 0.0578 (18) | |
H20C | 0.1190 | 0.8730 | 0.1963 | 0.069* | |
H20D | 0.0502 | 0.8806 | 0.1248 | 0.069* | |
C21 | 0.6457 (8) | 0.6594 (6) | 0.1925 (6) | 0.081 (3) | |
H21A | 0.6335 | 0.6825 | 0.1474 | 0.098* | |
H21B | 0.7123 | 0.6677 | 0.2152 | 0.098* | |
C21A | −0.0921 (8) | 0.7372 (7) | 0.3096 (5) | 0.091 (3) | |
H21C | −0.0777 | 0.6854 | 0.3319 | 0.109* | |
H21D | −0.1521 | 0.7695 | 0.3234 | 0.109* | |
C22 | 0.5889 (7) | 0.4864 (6) | 0.0139 (5) | 0.065 (2) | |
H22A | 0.6405 | 0.4827 | 0.0524 | 0.098* | |
H22B | 0.5439 | 0.5360 | 0.0204 | 0.098* | |
H22C | 0.6273 | 0.4908 | −0.0307 | 0.098* | |
C22A | −0.0819 (8) | 0.5005 (5) | 0.1404 (4) | 0.066 (2) | |
H22D | −0.1183 | 0.4464 | 0.1434 | 0.099* | |
H22E | −0.1350 | 0.5455 | 0.1408 | 0.099* | |
H22F | −0.0337 | 0.5069 | 0.1805 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.076 (4) | 0.102 (4) | 0.077 (4) | −0.006 (4) | −0.011 (3) | −0.034 (3) |
O1A | 0.081 (4) | 0.056 (3) | 0.094 (4) | 0.013 (3) | −0.034 (3) | 0.002 (3) |
O2 | 0.045 (3) | 0.069 (3) | 0.079 (3) | 0.006 (3) | 0.008 (3) | 0.010 (3) |
O2A | 0.038 (3) | 0.070 (3) | 0.072 (3) | −0.011 (2) | −0.007 (3) | −0.002 (3) |
O3 | 0.057 (4) | 0.091 (4) | 0.118 (5) | 0.034 (4) | 0.006 (4) | −0.002 (4) |
O3A | 0.033 (3) | 0.067 (4) | 0.094 (4) | −0.005 (3) | 0.015 (3) | −0.004 (3) |
O4 | 0.097 (4) | 0.061 (3) | 0.052 (3) | 0.015 (3) | −0.010 (3) | 0.012 (3) |
O4A | 0.059 (3) | 0.073 (4) | 0.053 (3) | 0.020 (3) | −0.004 (3) | −0.010 (3) |
O5 | 0.064 (3) | 0.077 (4) | 0.070 (3) | 0.021 (3) | 0.003 (3) | 0.031 (3) |
O5A | 0.055 (3) | 0.056 (3) | 0.056 (3) | 0.006 (3) | −0.006 (3) | −0.017 (3) |
O6 | 0.092 (5) | 0.104 (5) | 0.119 (5) | −0.047 (4) | −0.003 (4) | −0.014 (4) |
O6A | 0.060 (4) | 0.080 (4) | 0.093 (4) | 0.002 (3) | −0.037 (4) | 0.000 (3) |
C1 | 0.059 (4) | 0.054 (4) | 0.074 (4) | −0.005 (4) | 0.010 (4) | 0.009 (4) |
C1A | 0.049 (4) | 0.061 (4) | 0.057 (4) | 0.005 (3) | −0.008 (3) | −0.008 (3) |
C3 | 0.064 (4) | 0.059 (4) | 0.051 (4) | 0.010 (4) | 0.006 (4) | 0.010 (3) |
C3A | 0.042 (4) | 0.041 (4) | 0.065 (4) | −0.004 (3) | 0.005 (3) | −0.002 (3) |
C4 | 0.042 (3) | 0.047 (3) | 0.047 (3) | 0.005 (3) | 0.006 (3) | 0.001 (3) |
C4A | 0.038 (3) | 0.050 (3) | 0.045 (3) | 0.004 (3) | 0.007 (3) | 0.004 (3) |
C5 | 0.070 (4) | 0.049 (4) | 0.051 (4) | 0.018 (3) | −0.005 (4) | −0.003 (3) |
C5A | 0.047 (3) | 0.066 (4) | 0.051 (4) | 0.015 (3) | 0.011 (3) | 0.009 (3) |
C6 | 0.067 (4) | 0.044 (4) | 0.057 (4) | 0.009 (4) | −0.002 (4) | −0.009 (3) |
C6A | 0.056 (4) | 0.075 (4) | 0.042 (4) | 0.012 (4) | 0.014 (4) | 0.011 (3) |
C7 | 0.080 (4) | 0.062 (4) | 0.043 (4) | 0.003 (4) | −0.004 (4) | −0.013 (3) |
C7A | 0.058 (4) | 0.063 (4) | 0.059 (4) | 0.012 (4) | 0.011 (4) | 0.022 (3) |
C8 | 0.050 (4) | 0.073 (4) | 0.055 (4) | 0.008 (4) | −0.007 (4) | 0.005 (4) |
C8A | 0.041 (4) | 0.056 (4) | 0.053 (4) | 0.008 (3) | 0.001 (3) | −0.006 (3) |
C9 | 0.049 (4) | 0.056 (4) | 0.058 (4) | 0.014 (3) | 0.008 (3) | 0.007 (3) |
C9A | 0.041 (3) | 0.046 (4) | 0.048 (3) | −0.002 (3) | 0.001 (3) | −0.004 (3) |
C10 | 0.040 (3) | 0.041 (3) | 0.044 (3) | 0.010 (3) | 0.003 (3) | 0.008 (3) |
C10A | 0.029 (3) | 0.041 (3) | 0.039 (3) | −0.003 (3) | −0.001 (3) | −0.004 (3) |
C11 | 0.042 (3) | 0.042 (3) | 0.060 (3) | 0.006 (3) | 0.010 (3) | 0.000 (3) |
C11A | 0.034 (3) | 0.045 (3) | 0.045 (3) | −0.007 (3) | −0.003 (3) | −0.004 (3) |
C12 | 0.066 (4) | 0.045 (4) | 0.076 (4) | 0.008 (4) | 0.004 (4) | −0.003 (3) |
C12A | 0.050 (4) | 0.062 (4) | 0.039 (3) | 0.002 (3) | 0.002 (3) | 0.000 (3) |
C13 | 0.057 (4) | 0.066 (4) | 0.082 (5) | 0.023 (4) | 0.009 (4) | −0.005 (4) |
C13A | 0.053 (4) | 0.071 (4) | 0.055 (4) | −0.004 (4) | 0.008 (4) | 0.008 (4) |
C14 | 0.063 (4) | 0.081 (5) | 0.077 (4) | 0.005 (4) | 0.009 (4) | −0.021 (4) |
C14A | 0.063 (4) | 0.058 (4) | 0.068 (4) | −0.012 (4) | −0.008 (4) | 0.009 (4) |
C15 | 0.051 (4) | 0.061 (4) | 0.047 (4) | 0.010 (3) | 0.004 (3) | −0.010 (3) |
C15A | 0.052 (4) | 0.043 (4) | 0.057 (4) | 0.004 (3) | −0.011 (3) | −0.001 (3) |
C16 | 0.066 (5) | 0.098 (5) | 0.057 (4) | 0.015 (5) | 0.005 (4) | −0.016 (4) |
C16A | 0.072 (5) | 0.050 (4) | 0.089 (5) | 0.001 (4) | −0.024 (4) | −0.004 (4) |
C18 | 0.060 (4) | 0.078 (4) | 0.078 (4) | 0.003 (4) | −0.002 (4) | −0.009 (4) |
C18A | 0.053 (4) | 0.061 (4) | 0.065 (4) | 0.010 (4) | −0.006 (4) | −0.001 (4) |
C19 | 0.043 (3) | 0.047 (3) | 0.055 (3) | −0.005 (3) | 0.002 (3) | −0.008 (3) |
C19A | 0.037 (3) | 0.051 (3) | 0.041 (3) | 0.000 (3) | −0.005 (3) | 0.001 (3) |
C20 | 0.069 (4) | 0.061 (4) | 0.046 (3) | 0.027 (3) | 0.009 (3) | 0.002 (3) |
C20A | 0.052 (4) | 0.053 (4) | 0.069 (4) | −0.002 (3) | 0.013 (3) | 0.008 (3) |
C21 | 0.088 (6) | 0.069 (6) | 0.087 (6) | −0.019 (5) | −0.007 (6) | −0.003 (5) |
C21A | 0.090 (6) | 0.123 (7) | 0.059 (5) | 0.054 (6) | −0.012 (5) | −0.023 (5) |
C22 | 0.059 (5) | 0.075 (5) | 0.061 (5) | −0.005 (4) | 0.012 (4) | 0.007 (4) |
C22A | 0.069 (5) | 0.061 (5) | 0.069 (5) | −0.004 (4) | −0.022 (4) | −0.009 (4) |
O1—C18 | 1.343 (11) | C9A—C10A | 1.543 (9) |
O1—C16 | 1.444 (11) | C9A—H9A | 0.9800 |
O1A—C18A | 1.330 (10) | C10—C11 | 1.568 (10) |
O1A—C16A | 1.445 (11) | C10—H10 | 0.9800 |
O2—C3 | 1.323 (10) | C10A—C11A | 1.566 (9) |
O2—C1 | 1.432 (10) | C10A—H10A | 0.9800 |
O2A—C3A | 1.330 (9) | C11—C19 | 1.544 (10) |
O2A—C1A | 1.438 (9) | C11—C12 | 1.549 (10) |
O3—C3 | 1.201 (10) | C11A—C12A | 1.548 (10) |
O3A—C3A | 1.204 (9) | C11A—C19A | 1.556 (10) |
O4—C5 | 1.394 (9) | C12—C13 | 1.522 (12) |
O4—H4 | 0.8200 | C12—H12A | 0.9700 |
O4A—C5A | 1.404 (9) | C12—H12B | 0.9700 |
O4A—H4A | 0.8200 | C12A—C13A | 1.530 (11) |
O5—C9 | 1.433 (9) | C12A—H12C | 0.9700 |
O5—H5 | 0.8200 | C12A—H12D | 0.9700 |
O5A—C9A | 1.443 (8) | C13—C14 | 1.515 (12) |
O5A—H5B | 0.8200 | C13—H13A | 0.9700 |
O6—C18 | 1.188 (11) | C13—H13B | 0.9700 |
O6A—C18A | 1.192 (10) | C13A—C14A | 1.515 (11) |
C1—C11 | 1.526 (10) | C13A—H13C | 0.9700 |
C1—H1A | 0.9700 | C13A—H13D | 0.9700 |
C1—H1B | 0.9700 | C14—C15 | 1.528 (11) |
C1A—C11A | 1.516 (10) | C14—H14A | 0.9700 |
C1A—H1C | 0.9700 | C14—H14B | 0.9700 |
C1A—H1D | 0.9700 | C14A—C15A | 1.532 (11) |
C3—C4 | 1.512 (12) | C14A—H14C | 0.9700 |
C3A—C4A | 1.504 (10) | C14A—H14D | 0.9700 |
C4—C5 | 1.551 (11) | C15—C16 | 1.521 (11) |
C4—C20 | 1.553 (10) | C15—C22 | 1.539 (11) |
C4—C10 | 1.584 (10) | C15—C19 | 1.561 (10) |
C4A—C20A | 1.548 (11) | C15A—C16A | 1.529 (11) |
C4A—C5A | 1.554 (10) | C15A—C22A | 1.542 (11) |
C4A—C10A | 1.579 (10) | C15A—C19A | 1.554 (10) |
C5—C6 | 1.516 (12) | C16—H16A | 0.9700 |
C5—H5A | 0.9800 | C16—H16B | 0.9700 |
C5A—C6A | 1.501 (11) | C16A—H16C | 0.9700 |
C5A—H5C | 0.9800 | C16A—H16D | 0.9700 |
C6—C21 | 1.308 (12) | C18—C19 | 1.531 (12) |
C6—C7 | 1.533 (11) | C18A—C19A | 1.537 (11) |
C6A—C21A | 1.314 (12) | C19—H19 | 0.9800 |
C6A—C7A | 1.510 (11) | C19A—H19A | 0.9800 |
C7—C8 | 1.544 (11) | C20—H20A | 0.9700 |
C7—C20 | 1.550 (12) | C20—H20B | 0.9700 |
C7—H7 | 0.9800 | C20A—H20C | 0.9700 |
C7A—C8A | 1.523 (11) | C20A—H20D | 0.9700 |
C7A—C20A | 1.546 (11) | C21—H21A | 0.9300 |
C7A—H7A | 0.9800 | C21—H21B | 0.9300 |
C8—C9 | 1.536 (11) | C21A—H21C | 0.9300 |
C8—H8A | 0.9700 | C21A—H21D | 0.9300 |
C8—H8B | 0.9700 | C22—H22A | 0.9600 |
C8A—C9A | 1.527 (10) | C22—H22B | 0.9600 |
C8A—H8C | 0.9700 | C22—H22C | 0.9600 |
C8A—H8D | 0.9700 | C22A—H22D | 0.9600 |
C9—C10 | 1.543 (10) | C22A—H22E | 0.9600 |
C9—H9 | 0.9800 | C22A—H22F | 0.9600 |
C18—O1—C16 | 109.4 (7) | C12A—C11A—C19A | 109.6 (6) |
C18A—O1A—C16A | 110.4 (7) | C1A—C11A—C10A | 106.2 (6) |
C3—O2—C1 | 119.3 (7) | C12A—C11A—C10A | 114.8 (6) |
C3A—O2A—C1A | 119.2 (6) | C19A—C11A—C10A | 109.3 (5) |
C5—O4—H4 | 109.5 | C13—C12—C11 | 114.0 (7) |
C5A—O4A—H4A | 109.5 | C13—C12—H12A | 108.8 |
C9—O5—H5 | 109.5 | C11—C12—H12A | 108.8 |
C9A—O5A—H5B | 109.5 | C13—C12—H12B | 108.8 |
O2—C1—C11 | 112.1 (6) | C11—C12—H12B | 108.8 |
O2—C1—H1A | 109.2 | H12A—C12—H12B | 107.7 |
C11—C1—H1A | 109.2 | C13A—C12A—C11A | 114.0 (6) |
O2—C1—H1B | 109.2 | C13A—C12A—H12C | 108.8 |
C11—C1—H1B | 109.2 | C11A—C12A—H12C | 108.8 |
H1A—C1—H1B | 107.9 | C13A—C12A—H12D | 108.8 |
O2A—C1A—C11A | 112.9 (6) | C11A—C12A—H12D | 108.8 |
O2A—C1A—H1C | 109.0 | H12C—C12A—H12D | 107.7 |
C11A—C1A—H1C | 109.0 | C14—C13—C12 | 109.3 (7) |
O2A—C1A—H1D | 109.0 | C14—C13—H13A | 109.8 |
C11A—C1A—H1D | 109.0 | C12—C13—H13A | 109.8 |
H1C—C1A—H1D | 107.8 | C14—C13—H13B | 109.8 |
O3—C3—O2 | 118.9 (8) | C12—C13—H13B | 109.8 |
O3—C3—C4 | 122.1 (8) | H13A—C13—H13B | 108.3 |
O2—C3—C4 | 119.0 (7) | C14A—C13A—C12A | 109.3 (7) |
O3A—C3A—O2A | 118.1 (7) | C14A—C13A—H13C | 109.8 |
O3A—C3A—C4A | 122.6 (7) | C12A—C13A—H13C | 109.8 |
O2A—C3A—C4A | 119.2 (7) | C14A—C13A—H13D | 109.8 |
C3—C4—C5 | 109.0 (6) | C12A—C13A—H13D | 109.8 |
C3—C4—C20 | 111.0 (6) | H13C—C13A—H13D | 108.3 |
C5—C4—C20 | 96.6 (6) | C13—C14—C15 | 113.4 (7) |
C3—C4—C10 | 118.2 (7) | C13—C14—H14A | 108.9 |
C5—C4—C10 | 109.9 (6) | C15—C14—H14A | 108.9 |
C20—C4—C10 | 110.0 (6) | C13—C14—H14B | 108.9 |
C3A—C4A—C20A | 109.5 (6) | C15—C14—H14B | 108.9 |
C3A—C4A—C5A | 110.0 (6) | H14A—C14—H14B | 107.7 |
C20A—C4A—C5A | 98.2 (6) | C13A—C14A—C15A | 112.1 (7) |
C3A—C4A—C10A | 117.8 (6) | C13A—C14A—H14C | 109.2 |
C20A—C4A—C10A | 110.3 (6) | C15A—C14A—H14C | 109.2 |
C5A—C4A—C10A | 109.3 (6) | C13A—C14A—H14D | 109.2 |
O4—C5—C6 | 113.5 (7) | C15A—C14A—H14D | 109.2 |
O4—C5—C4 | 115.1 (6) | H14C—C14A—H14D | 107.9 |
C6—C5—C4 | 101.4 (6) | C16—C15—C14 | 111.3 (7) |
O4—C5—H5A | 108.8 | C16—C15—C22 | 110.1 (7) |
C6—C5—H5A | 108.8 | C14—C15—C22 | 109.6 (7) |
C4—C5—H5A | 108.8 | C16—C15—C19 | 98.0 (6) |
O4A—C5A—C6A | 111.6 (7) | C14—C15—C19 | 109.4 (7) |
O4A—C5A—C4A | 116.8 (6) | C22—C15—C19 | 117.9 (6) |
C6A—C5A—C4A | 102.0 (6) | C16A—C15A—C14A | 109.4 (7) |
O4A—C5A—H5C | 108.7 | C16A—C15A—C22A | 109.0 (7) |
C6A—C5A—H5C | 108.7 | C14A—C15A—C22A | 109.7 (7) |
C4A—C5A—H5C | 108.7 | C16A—C15A—C19A | 99.7 (6) |
C21—C6—C5 | 126.3 (8) | C14A—C15A—C19A | 110.4 (6) |
C21—C6—C7 | 126.7 (8) | C22A—C15A—C19A | 118.1 (6) |
C5—C6—C7 | 106.6 (7) | O1—C16—C15 | 105.5 (7) |
C21A—C6A—C5A | 125.1 (8) | O1—C16—H16A | 110.6 |
C21A—C6A—C7A | 126.0 (8) | C15—C16—H16A | 110.6 |
C5A—C6A—C7A | 108.6 (6) | O1—C16—H16B | 110.6 |
C6—C7—C8 | 109.5 (6) | C15—C16—H16B | 110.6 |
C6—C7—C20 | 103.0 (7) | H16A—C16—H16B | 108.8 |
C8—C7—C20 | 108.3 (6) | O1A—C16A—C15A | 105.8 (7) |
C6—C7—H7 | 111.9 | O1A—C16A—H16C | 110.6 |
C8—C7—H7 | 111.9 | C15A—C16A—H16C | 110.6 |
C20—C7—H7 | 111.9 | O1A—C16A—H16D | 110.6 |
C6A—C7A—C8A | 110.8 (7) | C15A—C16A—H16D | 110.6 |
C6A—C7A—C20A | 102.6 (6) | H16C—C16A—H16D | 108.7 |
C8A—C7A—C20A | 109.1 (6) | O6—C18—O1 | 120.3 (10) |
C6A—C7A—H7A | 111.4 | O6—C18—C19 | 130.6 (9) |
C8A—C7A—H7A | 111.4 | O1—C18—C19 | 109.2 (8) |
C20A—C7A—H7A | 111.4 | O6A—C18A—O1A | 121.7 (9) |
C9—C8—C7 | 111.5 (7) | O6A—C18A—C19A | 128.5 (8) |
C9—C8—H8A | 109.3 | O1A—C18A—C19A | 109.8 (8) |
C7—C8—H8A | 109.3 | C18—C19—C11 | 114.9 (7) |
C9—C8—H8B | 109.3 | C18—C19—C15 | 100.8 (6) |
C7—C8—H8B | 109.3 | C11—C19—C15 | 117.7 (6) |
H8A—C8—H8B | 108.0 | C18—C19—H19 | 107.6 |
C7A—C8A—C9A | 112.8 (6) | C11—C19—H19 | 107.6 |
C7A—C8A—H8C | 109.0 | C15—C19—H19 | 107.6 |
C9A—C8A—H8C | 109.0 | C18A—C19A—C15A | 101.6 (6) |
C7A—C8A—H8D | 109.0 | C18A—C19A—C11A | 117.7 (6) |
C9A—C8A—H8D | 109.0 | C15A—C19A—C11A | 116.8 (6) |
H8C—C8A—H8D | 107.8 | C18A—C19A—H19A | 106.6 |
O5—C9—C8 | 110.8 (6) | C15A—C19A—H19A | 106.6 |
O5—C9—C10 | 109.4 (6) | C11A—C19A—H19A | 106.6 |
C8—C9—C10 | 111.9 (6) | C7—C20—C4 | 100.3 (6) |
O5—C9—H9 | 108.2 | C7—C20—H20A | 111.7 |
C8—C9—H9 | 108.2 | C4—C20—H20A | 111.7 |
C10—C9—H9 | 108.2 | C7—C20—H20B | 111.7 |
O5A—C9A—C8A | 110.4 (6) | C4—C20—H20B | 111.7 |
O5A—C9A—C10A | 108.9 (5) | H20A—C20—H20B | 109.5 |
C8A—C9A—C10A | 112.4 (6) | C7A—C20A—C4A | 100.0 (6) |
O5A—C9A—H9A | 108.4 | C7A—C20A—H20C | 111.8 |
C8A—C9A—H9A | 108.4 | C4A—C20A—H20C | 111.8 |
C10A—C9A—H9A | 108.4 | C7A—C20A—H20D | 111.8 |
C9—C10—C11 | 114.6 (6) | C4A—C20A—H20D | 111.8 |
C9—C10—C4 | 112.4 (6) | H20C—C20A—H20D | 109.5 |
C11—C10—C4 | 111.1 (6) | C6—C21—H21A | 120.0 |
C9—C10—H10 | 106.0 | C6—C21—H21B | 120.0 |
C11—C10—H10 | 106.0 | H21A—C21—H21B | 120.0 |
C4—C10—H10 | 106.0 | C6A—C21A—H21C | 120.0 |
C9A—C10A—C11A | 115.3 (5) | C6A—C21A—H21D | 120.0 |
C9A—C10A—C4A | 112.9 (5) | H21C—C21A—H21D | 120.0 |
C11A—C10A—C4A | 111.1 (5) | C15—C22—H22A | 109.5 |
C9A—C10A—H10A | 105.5 | C15—C22—H22B | 109.5 |
C11A—C10A—H10A | 105.5 | H22A—C22—H22B | 109.5 |
C4A—C10A—H10A | 105.5 | C15—C22—H22C | 109.5 |
C1—C11—C19 | 112.1 (6) | H22A—C22—H22C | 109.5 |
C1—C11—C12 | 108.0 (6) | H22B—C22—H22C | 109.5 |
C19—C11—C12 | 108.0 (6) | C15A—C22A—H22D | 109.5 |
C1—C11—C10 | 105.5 (6) | C15A—C22A—H22E | 109.5 |
C19—C11—C10 | 110.1 (6) | H22D—C22A—H22E | 109.5 |
C12—C11—C10 | 113.2 (6) | C15A—C22A—H22F | 109.5 |
C1A—C11A—C12A | 105.4 (6) | H22D—C22A—H22F | 109.5 |
C1A—C11A—C19A | 111.5 (6) | H22E—C22A—H22F | 109.5 |
C3—O2—C1—C11 | −48.6 (10) | C9—C10—C11—C12 | −31.4 (9) |
C3A—O2A—C1A—C11A | −43.2 (9) | C4—C10—C11—C12 | −160.1 (6) |
C1—O2—C3—O3 | −177.0 (7) | O2A—C1A—C11A—C12A | −171.7 (6) |
C1—O2—C3—C4 | 2.0 (10) | O2A—C1A—C11A—C19A | −52.9 (8) |
C1A—O2A—C3A—O3A | 178.3 (7) | O2A—C1A—C11A—C10A | 66.1 (8) |
C1A—O2A—C3A—C4A | −4.4 (10) | C9A—C10A—C11A—C1A | 87.5 (7) |
O3—C3—C4—C5 | −33.7 (10) | C4A—C10A—C11A—C1A | −42.6 (7) |
O2—C3—C4—C5 | 147.3 (7) | C9A—C10A—C11A—C12A | −28.5 (8) |
O3—C3—C4—C20 | 71.5 (10) | C4A—C10A—C11A—C12A | −158.6 (6) |
O2—C3—C4—C20 | −107.5 (8) | C9A—C10A—C11A—C19A | −152.1 (6) |
O3—C3—C4—C10 | −160.1 (7) | C4A—C10A—C11A—C19A | 77.8 (7) |
O2—C3—C4—C10 | 21.0 (10) | C1—C11—C12—C13 | 173.9 (7) |
O3A—C3A—C4A—C20A | 75.2 (9) | C19—C11—C12—C13 | 52.5 (9) |
O2A—C3A—C4A—C20A | −102.0 (8) | C10—C11—C12—C13 | −69.7 (9) |
O3A—C3A—C4A—C5A | −31.7 (10) | C1A—C11A—C12A—C13A | 169.9 (6) |
O2A—C3A—C4A—C5A | 151.2 (7) | C19A—C11A—C12A—C13A | 49.8 (8) |
O3A—C3A—C4A—C10A | −157.8 (7) | C10A—C11A—C12A—C13A | −73.7 (8) |
O2A—C3A—C4A—C10A | 25.1 (10) | C11—C12—C13—C14 | −59.8 (10) |
C3—C4—C5—O4 | −71.1 (9) | C11A—C12A—C13A—C14A | −59.2 (9) |
C20—C4—C5—O4 | 174.0 (7) | C12—C13—C14—C15 | 59.2 (10) |
C10—C4—C5—O4 | 59.9 (9) | C12A—C13A—C14A—C15A | 60.9 (9) |
C3—C4—C5—C6 | 165.9 (6) | C13—C14—C15—C16 | −159.2 (8) |
C20—C4—C5—C6 | 51.0 (7) | C13—C14—C15—C22 | 78.7 (9) |
C10—C4—C5—C6 | −63.1 (7) | C13—C14—C15—C19 | −52.0 (9) |
C3A—C4A—C5A—O4A | −78.8 (9) | C13A—C14A—C15A—C16A | −163.1 (7) |
C20A—C4A—C5A—O4A | 167.0 (6) | C13A—C14A—C15A—C22A | 77.4 (8) |
C10A—C4A—C5A—O4A | 52.0 (8) | C13A—C14A—C15A—C19A | −54.4 (9) |
C3A—C4A—C5A—C6A | 159.4 (6) | C18—O1—C16—C15 | 25.3 (9) |
C20A—C4A—C5A—C6A | 45.1 (8) | C14—C15—C16—O1 | 75.6 (8) |
C10A—C4A—C5A—C6A | −69.9 (7) | C22—C15—C16—O1 | −162.7 (6) |
O4—C5—C6—C21 | 19.4 (12) | C19—C15—C16—O1 | −39.0 (8) |
C4—C5—C6—C21 | 143.5 (9) | C18A—O1A—C16A—C15A | 23.0 (9) |
O4—C5—C6—C7 | −153.2 (6) | C14A—C15A—C16A—O1A | 81.6 (8) |
C4—C5—C6—C7 | −29.1 (7) | C22A—C15A—C16A—O1A | −158.5 (6) |
O4A—C5A—C6A—C21A | 27.6 (12) | C19A—C15A—C16A—O1A | −34.2 (7) |
C4A—C5A—C6A—C21A | 153.0 (9) | C16—O1—C18—O6 | −178.1 (9) |
O4A—C5A—C6A—C7A | −146.7 (7) | C16—O1—C18—C19 | 1.0 (10) |
C4A—C5A—C6A—C7A | −21.2 (9) | C16A—O1A—C18A—O6A | 177.5 (8) |
C21—C6—C7—C8 | −62.3 (11) | C16A—O1A—C18A—C19A | −0.6 (9) |
C5—C6—C7—C8 | 110.3 (7) | O6—C18—C19—C11 | 25.6 (14) |
C21—C6—C7—C20 | −177.4 (8) | O1—C18—C19—C11 | −153.3 (7) |
C5—C6—C7—C20 | −4.9 (8) | O6—C18—C19—C15 | 153.3 (11) |
C21A—C6A—C7A—C8A | −69.4 (11) | O1—C18—C19—C15 | −25.6 (9) |
C5A—C6A—C7A—C8A | 104.7 (7) | C1—C11—C19—C18 | −47.2 (9) |
C21A—C6A—C7A—C20A | 174.3 (9) | C12—C11—C19—C18 | 71.6 (8) |
C5A—C6A—C7A—C20A | −11.5 (9) | C10—C11—C19—C18 | −164.3 (6) |
C6—C7—C8—C9 | −81.4 (8) | C1—C11—C19—C15 | −165.8 (6) |
C20—C7—C8—C9 | 30.3 (9) | C12—C11—C19—C15 | −46.9 (9) |
C6A—C7A—C8A—C9A | −83.1 (8) | C10—C11—C19—C15 | 77.2 (8) |
C20A—C7A—C8A—C9A | 29.0 (9) | C16—C15—C19—C18 | 37.5 (8) |
C7—C8—C9—O5 | −87.8 (7) | C14—C15—C19—C18 | −78.5 (8) |
C7—C8—C9—C10 | 34.6 (9) | C22—C15—C19—C18 | 155.4 (7) |
C7A—C8A—C9A—O5A | −88.3 (7) | C16—C15—C19—C11 | 163.3 (7) |
C7A—C8A—C9A—C10A | 33.5 (9) | C14—C15—C19—C11 | 47.3 (9) |
O5—C9—C10—C11 | −56.6 (8) | C22—C15—C19—C11 | −78.8 (9) |
C8—C9—C10—C11 | −179.8 (6) | O6A—C18A—C19A—C15A | 160.9 (8) |
O5—C9—C10—C4 | 71.4 (8) | O1A—C18A—C19A—C15A | −21.2 (8) |
C8—C9—C10—C4 | −51.8 (8) | O6A—C18A—C19A—C11A | 32.0 (12) |
C3—C4—C10—C9 | −127.3 (7) | O1A—C18A—C19A—C11A | −150.1 (6) |
C5—C4—C10—C9 | 106.8 (7) | C16A—C15A—C19A—C18A | 32.2 (7) |
C20—C4—C10—C9 | 1.6 (8) | C14A—C15A—C19A—C18A | −82.8 (7) |
C3—C4—C10—C11 | 2.5 (9) | C22A—C15A—C19A—C18A | 150.0 (7) |
C5—C4—C10—C11 | −123.4 (6) | C16A—C15A—C19A—C11A | 161.7 (6) |
C20—C4—C10—C11 | 131.5 (6) | C14A—C15A—C19A—C11A | 46.7 (8) |
O5A—C9A—C10A—C11A | −53.7 (7) | C22A—C15A—C19A—C11A | −80.5 (8) |
C8A—C9A—C10A—C11A | −176.3 (6) | C1A—C11A—C19A—C18A | −38.9 (9) |
O5A—C9A—C10A—C4A | 75.5 (7) | C12A—C11A—C19A—C18A | 77.4 (8) |
C8A—C9A—C10A—C4A | −47.1 (8) | C10A—C11A—C19A—C18A | −156.0 (6) |
C3A—C4A—C10A—C9A | −129.7 (7) | C1A—C11A—C19A—C15A | −160.3 (6) |
C20A—C4A—C10A—C9A | −3.1 (8) | C12A—C11A—C19A—C15A | −44.0 (8) |
C5A—C4A—C10A—C9A | 103.9 (7) | C10A—C11A—C19A—C15A | 82.7 (7) |
C3A—C4A—C10A—C11A | 1.6 (9) | C6—C7—C20—C4 | 36.9 (7) |
C20A—C4A—C10A—C11A | 128.3 (6) | C8—C7—C20—C4 | −79.1 (7) |
C5A—C4A—C10A—C11A | −124.8 (6) | C3—C4—C20—C7 | −167.3 (6) |
O2—C1—C11—C19 | −52.1 (9) | C5—C4—C20—C7 | −54.0 (7) |
O2—C1—C11—C12 | −170.9 (7) | C10—C4—C20—C7 | 59.9 (7) |
O2—C1—C11—C10 | 67.8 (8) | C6A—C7A—C20A—C4A | 39.8 (8) |
C9—C10—C11—C1 | 86.4 (7) | C8A—C7A—C20A—C4A | −77.7 (7) |
C4—C10—C11—C1 | −42.3 (7) | C3A—C4A—C20A—C7A | −167.0 (6) |
C9—C10—C11—C19 | −152.5 (6) | C5A—C4A—C20A—C7A | −52.3 (7) |
C4—C10—C11—C19 | 78.8 (7) | C10A—C4A—C20A—C7A | 61.9 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3A | 0.82 | 2.46 | 3.159 (8) | 144 |
O4A—H4A···O3 | 0.82 | 1.94 | 2.750 (8) | 168 |
O5—H5···O3Ai | 0.82 | 1.97 | 2.787 (8) | 175 |
O5A—H5B···O6Aii | 0.82 | 2.11 | 2.903 (9) | 164 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H26O6 |
Mr | 362.41 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 12.2614 (15), 15.6668 (18), 18.697 (2) |
V (Å3) | 3591.7 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.41 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.961, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17440, 3556, 1970 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.237, 1.10 |
No. of reflections | 3556 |
No. of parameters | 472 |
No. of restraints | 1896 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.56 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3A | 0.82 | 2.46 | 3.159 (8) | 143.9 |
O4A—H4A···O3 | 0.82 | 1.94 | 2.750 (8) | 168.0 |
O5—H5···O3Ai | 0.82 | 1.97 | 2.787 (8) | 175.0 |
O5A—H5B···O6Aii | 0.82 | 2.11 | 2.903 (9) | 163.9 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z. |
Molecule | A | B | ||||
Puckering parameters | Q | θ | ϕ | Q | θ | ϕ |
Ring A, A" | 0.545 (9) | 171.2 (9) | 296 (6) | 0.546 (8) | 168.9 (8) | 315 (5) |
Ring B, B" | 0.584 (9) | 65.6 (8) | 91.8 (8) | 0.582 (8) | 68.4 (8) | 95.2 (7) |
Ring C, C" | 0.861 (8) | 80.2 (5) | 286.4 (6) | 0.837 (8) | 78.9 (5) | 288.8 (6) |
Puckering parameters | Q2 | ϕ2 | Q2 | ϕ2 | ||
Ring D, D" | 0.561 (9) | 174.6 (9) | 0.530 (9) | 167.1 (9) | ||
Ring E, E" | 0.412 (9) | 254.0 (13) | 0.355 (9) | 251.8 (14) |
Ring A: C11···C15-C19 Ring A": C11A···C15A-C19A Ring B: O2-C1-C11-C10-C4-C3 Ring B": O2A-C1A-C11A-C10A-C4A-C3A Ring C: C4-C10-C9-C8-C7-C20 Ring C": C4A-C10A-C9A-C8A-C7A-C20A Ring D: C4···C7-C20 Ring D": C4A···C7A-C20A Ring E: O1-C16-C15-C19-C18 Ring E": O1A-C16A-C15A-C19A-C18A |
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The diterpenoid Guidongnin A, C20H26O6, has been previously isolated from Rabdosia rubescens Hara (Sun et al., 1988), its structure was established from the spectral and chemical evidence. Recently we isolated the compound from Rabdosia var lophanthoides Hara for the first time, and its structure is confirmed by an X-ray diffraction study.
Two unique molecules are present in the asymmetric unit, both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from five fused rings, three six membered (A,B,C,A',B'and C') and two five membered rings (D,E,D' and E'). The conformations of the different rings extracted from the puckering parameters (Cremer & Pople, 1975) are given in Table 2. Ring A and A' adopt a chair conformation, ring B and B' exist in a screw-boat conformation and rings C and C' adopt a boat conformation. Rings D, D', E and E' adopt an envelope conformation. The isobenzofuran ring system couples orthogonally to the methanocyclohepta[c] pyran moiety through a spiro C atom.
This two molecules are linked by O4—H4···O3A and O4A—H4A···O3 hydrogen bonds to form a dimer. The dimers are further interconnected through O—H···O hydrogen bonds (Fig.3).