


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015010592/xu5852sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015010592/xu5852Isup2.hkl |
CCDC reference: 1404443
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.058
- wR factor = 0.198
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 2 Check
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.9 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) ... 4.8 Ratio PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C25 Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0059 Ang. PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11 Report PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) . 1 Check PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S . 21.67
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.14 Report PLAT791_ALERT_4_G The Model has Chirality at C5 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C9 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C10 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C13 (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C14 (Chiral SPGR) S Verify PLAT791_ALERT_4_G The Model has Chirality at C16 (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C17 (Chiral SPGR) R Verify PLAT791_ALERT_4_G The Model has Chirality at C20 (Chiral SPGR) S Verify PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 14 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
Melia azedarach Linn. (Meliaceae), a high tree, enjoys a broad distribution in the most parts of China. The triterpenoids which isolated from this plant is well known for its pharmacological properties, such as analgesic, anticancer, antiviral, antimalarial, antibacterial and antifeedant activities (Faizi et al., 2002; Wang et al., 2011; Dong et al., 2012). The title compound, 16-hydroxy-4,4,10,13,14-pentamethyl -17-(6-methylhept-5-en-2-yl)-4,5,6,9,10,11,12,13,14,15,16,17-dodecahydro -1H-cyclopenta [α]phenanthren-3(2H)-one (I) (Fig. 1) was isolated from the barks of Melia azedarach (Chiang & Chang, 1969). In this work, we obtained a single-crystal of (I) and present here its crystal structure.
The title compound contains a fused four-ring triterpenoid system. rings A adopt a chair conformation, while ring B with one double bond adopts a half-chair conformation, ring C adopts a twist boat conformation and ring D adopts an envelope conformation. Intermolecular O—H···O hydrogen bonds are present in the crystal structure (Table 1).
The air-dried and powered barks of Melia azedarach L.(10.6kg) were percolated with 95% aqueous ethanol for 7 days at room temperature for three times. After evaporation of the solvent under reduced pressure, the gummy residue was suspended in water and then partitioned with EtOAc. The EtOAc extract (145g) was subjected to CC on silica gel eluting with petroleum ether-EtOAc (from 20:1 to 2:1, v/v) to give fifteen fractions (1-15). Fraction 5 (22g) was further separated on silica gel CC and eluted with petroleum-acetone from 20:1 to 3:1, yielding five sub-fractions (2a-2e). Sub-fraction 2c (3.25g), subjected to a series of purification steps using silica gel CC, Sephadex LH-20 to afford Sub-fraction 2c-b-b-b (120.4mg) , then use semi-preparative HPLC (MeCN/H2O 90:10, flow rate 3.8 mL/min) to afford (I) (16.8mg, t R = 32.5min). The structures of (I) was elucidated by means of NMR. Colourless crystal were obtained in the freezer after one month by slow evaporation from acetone/methanol [10:1 (v/v)] mixture solution.
H-atoms bound to carbon were placed in calculated positions with C—H = 0.93–0.98 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others. Hydroxy H atoms was placed in calculated position with O—-H = 0.82 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(O). The absolute structure has not been determined as no significant anomalous scattering, equivalent diffractions were merged.
Data collection: APEX2 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of (I) with the atom numbering, showing displacement ellipsoids at the 50% probability level. |
C30H48O2 | F(000) = 976 |
Mr = 440.68 | Dx = 1.073 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2467 reflections |
a = 12.436 (7) Å | θ = 2.5–21.6° |
b = 13.571 (7) Å | µ = 0.07 mm−1 |
c = 16.159 (9) Å | T = 298 K |
V = 2727 (3) Å3 | Block, colorless |
Z = 4 | 0.31 × 0.25 × 0.22 mm |
Bruker APEXII area-detector diffractometer | 3000 independent reflections |
Radiation source: fine-focus sealed tube | 2320 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→13 |
Tmin = 0.980, Tmax = 0.986 | k = −16→16 |
12873 measured reflections | l = −18→19 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1351P)2 + 0.062P] where P = (Fo2 + 2Fc2)/3 |
3000 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C30H48O2 | V = 2727 (3) Å3 |
Mr = 440.68 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.436 (7) Å | µ = 0.07 mm−1 |
b = 13.571 (7) Å | T = 298 K |
c = 16.159 (9) Å | 0.31 × 0.25 × 0.22 mm |
Bruker APEXII area-detector diffractometer | 3000 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2320 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.986 | Rint = 0.044 |
12873 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.38 e Å−3 |
3000 reflections | Δρmin = −0.30 e Å−3 |
298 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 | −0.2176 (3) | 1.0719 (2) | 0.49312 (19) | 0.0701 (10) | |
O2 | 0.2062 (3) | 0.7741 (2) | −0.04929 (17) | 0.0596 (8) | |
H2 | 0.2257 | 0.7200 | −0.0324 | 0.089* | |
C1 | −0.2070 (3) | 1.0561 (3) | 0.2829 (2) | 0.0491 (10) | |
H1A | −0.1553 | 1.1080 | 0.2938 | 0.059* | |
H1B | −0.2475 | 1.0746 | 0.2341 | 0.059* | |
C2 | −0.2841 (4) | 1.0484 (3) | 0.3565 (3) | 0.0603 (12) | |
H2A | −0.3195 | 1.1112 | 0.3656 | 0.072* | |
H2B | −0.3389 | 0.9993 | 0.3452 | 0.072* | |
C3 | −0.2204 (3) | 1.0194 (3) | 0.4330 (3) | 0.0496 (10) | |
C4 | −0.1582 (3) | 0.9224 (3) | 0.4286 (3) | 0.0507 (10) | |
C5 | −0.0913 (3) | 0.9245 (3) | 0.3454 (2) | 0.0403 (8) | |
H5 | −0.0350 | 0.9736 | 0.3554 | 0.048* | |
C6 | −0.0298 (4) | 0.8278 (3) | 0.3325 (3) | 0.0593 (12) | |
H6A | 0.0226 | 0.8201 | 0.3766 | 0.071* | |
H6B | −0.0798 | 0.7731 | 0.3361 | 0.071* | |
C7 | 0.0274 (3) | 0.8238 (3) | 0.2502 (3) | 0.0498 (10) | |
H7 | 0.0736 | 0.7710 | 0.2410 | 0.060* | |
C8 | 0.0173 (3) | 0.8893 (2) | 0.1897 (2) | 0.0353 (7) | |
C9 | −0.0524 (3) | 0.9818 (2) | 0.2036 (2) | 0.0332 (7) | |
H9 | −0.0059 | 1.0295 | 0.2318 | 0.040* | |
C10 | −0.1457 (3) | 0.9588 (2) | 0.2652 (2) | 0.0383 (8) | |
C11 | −0.0870 (3) | 1.0312 (3) | 0.1222 (2) | 0.0445 (9) | |
H11A | −0.1148 | 1.0961 | 0.1352 | 0.053* | |
H11B | −0.1458 | 0.9932 | 0.0990 | 0.053* | |
C12 | 0.0017 (3) | 1.0428 (3) | 0.0540 (2) | 0.0440 (9) | |
H12A | −0.0299 | 1.0277 | 0.0006 | 0.053* | |
H12B | 0.0249 | 1.1110 | 0.0527 | 0.053* | |
C13 | 0.1008 (3) | 0.9767 (2) | 0.0667 (2) | 0.0343 (7) | |
C14 | 0.0645 (3) | 0.8748 (2) | 0.1044 (2) | 0.0346 (7) | |
C15 | 0.1679 (3) | 0.8139 (3) | 0.0979 (2) | 0.0435 (9) | |
H15A | 0.1517 | 0.7440 | 0.0976 | 0.052* | |
H15B | 0.2157 | 0.8280 | 0.1438 | 0.052* | |
C16 | 0.2196 (3) | 0.8456 (3) | 0.0147 (2) | 0.0436 (9) | |
H16 | 0.2964 | 0.8585 | 0.0231 | 0.052* | |
C17 | 0.1624 (3) | 0.9421 (2) | −0.0125 (2) | 0.0362 (7) | |
H17 | 0.1076 | 0.9229 | −0.0530 | 0.043* | |
C18 | 0.1798 (3) | 1.0301 (3) | 0.1263 (2) | 0.0454 (9) | |
H18A | 0.2058 | 1.0892 | 0.1005 | 0.068* | |
H18B | 0.2393 | 0.9874 | 0.1384 | 0.068* | |
H18C | 0.1431 | 1.0465 | 0.1767 | 0.068* | |
C19 | −0.2237 (4) | 0.8835 (3) | 0.2255 (3) | 0.0625 (12) | |
H19A | −0.1870 | 0.8221 | 0.2171 | 0.094* | |
H19B | −0.2485 | 0.9084 | 0.1732 | 0.094* | |
H19C | −0.2841 | 0.8733 | 0.2615 | 0.094* | |
C20 | 0.2391 (3) | 1.0155 (3) | −0.0574 (2) | 0.0470 (9) | |
H20 | 0.2945 | 1.0353 | −0.0176 | 0.056* | |
C21 | 0.2962 (4) | 0.9630 (4) | −0.1298 (3) | 0.0590 (11) | |
H21A | 0.2434 | 0.9361 | −0.1668 | 0.089* | |
H21B | 0.3403 | 0.9107 | −0.1086 | 0.089* | |
H21C | 0.3404 | 1.0094 | −0.1590 | 0.089* | |
C22 | 0.1849 (4) | 1.1094 (3) | −0.0890 (3) | 0.0569 (11) | |
H22A | 0.1508 | 1.1419 | −0.0424 | 0.068* | |
H22B | 0.2403 | 1.1532 | −0.1096 | 0.068* | |
C23 | 0.1024 (5) | 1.0964 (3) | −0.1554 (3) | 0.0704 (14) | |
H23A | 0.0522 | 1.0455 | −0.1385 | 0.085* | |
H23B | 0.1380 | 1.0739 | −0.2054 | 0.085* | |
C24 | 0.0405 (6) | 1.1890 (4) | −0.1748 (4) | 0.0844 (17) | |
H24 | 0.0212 | 1.2267 | −0.1290 | 0.101* | |
C25 | 0.0095 (4) | 1.2247 (4) | −0.2468 (4) | 0.0774 (15) | |
C26 | 0.0271 (5) | 1.1679 (7) | −0.3249 (4) | 0.111 (3) | |
H26A | 0.0672 | 1.1092 | −0.3129 | 0.166* | |
H26B | 0.0666 | 1.2077 | −0.3635 | 0.166* | |
H26C | −0.0411 | 1.1504 | −0.3485 | 0.166* | |
C27 | −0.0482 (6) | 1.3212 (5) | −0.2542 (6) | 0.129 (3) | |
H27A | −0.0586 | 1.3488 | −0.2001 | 0.193* | |
H27B | −0.1168 | 1.3109 | −0.2801 | 0.193* | |
H27C | −0.0061 | 1.3657 | −0.2872 | 0.193* | |
C28 | −0.2423 (5) | 0.8383 (3) | 0.4348 (3) | 0.0740 (15) | |
H28A | −0.2846 | 0.8469 | 0.4840 | 0.111* | |
H28B | −0.2060 | 0.7760 | 0.4371 | 0.111* | |
H28C | −0.2885 | 0.8400 | 0.3872 | 0.111* | |
C29 | −0.0838 (5) | 0.9145 (5) | 0.5010 (3) | 0.0841 (17) | |
H29A | −0.0379 | 0.9713 | 0.5028 | 0.126* | |
H29B | −0.0406 | 0.8562 | 0.4955 | 0.126* | |
H29C | −0.1250 | 0.9108 | 0.5511 | 0.126* | |
C30 | −0.0204 (3) | 0.8237 (3) | 0.0497 (3) | 0.0493 (9) | |
H30A | −0.0429 | 0.7635 | 0.0756 | 0.074* | |
H30B | 0.0102 | 0.8094 | −0.0035 | 0.074* | |
H30C | −0.0813 | 0.8664 | 0.0430 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.106 (3) | 0.0522 (16) | 0.0525 (18) | 0.0022 (17) | 0.0278 (19) | −0.0093 (15) |
O2 | 0.088 (2) | 0.0471 (14) | 0.0433 (15) | 0.0172 (15) | 0.0117 (15) | −0.0010 (12) |
C1 | 0.049 (2) | 0.051 (2) | 0.048 (2) | 0.0132 (18) | 0.0126 (18) | 0.0032 (18) |
C2 | 0.056 (2) | 0.057 (2) | 0.069 (3) | 0.016 (2) | 0.023 (2) | 0.003 (2) |
C3 | 0.057 (2) | 0.0394 (18) | 0.052 (2) | −0.0032 (17) | 0.0254 (19) | −0.0021 (18) |
C4 | 0.064 (2) | 0.0424 (19) | 0.046 (2) | 0.0032 (18) | 0.018 (2) | 0.0011 (17) |
C5 | 0.0451 (19) | 0.0362 (17) | 0.0396 (19) | −0.0001 (16) | 0.0070 (16) | −0.0007 (15) |
C6 | 0.079 (3) | 0.052 (2) | 0.048 (2) | 0.025 (2) | 0.023 (2) | 0.0116 (19) |
C7 | 0.062 (2) | 0.0406 (18) | 0.046 (2) | 0.0200 (18) | 0.016 (2) | 0.0088 (17) |
C8 | 0.0376 (17) | 0.0309 (15) | 0.0373 (18) | 0.0029 (13) | 0.0015 (15) | −0.0008 (14) |
C9 | 0.0349 (16) | 0.0326 (15) | 0.0322 (17) | 0.0033 (13) | 0.0004 (14) | −0.0018 (14) |
C10 | 0.0373 (17) | 0.0372 (17) | 0.0403 (19) | 0.0001 (14) | 0.0029 (15) | −0.0025 (15) |
C11 | 0.049 (2) | 0.048 (2) | 0.0363 (19) | 0.0168 (17) | −0.0024 (16) | 0.0032 (16) |
C12 | 0.051 (2) | 0.0444 (18) | 0.0362 (18) | 0.0123 (16) | −0.0010 (17) | 0.0016 (16) |
C13 | 0.0387 (16) | 0.0327 (15) | 0.0316 (17) | −0.0019 (13) | −0.0055 (14) | 0.0021 (14) |
C14 | 0.0376 (17) | 0.0313 (15) | 0.0348 (18) | 0.0023 (13) | 0.0033 (15) | 0.0006 (14) |
C15 | 0.054 (2) | 0.0378 (17) | 0.039 (2) | 0.0103 (16) | 0.0049 (17) | 0.0046 (15) |
C16 | 0.046 (2) | 0.0493 (19) | 0.0354 (19) | 0.0110 (16) | 0.0054 (16) | 0.0016 (16) |
C17 | 0.0380 (17) | 0.0413 (17) | 0.0292 (16) | 0.0009 (14) | −0.0023 (14) | 0.0015 (14) |
C18 | 0.046 (2) | 0.050 (2) | 0.040 (2) | −0.0088 (17) | −0.0043 (16) | −0.0036 (17) |
C19 | 0.051 (2) | 0.067 (3) | 0.069 (3) | −0.020 (2) | 0.009 (2) | −0.015 (2) |
C20 | 0.052 (2) | 0.0485 (19) | 0.040 (2) | −0.0078 (17) | 0.0036 (17) | 0.0050 (17) |
C21 | 0.054 (2) | 0.073 (3) | 0.050 (2) | 0.004 (2) | 0.017 (2) | 0.014 (2) |
C22 | 0.074 (3) | 0.045 (2) | 0.052 (2) | −0.0038 (19) | 0.010 (2) | 0.0076 (19) |
C23 | 0.103 (4) | 0.056 (2) | 0.053 (3) | 0.004 (3) | −0.001 (3) | 0.005 (2) |
C24 | 0.114 (4) | 0.069 (3) | 0.071 (3) | 0.019 (3) | −0.017 (3) | 0.000 (3) |
C25 | 0.063 (3) | 0.082 (3) | 0.087 (4) | 0.008 (3) | −0.011 (3) | 0.034 (3) |
C26 | 0.085 (4) | 0.187 (8) | 0.060 (3) | 0.028 (5) | 0.001 (3) | 0.027 (4) |
C27 | 0.099 (5) | 0.088 (4) | 0.199 (8) | 0.003 (4) | −0.048 (6) | 0.060 (5) |
C28 | 0.103 (4) | 0.045 (2) | 0.074 (3) | −0.007 (2) | 0.044 (3) | 0.007 (2) |
C29 | 0.101 (4) | 0.115 (4) | 0.036 (2) | 0.026 (4) | 0.017 (3) | 0.006 (3) |
C30 | 0.052 (2) | 0.0454 (19) | 0.050 (2) | −0.0099 (17) | 0.0067 (19) | −0.0096 (18) |
O1—C3 | 1.206 (5) | C16—C17 | 1.553 (5) |
O2—C16 | 1.428 (4) | C16—H16 | 0.9800 |
O2—H2 | 0.8200 | C17—C20 | 1.558 (5) |
C1—C2 | 1.531 (5) | C17—H17 | 0.9800 |
C1—C10 | 1.552 (5) | C18—H18A | 0.9600 |
C1—H1A | 0.9700 | C18—H18B | 0.9600 |
C1—H1B | 0.9700 | C18—H18C | 0.9600 |
C2—C3 | 1.521 (6) | C19—H19A | 0.9600 |
C2—H2A | 0.9700 | C19—H19B | 0.9600 |
C2—H2B | 0.9700 | C19—H19C | 0.9600 |
C3—C4 | 1.528 (5) | C20—C22 | 1.529 (6) |
C4—C29 | 1.495 (7) | C20—C21 | 1.543 (6) |
C4—C28 | 1.552 (6) | C20—H20 | 0.9800 |
C4—C5 | 1.581 (5) | C21—H21A | 0.9600 |
C5—C6 | 1.533 (5) | C21—H21B | 0.9600 |
C5—C10 | 1.535 (5) | C21—H21C | 0.9600 |
C5—H5 | 0.9800 | C22—C23 | 1.495 (7) |
C6—C7 | 1.510 (6) | C22—H22A | 0.9700 |
C6—H6A | 0.9700 | C22—H22B | 0.9700 |
C6—H6B | 0.9700 | C23—C24 | 1.507 (7) |
C7—C8 | 1.327 (5) | C23—H23A | 0.9700 |
C7—H7 | 0.9300 | C23—H23B | 0.9700 |
C8—C14 | 1.510 (5) | C24—C25 | 1.318 (8) |
C8—C9 | 1.541 (4) | C24—H24 | 0.9300 |
C9—C11 | 1.537 (5) | C25—C26 | 1.495 (10) |
C9—C10 | 1.560 (5) | C25—C27 | 1.498 (8) |
C9—H9 | 0.9800 | C26—H26A | 0.9600 |
C10—C19 | 1.549 (5) | C26—H26B | 0.9600 |
C11—C12 | 1.568 (5) | C26—H26C | 0.9600 |
C11—H11A | 0.9700 | C27—H27A | 0.9600 |
C11—H11B | 0.9700 | C27—H27B | 0.9600 |
C12—C13 | 1.537 (5) | C27—H27C | 0.9600 |
C12—H12A | 0.9700 | C28—H28A | 0.9600 |
C12—H12B | 0.9700 | C28—H28B | 0.9600 |
C13—C18 | 1.554 (5) | C28—H28C | 0.9600 |
C13—C17 | 1.564 (5) | C29—H29A | 0.9600 |
C13—C14 | 1.577 (5) | C29—H29B | 0.9600 |
C14—C15 | 1.532 (5) | C29—H29C | 0.9600 |
C14—C30 | 1.542 (5) | C30—H30A | 0.9600 |
C15—C16 | 1.550 (5) | C30—H30B | 0.9600 |
C15—H15A | 0.9700 | C30—H30C | 0.9600 |
C15—H15B | 0.9700 | ||
C16—O2—H2 | 109.5 | O2—C16—C17 | 108.3 (3) |
C2—C1—C10 | 113.1 (3) | C15—C16—C17 | 106.8 (3) |
C2—C1—H1A | 108.9 | O2—C16—H16 | 109.5 |
C10—C1—H1A | 109.0 | C15—C16—H16 | 109.5 |
C2—C1—H1B | 109.0 | C17—C16—H16 | 109.5 |
C10—C1—H1B | 108.9 | C16—C17—C20 | 113.0 (3) |
H1A—C1—H1B | 107.8 | C16—C17—C13 | 104.2 (3) |
C3—C2—C1 | 108.8 (3) | C20—C17—C13 | 119.2 (3) |
C3—C2—H2A | 109.9 | C16—C17—H17 | 106.5 |
C1—C2—H2A | 109.9 | C20—C17—H17 | 106.5 |
C3—C2—H2B | 109.9 | C13—C17—H17 | 106.5 |
C1—C2—H2B | 109.9 | C13—C18—H18A | 109.5 |
H2A—C2—H2B | 108.3 | C13—C18—H18B | 109.5 |
O1—C3—C2 | 121.1 (4) | H18A—C18—H18B | 109.5 |
O1—C3—C4 | 122.2 (4) | C13—C18—H18C | 109.5 |
C2—C3—C4 | 116.7 (3) | H18A—C18—H18C | 109.5 |
C29—C4—C3 | 109.8 (4) | H18B—C18—H18C | 109.5 |
C29—C4—C28 | 108.3 (4) | C10—C19—H19A | 109.5 |
C3—C4—C28 | 106.9 (3) | C10—C19—H19B | 109.5 |
C29—C4—C5 | 109.9 (3) | H19A—C19—H19B | 109.5 |
C3—C4—C5 | 106.9 (3) | C10—C19—H19C | 109.5 |
C28—C4—C5 | 115.0 (3) | H19A—C19—H19C | 109.5 |
C6—C5—C10 | 111.4 (3) | H19B—C19—H19C | 109.5 |
C6—C5—C4 | 111.3 (3) | C22—C20—C21 | 109.5 (3) |
C10—C5—C4 | 119.4 (3) | C22—C20—C17 | 114.7 (3) |
C6—C5—H5 | 104.3 | C21—C20—C17 | 109.8 (3) |
C10—C5—H5 | 104.3 | C22—C20—H20 | 107.5 |
C4—C5—H5 | 104.3 | C21—C20—H20 | 107.5 |
C7—C6—C5 | 112.7 (3) | C17—C20—H20 | 107.5 |
C7—C6—H6A | 109.1 | C20—C21—H21A | 109.5 |
C5—C6—H6A | 109.1 | C20—C21—H21B | 109.5 |
C7—C6—H6B | 109.1 | H21A—C21—H21B | 109.5 |
C5—C6—H6B | 109.1 | C20—C21—H21C | 109.5 |
H6A—C6—H6B | 107.8 | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 125.5 (3) | H21B—C21—H21C | 109.5 |
C8—C7—H7 | 117.2 | C23—C22—C20 | 116.4 (4) |
C6—C7—H7 | 117.2 | C23—C22—H22A | 108.2 |
C7—C8—C14 | 123.2 (3) | C20—C22—H22A | 108.2 |
C7—C8—C9 | 119.4 (3) | C23—C22—H22B | 108.2 |
C14—C8—C9 | 117.2 (3) | C20—C22—H22B | 108.2 |
C11—C9—C8 | 112.8 (3) | H22A—C22—H22B | 107.3 |
C11—C9—C10 | 115.1 (3) | C22—C23—C24 | 113.7 (4) |
C8—C9—C10 | 110.4 (3) | C22—C23—H23A | 108.8 |
C11—C9—H9 | 105.9 | C24—C23—H23A | 108.8 |
C8—C9—H9 | 105.9 | C22—C23—H23B | 108.8 |
C10—C9—H9 | 105.9 | C24—C23—H23B | 108.8 |
C5—C10—C19 | 115.2 (3) | H23A—C23—H23B | 107.7 |
C5—C10—C1 | 108.6 (3) | C25—C24—C23 | 129.7 (6) |
C19—C10—C1 | 109.3 (3) | C25—C24—H24 | 115.1 |
C5—C10—C9 | 105.8 (3) | C23—C24—H24 | 115.1 |
C19—C10—C9 | 109.5 (3) | C24—C25—C26 | 120.9 (5) |
C1—C10—C9 | 108.3 (3) | C24—C25—C27 | 122.1 (6) |
C9—C11—C12 | 116.6 (3) | C26—C25—C27 | 116.9 (6) |
C9—C11—H11A | 108.1 | C25—C26—H26A | 109.5 |
C12—C11—H11A | 108.1 | C25—C26—H26B | 109.5 |
C9—C11—H11B | 108.1 | H26A—C26—H26B | 109.5 |
C12—C11—H11B | 108.1 | C25—C26—H26C | 109.5 |
H11A—C11—H11B | 107.3 | H26A—C26—H26C | 109.5 |
C13—C12—C11 | 114.3 (3) | H26B—C26—H26C | 109.5 |
C13—C12—H12A | 108.7 | C25—C27—H27A | 109.5 |
C11—C12—H12A | 108.7 | C25—C27—H27B | 109.5 |
C13—C12—H12B | 108.7 | H27A—C27—H27B | 109.5 |
C11—C12—H12B | 108.7 | C25—C27—H27C | 109.5 |
H12A—C12—H12B | 107.6 | H27A—C27—H27C | 109.5 |
C12—C13—C18 | 108.6 (3) | H27B—C27—H27C | 109.5 |
C12—C13—C17 | 117.3 (3) | C4—C28—H28A | 109.5 |
C18—C13—C17 | 109.7 (3) | C4—C28—H28B | 109.5 |
C12—C13—C14 | 109.5 (3) | H28A—C28—H28B | 109.5 |
C18—C13—C14 | 110.4 (3) | C4—C28—H28C | 109.5 |
C17—C13—C14 | 101.1 (2) | H28A—C28—H28C | 109.5 |
C8—C14—C15 | 117.4 (3) | H28B—C28—H28C | 109.5 |
C8—C14—C30 | 108.4 (3) | C4—C29—H29A | 109.5 |
C15—C14—C30 | 107.0 (3) | C4—C29—H29B | 109.5 |
C8—C14—C13 | 110.5 (3) | H29A—C29—H29B | 109.5 |
C15—C14—C13 | 101.9 (3) | C4—C29—H29C | 109.5 |
C30—C14—C13 | 111.6 (3) | H29A—C29—H29C | 109.5 |
C14—C15—C16 | 105.0 (3) | H29B—C29—H29C | 109.5 |
C14—C15—H15A | 110.8 | C14—C30—H30A | 109.5 |
C16—C15—H15A | 110.8 | C14—C30—H30B | 109.5 |
C14—C15—H15B | 110.8 | H30A—C30—H30B | 109.5 |
C16—C15—H15B | 110.8 | C14—C30—H30C | 109.5 |
H15A—C15—H15B | 108.8 | H30A—C30—H30C | 109.5 |
O2—C16—C15 | 113.0 (3) | H30B—C30—H30C | 109.5 |
C10—C1—C2—C3 | 58.6 (5) | C11—C12—C13—C17 | 150.0 (3) |
C1—C2—C3—O1 | 119.7 (4) | C11—C12—C13—C14 | 35.6 (4) |
C1—C2—C3—C4 | −58.8 (5) | C7—C8—C14—C15 | −30.3 (5) |
O1—C3—C4—C29 | −9.4 (5) | C9—C8—C14—C15 | 154.2 (3) |
C2—C3—C4—C29 | 169.0 (4) | C7—C8—C14—C30 | 90.9 (4) |
O1—C3—C4—C28 | 107.8 (5) | C9—C8—C14—C30 | −84.6 (4) |
C2—C3—C4—C28 | −73.8 (4) | C7—C8—C14—C13 | −146.5 (4) |
O1—C3—C4—C5 | −128.6 (4) | C9—C8—C14—C13 | 38.0 (4) |
C2—C3—C4—C5 | 49.8 (4) | C12—C13—C14—C8 | −64.4 (3) |
C29—C4—C5—C6 | 63.7 (5) | C18—C13—C14—C8 | 55.1 (4) |
C3—C4—C5—C6 | −177.2 (4) | C17—C13—C14—C8 | 171.2 (3) |
C28—C4—C5—C6 | −58.7 (5) | C12—C13—C14—C15 | 170.2 (3) |
C29—C4—C5—C10 | −164.2 (4) | C18—C13—C14—C15 | −70.3 (3) |
C3—C4—C5—C10 | −45.1 (4) | C17—C13—C14—C15 | 45.7 (3) |
C28—C4—C5—C10 | 73.3 (4) | C12—C13—C14—C30 | 56.3 (4) |
C10—C5—C6—C7 | 39.1 (5) | C18—C13—C14—C30 | 175.8 (3) |
C4—C5—C6—C7 | 175.1 (4) | C17—C13—C14—C30 | −68.1 (3) |
C5—C6—C7—C8 | −7.9 (7) | C8—C14—C15—C16 | −158.2 (3) |
C6—C7—C8—C14 | −171.4 (4) | C30—C14—C15—C16 | 79.8 (3) |
C6—C7—C8—C9 | 3.9 (7) | C13—C14—C15—C16 | −37.4 (3) |
C7—C8—C9—C11 | −160.7 (4) | C14—C15—C16—O2 | −104.2 (3) |
C14—C8—C9—C11 | 15.0 (4) | C14—C15—C16—C17 | 14.8 (4) |
C7—C8—C9—C10 | −30.4 (5) | O2—C16—C17—C20 | −93.0 (4) |
C14—C8—C9—C10 | 145.3 (3) | C15—C16—C17—C20 | 145.0 (3) |
C6—C5—C10—C19 | 56.6 (4) | O2—C16—C17—C13 | 136.1 (3) |
C4—C5—C10—C19 | −75.4 (4) | C15—C16—C17—C13 | 14.1 (4) |
C6—C5—C10—C1 | 179.5 (3) | C12—C13—C17—C16 | −155.4 (3) |
C4—C5—C10—C1 | 47.5 (4) | C18—C13—C17—C16 | 80.2 (3) |
C6—C5—C10—C9 | −64.5 (4) | C14—C13—C17—C16 | −36.4 (3) |
C4—C5—C10—C9 | 163.5 (3) | C12—C13—C17—C20 | 77.4 (4) |
C2—C1—C10—C5 | −52.9 (4) | C18—C13—C17—C20 | −47.0 (4) |
C2—C1—C10—C19 | 73.6 (5) | C14—C13—C17—C20 | −163.6 (3) |
C2—C1—C10—C9 | −167.3 (3) | C16—C17—C20—C22 | 177.2 (3) |
C11—C9—C10—C5 | −172.0 (3) | C13—C17—C20—C22 | −59.9 (4) |
C8—C9—C10—C5 | 58.8 (3) | C16—C17—C20—C21 | 53.3 (4) |
C11—C9—C10—C19 | 63.3 (4) | C13—C17—C20—C21 | 176.3 (3) |
C8—C9—C10—C19 | −65.8 (4) | C21—C20—C22—C23 | 59.2 (5) |
C11—C9—C10—C1 | −55.8 (4) | C17—C20—C22—C23 | −64.8 (5) |
C8—C9—C10—C1 | 175.1 (3) | C20—C22—C23—C24 | 171.4 (4) |
C8—C9—C11—C12 | −44.3 (4) | C22—C23—C24—C25 | 139.4 (7) |
C10—C9—C11—C12 | −172.2 (3) | C23—C24—C25—C26 | 5.0 (11) |
C9—C11—C12—C13 | 17.4 (5) | C23—C24—C25—C27 | −177.4 (6) |
C11—C12—C13—C18 | −85.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.11 | 2.894 (4) | 160 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.11 | 2.894 (4) | 160 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |