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In the title compound, C
26H
38O
10, the acafarnane skeleton consists of three
cis-fused rings, of which the five-membered ring is in an envelope conformation and the two six-membered rings adopt twist-boat and chair conformations. The lactone ring is in an envelope conformation. The
D-glucose, in the β position with respect to the acafarnane skeleton, adopts a chair conformation. The molecular structure and the crystal packing are stabilized by O—H
O interactions including a bifurcated hydrogen bond.
Supporting information
CCDC reference: 620674
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.085
- Data-to-parameter ratio = 6.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.71 Ratio
| Author Response: Due to poor quality of the crystal, data collected was not
sufficient. Therefore the hydrogen positions could not be found precisely.
|
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.75
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.56 Ratio
PLAT245_ALERT_2_C U(iso) H22 Smaller than U(eq) C22 by ... 0.01 AngSq
PLAT410_ALERT_2_C Short Intra H...H Contact H5 .. H14A .. 1.96 Ang.
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 70.08
From the CIF: _reflns_number_total 2483
Count of symmetry unique reflns 2486
Completeness (_total/calc) 99.88%
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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . S
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
18 ALERT level G = General alerts; check
17 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
2 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
Data collection: AED Software (Belletti et al., 1993); cell refinement: AED Software; data reduction: AED Software; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(1
S,3aR,5aR,6
S,6aR,7
S,9
R,11aS,11bR,11cS)-7-
(beta-
D-glucopyranosyloxy)dodecahydro-1,6-
dihydroxy-3a,11
b-dimethyl-8-methylene-1
H-
6a,9-Methanocyclohept[2,3]indeno[4,5-
c] furan-3(3aH)-one
top
Crystal data top
C26H38O10 | F(000) = 548 |
Mr = 510.56 | Dx = 1.384 Mg m−3 |
Monoclinic, P21 | Melting point: 110-112/% K |
Hall symbol: P 2yb | Cu Kα radiation, λ = 1.54178 Å |
a = 11.691 (2) Å | Cell parameters from 44 reflections |
b = 9.336 (3) Å | θ = 11.4–20.1° |
c = 12.370 (2) Å | µ = 0.88 mm−1 |
β = 114.82 (3)° | T = 293 K |
V = 1225.4 (6) Å3 | Prism, pale yellow |
Z = 2 | 0.21 × 0.16 × 0.13 mm |
Data collection top
Siemens AED diffractometer | Rint = 0.038 |
Radiation source: fine-focus sealed tube | θmax = 70.1°, θmin = 3.9° |
Graphite monochromator | h = −14→11 |
θ – 2θ scans | k = −5→11 |
2585 measured reflections | l = −14→15 |
2483 independent reflections | 1 standard reflections every 100 reflections |
2446 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1111P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.004 |
2511 reflections | Δρmax = 0.21 e Å−3 |
372 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0058 (7) |
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 | 0.84069 (19) | 0.3137 (2) | 0.04432 (17) | 0.0307 (4) | |
C2 | 0.8089 (2) | 0.4429 (3) | 0.1017 (2) | 0.0452 (6) | |
C3 | 0.9290 (2) | 0.5194 (3) | 0.1817 (2) | 0.0449 (6) | |
C4 | 1.0024 (2) | 0.4252 (2) | 0.29099 (18) | 0.0335 (4) | |
C5 | 0.99885 (17) | 0.2623 (2) | 0.26492 (16) | 0.0256 (4) | |
C6 | 1.13382 (18) | 0.2133 (3) | 0.34700 (18) | 0.0327 (4) | |
C7 | 0.72650 (18) | 0.2144 (2) | −0.02009 (16) | 0.0286 (4) | |
C8 | 0.75578 (16) | 0.0788 (2) | 0.05580 (15) | 0.0238 (4) | |
C9 | 0.90080 (17) | 0.0645 (2) | 0.10313 (15) | 0.0241 (4) | |
C10 | 0.95464 (17) | 0.2194 (2) | 0.13098 (15) | 0.0246 (4) | |
C11 | 0.95394 (18) | −0.0563 (2) | 0.19622 (17) | 0.0309 (4) | |
C12 | 0.8875 (2) | −0.0747 (2) | 0.27903 (17) | 0.0346 (4) | |
C13 | 0.74353 (19) | −0.0568 (3) | 0.21344 (17) | 0.0327 (4) | |
C14 | 0.71415 (18) | 0.0930 (2) | 0.15894 (17) | 0.0293 (4) | |
C15 | 0.69608 (17) | −0.0667 (2) | −0.00044 (15) | 0.0251 (4) | |
C16 | 0.68443 (18) | −0.1478 (2) | 0.10209 (17) | 0.0299 (4) | |
C17 | 0.6225 (2) | −0.2691 (3) | 0.0914 (2) | 0.0412 (5) | |
C18 | 1.1411 (2) | 0.4599 (3) | 0.3412 (2) | 0.0418 (5) | |
C19 | 0.9584 (3) | 0.4550 (4) | 0.3893 (2) | 0.0546 (6) | |
C20 | 1.0647 (2) | 0.2346 (3) | 0.09394 (18) | 0.0368 (5) | |
C21 | 0.56711 (18) | −0.1102 (2) | −0.20594 (16) | 0.0263 (4) | |
C22 | 0.54675 (18) | −0.3324 (2) | −0.30547 (17) | 0.0280 (4) | |
C23 | 0.42753 (18) | −0.2829 (2) | −0.41210 (17) | 0.0293 (4) | |
C24 | 0.43031 (18) | −0.1204 (2) | −0.42344 (17) | 0.0277 (4) | |
C25 | 0.45274 (18) | −0.0452 (2) | −0.30748 (17) | 0.0285 (4) | |
C26 | 0.5528 (2) | −0.4942 (2) | −0.2830 (2) | 0.0365 (5) | |
O1 | 1.21256 (14) | 0.3422 (2) | 0.36876 (15) | 0.0427 (4) | |
O2 | 1.14018 (15) | 0.1622 (2) | 0.45396 (13) | 0.0437 (4) | |
O3 | 1.1867 (2) | 0.5792 (3) | 0.3562 (2) | 0.0725 (7) | |
O4 | 0.71632 (16) | 0.19158 (19) | −0.13861 (12) | 0.0406 (4) | |
O5 | 0.57420 (12) | −0.04957 (16) | −0.10035 (11) | 0.0282 (3) | |
O6 | 0.55316 (14) | −0.26130 (16) | −0.20032 (12) | 0.0315 (3) | |
O7 | 0.67420 (15) | −0.54557 (19) | −0.26418 (14) | 0.0400 (3) | |
O8 | 0.42630 (14) | −0.34697 (18) | −0.51700 (13) | 0.0391 (4) | |
O9 | 0.31556 (14) | −0.0664 (2) | −0.51304 (12) | 0.0397 (4) | |
O10 | 0.47394 (17) | 0.10494 (17) | −0.31335 (13) | 0.0392 (4) | |
H1 | 0.8652 | 0.3511 | −0.0169 | 0.048 (8)* | |
H2A | 0.7548 | 0.5079 | 0.0403 | 0.063 (10)* | |
H2B | 0.7640 | 0.4119 | 0.1480 | 0.055 (9)* | |
H3A | 0.9087 | 0.6106 | 0.2071 | 0.097 (14)* | |
H3B | 0.9801 | 0.5378 | 0.1385 | 0.051 (8)* | |
H5 | 0.9411 | 0.2176 | 0.2938 | 0.027 (6)* | |
H6 | 1.1623 | 0.1399 | 0.3073 | 0.032 (6)* | |
H7 | 0.6495 | 0.2593 | −0.0231 | 0.035 (6)* | |
H9 | 0.9159 | 0.0333 | 0.0346 | 0.025 (5)* | |
H11A | 0.9483 | −0.1459 | 0.1546 | 0.039 (7)* | |
H11B | 1.0425 | −0.0374 | 0.2445 | 0.038 (7)* | |
H12A | 0.9203 | −0.0045 | 0.3426 | 0.037 (7)* | |
H12B | 0.9063 | −0.1691 | 0.3149 | 0.035 (6)* | |
H13 | 0.7027 | −0.0735 | 0.2672 | 0.040 (7)* | |
H14A | 0.7625 | 0.1658 | 0.2157 | 0.025 (5)* | |
H14B | 0.6251 | 0.1150 | 0.1294 | 0.044 (7)* | |
H15 | 0.7533 | −0.1183 | −0.0263 | 0.019 (5)* | |
H17A | 0.6119 | −0.3063 | 0.1564 | 0.074 (11)* | |
H17B | 0.5895 | −0.3174 | 0.0190 | 0.044 (7)* | |
H19A | 0.8690 | 0.4407 | 0.3586 | 0.075 (10)* | |
H19B | 0.9783 | 0.5521 | 0.4162 | 0.092 (13)* | |
H19C | 1.0004 | 0.3908 | 0.4548 | 0.082 (12)* | |
H20A | 1.1250 | 0.1598 | 0.1304 | 0.046 (8)* | |
H20B | 1.1045 | 0.3261 | 0.1195 | 0.048 (8)* | |
H20C | 1.0331 | 0.2275 | 0.0089 | 0.048 (8)* | |
H21 | 0.6438 | −0.0883 | −0.2165 | 0.022 (5)* | |
H22 | 0.6204 | −0.3043 | −0.3192 | 0.017 (5)* | |
H23 | 0.3525 | −0.3119 | −0.4012 | 0.033 (6)* | |
H24 | 0.4992 | −0.0954 | −0.4453 | 0.023 (5)* | |
H25 | 0.3786 | −0.0586 | −0.2908 | 0.031 (6)* | |
H26A | 0.5368 | −0.5142 | −0.2137 | 0.044 (8)* | |
H26B | 0.4888 | −0.5423 | −0.3511 | 0.051 (8)* | |
H2O | 1.1993 | 0.1062 | 0.4827 | 0.061 (10)* | |
H4O | 0.6500 | 0.1502 | −0.1783 | 0.054 (9)* | |
H7O | 0.6917 | −0.6158 | −0.2204 | 0.073 (11)* | |
H8O | 0.3538 | −0.3687 | −0.5619 | 0.054 (9)* | |
H9O | 0.3155 | −0.0780 | −0.5788 | 0.052 (8)* | |
H10O | 0.4914 | 0.1210 | −0.3698 | 0.054 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0379 (9) | 0.0206 (9) | 0.0254 (9) | −0.0029 (8) | 0.0053 (8) | 0.0015 (8) |
C2 | 0.0470 (12) | 0.0224 (10) | 0.0439 (11) | 0.0074 (10) | −0.0031 (10) | −0.0034 (10) |
C3 | 0.0550 (14) | 0.0199 (10) | 0.0410 (11) | 0.0005 (10) | 0.0018 (10) | −0.0039 (10) |
C4 | 0.0382 (10) | 0.0268 (10) | 0.0296 (9) | −0.0021 (9) | 0.0085 (8) | −0.0054 (8) |
C5 | 0.0269 (9) | 0.0262 (10) | 0.0228 (8) | −0.0016 (7) | 0.0097 (7) | −0.0010 (7) |
C6 | 0.0305 (9) | 0.0339 (11) | 0.0301 (9) | −0.0008 (8) | 0.0091 (8) | −0.0016 (8) |
C7 | 0.0319 (9) | 0.0227 (10) | 0.0248 (9) | −0.0011 (8) | 0.0055 (7) | 0.0018 (8) |
C8 | 0.0266 (8) | 0.0206 (9) | 0.0224 (8) | −0.0009 (7) | 0.0085 (7) | −0.0008 (7) |
C9 | 0.0278 (8) | 0.0210 (9) | 0.0229 (8) | −0.0002 (7) | 0.0100 (7) | −0.0022 (7) |
C10 | 0.0296 (8) | 0.0203 (9) | 0.0226 (8) | −0.0018 (7) | 0.0096 (7) | −0.0004 (7) |
C11 | 0.0326 (9) | 0.0208 (9) | 0.0332 (9) | 0.0032 (8) | 0.0077 (8) | 0.0017 (8) |
C12 | 0.0443 (11) | 0.0270 (10) | 0.0240 (8) | −0.0015 (9) | 0.0060 (8) | 0.0049 (8) |
C13 | 0.0412 (10) | 0.0331 (11) | 0.0255 (8) | −0.0042 (9) | 0.0155 (8) | 0.0027 (9) |
C14 | 0.0287 (9) | 0.0312 (10) | 0.0276 (9) | −0.0006 (8) | 0.0116 (7) | −0.0037 (8) |
C15 | 0.0274 (8) | 0.0228 (9) | 0.0222 (8) | −0.0026 (7) | 0.0075 (7) | −0.0013 (7) |
C16 | 0.0317 (9) | 0.0269 (10) | 0.0289 (9) | −0.0024 (8) | 0.0106 (8) | 0.0030 (8) |
C17 | 0.0424 (11) | 0.0362 (12) | 0.0410 (11) | −0.0096 (10) | 0.0136 (9) | 0.0058 (10) |
C18 | 0.0422 (12) | 0.0345 (12) | 0.0370 (10) | −0.0087 (10) | 0.0052 (9) | −0.0067 (10) |
C19 | 0.0702 (16) | 0.0498 (15) | 0.0472 (13) | 0.0053 (14) | 0.0279 (12) | −0.0157 (13) |
C20 | 0.0409 (10) | 0.0404 (12) | 0.0338 (10) | −0.0098 (10) | 0.0204 (9) | −0.0048 (10) |
C21 | 0.0304 (9) | 0.0218 (9) | 0.0260 (9) | −0.0051 (7) | 0.0112 (7) | −0.0030 (7) |
C22 | 0.0311 (8) | 0.0210 (9) | 0.0307 (9) | −0.0035 (8) | 0.0119 (7) | −0.0027 (8) |
C23 | 0.0290 (9) | 0.0266 (10) | 0.0308 (10) | −0.0036 (8) | 0.0110 (7) | −0.0071 (8) |
C24 | 0.0283 (8) | 0.0266 (10) | 0.0240 (9) | 0.0024 (7) | 0.0070 (7) | −0.0009 (8) |
C25 | 0.0334 (9) | 0.0229 (9) | 0.0280 (9) | −0.0006 (8) | 0.0116 (7) | −0.0031 (8) |
C26 | 0.0425 (11) | 0.0236 (10) | 0.0427 (11) | −0.0029 (9) | 0.0172 (9) | −0.0014 (9) |
O1 | 0.0305 (7) | 0.0411 (9) | 0.0481 (9) | −0.0068 (7) | 0.0081 (6) | −0.0039 (7) |
O2 | 0.0432 (8) | 0.0516 (11) | 0.0287 (7) | 0.0082 (8) | 0.0077 (6) | 0.0100 (7) |
O3 | 0.0576 (12) | 0.0420 (11) | 0.0850 (16) | −0.0213 (10) | −0.0024 (11) | −0.0066 (11) |
O4 | 0.0567 (9) | 0.0328 (8) | 0.0232 (7) | −0.0135 (7) | 0.0079 (6) | 0.0010 (6) |
O5 | 0.0277 (6) | 0.0301 (7) | 0.0234 (6) | −0.0016 (6) | 0.0072 (5) | −0.0053 (6) |
O6 | 0.0417 (8) | 0.0218 (7) | 0.0276 (7) | −0.0032 (6) | 0.0114 (6) | −0.0012 (5) |
O7 | 0.0464 (8) | 0.0283 (8) | 0.0431 (8) | 0.0072 (7) | 0.0168 (7) | 0.0111 (7) |
O8 | 0.0401 (8) | 0.0377 (9) | 0.0339 (7) | −0.0006 (7) | 0.0102 (6) | −0.0127 (7) |
O9 | 0.0384 (7) | 0.0438 (9) | 0.0267 (7) | 0.0114 (7) | 0.0037 (6) | −0.0017 (7) |
O10 | 0.0594 (9) | 0.0230 (7) | 0.0315 (7) | 0.0019 (7) | 0.0154 (7) | −0.0029 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.523 (3) | C15—O5 | 1.451 (2) |
C1—C7 | 1.544 (3) | C15—C16 | 1.532 (3) |
C1—C10 | 1.581 (3) | C15—H15 | 0.9800 |
C1—H1 | 0.9800 | C16—C17 | 1.321 (3) |
C2—C3 | 1.515 (3) | C17—H17A | 0.9300 |
C2—H2A | 0.9700 | C17—H17B | 0.9300 |
C2—H2B | 0.9700 | C18—O3 | 1.214 (3) |
C3—C4 | 1.537 (3) | C18—O1 | 1.335 (3) |
C3—H3A | 0.9700 | C19—H19A | 0.9600 |
C3—H3B | 0.9700 | C19—H19B | 0.9600 |
C4—C18 | 1.508 (3) | C19—H19C | 0.9600 |
C4—C19 | 1.532 (3) | C20—H20A | 0.9600 |
C4—C5 | 1.552 (3) | C20—H20B | 0.9600 |
C5—C6 | 1.544 (3) | C20—H20C | 0.9600 |
C5—C10 | 1.566 (2) | C21—O5 | 1.394 (2) |
C5—H5 | 0.9800 | C21—O6 | 1.425 (2) |
C6—O2 | 1.379 (3) | C21—C25 | 1.524 (3) |
C6—O1 | 1.470 (3) | C21—H21 | 0.9800 |
C6—H6 | 0.9800 | C22—O6 | 1.434 (2) |
C7—O4 | 1.436 (2) | C22—C26 | 1.532 (3) |
C7—C8 | 1.527 (3) | C22—C23 | 1.534 (3) |
C7—H7 | 0.9800 | C22—H22 | 0.9800 |
C8—C9 | 1.550 (2) | C23—O8 | 1.423 (2) |
C8—C14 | 1.550 (2) | C23—C24 | 1.525 (3) |
C8—C15 | 1.552 (3) | C23—H23 | 0.9800 |
C9—C11 | 1.544 (3) | C24—O9 | 1.426 (2) |
C9—C10 | 1.557 (3) | C24—C25 | 1.518 (3) |
C9—H9 | 0.9800 | C24—H24 | 0.9800 |
C10—C20 | 1.543 (3) | C25—O10 | 1.431 (3) |
C11—C12 | 1.533 (3) | C25—H25 | 0.9800 |
C11—H11A | 0.9700 | C26—O7 | 1.422 (3) |
C11—H11B | 0.9700 | C26—H26A | 0.9700 |
C12—C13 | 1.540 (3) | C26—H26B | 0.9700 |
C12—H12A | 0.9700 | O2—H2O | 0.8200 |
C12—H12B | 0.9700 | O4—H4O | 0.8200 |
C13—C16 | 1.516 (3) | O7—H7O | 0.8200 |
C13—C14 | 1.528 (3) | O8—H8O | 0.8200 |
C13—H13 | 0.9800 | O9—H9O | 0.8200 |
C14—H14A | 0.9700 | O10—H10O | 0.8200 |
C14—H14B | 0.9700 | | |
| | | |
C2—C1—C7 | 112.88 (18) | C13—C14—C8 | 101.23 (15) |
C2—C1—C10 | 115.23 (16) | C13—C14—H14A | 111.5 |
C7—C1—C10 | 108.41 (16) | C8—C14—H14A | 111.5 |
C2—C1—H1 | 106.6 | C13—C14—H14B | 111.5 |
C7—C1—H1 | 106.6 | C8—C14—H14B | 111.5 |
C10—C1—H1 | 106.6 | H14A—C14—H14B | 109.3 |
C3—C2—C1 | 109.7 (2) | O5—C15—C16 | 111.28 (15) |
C3—C2—H2A | 109.7 | O5—C15—C8 | 112.44 (16) |
C1—C2—H2A | 109.7 | C16—C15—C8 | 103.95 (14) |
C3—C2—H2B | 109.7 | O5—C15—H15 | 109.7 |
C1—C2—H2B | 109.7 | C16—C15—H15 | 109.7 |
H2A—C2—H2B | 108.2 | C8—C15—H15 | 109.7 |
C2—C3—C4 | 109.1 (2) | C17—C16—C13 | 126.4 (2) |
C2—C3—H3A | 109.9 | C17—C16—C15 | 125.24 (19) |
C4—C3—H3A | 109.9 | C13—C16—C15 | 108.09 (17) |
C2—C3—H3B | 109.9 | C16—C17—H17A | 120.0 |
C4—C3—H3B | 109.9 | C16—C17—H17B | 120.0 |
H3A—C3—H3B | 108.3 | H17A—C17—H17B | 120.0 |
C18—C4—C19 | 107.19 (19) | O3—C18—O1 | 121.9 (2) |
C18—C4—C3 | 110.3 (2) | O3—C18—C4 | 125.9 (2) |
C19—C4—C3 | 110.2 (2) | O1—C18—C4 | 112.2 (2) |
C18—C4—C5 | 103.08 (18) | C4—C19—H19A | 109.5 |
C19—C4—C5 | 110.7 (2) | C4—C19—H19B | 109.5 |
C3—C4—C5 | 114.94 (17) | H19A—C19—H19B | 109.5 |
C6—C5—C4 | 102.87 (16) | C4—C19—H19C | 109.5 |
C6—C5—C10 | 114.34 (15) | H19A—C19—H19C | 109.5 |
C4—C5—C10 | 116.01 (16) | H19B—C19—H19C | 109.5 |
C6—C5—H5 | 107.7 | C10—C20—H20A | 109.5 |
C4—C5—H5 | 107.7 | C10—C20—H20B | 109.5 |
C10—C5—H5 | 107.7 | H20A—C20—H20B | 109.5 |
O2—C6—O1 | 109.29 (17) | C10—C20—H20C | 109.5 |
O2—C6—C5 | 111.22 (16) | H20A—C20—H20C | 109.5 |
O1—C6—C5 | 105.45 (17) | H20B—C20—H20C | 109.5 |
O2—C6—H6 | 110.3 | O5—C21—O6 | 108.62 (16) |
O1—C6—H6 | 110.3 | O5—C21—C25 | 107.28 (15) |
C5—C6—H6 | 110.3 | O6—C21—C25 | 110.82 (16) |
O4—C7—C8 | 113.96 (16) | O5—C21—H21 | 110.0 |
O4—C7—C1 | 107.39 (16) | O6—C21—H21 | 110.0 |
C8—C7—C1 | 104.98 (14) | C25—C21—H21 | 110.0 |
O4—C7—H7 | 110.1 | O6—C22—C26 | 108.12 (17) |
C8—C7—H7 | 110.1 | O6—C22—C23 | 108.87 (16) |
C1—C7—H7 | 110.1 | C26—C22—C23 | 114.12 (17) |
C7—C8—C9 | 103.34 (15) | O6—C22—H22 | 108.5 |
C7—C8—C14 | 111.61 (16) | C26—C22—H22 | 108.5 |
C9—C8—C14 | 111.60 (14) | C23—C22—H22 | 108.5 |
C7—C8—C15 | 120.49 (14) | O8—C23—C24 | 109.05 (17) |
C9—C8—C15 | 108.01 (15) | O8—C23—C22 | 108.38 (16) |
C14—C8—C15 | 101.91 (15) | C24—C23—C22 | 109.37 (16) |
C11—C9—C8 | 112.23 (15) | O8—C23—H23 | 110.0 |
C11—C9—C10 | 120.99 (15) | C24—C23—H23 | 110.0 |
C8—C9—C10 | 106.29 (14) | C22—C23—H23 | 110.0 |
C11—C9—H9 | 105.4 | O9—C24—C25 | 107.68 (16) |
C8—C9—H9 | 105.4 | O9—C24—C23 | 111.96 (17) |
C10—C9—H9 | 105.4 | C25—C24—C23 | 112.04 (17) |
C20—C10—C9 | 109.26 (16) | O9—C24—H24 | 108.3 |
C20—C10—C5 | 110.15 (15) | C25—C24—H24 | 108.3 |
C9—C10—C5 | 113.25 (15) | C23—C24—H24 | 108.3 |
C20—C10—C1 | 108.53 (16) | O10—C25—C24 | 111.74 (17) |
C9—C10—C1 | 102.68 (14) | O10—C25—C21 | 108.73 (16) |
C5—C10—C1 | 112.64 (15) | C24—C25—C21 | 109.77 (16) |
C12—C11—C9 | 114.97 (16) | O10—C25—H25 | 108.9 |
C12—C11—H11A | 108.5 | C24—C25—H25 | 108.9 |
C9—C11—H11A | 108.5 | C21—C25—H25 | 108.9 |
C12—C11—H11B | 108.5 | O7—C26—C22 | 109.25 (18) |
C9—C11—H11B | 108.5 | O7—C26—H26A | 109.8 |
H11A—C11—H11B | 107.5 | C22—C26—H26A | 109.8 |
C11—C12—C13 | 112.59 (15) | O7—C26—H26B | 109.8 |
C11—C12—H12A | 109.1 | C22—C26—H26B | 109.8 |
C13—C12—H12A | 109.1 | H26A—C26—H26B | 108.3 |
C11—C12—H12B | 109.1 | C18—O1—C6 | 110.53 (16) |
C13—C12—H12B | 109.1 | C6—O2—H2O | 109.5 |
H12A—C12—H12B | 107.8 | C7—O4—H4O | 109.5 |
C16—C13—C14 | 100.35 (15) | C21—O5—C15 | 113.86 (15) |
C16—C13—C12 | 113.49 (18) | C21—O6—C22 | 112.16 (15) |
C14—C13—C12 | 108.97 (17) | C26—O7—H7O | 109.5 |
C16—C13—H13 | 111.2 | C23—O8—H8O | 109.5 |
C14—C13—H13 | 111.2 | C24—O9—H9O | 109.5 |
C12—C13—H13 | 111.2 | C25—O10—H10O | 109.5 |
| | | |
C7—C1—C2—C3 | 169.46 (19) | C16—C13—C14—C8 | −47.65 (17) |
C10—C1—C2—C3 | 44.2 (3) | C12—C13—C14—C8 | 71.76 (18) |
C1—C2—C3—C4 | −69.6 (3) | C7—C8—C14—C13 | 175.78 (14) |
C2—C3—C4—C18 | 154.2 (2) | C9—C8—C14—C13 | −69.15 (19) |
C2—C3—C4—C19 | −87.7 (3) | C15—C8—C14—C13 | 45.89 (17) |
C2—C3—C4—C5 | 38.3 (3) | C7—C8—C15—O5 | −29.2 (2) |
C18—C4—C5—C6 | 21.6 (2) | C9—C8—C15—O5 | −147.43 (14) |
C19—C4—C5—C6 | −92.7 (2) | C14—C8—C15—O5 | 94.91 (16) |
C3—C4—C5—C6 | 141.6 (2) | C7—C8—C15—C16 | −149.68 (17) |
C18—C4—C5—C10 | −103.97 (19) | C9—C8—C15—C16 | 92.10 (16) |
C19—C4—C5—C10 | 141.67 (18) | C14—C8—C15—C16 | −25.56 (17) |
C3—C4—C5—C10 | 16.0 (3) | C14—C13—C16—C17 | −141.8 (2) |
C4—C5—C6—O2 | 94.6 (2) | C12—C13—C16—C17 | 102.2 (2) |
C10—C5—C6—O2 | −138.72 (18) | C14—C13—C16—C15 | 32.10 (19) |
C4—C5—C6—O1 | −23.74 (19) | C12—C13—C16—C15 | −84.0 (2) |
C10—C5—C6—O1 | 102.92 (18) | O5—C15—C16—C17 | 48.8 (3) |
C2—C1—C7—O4 | 128.29 (18) | C8—C15—C16—C17 | 170.1 (2) |
C10—C1—C7—O4 | −102.80 (17) | O5—C15—C16—C13 | −125.15 (18) |
C2—C1—C7—C8 | −110.08 (19) | C8—C15—C16—C13 | −3.90 (19) |
C10—C1—C7—C8 | 18.8 (2) | C19—C4—C18—O3 | −75.8 (3) |
O4—C7—C8—C9 | 82.76 (18) | C3—C4—C18—O3 | 44.1 (4) |
C1—C7—C8—C9 | −34.47 (18) | C5—C4—C18—O3 | 167.3 (3) |
O4—C7—C8—C14 | −157.19 (16) | C19—C4—C18—O1 | 104.2 (2) |
C1—C7—C8—C14 | 85.59 (18) | C3—C4—C18—O1 | −135.9 (2) |
O4—C7—C8—C15 | −37.8 (2) | C5—C4—C18—O1 | −12.7 (2) |
C1—C7—C8—C15 | −155.01 (16) | O6—C22—C23—O8 | 176.33 (16) |
C7—C8—C9—C11 | 172.61 (15) | C26—C22—C23—O8 | −62.8 (2) |
C14—C8—C9—C11 | 52.5 (2) | O6—C22—C23—C24 | 57.5 (2) |
C15—C8—C9—C11 | −58.69 (18) | C26—C22—C23—C24 | 178.42 (18) |
C7—C8—C9—C10 | 38.27 (17) | O8—C23—C24—O9 | 68.0 (2) |
C14—C8—C9—C10 | −81.79 (18) | C22—C23—C24—O9 | −173.62 (14) |
C15—C8—C9—C10 | 166.98 (14) | O8—C23—C24—C25 | −170.89 (14) |
C11—C9—C10—C20 | 89.6 (2) | C22—C23—C24—C25 | −52.5 (2) |
C8—C9—C10—C20 | −140.97 (15) | O9—C24—C25—O10 | −65.1 (2) |
C11—C9—C10—C5 | −33.6 (2) | C23—C24—C25—O10 | 171.32 (16) |
C8—C9—C10—C5 | 95.85 (16) | O9—C24—C25—C21 | 174.15 (16) |
C11—C9—C10—C1 | −155.33 (16) | C23—C24—C25—C21 | 50.6 (2) |
C8—C9—C10—C1 | −25.90 (18) | O5—C21—C25—O10 | 64.51 (19) |
C6—C5—C10—C20 | −38.6 (2) | O6—C21—C25—O10 | −177.06 (15) |
C4—C5—C10—C20 | 81.0 (2) | O5—C21—C25—C24 | −172.98 (15) |
C6—C5—C10—C9 | 84.13 (19) | O6—C21—C25—C24 | −54.5 (2) |
C4—C5—C10—C9 | −156.35 (16) | O6—C22—C26—O7 | −105.27 (19) |
C6—C5—C10—C1 | −159.89 (16) | C23—C22—C26—O7 | 133.43 (18) |
C4—C5—C10—C1 | −40.4 (2) | O3—C18—O1—C6 | 177.3 (3) |
C2—C1—C10—C20 | −112.4 (2) | C4—C18—O1—C6 | −2.7 (3) |
C7—C1—C10—C20 | 120.01 (18) | O2—C6—O1—C18 | −102.4 (2) |
C2—C1—C10—C9 | 131.99 (19) | C5—C6—O1—C18 | 17.2 (2) |
C7—C1—C10—C9 | 4.41 (19) | O6—C21—O5—C15 | 77.48 (19) |
C2—C1—C10—C5 | 9.8 (2) | C25—C21—O5—C15 | −162.68 (15) |
C7—C1—C10—C5 | −117.74 (17) | C16—C15—O5—C21 | −120.89 (17) |
C8—C9—C11—C12 | −36.1 (2) | C8—C15—O5—C21 | 122.96 (16) |
C10—C9—C11—C12 | 90.7 (2) | O5—C21—O6—C22 | −179.25 (14) |
C9—C11—C12—C13 | 39.9 (3) | C25—C21—O6—C22 | 63.1 (2) |
C11—C12—C13—C16 | 51.1 (2) | C26—C22—O6—C21 | 171.24 (16) |
C11—C12—C13—C14 | −59.8 (2) | C23—C22—O6—C21 | −64.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O5 | 0.82 | 2.43 | 2.952 (2) | 122 |
O4—H4O···O10 | 0.82 | 2.08 | 2.866 (3) | 161 |
O2—H2O···O9i | 0.82 | 2.09 | 2.868 (3) | 157 |
O8—H8O···O3ii | 0.82 | 1.85 | 2.664 (3) | 172 |
O9—H9O···O7iii | 0.82 | 2.02 | 2.815 (2) | 164 |
O10—H10O···O8iii | 0.82 | 2.03 | 2.832 (2) | 168 |
O7—H7O···O4iv | 0.82 | 2.02 | 2.835 (2) | 170 |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y−1, z−1; (iii) −x+1, y+1/2, −z−1; (iv) x, y−1, z. |
Ring-puckering parameters (Å, °) for five rings topRing | q2 | q3 | QT | θ |
A(C1-C2-C3-C4-C5-C10) | 0.672 (2) | -0.133 (2) | 0.685 (2) | 101.2 (2) |
B(C1-C7-C8-C9-C10) | 0.372 (2) | | | |
C(C8-C9-C11-C12-C13-C14) | 0.260 (2) | -0.570 (2) | 0.627 (2) | 155.5 (2) |
D(C4-C5-C6-O1-C18) | 0.242 (2) | | | |
E(C21-O6-C22-C23-C24-C25) | 0.056 (2) | -0.572 (2) | 0.574 (2) | 174.4 (2) |
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