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Two minor compounds were isolated from a sample of Harrisonia perforata leaves collected in central Vietnam, namely haperforin B1, C27H32O9, and haperforin D, C27H34O10. Biogenetically, haperforin D and haperforin B1 can be derived from each other by addition or elimination of water.
Supporting information
CCDC references: 146067; 146068
For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NONIUS (Riche, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: R3M (Riche, 1983) and ORTEP (Johnson, 1965).
(B1) methyl 4-(3,6-dihydro-2,2-dimethyl-6-oxo-2
H-pyran-3-ylideneacetyl)-8-
furanoyl-5-(1-hydroxyethyl)-4,8-dimethyl-1-oxaspiro[2.5]octane-2-carboxylate
top
Crystal data top
C27H32O9 | Dx = 1.301 Mg m−3 |
Mr = 500.53 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 12.216 (4) Å | θ = 14.0–22.1° |
b = 12.463 (5) Å | µ = 0.81 mm−1 |
c = 16.781 (7) Å | T = 293 K |
V = 2554.9 (17) Å3 | Prism, colorless |
Z = 4 | 0.53 × 0.26 × 0.2 mm |
F(000) = 1064 | |
Data collection top
Nonius CAD4 diffractometer | Rint = 0.026 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 4.4° |
Graphite monochromator | h = −10→14 |
θ/2θ scans | k = 0→14 |
3271 measured reflections | l = 0→19 |
2327 independent reflections | 3 standard reflections every 120 min |
2192 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.08 | Calculated w = 1/[σ2(Fo2) + (0.0859P)2 + 0.5597P] where P = (Fo2 + 2Fc2)/3 |
2327 reflections | (Δ/σ)max = −0.004 |
325 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.26 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 on F2 for ALL reflections except for 0 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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 | 0.0596 (3) | 0.0522 (2) | 0.1814 (2) | 0.0393 (7) | |
C2 | 0.0238 (3) | 0.1355 (3) | 0.1232 (2) | 0.0448 (8) | |
H2 | 0.0486 | 0.2052 | 0.1310 | 0.054* | |
C3 | −0.0409 (3) | 0.1173 (3) | 0.0609 (2) | 0.0427 (7) | |
C4 | −0.0764 (3) | 0.2090 (3) | 0.0070 (2) | 0.0495 (8) | |
C5 | −0.2185 (4) | 0.0890 (4) | −0.0459 (2) | 0.0654 (11) | |
C6 | −0.1524 (4) | −0.0003 (4) | −0.0205 (3) | 0.0687 (12) | |
H6 | −0.1654 | −0.0677 | −0.0423 | 0.082* | |
C7 | −0.0732 (4) | 0.0107 (3) | 0.0334 (2) | 0.0567 (10) | |
H7 | −0.0382 | −0.0497 | 0.0537 | 0.068* | |
C8 | 0.1694 (2) | 0.0694 (2) | 0.2253 (2) | 0.0332 (6) | |
C9 | 0.2135 (3) | −0.0419 (2) | 0.2518 (2) | 0.0373 (7) | |
H9 | 0.1539 | −0.0800 | 0.2788 | 0.045* | |
C10 | 0.2522 (3) | −0.1117 (3) | 0.1818 (2) | 0.0555 (9) | |
H10 | 0.3275 | −0.0899 | 0.1697 | 0.067* | |
C11 | 0.3086 (3) | −0.0301 (2) | 0.3113 (2) | 0.0447 (8) | |
H11A | 0.3269 | −0.1006 | 0.3320 | 0.054* | |
H11B | 0.3722 | −0.0033 | 0.2830 | 0.054* | |
C12 | 0.2851 (3) | 0.0437 (2) | 0.3808 (2) | 0.0435 (8) | |
H12A | 0.3510 | 0.0508 | 0.4126 | 0.052* | |
H12B | 0.2294 | 0.0111 | 0.4141 | 0.052* | |
C13 | 0.2462 (3) | 0.1566 (2) | 0.3560 (2) | 0.0370 (7) | |
C14 | 0.1466 (2) | 0.1366 (2) | 0.3015 (2) | 0.0302 (6) | |
C15 | 0.0341 (3) | 0.1297 (2) | 0.3362 (2) | 0.0384 (7) | |
H15 | −0.0148 | 0.0812 | 0.3073 | 0.046* | |
C16 | −0.0005 (3) | 0.1508 (3) | 0.4200 (2) | 0.0447 (8) | |
C17 | 0.3415 (3) | 0.2205 (3) | 0.3173 (2) | 0.0406 (7) | |
C18 | 0.2210 (3) | 0.2221 (3) | 0.4325 (2) | 0.0469 (8) | |
H18A | 0.1966 | 0.2927 | 0.4179 | 0.056* | |
H18B | 0.2861 | 0.2276 | 0.4643 | 0.056* | |
H18C | 0.1647 | 0.1867 | 0.4625 | 0.056* | |
C19 | 0.2559 (5) | −0.2296 (3) | 0.2035 (3) | 0.089 (2) | |
H19A | 0.2803 | −0.2704 | 0.1583 | 0.107* | |
H19B | 0.1841 | −0.2531 | 0.2188 | 0.107* | |
H19C | 0.3057 | −0.2400 | 0.2471 | 0.107* | |
C20 | 0.3264 (3) | 0.3311 (3) | 0.2884 (2) | 0.0402 (7) | |
C21 | 0.2381 (3) | 0.3964 (3) | 0.2856 (3) | 0.0558 (10) | |
H21 | 0.1677 | 0.3759 | 0.3003 | 0.067* | |
C22 | 0.4146 (3) | 0.3953 (3) | 0.2594 (2) | 0.0517 (9) | |
H22 | 0.4869 | 0.3733 | 0.2533 | 0.062* | |
C23 | 0.3755 (4) | 0.4915 (3) | 0.2427 (3) | 0.0619 (11) | |
H23 | 0.4165 | 0.5484 | 0.2229 | 0.074* | |
C28 | −0.0912 (5) | 0.3139 (3) | 0.0502 (3) | 0.0765 (14) | |
H28A | −0.1410 | 0.3041 | 0.0939 | 0.092* | |
H28B | −0.1203 | 0.3665 | 0.0142 | 0.092* | |
H28C | −0.0218 | 0.3379 | 0.0702 | 0.092* | |
C29 | 0.0011 (4) | 0.2205 (4) | −0.0620 (2) | 0.0668 (11) | |
H29A | 0.0089 | 0.1525 | −0.0884 | 0.080* | |
H29B | 0.0712 | 0.2438 | −0.0429 | 0.080* | |
H29C | −0.0273 | 0.2724 | −0.0989 | 0.080* | |
C30 | 0.2491 (3) | 0.1279 (3) | 0.1690 (2) | 0.0421 (7) | |
H30A | 0.3177 | 0.1391 | 0.1956 | 0.051* | |
H30B | 0.2185 | 0.1960 | 0.1540 | 0.051* | |
H30C | 0.2607 | 0.0852 | 0.1221 | 0.051* | |
C31 | −0.0265 (4) | 0.0677 (4) | 0.5448 (2) | 0.0664 (11) | |
H31A | −0.0126 | 0.0005 | 0.5709 | 0.080* | |
H31B | −0.1038 | 0.0816 | 0.5446 | 0.080* | |
H31C | 0.0105 | 0.1243 | 0.5728 | 0.080* | |
O1 | 0.0010 (2) | −0.0229 (2) | 0.19693 (15) | 0.0531 (6) | |
O4 | −0.1860 (2) | 0.1882 (2) | −0.0261 (2) | 0.0660 (8) | |
O7 | −0.3039 (3) | 0.0793 (4) | −0.0824 (2) | 0.0964 (12) | |
O10 | 0.1900 (3) | −0.0965 (2) | 0.11050 (15) | 0.0639 (7) | |
HO10 | 0.1324 | −0.1300 | 0.11372 | 0.077* | |
O14 | 0.0676 (2) | 0.2218 (2) | 0.29068 (13) | 0.0397 (5) | |
O16 | −0.0422 (2) | 0.2327 (2) | 0.4432 (2) | 0.0601 (7) | |
O16' | 0.0131 (2) | 0.0629 (2) | 0.46411 (14) | 0.0504 (6) | |
O17 | 0.4332 (2) | 0.1828 (2) | 0.3173 (2) | 0.0582 (7) | |
O21 | 0.2651 (2) | 0.4948 (2) | 0.2589 (2) | 0.0685 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.041 (2) | 0.043 (2) | 0.034 (2) | −0.0027 (14) | −0.0045 (15) | −0.0004 (13) |
C2 | 0.053 (2) | 0.041 (2) | 0.041 (2) | −0.0009 (15) | −0.008 (2) | 0.0019 (13) |
C3 | 0.051 (2) | 0.046 (2) | 0.031 (2) | 0.0026 (15) | −0.004 (2) | 0.0019 (14) |
C4 | 0.053 (2) | 0.047 (2) | 0.048 (2) | 0.007 (2) | −0.008 (2) | 0.002 (2) |
C5 | 0.057 (2) | 0.086 (3) | 0.053 (2) | −0.009 (2) | −0.005 (2) | 0.011 (2) |
C6 | 0.088 (3) | 0.062 (2) | 0.056 (2) | −0.020 (2) | −0.025 (2) | 0.002 (2) |
C7 | 0.077 (3) | 0.049 (2) | 0.044 (2) | −0.002 (2) | −0.015 (2) | 0.002 (2) |
C8 | 0.0352 (14) | 0.0333 (13) | 0.0313 (15) | −0.0009 (11) | −0.0008 (14) | −0.0013 (12) |
C9 | 0.0359 (15) | 0.0344 (15) | 0.042 (2) | 0.0020 (12) | 0.0006 (14) | 0.0005 (13) |
C10 | 0.055 (2) | 0.046 (2) | 0.065 (2) | 0.003 (2) | 0.004 (2) | −0.017 (2) |
C11 | 0.039 (2) | 0.0404 (15) | 0.054 (2) | 0.0051 (13) | −0.008 (2) | 0.0029 (14) |
C12 | 0.044 (2) | 0.040 (2) | 0.047 (2) | 0.0021 (14) | −0.008 (2) | 0.0057 (14) |
C13 | 0.0366 (15) | 0.0377 (14) | 0.037 (2) | −0.0019 (13) | −0.0053 (14) | 0.0023 (13) |
C14 | 0.0279 (12) | 0.0307 (12) | 0.032 (2) | −0.0005 (11) | −0.0004 (13) | 0.0008 (11) |
C15 | 0.0350 (14) | 0.0383 (15) | 0.042 (2) | 0.0005 (12) | 0.0029 (14) | −0.0014 (13) |
C16 | 0.042 (2) | 0.042 (2) | 0.050 (2) | 0.0033 (15) | 0.003 (2) | 0.0005 (14) |
C17 | 0.0360 (15) | 0.044 (2) | 0.042 (2) | −0.0023 (13) | −0.0009 (15) | −0.0059 (14) |
C18 | 0.050 (2) | 0.051 (2) | 0.039 (2) | −0.010 (2) | −0.004 (2) | −0.0059 (15) |
C19 | 0.116 (4) | 0.048 (2) | 0.102 (4) | 0.026 (3) | −0.027 (4) | −0.023 (2) |
C20 | 0.038 (2) | 0.043 (2) | 0.039 (2) | −0.0077 (13) | 0.0006 (14) | −0.0022 (14) |
C21 | 0.050 (2) | 0.037 (2) | 0.081 (3) | −0.0021 (15) | 0.006 (2) | 0.006 (2) |
C22 | 0.046 (2) | 0.057 (2) | 0.052 (2) | −0.012 (2) | 0.003 (2) | 0.001 (2) |
C23 | 0.064 (2) | 0.055 (2) | 0.066 (3) | −0.018 (2) | 0.006 (2) | 0.008 (2) |
C28 | 0.106 (4) | 0.051 (2) | 0.072 (3) | 0.024 (2) | −0.018 (3) | −0.004 (2) |
C29 | 0.076 (3) | 0.074 (3) | 0.051 (2) | 0.003 (2) | 0.002 (2) | 0.018 (2) |
C30 | 0.046 (2) | 0.047 (2) | 0.034 (2) | −0.0084 (14) | 0.006 (2) | 0.0021 (13) |
C31 | 0.082 (3) | 0.073 (2) | 0.044 (2) | 0.006 (2) | 0.016 (2) | 0.007 (2) |
O1 | 0.0506 (13) | 0.0567 (13) | 0.0521 (14) | −0.0171 (11) | −0.0092 (13) | 0.0090 (12) |
O4 | 0.058 (2) | 0.069 (2) | 0.071 (2) | 0.0086 (14) | −0.0160 (15) | 0.0051 (15) |
O7 | 0.067 (2) | 0.134 (3) | 0.088 (2) | −0.021 (2) | −0.030 (2) | 0.018 (2) |
O10 | 0.085 (2) | 0.0597 (15) | 0.0475 (14) | −0.0137 (15) | 0.004 (2) | −0.0097 (12) |
O14 | 0.0389 (11) | 0.0360 (10) | 0.0441 (12) | 0.0073 (9) | 0.0013 (10) | 0.0034 (9) |
O16 | 0.069 (2) | 0.0582 (14) | 0.0536 (15) | 0.0233 (14) | 0.0154 (14) | −0.0015 (12) |
O16' | 0.0587 (14) | 0.0461 (12) | 0.0463 (13) | 0.0029 (11) | 0.0134 (13) | 0.0031 (10) |
O17 | 0.0327 (11) | 0.0545 (14) | 0.088 (2) | 0.0006 (10) | −0.0012 (13) | −0.0017 (14) |
O21 | 0.067 (2) | 0.0425 (12) | 0.096 (2) | −0.0025 (12) | 0.007 (2) | 0.0121 (14) |
Geometric parameters (Å, º) top
C1—O1 | 1.207 (4) | C11—C12 | 1.513 (5) |
C1—C2 | 1.490 (4) | C12—C13 | 1.541 (4) |
C1—C8 | 1.547 (4) | C13—C14 | 1.543 (4) |
C2—C3 | 1.330 (5) | C13—C18 | 1.552 (5) |
C3—C7 | 1.460 (5) | C13—C17 | 1.554 (4) |
C3—C4 | 1.521 (5) | C14—O14 | 1.446 (3) |
C4—O4 | 1.472 (5) | C14—C15 | 1.494 (4) |
C4—C29 | 1.503 (6) | C15—O14 | 1.438 (4) |
C4—C28 | 1.506 (5) | C15—C16 | 1.492 (5) |
C5—O7 | 1.216 (5) | C16—O16 | 1.206 (4) |
C5—O4 | 1.340 (5) | C16—O16' | 1.332 (4) |
C5—C6 | 1.440 (6) | C17—O17 | 1.215 (4) |
C6—C7 | 1.332 (6) | C17—C20 | 1.473 (5) |
C8—C30 | 1.540 (4) | C20—C21 | 1.351 (5) |
C8—C14 | 1.553 (4) | C20—C22 | 1.429 (5) |
C8—C9 | 1.553 (4) | C21—O21 | 1.347 (4) |
C9—C10 | 1.537 (5) | C22—C23 | 1.320 (6) |
C9—C11 | 1.538 (4) | C23—O21 | 1.377 (5) |
C10—O10 | 1.429 (5) | C31—O16' | 1.439 (5) |
C10—C19 | 1.515 (6) | | |
| | | |
O1—C1—C2 | 120.5 (3) | C12—C13—C14 | 104.9 (2) |
O1—C1—C8 | 121.3 (3) | C12—C13—C18 | 108.6 (3) |
C2—C1—C8 | 118.1 (3) | C14—C13—C18 | 114.8 (3) |
C3—C2—C1 | 124.8 (3) | C12—C13—C17 | 110.4 (3) |
C2—C3—C7 | 124.3 (3) | C14—C13—C17 | 115.2 (3) |
C2—C3—C4 | 120.6 (3) | C18—C13—C17 | 103.0 (2) |
C7—C3—C4 | 114.8 (3) | O14—C14—C15 | 58.5 (2) |
O4—C4—C29 | 107.4 (3) | O14—C14—C13 | 118.9 (2) |
O4—C4—C28 | 103.0 (3) | C15—C14—C13 | 120.1 (3) |
C29—C4—C28 | 111.4 (4) | O14—C14—C8 | 114.4 (2) |
O4—C4—C3 | 110.5 (3) | C15—C14—C8 | 117.1 (2) |
C29—C4—C3 | 110.5 (3) | C13—C14—C8 | 115.7 (2) |
C28—C4—C3 | 113.6 (3) | O14—C15—C16 | 116.2 (3) |
O7—C5—O4 | 118.1 (4) | O14—C15—C14 | 59.0 (2) |
O7—C5—C6 | 123.6 (5) | C16—C15—C14 | 128.2 (3) |
O4—C5—C6 | 118.3 (4) | O16—C16—O16' | 124.7 (3) |
C7—C6—C5 | 121.9 (4) | O16—C16—C15 | 124.9 (3) |
C6—C7—C3 | 120.3 (4) | O16'—C16—C15 | 110.1 (3) |
C30—C8—C1 | 108.7 (2) | O17—C17—C20 | 118.6 (3) |
C30—C8—C14 | 111.3 (2) | O17—C17—C13 | 119.5 (3) |
C1—C8—C14 | 108.1 (2) | C20—C17—C13 | 121.5 (3) |
C30—C8—C9 | 112.3 (2) | C21—C20—C22 | 104.6 (3) |
C1—C8—C9 | 108.3 (2) | C21—C20—C17 | 132.5 (3) |
C14—C8—C9 | 108.0 (2) | C22—C20—C17 | 122.8 (3) |
C10—C9—C11 | 108.6 (3) | O21—C21—C20 | 111.4 (3) |
C10—C9—C8 | 113.2 (3) | C23—C22—C20 | 108.0 (3) |
C11—C9—C8 | 111.3 (2) | C22—C23—O21 | 109.9 (3) |
O10—C10—C19 | 110.2 (3) | C5—O4—C4 | 121.7 (3) |
O10—C10—C9 | 113.7 (3) | C15—O14—C14 | 62.4 (2) |
C19—C10—C9 | 112.0 (4) | C16—O16'—C31 | 116.5 (3) |
C12—C11—C9 | 114.5 (3) | C21—O21—C23 | 106.1 (3) |
C11—C12—C13 | 114.0 (3) | | |
| | | |
O1—C1—C2—C3 | −31.3 (5) | C18—C13—C14—C8 | −179.0 (2) |
C8—C1—C2—C3 | 153.1 (3) | C17—C13—C14—C8 | 61.7 (3) |
C1—C2—C3—C7 | −9.7 (6) | C30—C8—C14—O14 | 79.6 (3) |
C1—C2—C3—C4 | 177.4 (3) | C1—C8—C14—O14 | −39.7 (3) |
C7—C3—C4—O4 | 37.8 (4) | C9—C8—C14—O14 | −156.7 (2) |
C3—C4—O4—C5 | −35.9 (5) | C30—C8—C14—C15 | 145.3 (3) |
C4—O4—C5—C6 | 11.6 (6) | C1—C8—C14—C15 | 25.9 (3) |
O4—C5—C6—C7 | 12.6 (7) | C9—C8—C14—C15 | −91.0 (3) |
C5—C6—C7—C3 | −8.2 (7) | C30—C8—C14—C13 | −64.1 (3) |
C6—C7—C3—C4 | −18.2 (6) | C1—C8—C14—C13 | 176.6 (2) |
C8—C9—C10—O10 | −33.8 (4) | C9—C8—C14—C13 | 59.6 (3) |
C13—C14—C15—C16 | 6.8 (4) | O14—C14—C15—O14 | 0.0 |
C14—C15—C16—O16 | 99.9 (4) | C13—C14—C15—O14 | 107.4 (3) |
C2—C3—C4—O4 | −148.7 (3) | C8—C14—C15—O14 | −103.4 (3) |
C2—C3—C4—C29 | 92.6 (4) | O14—C14—C15—C16 | −100.6 (3) |
C7—C3—C4—C29 | −80.9 (4) | C13—C14—C15—C16 | 6.8 (4) |
C2—C3—C4—C28 | −33.4 (5) | C8—C14—C15—C16 | 156.1 (3) |
C7—C3—C4—C28 | 153.0 (4) | O14—C15—C16—O16 | 30.0 (5) |
O7—C5—C6—C7 | −165.2 (5) | C14—C15—C16—O16 | 99.9 (4) |
C2—C3—C7—C6 | 168.6 (4) | O14—C15—C16—O16' | −155.1 (3) |
O1—C1—C8—C30 | 151.0 (3) | C14—C15—C16—O16' | −85.1 (4) |
C2—C1—C8—C30 | −33.4 (4) | C12—C13—C17—O17 | −6.8 (4) |
O1—C1—C8—C9 | 28.7 (4) | C14—C13—C17—O17 | −125.3 (3) |
C2—C1—C8—C9 | −155.7 (3) | C18—C13—C17—O17 | 109.0 (3) |
O1—C1—C8—C14 | −88.0 (3) | C12—C13—C17—C20 | −179.9 (3) |
C2—C1—C8—C14 | 87.6 (3) | C14—C13—C17—C20 | 61.6 (4) |
C30—C8—C9—C10 | −50.1 (3) | C18—C13—C17—C20 | −64.1 (4) |
C1—C8—C9—C10 | 69.9 (3) | O17—C17—C20—C21 | −175.3 (4) |
C14—C8—C9—C10 | −173.3 (3) | C13—C17—C20—C21 | −2.1 (6) |
C30—C8—C9—C11 | 72.4 (3) | O17—C17—C20—C22 | 0.8 (5) |
C1—C8—C9—C11 | −167.6 (3) | C13—C17—C20—C22 | 174.0 (3) |
C14—C8—C9—C11 | −50.7 (3) | C22—C20—C21—O21 | −1.0 (5) |
C11—C9—C10—O10 | −157.8 (3) | C17—C20—C21—O21 | 175.6 (3) |
C8—C9—C10—O10 | −33.8 (4) | C21—C20—C22—C23 | 0.7 (5) |
C11—C9—C10—C19 | 76.4 (4) | C17—C20—C22—C23 | −176.3 (3) |
C8—C9—C10—C19 | −159.5 (4) | C20—C22—C23—O21 | −0.2 (5) |
C10—C9—C11—C12 | 175.7 (3) | O7—C5—O4—C4 | −170.5 (4) |
C8—C9—C11—C12 | 50.5 (4) | C29—C4—O4—C5 | 84.8 (4) |
C9—C11—C12—C13 | −53.9 (4) | C28—C4—O4—C5 | −157.5 (4) |
C11—C12—C13—C14 | 54.7 (3) | C16—C15—O14—C14 | 120.6 (3) |
C11—C12—C13—C18 | 177.9 (3) | C14—C15—O14—C14 | 0.0 |
C11—C12—C13—C17 | −69.9 (3) | C15—C14—O14—C15 | 0.0 |
C12—C13—C14—O14 | 158.1 (3) | C13—C14—O14—C15 | −109.6 (3) |
C18—C13—C14—O14 | 39.0 (4) | C8—C14—O14—C15 | 108.0 (3) |
C17—C13—C14—O14 | −80.3 (3) | O16—C16—O16'—C31 | 0.6 (6) |
C12—C13—C14—C15 | 89.8 (3) | C15—C16—O16'—C31 | −174.4 (3) |
C18—C13—C14—C15 | −29.3 (4) | C20—C21—O21—C23 | 0.9 (5) |
C17—C13—C14—C15 | −148.6 (3) | C22—C23—O21—C21 | −0.5 (5) |
C12—C13—C14—C8 | −59.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—HO10···O16i | 0.82 | 2.25 | 2.933 (4) | 141 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
(D) methyl
6'-furanoyl-3-hydroxy-4,4,3',6',7a'-pentamethylperhydro-4
H-furo[2,1-
c]-
pyran-2-spiro-1'-perhydroisobenzofuran-7'-spiro-2''-oxirane-3''-carboxylate
top
Crystal data top
C27H34O10 | F(000) = 552 |
Mr = 518.54 | Dx = 1.350 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
a = 10.148 (5) Å | Cell parameters from 25 reflections |
b = 11.225 (7) Å | θ = 15.2–21.0° |
c = 11.356 (8) Å | µ = 0.86 mm−1 |
β = 99.44 (2)° | T = 293 K |
V = 1276.1 (14) Å3 | Prism, colourless |
Z = 2 | 0.35 × 0.35 × 0.20 mm |
Data collection top
Nonius CAD4 diffractometer | Rint = 0.061 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 4.4° |
Graphite monochromator | h = −11→11 |
θ/2θ scans | k = 0→13 |
3411 measured reflections | l = 0→13 |
2389 independent reflections | 3 standard reflections every 120 min |
2368 reflections with I > 2σ(I) | intensity decay: 2% |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.09 | Calculated w = 1/[σ2(Fo2) + (0.1223P)2 + 0.1273P] where P = (Fo2 + 2Fc2)/3 |
2385 reflections | (Δ/σ)max = −0.023 |
334 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.40 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 on F2 for ALL reflections except for 4 with very negative
F2 or flagged by the user for potential systematic errors. Weighted
R-factors wR and all goodnesses of fit S are based on
F2, conventional R-factors R are based on F,
with F set to zero for negative F2. The observed criterion of
F2 > σ(F2) is used only for calculating _R_factor_obs
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 | 0.3417 (3) | 0.3796 (4) | 0.8838 (2) | 0.0413 (6) | |
C2 | 0.2893 (3) | 0.3384 (4) | 0.9969 (2) | 0.0435 (6) | |
H2 | 0.3609 | 0.3015 | 1.0535 | 0.052* | |
C3 | 0.2482 (3) | 0.4577 (4) | 1.0446 (3) | 0.0478 (7) | |
H3 | 0.3296 | 0.4960 | 1.0861 | 0.057* | |
C4 | 0.1472 (3) | 0.4560 (5) | 1.1306 (3) | 0.0557 (8) | |
C5 | −0.0262 (3) | 0.4443 (6) | 0.9550 (4) | 0.0698 (11) | |
C6 | 0.0488 (4) | 0.5422 (6) | 0.9025 (4) | 0.0761 (13) | |
H6A | 0.0236 | 0.6183 | 0.9326 | 0.091* | |
H6B | 0.0218 | 0.5426 | 0.8165 | 0.091* | |
C7 | 0.2003 (4) | 0.5298 (4) | 0.9308 (3) | 0.0552 (8) | |
H7 | 0.2415 | 0.6090 | 0.9380 | 0.066* | |
C8 | 0.3746 (3) | 0.2872 (4) | 0.7896 (2) | 0.0400 (6) | |
C9 | 0.4618 (3) | 0.3705 (4) | 0.7256 (3) | 0.0450 (7) | |
H9 | 0.4027 | 0.4321 | 0.6849 | 0.054* | |
C10 | 0.5506 (3) | 0.4301 (4) | 0.8297 (3) | 0.0496 (7) | |
H10 | 0.6263 | 0.3776 | 0.8582 | 0.060* | |
C11 | 0.5254 (4) | 0.3063 (4) | 0.6305 (3) | 0.0531 (8) | |
H11A | 0.5739 | 0.3629 | 0.5893 | 0.064* | |
H11B | 0.5880 | 0.2468 | 0.6678 | 0.064* | |
C12 | 0.4170 (4) | 0.2472 (4) | 0.5423 (3) | 0.0550 (8) | |
H12A | 0.4587 | 0.2042 | 0.4842 | 0.066* | |
H12B | 0.3612 | 0.3087 | 0.4999 | 0.066* | |
C13 | 0.3263 (3) | 0.1594 (4) | 0.5987 (3) | 0.0468 (7) | |
C14 | 0.2683 (3) | 0.2296 (4) | 0.6958 (2) | 0.0406 (6) | |
C15 | 0.1306 (3) | 0.2815 (4) | 0.6744 (3) | 0.0486 (7) | |
H15 | 0.1221 | 0.3519 | 0.7235 | 0.058* | |
C16 | 0.0269 (4) | 0.2765 (5) | 0.5647 (3) | 0.0589 (9) | |
C17 | 0.4072 (3) | 0.0464 (4) | 0.6414 (3) | 0.0482 (7) | |
C18 | 0.2206 (4) | 0.1108 (5) | 0.4972 (3) | 0.0618 (9) | |
H18A | 0.1637 | 0.1747 | 0.4635 | 0.093* | |
H18B | 0.1679 | 0.0512 | 0.5283 | 0.093* | |
H18C | 0.2642 | 0.0763 | 0.4365 | 0.093* | |
C19 | 0.6028 (5) | 0.5517 (5) | 0.8063 (5) | 0.0731 (11) | |
H19A | 0.6574 | 0.5809 | 0.8775 | 0.110* | |
H19B | 0.5291 | 0.6050 | 0.7831 | 0.110* | |
H19C | 0.6552 | 0.5467 | 0.7433 | 0.110* | |
C20 | 0.3526 (3) | −0.0513 (4) | 0.7058 (3) | 0.0492 (7) | |
C21 | 0.2329 (5) | −0.0688 (5) | 0.7469 (6) | 0.088 (2) | |
H21 | 0.1626 | −0.0147 | 0.7398 | 0.105* | |
C22 | 0.4252 (4) | −0.1539 (5) | 0.7385 (4) | 0.0608 (9) | |
H22 | 0.5097 | −0.1706 | 0.7211 | 0.073* | |
C23 | 0.3551 (4) | −0.2249 (5) | 0.7990 (4) | 0.0655 (10) | |
H23 | 0.3848 | −0.2964 | 0.8354 | 0.079* | |
C28 | 0.1360 (5) | 0.5813 (6) | 1.1824 (5) | 0.0831 (15) | |
H28A | 0.1145 | 0.6374 | 1.1184 | 0.125* | |
H28B | 0.2195 | 0.6028 | 1.2303 | 0.125* | |
H28C | 0.0669 | 0.5818 | 1.2309 | 0.125* | |
C29 | 0.1811 (4) | 0.3630 (7) | 1.2279 (3) | 0.0768 (13) | |
H29A | 0.1154 | 0.3649 | 1.2798 | 0.115* | |
H29B | 0.2676 | 0.3797 | 1.2732 | 0.115* | |
H29C | 0.1818 | 0.2854 | 1.1923 | 0.115* | |
C30 | 0.4587 (3) | 0.1895 (4) | 0.8634 (3) | 0.0440 (6) | |
H30A | 0.5252 | 0.2262 | 0.9221 | 0.066* | |
H30B | 0.5016 | 0.1410 | 0.8112 | 0.066* | |
H30C | 0.4013 | 0.1407 | 0.9026 | 0.066* | |
C31 | −0.1611 (6) | 0.1723 (9) | 0.4668 (5) | 0.108 (2) | |
H31A | −0.2122 | 0.1023 | 0.4773 | 0.162* | |
H31B | −0.1251 | 0.1657 | 0.3939 | 0.162* | |
H31C | −0.2177 | 0.2412 | 0.4630 | 0.162* | |
O1 | 0.2442 (2) | 0.4654 (3) | 0.8336 (2) | 0.0480 (5) | |
O2 | 0.1793 (2) | 0.2612 (4) | 0.9714 (2) | 0.0530 (6) | |
HO2 | 0.1650 | 0.2465 | 0.8997 | 0.051* | |
O4 | 0.0151 (2) | 0.4182 (4) | 1.0686 (2) | 0.0618 (7) | |
O7 | −0.1231 (4) | 0.3961 (7) | 0.9026 (4) | 0.110 (2) | |
O10 | 0.4660 (2) | 0.4386 (4) | 0.9212 (2) | 0.0546 (6) | |
O14 | 0.1587 (2) | 0.1745 (3) | 0.7438 (2) | 0.0473 (5) | |
O16 | 0.0167 (4) | 0.3540 (4) | 0.4901 (3) | 0.0815 (9) | |
O16' | −0.0534 (3) | 0.1840 (5) | 0.5658 (2) | 0.0725 (8) | |
O17 | 0.5166 (3) | 0.0316 (4) | 0.6119 (3) | 0.0641 (7) | |
O21 | 0.2348 (4) | −0.1762 (5) | 0.7988 (5) | 0.111 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0345 (13) | 0.0444 (14) | 0.0479 (13) | 0.0017 (11) | 0.0149 (10) | 0.0026 (12) |
C2 | 0.0396 (14) | 0.052 (2) | 0.0413 (12) | 0.0005 (12) | 0.0128 (10) | 0.0000 (12) |
C3 | 0.0373 (13) | 0.057 (2) | 0.0533 (15) | −0.0058 (12) | 0.0185 (11) | −0.0083 (13) |
C4 | 0.041 (2) | 0.076 (2) | 0.054 (2) | −0.0005 (15) | 0.0198 (13) | −0.012 (2) |
C5 | 0.035 (2) | 0.094 (3) | 0.081 (2) | 0.013 (2) | 0.0119 (15) | −0.009 (2) |
C6 | 0.070 (2) | 0.086 (3) | 0.078 (2) | 0.038 (2) | 0.029 (2) | 0.018 (2) |
C7 | 0.057 (2) | 0.048 (2) | 0.067 (2) | 0.006 (2) | 0.0290 (15) | 0.000 (2) |
C8 | 0.0356 (12) | 0.0457 (15) | 0.0420 (13) | 0.0035 (11) | 0.0161 (10) | 0.0044 (12) |
C9 | 0.0433 (14) | 0.0437 (15) | 0.0539 (15) | 0.0038 (12) | 0.0254 (12) | 0.0089 (13) |
C10 | 0.0429 (15) | 0.045 (2) | 0.067 (2) | −0.0009 (13) | 0.0278 (13) | 0.0007 (14) |
C11 | 0.055 (2) | 0.051 (2) | 0.063 (2) | 0.0017 (15) | 0.0357 (14) | 0.0058 (15) |
C12 | 0.069 (2) | 0.056 (2) | 0.0468 (15) | 0.006 (2) | 0.0306 (14) | 0.0086 (14) |
C13 | 0.049 (2) | 0.052 (2) | 0.0423 (13) | 0.0041 (14) | 0.0177 (11) | 0.0023 (13) |
C14 | 0.0423 (14) | 0.0441 (14) | 0.0385 (12) | 0.0009 (11) | 0.0160 (10) | 0.0062 (11) |
C15 | 0.0419 (14) | 0.057 (2) | 0.0481 (14) | 0.0055 (13) | 0.0114 (11) | 0.0031 (14) |
C16 | 0.049 (2) | 0.074 (2) | 0.054 (2) | 0.009 (2) | 0.0080 (13) | 0.005 (2) |
C17 | 0.049 (2) | 0.047 (2) | 0.0524 (15) | 0.0009 (13) | 0.0181 (12) | −0.0024 (13) |
C18 | 0.064 (2) | 0.072 (2) | 0.050 (2) | 0.007 (2) | 0.0117 (14) | −0.008 (2) |
C19 | 0.082 (3) | 0.050 (2) | 0.098 (3) | −0.014 (2) | 0.045 (2) | −0.004 (2) |
C20 | 0.0431 (14) | 0.046 (2) | 0.060 (2) | −0.0001 (13) | 0.0148 (12) | −0.0014 (14) |
C21 | 0.062 (2) | 0.053 (2) | 0.157 (5) | 0.003 (2) | 0.045 (3) | 0.031 (3) |
C22 | 0.050 (2) | 0.063 (2) | 0.070 (2) | 0.002 (2) | 0.0126 (15) | 0.014 (2) |
C23 | 0.049 (2) | 0.055 (2) | 0.097 (3) | 0.009 (2) | 0.024 (2) | 0.029 (2) |
C28 | 0.068 (2) | 0.102 (4) | 0.087 (3) | 0.001 (3) | 0.033 (2) | −0.043 (3) |
C29 | 0.069 (2) | 0.115 (4) | 0.054 (2) | 0.015 (3) | 0.030 (2) | 0.011 (2) |
C30 | 0.0415 (13) | 0.0461 (15) | 0.0461 (13) | 0.0050 (13) | 0.0120 (10) | 0.0049 (13) |
C31 | 0.080 (3) | 0.137 (6) | 0.093 (3) | −0.013 (4) | −0.028 (3) | −0.003 (4) |
O1 | 0.0500 (11) | 0.0454 (12) | 0.0527 (11) | 0.0071 (9) | 0.0203 (9) | 0.0047 (9) |
O2 | 0.0571 (13) | 0.0585 (13) | 0.0489 (11) | −0.0117 (11) | 0.0254 (9) | −0.0020 (10) |
O4 | 0.0390 (11) | 0.082 (2) | 0.0696 (14) | −0.0042 (12) | 0.0225 (10) | −0.0036 (13) |
O7 | 0.055 (2) | 0.163 (5) | 0.106 (2) | −0.002 (2) | −0.005 (2) | −0.023 (3) |
O10 | 0.0418 (11) | 0.0639 (14) | 0.0635 (13) | −0.0094 (11) | 0.0245 (9) | −0.0145 (11) |
O14 | 0.0415 (10) | 0.0606 (13) | 0.0420 (9) | −0.0036 (9) | 0.0140 (8) | 0.0074 (10) |
O16 | 0.081 (2) | 0.083 (2) | 0.075 (2) | 0.011 (2) | −0.0023 (15) | 0.022 (2) |
O16' | 0.0589 (14) | 0.094 (2) | 0.0613 (14) | −0.010 (2) | 0.0002 (11) | 0.007 (2) |
O17 | 0.0602 (14) | 0.0558 (14) | 0.086 (2) | 0.0083 (12) | 0.0417 (13) | 0.0019 (13) |
O21 | 0.090 (2) | 0.084 (3) | 0.175 (4) | 0.013 (2) | 0.069 (3) | 0.047 (3) |
Geometric parameters (Å, º) top
C1—O10 | 1.426 (4) | C10—O10 | 1.456 (3) |
C1—O1 | 1.430 (4) | C10—C19 | 1.502 (5) |
C1—C2 | 1.540 (4) | C11—C12 | 1.514 (6) |
C1—C8 | 1.565 (4) | C12—C13 | 1.556 (5) |
C2—O2 | 1.405 (4) | C13—C18 | 1.540 (5) |
C2—C3 | 1.528 (5) | C13—C17 | 1.546 (5) |
C3—C4 | 1.528 (4) | C13—C14 | 1.548 (4) |
C3—C7 | 1.535 (5) | C14—O14 | 1.455 (3) |
C4—O4 | 1.471 (4) | C14—C15 | 1.496 (4) |
C4—C29 | 1.518 (6) | C15—O14 | 1.439 (4) |
C4—C28 | 1.535 (7) | C15—C16 | 1.494 (5) |
C5—O7 | 1.193 (6) | C16—O16 | 1.207 (5) |
C5—O4 | 1.322 (5) | C16—O16' | 1.322 (6) |
C5—C6 | 1.514 (8) | C17—O17 | 1.223 (4) |
C6—C7 | 1.524 (6) | C17—C20 | 1.475 (5) |
C7—O1 | 1.449 (4) | C20—C22 | 1.385 (6) |
C8—C14 | 1.530 (4) | C20—C21 | 1.385 (6) |
C8—C9 | 1.548 (4) | C21—O21 | 1.341 (7) |
C8—C30 | 1.549 (4) | C22—C23 | 1.332 (6) |
C9—C10 | 1.519 (5) | C23—O21 | 1.337 (6) |
C9—C11 | 1.526 (4) | C31—O16' | 1.440 (5) |
| | | |
O10—C1—O1 | 109.0 (3) | C19—C10—C9 | 116.3 (3) |
O10—C1—C2 | 107.5 (2) | C12—C11—C9 | 109.3 (3) |
O1—C1—C2 | 102.9 (2) | C11—C12—C13 | 114.9 (3) |
O10—C1—C8 | 103.5 (2) | C18—C13—C17 | 102.3 (3) |
O1—C1—C8 | 112.6 (2) | C18—C13—C14 | 114.4 (3) |
C2—C1—C8 | 120.9 (3) | C17—C13—C14 | 116.0 (2) |
O2—C2—C3 | 111.1 (2) | C18—C13—C12 | 107.7 (3) |
O2—C2—C1 | 112.7 (2) | C17—C13—C12 | 109.2 (3) |
C3—C2—C1 | 100.6 (3) | C14—C13—C12 | 106.9 (3) |
C2—C3—C4 | 117.8 (3) | O14—C14—C15 | 58.4 (2) |
C2—C3—C7 | 103.3 (2) | O14—C14—C8 | 114.4 (2) |
C4—C3—C7 | 113.1 (3) | C15—C14—C8 | 118.8 (3) |
O4—C4—C29 | 103.3 (3) | O14—C14—C13 | 117.0 (3) |
O4—C4—C3 | 110.6 (3) | C15—C14—C13 | 122.4 (3) |
C29—C4—C3 | 112.2 (3) | C8—C14—C13 | 113.8 (2) |
O4—C4—C28 | 109.2 (3) | O14—C15—C16 | 118.3 (3) |
C29—C4—C28 | 111.9 (4) | O14—C15—C14 | 59.4 (2) |
C3—C4—C28 | 109.5 (3) | C16—C15—C14 | 129.2 (3) |
O7—C5—O4 | 119.4 (5) | O16—C16—O16' | 126.2 (4) |
O7—C5—C6 | 124.0 (5) | O16—C16—C15 | 121.7 (4) |
O4—C5—C6 | 116.4 (4) | O16'—C16—C15 | 111.9 (3) |
C5—C6—C7 | 113.9 (3) | O17—C17—C20 | 117.8 (3) |
O1—C7—C6 | 108.1 (3) | O17—C17—C13 | 119.0 (3) |
O1—C7—C3 | 106.5 (3) | C20—C17—C13 | 122.9 (3) |
C6—C7—C3 | 113.3 (3) | C22—C20—C21 | 104.4 (3) |
C14—C8—C9 | 108.7 (2) | C22—C20—C17 | 121.7 (3) |
C14—C8—C30 | 109.9 (3) | C21—C20—C17 | 133.9 (4) |
C9—C8—C30 | 112.1 (2) | O21—C21—C20 | 108.9 (4) |
C14—C8—C1 | 123.4 (2) | C23—C22—C20 | 109.3 (3) |
C9—C8—C1 | 97.1 (2) | C22—C23—O21 | 108.6 (4) |
C30—C8—C1 | 105.1 (2) | C1—O1—C7 | 108.2 (2) |
C10—C9—C11 | 119.5 (3) | C5—O4—C4 | 121.4 (3) |
C10—C9—C8 | 102.3 (2) | C1—O10—C10 | 110.7 (2) |
C11—C9—C8 | 112.8 (3) | C15—O14—C14 | 62.3 (2) |
O10—C10—C19 | 109.4 (3) | C16—O16'—C31 | 117.0 (4) |
O10—C10—C9 | 103.9 (2) | C23—O21—C21 | 108.5 (4) |
| | | |
O10—C1—C2—O2 | −169.6 (3) | C30—C8—C14—O14 | 72.5 (3) |
O1—C1—C2—O2 | 75.4 (3) | C1—C8—C14—O14 | −52.3 (4) |
C8—C1—C2—O2 | −51.3 (3) | C9—C8—C14—C15 | −98.6 (3) |
O10—C1—C2—C3 | 72.0 (3) | C30—C8—C14—C15 | 138.4 (3) |
O1—C1—C2—C3 | −43.0 (3) | C1—C8—C14—C15 | 13.7 (4) |
C8—C1—C2—C3 | −169.6 (2) | C9—C8—C14—C13 | 57.2 (3) |
O2—C2—C3—C4 | 39.4 (4) | C30—C8—C14—C13 | −65.8 (3) |
C1—C2—C3—C4 | 158.9 (3) | C1—C8—C14—C13 | 169.5 (2) |
O2—C2—C3—C7 | −86.0 (3) | C18—C13—C14—O14 | 48.3 (4) |
C1—C2—C3—C7 | 33.4 (3) | C17—C13—C14—O14 | −70.5 (3) |
C2—C3—C4—O4 | −68.3 (4) | C12—C13—C14—O14 | 167.4 (2) |
C2—C3—C4—C29 | 46.5 (4) | C18—C13—C14—C15 | −19.8 (4) |
C7—C3—C4—C29 | 167.0 (4) | C17—C13—C14—C15 | −138.6 (3) |
C2—C3—C4—C28 | 171.4 (3) | C12—C13—C14—C15 | 99.3 (3) |
C7—C3—C4—C28 | −68.1 (4) | C18—C13—C14—C8 | −174.6 (3) |
O7—C5—C6—C7 | −137.4 (5) | C17—C13—C14—C8 | 66.6 (3) |
C5—C6—C7—O1 | 93.2 (4) | C12—C13—C14—C8 | −55.5 (3) |
C2—C3—C7—O1 | −13.2 (3) | O14—C14—C15—O14 | 0.000 (1) |
C3—C7—O1—C1 | −14.6 (3) | C8—C14—C15—O14 | −102.5 (3) |
C7—O1—C1—C2 | 36.3 (3) | C13—C14—C15—O14 | 103.9 (3) |
C4—C3—C7—C6 | −23.0 (5) | O14—C14—C15—C16 | −103.2 (4) |
C3—C7—C6—C5 | −24.5 (5) | C8—C14—C15—C16 | 154.3 (3) |
C7—C6—C5—O4 | 47.5 (5) | O14—C15—C16—O16 | −165.0 (4) |
C6—C5—O4—C4 | −17.0 (6) | O14—C15—C16—O16' | 19.3 (4) |
C5—O4—C4—C3 | −32.7 (5) | C14—C15—C16—O16' | 91.4 (4) |
O4—C4—C3—C7 | 52.3 (4) | C18—C13—C17—O17 | 103.3 (3) |
O10—C1—C8—C9 | −42.2 (3) | C14—C13—C17—O17 | −131.5 (3) |
C1—C8—C9—C10 | 45.1 (3) | C12—C13—C17—O17 | −10.6 (4) |
C8—C9—C10—O10 | −32.9 (3) | C18—C13—C17—C20 | −70.0 (4) |
C9—C10—O10—C1 | 5.5 (3) | C14—C13—C17—C20 | 55.3 (4) |
C10—O10—C1—C8 | 23.9 (3) | C12—C13—C17—C20 | 176.1 (3) |
C13—C14—C15—C16 | 0.7 (5) | O17—C17—C20—C22 | 3.9 (5) |
C14—C15—C16—O16 | −92.8 (5) | C13—C17—C20—C22 | 177.2 (3) |
C4—C3—C7—O1 | −141.7 (3) | O17—C17—C20—C21 | −176.3 (5) |
C2—C3—C7—C6 | 105.5 (3) | C13—C17—C20—C21 | −3.0 (7) |
O10—C1—C8—C14 | −160.1 (3) | C22—C20—C21—O21 | −1.0 (7) |
O1—C1—C8—C14 | −42.5 (3) | C17—C20—C21—O21 | 179.1 (5) |
C2—C1—C8—C14 | 79.6 (3) | C21—C20—C22—C23 | −2.2 (6) |
O1—C1—C8—C9 | 75.5 (3) | C17—C20—C22—C23 | 177.6 (4) |
C2—C1—C8—C9 | −162.4 (2) | C20—C22—C23—O21 | 4.7 (6) |
O10—C1—C8—C30 | 73.0 (3) | O10—C1—O1—C7 | −77.6 (3) |
O1—C1—C8—C30 | −169.3 (2) | C8—C1—O1—C7 | 168.1 (2) |
C2—C1—C8—C30 | −47.3 (3) | C6—C7—O1—C1 | −136.6 (3) |
C14—C8—C9—C10 | 174.0 (2) | O7—C5—O4—C4 | 167.7 (5) |
C30—C8—C9—C10 | −64.3 (3) | C29—C4—O4—C5 | −153.0 (4) |
C14—C8—C9—C11 | −56.3 (3) | C28—C4—O4—C5 | 87.8 (4) |
C30—C8—C9—C11 | 65.4 (3) | O1—C1—O10—C10 | −96.2 (3) |
C1—C8—C9—C11 | 174.8 (3) | C2—C1—O10—C10 | 152.9 (3) |
C11—C9—C10—O10 | −158.3 (3) | C19—C10—O10—C1 | 130.4 (3) |
C11—C9—C10—C19 | 81.4 (4) | C16—C15—O14—C14 | 121.1 (3) |
C8—C9—C10—C19 | −153.3 (3) | C14—C15—O14—C14 | 0.000 (1) |
C10—C9—C11—C12 | 175.8 (3) | C15—C14—O14—C15 | 0.000 (1) |
C8—C9—C11—C12 | 55.6 (4) | C8—C14—O14—C15 | 110.0 (3) |
C9—C11—C12—C13 | −56.1 (4) | C13—C14—O14—C15 | −113.2 (3) |
C11—C12—C13—C18 | 178.5 (3) | O16—C16—O16'—C31 | 2.0 (7) |
C11—C12—C13—C17 | −71.1 (4) | C15—C16—O16'—C31 | 177.6 (5) |
C11—C12—C13—C14 | 55.1 (4) | C22—C23—O21—C21 | −5.4 (7) |
C9—C8—C14—O14 | −164.6 (2) | C20—C21—O21—C23 | 3.9 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—HO2···O14 | 0.82 | 1.94 | 2.738 (3) | 165 |
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