The X-ray structure of dimethyl (
Z)-[(8a
S,2
R,4a
R,4b
R)-8a-methoxycarbonyl-1,4a,7-trimethyl-8-oxo-2,3,4,4a,4b,5,8,8a,9,10-decahydrophenanthren-2-yl]-2-butenedioate, C
25H
32O
7, confirmed its relative configuration. The structure shows the bend in the molecular skeleton as found for similar compounds. Weak intermolecular C—H
O interactions have been found in the crystal.
Supporting information
CCDC reference: 170315
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.123
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
STRVAL_01
From the CIF: _refine_ls_abs_structure_Flack 0.500
From the CIF: _refine_ls_abs_structure_Flack_su 1.600
Alert C Flack test results are ambiguous.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.98
From the CIF: _reflns_number_total 4163
Count of symmetry unique reflns 2372
Completeness (_total/calc) 175.51%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1791
Fraction of Friedel pairs measured 0.755
Are heavy atom types Z>Si present no
ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: MolEN (Fair, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
dimethyl(
Z)-[(8aS,2
R, 4aR, 4bR)-8a-methoxycarbonyl-1,4a,7-
-trimethyl-8-oxo-2,3,4,4a,4 b,5,8,8a,9,10-decahydro-
-phenanthren-2-yl]-2-butenedioate
top
Crystal data top
C25H32O7 | Dx = 1.238 Mg m−3 |
Mr = 444.51 | Melting point: 430 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.810 (2) Å | Cell parameters from 25 reflections |
b = 13.985 (3) Å | θ = 10–12° |
c = 14.434 (3) Å | µ = 0.09 mm−1 |
V = 2384.0 (8) Å3 | T = 293 K |
Z = 4 | Block, colourless |
F(000) = 952 | 0.64 × 0.62 × 0.44 mm |
Data collection top
Nonius-CAD4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.2° |
Graphite monochromator | h = −14→4 |
ω–scans | k = −16→16 |
6144 measured reflections | l = 0→17 |
4163 independent reflections | 3 standard reflections every 250 reflections |
3049 reflections with I > 2σ(I) | intensity decay: 1.8% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.6085P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.123 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.15 e Å−3 |
4163 reflections | Δρmin = −0.14 e Å−3 |
290 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0069 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: (Flack, 1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.5 (16) |
Special details top
Experimental. crystal source: slow evaporation of a methanol solution |
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. Absolute structure could not be determined. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1392 (3) | 0.0672 (2) | 1.05093 (19) | 0.0489 (8) | |
H1A | 0.2109 | 0.0338 | 1.0461 | 0.059* | |
H1B | 0.1532 | 0.1345 | 1.0397 | 0.059* | |
C2 | 0.0924 (3) | 0.0547 (3) | 1.1484 (2) | 0.0566 (9) | |
H2A | 0.1481 | 0.0759 | 1.1934 | 0.068* | |
H2B | 0.0765 | −0.0123 | 1.1598 | 0.068* | |
C3 | −0.0159 (3) | 0.1131 (2) | 1.1591 (2) | 0.0538 (8) | |
H3 | −0.0528 | 0.0914 | 1.2162 | 0.065* | |
C4 | −0.0973 (3) | 0.0943 (2) | 1.0808 (2) | 0.0508 (8) | |
C5 | −0.0649 (3) | 0.0539 (2) | 1.0013 (2) | 0.0461 (8) | |
C6 | −0.1476 (3) | 0.0318 (2) | 0.9250 (2) | 0.0504 (8) | |
H6A | −0.2229 | 0.0511 | 0.9442 | 0.061* | |
H6B | −0.1489 | −0.0367 | 0.9144 | 0.061* | |
C7 | −0.1176 (2) | 0.0824 (2) | 0.8348 (2) | 0.0470 (8) | |
H7A | −0.1252 | 0.1508 | 0.8435 | 0.056* | |
H7B | −0.1706 | 0.0631 | 0.7871 | 0.056* | |
C8 | 0.0028 (2) | 0.0601 (2) | 0.80256 (18) | 0.0414 (7) | |
C9 | 0.0862 (2) | 0.0800 (2) | 0.88366 (19) | 0.0407 (7) | |
H9 | 0.0755 | 0.1480 | 0.8973 | 0.049* | |
C10 | 0.0581 (3) | 0.0290 (2) | 0.97680 (19) | 0.0436 (7) | |
C11 | 0.2096 (3) | 0.0729 (2) | 0.8537 (2) | 0.0497 (8) | |
H11A | 0.2575 | 0.0979 | 0.9026 | 0.060* | |
H11B | 0.2291 | 0.0063 | 0.8444 | 0.060* | |
C12 | 0.2316 (3) | 0.1270 (2) | 0.7665 (2) | 0.0506 (8) | |
H12 | 0.3064 | 0.1424 | 0.7530 | 0.061* | |
C13 | 0.1529 (3) | 0.1547 (2) | 0.7068 (2) | 0.0479 (8) | |
C14 | 0.0340 (3) | 0.1256 (2) | 0.7200 (2) | 0.0467 (8) | |
C15 | 0.0095 (3) | 0.2193 (2) | 1.17131 (19) | 0.0496 (8) | |
C16 | 0.0009 (3) | 0.2845 (2) | 1.1048 (2) | 0.0546 (8) | |
H16 | −0.0189 | 0.2639 | 1.0457 | 0.066* | |
C17 | 0.0209 (3) | 0.3866 (3) | 1.1190 (2) | 0.0582 (9) | |
C18 | 0.0267 (5) | 0.5370 (3) | 1.0456 (3) | 0.1009 (16) | |
H18A | −0.0402 | 0.5643 | 1.0725 | 0.121* | |
H18B | 0.0379 | 0.5631 | 0.9847 | 0.121* | |
H18C | 0.0910 | 0.5517 | 1.0837 | 0.121* | |
C19 | 0.0418 (3) | 0.2478 (2) | 1.2682 (2) | 0.0514 (8) | |
C20 | 0.1881 (4) | 0.2968 (4) | 1.3663 (3) | 0.0950 (15) | |
H20A | 0.1565 | 0.3590 | 1.3771 | 0.114* | |
H20B | 0.2693 | 0.3007 | 1.3678 | 0.114* | |
H20C | 0.1626 | 0.2535 | 1.4135 | 0.114* | |
C21 | −0.2177 (3) | 0.1226 (3) | 1.1025 (3) | 0.0776 (12) | |
H21A | −0.2519 | 0.1503 | 1.0484 | 0.093* | |
H21B | −0.2180 | 0.1686 | 1.1519 | 0.093* | |
H21C | −0.2599 | 0.0671 | 1.1210 | 0.093* | |
C22 | 0.0040 (3) | −0.0412 (2) | 0.7622 (2) | 0.0486 (7) | |
C23 | 0.1085 (3) | −0.1566 (2) | 0.6815 (3) | 0.0732 (11) | |
H23A | 0.1019 | −0.2054 | 0.7279 | 0.088* | |
H23B | 0.1794 | −0.1634 | 0.6497 | 0.088* | |
H23C | 0.0474 | −0.1626 | 0.6380 | 0.088* | |
C24 | 0.0727 (3) | −0.0805 (2) | 0.9710 (2) | 0.0562 (9) | |
H24A | 0.0598 | −0.1082 | 1.0309 | 0.067* | |
H24B | 0.1481 | −0.0953 | 0.9508 | 0.067* | |
H24C | 0.0191 | −0.1062 | 0.9276 | 0.067* | |
C25 | 0.1791 (3) | 0.2122 (3) | 0.6216 (2) | 0.0693 (11) | |
H25A | 0.1440 | 0.2739 | 0.6264 | 0.083* | |
H25B | 0.1505 | 0.1795 | 0.5680 | 0.083* | |
H25C | 0.2596 | 0.2198 | 0.6160 | 0.083* | |
O1 | 0.0376 (3) | 0.42510 (18) | 1.19113 (17) | 0.0860 (9) | |
O2 | 0.0137 (3) | 0.43439 (18) | 1.03911 (15) | 0.0787 (8) | |
O3 | −0.0243 (2) | 0.2513 (2) | 1.33007 (16) | 0.0729 (7) | |
O4 | 0.1522 (2) | 0.26248 (19) | 1.27701 (16) | 0.0682 (7) | |
O5 | −0.0754 (2) | −0.09320 (18) | 0.75892 (19) | 0.0779 (8) | |
O6 | 0.10348 (19) | −0.06377 (15) | 0.72505 (17) | 0.0628 (6) | |
O7 | −0.0391 (2) | 0.14819 (18) | 0.66556 (15) | 0.0675 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0502 (18) | 0.0511 (18) | 0.0454 (18) | 0.0033 (16) | −0.0013 (14) | −0.0009 (15) |
C2 | 0.071 (2) | 0.0552 (19) | 0.0433 (17) | 0.0044 (18) | −0.0040 (17) | 0.0019 (15) |
C3 | 0.067 (2) | 0.0583 (19) | 0.0364 (15) | 0.0005 (17) | 0.0094 (17) | 0.0065 (14) |
C4 | 0.0510 (19) | 0.0519 (19) | 0.0495 (18) | −0.0072 (16) | 0.0025 (16) | 0.0015 (15) |
C5 | 0.0472 (18) | 0.0436 (17) | 0.0475 (17) | −0.0021 (15) | 0.0043 (15) | 0.0084 (14) |
C6 | 0.0387 (18) | 0.0568 (19) | 0.0558 (19) | −0.0030 (15) | 0.0027 (16) | −0.0031 (16) |
C7 | 0.0419 (17) | 0.0483 (18) | 0.0509 (18) | 0.0001 (15) | −0.0029 (15) | 0.0019 (15) |
C8 | 0.0417 (16) | 0.0386 (15) | 0.0438 (15) | 0.0016 (14) | −0.0025 (14) | 0.0013 (12) |
C9 | 0.0387 (16) | 0.0401 (16) | 0.0435 (15) | −0.0023 (13) | 0.0019 (14) | −0.0027 (13) |
C10 | 0.0452 (18) | 0.0447 (16) | 0.0410 (16) | 0.0015 (15) | 0.0000 (14) | 0.0027 (14) |
C11 | 0.0420 (18) | 0.059 (2) | 0.0480 (17) | 0.0023 (16) | −0.0025 (14) | −0.0041 (16) |
C12 | 0.0464 (18) | 0.0515 (18) | 0.0540 (18) | −0.0031 (15) | 0.0085 (16) | −0.0083 (16) |
C13 | 0.056 (2) | 0.0437 (17) | 0.0445 (17) | 0.0006 (15) | 0.0048 (16) | −0.0004 (15) |
C14 | 0.054 (2) | 0.0469 (17) | 0.0393 (16) | 0.0064 (15) | 0.0036 (16) | −0.0023 (14) |
C15 | 0.055 (2) | 0.0556 (18) | 0.0378 (15) | 0.0013 (17) | 0.0058 (16) | −0.0025 (14) |
C16 | 0.068 (2) | 0.0574 (19) | 0.0384 (15) | 0.0030 (19) | 0.0033 (17) | −0.0025 (15) |
C17 | 0.067 (2) | 0.062 (2) | 0.0457 (18) | 0.0076 (18) | 0.0080 (18) | 0.0052 (16) |
C18 | 0.145 (5) | 0.057 (3) | 0.101 (3) | 0.012 (3) | 0.005 (3) | 0.021 (2) |
C19 | 0.057 (2) | 0.0560 (19) | 0.0414 (17) | 0.0039 (16) | 0.0028 (17) | 0.0006 (15) |
C20 | 0.079 (3) | 0.146 (4) | 0.060 (2) | −0.021 (3) | −0.012 (2) | −0.009 (3) |
C21 | 0.058 (2) | 0.100 (3) | 0.075 (3) | −0.001 (2) | 0.017 (2) | −0.023 (2) |
C22 | 0.0527 (19) | 0.0460 (17) | 0.0471 (17) | −0.0038 (16) | −0.0068 (17) | −0.0006 (14) |
C23 | 0.080 (3) | 0.047 (2) | 0.093 (3) | 0.0064 (19) | 0.014 (2) | −0.019 (2) |
C24 | 0.068 (2) | 0.0452 (18) | 0.0551 (18) | 0.0052 (17) | 0.0004 (18) | 0.0044 (15) |
C25 | 0.081 (3) | 0.068 (2) | 0.059 (2) | −0.001 (2) | 0.015 (2) | 0.0085 (19) |
O1 | 0.143 (3) | 0.0613 (15) | 0.0538 (14) | −0.0039 (17) | −0.0062 (16) | −0.0079 (13) |
O2 | 0.118 (2) | 0.0643 (16) | 0.0541 (13) | 0.0058 (16) | 0.0000 (16) | 0.0117 (12) |
O3 | 0.0622 (16) | 0.114 (2) | 0.0423 (12) | −0.0046 (15) | 0.0130 (13) | −0.0125 (13) |
O4 | 0.0548 (15) | 0.102 (2) | 0.0480 (13) | −0.0047 (14) | 0.0018 (12) | −0.0085 (13) |
O5 | 0.0629 (16) | 0.0735 (17) | 0.097 (2) | −0.0190 (14) | −0.0018 (15) | −0.0292 (15) |
O6 | 0.0605 (15) | 0.0421 (12) | 0.0857 (17) | −0.0020 (11) | 0.0148 (13) | −0.0144 (12) |
O7 | 0.0631 (16) | 0.0897 (18) | 0.0498 (13) | 0.0130 (14) | −0.0058 (12) | 0.0155 (13) |
Geometric parameters (Å, º) top
C1—C2 | 1.522 (4) | C13—C25 | 1.501 (4) |
C1—C10 | 1.532 (4) | C14—O7 | 1.209 (4) |
C1—H1A | 0.9700 | C15—C16 | 1.328 (4) |
C1—H1B | 0.9700 | C15—C19 | 1.504 (4) |
C2—C3 | 1.525 (5) | C16—C17 | 1.463 (5) |
C2—H2A | 0.9700 | C16—H16 | 0.9300 |
C2—H2B | 0.9700 | C17—O1 | 1.188 (4) |
C3—C4 | 1.508 (5) | C17—O2 | 1.335 (4) |
C3—C15 | 1.525 (4) | C18—O2 | 1.446 (5) |
C3—H3 | 0.9800 | C18—H18A | 0.9600 |
C4—C5 | 1.335 (4) | C18—H18B | 0.9600 |
C4—C21 | 1.509 (5) | C18—H18C | 0.9600 |
C5—C6 | 1.505 (4) | C19—O3 | 1.187 (4) |
C5—C10 | 1.535 (4) | C19—O4 | 1.326 (4) |
C6—C7 | 1.523 (4) | C20—O4 | 1.439 (4) |
C6—H6A | 0.9700 | C20—H20A | 0.9600 |
C6—H6B | 0.9700 | C20—H20B | 0.9600 |
C7—C8 | 1.528 (4) | C20—H20C | 0.9600 |
C7—H7A | 0.9700 | C21—H21A | 0.9600 |
C7—H7B | 0.9700 | C21—H21B | 0.9600 |
C8—C22 | 1.532 (4) | C21—H21C | 0.9600 |
C8—C14 | 1.547 (4) | C22—O5 | 1.188 (4) |
C8—C9 | 1.555 (4) | C22—O6 | 1.329 (4) |
C9—C11 | 1.522 (4) | C23—O6 | 1.443 (4) |
C9—C10 | 1.558 (4) | C23—H23A | 0.9600 |
C9—H9 | 0.9800 | C23—H23B | 0.9600 |
C10—C24 | 1.543 (4) | C23—H23C | 0.9600 |
C11—C12 | 1.491 (4) | C24—H24A | 0.9600 |
C11—H11A | 0.9700 | C24—H24B | 0.9600 |
C11—H11B | 0.9700 | C24—H24C | 0.9600 |
C12—C13 | 1.325 (4) | C25—H25A | 0.9600 |
C12—H12 | 0.9300 | C25—H25B | 0.9600 |
C13—C14 | 1.475 (4) | C25—H25C | 0.9600 |
| | | |
C2—C1—C10 | 112.3 (3) | C11—C12—H12 | 117.5 |
C2—C1—H1A | 109.1 | C12—C13—C14 | 120.2 (3) |
C10—C1—H1A | 109.1 | C12—C13—C25 | 123.0 (3) |
C2—C1—H1B | 109.1 | C14—C13—C25 | 116.8 (3) |
C10—C1—H1B | 109.1 | O7—C14—C13 | 121.5 (3) |
H1A—C1—H1B | 107.9 | O7—C14—C8 | 119.0 (3) |
C1—C2—C3 | 109.7 (3) | C13—C14—C8 | 119.3 (3) |
C1—C2—H2A | 109.7 | C16—C15—C19 | 120.7 (3) |
C3—C2—H2A | 109.7 | C16—C15—C3 | 124.7 (3) |
C1—C2—H2B | 109.7 | C19—C15—C3 | 114.5 (3) |
C3—C2—H2B | 109.7 | C15—C16—C17 | 123.8 (3) |
H2A—C2—H2B | 108.2 | C15—C16—H16 | 118.1 |
C4—C3—C2 | 111.4 (3) | C17—C16—H16 | 118.1 |
C4—C3—C15 | 112.5 (3) | O1—C17—O2 | 122.8 (3) |
C2—C3—C15 | 111.6 (3) | O1—C17—C16 | 126.3 (3) |
C4—C3—H3 | 107.0 | O2—C17—C16 | 110.9 (3) |
C2—C3—H3 | 107.0 | O2—C18—H18A | 109.5 |
C15—C3—H3 | 107.0 | O2—C18—H18B | 109.5 |
C5—C4—C3 | 122.3 (3) | H18A—C18—H18B | 109.5 |
C5—C4—C21 | 124.1 (3) | O2—C18—H18C | 109.5 |
C3—C4—C21 | 113.6 (3) | H18A—C18—H18C | 109.5 |
C4—C5—C6 | 122.0 (3) | H18B—C18—H18C | 109.5 |
C4—C5—C10 | 124.5 (3) | O3—C19—O4 | 124.7 (3) |
C6—C5—C10 | 113.5 (3) | O3—C19—C15 | 122.9 (3) |
C5—C6—C7 | 112.2 (3) | O4—C19—C15 | 112.3 (3) |
C5—C6—H6A | 109.2 | O4—C20—H20A | 109.5 |
C7—C6—H6A | 109.2 | O4—C20—H20B | 109.5 |
C5—C6—H6B | 109.2 | H20A—C20—H20B | 109.5 |
C7—C6—H6B | 109.2 | O4—C20—H20C | 109.5 |
H6A—C6—H6B | 107.9 | H20A—C20—H20C | 109.5 |
C6—C7—C8 | 112.5 (2) | H20B—C20—H20C | 109.5 |
C6—C7—H7A | 109.1 | C4—C21—H21A | 109.5 |
C8—C7—H7A | 109.1 | C4—C21—H21B | 109.5 |
C6—C7—H7B | 109.1 | H21A—C21—H21B | 109.5 |
C8—C7—H7B | 109.1 | C4—C21—H21C | 109.5 |
H7A—C7—H7B | 107.8 | H21A—C21—H21C | 109.5 |
C7—C8—C22 | 108.3 (2) | H21B—C21—H21C | 109.5 |
C7—C8—C14 | 109.6 (2) | O5—C22—O6 | 122.5 (3) |
C22—C8—C14 | 104.6 (2) | O5—C22—C8 | 125.0 (3) |
C7—C8—C9 | 108.9 (2) | O6—C22—C8 | 112.4 (3) |
C22—C8—C9 | 116.5 (2) | O6—C23—H23A | 109.5 |
C14—C8—C9 | 108.8 (2) | O6—C23—H23B | 109.5 |
C11—C9—C8 | 112.4 (2) | H23A—C23—H23B | 109.5 |
C11—C9—C10 | 114.8 (2) | O6—C23—H23C | 109.5 |
C8—C9—C10 | 115.6 (2) | H23A—C23—H23C | 109.5 |
C11—C9—H9 | 104.1 | H23B—C23—H23C | 109.5 |
C8—C9—H9 | 104.1 | C10—C24—H24A | 109.5 |
C10—C9—H9 | 104.1 | C10—C24—H24B | 109.5 |
C1—C10—C5 | 110.5 (2) | H24A—C24—H24B | 109.5 |
C1—C10—C24 | 108.4 (3) | C10—C24—H24C | 109.5 |
C5—C10—C24 | 110.1 (3) | H24A—C24—H24C | 109.5 |
C1—C10—C9 | 108.1 (2) | H24B—C24—H24C | 109.5 |
C5—C10—C9 | 107.2 (2) | C13—C25—H25A | 109.5 |
C24—C10—C9 | 112.6 (2) | C13—C25—H25B | 109.5 |
C12—C11—C9 | 111.9 (3) | H25A—C25—H25B | 109.5 |
C12—C11—H11A | 109.2 | C13—C25—H25C | 109.5 |
C9—C11—H11A | 109.2 | H25A—C25—H25C | 109.5 |
C12—C11—H11B | 109.2 | H25B—C25—H25C | 109.5 |
C9—C11—H11B | 109.2 | C17—O2—C18 | 115.7 (3) |
H11A—C11—H11B | 107.9 | C19—O4—C20 | 115.3 (3) |
C13—C12—C11 | 125.1 (3) | C22—O6—C23 | 115.2 (3) |
C13—C12—H12 | 117.5 | | |
| | | |
C10—C1—C2—C3 | −63.1 (4) | C10—C9—C11—C12 | −177.4 (2) |
C1—C2—C3—C4 | 49.8 (4) | C9—C11—C12—C13 | −18.4 (4) |
C1—C2—C3—C15 | −76.8 (3) | C11—C12—C13—C14 | −5.2 (5) |
C2—C3—C4—C5 | −17.5 (4) | C11—C12—C13—C25 | 177.7 (3) |
C15—C3—C4—C5 | 108.6 (3) | C12—C13—C14—O7 | −178.4 (3) |
C2—C3—C4—C21 | 160.8 (3) | C25—C13—C14—O7 | −1.2 (4) |
C15—C3—C4—C21 | −73.0 (4) | C12—C13—C14—C8 | −1.7 (4) |
C3—C4—C5—C6 | 177.5 (3) | C25—C13—C14—C8 | 175.6 (3) |
C21—C4—C5—C6 | −0.7 (5) | C7—C8—C14—O7 | −34.1 (4) |
C3—C4—C5—C10 | −4.7 (5) | C22—C8—C14—O7 | 81.8 (3) |
C21—C4—C5—C10 | 177.1 (3) | C9—C8—C14—O7 | −153.1 (3) |
C4—C5—C6—C7 | 121.0 (3) | C7—C8—C14—C13 | 149.1 (3) |
C10—C5—C6—C7 | −57.0 (4) | C22—C8—C14—C13 | −95.0 (3) |
C5—C6—C7—C8 | 55.6 (4) | C9—C8—C14—C13 | 30.1 (3) |
C6—C7—C8—C22 | 75.3 (3) | C4—C3—C15—C16 | −24.9 (5) |
C6—C7—C8—C14 | −171.1 (2) | C2—C3—C15—C16 | 101.2 (4) |
C6—C7—C8—C9 | −52.2 (3) | C4—C3—C15—C19 | 152.7 (3) |
C7—C8—C9—C11 | −172.1 (2) | C2—C3—C15—C19 | −81.2 (3) |
C22—C8—C9—C11 | 65.2 (3) | C19—C15—C16—C17 | −0.2 (5) |
C14—C8—C9—C11 | −52.7 (3) | C3—C15—C16—C17 | 177.2 (3) |
C7—C8—C9—C10 | 53.5 (3) | C15—C16—C17—O1 | −6.7 (6) |
C22—C8—C9—C10 | −69.2 (3) | C15—C16—C17—O2 | 175.9 (3) |
C14—C8—C9—C10 | 172.9 (2) | C16—C15—C19—O3 | 105.0 (4) |
C2—C1—C10—C5 | 40.0 (4) | C3—C15—C19—O3 | −72.6 (4) |
C2—C1—C10—C24 | −80.7 (3) | C16—C15—C19—O4 | −78.7 (4) |
C2—C1—C10—C9 | 157.1 (3) | C3—C15—C19—O4 | 103.6 (3) |
C4—C5—C10—C1 | −6.6 (4) | C7—C8—C22—O5 | −1.4 (4) |
C6—C5—C10—C1 | 171.4 (2) | C14—C8—C22—O5 | −118.2 (3) |
C4—C5—C10—C24 | 113.1 (3) | C9—C8—C22—O5 | 121.6 (3) |
C6—C5—C10—C24 | −68.9 (3) | C7—C8—C22—O6 | 174.6 (2) |
C4—C5—C10—C9 | −124.1 (3) | C14—C8—C22—O6 | 57.8 (3) |
C6—C5—C10—C9 | 53.8 (3) | C9—C8—C22—O6 | −62.4 (3) |
C11—C9—C10—C1 | 54.1 (3) | O1—C17—O2—C18 | −0.4 (6) |
C8—C9—C10—C1 | −172.6 (2) | C16—C17—O2—C18 | 177.2 (3) |
C11—C9—C10—C5 | 173.2 (3) | O3—C19—O4—C20 | −8.2 (5) |
C8—C9—C10—C5 | −53.4 (3) | C15—C19—O4—C20 | 175.6 (3) |
C11—C9—C10—C24 | −65.6 (3) | O5—C22—O6—C23 | −0.8 (5) |
C8—C9—C10—C24 | 67.8 (3) | C8—C22—O6—C23 | −177.0 (3) |
C8—C9—C11—C12 | 47.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···O7i | 0.96 | 2.47 | 3.424 (5) | 170 |
C20—H20B···O7ii | 0.96 | 2.42 | 3.344 (5) | 161 |
C25—H25C···O3ii | 0.96 | 2.70 | 3.607 (5) | 158 |
C24—H24A···O3iii | 0.96 | 2.84 | 3.755 (4) | 160 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+2; (iii) −x, y−1/2, −z+5/2. |