The title compound, namely (2′
S,3′
S,3a
R,5′
R,6a
S,9
R,9a
S,10a
R)-1,3a,4,4′,5′,6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3′,9,10a-trimethyl-5′-(2-methylpropen-1-yl)-7-oxospiro[dicyclopenta[
a,
d]cyclooctene-3(2
H),2′(3′
H)-furan]-6-carbaldehyde, C
25H
36O
4, displays phytotoxic behaviour that may be correlated with some structural features of the molecule. The eight-membered ring of the terpenoid tricyclic skeleton is
cis- and
trans-joined with the fused five-membered rings. One intramolecular O—H
O hydrogen bond and two intermolecular C—H
O hydrogen bonds are present.
Supporting information
CCDC reference: 610875
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.007 Å
- R factor = 0.054
- wR factor = 0.114
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.112
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.50 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C24
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.00
From the CIF: _reflns_number_total 2208
Count of symmetry unique reflns 2244
Completeness (_total/calc) 98.40%
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(2'S,3'S,3aR,5'
R,6aS,9
R,9aS,10aR)-1,3a,4,4',5',6a,7,8,9,9a,10,10
a-
dodecahydro-9-hydroxy-3',9,10
a-trimethyl-5'-(2-methylpropen-1-yl)-7-
oxospiro[dicyclopenta[a,d]cyclooctene-3(2
H),2'(3'
H)-furan]-6-carbaldehyde
top
Crystal data top
C25H36O4 | F(000) = 872 |
Mr = 400.54 | Dx = 1.210 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 192 reflections |
a = 7.251 (4) Å | θ = 4.1–24.2° |
b = 14.756 (9) Å | µ = 0.08 mm−1 |
c = 20.55 (2) Å | T = 173 K |
V = 2199 (3) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.20 × 0.07 mm |
Data collection top
Bruker Nonius KappaCCD area-detector diffractometer | 2208 independent reflections |
Radiation source: fine-focus sealed tube | 1356 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.112 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 3° |
Thick–slice φ and ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Bruker Nonius, 2002) | k = −17→16 |
Tmin = 0.980, Tmax = 0.994 | l = −24→20 |
7226 measured reflections | |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.6026P] where P = (Fo2 + 2Fc2)/3 |
2208 reflections | (Δ/σ)max < 0.001 |
267 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.25 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 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 | |
O1 | 0.9599 (4) | 0.5785 (2) | 0.55823 (15) | 0.0298 (9) | |
H1 | 0.9345 | 0.6298 | 0.5430 | 0.030* | |
O2 | 1.2591 (5) | 0.6516 (2) | 0.38921 (19) | 0.0384 (10) | |
O3 | 0.9319 (5) | 0.7256 (2) | 0.47325 (18) | 0.0359 (9) | |
O4 | 0.2862 (4) | 0.4017 (2) | 0.32500 (14) | 0.0254 (8) | |
C1 | 0.7966 (6) | 0.4362 (3) | 0.4762 (2) | 0.0209 (11) | |
H1A | 0.7113 | 0.4865 | 0.4866 | 0.021* | |
H1B | 0.8068 | 0.3982 | 0.5158 | 0.021* | |
C2 | 0.9863 (6) | 0.4771 (3) | 0.4628 (2) | 0.0206 (12) | |
H2 | 1.0666 | 0.4256 | 0.4488 | 0.021* | |
C3 | 1.0823 (6) | 0.5195 (3) | 0.5234 (2) | 0.0224 (12) | |
C4 | 1.2423 (6) | 0.5728 (3) | 0.4925 (2) | 0.0275 (13) | |
H4A | 1.2709 | 0.6273 | 0.5188 | 0.027* | |
H4B | 1.3543 | 0.5346 | 0.4900 | 0.027* | |
C5 | 1.1801 (7) | 0.5999 (3) | 0.4252 (3) | 0.0271 (12) | |
C6 | 1.0028 (6) | 0.5502 (3) | 0.4086 (2) | 0.0234 (12) | |
H6 | 1.0236 | 0.5177 | 0.3665 | 0.023* | |
C7 | 0.8372 (7) | 0.6116 (3) | 0.3993 (2) | 0.0233 (12) | |
C8 | 0.6930 (7) | 0.5878 (3) | 0.3629 (2) | 0.0252 (12) | |
H8 | 0.5968 | 0.6311 | 0.3589 | 0.025* | |
C9 | 0.6670 (7) | 0.4999 (3) | 0.3277 (2) | 0.0255 (12) | |
H9A | 0.7875 | 0.4774 | 0.3119 | 0.025* | |
H9B | 0.5856 | 0.5091 | 0.2896 | 0.025* | |
C10 | 0.5805 (6) | 0.4298 (3) | 0.3739 (2) | 0.0163 (11) | |
H10 | 0.4943 | 0.4655 | 0.4019 | 0.016* | |
C11 | 0.7058 (6) | 0.3780 (3) | 0.4225 (2) | 0.0202 (11) | |
C12 | 0.5579 (7) | 0.3157 (3) | 0.4529 (2) | 0.0244 (12) | |
H12A | 0.6161 | 0.2613 | 0.4722 | 0.024* | |
H12B | 0.4895 | 0.3482 | 0.4874 | 0.024* | |
C13 | 0.4280 (7) | 0.2888 (3) | 0.3977 (2) | 0.0254 (12) | |
H13A | 0.2983 | 0.2909 | 0.4127 | 0.025* | |
H13B | 0.4557 | 0.2265 | 0.3827 | 0.025* | |
C14 | 0.4586 (6) | 0.3572 (3) | 0.3417 (2) | 0.0247 (12) | |
C15 | 0.5354 (7) | 0.3191 (3) | 0.2756 (2) | 0.0277 (13) | |
H15 | 0.6659 | 0.3397 | 0.2704 | 0.028* | |
C16 | 0.4164 (7) | 0.3667 (4) | 0.2242 (2) | 0.0307 (13) | |
H16A | 0.4723 | 0.4250 | 0.2108 | 0.031* | |
H16B | 0.4002 | 0.3280 | 0.1853 | 0.031* | |
C17 | 0.2326 (7) | 0.3818 (3) | 0.2591 (2) | 0.0285 (13) | |
H17 | 0.1573 | 0.3251 | 0.2579 | 0.029* | |
C18 | 0.1223 (6) | 0.4595 (4) | 0.2337 (2) | 0.0318 (14) | |
H18 | 0.1508 | 0.5172 | 0.2514 | 0.032* | |
C19 | −0.0096 (7) | 0.4577 (4) | 0.1898 (2) | 0.0363 (14) | |
C20 | 1.1435 (7) | 0.4498 (4) | 0.5724 (2) | 0.0334 (14) | |
H20A | 1.2119 | 0.4798 | 0.6075 | 0.033* | |
H20B | 1.2232 | 0.4052 | 0.5511 | 0.033* | |
H20C | 1.0351 | 0.4192 | 0.5906 | 0.033* | |
C21 | 0.8247 (7) | 0.6984 (4) | 0.4332 (3) | 0.0312 (13) | |
H21 | 0.7233 | 0.7364 | 0.4227 | 0.031* | |
C22 | 0.8522 (6) | 0.3181 (3) | 0.3887 (2) | 0.0226 (12) | |
H22A | 0.9302 | 0.3560 | 0.3608 | 0.023* | |
H22B | 0.7906 | 0.2720 | 0.3622 | 0.023* | |
H22C | 0.9288 | 0.2885 | 0.4218 | 0.023* | |
C23 | 0.5289 (8) | 0.2167 (4) | 0.2665 (3) | 0.0403 (15) | |
H23A | 0.4008 | 0.1958 | 0.2695 | 0.040* | |
H23B | 0.6027 | 0.1873 | 0.3004 | 0.040* | |
H23C | 0.5788 | 0.2010 | 0.2236 | 0.040* | |
C24 | −0.1017 (8) | 0.5426 (5) | 0.1668 (3) | 0.0556 (19) | |
H24A | −0.0512 | 0.5947 | 0.1904 | 0.056* | |
H24B | −0.2347 | 0.5384 | 0.1749 | 0.056* | |
H24C | −0.0797 | 0.5503 | 0.1201 | 0.056* | |
C25 | −0.0768 (8) | 0.3725 (5) | 0.1568 (3) | 0.0542 (19) | |
H25A | −0.0414 | 0.3737 | 0.1108 | 0.054* | |
H25B | −0.2114 | 0.3689 | 0.1603 | 0.054* | |
H25C | −0.0213 | 0.3195 | 0.1779 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.032 (2) | 0.024 (2) | 0.034 (2) | 0.0062 (16) | 0.0032 (17) | −0.0072 (17) |
O2 | 0.029 (2) | 0.041 (2) | 0.045 (2) | −0.0038 (18) | 0.0115 (19) | 0.009 (2) |
O3 | 0.041 (2) | 0.023 (2) | 0.044 (2) | 0.0047 (18) | −0.006 (2) | −0.0072 (19) |
O4 | 0.0224 (18) | 0.038 (2) | 0.0154 (18) | 0.0064 (16) | −0.0032 (15) | −0.0013 (16) |
C1 | 0.020 (3) | 0.021 (3) | 0.022 (3) | 0.004 (2) | −0.002 (2) | 0.004 (2) |
C2 | 0.019 (3) | 0.023 (3) | 0.020 (3) | 0.003 (2) | 0.000 (2) | −0.002 (2) |
C3 | 0.019 (3) | 0.023 (3) | 0.025 (3) | −0.001 (2) | 0.001 (2) | −0.003 (2) |
C4 | 0.018 (3) | 0.029 (3) | 0.035 (3) | −0.005 (2) | −0.002 (2) | −0.009 (2) |
C5 | 0.017 (3) | 0.027 (3) | 0.037 (3) | 0.005 (2) | 0.006 (2) | −0.001 (3) |
C6 | 0.026 (3) | 0.024 (3) | 0.020 (3) | 0.004 (2) | 0.006 (2) | −0.002 (2) |
C7 | 0.026 (3) | 0.019 (3) | 0.024 (3) | 0.001 (2) | 0.003 (2) | 0.000 (2) |
C8 | 0.027 (3) | 0.019 (3) | 0.029 (3) | 0.001 (2) | 0.007 (2) | 0.009 (2) |
C9 | 0.028 (3) | 0.032 (3) | 0.016 (3) | −0.003 (2) | −0.003 (2) | 0.007 (2) |
C10 | 0.018 (2) | 0.017 (3) | 0.015 (3) | −0.001 (2) | 0.004 (2) | −0.002 (2) |
C11 | 0.021 (3) | 0.022 (3) | 0.018 (3) | −0.002 (2) | −0.002 (2) | 0.002 (2) |
C12 | 0.027 (3) | 0.027 (3) | 0.019 (3) | −0.007 (2) | −0.004 (2) | 0.002 (2) |
C13 | 0.025 (3) | 0.026 (3) | 0.025 (3) | −0.004 (2) | 0.004 (2) | 0.000 (2) |
C14 | 0.018 (3) | 0.028 (3) | 0.028 (3) | 0.008 (2) | 0.000 (2) | −0.003 (2) |
C15 | 0.022 (3) | 0.033 (3) | 0.028 (3) | 0.003 (2) | 0.002 (2) | −0.002 (3) |
C16 | 0.023 (3) | 0.048 (4) | 0.021 (3) | 0.001 (3) | −0.001 (2) | −0.002 (3) |
C17 | 0.024 (3) | 0.042 (3) | 0.020 (3) | 0.000 (3) | −0.004 (2) | −0.007 (3) |
C18 | 0.026 (3) | 0.042 (4) | 0.027 (3) | 0.003 (3) | 0.004 (3) | 0.006 (3) |
C19 | 0.020 (3) | 0.069 (4) | 0.020 (3) | 0.011 (3) | 0.005 (2) | 0.010 (3) |
C20 | 0.037 (3) | 0.035 (4) | 0.028 (3) | −0.002 (3) | −0.008 (3) | −0.005 (3) |
C21 | 0.034 (3) | 0.023 (3) | 0.036 (3) | 0.008 (3) | 0.005 (3) | 0.005 (3) |
C22 | 0.023 (3) | 0.022 (3) | 0.023 (3) | 0.000 (2) | −0.007 (2) | −0.003 (2) |
C23 | 0.036 (3) | 0.050 (4) | 0.035 (4) | −0.001 (3) | −0.007 (3) | −0.009 (3) |
C24 | 0.040 (4) | 0.088 (5) | 0.039 (4) | 0.019 (4) | 0.004 (3) | 0.026 (4) |
C25 | 0.032 (3) | 0.096 (6) | 0.034 (4) | 0.007 (3) | −0.007 (3) | −0.004 (4) |
Geometric parameters (Å, º) top
O1—C3 | 1.434 (5) | C12—H12A | 0.9900 |
O1—H1 | 0.8400 | C12—H12B | 0.9900 |
O2—C5 | 1.207 (6) | C13—C14 | 1.546 (7) |
O3—C21 | 1.202 (6) | C13—H13A | 0.9900 |
O4—C17 | 1.439 (6) | C13—H13B | 0.9900 |
O4—C14 | 1.453 (5) | C14—C15 | 1.573 (7) |
C1—C2 | 1.527 (6) | C15—C23 | 1.524 (7) |
C1—C11 | 1.546 (6) | C15—C16 | 1.534 (7) |
C1—H1A | 0.9900 | C15—H15 | 1.0000 |
C1—H1B | 0.9900 | C16—C17 | 1.530 (7) |
C2—C6 | 1.556 (6) | C16—H16A | 0.9900 |
C2—C3 | 1.557 (6) | C16—H16B | 0.9900 |
C2—H2 | 1.0000 | C17—C18 | 1.491 (7) |
C3—C20 | 1.506 (7) | C17—H17 | 1.0000 |
C3—C4 | 1.539 (7) | C18—C19 | 1.315 (7) |
C4—C5 | 1.509 (7) | C18—H18 | 0.9500 |
C4—H4A | 0.9900 | C19—C24 | 1.496 (8) |
C4—H4B | 0.9900 | C19—C25 | 1.510 (8) |
C5—C6 | 1.519 (7) | C20—H20A | 0.9800 |
C6—C7 | 1.515 (6) | C20—H20B | 0.9800 |
C6—H6 | 1.0000 | C20—H20C | 0.9800 |
C7—C8 | 1.332 (7) | C21—H21 | 0.9500 |
C7—C21 | 1.460 (7) | C22—H22A | 0.9800 |
C8—C9 | 1.497 (7) | C22—H22B | 0.9800 |
C8—H8 | 0.9500 | C22—H22C | 0.9800 |
C9—C10 | 1.537 (6) | C23—H23A | 0.9800 |
C9—H9A | 0.9900 | C23—H23B | 0.9800 |
C9—H9B | 0.9900 | C23—H23C | 0.9800 |
C10—C14 | 1.538 (6) | C24—H24A | 0.9800 |
C10—C11 | 1.551 (6) | C24—H24B | 0.9800 |
C10—H10 | 1.0000 | C24—H24C | 0.9800 |
C11—C12 | 1.544 (6) | C25—H25A | 0.9800 |
C11—C22 | 1.546 (6) | C25—H25B | 0.9800 |
C12—C13 | 1.527 (6) | C25—H25C | 0.9800 |
| | | |
C3—O1—H1 | 119.8 | C14—C13—H13A | 110.3 |
C17—O4—C14 | 111.3 (3) | C12—C13—H13B | 110.3 |
C2—C1—C11 | 118.3 (4) | C14—C13—H13B | 110.3 |
C2—C1—H1A | 107.7 | H13A—C13—H13B | 108.5 |
C11—C1—H1A | 107.7 | O4—C14—C10 | 106.3 (4) |
C2—C1—H1B | 107.7 | O4—C14—C13 | 110.3 (4) |
C11—C1—H1B | 107.7 | C10—C14—C13 | 102.5 (4) |
H1A—C1—H1B | 107.1 | O4—C14—C15 | 105.2 (4) |
C1—C2—C6 | 118.2 (4) | C10—C14—C15 | 114.7 (4) |
C1—C2—C3 | 114.7 (4) | C13—C14—C15 | 117.4 (4) |
C6—C2—C3 | 105.0 (4) | C23—C15—C16 | 110.6 (4) |
C1—C2—H2 | 106.0 | C23—C15—C14 | 116.8 (4) |
C6—C2—H2 | 106.0 | C16—C15—C14 | 103.4 (4) |
C3—C2—H2 | 106.0 | C23—C15—H15 | 108.6 |
O1—C3—C20 | 105.2 (4) | C16—C15—H15 | 108.6 |
O1—C3—C4 | 111.2 (4) | C14—C15—H15 | 108.6 |
C20—C3—C4 | 113.8 (4) | C17—C16—C15 | 103.5 (4) |
O1—C3—C2 | 111.5 (4) | C17—C16—H16A | 111.1 |
C20—C3—C2 | 113.1 (4) | C15—C16—H16A | 111.1 |
C4—C3—C2 | 102.3 (4) | C17—C16—H16B | 111.1 |
C5—C4—C3 | 106.7 (4) | C15—C16—H16B | 111.1 |
C5—C4—H4A | 110.4 | H16A—C16—H16B | 109.0 |
C3—C4—H4A | 110.4 | O4—C17—C18 | 108.5 (4) |
C5—C4—H4B | 110.4 | O4—C17—C16 | 103.6 (4) |
C3—C4—H4B | 110.4 | C18—C17—C16 | 114.5 (4) |
H4A—C4—H4B | 108.6 | O4—C17—H17 | 110.0 |
O2—C5—C4 | 125.9 (5) | C18—C17—H17 | 110.0 |
O2—C5—C6 | 124.7 (5) | C16—C17—H17 | 110.0 |
C4—C5—C6 | 109.3 (4) | C19—C18—C17 | 128.0 (6) |
C7—C6—C5 | 114.2 (4) | C19—C18—H18 | 116.0 |
C7—C6—C2 | 116.3 (4) | C17—C18—H18 | 116.0 |
C5—C6—C2 | 103.8 (4) | C18—C19—C24 | 121.7 (6) |
C7—C6—H6 | 107.3 | C18—C19—C25 | 124.0 (6) |
C5—C6—H6 | 107.3 | C24—C19—C25 | 114.3 (5) |
C2—C6—H6 | 107.3 | C3—C20—H20A | 109.5 |
C8—C7—C21 | 116.7 (5) | C3—C20—H20B | 109.5 |
C8—C7—C6 | 122.3 (4) | H20A—C20—H20B | 109.5 |
C21—C7—C6 | 120.9 (4) | C3—C20—H20C | 109.5 |
C7—C8—C9 | 126.7 (4) | H20A—C20—H20C | 109.5 |
C7—C8—H8 | 116.6 | H20B—C20—H20C | 109.5 |
C9—C8—H8 | 116.6 | O3—C21—C7 | 125.4 (5) |
C8—C9—C10 | 109.6 (4) | O3—C21—H21 | 117.3 |
C8—C9—H9A | 109.7 | C7—C21—H21 | 117.3 |
C10—C9—H9A | 109.7 | C11—C22—H22A | 109.5 |
C8—C9—H9B | 109.7 | C11—C22—H22B | 109.5 |
C10—C9—H9B | 109.7 | H22A—C22—H22B | 109.5 |
H9A—C9—H9B | 108.2 | C11—C22—H22C | 109.5 |
C9—C10—C14 | 115.9 (4) | H22A—C22—H22C | 109.5 |
C9—C10—C11 | 119.3 (4) | H22B—C22—H22C | 109.5 |
C14—C10—C11 | 105.6 (4) | C15—C23—H23A | 109.5 |
C9—C10—H10 | 104.8 | C15—C23—H23B | 109.5 |
C14—C10—H10 | 104.8 | H23A—C23—H23B | 109.5 |
C11—C10—H10 | 104.8 | C15—C23—H23C | 109.5 |
C12—C11—C22 | 108.6 (4) | H23A—C23—H23C | 109.5 |
C12—C11—C1 | 109.7 (4) | H23B—C23—H23C | 109.5 |
C22—C11—C1 | 110.2 (4) | C19—C24—H24A | 109.5 |
C12—C11—C10 | 98.5 (4) | C19—C24—H24B | 109.5 |
C22—C11—C10 | 113.3 (4) | H24A—C24—H24B | 109.5 |
C1—C11—C10 | 115.8 (4) | C19—C24—H24C | 109.5 |
C13—C12—C11 | 106.4 (4) | H24A—C24—H24C | 109.5 |
C13—C12—H12A | 110.5 | H24B—C24—H24C | 109.5 |
C11—C12—H12A | 110.5 | C19—C25—H25A | 109.5 |
C13—C12—H12B | 110.5 | C19—C25—H25B | 109.5 |
C11—C12—H12B | 110.5 | H25A—C25—H25B | 109.5 |
H12A—C12—H12B | 108.6 | C19—C25—H25C | 109.5 |
C12—C13—C14 | 107.1 (4) | H25A—C25—H25C | 109.5 |
C12—C13—H13A | 110.3 | H25B—C25—H25C | 109.5 |
| | | |
C11—C1—C2—C6 | 65.8 (6) | C9—C10—C11—C1 | 66.0 (5) |
C11—C1—C2—C3 | −169.4 (4) | C14—C10—C11—C1 | −161.3 (4) |
C1—C2—C3—O1 | −48.5 (5) | C22—C11—C12—C13 | −80.6 (5) |
C6—C2—C3—O1 | 82.9 (4) | C1—C11—C12—C13 | 158.9 (4) |
C1—C2—C3—C20 | 69.8 (5) | C10—C11—C12—C13 | 37.5 (5) |
C6—C2—C3—C20 | −158.8 (4) | C11—C12—C13—C14 | −17.9 (5) |
C1—C2—C3—C4 | −167.5 (4) | C17—O4—C14—C10 | 132.1 (4) |
C6—C2—C3—C4 | −36.0 (4) | C17—O4—C14—C13 | −117.4 (4) |
O1—C3—C4—C5 | −90.6 (5) | C17—O4—C14—C15 | 10.1 (5) |
C20—C3—C4—C5 | 150.9 (4) | C9—C10—C14—O4 | −75.1 (5) |
C2—C3—C4—C5 | 28.6 (5) | C11—C10—C14—O4 | 150.3 (4) |
C3—C4—C5—O2 | 170.4 (5) | C9—C10—C14—C13 | 169.0 (4) |
C3—C4—C5—C6 | −10.7 (5) | C11—C10—C14—C13 | 34.5 (4) |
O2—C5—C6—C7 | −65.3 (6) | C9—C10—C14—C15 | 40.6 (5) |
C4—C5—C6—C7 | 115.8 (5) | C11—C10—C14—C15 | −93.9 (4) |
O2—C5—C6—C2 | 167.0 (5) | C12—C13—C14—O4 | −122.9 (4) |
C4—C5—C6—C2 | −11.9 (5) | C12—C13—C14—C10 | −9.9 (5) |
C1—C2—C6—C7 | 32.8 (6) | C12—C13—C14—C15 | 116.7 (4) |
C3—C2—C6—C7 | −96.6 (5) | O4—C14—C15—C23 | −108.6 (5) |
C1—C2—C6—C5 | 159.2 (4) | C10—C14—C15—C23 | 135.0 (5) |
C3—C2—C6—C5 | 29.8 (4) | C13—C14—C15—C23 | 14.5 (6) |
C5—C6—C7—C8 | 154.9 (5) | O4—C14—C15—C16 | 13.1 (5) |
C2—C6—C7—C8 | −84.1 (6) | C10—C14—C15—C16 | −103.3 (5) |
C5—C6—C7—C21 | −28.4 (7) | C13—C14—C15—C16 | 136.2 (4) |
C2—C6—C7—C21 | 92.6 (5) | C23—C15—C16—C17 | 95.9 (5) |
C21—C7—C8—C9 | −175.2 (4) | C14—C15—C16—C17 | −29.9 (5) |
C6—C7—C8—C9 | 1.6 (8) | C14—O4—C17—C18 | −151.4 (4) |
C7—C8—C9—C10 | 86.2 (6) | C14—O4—C17—C16 | −29.3 (5) |
C8—C9—C10—C14 | 150.4 (4) | C15—C16—C17—O4 | 36.3 (5) |
C8—C9—C10—C11 | −81.5 (5) | C15—C16—C17—C18 | 154.3 (4) |
C2—C1—C11—C12 | 159.0 (4) | O4—C17—C18—C19 | −150.5 (5) |
C2—C1—C11—C22 | 39.5 (5) | C16—C17—C18—C19 | 94.3 (6) |
C2—C1—C11—C10 | −90.7 (5) | C17—C18—C19—C24 | −176.9 (5) |
C9—C10—C11—C12 | −177.2 (4) | C17—C18—C19—C25 | 1.0 (9) |
C14—C10—C11—C12 | −44.5 (4) | C8—C7—C21—O3 | 171.4 (5) |
C9—C10—C11—C22 | −62.7 (5) | C6—C7—C21—O3 | −5.4 (8) |
C14—C10—C11—C22 | 70.0 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.84 | 2.01 | 2.794 (5) | 154 |
C4—H4A···O3i | 0.99 | 2.47 | 3.352 (6) | 148 |
C8—H8···O2ii | 0.95 | 2.54 | 3.328 (6) | 140 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1, y, z. |