The title compound, methyl 2-[4-(3-furyl)-6b,10a-dihydroxy-3a,7,9,9-tetramethyl-6,10-dioxo-2,3,3a,6b,7,8,9,10,10a,11-decahydro-1a
H,4
H,6
H-benzo[
h][1]benzoxireno[3,2,1a-
de]isochromen-8-yl]acetate, C
27H
32O
9, is a new tetranortriterpenoid which was isolated for the first time from the seeds of
Lansium domesticum Coor. The four six-membered rings adopt chair, boat, envelope and screw-boat conformations. The furan substituent is planar and is attached equatorially to the lactone ring. O—H
O hydrogen bonds link the molecules into chains along [100] and adjacent chains are interconnected by C—H
O interactions.
Supporting information
CCDC reference: 620752
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.120
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.36 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for O5 - C19 .. 20.58 su
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.44 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C18 .. 5.03 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5
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 27.00
From the CIF: _reflns_number_total 2973
Count of symmetry unique reflns 2979
Completeness (_total/calc) 99.80%
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
9 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 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
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: K. Chantrapromma and K. Chaiyadej are involved in the extraction,
crystallisation and bioactivity testing of the title compound. X.-L Yu is
involved in data collection at Sun Yat-Sen University. H. K. Fun,
S. Chantrapromma and N. Boonnak are involved in structure determination,
literature survey and write-up the manuscript. All co-authors are
involved in the preparing of this manuscript.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
methyl 2-[4-(3-furyl)-6 b,10
a-dihydroxy-3a,7,9,9-
tetramethyl-6,10-dioxo-2,3,3a,6 b,7,8,9,10,10
a,11-decahydro-
1aH,4
H,6
H-benzo[
h][1]benzoxireno[3,2,1a-de]isochromen-
8-yl]acetate
top
Crystal data top
C27H32O9 | Dx = 1.385 Mg m−3 |
Mr = 500.53 | Melting point = 508–510 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2973 reflections |
a = 7.9634 (5) Å | θ = 1.7–27.0° |
b = 14.6700 (9) Å | µ = 0.10 mm−1 |
c = 20.5420 (13) Å | T = 297 K |
V = 2399.8 (3) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.39 × 0.34 mm |
F(000) = 1064 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2973 independent reflections |
Radiation source: fine-focus sealed tube | 2814 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.0°, θmin = 1.7° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −18→16 |
Tmin = 0.952, Tmax = 0.965 | l = −18→26 |
14158 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0826P)2 + 0.3239P] where P = (Fo2 + 2Fc2)/3 |
2973 reflections | (Δ/σ)max = 0.001 |
332 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.21 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 | 0.3417 (3) | 0.42137 (16) | 0.94558 (8) | 0.0573 (5) | |
O2 | −0.0711 (2) | 0.67442 (11) | 0.71401 (8) | 0.0439 (4) | |
O3 | 0.1010 (3) | 0.73760 (11) | 0.78354 (10) | 0.0545 (5) | |
O4 | 0.3539 (2) | 0.41907 (12) | 0.67264 (9) | 0.0487 (4) | |
O5 | −0.4622 (3) | 0.6333 (2) | 0.55878 (12) | 0.0829 (8) | |
O6 | 0.8865 (2) | 0.63985 (16) | 0.90276 (11) | 0.0609 (5) | |
O7 | 0.7483 (3) | 0.65404 (16) | 0.99688 (9) | 0.0663 (6) | |
O8 | 0.0867 (2) | 0.45683 (14) | 0.87279 (10) | 0.0518 (5) | |
H8 | 0.1006 | 0.4433 | 0.9111 | 0.078* | |
O9 | 0.2410 (2) | 0.61846 (11) | 0.87195 (7) | 0.0369 (3) | |
H9 | 0.1402 | 0.6201 | 0.8799 | 0.055* | |
C1 | 0.4535 (3) | 0.57717 (13) | 0.79440 (10) | 0.0302 (4) | |
H1 | 0.4736 | 0.5336 | 0.7591 | 0.036* | |
C2 | 0.5847 (3) | 0.55552 (14) | 0.84822 (10) | 0.0311 (4) | |
H2 | 0.6949 | 0.5597 | 0.8273 | 0.037* | |
C3 | 0.5687 (3) | 0.45551 (14) | 0.87311 (11) | 0.0351 (5) | |
C4 | 0.3840 (3) | 0.44180 (14) | 0.89109 (10) | 0.0357 (5) | |
C5 | 0.2447 (3) | 0.46152 (14) | 0.84100 (10) | 0.0349 (4) | |
C6 | 0.2696 (3) | 0.56225 (13) | 0.81715 (9) | 0.0305 (4) | |
C7 | 0.1472 (3) | 0.57899 (14) | 0.76116 (10) | 0.0324 (4) | |
C8 | 0.1266 (3) | 0.51765 (14) | 0.71362 (10) | 0.0333 (4) | |
C9 | 0.2140 (3) | 0.42807 (14) | 0.71819 (11) | 0.0355 (4) | |
C10 | 0.2387 (4) | 0.39123 (15) | 0.78561 (11) | 0.0428 (5) | |
H10A | 0.3427 | 0.3569 | 0.7863 | 0.051* | |
H10B | 0.1482 | 0.3488 | 0.7947 | 0.051* | |
C11 | 0.2032 (3) | 0.36382 (16) | 0.66361 (12) | 0.0454 (6) | |
H11 | 0.2145 | 0.2993 | 0.6752 | 0.055* | |
C12 | 0.0932 (4) | 0.3833 (2) | 0.60616 (13) | 0.0576 (7) | |
H12A | 0.0439 | 0.3269 | 0.5907 | 0.069* | |
H12B | 0.1607 | 0.4087 | 0.5713 | 0.069* | |
C13 | −0.0456 (4) | 0.44992 (17) | 0.62364 (13) | 0.0462 (6) | |
H13A | −0.1218 | 0.4209 | 0.6541 | 0.055* | |
H13B | −0.1088 | 0.4646 | 0.5847 | 0.055* | |
C14 | 0.0207 (3) | 0.53885 (15) | 0.65406 (10) | 0.0352 (5) | |
C15 | −0.1284 (3) | 0.59405 (15) | 0.67925 (11) | 0.0375 (5) | |
H15 | −0.1918 | 0.5558 | 0.7097 | 0.045* | |
C16 | 0.0602 (3) | 0.66868 (15) | 0.75522 (11) | 0.0374 (5) | |
C17 | −0.2467 (3) | 0.62764 (17) | 0.62785 (11) | 0.0429 (5) | |
C18 | −0.3890 (4) | 0.5846 (2) | 0.60684 (14) | 0.0579 (7) | |
H18 | −0.4295 | 0.5298 | 0.6232 | 0.070* | |
C19 | −0.3648 (4) | 0.7108 (2) | 0.54919 (13) | 0.0539 (7) | |
H19 | −0.3857 | 0.7567 | 0.5190 | 0.065* | |
C20 | −0.2354 (4) | 0.70785 (19) | 0.59097 (13) | 0.0537 (7) | |
H20 | −0.1518 | 0.7518 | 0.5948 | 0.064* | |
C21 | 0.5865 (3) | 0.62539 (16) | 0.90388 (11) | 0.0377 (5) | |
H21A | 0.5461 | 0.6834 | 0.8876 | 0.045* | |
H21B | 0.5099 | 0.6054 | 0.9377 | 0.045* | |
C22 | 0.7582 (3) | 0.63864 (15) | 0.93302 (12) | 0.0409 (5) | |
C23 | 0.9047 (6) | 0.6673 (4) | 1.0301 (2) | 0.1045 (18) | |
H23A | 0.8845 | 0.6727 | 1.0760 | 0.157* | |
H23B | 0.9573 | 0.7220 | 1.0144 | 0.157* | |
H23C | 0.9770 | 0.6162 | 1.0221 | 0.157* | |
C24 | 0.6749 (4) | 0.4372 (2) | 0.93380 (13) | 0.0525 (6) | |
H24A | 0.6700 | 0.3736 | 0.9444 | 0.079* | |
H24B | 0.6321 | 0.4724 | 0.9696 | 0.079* | |
H24C | 0.7893 | 0.4543 | 0.9255 | 0.079* | |
C25 | 0.6328 (4) | 0.39005 (18) | 0.82026 (14) | 0.0530 (6) | |
H25A | 0.5990 | 0.3289 | 0.8307 | 0.079* | |
H25B | 0.7531 | 0.3931 | 0.8182 | 0.079* | |
H25C | 0.5863 | 0.4072 | 0.7789 | 0.079* | |
C26 | 0.4792 (3) | 0.67209 (16) | 0.76549 (12) | 0.0411 (5) | |
H26A | 0.4241 | 0.6756 | 0.7240 | 0.062* | |
H26B | 0.5971 | 0.6834 | 0.7600 | 0.062* | |
H26C | 0.4325 | 0.7170 | 0.7943 | 0.062* | |
C27 | 0.1257 (3) | 0.5937 (2) | 0.60509 (11) | 0.0473 (6) | |
H27A | 0.1526 | 0.6521 | 0.6233 | 0.071* | |
H27B | 0.0626 | 0.6019 | 0.5657 | 0.071* | |
H27C | 0.2275 | 0.5612 | 0.5956 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0551 (11) | 0.0791 (14) | 0.0376 (9) | −0.0112 (11) | −0.0024 (9) | 0.0142 (9) |
O2 | 0.0460 (9) | 0.0398 (8) | 0.0459 (8) | 0.0130 (8) | −0.0100 (8) | −0.0092 (7) |
O3 | 0.0607 (12) | 0.0374 (8) | 0.0654 (11) | 0.0095 (9) | −0.0170 (10) | −0.0152 (8) |
O4 | 0.0477 (10) | 0.0460 (9) | 0.0524 (9) | 0.0068 (8) | 0.0031 (8) | −0.0095 (8) |
O5 | 0.0605 (14) | 0.115 (2) | 0.0735 (15) | 0.0209 (16) | −0.0235 (12) | −0.0099 (15) |
O6 | 0.0365 (9) | 0.0694 (13) | 0.0766 (13) | −0.0076 (9) | 0.0001 (10) | −0.0141 (11) |
O7 | 0.0734 (14) | 0.0827 (15) | 0.0428 (9) | −0.0353 (13) | −0.0116 (10) | −0.0063 (9) |
O8 | 0.0376 (9) | 0.0617 (11) | 0.0561 (11) | −0.0122 (9) | 0.0038 (8) | 0.0099 (9) |
O9 | 0.0314 (7) | 0.0451 (8) | 0.0343 (7) | −0.0004 (7) | 0.0018 (6) | −0.0121 (6) |
C1 | 0.0329 (10) | 0.0286 (9) | 0.0291 (9) | −0.0005 (8) | 0.0023 (8) | −0.0029 (7) |
C2 | 0.0275 (9) | 0.0340 (10) | 0.0319 (9) | −0.0008 (8) | 0.0013 (8) | −0.0038 (8) |
C3 | 0.0362 (11) | 0.0331 (10) | 0.0360 (10) | 0.0008 (9) | −0.0037 (9) | 0.0006 (8) |
C4 | 0.0430 (12) | 0.0308 (9) | 0.0333 (10) | −0.0033 (9) | −0.0048 (9) | 0.0014 (8) |
C5 | 0.0331 (10) | 0.0365 (10) | 0.0349 (10) | −0.0049 (9) | −0.0027 (9) | 0.0028 (8) |
C6 | 0.0318 (10) | 0.0297 (9) | 0.0299 (9) | 0.0000 (8) | −0.0014 (8) | −0.0040 (7) |
C7 | 0.0325 (10) | 0.0302 (9) | 0.0346 (9) | 0.0006 (8) | −0.0026 (8) | −0.0022 (8) |
C8 | 0.0345 (10) | 0.0322 (9) | 0.0334 (9) | 0.0006 (8) | −0.0022 (9) | −0.0009 (8) |
C9 | 0.0365 (11) | 0.0310 (9) | 0.0389 (10) | 0.0022 (8) | −0.0063 (9) | −0.0043 (8) |
C10 | 0.0548 (14) | 0.0291 (9) | 0.0447 (11) | −0.0038 (10) | −0.0163 (11) | 0.0007 (9) |
C11 | 0.0524 (14) | 0.0370 (11) | 0.0468 (12) | 0.0066 (11) | −0.0092 (11) | −0.0107 (10) |
C12 | 0.0745 (19) | 0.0511 (14) | 0.0473 (13) | 0.0182 (14) | −0.0175 (14) | −0.0188 (11) |
C13 | 0.0501 (14) | 0.0436 (12) | 0.0448 (12) | 0.0044 (11) | −0.0175 (11) | −0.0093 (10) |
C14 | 0.0372 (11) | 0.0355 (10) | 0.0328 (9) | 0.0042 (9) | −0.0043 (9) | −0.0043 (8) |
C15 | 0.0345 (10) | 0.0415 (11) | 0.0364 (10) | 0.0016 (9) | −0.0022 (9) | −0.0018 (9) |
C16 | 0.0400 (11) | 0.0330 (10) | 0.0393 (11) | 0.0044 (9) | −0.0028 (10) | −0.0031 (9) |
C17 | 0.0370 (11) | 0.0519 (13) | 0.0399 (11) | 0.0091 (11) | −0.0013 (10) | −0.0062 (10) |
C18 | 0.0403 (13) | 0.0752 (19) | 0.0584 (16) | 0.0004 (13) | −0.0068 (12) | 0.0011 (14) |
C19 | 0.0569 (16) | 0.0574 (15) | 0.0475 (13) | 0.0195 (14) | −0.0149 (13) | 0.0008 (11) |
C20 | 0.0604 (16) | 0.0499 (13) | 0.0509 (14) | 0.0132 (13) | −0.0118 (14) | −0.0016 (11) |
C21 | 0.0346 (10) | 0.0408 (11) | 0.0379 (10) | −0.0014 (9) | 0.0002 (9) | −0.0097 (9) |
C22 | 0.0421 (13) | 0.0334 (10) | 0.0473 (12) | −0.0076 (10) | −0.0056 (11) | −0.0042 (9) |
C23 | 0.113 (4) | 0.124 (4) | 0.076 (2) | −0.071 (3) | −0.053 (3) | 0.022 (2) |
C24 | 0.0473 (14) | 0.0549 (14) | 0.0554 (14) | −0.0043 (12) | −0.0184 (12) | 0.0130 (12) |
C25 | 0.0540 (15) | 0.0404 (12) | 0.0646 (16) | 0.0093 (12) | 0.0039 (13) | −0.0078 (12) |
C26 | 0.0438 (12) | 0.0363 (11) | 0.0432 (12) | −0.0018 (10) | 0.0031 (10) | 0.0057 (10) |
C27 | 0.0441 (13) | 0.0621 (15) | 0.0358 (11) | 0.0069 (12) | 0.0034 (10) | 0.0052 (11) |
Geometric parameters (Å, º) top
O1—C4 | 1.207 (3) | C11—C12 | 1.497 (3) |
O2—C16 | 1.348 (3) | C11—H11 | 0.98 |
O2—C15 | 1.452 (3) | C12—C13 | 1.518 (4) |
O3—C16 | 1.211 (3) | C12—H12A | 0.97 |
O4—C11 | 1.460 (3) | C12—H12B | 0.97 |
O4—C9 | 1.461 (3) | C13—C14 | 1.540 (3) |
O5—C18 | 1.351 (4) | C13—H13A | 0.97 |
O5—C19 | 1.389 (4) | C13—H13B | 0.97 |
O6—C22 | 1.196 (3) | C14—C15 | 1.528 (3) |
O7—C22 | 1.333 (3) | C14—C27 | 1.535 (3) |
O7—C23 | 1.433 (4) | C15—C17 | 1.499 (3) |
O8—C5 | 1.420 (3) | C15—H15 | 0.98 |
O8—H8 | 0.82 | C17—C18 | 1.367 (4) |
O9—C6 | 1.414 (2) | C17—C20 | 1.402 (4) |
O9—H9 | 0.82 | C18—H18 | 0.93 |
C1—C26 | 1.528 (3) | C19—C20 | 1.342 (4) |
C1—C6 | 1.553 (3) | C19—H19 | 0.93 |
C1—C2 | 1.553 (3) | C20—H20 | 0.93 |
C1—H1 | 0.98 | C21—C22 | 1.506 (3) |
C2—C21 | 1.536 (3) | C21—H21A | 0.97 |
C2—C3 | 1.559 (3) | C21—H21B | 0.97 |
C2—H2 | 0.98 | C23—H23A | 0.96 |
C3—C24 | 1.530 (3) | C23—H23B | 0.96 |
C3—C4 | 1.530 (3) | C23—H23C | 0.96 |
C3—C25 | 1.537 (3) | C24—H24A | 0.96 |
C4—C5 | 1.540 (3) | C24—H24B | 0.96 |
C5—C10 | 1.536 (3) | C24—H24C | 0.96 |
C5—C6 | 1.569 (3) | C25—H25A | 0.96 |
C6—C7 | 1.528 (3) | C25—H25B | 0.96 |
C7—C8 | 1.338 (3) | C25—H25C | 0.96 |
C7—C16 | 1.492 (3) | C26—H26A | 0.96 |
C8—C9 | 1.490 (3) | C26—H26B | 0.96 |
C8—C14 | 1.518 (3) | C26—H26C | 0.96 |
C9—C11 | 1.467 (3) | C27—H27A | 0.96 |
C9—C10 | 1.499 (3) | C27—H27B | 0.96 |
C10—H10A | 0.97 | C27—H27C | 0.96 |
C10—H10B | 0.97 | | |
| | | |
C16—O2—C15 | 120.11 (17) | C14—C13—H13A | 109.0 |
C11—O4—C9 | 60.31 (15) | C12—C13—H13B | 109.0 |
C18—O5—C19 | 107.2 (2) | C14—C13—H13B | 109.0 |
C22—O7—C23 | 116.1 (3) | H13A—C13—H13B | 107.8 |
C5—O8—H8 | 109.5 | C8—C14—C15 | 105.50 (17) |
C6—O9—H9 | 109.5 | C8—C14—C27 | 109.46 (19) |
C26—C1—C6 | 111.82 (18) | C15—C14—C27 | 111.56 (19) |
C26—C1—C2 | 111.91 (18) | C8—C14—C13 | 110.12 (19) |
C6—C1—C2 | 113.02 (16) | C15—C14—C13 | 108.7 (2) |
C26—C1—H1 | 106.5 | C27—C14—C13 | 111.4 (2) |
C6—C1—H1 | 106.5 | O2—C15—C17 | 106.07 (18) |
C2—C1—H1 | 106.5 | O2—C15—C14 | 110.68 (18) |
C21—C2—C1 | 113.56 (17) | C17—C15—C14 | 115.11 (18) |
C21—C2—C3 | 112.63 (17) | O2—C15—H15 | 108.3 |
C1—C2—C3 | 111.78 (17) | C17—C15—H15 | 108.3 |
C21—C2—H2 | 106.1 | C14—C15—H15 | 108.3 |
C1—C2—H2 | 106.1 | O3—C16—O2 | 117.2 (2) |
C3—C2—H2 | 106.1 | O3—C16—C7 | 124.9 (2) |
C24—C3—C4 | 108.2 (2) | O2—C16—C7 | 117.81 (19) |
C24—C3—C25 | 106.4 (2) | C18—C17—C20 | 105.7 (3) |
C4—C3—C25 | 114.1 (2) | C18—C17—C15 | 126.3 (3) |
C24—C3—C2 | 112.77 (19) | C20—C17—C15 | 128.0 (2) |
C4—C3—C2 | 106.34 (17) | O5—C18—C17 | 110.1 (3) |
C25—C3—C2 | 109.23 (19) | O5—C18—H18 | 124.9 |
O1—C4—C3 | 121.6 (2) | C17—C18—H18 | 124.9 |
O1—C4—C5 | 117.8 (2) | C20—C19—O5 | 108.2 (3) |
C3—C4—C5 | 120.42 (18) | C20—C19—H19 | 125.9 |
O8—C5—C10 | 106.3 (2) | O5—C19—H19 | 125.9 |
O8—C5—C4 | 108.78 (17) | C19—C20—C17 | 108.8 (3) |
C10—C5—C4 | 113.04 (19) | C19—C20—H20 | 125.6 |
O8—C5—C6 | 107.52 (18) | C17—C20—H20 | 125.6 |
C10—C5—C6 | 113.87 (17) | C22—C21—C2 | 113.00 (19) |
C4—C5—C6 | 107.14 (17) | C22—C21—H21A | 109.0 |
O9—C6—C7 | 113.77 (17) | C2—C21—H21A | 109.0 |
O9—C6—C1 | 108.00 (16) | C22—C21—H21B | 109.0 |
C7—C6—C1 | 110.65 (16) | C2—C21—H21B | 109.0 |
O9—C6—C5 | 106.28 (16) | H21A—C21—H21B | 107.8 |
C7—C6—C5 | 107.82 (16) | O6—C22—O7 | 124.0 (3) |
C1—C6—C5 | 110.23 (16) | O6—C22—C21 | 124.8 (2) |
C8—C7—C16 | 118.46 (19) | O7—C22—C21 | 111.1 (2) |
C8—C7—C6 | 121.30 (18) | O7—C23—H23A | 109.5 |
C16—C7—C6 | 119.98 (18) | O7—C23—H23B | 109.5 |
C7—C8—C9 | 119.33 (19) | H23A—C23—H23B | 109.5 |
C7—C8—C14 | 121.23 (19) | O7—C23—H23C | 109.5 |
C9—C8—C14 | 119.41 (18) | H23A—C23—H23C | 109.5 |
O4—C9—C11 | 59.82 (16) | H23B—C23—H23C | 109.5 |
O4—C9—C8 | 113.30 (18) | C3—C24—H24A | 109.5 |
C11—C9—C8 | 119.39 (19) | C3—C24—H24B | 109.5 |
O4—C9—C10 | 117.3 (2) | H24A—C24—H24B | 109.5 |
C11—C9—C10 | 118.81 (19) | C3—C24—H24C | 109.5 |
C8—C9—C10 | 115.93 (18) | H24A—C24—H24C | 109.5 |
C9—C10—C5 | 116.50 (18) | H24B—C24—H24C | 109.5 |
C9—C10—H10A | 108.2 | C3—C25—H25A | 109.5 |
C5—C10—H10A | 108.2 | C3—C25—H25B | 109.5 |
C9—C10—H10B | 108.2 | H25A—C25—H25B | 109.5 |
C5—C10—H10B | 108.2 | C3—C25—H25C | 109.5 |
H10A—C10—H10B | 107.3 | H25A—C25—H25C | 109.5 |
O4—C11—C9 | 59.87 (14) | H25B—C25—H25C | 109.5 |
O4—C11—C12 | 118.3 (2) | C1—C26—H26A | 109.5 |
C9—C11—C12 | 120.9 (2) | C1—C26—H26B | 109.5 |
O4—C11—H11 | 115.4 | H26A—C26—H26B | 109.5 |
C9—C11—H11 | 115.4 | C1—C26—H26C | 109.5 |
C12—C11—H11 | 115.4 | H26A—C26—H26C | 109.5 |
C11—C12—C13 | 111.3 (2) | H26B—C26—H26C | 109.5 |
C11—C12—H12A | 109.4 | C14—C27—H27A | 109.5 |
C13—C12—H12A | 109.4 | C14—C27—H27B | 109.5 |
C11—C12—H12B | 109.4 | H27A—C27—H27B | 109.5 |
C13—C12—H12B | 109.4 | C14—C27—H27C | 109.5 |
H12A—C12—H12B | 108.0 | H27A—C27—H27C | 109.5 |
C12—C13—C14 | 113.0 (2) | H27B—C27—H27C | 109.5 |
C12—C13—H13A | 109.0 | | |
| | | |
C26—C1—C2—C21 | 56.5 (2) | O4—C9—C10—C5 | 112.6 (2) |
C6—C1—C2—C21 | −70.8 (2) | C11—C9—C10—C5 | −178.5 (2) |
C26—C1—C2—C3 | −174.73 (18) | C8—C9—C10—C5 | −25.6 (3) |
C6—C1—C2—C3 | 58.0 (2) | O8—C5—C10—C9 | 103.5 (2) |
C21—C2—C3—C24 | −40.9 (3) | C4—C5—C10—C9 | −137.2 (2) |
C1—C2—C3—C24 | −170.1 (2) | C6—C5—C10—C9 | −14.6 (3) |
C21—C2—C3—C4 | 77.5 (2) | C9—O4—C11—C12 | 111.2 (2) |
C1—C2—C3—C4 | −51.7 (2) | C8—C9—C11—O4 | 101.4 (2) |
C21—C2—C3—C25 | −158.9 (2) | C10—C9—C11—O4 | −106.6 (2) |
C1—C2—C3—C25 | 71.8 (2) | O4—C9—C11—C12 | −107.0 (3) |
C24—C3—C4—O1 | 1.0 (3) | C8—C9—C11—C12 | −5.6 (4) |
C25—C3—C4—O1 | 119.2 (3) | C10—C9—C11—C12 | 146.4 (3) |
C2—C3—C4—O1 | −120.4 (2) | O4—C11—C12—C13 | −92.7 (3) |
C24—C3—C4—C5 | 175.9 (2) | C9—C11—C12—C13 | −22.7 (4) |
C25—C3—C4—C5 | −65.9 (3) | C11—C12—C13—C14 | 54.3 (3) |
C2—C3—C4—C5 | 54.6 (2) | C7—C8—C14—C15 | −38.2 (3) |
O1—C4—C5—O8 | 3.9 (3) | C9—C8—C14—C15 | 143.9 (2) |
C3—C4—C5—O8 | −171.21 (19) | C7—C8—C14—C27 | 81.9 (3) |
O1—C4—C5—C10 | −113.9 (2) | C9—C8—C14—C27 | −96.0 (2) |
C3—C4—C5—C10 | 71.0 (3) | C7—C8—C14—C13 | −155.3 (2) |
O1—C4—C5—C6 | 119.9 (2) | C9—C8—C14—C13 | 26.8 (3) |
C3—C4—C5—C6 | −55.3 (2) | C12—C13—C14—C8 | −56.2 (3) |
C26—C1—C6—O9 | −69.1 (2) | C12—C13—C14—C15 | −171.3 (2) |
C2—C1—C6—O9 | 58.3 (2) | C12—C13—C14—C27 | 65.4 (3) |
C26—C1—C6—C7 | 56.1 (2) | C16—O2—C15—C17 | −167.6 (2) |
C2—C1—C6—C7 | −176.58 (16) | C16—O2—C15—C14 | −42.1 (3) |
C26—C1—C6—C5 | 175.23 (17) | C8—C14—C15—O2 | 56.4 (2) |
C2—C1—C6—C5 | −57.4 (2) | C27—C14—C15—O2 | −62.3 (2) |
O8—C5—C6—O9 | 51.9 (2) | C13—C14—C15—O2 | 174.48 (18) |
C10—C5—C6—O9 | 169.34 (19) | C8—C14—C15—C17 | 176.7 (2) |
C4—C5—C6—O9 | −64.9 (2) | C27—C14—C15—C17 | 57.9 (3) |
O8—C5—C6—C7 | −70.4 (2) | C13—C14—C15—C17 | −65.3 (3) |
C10—C5—C6—C7 | 47.0 (2) | C15—O2—C16—O3 | −179.0 (2) |
C4—C5—C6—C7 | 172.77 (17) | C15—O2—C16—C7 | 2.6 (3) |
O8—C5—C6—C1 | 168.67 (16) | C8—C7—C16—O3 | −158.8 (3) |
C10—C5—C6—C1 | −73.9 (2) | C6—C7—C16—O3 | 15.4 (4) |
C4—C5—C6—C1 | 51.9 (2) | C8—C7—C16—O2 | 19.3 (3) |
O9—C6—C7—C8 | −162.1 (2) | C6—C7—C16—O2 | −166.4 (2) |
C1—C6—C7—C8 | 76.1 (2) | O2—C15—C17—C18 | −144.0 (3) |
C5—C6—C7—C8 | −44.5 (3) | C14—C15—C17—C18 | 93.3 (3) |
O9—C6—C7—C16 | 23.8 (3) | O2—C15—C17—C20 | 36.7 (3) |
C1—C6—C7—C16 | −98.0 (2) | C14—C15—C17—C20 | −86.0 (3) |
C5—C6—C7—C16 | 141.4 (2) | C19—O5—C18—C17 | −0.8 (3) |
C16—C7—C8—C9 | 179.3 (2) | C20—C17—C18—O5 | 1.1 (3) |
C6—C7—C8—C9 | 5.1 (3) | C15—C17—C18—O5 | −178.3 (2) |
C16—C7—C8—C14 | 1.4 (3) | C18—O5—C19—C20 | 0.1 (3) |
C6—C7—C8—C14 | −172.77 (19) | O5—C19—C20—C17 | 0.5 (3) |
C11—O4—C9—C8 | −111.6 (2) | C18—C17—C20—C19 | −1.0 (3) |
C11—O4—C9—C10 | 109.1 (2) | C15—C17—C20—C19 | 178.4 (2) |
C7—C8—C9—O4 | −107.5 (2) | C1—C2—C21—C22 | −147.41 (19) |
C14—C8—C9—O4 | 70.4 (3) | C3—C2—C21—C22 | 84.2 (2) |
C7—C8—C9—C11 | −174.8 (2) | C23—O7—C22—O6 | −3.7 (5) |
C14—C8—C9—C11 | 3.1 (3) | C23—O7—C22—C21 | 179.7 (3) |
C7—C8—C9—C10 | 32.4 (3) | C2—C21—C22—O6 | 38.4 (3) |
C14—C8—C9—C10 | −149.7 (2) | C2—C21—C22—O7 | −145.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O1 | 0.82 | 2.07 | 2.575 (3) | 119 |
O9—H9···O6i | 0.82 | 2.09 | 2.910 (2) | 174 |
C2—H2···O6 | 0.98 | 2.47 | 2.926 (3) | 108 |
C18—H18···O4i | 0.93 | 2.58 | 3.452 (3) | 157 |
C19—H19···O1ii | 0.93 | 2.55 | 3.096 (4) | 118 |
C27—H27A···O2 | 0.96 | 2.60 | 2.977 (3) | 104 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+3/2. |