The title compound, C
32H
48O
5, isolated from the leaves of
Miconia macrothyrsa, is a pentacyclic triterpene, in which rings A, B, D and E take a chair conformation, while ring C has a half-chair conformation. Rings A and B and rings B and C are
trans-fused, while rings D and E are
cis-fused. In the crystal structure, there are intermolecular O—H
O hydrogen bonds and intramolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 627806
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.127
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C3 .. 23.25 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O4 - C31 .. 9.80 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 - C11 .. 10.15 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C20 - C29 .. 7.18 su
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.61 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C28 .. 6.98 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 5.19 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C32 H48 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 30.00
From the CIF: _reflns_number_total 4656
Count of symmetry unique reflns 4699
Completeness (_total/calc) 99.08%
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 C5 = . S
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 C14 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21 = . R
0 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
9 ALERT level G = General alerts; check
8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
8 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
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
21-
α-acetoxy-3-oxo-olean-12-en-28-oic acid
top
Crystal data top
C32H48O5 | Dx = 1.187 Mg m−3 |
Mr = 512.7 | Melting point: 283 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 78 reflections |
a = 7.3696 (2) Å | θ = 20.0–25.0° |
b = 18.6464 (6) Å | µ = 0.08 mm−1 |
c = 20.8708 (7) Å | T = 298 K |
V = 2867.99 (15) Å3 | Prism, white |
Z = 4 | 0.50 × 0.40 × 0.30 mm |
F(000) = 1120 | |
Data collection top
Siemens P4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 1.5° |
Graphite monochromator | h = −1→10 |
ω scans | k = −1→26 |
5957 measured reflections | l = −1→29 |
4656 independent reflections | 3 standard reflections every 300 reflections |
3621 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.3781P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4656 reflections | Δρmax = 0.30 e Å−3 |
343 parameters | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | 0.1415 (4) | 0.18525 (14) | 1.06205 (10) | 0.0633 (7) | |
O2 | 0.5130 (3) | −0.24360 (15) | 0.71034 (12) | 0.0686 (7) | |
O3 | 0.2294 (3) | −0.24074 (15) | 0.67693 (9) | 0.0632 (7) | |
H3 | 0.2758 | −0.2217 | 0.6455 | 0.076* | |
O4 | 0.3039 (3) | −0.49024 (9) | 0.80825 (9) | 0.0435 (5) | |
O5 | 0.0353 (4) | −0.52264 (14) | 0.85085 (16) | 0.0804 (9) | |
C1 | 0.4153 (4) | 0.04838 (13) | 0.99277 (12) | 0.0365 (5) | |
H1A | 0.5431 | 0.0361 | 0.9911 | 0.044* | |
H1B | 0.3567 | 0.0153 | 1.0221 | 0.044* | |
C2 | 0.3956 (4) | 0.12526 (13) | 1.01912 (14) | 0.0425 (6) | |
H2A | 0.4387 | 0.1263 | 1.0630 | 0.051* | |
H2B | 0.4719 | 0.1572 | 0.9942 | 0.051* | |
C3 | 0.2049 (4) | 0.15223 (13) | 1.01733 (11) | 0.0362 (5) | |
C4 | 0.0945 (3) | 0.14065 (12) | 0.95611 (11) | 0.0313 (5) | |
C5 | 0.1309 (3) | 0.06343 (11) | 0.92937 (10) | 0.0254 (4) | |
H5A | 0.0755 | 0.0313 | 0.9609 | 0.031* | |
C6 | 0.0319 (4) | 0.04686 (13) | 0.86683 (11) | 0.0332 (5) | |
H6A | 0.0948 | 0.0696 | 0.8314 | 0.040* | |
H6B | −0.0902 | 0.0662 | 0.8686 | 0.040* | |
C7 | 0.0237 (3) | −0.03422 (12) | 0.85580 (12) | 0.0330 (5) | |
H7A | −0.0374 | −0.0434 | 0.8155 | 0.040* | |
H7B | −0.0484 | −0.0558 | 0.8896 | 0.040* | |
C8 | 0.2109 (3) | −0.07059 (12) | 0.85436 (10) | 0.0263 (4) | |
C9 | 0.3282 (3) | −0.04449 (11) | 0.91162 (11) | 0.0280 (4) | |
H9A | 0.2727 | −0.0661 | 0.9497 | 0.034* | |
C10 | 0.3325 (3) | 0.03878 (11) | 0.92557 (11) | 0.0277 (4) | |
C11 | 0.5193 (4) | −0.07752 (15) | 0.90751 (17) | 0.0485 (7) | |
H11A | 0.5939 | −0.0477 | 0.8800 | 0.058* | |
H11B | 0.5732 | −0.0773 | 0.9499 | 0.058* | |
C12 | 0.5213 (3) | −0.15305 (14) | 0.88208 (13) | 0.0394 (6) | |
H12A | 0.6324 | −0.1767 | 0.8818 | 0.047* | |
C13 | 0.3790 (3) | −0.18889 (12) | 0.86000 (11) | 0.0291 (5) | |
C14 | 0.1893 (3) | −0.15532 (12) | 0.86112 (10) | 0.0277 (4) | |
C15 | 0.0689 (3) | −0.18494 (13) | 0.80686 (12) | 0.0341 (5) | |
H15A | −0.0568 | −0.1740 | 0.8167 | 0.041* | |
H15B | 0.0995 | −0.1602 | 0.7674 | 0.041* | |
C16 | 0.0862 (4) | −0.26571 (13) | 0.79562 (11) | 0.0334 (5) | |
H16A | 0.0102 | −0.2794 | 0.7597 | 0.040* | |
H16B | 0.0429 | −0.2911 | 0.8332 | 0.040* | |
C17 | 0.2829 (3) | −0.28822 (12) | 0.78183 (10) | 0.0296 (5) | |
C18 | 0.4064 (4) | −0.26668 (12) | 0.83858 (10) | 0.0312 (5) | |
H18A | 0.5318 | −0.2703 | 0.8232 | 0.037* | |
C19 | 0.3896 (5) | −0.31830 (12) | 0.89564 (11) | 0.0409 (6) | |
H19A | 0.2690 | −0.3137 | 0.9138 | 0.049* | |
H19B | 0.4760 | −0.3041 | 0.9283 | 0.049* | |
C20 | 0.4227 (5) | −0.39765 (14) | 0.87861 (13) | 0.0459 (7) | |
C21 | 0.2809 (4) | −0.41601 (12) | 0.82782 (11) | 0.0358 (5) | |
H21A | 0.1595 | −0.4099 | 0.8462 | 0.043* | |
C22 | 0.2967 (4) | −0.37002 (12) | 0.76818 (10) | 0.0345 (5) | |
H22A | 0.2013 | −0.3835 | 0.7385 | 0.041* | |
H22B | 0.4121 | −0.3798 | 0.7476 | 0.041* | |
C23 | 0.1462 (5) | 0.20237 (13) | 0.90978 (13) | 0.0445 (6) | |
H23A | 0.1068 | 0.2473 | 0.9275 | 0.067* | |
H23B | 0.0884 | 0.1948 | 0.8691 | 0.067* | |
H23C | 0.2755 | 0.2032 | 0.9041 | 0.067* | |
C24 | −0.1079 (4) | 0.14812 (16) | 0.97238 (16) | 0.0475 (7) | |
H24A | −0.1282 | 0.1929 | 0.9939 | 0.071* | |
H24B | −0.1441 | 0.1093 | 0.9998 | 0.071* | |
H24C | −0.1780 | 0.1468 | 0.9336 | 0.071* | |
C25 | 0.4452 (4) | 0.08140 (14) | 0.87680 (14) | 0.0411 (6) | |
H25A | 0.4818 | 0.1262 | 0.8955 | 0.062* | |
H25B | 0.3734 | 0.0904 | 0.8393 | 0.062* | |
H25C | 0.5509 | 0.0542 | 0.8652 | 0.062* | |
C26 | 0.3007 (4) | −0.05230 (14) | 0.78939 (12) | 0.0415 (6) | |
H26A | 0.3054 | −0.0012 | 0.7842 | 0.062* | |
H26B | 0.2309 | −0.0729 | 0.7552 | 0.062* | |
H26C | 0.4216 | −0.0714 | 0.7885 | 0.062* | |
C27 | 0.0974 (4) | −0.17749 (13) | 0.92503 (12) | 0.0367 (5) | |
H27A | 0.0658 | −0.2274 | 0.9234 | 0.055* | |
H27B | −0.0103 | −0.1494 | 0.9313 | 0.055* | |
H27C | 0.1798 | −0.1694 | 0.9599 | 0.055* | |
C28 | 0.3558 (4) | −0.25362 (12) | 0.72042 (11) | 0.0369 (6) | |
C29 | 0.3853 (7) | −0.44313 (16) | 0.93883 (15) | 0.0748 (13) | |
H29A | 0.4609 | −0.4268 | 0.9733 | 0.112* | |
H29B | 0.4115 | −0.4926 | 0.9299 | 0.112* | |
H29C | 0.2601 | −0.4384 | 0.9508 | 0.112* | |
C30 | 0.6168 (5) | −0.41052 (18) | 0.8555 (2) | 0.0652 (10) | |
H30A | 0.6382 | −0.3833 | 0.8172 | 0.098* | |
H30B | 0.6335 | −0.4606 | 0.8466 | 0.098* | |
H30C | 0.7007 | −0.3958 | 0.8881 | 0.098* | |
C31 | 0.1769 (5) | −0.53812 (15) | 0.82665 (14) | 0.0466 (7) | |
C32 | 0.2417 (6) | −0.61275 (15) | 0.81459 (18) | 0.0621 (9) | |
H32A | 0.1432 | −0.6457 | 0.8205 | 0.093* | |
H32B | 0.3377 | −0.6241 | 0.8440 | 0.093* | |
H32C | 0.2861 | −0.6164 | 0.7715 | 0.093* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0682 (15) | 0.0794 (15) | 0.0425 (10) | −0.0279 (11) | −0.0025 (11) | 0.0104 (14) |
O2 | 0.0541 (14) | 0.0976 (19) | 0.0540 (12) | 0.0222 (13) | 0.0108 (12) | −0.0200 (14) |
O3 | 0.0619 (14) | 0.0977 (19) | 0.0301 (9) | 0.0190 (11) | −0.0025 (10) | −0.0081 (14) |
O4 | 0.0586 (13) | 0.0282 (8) | 0.0437 (9) | −0.0064 (7) | 0.0089 (10) | −0.0007 (9) |
O5 | 0.0725 (18) | 0.0582 (14) | 0.111 (2) | 0.0013 (15) | 0.0310 (18) | −0.0116 (14) |
C1 | 0.0384 (13) | 0.0319 (11) | 0.0391 (12) | −0.0078 (9) | −0.0140 (11) | 0.0021 (11) |
C2 | 0.0458 (15) | 0.0336 (12) | 0.0481 (14) | −0.0135 (11) | −0.0170 (13) | 0.0010 (12) |
C3 | 0.0461 (14) | 0.0300 (11) | 0.0323 (10) | −0.0062 (9) | −0.0024 (11) | −0.0039 (11) |
C4 | 0.0332 (12) | 0.0267 (9) | 0.0340 (11) | −0.0051 (8) | −0.0028 (10) | 0.0010 (9) |
C5 | 0.0259 (10) | 0.0230 (9) | 0.0275 (9) | −0.0014 (8) | 0.0003 (8) | 0.0001 (8) |
C6 | 0.0326 (11) | 0.0345 (11) | 0.0324 (11) | −0.0048 (9) | −0.0079 (10) | 0.0070 (10) |
C7 | 0.0288 (11) | 0.0357 (11) | 0.0346 (11) | −0.0086 (9) | −0.0089 (10) | 0.0008 (10) |
C8 | 0.0240 (10) | 0.0287 (10) | 0.0261 (9) | −0.0058 (8) | 0.0003 (9) | −0.0005 (8) |
C9 | 0.0247 (10) | 0.0258 (9) | 0.0334 (10) | −0.0060 (8) | −0.0044 (9) | 0.0018 (9) |
C10 | 0.0255 (10) | 0.0245 (9) | 0.0331 (10) | −0.0036 (8) | −0.0021 (9) | −0.0007 (9) |
C11 | 0.0292 (12) | 0.0394 (13) | 0.0769 (19) | −0.0212 (14) | −0.0140 (14) | 0.0039 (11) |
C12 | 0.0259 (11) | 0.0364 (12) | 0.0559 (15) | −0.0134 (11) | −0.0045 (12) | 0.0052 (10) |
C13 | 0.0314 (11) | 0.0283 (10) | 0.0276 (10) | −0.0061 (8) | −0.0010 (9) | 0.0012 (9) |
C14 | 0.0258 (10) | 0.0289 (10) | 0.0283 (9) | −0.0051 (8) | 0.0011 (9) | −0.0002 (9) |
C15 | 0.0275 (11) | 0.0360 (11) | 0.0389 (12) | −0.0087 (10) | −0.0061 (10) | 0.0004 (10) |
C16 | 0.0346 (12) | 0.0350 (11) | 0.0305 (10) | −0.0074 (9) | −0.0002 (10) | −0.0053 (10) |
C17 | 0.0373 (12) | 0.0289 (10) | 0.0227 (9) | −0.0038 (8) | 0.0018 (9) | −0.0029 (10) |
C18 | 0.0348 (11) | 0.0301 (10) | 0.0286 (10) | −0.0070 (8) | −0.0010 (10) | 0.0029 (10) |
C19 | 0.0631 (18) | 0.0329 (11) | 0.0267 (10) | −0.0044 (9) | −0.0075 (12) | 0.0045 (13) |
C20 | 0.070 (2) | 0.0320 (11) | 0.0355 (12) | −0.0024 (10) | −0.0108 (14) | 0.0081 (13) |
C21 | 0.0502 (15) | 0.0268 (10) | 0.0304 (10) | −0.0046 (8) | 0.0055 (11) | −0.0009 (11) |
C22 | 0.0478 (14) | 0.0302 (10) | 0.0255 (9) | −0.0066 (8) | 0.0028 (10) | −0.0028 (11) |
C23 | 0.0614 (18) | 0.0267 (10) | 0.0454 (14) | 0.0024 (10) | −0.0031 (14) | 0.0016 (12) |
C24 | 0.0369 (14) | 0.0435 (14) | 0.0620 (17) | −0.0164 (13) | 0.0017 (14) | 0.0067 (12) |
C25 | 0.0347 (13) | 0.0375 (12) | 0.0510 (14) | −0.0029 (11) | 0.0121 (12) | −0.0061 (11) |
C26 | 0.0512 (16) | 0.0394 (12) | 0.0341 (11) | −0.0038 (10) | 0.0109 (12) | −0.0045 (12) |
C27 | 0.0404 (13) | 0.0330 (11) | 0.0366 (11) | −0.0055 (9) | 0.0083 (11) | −0.0039 (11) |
C28 | 0.0497 (15) | 0.0311 (11) | 0.0299 (11) | −0.0032 (9) | 0.0054 (11) | −0.0048 (11) |
C29 | 0.144 (4) | 0.0403 (14) | 0.0397 (14) | 0.0066 (12) | −0.023 (2) | 0.001 (2) |
C30 | 0.060 (2) | 0.0503 (17) | 0.085 (2) | −0.0188 (17) | −0.020 (2) | 0.0180 (16) |
C31 | 0.0609 (19) | 0.0362 (13) | 0.0427 (14) | 0.0002 (11) | −0.0036 (15) | −0.0063 (14) |
C32 | 0.081 (2) | 0.0331 (13) | 0.072 (2) | −0.0019 (14) | −0.014 (2) | −0.0052 (16) |
Geometric parameters (Å, º) top
O1—C3 | 1.212 (3) | C2—H2B | 0.9701 |
O2—C28 | 1.192 (4) | C5—H5A | 0.9800 |
O3—C28 | 1.323 (3) | C6—H6A | 0.9703 |
O4—C21 | 1.453 (3) | C6—H6B | 0.9697 |
O4—C31 | 1.349 (4) | C7—H7A | 0.9700 |
O5—C31 | 1.195 (5) | C7—H7B | 0.9701 |
O3—H3 | 0.8201 | C9—H9A | 0.9801 |
C1—C2 | 1.542 (3) | C11—H11A | 0.9697 |
C1—C10 | 1.540 (3) | C11—H11B | 0.9699 |
C2—C3 | 1.493 (4) | C12—H12A | 0.9300 |
C3—C4 | 1.530 (3) | C15—H15A | 0.9702 |
C4—C23 | 1.551 (3) | C15—H15B | 0.9698 |
C4—C24 | 1.536 (4) | C16—H16A | 0.9701 |
C4—C5 | 1.567 (3) | C16—H16B | 0.9700 |
C5—C10 | 1.557 (3) | C18—H18A | 0.9803 |
C5—C6 | 1.527 (3) | C19—H19A | 0.9700 |
C6—C7 | 1.531 (3) | C19—H19B | 0.9699 |
C7—C8 | 1.538 (3) | C21—H21A | 0.9800 |
C8—C9 | 1.553 (3) | C22—H22A | 0.9701 |
C8—C14 | 1.594 (3) | C22—H22B | 0.9696 |
C8—C26 | 1.547 (3) | C23—H23A | 0.9599 |
C9—C11 | 1.540 (4) | C23—H23B | 0.9599 |
C9—C10 | 1.580 (3) | C23—H23C | 0.9601 |
C10—C25 | 1.535 (4) | C24—H24A | 0.9601 |
C11—C12 | 1.505 (4) | C24—H24B | 0.9601 |
C12—C13 | 1.326 (3) | C24—H24C | 0.9602 |
C13—C14 | 1.532 (3) | C25—H25A | 0.9599 |
C13—C18 | 1.531 (3) | C25—H25B | 0.9600 |
C14—C27 | 1.552 (3) | C25—H25C | 0.9599 |
C14—C15 | 1.541 (3) | C26—H26A | 0.9600 |
C15—C16 | 1.530 (3) | C26—H26B | 0.9599 |
C16—C17 | 1.536 (3) | C26—H26C | 0.9601 |
C17—C22 | 1.555 (3) | C27—H27A | 0.9601 |
C17—C28 | 1.532 (3) | C27—H27B | 0.9601 |
C17—C18 | 1.547 (3) | C27—H27C | 0.9599 |
C18—C19 | 1.536 (3) | C29—H29A | 0.9599 |
C19—C20 | 1.541 (4) | C29—H29B | 0.9599 |
C20—C21 | 1.527 (4) | C29—H29C | 0.9602 |
C20—C29 | 1.541 (4) | C30—H30A | 0.9603 |
C20—C30 | 1.529 (5) | C30—H30B | 0.9600 |
C21—C22 | 1.516 (3) | C30—H30C | 0.9598 |
C31—C32 | 1.493 (4) | C32—H32A | 0.9599 |
C1—H1A | 0.9699 | C32—H32B | 0.9602 |
C1—H1B | 0.9701 | C32—H32C | 0.9602 |
C2—H2A | 0.9702 | | |
| | | |
O1···O3i | 2.779 (3) | C25···C26 | 3.268 (4) |
O2···C32ii | 3.081 (4) | C25···C23 | 3.228 (4) |
O3···C15 | 3.136 (3) | C26···C25 | 3.268 (4) |
O5···C1iii | 3.415 (4) | C26···C12 | 3.149 (4) |
O1···H3i | 1.9668 | C27···C19 | 3.451 (4) |
C12···C26 | 3.149 (4) | C29···C31 | 3.313 (5) |
C19···C27 | 3.451 (4) | C31···C29 | 3.313 (5) |
C23···C25 | 3.228 (4) | | |
| | | |
C21—O4—C31 | 118.0 (2) | C6—C7—H7A | 108.80 |
C28—O3—H3 | 109.48 | C6—C7—H7B | 108.80 |
C2—C1—C10 | 113.3 (2) | C8—C7—H7A | 108.81 |
C1—C2—C3 | 113.1 (2) | C8—C7—H7B | 108.80 |
O1—C3—C2 | 121.0 (3) | H7A—C7—H7B | 107.68 |
O1—C3—C4 | 120.7 (3) | C8—C9—H9A | 105.22 |
C2—C3—C4 | 118.3 (2) | C10—C9—H9A | 105.23 |
C3—C4—C5 | 109.63 (18) | C11—C9—H9A | 105.24 |
C3—C4—C23 | 106.6 (2) | C9—C11—H11A | 108.79 |
C5—C4—C23 | 114.69 (19) | C9—C11—H11B | 108.79 |
C5—C4—C24 | 109.16 (19) | C12—C11—H11A | 108.82 |
C23—C4—C24 | 108.0 (2) | C12—C11—H11B | 108.81 |
C3—C4—C24 | 108.6 (2) | H11A—C11—H11B | 107.69 |
C4—C5—C10 | 116.91 (17) | C11—C12—H12A | 117.05 |
C6—C5—C10 | 110.65 (18) | C13—C12—H12A | 117.06 |
C4—C5—C6 | 114.11 (18) | C14—C15—H15A | 108.60 |
C5—C6—C7 | 110.32 (19) | C14—C15—H15B | 108.61 |
C6—C7—C8 | 113.78 (18) | C16—C15—H15A | 108.58 |
C7—C8—C9 | 110.25 (18) | C16—C15—H15B | 108.59 |
C7—C8—C26 | 107.68 (19) | H15A—C15—H15B | 107.55 |
C9—C8—C14 | 107.34 (17) | C15—C16—H16A | 109.18 |
C9—C8—C26 | 111.55 (19) | C15—C16—H16B | 109.19 |
C14—C8—C26 | 109.80 (18) | C17—C16—H16A | 109.18 |
C7—C8—C14 | 110.23 (18) | C17—C16—H16B | 109.19 |
C8—C9—C10 | 117.44 (18) | H16A—C16—H16B | 107.89 |
C8—C9—C11 | 109.9 (2) | C13—C18—H18A | 106.62 |
C10—C9—C11 | 112.65 (19) | C17—C18—H18A | 106.61 |
C1—C10—C9 | 106.86 (18) | C19—C18—H18A | 106.61 |
C1—C10—C25 | 109.2 (2) | C18—C19—H19A | 108.68 |
C5—C10—C9 | 106.28 (17) | C18—C19—H19B | 108.72 |
C5—C10—C25 | 113.40 (19) | C20—C19—H19A | 108.70 |
C9—C10—C25 | 113.41 (19) | C20—C19—H19B | 108.71 |
C1—C10—C5 | 107.30 (19) | H19A—C19—H19B | 107.63 |
C9—C11—C12 | 113.8 (2) | O4—C21—H21A | 109.07 |
C11—C12—C13 | 125.9 (2) | C20—C21—H21A | 109.05 |
C12—C13—C18 | 118.3 (2) | C22—C21—H21A | 109.07 |
C14—C13—C18 | 120.8 (2) | C17—C22—H22A | 108.85 |
C12—C13—C14 | 120.7 (2) | C17—C22—H22B | 108.87 |
C8—C14—C15 | 110.34 (18) | C21—C22—H22A | 108.84 |
C8—C14—C27 | 112.56 (18) | C21—C22—H22B | 108.87 |
C8—C14—C13 | 108.21 (18) | H22A—C22—H22B | 107.72 |
C13—C14—C27 | 107.61 (19) | C4—C23—H23A | 109.47 |
C15—C14—C27 | 106.55 (19) | C4—C23—H23B | 109.48 |
C13—C14—C15 | 111.58 (18) | C4—C23—H23C | 109.46 |
C14—C15—C16 | 114.68 (19) | H23A—C23—H23B | 109.48 |
C15—C16—C17 | 112.11 (18) | H23A—C23—H23C | 109.47 |
C16—C17—C18 | 109.93 (18) | H23B—C23—H23C | 109.47 |
C16—C17—C28 | 111.87 (19) | C4—C24—H24A | 109.49 |
C18—C17—C22 | 110.89 (18) | C4—C24—H24B | 109.49 |
C16—C17—C22 | 111.4 (2) | C4—C24—H24C | 109.48 |
C22—C17—C28 | 103.70 (17) | H24A—C24—H24B | 109.47 |
C18—C17—C28 | 108.96 (19) | H24A—C24—H24C | 109.46 |
C13—C18—C17 | 113.1 (2) | H24B—C24—H24C | 109.45 |
C13—C18—C19 | 110.89 (18) | C10—C25—H25A | 109.45 |
C17—C18—C19 | 112.6 (2) | C10—C25—H25B | 109.46 |
C18—C19—C20 | 114.2 (2) | C10—C25—H25C | 109.46 |
C19—C20—C21 | 105.5 (2) | H25A—C25—H25B | 109.48 |
C19—C20—C30 | 111.8 (3) | H25A—C25—H25C | 109.49 |
C21—C20—C29 | 108.7 (3) | H25B—C25—H25C | 109.49 |
C21—C20—C30 | 112.7 (3) | C8—C26—H26A | 109.47 |
C29—C20—C30 | 109.8 (3) | C8—C26—H26B | 109.49 |
C19—C20—C29 | 108.2 (2) | C8—C26—H26C | 109.46 |
O4—C21—C22 | 107.40 (18) | H26A—C26—H26B | 109.48 |
C20—C21—C22 | 113.0 (2) | H26A—C26—H26C | 109.46 |
O4—C21—C20 | 109.2 (2) | H26B—C26—H26C | 109.47 |
C17—C22—C21 | 113.54 (18) | C14—C27—H27A | 109.48 |
O2—C28—C17 | 123.7 (2) | C14—C27—H27B | 109.49 |
O3—C28—C17 | 113.8 (2) | C14—C27—H27C | 109.48 |
O2—C28—O3 | 122.3 (2) | H27A—C27—H27B | 109.45 |
O4—C31—C32 | 110.3 (3) | H27A—C27—H27C | 109.47 |
O5—C31—C32 | 125.2 (3) | H27B—C27—H27C | 109.46 |
O4—C31—O5 | 124.5 (3) | C20—C29—H29A | 109.48 |
C2—C1—H1A | 108.93 | C20—C29—H29B | 109.49 |
C2—C1—H1B | 108.91 | C20—C29—H29C | 109.48 |
C10—C1—H1A | 108.92 | H29A—C29—H29B | 109.48 |
C10—C1—H1B | 108.90 | H29A—C29—H29C | 109.46 |
H1A—C1—H1B | 107.74 | H29B—C29—H29C | 109.45 |
C1—C2—H2A | 108.95 | C20—C30—H30A | 109.47 |
C1—C2—H2B | 108.94 | C20—C30—H30B | 109.49 |
C3—C2—H2A | 108.97 | C20—C30—H30C | 109.50 |
C3—C2—H2B | 108.97 | H30A—C30—H30B | 109.45 |
H2A—C2—H2B | 107.74 | H30A—C30—H30C | 109.45 |
C4—C5—H5A | 104.56 | H30B—C30—H30C | 109.48 |
C6—C5—H5A | 104.57 | C31—C32—H32A | 109.50 |
C10—C5—H5A | 104.56 | C31—C32—H32B | 109.47 |
C5—C6—H6A | 109.57 | C31—C32—H32C | 109.47 |
C5—C6—H6B | 109.59 | H32A—C32—H32B | 109.47 |
C7—C6—H6A | 109.58 | H32A—C32—H32C | 109.46 |
C7—C6—H6B | 109.61 | H32B—C32—H32C | 109.45 |
H6A—C6—H6B | 108.13 | | |
| | | |
C31—O4—C21—C20 | 109.0 (3) | C10—C9—C11—C12 | −169.0 (2) |
C31—O4—C21—C22 | −128.2 (3) | C11—C9—C10—C5 | −179.1 (2) |
C21—O4—C31—O5 | 10.0 (4) | C11—C9—C10—C25 | 55.7 (3) |
C21—O4—C31—C32 | −168.0 (2) | C11—C9—C10—C1 | −64.7 (3) |
C2—C1—C10—C25 | 68.1 (3) | C9—C11—C12—C13 | 4.9 (4) |
C10—C1—C2—C3 | 52.7 (3) | C11—C12—C13—C14 | −2.5 (4) |
C2—C1—C10—C5 | −55.2 (3) | C11—C12—C13—C18 | −177.6 (3) |
C2—C1—C10—C9 | −168.9 (2) | C12—C13—C14—C27 | −91.8 (3) |
C1—C2—C3—O1 | 137.5 (3) | C18—C13—C14—C8 | −155.05 (19) |
C1—C2—C3—C4 | −45.8 (3) | C18—C13—C14—C27 | 83.1 (2) |
O1—C3—C4—C5 | −141.7 (2) | C12—C13—C18—C17 | −146.6 (2) |
C2—C3—C4—C23 | −83.1 (3) | C18—C13—C14—C15 | −33.5 (3) |
C2—C3—C4—C24 | 160.7 (2) | C14—C13—C18—C17 | 38.4 (3) |
C2—C3—C4—C5 | 41.5 (3) | C14—C13—C18—C19 | −89.2 (3) |
O1—C3—C4—C23 | 93.7 (3) | C12—C13—C14—C15 | 151.6 (2) |
O1—C3—C4—C24 | −22.5 (3) | C12—C13—C18—C19 | 85.9 (3) |
C3—C4—C5—C6 | −178.10 (19) | C12—C13—C14—C8 | 30.0 (3) |
C3—C4—C5—C10 | −46.8 (3) | C8—C14—C15—C16 | 161.68 (18) |
C23—C4—C5—C6 | −58.3 (3) | C13—C14—C15—C16 | 41.4 (3) |
C23—C4—C5—C10 | 73.1 (3) | C27—C14—C15—C16 | −75.8 (2) |
C24—C4—C5—C6 | 63.1 (3) | C14—C15—C16—C17 | −56.5 (3) |
C24—C4—C5—C10 | −165.6 (2) | C15—C16—C17—C28 | −62.5 (2) |
C10—C5—C6—C7 | 64.1 (2) | C15—C16—C17—C22 | −178.00 (18) |
C4—C5—C10—C25 | −66.5 (3) | C15—C16—C17—C18 | 58.7 (2) |
C4—C5—C10—C1 | 54.2 (2) | C22—C17—C18—C13 | −172.20 (19) |
C4—C5—C10—C9 | 168.26 (18) | C16—C17—C18—C19 | 78.0 (3) |
C4—C5—C6—C7 | −161.65 (18) | C28—C17—C18—C19 | −159.1 (2) |
C6—C5—C10—C25 | 66.4 (2) | C22—C17—C18—C19 | −45.6 (3) |
C6—C5—C10—C1 | −172.88 (18) | C28—C17—C18—C13 | 74.3 (2) |
C6—C5—C10—C9 | −58.8 (2) | C28—C17—C22—C21 | 164.3 (2) |
C5—C6—C7—C8 | −57.4 (2) | C16—C17—C28—O2 | 155.1 (3) |
C6—C7—C8—C9 | 46.9 (3) | C16—C17—C28—O3 | −29.9 (3) |
C6—C7—C8—C14 | 165.21 (18) | C18—C17—C28—O2 | 33.4 (3) |
C6—C7—C8—C26 | −75.0 (2) | C18—C17—C28—O3 | −151.7 (2) |
C7—C8—C9—C10 | −46.0 (3) | C16—C17—C22—C21 | −75.3 (3) |
C26—C8—C9—C10 | 73.6 (2) | C18—C17—C22—C21 | 47.5 (3) |
C26—C8—C9—C11 | −56.9 (3) | C16—C17—C18—C13 | −48.6 (3) |
C7—C8—C14—C13 | −179.52 (18) | C22—C17—C28—O3 | 90.2 (2) |
C7—C8—C14—C15 | 58.1 (2) | C22—C17—C28—O2 | −84.8 (3) |
C7—C8—C9—C11 | −176.51 (19) | C13—C18—C19—C20 | −177.8 (3) |
C14—C8—C9—C10 | −166.07 (18) | C17—C18—C19—C20 | 54.4 (4) |
C14—C8—C9—C11 | 63.4 (2) | C18—C19—C20—C21 | −59.1 (3) |
C9—C8—C14—C27 | 59.4 (2) | C18—C19—C20—C29 | −175.2 (3) |
C26—C8—C14—C13 | 62.0 (2) | C18—C19—C20—C30 | 63.8 (4) |
C26—C8—C14—C15 | −60.3 (2) | C19—C20—C21—O4 | 179.3 (2) |
C26—C8—C14—C27 | −179.2 (2) | C30—C20—C21—O4 | 57.0 (3) |
C7—C8—C14—C27 | −60.7 (2) | C30—C20—C21—C22 | −62.4 (3) |
C9—C8—C14—C13 | −59.4 (2) | C29—C20—C21—O4 | −64.9 (3) |
C9—C8—C14—C15 | 178.24 (17) | C29—C20—C21—C22 | 175.6 (2) |
C8—C9—C10—C1 | 166.0 (2) | C19—C20—C21—C22 | 59.8 (3) |
C8—C9—C10—C5 | 51.7 (2) | O4—C21—C22—C17 | −177.6 (2) |
C8—C9—C10—C25 | −73.6 (3) | C20—C21—C22—C17 | −57.1 (3) |
C8—C9—C11—C12 | −36.0 (3) | | |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1/2, −y−1/2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1iv | 0.82 | 1.97 | 2.779 (3) | 171 |
C15—H15B···O3 | 0.97 | 2.60 | 3.136 (3) | 115 |
C18—H18A···O2 | 0.98 | 2.41 | 2.822 (3) | 105 |
C21—H21A···O5 | 0.98 | 2.29 | 2.731 (4) | 106 |
Symmetry code: (iv) −x+1/2, −y, z−1/2. |