A new triterpene of Miconia macrothyrsa leaves: 28-carboxy-3-oxoolean-12-en-21α-yl acetate

The title compound, C₃₂H₄₈O₅, 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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	Prism, white
Z = 4	0.50 × 0.40 × 0.30 mm
F(000) = 1120

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 0.3781P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O3^i	2.779 (3)	C25···C26	3.268 (4)
O2···C32^ii	3.081 (4)	C25···C23	3.228 (4)
O3···C15	3.136 (3)	C26···C25	3.268 (4)
O5···C1^iii	3.415 (4)	C26···C12	3.149 (4)
O1···H3^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^iv	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.