3-Oxo-18α-olean-28,13β-olide.

The title terpene, C(30)H(46)O(3), is a 28,13β-lactone of oleanolic acid prepared with bis-muth trifluoro-methane-sulfonate (OTf), Bi(OTf)(3)·xH(2)O. All rings are trans-fused. The X-ray study shows the inversion of the orientation of 18-H in the lactonization reaction. A quantum chemical ab-initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol-ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.

Related literature

For general background to the use of natural products as sources of anti­cancer drugs, see: Koehn & Carter (2005 ▶). For the biological activity of oleanolic acid, see: Ringbom et al. (1998 ▶); Ma et al. (2000 ▶); Tokuda et al. (1986 ▶); Horiuchi et al. (2007 ▶); Lee et al. (1994 ▶); Sohn et al. (1995 ▶). For the bio­syn­thesis of penta­cyclic triterpenoids, see: Gershenzon & Dudareva (2007 ▶); Salvador (2010 ▶); Dzubak et al. (2006 ▶). For the lactonization reaction of oleanane-type triterpenoids, see: Cheriti et al. (1994 ▶). For the synthesis of the title compound, see: Salvador et al. (2009 ▶). For related structures, see: Eggleston (1987 ▶); Chang et al. (1982 ▶); Sutthivaiyakit et al. (2001 ▶); Wang et al. (2006 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Duax & Norton (1975 ▶). The quantum chemical calculations were performed with the computer program GAMESS (Schmidt et al., 1993 ▶).

Experimental

Crystal data

C30H46O3

M = 454.67

Monoclinic,

a = 6.7789 (3) Å

b = 12.3122 (6) Å

c = 15.4524 (7) Å

β = 99.644 (2)°

V = 1271.48 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.45 × 0.17 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.746, T max = 1.0

16467 measured reflections

2536 independent reflections

1805 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.100

S = 1.08

2536 reflections

305 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002903X/rk2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002903X/rk2222Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H46O3	Dx = 1.188 Mg m−3
Mr = 454.67	Melting point: 583 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.7789 (3) Å	Cell parameters from 4019 reflections
b = 12.3122 (6) Å	θ = 3.1–21.5°
c = 15.4524 (7) Å	µ = 0.07 mm−1
β = 99.644 (2)°	T = 295 K
V = 1271.48 (10) Å3	Plate, colourless
Z = 2	0.45 × 0.17 × 0.04 mm
F(000) = 500

Bruker APEXII CCD area-detector diffractometer	2536 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ– and ω–scans	θmax = 25.8°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −8→8
Tmin = 0.746, Tmax = 1.0	k = −14→15
16467 measured reflections	l = −18→18

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) = 0.100	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3
2536 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq
O13	0.4607 (3)	−0.02601 (19)	0.48624 (13)	0.0397 (6)
O28	0.7505 (3)	0.0179 (3)	0.56915 (16)	0.0794 (10)
O3	−0.5087 (4)	−0.0157 (4)	0.0038 (2)	0.0996 (12)
C1	−0.1906 (5)	−0.1242 (3)	0.1826 (2)	0.0491 (9)
H1A	−0.2856	−0.0918	0.2154	0.059*
H1B	−0.1540	−0.1948	0.2081	0.059*
C2	−0.2931 (6)	−0.1399 (4)	0.0868 (2)	0.0646 (11)
H2A	−0.2056	−0.1812	0.0554	0.077*
H2B	−0.4155	−0.1812	0.0856	0.077*
C3	−0.3412 (5)	−0.0339 (4)	0.0419 (2)	0.0575 (10)
C4	−0.1742 (5)	0.0484 (3)	0.0468 (2)	0.0520 (10)
C23	−0.0394 (6)	0.0166 (5)	−0.0194 (2)	0.0835 (16)
H23A	−0.1123	0.0244	−0.0780	0.125*
H23B	0.0026	−0.0575	−0.0098	0.125*
H23C	0.0760	0.0631	−0.0120	0.125*
C24	−0.2693 (7)	0.1595 (4)	0.0201 (3)	0.0878 (16)
H24A	−0.3445	0.1550	−0.0382	0.132*
H24B	−0.1660	0.2131	0.0217	0.132*
H24C	−0.3568	0.1796	0.0603	0.132*
C5	−0.0633 (4)	0.0555 (3)	0.1440 (2)	0.0407 (8)
H5	−0.1623	0.0875	0.1760	0.049*
C6	0.1103 (5)	0.1352 (3)	0.1581 (2)	0.0583 (11)
H6A	0.0742	0.2001	0.1234	0.070*
H6B	0.2257	0.1027	0.1387	0.070*
C7	0.1632 (5)	0.1656 (3)	0.2547 (2)	0.0542 (10)
H7A	0.0514	0.2047	0.2717	0.065*
H7B	0.2770	0.2144	0.2621	0.065*
C8	0.2137 (4)	0.0679 (3)	0.3170 (2)	0.0356 (8)
C26	0.4243 (4)	0.0295 (4)	0.3042 (2)	0.0578 (11)
H26A	0.4297	0.0250	0.2426	0.087*
H26B	0.4510	−0.0407	0.3306	0.087*
H26C	0.5229	0.0804	0.3315	0.087*
C9	0.0551 (4)	−0.0227 (2)	0.29225 (17)	0.0292 (7)
H9	−0.0679	0.0065	0.3088	0.035*
C10	−0.0033 (4)	−0.0528 (3)	0.19274 (19)	0.0376 (8)
C11	0.1095 (5)	−0.1204 (3)	0.3527 (2)	0.0406 (8)
H11A	0.0099	−0.1769	0.3373	0.049*
H11B	0.2376	−0.1491	0.3435	0.049*
C12	0.1212 (4)	−0.0914 (2)	0.44899 (19)	0.0335 (7)
H12A	−0.0135	−0.0785	0.4601	0.040*
H12B	0.1738	−0.1536	0.4840	0.040*
C13	0.2476 (4)	0.0060 (2)	0.48011 (18)	0.0266 (7)
C14	0.2075 (4)	0.1043 (2)	0.4157 (2)	0.0317 (7)
C27	−0.0006 (4)	0.1511 (3)	0.4245 (2)	0.0460 (9)
H27A	−0.0924	0.0924	0.4278	0.069*
H27B	−0.0491	0.1954	0.3743	0.069*
H27C	0.0108	0.1943	0.4768	0.069*
C15	0.3649 (5)	0.1931 (3)	0.4452 (2)	0.0546 (10)
H15A	0.4879	0.1741	0.4246	0.066*
H15B	0.3177	0.2612	0.4177	0.066*
C16	0.4105 (6)	0.2097 (3)	0.5445 (2)	0.0559 (11)
H16A	0.3018	0.2502	0.5628	0.067*
H16B	0.5313	0.2528	0.5590	0.067*
C17	0.4383 (4)	0.1023 (3)	0.5959 (2)	0.0376 (8)
C22	0.5210 (5)	0.1223 (3)	0.6926 (2)	0.0504 (10)
H22A	0.6595	0.1451	0.6982	0.061*
H22B	0.4464	0.1809	0.7139	0.061*
C21	0.5095 (5)	0.0229 (3)	0.7492 (2)	0.0498 (9)
H21A	0.5475	0.0430	0.8104	0.060*
H21B	0.6049	−0.0307	0.7358	0.060*
C20	0.3009 (5)	−0.0285 (3)	0.7359 (2)	0.0436 (8)
C19	0.2422 (4)	−0.0582 (3)	0.63857 (18)	0.0361 (8)
H19A	0.3342	−0.1129	0.6240	0.043*
H19B	0.1093	−0.0899	0.6293	0.043*
C18	0.2434 (4)	0.0383 (2)	0.57641 (18)	0.0288 (7)
H18	0.1292	0.0860	0.5797	0.035*
C29	0.3103 (7)	−0.1316 (4)	0.7907 (2)	0.0714 (13)
H29A	0.1787	−0.1622	0.7860	0.107*
H29B	0.3608	−0.1147	0.8510	0.107*
H29C	0.3975	−0.1831	0.7696	0.107*
C30	0.1485 (5)	0.0488 (4)	0.7642 (2)	0.0659 (12)
H30A	0.0215	0.0129	0.7596	0.099*
H30B	0.1350	0.1117	0.7269	0.099*
H30C	0.1929	0.0707	0.8239	0.099*
C28	0.5721 (4)	0.0295 (3)	0.5524 (2)	0.0458 (9)
C25	0.1610 (5)	−0.1171 (4)	0.1569 (2)	0.0607 (11)
H25A	0.2562	−0.0674	0.1394	0.091*
H25B	0.1014	−0.1594	0.1071	0.091*
H25C	0.2277	−0.1645	0.2018	0.091*

	U11	U22	U33	U12	U13	U23
O13	0.0281 (10)	0.0565 (15)	0.0345 (12)	0.0119 (10)	0.0056 (9)	0.0031 (12)
O28	0.0242 (12)	0.156 (3)	0.0571 (16)	0.0006 (16)	0.0051 (10)	0.0102 (19)
O3	0.0579 (16)	0.149 (3)	0.082 (2)	−0.002 (2)	−0.0183 (14)	0.010 (2)
C1	0.061 (2)	0.047 (2)	0.037 (2)	−0.0057 (18)	0.0020 (16)	−0.0074 (18)
C2	0.067 (2)	0.071 (3)	0.051 (3)	−0.010 (2)	−0.0014 (19)	−0.013 (2)
C3	0.052 (2)	0.084 (3)	0.033 (2)	0.006 (2)	−0.0018 (16)	−0.009 (2)
C4	0.051 (2)	0.070 (3)	0.0314 (19)	0.007 (2)	−0.0031 (15)	0.0083 (19)
C23	0.070 (3)	0.152 (5)	0.030 (2)	0.003 (3)	0.0140 (18)	0.006 (3)
C24	0.106 (3)	0.093 (4)	0.051 (3)	0.016 (3)	−0.025 (2)	0.017 (3)
C5	0.0375 (16)	0.052 (2)	0.0326 (18)	0.0052 (16)	0.0044 (13)	0.0061 (16)
C6	0.064 (2)	0.069 (3)	0.039 (2)	−0.013 (2)	0.0010 (17)	0.021 (2)
C7	0.064 (2)	0.052 (2)	0.043 (2)	−0.0184 (19)	−0.0026 (17)	0.0150 (19)
C8	0.0326 (15)	0.043 (2)	0.0314 (18)	−0.0024 (14)	0.0055 (13)	0.0088 (15)
C26	0.0335 (16)	0.100 (3)	0.043 (2)	0.002 (2)	0.0128 (14)	0.005 (2)
C9	0.0298 (14)	0.0299 (18)	0.0292 (16)	0.0054 (13)	0.0086 (11)	0.0008 (15)
C10	0.0355 (16)	0.046 (2)	0.0319 (18)	0.0097 (15)	0.0074 (12)	−0.0008 (16)
C11	0.0567 (19)	0.0298 (18)	0.0341 (19)	0.0041 (16)	0.0036 (14)	−0.0011 (15)
C12	0.0444 (17)	0.0251 (17)	0.0308 (18)	−0.0017 (14)	0.0057 (13)	0.0006 (14)
C13	0.0239 (13)	0.0277 (17)	0.0291 (16)	0.0007 (12)	0.0072 (11)	0.0002 (13)
C14	0.0334 (15)	0.0265 (17)	0.0339 (18)	−0.0027 (13)	0.0021 (12)	0.0023 (15)
C27	0.0503 (19)	0.038 (2)	0.047 (2)	0.0142 (16)	−0.0005 (15)	−0.0047 (17)
C15	0.068 (2)	0.044 (2)	0.047 (2)	−0.0272 (19)	−0.0070 (17)	0.0108 (18)
C16	0.071 (2)	0.041 (2)	0.050 (2)	−0.0314 (19)	−0.0097 (18)	0.0028 (19)
C17	0.0334 (15)	0.043 (2)	0.0347 (18)	−0.0147 (14)	0.0018 (13)	0.0031 (16)
C22	0.0487 (19)	0.055 (3)	0.045 (2)	−0.0213 (18)	−0.0012 (15)	−0.0043 (19)
C21	0.0466 (18)	0.063 (2)	0.037 (2)	−0.0108 (18)	−0.0020 (14)	0.000 (2)
C20	0.0480 (17)	0.052 (2)	0.0299 (17)	−0.0110 (17)	0.0046 (13)	−0.0015 (18)
C19	0.0387 (16)	0.039 (2)	0.0314 (18)	−0.0067 (14)	0.0076 (12)	−0.0006 (15)
C18	0.0245 (13)	0.0292 (18)	0.0326 (17)	−0.0015 (12)	0.0044 (11)	−0.0013 (15)
C29	0.098 (3)	0.077 (3)	0.035 (2)	−0.030 (3)	−0.001 (2)	0.008 (2)
C30	0.059 (2)	0.094 (3)	0.048 (2)	−0.010 (2)	0.0200 (17)	−0.025 (2)
C28	0.0321 (17)	0.070 (3)	0.0352 (19)	−0.0053 (17)	0.0054 (13)	0.013 (2)
C25	0.062 (2)	0.081 (3)	0.038 (2)	0.033 (2)	0.0065 (17)	−0.006 (2)

O13—C28	1.351 (4)	C11—H11B	0.9700
O13—C13	1.485 (3)	C12—C13	1.505 (4)
O28—C28	1.202 (3)	C12—H12A	0.9700
O3—C3	1.209 (4)	C12—H12B	0.9700
C1—C10	1.530 (4)	C13—C18	1.545 (4)
C1—C2	1.539 (5)	C13—C14	1.562 (4)
C1—H1A	0.9700	C14—C15	1.542 (4)
C1—H1B	0.9700	C14—C27	1.551 (4)
C2—C3	1.488 (6)	C27—H27A	0.9600
C2—H2A	0.9700	C27—H27B	0.9600
C2—H2B	0.9700	C27—H27C	0.9600
C3—C4	1.512 (5)	C15—C16	1.528 (5)
C4—C23	1.533 (5)	C15—H15A	0.9700
C4—C24	1.538 (6)	C15—H15B	0.9700
C4—C5	1.566 (4)	C16—C17	1.537 (5)
C23—H23A	0.9600	C16—H16A	0.9700
C23—H23B	0.9600	C16—H16B	0.9700
C23—H23C	0.9600	C17—C28	1.510 (5)
C24—H24A	0.9600	C17—C18	1.525 (4)
C24—H24B	0.9600	C17—C22	1.526 (4)
C24—H24C	0.9600	C22—C21	1.514 (5)
C5—C6	1.520 (5)	C22—H22A	0.9700
C5—C10	1.551 (4)	C22—H22B	0.9700
C5—H5	0.9800	C21—C20	1.531 (4)
C6—C7	1.523 (5)	C21—H21A	0.9700
C6—H6A	0.9700	C21—H21B	0.9700
C6—H6B	0.9700	C20—C30	1.521 (5)
C7—C8	1.542 (5)	C20—C29	1.522 (5)
C7—H7A	0.9700	C20—C19	1.534 (4)
C7—H7B	0.9700	C19—C18	1.528 (4)
C8—C26	1.548 (4)	C19—H19A	0.9700
C8—C9	1.552 (4)	C19—H19B	0.9700
C8—C14	1.597 (4)	C18—H18	0.9800
C26—H26A	0.9600	C29—H29A	0.9600
C26—H26B	0.9600	C29—H29B	0.9600
C26—H26C	0.9600	C29—H29C	0.9600
C9—C11	1.530 (4)	C30—H30A	0.9600
C9—C10	1.567 (4)	C30—H30B	0.9600
C9—H9	0.9800	C30—H30C	0.9600
C10—C25	1.544 (4)	C25—H25A	0.9600
C11—C12	1.520 (4)	C25—H25B	0.9600
C11—H11A	0.9700	C25—H25C	0.9600
C28—O13—C13	109.2 (2)	O13—C13—C12	107.7 (2)
C10—C1—C2	113.9 (3)	O13—C13—C18	100.44 (19)
C10—C1—H1A	108.8	C12—C13—C18	114.3 (2)
C2—C1—H1A	108.8	O13—C13—C14	108.1 (2)
C10—C1—H1B	108.8	C12—C13—C14	112.7 (2)
C2—C1—H1B	108.8	C18—C13—C14	112.6 (2)
H1A—C1—H1B	107.7	C15—C14—C27	107.8 (3)
C3—C2—C1	111.5 (3)	C15—C14—C13	108.9 (2)
C3—C2—H2A	109.3	C27—C14—C13	107.2 (2)
C1—C2—H2A	109.3	C15—C14—C8	110.7 (2)
C3—C2—H2B	109.3	C27—C14—C8	111.0 (2)
C1—C2—H2B	109.3	C13—C14—C8	111.2 (2)
H2A—C2—H2B	108.0	C14—C27—H27A	109.5
O3—C3—C2	120.3 (4)	C14—C27—H27B	109.5
O3—C3—C4	122.3 (4)	H27A—C27—H27B	109.5
C2—C3—C4	117.4 (3)	C14—C27—H27C	109.5
C3—C4—C23	108.7 (3)	H27A—C27—H27C	109.5
C3—C4—C24	107.8 (3)	H27B—C27—H27C	109.5
C23—C4—C24	108.5 (4)	C16—C15—C14	113.9 (3)
C3—C4—C5	108.7 (3)	C16—C15—H15A	108.8
C23—C4—C5	114.3 (3)	C14—C15—H15A	108.8
C24—C4—C5	108.7 (3)	C16—C15—H15B	108.8
C4—C23—H23A	109.5	C14—C15—H15B	108.8
C4—C23—H23B	109.5	H15A—C15—H15B	107.7
H23A—C23—H23B	109.5	C15—C16—C17	113.0 (3)
C4—C23—H23C	109.5	C15—C16—H16A	109.0
H23A—C23—H23C	109.5	C17—C16—H16A	109.0
H23B—C23—H23C	109.5	C15—C16—H16B	109.0
C4—C24—H24A	109.5	C17—C16—H16B	109.0
C4—C24—H24B	109.5	H16A—C16—H16B	107.8
H24A—C24—H24B	109.5	C28—C17—C18	99.8 (2)
C4—C24—H24C	109.5	C28—C17—C22	112.5 (3)
H24A—C24—H24C	109.5	C18—C17—C22	116.2 (3)
H24B—C24—H24C	109.5	C28—C17—C16	108.1 (3)
C6—C5—C10	110.6 (2)	C18—C17—C16	108.4 (2)
C6—C5—C4	114.1 (3)	C22—C17—C16	111.1 (3)
C10—C5—C4	117.5 (3)	C21—C22—C17	112.9 (3)
C6—C5—H5	104.3	C21—C22—H22A	109.0
C10—C5—H5	104.3	C17—C22—H22A	109.0
C4—C5—H5	104.3	C21—C22—H22B	109.0
C5—C6—C7	110.4 (3)	C17—C22—H22B	109.0
C5—C6—H6A	109.6	H22A—C22—H22B	107.8
C7—C6—H6A	109.6	C22—C21—C20	113.1 (3)
C5—C6—H6B	109.6	C22—C21—H21A	109.0
C7—C6—H6B	109.6	C20—C21—H21A	109.0
H6A—C6—H6B	108.1	C22—C21—H21B	109.0
C6—C7—C8	114.3 (3)	C20—C21—H21B	109.0
C6—C7—H7A	108.7	H21A—C21—H21B	107.8
C8—C7—H7A	108.7	C30—C20—C29	109.3 (3)
C6—C7—H7B	108.7	C30—C20—C21	111.1 (3)
C8—C7—H7B	108.7	C29—C20—C21	108.5 (3)
H7A—C7—H7B	107.6	C30—C20—C19	110.7 (3)
C7—C8—C26	105.8 (3)	C29—C20—C19	109.0 (3)
C7—C8—C9	109.5 (2)	C21—C20—C19	108.2 (2)
C26—C8—C9	111.4 (3)	C18—C19—C20	113.8 (3)
C7—C8—C14	109.8 (3)	C18—C19—H19A	108.8
C26—C8—C14	112.4 (2)	C20—C19—H19A	108.8
C9—C8—C14	108.0 (2)	C18—C19—H19B	108.8
C8—C26—H26A	109.5	C20—C19—H19B	108.8
C8—C26—H26B	109.5	H19A—C19—H19B	107.7
H26A—C26—H26B	109.5	C17—C18—C19	111.9 (2)
C8—C26—H26C	109.5	C17—C18—C13	99.7 (2)
H26A—C26—H26C	109.5	C19—C18—C13	114.1 (2)
H26B—C26—H26C	109.5	C17—C18—H18	110.2
C11—C9—C8	109.2 (2)	C19—C18—H18	110.2
C11—C9—C10	114.1 (2)	C13—C18—H18	110.2
C8—C9—C10	117.6 (2)	C20—C29—H29A	109.5
C11—C9—H9	104.9	C20—C29—H29B	109.5
C8—C9—H9	104.9	H29A—C29—H29B	109.5
C10—C9—H9	104.9	C20—C29—H29C	109.5
C1—C10—C25	107.7 (3)	H29A—C29—H29C	109.5
C1—C10—C5	107.4 (2)	H29B—C29—H29C	109.5
C25—C10—C5	114.4 (3)	C20—C30—H30A	109.5
C1—C10—C9	107.8 (2)	C20—C30—H30B	109.5
C25—C10—C9	113.3 (2)	H30A—C30—H30B	109.5
C5—C10—C9	106.0 (2)	C20—C30—H30C	109.5
C12—C11—C9	112.4 (3)	H30A—C30—H30C	109.5
C12—C11—H11A	109.1	H30B—C30—H30C	109.5
C9—C11—H11A	109.1	O28—C28—O13	121.1 (3)
C12—C11—H11B	109.1	O28—C28—C17	129.2 (3)
C9—C11—H11B	109.1	O13—C28—C17	109.6 (2)
H11A—C11—H11B	107.9	C10—C25—H25A	109.5
C13—C12—C11	115.7 (2)	C10—C25—H25B	109.5
C13—C12—H12A	108.4	H25A—C25—H25B	109.5
C11—C12—H12A	108.4	C10—C25—H25C	109.5
C13—C12—H12B	108.4	H25A—C25—H25C	109.5
C11—C12—H12B	108.4	H25B—C25—H25C	109.5
H12A—C12—H12B	107.4
C10—C1—C2—C3	−54.8 (4)	O13—C13—C14—C27	−168.8 (2)
C1—C2—C3—O3	−128.1 (4)	C12—C13—C14—C27	72.3 (3)
C1—C2—C3—C4	51.3 (5)	C18—C13—C14—C27	−58.8 (3)
O3—C3—C4—C23	−102.1 (4)	O13—C13—C14—C8	69.8 (3)
C2—C3—C4—C23	78.4 (4)	C12—C13—C14—C8	−49.1 (3)
O3—C3—C4—C24	15.4 (5)	C18—C13—C14—C8	179.8 (2)
C2—C3—C4—C24	−164.1 (3)	C7—C8—C14—C15	−61.7 (3)
O3—C3—C4—C5	133.0 (4)	C26—C8—C14—C15	55.7 (4)
C2—C3—C4—C5	−46.5 (4)	C9—C8—C14—C15	179.0 (3)
C3—C4—C5—C6	179.5 (3)	C7—C8—C14—C27	58.0 (3)
C23—C4—C5—C6	57.9 (5)	C26—C8—C14—C27	175.4 (3)
C24—C4—C5—C6	−63.5 (4)	C9—C8—C14—C27	−61.4 (3)
C3—C4—C5—C10	47.6 (4)	C7—C8—C14—C13	177.2 (2)
C23—C4—C5—C10	−74.0 (4)	C26—C8—C14—C13	−65.4 (3)
C24—C4—C5—C10	164.6 (3)	C9—C8—C14—C13	57.8 (3)
C10—C5—C6—C7	−63.9 (4)	C27—C14—C15—C16	74.8 (4)
C4—C5—C6—C7	160.9 (3)	C13—C14—C15—C16	−41.1 (4)
C5—C6—C7—C8	56.5 (4)	C8—C14—C15—C16	−163.6 (3)
C6—C7—C8—C26	74.0 (4)	C14—C15—C16—C17	44.9 (4)
C6—C7—C8—C9	−46.1 (4)	C15—C16—C17—C28	45.6 (4)
C6—C7—C8—C14	−164.5 (3)	C15—C16—C17—C18	−61.7 (4)
C7—C8—C9—C11	178.4 (3)	C15—C16—C17—C22	169.5 (3)
C26—C8—C9—C11	61.8 (3)	C28—C17—C22—C21	−70.9 (4)
C14—C8—C9—C11	−62.0 (3)	C18—C17—C22—C21	43.2 (4)
C7—C8—C9—C10	46.4 (3)	C16—C17—C22—C21	167.7 (3)
C26—C8—C9—C10	−70.2 (3)	C17—C22—C21—C20	−51.3 (4)
C14—C8—C9—C10	166.0 (2)	C22—C21—C20—C30	−63.9 (4)
C2—C1—C10—C25	−70.1 (4)	C22—C21—C20—C29	176.0 (3)
C2—C1—C10—C5	53.6 (4)	C22—C21—C20—C19	57.8 (4)
C2—C1—C10—C9	167.3 (3)	C30—C20—C19—C18	64.2 (3)
C6—C5—C10—C1	174.8 (3)	C29—C20—C19—C18	−175.6 (3)
C4—C5—C10—C1	−51.7 (3)	C21—C20—C19—C18	−57.7 (3)
C6—C5—C10—C25	−65.7 (4)	C28—C17—C18—C19	78.8 (3)
C4—C5—C10—C25	67.8 (4)	C22—C17—C18—C19	−42.3 (4)
C6—C5—C10—C9	59.8 (3)	C16—C17—C18—C19	−168.3 (3)
C4—C5—C10—C9	−166.7 (2)	C28—C17—C18—C13	−42.3 (3)
C11—C9—C10—C1	62.4 (3)	C22—C17—C18—C13	−163.4 (3)
C8—C9—C10—C1	−167.9 (3)	C16—C17—C18—C13	70.7 (3)
C11—C9—C10—C25	−56.7 (4)	C20—C19—C18—C17	50.4 (3)
C8—C9—C10—C25	73.1 (4)	C20—C19—C18—C13	162.7 (2)
C11—C9—C10—C5	177.1 (2)	O13—C13—C18—C17	43.2 (3)
C8—C9—C10—C5	−53.2 (3)	C12—C13—C18—C17	158.1 (2)
C8—C9—C11—C12	58.6 (3)	C14—C13—C18—C17	−71.6 (3)
C10—C9—C11—C12	−167.6 (2)	O13—C13—C18—C19	−76.3 (3)
C9—C11—C12—C13	−50.4 (3)	C12—C13—C18—C19	38.7 (3)
C28—O13—C13—C12	−147.8 (2)	C14—C13—C18—C19	169.0 (2)
C28—O13—C13—C18	−27.9 (3)	C13—O13—C28—O28	−179.1 (3)
C28—O13—C13—C14	90.2 (3)	C13—O13—C28—C17	0.6 (3)
C11—C12—C13—O13	−73.7 (3)	C18—C17—C28—O28	−153.0 (4)
C11—C12—C13—C18	175.6 (2)	C22—C17—C28—O28	−29.3 (5)
C11—C12—C13—C14	45.4 (3)	C16—C17—C28—O28	93.8 (4)
O13—C13—C14—C15	−52.4 (3)	C18—C17—C28—O13	27.3 (3)
C12—C13—C14—C15	−171.3 (3)	C22—C17—C28—O13	151.1 (3)
C18—C13—C14—C15	57.6 (3)	C16—C17—C28—O13	−85.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26B···O13	0.96	2.40	2.865 (4)	109