6α-Acetoxy-gedunin.

THE TITLE COMPOUND [SYSTEMATIC NAME: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis-(acet-yloxy)-1-(3-fur-yl)-1,5,6,6a,7,10a,10b,11,12,12a-deca-hydro-4b,7,7,10a,12a-penta-methyl-oxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglaia elaeagnoidea (A. Juss.) Benth. (Meliaceae) from Queensland, northern Australia. It contains the gedunin core of four trans-fused six-membered rings with an oxirane ring annelated to the fourth ring. A terminal 3-furyl unity and two acet-oxy groups in a mutual cis-disposition supplement the mol-ecule. A comparison between the gedunin cores of the title compound, the parent compound gedunin, and three further gedunin derivatives revealed considerable variations in their conformation stemming from the conformational lability of the first screw-boat ring and the third twist-boat ring. A sensitive measure for the third ring is one C-C-C-C torsion angle, which is 14.2 (2)° in the title compound, but varies in other cases from ca 20 to ca -40°. In the crystalline state, 6α-acetoxy-gedunin shows ten comparatively weak C-H⋯O inter-actions, with H⋯O distances in the range of 2.33-2.69 Å.

Related literature

For general background to the genus Aglaia and its potential bioctivity, see: Brader et al. (1998 ▶); Engelmeier et al. (2000 ▶); Fuzzati et al. (1996 ▶); Greger et al. (2000 ▶, 2001 ▶); Hausott et al. (2004 ▶); Jimenez et al. (1998 ▶); Lavie et al. (1972 ▶). For related structures, see: Mitsui et al. (2006 ▶); Sutherland et al. (1962 ▶); Toscano et al. (1996 ▶); Waratchareeyakul et al. (2004 ▶). For the NMR spectra of related compounds, see: Connolly et al. (1966 ▶); Mitsui et al. (2006 ▶); Taylor (1974 ▶); Waratchareeyakul et al. (2004 ▶).

Experimental

Crystal data

C30H36O9

M = 540.59

Orthorhombic,

a = 6.475 (2) Å

b = 14.914 (5) Å

c = 28.713 (9) Å

V = 2772.8 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.62 × 0.40 × 0.25 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.89, T max = 0.98

39048 measured reflections

4509 independent reflections

4077 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.04

4509 reflections

359 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT, SADABS and XPREP (Bruker, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027998/fj2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027998/fj2239Isup2.hkl

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

C30H36O9	F(000) = 1152
Mr = 540.59	Dx = 1.295 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 852 reflections
a = 6.475 (2) Å	θ = 2.4–29.8°
b = 14.914 (5) Å	µ = 0.10 mm−1
c = 28.713 (9) Å	T = 173 K
V = 2772.8 (15) Å3	Prism, colourless
Z = 4	0.62 × 0.40 × 0.25 mm

Bruker SMART APEX CCD diffractometer	4509 independent reflections
Radiation source: fine-focus sealed tube	4077 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −9→9
Tmin = 0.89, Tmax = 0.98	k = −20→20
39048 measured reflections	l = −40→40

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.3403P] where P = (Fo2 + 2Fc2)/3
4509 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.0587 (3)	0.73999 (11)	0.23019 (6)	0.0535 (4)
O2	0.3222 (2)	0.68452 (7)	0.40284 (4)	0.0308 (3)
O3	0.21379 (17)	0.50631 (7)	0.42004 (3)	0.0218 (2)
O4	0.67376 (18)	0.33557 (9)	0.41784 (4)	0.0303 (3)
O5	0.3916 (2)	0.20217 (8)	0.45502 (4)	0.0311 (3)
O6	0.3600 (2)	0.29114 (9)	0.51630 (4)	0.0371 (3)
O7	0.3049 (7)	−0.02998 (11)	0.35841 (9)	0.1021 (11)
O8	0.6555 (3)	0.70255 (12)	0.42549 (6)	0.0546 (4)
O9	0.3152 (3)	0.55979 (10)	0.49051 (4)	0.0413 (3)
C1	0.1155 (3)	0.51480 (13)	0.26444 (5)	0.0295 (3)
H1	0.0712	0.4558	0.2569	0.035*
C2	0.0178 (3)	0.58569 (14)	0.24571 (6)	0.0342 (4)
H2	−0.0937	0.5765	0.2247	0.041*
C3	0.0830 (3)	0.67781 (14)	0.25763 (6)	0.0354 (4)
C4	0.1727 (3)	0.69563 (11)	0.30666 (6)	0.0289 (3)
C5	0.2297 (2)	0.60496 (10)	0.33182 (5)	0.0220 (3)
H5	0.0998	0.5837	0.3471	0.026*
C6	0.3893 (2)	0.61484 (10)	0.37098 (5)	0.0230 (3)
H6	0.5258	0.6318	0.3573	0.028*
C7	0.4135 (2)	0.52809 (10)	0.39934 (5)	0.0210 (3)
H7	0.5176	0.5376	0.4246	0.025*
C8	0.4803 (2)	0.44830 (10)	0.36887 (5)	0.0198 (3)
C9	0.3279 (2)	0.43982 (10)	0.32698 (5)	0.0208 (3)
H9	0.1901	0.4274	0.3413	0.025*
C10	0.2973 (2)	0.52800 (10)	0.29783 (5)	0.0217 (3)
C11	0.3781 (3)	0.35593 (11)	0.29761 (5)	0.0302 (3)
H11A	0.4995	0.3692	0.2778	0.036*
H11B	0.2600	0.3436	0.2767	0.036*
C12	0.4241 (3)	0.27008 (11)	0.32647 (6)	0.0300 (3)
H12A	0.3503	0.2188	0.3122	0.036*
H12B	0.5739	0.2572	0.3249	0.036*
C13	0.3597 (2)	0.27762 (10)	0.37810 (5)	0.0230 (3)
C14	0.4749 (2)	0.35925 (10)	0.39801 (5)	0.0210 (3)
C15	0.5091 (2)	0.35775 (11)	0.44934 (5)	0.0248 (3)
H15	0.5181	0.4171	0.4654	0.030*
C16	0.4171 (3)	0.28141 (11)	0.47670 (5)	0.0268 (3)
C17	0.4394 (3)	0.19354 (11)	0.40509 (6)	0.0325 (4)
H17	0.5926	0.1892	0.4012	0.039*
C18	0.1228 (2)	0.28506 (11)	0.38491 (5)	0.0254 (3)
H18A	0.0824	0.3484	0.3851	0.038*
H18B	0.0840	0.2574	0.4146	0.038*
H18C	0.0522	0.2541	0.3594	0.038*
C19	0.4839 (3)	0.55432 (12)	0.26637 (5)	0.0286 (3)
H19A	0.5308	0.5016	0.2490	0.043*
H19B	0.5969	0.5767	0.2859	0.043*
H19C	0.4413	0.6012	0.2445	0.043*
C20	0.3434 (4)	0.10558 (12)	0.39106 (7)	0.0455 (5)
C21	0.4335 (7)	0.04307 (15)	0.36416 (10)	0.0767 (11)
H21	0.5673	0.0484	0.3509	0.092*
C22	0.1459 (5)	0.06906 (14)	0.40432 (10)	0.0588 (7)
H22	0.0451	0.0969	0.4235	0.071*
C23	0.1322 (8)	−0.01205 (18)	0.38421 (13)	0.0876 (13)
H23	0.0181	−0.0516	0.3875	0.105*
C24	−0.0104 (3)	0.74131 (13)	0.33278 (7)	0.0399 (4)
H24A	−0.0409	0.7993	0.3182	0.060*
H24B	0.0274	0.7507	0.3655	0.060*
H24C	−0.1327	0.7027	0.3311	0.060*
C25	0.3518 (3)	0.76299 (12)	0.30263 (7)	0.0367 (4)
H25A	0.3057	0.8158	0.2852	0.055*
H25B	0.4678	0.7348	0.2863	0.055*
H25C	0.3961	0.7813	0.3339	0.055*
C26	0.7086 (2)	0.46280 (12)	0.35367 (6)	0.0269 (3)
H26A	0.7211	0.5204	0.3375	0.040*
H26B	0.7507	0.4142	0.3327	0.040*
H26C	0.7978	0.4629	0.3813	0.040*
C27	0.4760 (4)	0.72270 (14)	0.42919 (7)	0.0419 (5)
C28	0.3892 (6)	0.79118 (17)	0.46226 (9)	0.0655 (8)
H28A	0.4966	0.8349	0.4702	0.098*
H28B	0.3415	0.7612	0.4907	0.098*
H28C	0.2729	0.8221	0.4475	0.098*
C29	0.1864 (3)	0.52448 (11)	0.46639 (5)	0.0268 (3)
C30	−0.0241 (3)	0.49403 (14)	0.48189 (6)	0.0382 (4)
H30A	−0.0316	0.4956	0.5160	0.057*
H30B	−0.0485	0.4327	0.4710	0.057*
H30C	−0.1294	0.5340	0.4688	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0596 (10)	0.0553 (9)	0.0454 (8)	0.0088 (8)	−0.0091 (7)	0.0263 (7)
O2	0.0402 (7)	0.0240 (5)	0.0281 (5)	−0.0007 (5)	0.0018 (5)	−0.0018 (4)
O3	0.0219 (5)	0.0257 (5)	0.0177 (4)	−0.0016 (4)	0.0032 (4)	0.0006 (4)
O4	0.0194 (5)	0.0432 (6)	0.0284 (5)	0.0036 (5)	0.0000 (4)	0.0133 (5)
O5	0.0357 (6)	0.0287 (6)	0.0289 (6)	−0.0005 (5)	−0.0027 (5)	0.0088 (5)
O6	0.0407 (7)	0.0463 (7)	0.0242 (5)	−0.0066 (6)	0.0035 (5)	0.0092 (5)
O7	0.200 (3)	0.0281 (8)	0.0781 (14)	0.0038 (15)	−0.016 (2)	−0.0129 (8)
O8	0.0467 (9)	0.0676 (10)	0.0496 (8)	−0.0210 (8)	−0.0039 (7)	−0.0149 (8)
O9	0.0463 (8)	0.0528 (8)	0.0247 (5)	−0.0105 (7)	0.0018 (6)	−0.0083 (6)
C1	0.0263 (8)	0.0408 (9)	0.0213 (6)	−0.0019 (7)	−0.0024 (6)	0.0031 (6)
C2	0.0247 (8)	0.0528 (10)	0.0251 (7)	0.0013 (8)	−0.0037 (6)	0.0097 (7)
C3	0.0259 (8)	0.0483 (10)	0.0319 (8)	0.0067 (8)	0.0012 (7)	0.0147 (7)
C4	0.0283 (8)	0.0298 (7)	0.0285 (7)	0.0048 (7)	0.0039 (6)	0.0101 (6)
C5	0.0198 (6)	0.0259 (7)	0.0202 (6)	0.0005 (5)	0.0021 (5)	0.0052 (5)
C6	0.0242 (7)	0.0232 (7)	0.0215 (6)	−0.0016 (6)	0.0023 (6)	0.0006 (5)
C7	0.0198 (6)	0.0250 (7)	0.0182 (6)	−0.0022 (5)	0.0004 (5)	0.0015 (5)
C8	0.0178 (6)	0.0238 (6)	0.0179 (6)	0.0006 (5)	0.0002 (5)	0.0035 (5)
C9	0.0211 (6)	0.0248 (6)	0.0166 (6)	−0.0007 (6)	0.0007 (5)	0.0023 (5)
C10	0.0205 (6)	0.0278 (7)	0.0169 (6)	0.0005 (6)	0.0011 (5)	0.0037 (5)
C11	0.0451 (10)	0.0276 (7)	0.0178 (6)	0.0009 (7)	0.0028 (7)	−0.0010 (6)
C12	0.0372 (9)	0.0284 (7)	0.0244 (7)	0.0084 (7)	0.0042 (6)	−0.0021 (6)
C13	0.0253 (7)	0.0213 (6)	0.0224 (6)	0.0049 (6)	0.0016 (5)	0.0015 (5)
C14	0.0184 (6)	0.0259 (7)	0.0187 (6)	0.0027 (5)	0.0010 (5)	0.0037 (5)
C15	0.0224 (7)	0.0308 (7)	0.0212 (6)	−0.0018 (6)	−0.0020 (6)	0.0065 (5)
C16	0.0229 (7)	0.0325 (8)	0.0249 (7)	−0.0006 (6)	−0.0026 (6)	0.0093 (6)
C17	0.0406 (9)	0.0257 (7)	0.0311 (8)	0.0103 (7)	0.0012 (7)	0.0049 (6)
C18	0.0242 (7)	0.0258 (7)	0.0262 (7)	−0.0016 (6)	−0.0013 (6)	0.0031 (6)
C19	0.0257 (7)	0.0383 (8)	0.0217 (6)	0.0022 (7)	0.0056 (6)	0.0082 (6)
C20	0.0767 (16)	0.0233 (8)	0.0365 (9)	0.0091 (10)	−0.0058 (10)	0.0034 (7)
C21	0.138 (3)	0.0313 (10)	0.0610 (15)	0.0238 (15)	0.0115 (19)	−0.0033 (10)
C22	0.0819 (18)	0.0284 (9)	0.0661 (14)	−0.0109 (11)	−0.0189 (14)	0.0047 (9)
C23	0.142 (4)	0.0335 (12)	0.087 (2)	−0.0168 (18)	−0.032 (3)	−0.0012 (13)
C24	0.0366 (9)	0.0372 (9)	0.0458 (10)	0.0111 (8)	0.0102 (8)	0.0104 (8)
C25	0.0387 (9)	0.0318 (8)	0.0397 (9)	−0.0024 (7)	0.0049 (8)	0.0140 (7)
C26	0.0180 (6)	0.0364 (8)	0.0263 (7)	0.0001 (6)	0.0030 (6)	0.0083 (6)
C27	0.0607 (13)	0.0341 (9)	0.0309 (8)	−0.0134 (9)	−0.0003 (9)	−0.0065 (7)
C28	0.095 (2)	0.0476 (13)	0.0538 (13)	−0.0037 (15)	−0.0014 (14)	−0.0251 (11)
C29	0.0343 (8)	0.0266 (7)	0.0195 (6)	−0.0010 (7)	0.0055 (6)	−0.0014 (5)
C30	0.0412 (10)	0.0434 (10)	0.0299 (8)	−0.0086 (8)	0.0164 (7)	−0.0055 (7)

O1—C3	1.227 (2)	C12—C13	1.544 (2)
O2—C27	1.374 (3)	C12—H12A	0.9900
O2—C6	1.4510 (18)	C12—H12B	0.9900
O3—C29	1.3697 (18)	C13—C14	1.538 (2)
O3—C7	1.4600 (18)	C13—C18	1.551 (2)
O4—C15	1.436 (2)	C13—C17	1.562 (2)
O4—C14	1.4517 (18)	C14—C15	1.491 (2)
O5—C16	1.346 (2)	C15—C16	1.506 (2)
O5—C17	1.472 (2)	C15—H15	1.0000
O6—C16	1.204 (2)	C17—C20	1.507 (3)
O7—C23	1.368 (6)	C17—H17	1.0000
O7—C21	1.381 (5)	C18—H18A	0.9800
O8—C27	1.205 (3)	C18—H18B	0.9800
O9—C29	1.205 (2)	C18—H18C	0.9800
C1—C2	1.344 (2)	C19—H19A	0.9800
C1—C10	1.531 (2)	C19—H19B	0.9800
C1—H1	0.9500	C19—H19C	0.9800
C2—C3	1.478 (3)	C20—C21	1.344 (3)
C2—H2	0.9500	C20—C22	1.441 (4)
C3—C4	1.546 (3)	C21—H21	0.9500
C4—C25	1.539 (3)	C22—C23	1.343 (4)
C4—C24	1.560 (3)	C22—H22	0.9500
C4—C5	1.577 (2)	C23—H23	0.9500
C5—C6	1.534 (2)	C24—H24A	0.9800
C5—C10	1.569 (2)	C24—H24B	0.9800
C5—H5	1.0000	C24—H24C	0.9800
C6—C7	1.537 (2)	C25—H25A	0.9800
C6—H6	1.0000	C25—H25B	0.9800
C7—C8	1.539 (2)	C25—H25C	0.9800
C7—H7	1.0000	C26—H26A	0.9800
C8—C26	1.557 (2)	C26—H26B	0.9800
C8—C9	1.561 (2)	C26—H26C	0.9800
C8—C14	1.570 (2)	C27—C28	1.504 (3)
C9—C11	1.544 (2)	C28—H28A	0.9800
C9—C10	1.571 (2)	C28—H28B	0.9800
C9—H9	1.0000	C28—H28C	0.9800
C10—C19	1.559 (2)	C29—C30	1.504 (3)
C11—C12	1.554 (2)	C30—H30A	0.9800
C11—H11A	0.9900	C30—H30B	0.9800
C11—H11B	0.9900	C30—H30C	0.9800
C27—O2—C6	115.28 (15)	C15—C14—C8	122.44 (13)
C29—O3—C7	117.80 (12)	C13—C14—C8	118.83 (12)
C15—O4—C14	62.14 (9)	O4—C15—C14	59.43 (9)
C16—O5—C17	120.09 (12)	O4—C15—C16	116.61 (14)
C23—O7—C21	105.9 (2)	C14—C15—C16	117.91 (14)
C2—C1—C10	120.74 (16)	O4—C15—H15	116.8
C2—C1—H1	119.6	C14—C15—H15	116.8
C10—C1—H1	119.6	C16—C15—H15	116.8
C1—C2—C3	120.26 (16)	O6—C16—O5	120.32 (15)
C1—C2—H2	119.9	O6—C16—C15	121.52 (16)
C3—C2—H2	119.9	O5—C16—C15	118.11 (14)
O1—C3—C2	121.14 (18)	O5—C17—C20	104.45 (14)
O1—C3—C4	120.21 (19)	O5—C17—C13	110.09 (13)
C2—C3—C4	118.58 (14)	C20—C17—C13	115.47 (15)
C25—C4—C3	109.08 (14)	O5—C17—H17	108.9
C25—C4—C24	108.90 (16)	C20—C17—H17	108.9
C3—C4—C24	103.16 (15)	C13—C17—H17	108.9
C25—C4—C5	114.70 (14)	C13—C18—H18A	109.5
C3—C4—C5	110.96 (14)	C13—C18—H18B	109.5
C24—C4—C5	109.39 (13)	H18A—C18—H18B	109.5
C6—C5—C10	109.77 (12)	C13—C18—H18C	109.5
C6—C5—C4	114.27 (13)	H18A—C18—H18C	109.5
C10—C5—C4	114.05 (12)	H18B—C18—H18C	109.5
C6—C5—H5	106.0	C10—C19—H19A	109.5
C10—C5—H5	106.0	C10—C19—H19B	109.5
C4—C5—H5	106.0	H19A—C19—H19B	109.5
O2—C6—C5	109.22 (12)	C10—C19—H19C	109.5
O2—C6—C7	107.43 (12)	H19A—C19—H19C	109.5
C5—C6—C7	112.10 (12)	H19B—C19—H19C	109.5
O2—C6—H6	109.3	C21—C20—C22	106.0 (3)
C5—C6—H6	109.3	C21—C20—C17	125.3 (3)
C7—C6—H6	109.3	C22—C20—C17	128.7 (2)
O3—C7—C6	108.21 (12)	C20—C21—O7	110.8 (4)
O3—C7—C8	107.95 (11)	C20—C21—H21	124.6
C6—C7—C8	112.24 (12)	O7—C21—H21	124.6
O3—C7—H7	109.5	C23—C22—C20	106.6 (3)
C6—C7—H7	109.5	C23—C22—H22	126.7
C8—C7—H7	109.5	C20—C22—H22	126.7
C7—C8—C26	108.58 (13)	C22—C23—O7	110.8 (4)
C7—C8—C9	108.85 (12)	C22—C23—H23	124.6
C26—C8—C9	113.32 (11)	O7—C23—H23	124.6
C7—C8—C14	110.18 (11)	C4—C24—H24A	109.5
C26—C8—C14	106.74 (12)	C4—C24—H24B	109.5
C9—C8—C14	109.15 (12)	H24A—C24—H24B	109.5
C11—C9—C8	110.69 (12)	C4—C24—H24C	109.5
C11—C9—C10	114.45 (11)	H24A—C24—H24C	109.5
C8—C9—C10	114.98 (12)	H24B—C24—H24C	109.5
C11—C9—H9	105.2	C4—C25—H25A	109.5
C8—C9—H9	105.2	C4—C25—H25B	109.5
C10—C9—H9	105.2	H25A—C25—H25B	109.5
C1—C10—C19	105.40 (12)	C4—C25—H25C	109.5
C1—C10—C5	105.61 (13)	H25A—C25—H25C	109.5
C19—C10—C5	113.12 (13)	H25B—C25—H25C	109.5
C1—C10—C9	108.83 (13)	C8—C26—H26A	109.5
C19—C10—C9	114.95 (13)	C8—C26—H26B	109.5
C5—C10—C9	108.42 (11)	H26A—C26—H26B	109.5
C9—C11—C12	114.64 (12)	C8—C26—H26C	109.5
C9—C11—H11A	108.6	H26A—C26—H26C	109.5
C12—C11—H11A	108.6	H26B—C26—H26C	109.5
C9—C11—H11B	108.6	O8—C27—O2	123.16 (18)
C12—C11—H11B	108.6	O8—C27—C28	125.8 (2)
H11A—C11—H11B	107.6	O2—C27—C28	111.0 (2)
C13—C12—C11	113.60 (13)	C27—C28—H28A	109.5
C13—C12—H12A	108.8	C27—C28—H28B	109.5
C11—C12—H12A	108.8	H28A—C28—H28B	109.5
C13—C12—H12B	108.8	C27—C28—H28C	109.5
C11—C12—H12B	108.8	H28A—C28—H28C	109.5
H12A—C12—H12B	107.7	H28B—C28—H28C	109.5
C14—C13—C12	106.49 (13)	O9—C29—O3	123.71 (16)
C14—C13—C18	112.10 (13)	O9—C29—C30	126.10 (15)
C12—C13—C18	113.16 (13)	O3—C29—C30	110.19 (14)
C14—C13—C17	106.91 (13)	C29—C30—H30A	109.5
C12—C13—C17	109.19 (13)	C29—C30—H30B	109.5
C18—C13—C17	108.77 (14)	H30A—C30—H30B	109.5
O4—C14—C15	58.43 (9)	C29—C30—H30C	109.5
O4—C14—C13	112.54 (12)	H30A—C30—H30C	109.5
C15—C14—C13	115.33 (12)	H30B—C30—H30C	109.5
O4—C14—C8	113.27 (12)
C10—C1—C2—C3	−0.8 (3)	C11—C12—C13—C18	66.3 (2)
C1—C2—C3—O1	151.7 (2)	C11—C12—C13—C17	−172.40 (15)
C1—C2—C3—C4	−31.5 (3)	C15—O4—C14—C13	−106.78 (14)
O1—C3—C4—C25	−41.8 (2)	C15—O4—C14—C8	114.90 (14)
C2—C3—C4—C25	141.42 (17)	C12—C13—C14—O4	−90.70 (14)
O1—C3—C4—C24	73.9 (2)	C18—C13—C14—O4	145.05 (12)
C2—C3—C4—C24	−102.93 (18)	C17—C13—C14—O4	25.94 (16)
O1—C3—C4—C5	−169.06 (17)	C12—C13—C14—C15	−155.18 (13)
C2—C3—C4—C5	14.1 (2)	C18—C13—C14—C15	80.56 (16)
C25—C4—C5—C6	33.94 (19)	C17—C13—C14—C15	−38.54 (18)
C3—C4—C5—C6	158.10 (13)	C12—C13—C14—C8	45.10 (17)
C24—C4—C5—C6	−88.73 (17)	C18—C13—C14—C8	−79.16 (16)
C25—C4—C5—C10	−93.47 (17)	C17—C13—C14—C8	161.74 (13)
C3—C4—C5—C10	30.69 (18)	C7—C8—C14—O4	−95.19 (14)
C24—C4—C5—C10	143.86 (15)	C26—C8—C14—O4	22.52 (16)
C27—O2—C6—C5	−157.85 (14)	C9—C8—C14—O4	145.34 (12)
C27—O2—C6—C7	80.34 (16)	C7—C8—C14—C15	−28.89 (19)
C10—C5—C6—O2	−178.48 (11)	C26—C8—C14—C15	88.82 (16)
C4—C5—C6—O2	51.94 (16)	C9—C8—C14—C15	−148.36 (14)
C10—C5—C6—C7	−59.54 (15)	C7—C8—C14—C13	129.32 (13)
C4—C5—C6—C7	170.89 (12)	C26—C8—C14—C13	−112.97 (14)
C29—O3—C7—C6	−103.01 (14)	C9—C8—C14—C13	9.85 (17)
C29—O3—C7—C8	135.29 (13)	C14—O4—C15—C16	108.19 (15)
O2—C6—C7—O3	59.79 (15)	C13—C14—C15—O4	101.94 (14)
C5—C6—C7—O3	−60.21 (15)	C8—C14—C15—O4	−99.15 (15)
O2—C6—C7—C8	178.81 (12)	O4—C14—C15—C16	−106.01 (16)
C5—C6—C7—C8	58.81 (16)	C13—C14—C15—C16	−4.1 (2)
O3—C7—C8—C26	−170.06 (11)	C8—C14—C15—C16	154.85 (14)
C6—C7—C8—C26	70.76 (15)	C17—O5—C16—O6	172.96 (16)
O3—C7—C8—C9	66.16 (14)	C17—O5—C16—C15	−4.3 (2)
C6—C7—C8—C9	−53.01 (16)	O4—C15—C16—O6	143.88 (16)
O3—C7—C8—C14	−53.49 (14)	C14—C15—C16—O6	−148.35 (16)
C6—C7—C8—C14	−172.67 (12)	O4—C15—C16—O5	−38.9 (2)
C7—C8—C9—C11	−175.38 (12)	C14—C15—C16—O5	28.8 (2)
C26—C8—C9—C11	63.71 (16)	C16—O5—C17—C20	−166.21 (16)
C14—C8—C9—C11	−55.09 (15)	C16—O5—C17—C13	−41.7 (2)
C7—C8—C9—C10	53.01 (15)	C14—C13—C17—O5	61.47 (17)
C26—C8—C9—C10	−67.90 (16)	C12—C13—C17—O5	176.30 (14)
C14—C8—C9—C10	173.30 (12)	C18—C13—C17—O5	−59.77 (18)
C2—C1—C10—C19	−75.97 (19)	C14—C13—C17—C20	179.41 (16)
C2—C1—C10—C5	44.02 (19)	C12—C13—C17—C20	−65.8 (2)
C2—C1—C10—C9	160.24 (15)	C18—C13—C17—C20	58.2 (2)
C6—C5—C10—C1	172.32 (12)	O5—C17—C20—C21	−135.9 (2)
C4—C5—C10—C1	−57.99 (16)	C13—C17—C20—C21	103.1 (3)
C6—C5—C10—C19	−72.91 (15)	O5—C17—C20—C22	41.4 (3)
C4—C5—C10—C19	56.78 (17)	C13—C17—C20—C22	−79.6 (2)
C6—C5—C10—C9	55.81 (15)	C22—C20—C21—O7	1.5 (3)
C4—C5—C10—C9	−174.49 (12)	C17—C20—C21—O7	179.3 (2)
C11—C9—C10—C1	61.00 (17)	C23—O7—C21—C20	−2.0 (3)
C8—C9—C10—C1	−169.21 (12)	C21—C20—C22—C23	−0.3 (3)
C11—C9—C10—C19	−56.92 (18)	C17—C20—C22—C23	−178.1 (2)
C8—C9—C10—C19	72.88 (16)	C20—C22—C23—O7	−0.9 (3)
C11—C9—C10—C5	175.40 (13)	C21—O7—C23—C22	1.8 (4)
C8—C9—C10—C5	−54.81 (16)	C6—O2—C27—O8	2.3 (3)
C8—C9—C11—C12	43.91 (19)	C6—O2—C27—C28	−177.72 (17)
C10—C9—C11—C12	175.79 (14)	C7—O3—C29—O9	2.3 (2)
C9—C11—C12—C13	14.2 (2)	C7—O3—C29—C30	−177.55 (13)
C11—C12—C13—C14	−57.29 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1i	0.99	2.59	3.410 (3)	141
C18—H18C···O1i	0.98	2.68	3.571 (2)	152
C18—H18B···O6ii	0.98	2.56	3.497 (2)	160
C22—H22···O6ii	0.95	2.69	3.601 (3)	162
C24—H24B···O2	0.98	2.40	3.066 (3)	125
C25—H25C···O2	0.98	2.50	3.112 (2)	121
C5—H5···O3	1.00	2.50	2.931 (2)	105
C9—H9···O3	1.00	2.55	2.944 (2)	103
C18—H18B···O5	0.98	2.45	2.934 (2)	110
C7—H7···O9	1.00	2.33	2.735 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O1i	0.99	2.59	3.410 (3)	141
C18—H18C⋯O1i	0.98	2.68	3.571 (2)	152
C18—H18B⋯O6ii	0.98	2.56	3.497 (2)	160
C22—H22⋯O6ii	0.95	2.69	3.601 (3)	162
C24—H24B⋯O2	0.98	2.40	3.066 (3)	125
C25—H25C⋯O2	0.98	2.50	3.112 (2)	121
C5—H5⋯O3	1.00	2.50	2.931 (2)	105
C9—H9⋯O3	1.00	2.55	2.944 (2)	103
C18—H18B⋯O5	0.98	2.45	2.934 (2)	110
C7—H7⋯O9	1.00	2.33	2.735 (2)	103

Symmetry codes: (i) ; (ii) .