(20S*,24S*)-25-Hy-droxy-20,24-ep-oxy-A-homo-4-oxadammaran-3-one (Chrysura) isolated from the leaves of Walsura chrysogyne.

The title dammarane triterpenoid, C(30)H(50)O(4), assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclo-hexane rings adopt chair conformations. The cyclo-pentane and tetra-hydro-furan rings have envelope conformations; their mean planes make a dihedral angle of 13.1 (3)°, indicating that the rings are only slightly tilted with respect to each other. There is an intra-molecular C-H⋯O hydrogen bond in the mol-ecule, which forms S(6) and S(7) ring motifs. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming chains propagating along [001] which stack along the b-axis direction.

Related literature

For related structures, see: Pan et al. (2010 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶). For the biological activity of related compounds, see: Burkill (1966 ▶); Hegnauer (1990 ▶); Fujiwara et al. (1982 ▶).

Experimental

Crystal data

C30H50O4

M = 474.70

Orthorhombic,

a = 6.9881 (1) Å

b = 11.0108 (2) Å

c = 34.9733 (7) Å

V = 2691.01 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.59 mm−1

T = 100 K

0.40 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.801, T max = 0.960

48305 measured reflections

5058 independent reflections

5040 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.092

wR(F 2) = 0.233

S = 1.21

5058 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.38 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047337/su2332sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047337/su2332Isup2.hkl

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

C30H50O4	F(000) = 1048
Mr = 474.70	Dx = 1.172 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9811 reflections
a = 6.9881 (1) Å	θ = 3–69°
b = 11.0108 (2) Å	µ = 0.59 mm−1
c = 34.9733 (7) Å	T = 100 K
V = 2691.01 (8) Å3	Needle, colourless
Z = 4	0.40 × 0.08 × 0.07 mm

Bruker APEXII CCD diffractometer	5058 independent reflections
Radiation source: fine-focus sealed tube	5040 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 69.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→8
Tmin = 0.801, Tmax = 0.960	k = −13→13
48305 measured reflections	l = −41→42

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.092	w = 1/[σ2(Fo2) + (0.0677P)2 + 8.7996P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.233	(Δ/σ)max < 0.001
S = 1.21	Δρmax = 0.47 e Å−3
5058 reflections	Δρmin = −0.38 e Å−3
316 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0021 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881
Secondary atom site location: difference Fourier map	Flack parameter: 0.1 (5)

Experimental. The needle-shape crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

	x	y	z	Uiso*/Ueq
O31	0.0510 (6)	0.8536 (4)	1.00267 (11)	0.0404 (10)
O32	0.2497 (5)	0.9976 (3)	0.98533 (9)	0.0275 (8)
O33	0.3411 (5)	1.0371 (3)	0.66313 (9)	0.0277 (8)
O34	0.2551 (6)	0.9264 (3)	0.56801 (10)	0.0345 (9)
H34A	0.2593	0.9556	0.5464	0.052*
C1	0.1697 (7)	0.8667 (4)	0.90988 (13)	0.0237 (10)
H1A	0.0311	0.8708	0.9109	0.028*
H1B	0.2030	0.8116	0.8893	0.028*
C2	0.2412 (9)	0.8102 (5)	0.94789 (14)	0.0306 (12)
H2A	0.1914	0.7284	0.9505	0.037*
H2B	0.3799	0.8056	0.9477	0.037*
C3	0.1774 (8)	0.8847 (5)	0.98059 (13)	0.0287 (12)
C4	0.4229 (7)	1.0448 (5)	0.96570 (13)	0.0236 (10)
C5	0.4357 (7)	1.0211 (4)	0.92154 (13)	0.0209 (10)
H5A	0.5138	0.9478	0.9185	0.025*
C6	0.5520 (6)	1.1256 (4)	0.90319 (13)	0.0203 (10)
H6A	0.4782	1.2001	0.9046	0.024*
H6B	0.6691	1.1376	0.9176	0.024*
C7	0.6018 (7)	1.0995 (4)	0.86170 (13)	0.0204 (9)
H7A	0.6752	1.0249	0.8603	0.024*
H7B	0.6808	1.1648	0.8518	0.024*
C8	0.4216 (6)	1.0873 (4)	0.83692 (12)	0.0183 (9)
C9	0.2945 (6)	0.9860 (4)	0.85516 (12)	0.0165 (9)
H9A	0.3707	0.9117	0.8529	0.020*
C10	0.2470 (7)	0.9967 (4)	0.89916 (12)	0.0195 (9)
C11	0.1148 (6)	0.9619 (4)	0.83075 (13)	0.0190 (9)
H11A	0.0369	1.0348	0.8302	0.023*
H11B	0.0400	0.8981	0.8426	0.023*
C12	0.1632 (7)	0.9243 (4)	0.78936 (13)	0.0208 (10)
H12A	0.2262	0.8458	0.7894	0.025*
H12B	0.0463	0.9173	0.7746	0.025*
C13	0.2941 (7)	1.0189 (4)	0.77122 (12)	0.0203 (10)
H13A	0.2229	1.0956	0.7717	0.024*
C14	0.4758 (6)	1.0405 (4)	0.79509 (13)	0.0167 (9)
C15	0.5831 (7)	1.1312 (4)	0.76941 (13)	0.0235 (10)
H15A	0.7189	1.1311	0.7751	0.028*
H15B	0.5337	1.2128	0.7728	0.028*
C16	0.5460 (7)	1.0854 (5)	0.72793 (13)	0.0217 (10)
H16A	0.6548	1.0393	0.7187	0.026*
H16B	0.5246	1.1535	0.7108	0.026*
C17	0.3625 (6)	1.0024 (4)	0.72988 (13)	0.0191 (10)
H17A	0.4059	0.9182	0.7274	0.023*
C30	0.5988 (7)	0.9245 (4)	0.79638 (13)	0.0220 (10)
H30A	0.6375	0.9032	0.7709	0.033*
H30B	0.5254	0.8593	0.8072	0.033*
H30C	0.7101	0.9388	0.8118	0.033*
C19	0.0918 (7)	1.0887 (4)	0.90822 (13)	0.0226 (10)
H19A	0.0491	1.0775	0.9341	0.034*
H19B	−0.0139	1.0775	0.8910	0.034*
H19C	0.1421	1.1693	0.9053	0.034*
C20	0.2217 (7)	1.0257 (4)	0.69762 (13)	0.0202 (10)
C21	0.1120 (7)	1.1431 (5)	0.70141 (14)	0.0261 (11)
H21A	0.2003	1.2093	0.7042	0.039*
H21B	0.0308	1.1393	0.7235	0.039*
H21C	0.0353	1.1554	0.6790	0.039*
C22	0.0884 (7)	0.9175 (5)	0.68812 (14)	0.0245 (10)
H22A	0.1426	0.8414	0.6970	0.029*
H22B	−0.0370	0.9283	0.6995	0.029*
C23	0.0774 (8)	0.9211 (4)	0.64427 (14)	0.0255 (10)
H23A	0.0413	0.8428	0.6338	0.031*
H23B	−0.0120	0.9824	0.6355	0.031*
C24	0.2804 (7)	0.9535 (4)	0.63416 (14)	0.0257 (11)
H24A	0.3588	0.8800	0.6362	0.031*
C25	0.3219 (8)	1.0139 (5)	0.59506 (15)	0.0294 (11)
C26	0.5357 (9)	1.0307 (6)	0.59086 (17)	0.0382 (14)
H26A	0.5632	1.0659	0.5664	0.057*
H26B	0.5981	0.9533	0.5929	0.057*
H26C	0.5815	1.0835	0.6107	0.057*
C27	0.2159 (9)	1.1313 (5)	0.58997 (15)	0.0351 (13)
H27A	0.2411	1.1632	0.5649	0.053*
H27B	0.2579	1.1886	0.6089	0.053*
H27C	0.0811	1.1173	0.5928	0.053*
C28	0.5949 (8)	0.9895 (6)	0.98605 (15)	0.0344 (12)
H28A	0.5901	1.0098	1.0127	0.052*
H28C	0.7106	1.0210	0.9751	0.052*
H28D	0.5923	0.9028	0.9832	0.052*
C29	0.4088 (9)	1.1798 (5)	0.97708 (14)	0.0302 (12)
H29C	0.3941	1.1862	1.0043	0.045*
H29D	0.3003	1.2159	0.9647	0.045*
H29A	0.5232	1.2213	0.9694	0.045*
C18	0.3211 (7)	1.2099 (4)	0.83435 (14)	0.0237 (10)
H18A	0.2779	1.2337	0.8593	0.036*
H18B	0.2133	1.2036	0.8174	0.036*
H18C	0.4087	1.2696	0.8247	0.036*

	U11	U22	U33	U12	U13	U23
O31	0.043 (2)	0.049 (2)	0.029 (2)	−0.013 (2)	0.0095 (18)	0.0026 (18)
O32	0.0313 (18)	0.0309 (19)	0.0202 (15)	−0.0033 (17)	0.0022 (14)	0.0007 (14)
O33	0.0307 (18)	0.0328 (19)	0.0195 (16)	−0.0063 (15)	0.0047 (14)	0.0008 (15)
O34	0.046 (2)	0.035 (2)	0.0225 (17)	−0.0042 (19)	−0.0020 (17)	0.0001 (15)
C1	0.021 (2)	0.028 (3)	0.022 (2)	−0.006 (2)	−0.0023 (19)	0.001 (2)
C2	0.036 (3)	0.031 (3)	0.025 (2)	−0.006 (2)	0.002 (2)	0.006 (2)
C3	0.034 (3)	0.036 (3)	0.017 (2)	−0.002 (2)	−0.005 (2)	0.010 (2)
C4	0.025 (2)	0.027 (2)	0.020 (2)	−0.001 (2)	−0.003 (2)	0.0022 (19)
C5	0.019 (2)	0.022 (2)	0.021 (2)	0.0041 (19)	−0.0062 (19)	−0.0019 (19)
C6	0.012 (2)	0.028 (2)	0.021 (2)	0.0015 (19)	−0.0016 (17)	−0.0021 (19)
C7	0.016 (2)	0.023 (2)	0.022 (2)	0.0068 (19)	−0.0033 (18)	−0.0054 (18)
C8	0.016 (2)	0.022 (2)	0.017 (2)	−0.0077 (19)	0.0012 (18)	−0.0014 (18)
C9	0.011 (2)	0.023 (2)	0.0159 (19)	0.0030 (18)	0.0004 (16)	−0.0053 (18)
C10	0.016 (2)	0.023 (2)	0.019 (2)	−0.0015 (19)	0.0020 (17)	−0.0020 (18)
C11	0.013 (2)	0.021 (2)	0.022 (2)	−0.0026 (17)	−0.0007 (17)	0.0058 (18)
C12	0.021 (2)	0.023 (2)	0.018 (2)	−0.0068 (19)	−0.0034 (18)	−0.0029 (18)
C13	0.024 (2)	0.018 (2)	0.019 (2)	−0.0029 (19)	−0.0040 (19)	0.0013 (17)
C14	0.016 (2)	0.017 (2)	0.017 (2)	−0.0048 (17)	−0.0023 (17)	−0.0003 (17)
C15	0.022 (2)	0.026 (2)	0.023 (2)	−0.004 (2)	0.002 (2)	0.0021 (19)
C16	0.013 (2)	0.028 (2)	0.024 (2)	−0.0043 (19)	0.0007 (18)	0.000 (2)
C17	0.019 (2)	0.015 (2)	0.023 (2)	0.0042 (18)	−0.0006 (18)	−0.0004 (18)
C30	0.016 (2)	0.026 (2)	0.024 (2)	0.0000 (19)	−0.0011 (19)	−0.0006 (19)
C19	0.019 (2)	0.029 (2)	0.020 (2)	0.000 (2)	0.0014 (18)	−0.0009 (19)
C20	0.019 (2)	0.021 (2)	0.021 (2)	0.0000 (19)	−0.0021 (18)	0.0050 (18)
C21	0.022 (2)	0.031 (3)	0.025 (2)	−0.003 (2)	−0.005 (2)	0.004 (2)
C22	0.023 (2)	0.027 (2)	0.023 (2)	−0.001 (2)	0.000 (2)	−0.0035 (19)
C23	0.028 (3)	0.023 (2)	0.026 (2)	−0.007 (2)	0.000 (2)	0.002 (2)
C24	0.030 (3)	0.024 (2)	0.023 (2)	−0.004 (2)	0.000 (2)	0.0011 (19)
C25	0.032 (3)	0.031 (3)	0.025 (2)	−0.002 (2)	0.000 (2)	0.000 (2)
C26	0.040 (3)	0.043 (3)	0.032 (3)	−0.006 (3)	−0.007 (2)	0.007 (3)
C27	0.040 (3)	0.040 (3)	0.025 (2)	0.003 (3)	0.002 (2)	0.007 (2)
C28	0.033 (3)	0.045 (3)	0.025 (2)	0.000 (3)	−0.013 (2)	0.000 (2)
C29	0.034 (3)	0.035 (3)	0.021 (2)	−0.010 (2)	0.002 (2)	−0.006 (2)
C18	0.023 (2)	0.023 (2)	0.025 (2)	−0.002 (2)	0.000 (2)	−0.004 (2)

O31—C3	1.223 (7)	C15—C16	1.558 (6)
O32—C3	1.352 (7)	C15—H15A	0.9700
O32—C4	1.485 (6)	C15—H15B	0.9700
O33—C24	1.433 (6)	C16—C17	1.576 (6)
O33—C20	1.472 (5)	C16—H16A	0.9700
O34—C25	1.428 (6)	C16—H16B	0.9700
O34—H34A	0.8200	C17—C20	1.519 (6)
C1—C2	1.551 (7)	C17—H17A	0.9800
C1—C10	1.576 (7)	C30—H30A	0.9600
C1—H1A	0.9700	C30—H30B	0.9600
C1—H1B	0.9700	C30—H30C	0.9600
C2—C3	1.477 (8)	C19—H19A	0.9600
C2—H2A	0.9700	C19—H19B	0.9600
C2—H2B	0.9700	C19—H19C	0.9600
C4—C28	1.523 (7)	C20—C21	1.509 (7)
C4—C29	1.542 (7)	C20—C22	1.548 (7)
C4—C5	1.569 (6)	C21—H21A	0.9600
C5—C6	1.548 (7)	C21—H21B	0.9600
C5—C10	1.557 (6)	C21—H21C	0.9600
C5—H5A	0.9800	C22—C23	1.536 (6)
C6—C7	1.520 (6)	C22—H22A	0.9700
C6—H6A	0.9700	C22—H22B	0.9700
C6—H6B	0.9700	C23—C24	1.505 (7)
C7—C8	1.535 (6)	C23—H23A	0.9700
C7—H7A	0.9700	C23—H23B	0.9700
C7—H7B	0.9700	C24—C25	1.548 (7)
C8—C18	1.524 (6)	C24—H24A	0.9800
C8—C9	1.562 (6)	C25—C27	1.500 (8)
C8—C14	1.597 (6)	C25—C26	1.513 (8)
C9—C11	1.541 (6)	C26—H26A	0.9600
C9—C10	1.579 (6)	C26—H26B	0.9600
C9—H9A	0.9800	C26—H26C	0.9600
C10—C19	1.518 (6)	C27—H27A	0.9600
C11—C12	1.543 (6)	C27—H27B	0.9600
C11—H11A	0.9700	C27—H27C	0.9600
C11—H11B	0.9700	C28—H28A	0.9600
C12—C13	1.525 (6)	C28—H28C	0.9600
C12—H12A	0.9700	C28—H28D	0.9600
C12—H12B	0.9700	C29—H29C	0.9600
C13—C17	1.533 (6)	C29—H29D	0.9600
C13—C14	1.538 (6)	C29—H29A	0.9600
C13—H13A	0.9800	C18—H18A	0.9600
C14—C15	1.538 (6)	C18—H18B	0.9600
C14—C30	1.540 (6)	C18—H18C	0.9600
C3—O32—C4	124.7 (4)	C15—C16—C17	106.4 (4)
C24—O33—C20	110.9 (4)	C15—C16—H16A	110.4
C25—O34—H34A	109.5	C17—C16—H16A	110.4
C2—C1—C10	117.2 (4)	C15—C16—H16B	110.4
C2—C1—H1A	108.0	C17—C16—H16B	110.4
C10—C1—H1A	108.0	H16A—C16—H16B	108.6
C2—C1—H1B	108.0	C20—C17—C13	118.6 (4)
C10—C1—H1B	108.0	C20—C17—C16	113.4 (4)
H1A—C1—H1B	107.2	C13—C17—C16	103.0 (4)
C3—C2—C1	110.1 (4)	C20—C17—H17A	107.0
C3—C2—H2A	109.6	C13—C17—H17A	107.0
C1—C2—H2A	109.6	C16—C17—H17A	107.0
C3—C2—H2B	109.6	C14—C30—H30A	109.5
C1—C2—H2B	109.6	C14—C30—H30B	109.5
H2A—C2—H2B	108.2	H30A—C30—H30B	109.5
O31—C3—O32	116.8 (5)	C14—C30—H30C	109.5
O31—C3—C2	123.5 (5)	H30A—C30—H30C	109.5
O32—C3—C2	119.6 (4)	H30B—C30—H30C	109.5
O32—C4—C28	106.7 (4)	C10—C19—H19A	109.5
O32—C4—C29	99.5 (4)	C10—C19—H19B	109.5
C28—C4—C29	108.4 (4)	H19A—C19—H19B	109.5
O32—C4—C5	116.3 (4)	C10—C19—H19C	109.5
C28—C4—C5	110.4 (4)	H19A—C19—H19C	109.5
C29—C4—C5	114.7 (4)	H19B—C19—H19C	109.5
C6—C5—C10	111.4 (4)	O33—C20—C21	106.7 (4)
C6—C5—C4	108.3 (4)	O33—C20—C17	104.8 (4)
C10—C5—C4	118.4 (4)	C21—C20—C17	114.1 (4)
C6—C5—H5A	106.0	O33—C20—C22	103.3 (4)
C10—C5—H5A	106.0	C21—C20—C22	111.9 (4)
C4—C5—H5A	106.0	C17—C20—C22	114.8 (4)
C7—C6—C5	112.1 (4)	C20—C21—H21A	109.5
C7—C6—H6A	109.2	C20—C21—H21B	109.5
C5—C6—H6A	109.2	H21A—C21—H21B	109.5
C7—C6—H6B	109.2	C20—C21—H21C	109.5
C5—C6—H6B	109.2	H21A—C21—H21C	109.5
H6A—C6—H6B	107.9	H21B—C21—H21C	109.5
C6—C7—C8	111.6 (4)	C23—C22—C20	103.0 (4)
C6—C7—H7A	109.3	C23—C22—H22A	111.2
C8—C7—H7A	109.3	C20—C22—H22A	111.2
C6—C7—H7B	109.3	C23—C22—H22B	111.2
C8—C7—H7B	109.3	C20—C22—H22B	111.2
H7A—C7—H7B	108.0	H22A—C22—H22B	109.1
C18—C8—C7	109.5 (4)	C24—C23—C22	101.1 (4)
C18—C8—C9	113.2 (4)	C24—C23—H23A	111.5
C7—C8—C9	107.4 (4)	C22—C23—H23A	111.5
C18—C8—C14	109.9 (4)	C24—C23—H23B	111.5
C7—C8—C14	110.5 (4)	C22—C23—H23B	111.5
C9—C8—C14	106.2 (3)	H23A—C23—H23B	109.4
C11—C9—C8	111.1 (4)	O33—C24—C23	105.4 (4)
C11—C9—C10	112.4 (3)	O33—C24—C25	107.1 (4)
C8—C9—C10	117.7 (4)	C23—C24—C25	119.1 (4)
C11—C9—H9A	104.7	O33—C24—H24A	108.3
C8—C9—H9A	104.7	C23—C24—H24A	108.3
C10—C9—H9A	104.7	C25—C24—H24A	108.3
C19—C10—C5	112.6 (4)	O34—C25—C27	110.0 (4)
C19—C10—C1	108.2 (4)	O34—C25—C26	109.9 (5)
C5—C10—C1	109.1 (4)	C27—C25—C26	111.7 (5)
C19—C10—C9	113.8 (4)	O34—C25—C24	103.6 (4)
C5—C10—C9	109.0 (4)	C27—C25—C24	112.5 (4)
C1—C10—C9	103.7 (4)	C26—C25—C24	108.8 (4)
C9—C11—C12	112.8 (4)	C25—C26—H26A	109.5
C9—C11—H11A	109.0	C25—C26—H26B	109.5
C12—C11—H11A	109.0	H26A—C26—H26B	109.5
C9—C11—H11B	109.0	C25—C26—H26C	109.5
C12—C11—H11B	109.0	H26A—C26—H26C	109.5
H11A—C11—H11B	107.8	H26B—C26—H26C	109.5
C13—C12—C11	109.8 (4)	C25—C27—H27A	109.5
C13—C12—H12A	109.7	C25—C27—H27B	109.5
C11—C12—H12A	109.7	H27A—C27—H27B	109.5
C13—C12—H12B	109.7	C25—C27—H27C	109.5
C11—C12—H12B	109.7	H27A—C27—H27C	109.5
H12A—C12—H12B	108.2	H27B—C27—H27C	109.5
C12—C13—C17	119.9 (4)	C4—C28—H28A	109.5
C12—C13—C14	112.1 (4)	C4—C28—H28C	109.5
C17—C13—C14	105.8 (4)	H28A—C28—H28C	109.5
C12—C13—H13A	106.0	C4—C28—H28D	109.5
C17—C13—H13A	106.0	H28A—C28—H28D	109.5
C14—C13—H13A	106.0	H28C—C28—H28D	109.5
C13—C14—C15	100.7 (4)	C4—C29—H29C	109.5
C13—C14—C30	110.4 (4)	C4—C29—H29D	109.5
C15—C14—C30	106.5 (4)	H29C—C29—H29D	109.5
C13—C14—C8	110.6 (4)	C4—C29—H29A	109.5
C15—C14—C8	116.2 (4)	H29C—C29—H29A	109.5
C30—C14—C8	111.9 (4)	H29D—C29—H29A	109.5
C14—C15—C16	104.6 (4)	C8—C18—H18A	109.5
C14—C15—H15A	110.8	C8—C18—H18B	109.5
C16—C15—H15A	110.8	H18A—C18—H18B	109.5
C14—C15—H15B	110.8	C8—C18—H18C	109.5
C16—C15—H15B	110.8	H18A—C18—H18C	109.5
H15A—C15—H15B	108.9	H18B—C18—H18C	109.5
C10—C1—C2—C3	63.3 (6)	C17—C13—C14—C15	44.3 (4)
C4—O32—C3—O31	169.9 (4)	C12—C13—C14—C30	64.5 (5)
C4—O32—C3—C2	−15.1 (7)	C17—C13—C14—C30	−67.9 (5)
C1—C2—C3—O31	107.2 (6)	C12—C13—C14—C8	−59.9 (5)
C1—C2—C3—O32	−67.5 (6)	C17—C13—C14—C8	167.7 (4)
C3—O32—C4—C28	−76.9 (5)	C18—C8—C14—C13	−63.3 (5)
C3—O32—C4—C29	170.5 (4)	C7—C8—C14—C13	175.7 (4)
C3—O32—C4—C5	46.8 (6)	C9—C8—C14—C13	59.5 (5)
O32—C4—C5—C6	150.4 (4)	C18—C8—C14—C15	50.6 (5)
C28—C4—C5—C6	−87.9 (5)	C7—C8—C14—C15	−70.4 (5)
C29—C4—C5—C6	34.9 (6)	C9—C8—C14—C15	173.5 (4)
O32—C4—C5—C10	22.4 (6)	C18—C8—C14—C30	173.2 (4)
C28—C4—C5—C10	144.1 (4)	C7—C8—C14—C30	52.2 (5)
C29—C4—C5—C10	−93.1 (5)	C9—C8—C14—C30	−64.0 (4)
C10—C5—C6—C7	−58.1 (5)	C13—C14—C15—C16	−38.9 (4)
C4—C5—C6—C7	170.0 (4)	C30—C14—C15—C16	76.3 (4)
C5—C6—C7—C8	62.3 (5)	C8—C14—C15—C16	−158.3 (4)
C6—C7—C8—C18	67.2 (5)	C14—C15—C16—C17	20.4 (5)
C6—C7—C8—C9	−56.1 (5)	C12—C13—C17—C20	74.5 (6)
C6—C7—C8—C14	−171.5 (4)	C14—C13—C17—C20	−157.7 (4)
C18—C8—C9—C11	62.4 (5)	C12—C13—C17—C16	−159.3 (4)
C7—C8—C9—C11	−176.6 (3)	C14—C13—C17—C16	−31.5 (4)
C14—C8—C9—C11	−58.3 (4)	C15—C16—C17—C20	136.0 (4)
C18—C8—C9—C10	−69.2 (5)	C15—C16—C17—C13	6.5 (5)
C7—C8—C9—C10	51.7 (5)	C24—O33—C20—C21	−113.7 (4)
C14—C8—C9—C10	170.0 (4)	C24—O33—C20—C17	125.0 (4)
C6—C5—C10—C19	−78.2 (5)	C24—O33—C20—C22	4.4 (5)
C4—C5—C10—C19	48.3 (6)	C13—C17—C20—O33	164.2 (4)
C6—C5—C10—C1	161.6 (4)	C16—C17—C20—O33	43.1 (5)
C4—C5—C10—C1	−71.9 (5)	C13—C17—C20—C21	47.9 (6)
C6—C5—C10—C9	49.0 (5)	C16—C17—C20—C21	−73.2 (5)
C4—C5—C10—C9	175.6 (4)	C13—C17—C20—C22	−83.2 (5)
C2—C1—C10—C19	−102.1 (5)	C16—C17—C20—C22	155.8 (4)
C2—C1—C10—C5	20.8 (6)	O33—C20—C22—C23	−27.2 (5)
C2—C1—C10—C9	136.8 (4)	C21—C20—C22—C23	87.2 (5)
C11—C9—C10—C19	−53.3 (5)	C17—C20—C22—C23	−140.7 (4)
C8—C9—C10—C19	77.7 (5)	C20—C22—C23—C24	39.0 (5)
C11—C9—C10—C5	−179.9 (4)	C20—O33—C24—C23	20.8 (5)
C8—C9—C10—C5	−48.9 (5)	C20—O33—C24—C25	148.5 (4)
C11—C9—C10—C1	64.0 (5)	C22—C23—C24—O33	−37.0 (5)
C8—C9—C10—C1	−165.0 (4)	C22—C23—C24—C25	−157.1 (4)
C8—C9—C11—C12	58.0 (5)	O33—C24—C25—O34	−179.1 (4)
C10—C9—C11—C12	−167.7 (4)	C23—C24—C25—O34	−59.9 (6)
C9—C11—C12—C13	−54.2 (5)	O33—C24—C25—C27	−60.4 (6)
C11—C12—C13—C17	−179.8 (4)	C23—C24—C25—C27	58.8 (6)
C11—C12—C13—C14	55.3 (5)	O33—C24—C25—C26	64.0 (6)
C12—C13—C14—C15	176.7 (4)	C23—C24—C25—C26	−176.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O32	0.96	2.44	3.082 (6)	124
O34—H34A···O32i	0.82	2.20	3.010 (5)	170
C26—H26A···O31i	0.96	2.53	3.392 (7)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O32	0.96	2.44	3.082 (6)	124
O34—H34A⋯O32i	0.82	2.20	3.010 (5)	170
C26—H26A⋯O31i	0.96	2.53	3.392 (7)	150

Symmetry code: (i) .