4,5,7,8,17-Penta-hydr-oxy-14,18-dimethyl-6-methyl-ene-3,10-dioxapenta-cyclo-[9.8.0.0.0.0]nona-dec-14-ene-9,16-dione methanol solvate dihydrate.

The title quassinoid compound, C(20)H(24)O(9)·CH(3)OH·2H(2)O, is a natural eurycomanone isolated from the roots of Eurycoma longifolia. The mol-ecules contain a fused five-ring system, with one tetra-hydro-furan ring adopting an envelope conformation, one tetra-hydro-pyran-2-one ring in a screw boat conformation, one cyclo-hexenone ring in a half-chair conformation and two cyclo-hexane rings in chair conformations. Intra-molecular C-H⋯O inter-actions generate S(5) ring motifs and an O-H⋯O inter-action generates an S(7) ring motif. In the crystal, mol-ecules are linked via inter-molecular O-H⋯O inter-actions along the b axis and further stacked along a axis. The absolute configuration of the title compound was inferred from previously solved structures of its analogues.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For quassinoids and bioactivity, see Itokawa et al. (1993 ▶); Chan et al. (1992 ▶); Kardono et al. (1991 ▶); Itokawa et al. (1992 ▶); Morita et al. (1992 ▶); Morita et al. (1993 ▶); Tada et al. (1991 ▶); Ang et al. (1995 ▶); Chan et al. (2004 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H24O9·CH4O·2H2O

M = 476.47

Orthorhombic,

a = 9.1817 (1) Å

b = 10.7806 (2) Å

c = 21.7817 (3) Å

V = 2156.04 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.43 × 0.28 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.950, T max = 0.987

27636 measured reflections

3577 independent reflections

3352 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.09

3577 reflections

307 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010502/at2747sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010502/at2747Isup2.hkl

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

C20H24O9·CH4O·2H2O	F(000) = 1016
Mr = 476.47	Dx = 1.468 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9889 reflections
a = 9.1817 (1) Å	θ = 2.4–30.1°
b = 10.7806 (2) Å	µ = 0.12 mm−1
c = 21.7817 (3) Å	T = 100 K
V = 2156.04 (6) Å3	Block, colourless
Z = 4	0.43 × 0.28 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	3577 independent reflections
Radiation source: fine-focus sealed tube	3352 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.950, Tmax = 0.987	k = −15→15
27636 measured reflections	l = −29→30

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0739P)2 + 1.2123P] where P = (Fo2 + 2Fc2)/3
3577 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The 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.

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 > 2sigma(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	0.1926 (2)	0.29462 (17)	1.07263 (8)	0.0182 (4)
O2	0.3034 (2)	0.07030 (16)	1.05042 (8)	0.0175 (4)
H2	0.3223	0.0997	1.0842	0.026*
O3	0.28241 (19)	−0.14352 (15)	1.00393 (7)	0.0117 (3)
H3	0.2817	−0.0757	1.0210	0.018*
O4	0.22993 (18)	−0.17614 (15)	0.90312 (7)	0.0118 (3)
O5	0.58130 (19)	−0.16373 (15)	0.97902 (7)	0.0129 (3)
H5	0.6465	−0.2146	0.9843	0.019*
O6	0.5152 (2)	−0.13426 (15)	0.77017 (7)	0.0127 (3)
H6	0.4834	−0.2045	0.7648	0.019*
O7	0.78562 (19)	−0.09069 (17)	0.82090 (8)	0.0147 (3)
H7	0.8241	−0.1258	0.8501	0.022*
O8	0.74680 (19)	0.14137 (17)	0.77962 (8)	0.0167 (4)
O9	0.51228 (19)	0.13846 (15)	0.79549 (7)	0.0126 (3)
C1	0.3189 (3)	0.22030 (19)	0.89489 (10)	0.0101 (4)
H1A	0.4255	0.2249	0.8946	0.012*
C2	0.2671 (3)	0.3479 (2)	0.91422 (11)	0.0130 (4)
C3	0.2330 (3)	0.3740 (2)	0.97285 (11)	0.0152 (4)
H3A	0.2023	0.4536	0.9830	0.018*
C4	0.2431 (3)	0.2802 (2)	1.02085 (11)	0.0133 (4)
C5	0.3254 (3)	0.1614 (2)	1.00468 (10)	0.0112 (4)
H5A	0.4296	0.1810	1.0035	0.013*
C6	0.2803 (2)	0.11364 (19)	0.94038 (10)	0.0093 (4)
C7	0.3786 (3)	0.00071 (19)	0.92185 (9)	0.0086 (4)
H7A	0.4783	0.0189	0.9351	0.010*
C8	0.3392 (2)	−0.1308 (2)	0.94491 (9)	0.0094 (4)
C9	0.4726 (3)	−0.21530 (19)	0.93946 (9)	0.0106 (4)
H9A	0.4470	−0.2984	0.9542	0.013*
C10	0.5283 (3)	−0.2248 (2)	0.87386 (10)	0.0108 (4)
C11	0.5208 (3)	−0.10845 (19)	0.83436 (9)	0.0094 (4)
C12	0.6596 (3)	−0.0292 (2)	0.84086 (10)	0.0105 (4)
H12A	0.6718	−0.0059	0.8840	0.013*
C13	0.6438 (3)	0.0881 (2)	0.80244 (10)	0.0118 (4)
C14	0.3716 (3)	0.0779 (2)	0.80774 (10)	0.0104 (4)
H14A	0.3327	0.0472	0.7687	0.012*
C15	0.2754 (3)	0.1834 (2)	0.82945 (10)	0.0119 (4)
H15A	0.1742	0.1576	0.8288	0.014*
H15B	0.2861	0.2540	0.8022	0.014*
C16	0.3828 (3)	−0.0312 (2)	0.85175 (10)	0.0094 (4)
C17	0.2494 (3)	−0.1166 (2)	0.84404 (10)	0.0118 (4)
H17A	0.1638	−0.0687	0.8332	0.014*
H17B	0.2669	−0.1779	0.8123	0.014*
C18	0.2638 (3)	0.4474 (2)	0.86586 (12)	0.0194 (5)
H18A	0.2506	0.5268	0.8850	0.029*
H18B	0.1846	0.4319	0.8381	0.029*
H18C	0.3540	0.4469	0.8436	0.029*
C19	0.1144 (3)	0.0868 (2)	0.94083 (11)	0.0125 (4)
H19A	0.0618	0.1637	0.9423	0.019*
H19B	0.0904	0.0377	0.9762	0.019*
H19C	0.0883	0.0423	0.9043	0.019*
C20	0.5852 (3)	−0.3310 (2)	0.85366 (11)	0.0154 (5)
H20A	0.5908	−0.3992	0.8797	0.018*
H20B	0.6192	−0.3368	0.8136	0.018*
O10	0.9816 (2)	0.5246 (2)	0.75796 (10)	0.0265 (4)
H10	1.0588	0.5227	0.7390	0.040*
C21	0.9754 (3)	0.6332 (3)	0.79372 (14)	0.0273 (6)
H21A	0.8955	0.6276	0.8220	0.041*
H21B	0.9619	0.7037	0.7674	0.041*
H21C	1.0648	0.6424	0.8162	0.041*
O1W	0.9259 (2)	0.8195 (2)	0.91766 (10)	0.0283 (5)
H1W1	1.0216	0.8137	0.9173	0.042*
H2W1	0.8959	0.7574	0.9371	0.042*
O2W	0.8990 (3)	0.3466 (2)	0.84211 (9)	0.0341 (6)
H1W2	0.8346	0.2908	0.8221	0.051*
H2W2	0.9261	0.4012	0.8161	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0210 (9)	0.0187 (8)	0.0150 (8)	0.0028 (7)	0.0020 (7)	−0.0043 (7)
O2	0.0321 (10)	0.0119 (7)	0.0086 (7)	0.0001 (7)	0.0005 (7)	−0.0005 (6)
O3	0.0158 (8)	0.0101 (7)	0.0092 (7)	0.0001 (6)	0.0037 (6)	0.0008 (5)
O4	0.0128 (7)	0.0118 (7)	0.0108 (7)	−0.0035 (6)	−0.0018 (6)	0.0019 (6)
O5	0.0141 (8)	0.0127 (7)	0.0121 (7)	0.0033 (6)	−0.0032 (6)	−0.0012 (6)
O6	0.0206 (8)	0.0112 (7)	0.0063 (6)	−0.0015 (7)	0.0009 (6)	−0.0017 (5)
O7	0.0134 (8)	0.0162 (8)	0.0146 (7)	0.0044 (7)	0.0038 (6)	0.0033 (6)
O8	0.0171 (9)	0.0142 (7)	0.0187 (8)	−0.0025 (7)	0.0036 (7)	0.0023 (6)
O9	0.0142 (8)	0.0098 (7)	0.0136 (7)	−0.0001 (6)	0.0011 (6)	0.0032 (6)
C1	0.0122 (9)	0.0079 (8)	0.0102 (9)	0.0010 (7)	0.0000 (8)	0.0003 (7)
C2	0.0134 (10)	0.0084 (9)	0.0173 (10)	0.0004 (8)	−0.0002 (8)	0.0008 (8)
C3	0.0159 (11)	0.0111 (9)	0.0186 (11)	0.0014 (8)	0.0004 (9)	−0.0026 (8)
C4	0.0139 (11)	0.0100 (9)	0.0159 (10)	0.0005 (8)	−0.0012 (8)	−0.0036 (8)
C5	0.0152 (10)	0.0090 (9)	0.0093 (9)	0.0017 (8)	−0.0001 (8)	−0.0021 (7)
C6	0.0113 (9)	0.0073 (8)	0.0093 (8)	0.0015 (8)	−0.0011 (7)	−0.0009 (7)
C7	0.0107 (9)	0.0080 (8)	0.0071 (8)	0.0001 (7)	−0.0005 (8)	−0.0001 (7)
C8	0.0102 (9)	0.0105 (9)	0.0075 (8)	−0.0004 (8)	0.0010 (7)	−0.0001 (7)
C9	0.0141 (10)	0.0088 (8)	0.0088 (8)	0.0002 (8)	0.0002 (8)	0.0002 (7)
C10	0.0142 (10)	0.0093 (8)	0.0089 (9)	0.0000 (8)	0.0001 (8)	−0.0006 (7)
C11	0.0135 (10)	0.0085 (8)	0.0063 (8)	0.0000 (8)	−0.0001 (8)	−0.0007 (7)
C12	0.0134 (10)	0.0094 (9)	0.0088 (8)	0.0001 (8)	0.0000 (8)	−0.0001 (7)
C13	0.0158 (11)	0.0100 (9)	0.0097 (9)	−0.0014 (8)	0.0013 (8)	−0.0020 (7)
C14	0.0128 (10)	0.0103 (9)	0.0081 (9)	−0.0009 (8)	−0.0012 (8)	0.0008 (7)
C15	0.0151 (10)	0.0112 (9)	0.0094 (9)	−0.0001 (8)	−0.0015 (8)	0.0013 (7)
C16	0.0130 (10)	0.0080 (9)	0.0072 (8)	−0.0012 (8)	−0.0015 (7)	0.0003 (7)
C17	0.0132 (10)	0.0128 (10)	0.0094 (9)	−0.0018 (8)	−0.0015 (8)	0.0003 (7)
C18	0.0282 (13)	0.0100 (9)	0.0199 (11)	0.0022 (9)	−0.0016 (10)	0.0030 (8)
C19	0.0107 (10)	0.0120 (9)	0.0147 (10)	0.0004 (8)	0.0005 (8)	−0.0008 (8)
C20	0.0230 (12)	0.0115 (10)	0.0116 (9)	0.0034 (9)	0.0007 (9)	−0.0010 (8)
O10	0.0200 (10)	0.0323 (11)	0.0272 (10)	−0.0057 (9)	−0.0002 (8)	0.0013 (8)
C21	0.0211 (13)	0.0325 (14)	0.0283 (13)	0.0028 (12)	0.0014 (11)	−0.0004 (12)
O1W	0.0188 (9)	0.0352 (11)	0.0310 (10)	−0.0017 (9)	−0.0018 (8)	0.0140 (9)
O2W	0.0531 (15)	0.0298 (11)	0.0195 (9)	−0.0224 (11)	0.0129 (10)	−0.0082 (8)

O1—C4	1.229 (3)	C9—C10	1.521 (3)
O2—C5	1.414 (3)	C9—H9A	0.9800
O2—H2	0.8200	C10—C20	1.333 (3)
O3—C8	1.394 (3)	C10—C11	1.523 (3)
O3—H3	0.8200	C11—C12	1.541 (3)
O4—C8	1.440 (3)	C11—C16	1.562 (3)
O4—C17	1.449 (3)	C12—C13	1.523 (3)
O5—C9	1.431 (3)	C12—H12A	0.9800
O5—H5	0.8200	C14—C15	1.516 (3)
O6—C11	1.426 (2)	C14—C16	1.520 (3)
O6—H6	0.8200	C14—H14A	0.9800
O7—C12	1.402 (3)	C15—H15A	0.9700
O7—H7	0.8200	C15—H15B	0.9700
O8—C13	1.213 (3)	C16—C17	1.542 (3)
O9—C13	1.333 (3)	C17—H17A	0.9700
O9—C14	1.472 (3)	C17—H17B	0.9700
C1—C2	1.516 (3)	C18—H18A	0.9600
C1—C15	1.533 (3)	C18—H18B	0.9600
C1—C6	1.559 (3)	C18—H18C	0.9600
C1—H1A	0.9800	C19—H19A	0.9600
C2—C3	1.345 (3)	C19—H19B	0.9600
C2—C18	1.503 (3)	C19—H19C	0.9600
C3—C4	1.458 (3)	C20—H20A	0.9300
C3—H3A	0.9300	C20—H20B	0.9300
C4—C5	1.528 (3)	O10—C21	1.408 (4)
C5—C6	1.549 (3)	O10—H10	0.8200
C5—H5A	0.9800	C21—H21A	0.9600
C6—C19	1.551 (3)	C21—H21B	0.9600
C6—C7	1.568 (3)	C21—H21C	0.9600
C7—C8	1.547 (3)	O1W—H1W1	0.8814
C7—C16	1.566 (3)	O1W—H2W1	0.8396
C7—H7A	0.9800	O2W—H1W2	0.9487
C8—C9	1.531 (3)	O2W—H2W2	0.8533
C5—O2—H2	109.5	C10—C11—C16	109.83 (18)
C8—O3—H3	109.5	C12—C11—C16	110.67 (17)
C8—O4—C17	108.97 (16)	O7—C12—C13	107.48 (18)
C9—O5—H5	109.5	O7—C12—C11	113.11 (18)
C11—O6—H6	109.5	C13—C12—C11	109.31 (18)
C12—O7—H7	109.5	O7—C12—H12A	109.0
C13—O9—C14	126.43 (17)	C13—C12—H12A	109.0
C2—C1—C15	114.35 (19)	C11—C12—H12A	109.0
C2—C1—C6	114.97 (18)	O8—C13—O9	117.8 (2)
C15—C1—C6	109.89 (17)	O8—C13—C12	123.0 (2)
C2—C1—H1A	105.6	O9—C13—C12	119.14 (19)
C15—C1—H1A	105.6	O9—C14—C15	103.60 (17)
C6—C1—H1A	105.6	O9—C14—C16	113.43 (18)
C3—C2—C18	120.8 (2)	C15—C14—C16	115.04 (18)
C3—C2—C1	121.8 (2)	O9—C14—H14A	108.2
C18—C2—C1	117.3 (2)	C15—C14—H14A	108.2
C2—C3—C4	121.4 (2)	C16—C14—H14A	108.2
C2—C3—H3A	119.3	C14—C15—C1	109.45 (18)
C4—C3—H3A	119.3	C14—C15—H15A	109.8
O1—C4—C3	123.1 (2)	C1—C15—H15A	109.8
O1—C4—C5	120.3 (2)	C14—C15—H15B	109.8
C3—C4—C5	116.6 (2)	C1—C15—H15B	109.8
O2—C5—C4	110.43 (18)	H15A—C15—H15B	108.2
O2—C5—C6	111.59 (18)	C14—C16—C17	109.82 (18)
C4—C5—C6	110.77 (18)	C14—C16—C11	108.34 (18)
O2—C5—H5A	108.0	C17—C16—C11	107.41 (17)
C4—C5—H5A	108.0	C14—C16—C7	116.32 (17)
C6—C5—H5A	108.0	C17—C16—C7	102.56 (17)
C5—C6—C19	108.61 (18)	C11—C16—C7	111.96 (17)
C5—C6—C1	105.59 (16)	O4—C17—C16	105.42 (17)
C19—C6—C1	111.42 (18)	O4—C17—H17A	110.7
C5—C6—C7	109.69 (17)	C16—C17—H17A	110.7
C19—C6—C7	114.94 (18)	O4—C17—H17B	110.7
C1—C6—C7	106.17 (17)	C16—C17—H17B	110.7
C8—C7—C16	96.96 (16)	H17A—C17—H17B	108.8
C8—C7—C6	119.59 (18)	C2—C18—H18A	109.5
C16—C7—C6	115.84 (17)	C2—C18—H18B	109.5
C8—C7—H7A	107.9	H18A—C18—H18B	109.5
C16—C7—H7A	107.9	C2—C18—H18C	109.5
C6—C7—H7A	107.9	H18A—C18—H18C	109.5
O3—C8—O4	106.79 (17)	H18B—C18—H18C	109.5
O3—C8—C9	108.20 (17)	C6—C19—H19A	109.5
O4—C8—C9	107.87 (17)	C6—C19—H19B	109.5
O3—C8—C7	118.47 (17)	H19A—C19—H19B	109.5
O4—C8—C7	105.57 (17)	C6—C19—H19C	109.5
C9—C8—C7	109.47 (18)	H19A—C19—H19C	109.5
O5—C9—C10	110.95 (19)	H19B—C19—H19C	109.5
O5—C9—C8	106.27 (17)	C10—C20—H20A	120.0
C10—C9—C8	112.45 (17)	C10—C20—H20B	120.0
O5—C9—H9A	109.0	H20A—C20—H20B	120.0
C10—C9—H9A	109.0	C21—O10—H10	109.5
C8—C9—H9A	109.0	O10—C21—H21A	109.5
C20—C10—C9	120.0 (2)	O10—C21—H21B	109.5
C20—C10—C11	122.6 (2)	H21A—C21—H21B	109.5
C9—C10—C11	117.39 (18)	O10—C21—H21C	109.5
O6—C11—C10	113.25 (17)	H21A—C21—H21C	109.5
O6—C11—C12	103.16 (17)	H21B—C21—H21C	109.5
C10—C11—C12	111.51 (18)	H1W1—O1W—H2W1	105.9
O6—C11—C16	108.23 (17)	H1W2—O2W—H2W2	108.4
C15—C1—C2—C3	148.4 (2)	C20—C10—C11—O6	27.0 (3)
C6—C1—C2—C3	19.9 (3)	C9—C10—C11—O6	−155.1 (2)
C15—C1—C2—C18	−35.2 (3)	C20—C10—C11—C12	−88.9 (3)
C6—C1—C2—C18	−163.7 (2)	C9—C10—C11—C12	89.0 (2)
C18—C2—C3—C4	−176.8 (2)	C20—C10—C11—C16	148.1 (2)
C1—C2—C3—C4	−0.5 (4)	C9—C10—C11—C16	−34.0 (3)
C2—C3—C4—O1	−168.7 (2)	O6—C11—C12—O7	−59.4 (2)
C2—C3—C4—C5	13.3 (3)	C10—C11—C12—O7	62.5 (2)
O1—C4—C5—O2	13.0 (3)	C16—C11—C12—O7	−174.96 (17)
C3—C4—C5—O2	−168.9 (2)	O6—C11—C12—C13	60.3 (2)
O1—C4—C5—C6	137.2 (2)	C10—C11—C12—C13	−177.82 (18)
C3—C4—C5—C6	−44.8 (3)	C16—C11—C12—C13	−55.3 (2)
O2—C5—C6—C19	63.6 (2)	C14—O9—C13—O8	166.4 (2)
C4—C5—C6—C19	−59.9 (2)	C14—O9—C13—C12	−16.6 (3)
O2—C5—C6—C1	−176.83 (19)	O7—C12—C13—O8	−27.5 (3)
C4—C5—C6—C1	59.7 (2)	C11—C12—C13—O8	−150.6 (2)
O2—C5—C6—C7	−62.8 (2)	O7—C12—C13—O9	155.59 (19)
C4—C5—C6—C7	173.71 (18)	C11—C12—C13—O9	32.5 (3)
C2—C1—C6—C5	−48.1 (2)	C13—O9—C14—C15	147.4 (2)
C15—C1—C6—C5	−178.84 (18)	C13—O9—C14—C16	22.0 (3)
C2—C1—C6—C19	69.6 (2)	O9—C14—C15—C1	−73.9 (2)
C15—C1—C6—C19	−61.1 (2)	C16—C14—C15—C1	50.4 (3)
C2—C1—C6—C7	−164.58 (18)	C2—C1—C15—C14	161.25 (19)
C15—C1—C6—C7	64.7 (2)	C6—C1—C15—C14	−67.7 (2)
C5—C6—C7—C8	83.5 (2)	O9—C14—C16—C17	−159.36 (18)
C19—C6—C7—C8	−39.2 (3)	C15—C14—C16—C17	81.6 (2)
C1—C6—C7—C8	−162.86 (18)	O9—C14—C16—C11	−42.3 (2)
C5—C6—C7—C16	−161.04 (18)	C15—C14—C16—C11	−161.36 (18)
C19—C6—C7—C16	76.2 (2)	O9—C14—C16—C7	84.8 (2)
C1—C6—C7—C16	−47.4 (2)	C15—C14—C16—C7	−34.2 (3)
C17—O4—C8—O3	154.14 (17)	O6—C11—C16—C14	−51.0 (2)
C17—O4—C8—C9	−89.8 (2)	C10—C11—C16—C14	−175.06 (18)
C17—O4—C8—C7	27.2 (2)	C12—C11—C16—C14	61.4 (2)
C16—C7—C8—O3	−161.90 (19)	O6—C11—C16—C17	67.6 (2)
C6—C7—C8—O3	−36.9 (3)	C10—C11—C16—C17	−56.5 (2)
C16—C7—C8—O4	−42.4 (2)	C12—C11—C16—C17	179.97 (17)
C6—C7—C8—O4	82.6 (2)	O6—C11—C16—C7	179.46 (17)
C16—C7—C8—C9	73.4 (2)	C10—C11—C16—C7	55.4 (2)
C6—C7—C8—C9	−161.50 (18)	C12—C11—C16—C7	−68.2 (2)
O3—C8—C9—O5	−67.8 (2)	C8—C7—C16—C14	161.50 (19)
O4—C8—C9—O5	176.98 (16)	C6—C7—C16—C14	33.8 (3)
C7—C8—C9—O5	62.6 (2)	C8—C7—C16—C17	41.6 (2)
O3—C8—C9—C10	170.59 (18)	C6—C7—C16—C17	−86.1 (2)
O4—C8—C9—C10	55.4 (2)	C8—C7—C16—C11	−73.2 (2)
C7—C8—C9—C10	−59.0 (2)	C6—C7—C16—C11	159.07 (18)
O5—C9—C10—C20	95.7 (3)	C8—O4—C17—C16	1.0 (2)
C8—C9—C10—C20	−145.4 (2)	C14—C16—C17—O4	−152.40 (18)
O5—C9—C10—C11	−82.2 (2)	C11—C16—C17—O4	89.98 (19)
C8—C9—C10—C11	36.6 (3)	C7—C16—C17—O4	−28.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4i	0.88	1.94	2.810 (2)	169
O2—H2···O2Wii	0.82	1.85	2.656 (3)	169
O1W—H2W1···O3iii	0.84	2.06	2.873 (3)	163
O3—H3···O2	0.82	1.71	2.525 (2)	171
O2W—H1W2···O8	0.95	2.03	2.950 (3)	164
O2W—H2W2···O10	0.85	1.91	2.760 (3)	179
O5—H5···O3iv	0.82	1.99	2.805 (2)	172
O6—H6···O9v	0.82	2.14	2.848 (2)	144
O7—H7···O1Wvi	0.82	1.84	2.653 (3)	171
O10—H10···O7vii	0.82	2.29	3.011 (3)	147
O10—H10···O8vii	0.82	2.23	2.911 (3)	140
C1—H1A···O9	0.98	2.48	2.936 (3)	108
C1—H1A···O1iii	0.98	2.56	3.507 (3)	162
C7—H7A···O5	0.98	2.38	2.856 (3)	109
C12—H12A···O1iii	0.98	2.47	3.168 (3)	128
C17—H17A···O10v	0.97	2.60	3.428 (3)	144
C17—H17B···O6	0.97	2.50	2.929 (3)	107
C19—H19B···O2	0.96	2.56	2.957 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4i	0.88	1.94	2.810 (2)	169
O2—H2⋯O2Wii	0.82	1.85	2.656 (3)	169
O1W—H2W1⋯O3iii	0.84	2.06	2.873 (3)	163
O3—H3⋯O2	0.82	1.71	2.525 (2)	171
O2W—H1W2⋯O8	0.95	2.03	2.950 (3)	164
O2W—H2W2⋯O10	0.85	1.91	2.760 (3)	179
O5—H5⋯O3iv	0.82	1.99	2.805 (2)	172
O6—H6⋯O9v	0.82	2.14	2.848 (2)	144
O7—H7⋯O1Wvi	0.82	1.84	2.653 (3)	171
O10—H10⋯O7vii	0.82	2.29	3.011 (3)	147
O10—H10⋯O8vii	0.82	2.23	2.911 (3)	140
C1—H1A⋯O9	0.98	2.48	2.936 (3)	108
C1—H1A⋯O1iii	0.98	2.56	3.507 (3)	162
C7—H7A⋯O5	0.98	2.38	2.856 (3)	109
C12—H12A⋯O1iii	0.98	2.47	3.168 (3)	128
C17—H17A⋯O10v	0.97	2.60	3.428 (3)	144
C17—H17B⋯O6	0.97	2.50	2.929 (3)	107
C19—H19B⋯O2	0.96	2.56	2.957 (3)	105

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .