6β,15β-Diacet-oxy-1β,7β,13α-trihydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

The title compound, C(24)H(34)O(8), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans junctions. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds. In addition, an intra-molecular O-H⋯O hydrogen bond occurs.

Related literature

For the genus Isodon and diterpenoids, see: Sun et al. (2001 ▶); Jung et al. (1990 ▶); Li & Tian (2001 ▶); Yan et al. (2008 ▶); Han et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶)

Experimental

Crystal data

C24H34O8

M = 450.51

Orthorhombic,

a = 10.295 (2) Å

b = 13.696 (3) Å

c = 15.802 (3) Å

V = 2228.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 93 K

0.33 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer

18422 measured reflections

2878 independent reflections

2819 reflections with I > 2σ(I)

R int = 0.034

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.07

2878 reflections

306 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001170/lx2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001170/lx2122Isup2.hkl

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

C24H34O8	F(000) = 968
Mr = 450.51	Dx = 1.343 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8346 reflections
a = 10.295 (2) Å	θ = 3.2–27.5°
b = 13.696 (3) Å	µ = 0.10 mm−1
c = 15.802 (3) Å	T = 93 K
V = 2228.1 (8) Å3	Block, colorless
Z = 4	0.33 × 0.33 × 0.30 mm

Rigaku SPIDER diffractometer	2819 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 27.5°, θmin = 3.2°
ω scans	h = −13→11
18422 measured reflections	k = −17→17
2878 independent reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.1265P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2878 reflections	Δρmax = 0.21 e Å−3
306 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (13)

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 > 2σ(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	0.01173 (10)	0.68667 (8)	0.26057 (7)	0.0149 (2)
O2	0.30874 (12)	0.88041 (9)	0.42632 (7)	0.0212 (3)
H2O	0.315 (2)	0.922 (2)	0.4660 (19)	0.058 (8)*
O3	0.33002 (10)	0.57116 (8)	0.24245 (7)	0.0148 (2)
O4	0.21962 (12)	0.43421 (9)	0.20969 (8)	0.0253 (3)
O5	0.10209 (11)	0.61497 (8)	0.14532 (7)	0.0159 (2)
H5O	0.099 (2)	0.554 (2)	0.1618 (16)	0.050 (7)*
O6	0.13739 (12)	0.96328 (8)	0.03305 (7)	0.0189 (3)
H6O	0.105 (2)	0.923 (2)	−0.0103 (16)	0.055 (8)*
O7	0.43032 (11)	0.75344 (8)	0.18270 (7)	0.0161 (2)
O8	0.51871 (12)	0.65725 (10)	0.08362 (8)	0.0253 (3)
C1	0.18434 (16)	0.83486 (12)	0.43078 (10)	0.0161 (3)
H1	0.1156	0.8864	0.4312	0.019*
C2	0.17508 (17)	0.77546 (13)	0.51205 (10)	0.0188 (4)
H2A	0.1894	0.8187	0.5613	0.023*
H2B	0.0870	0.7470	0.5170	0.023*
C3	0.27532 (17)	0.69440 (12)	0.51243 (10)	0.0193 (4)
H3A	0.2716	0.6601	0.5675	0.023*
H3B	0.3629	0.7235	0.5068	0.023*
C4	0.25500 (16)	0.62004 (12)	0.44115 (10)	0.0171 (3)
C5	0.25206 (15)	0.67689 (11)	0.35551 (9)	0.0135 (3)
H5	0.3437	0.6976	0.3445	0.016*
C6	0.21348 (15)	0.61224 (11)	0.28031 (9)	0.0134 (3)
H6	0.1594	0.5571	0.3023	0.016*
C7	0.13183 (15)	0.66985 (11)	0.21737 (9)	0.0127 (3)
C8	0.18916 (15)	0.76762 (11)	0.19036 (9)	0.0124 (3)
C9	0.21621 (16)	0.82954 (11)	0.27169 (10)	0.0144 (3)
H9	0.3127	0.8358	0.2769	0.017*
C10	0.16867 (15)	0.77195 (11)	0.35071 (9)	0.0140 (3)
C11	0.16190 (17)	0.93342 (12)	0.26232 (10)	0.0190 (4)
H11A	0.0659	0.9314	0.2661	0.023*
H11B	0.1945	0.9746	0.3092	0.023*
C12	0.20189 (18)	0.97887 (11)	0.17758 (10)	0.0181 (3)
H12A	0.2941	0.9992	0.1807	0.022*
H12B	0.1489	1.0380	0.1673	0.022*
C13	0.18435 (16)	0.90739 (11)	0.10258 (10)	0.0148 (3)
C14	0.09702 (16)	0.82277 (11)	0.12983 (10)	0.0148 (3)
H14A	0.0712	0.7817	0.0811	0.018*
H14B	0.0182	0.8462	0.1595	0.018*
C15	0.31094 (15)	0.76055 (11)	0.13340 (9)	0.0140 (3)
H15	0.3032	0.7026	0.0952	0.017*
C16	0.30844 (16)	0.85321 (11)	0.08147 (10)	0.0153 (3)
C17	0.39369 (18)	0.87883 (13)	0.02315 (11)	0.0245 (4)
H17A	0.4650	0.8372	0.0106	0.029*
H17B	0.3838	0.9389	−0.0063	0.029*
C18	0.37174 (18)	0.55017 (14)	0.43998 (11)	0.0238 (4)
H18A	0.4503	0.5864	0.4245	0.029*
H18B	0.3563	0.4983	0.3985	0.029*
H18C	0.3830	0.5213	0.4962	0.029*
C19	0.13432 (17)	0.55891 (13)	0.45997 (10)	0.0225 (4)
H19A	0.1462	0.5241	0.5136	0.027*
H19B	0.1209	0.5116	0.4143	0.027*
H19C	0.0584	0.6018	0.4642	0.027*
C20	0.02593 (15)	0.74576 (12)	0.33582 (9)	0.0159 (3)
H20A	−0.0079	0.7095	0.3853	0.019*
H20B	−0.0256	0.8063	0.3296	0.019*
C21	0.32071 (17)	0.47860 (12)	0.21399 (10)	0.0176 (3)
C22	0.45078 (17)	0.43876 (13)	0.19149 (12)	0.0228 (4)
H22A	0.4994	0.4244	0.2433	0.027*
H22B	0.4985	0.4870	0.1578	0.027*
H22C	0.4401	0.3787	0.1586	0.027*
C23	0.52622 (16)	0.69893 (12)	0.15079 (11)	0.0195 (3)
C24	0.64137 (18)	0.69693 (15)	0.20862 (13)	0.0302 (4)
H24A	0.7075	0.6530	0.1854	0.036*
H24B	0.6145	0.6736	0.2646	0.036*
H24C	0.6775	0.7629	0.2137	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0130 (5)	0.0174 (5)	0.0142 (5)	−0.0016 (4)	0.0013 (4)	−0.0031 (4)
O2	0.0245 (7)	0.0228 (6)	0.0164 (6)	−0.0091 (5)	0.0037 (5)	−0.0077 (5)
O3	0.0171 (6)	0.0124 (5)	0.0148 (5)	0.0013 (4)	0.0024 (4)	−0.0021 (4)
O4	0.0259 (7)	0.0175 (6)	0.0323 (7)	−0.0004 (5)	−0.0010 (6)	−0.0081 (5)
O5	0.0234 (6)	0.0126 (5)	0.0117 (5)	−0.0015 (5)	−0.0025 (5)	−0.0025 (4)
O6	0.0235 (6)	0.0154 (6)	0.0178 (5)	−0.0023 (5)	−0.0055 (5)	0.0056 (5)
O7	0.0139 (6)	0.0172 (5)	0.0174 (5)	0.0017 (5)	−0.0008 (4)	−0.0015 (5)
O8	0.0275 (7)	0.0266 (7)	0.0218 (6)	0.0078 (6)	0.0066 (5)	−0.0018 (5)
C1	0.0178 (8)	0.0168 (7)	0.0138 (7)	−0.0032 (6)	0.0028 (6)	−0.0041 (6)
C2	0.0210 (9)	0.0236 (8)	0.0119 (7)	−0.0040 (7)	0.0017 (6)	−0.0034 (6)
C3	0.0213 (9)	0.0248 (9)	0.0117 (7)	−0.0028 (7)	−0.0011 (6)	−0.0005 (6)
C4	0.0202 (9)	0.0191 (8)	0.0121 (7)	−0.0011 (7)	−0.0010 (6)	0.0015 (6)
C5	0.0131 (8)	0.0149 (7)	0.0125 (7)	−0.0016 (6)	−0.0011 (6)	0.0003 (6)
C6	0.0147 (8)	0.0132 (7)	0.0124 (7)	0.0004 (6)	0.0020 (6)	−0.0010 (6)
C7	0.0153 (8)	0.0122 (7)	0.0107 (6)	−0.0013 (6)	0.0001 (6)	−0.0025 (6)
C8	0.0137 (8)	0.0124 (7)	0.0111 (6)	−0.0001 (6)	−0.0003 (6)	0.0003 (5)
C9	0.0167 (8)	0.0131 (7)	0.0133 (7)	−0.0008 (6)	0.0018 (6)	−0.0020 (6)
C10	0.0169 (8)	0.0131 (7)	0.0120 (7)	−0.0008 (6)	0.0019 (6)	−0.0023 (6)
C11	0.0269 (9)	0.0129 (7)	0.0172 (7)	0.0015 (7)	0.0025 (7)	−0.0020 (6)
C12	0.0239 (9)	0.0123 (7)	0.0182 (7)	0.0001 (7)	0.0004 (7)	−0.0006 (6)
C13	0.0173 (8)	0.0133 (7)	0.0137 (7)	−0.0001 (6)	−0.0022 (6)	0.0018 (6)
C14	0.0151 (8)	0.0137 (7)	0.0156 (7)	0.0007 (6)	−0.0009 (6)	0.0013 (6)
C15	0.0149 (8)	0.0140 (7)	0.0130 (7)	−0.0007 (6)	−0.0005 (6)	−0.0013 (6)
C16	0.0174 (8)	0.0130 (7)	0.0153 (7)	−0.0014 (6)	−0.0006 (6)	−0.0001 (6)
C17	0.0265 (10)	0.0186 (8)	0.0283 (9)	0.0022 (7)	0.0086 (8)	0.0072 (7)
C18	0.0291 (10)	0.0249 (9)	0.0172 (8)	0.0059 (8)	−0.0038 (7)	0.0020 (7)
C19	0.0296 (10)	0.0230 (8)	0.0148 (8)	−0.0056 (8)	0.0014 (7)	0.0032 (7)
C20	0.0174 (8)	0.0174 (7)	0.0129 (7)	−0.0001 (7)	0.0004 (6)	−0.0028 (6)
C21	0.0258 (9)	0.0134 (7)	0.0135 (7)	0.0038 (7)	−0.0019 (7)	0.0001 (6)
C22	0.0262 (10)	0.0188 (8)	0.0233 (8)	0.0048 (7)	0.0012 (7)	−0.0017 (7)
C23	0.0183 (8)	0.0154 (8)	0.0249 (8)	0.0012 (7)	0.0066 (7)	0.0031 (6)
C24	0.0222 (10)	0.0273 (10)	0.0410 (11)	0.0065 (8)	−0.0040 (8)	−0.0005 (8)

O1—C7	1.431 (2)	C9—C11	1.536 (2)
O1—C20	1.446 (2)	C9—C10	1.556 (2)
O2—C1	1.426 (2)	C9—H9	1.0000
O2—H2O	0.85 (3)	C10—C20	1.531 (2)
O3—C21	1.349 (2)	C11—C12	1.533 (2)
O3—C6	1.454 (2)	C11—H11A	0.9900
O4—C21	1.207 (2)	C11—H11B	0.9900
O5—C7	1.398 (2)	C12—C13	1.548 (2)
O5—H5O	0.88 (3)	C12—H12A	0.9900
O6—C13	1.424 (2)	C12—H12B	0.9900
O6—H6O	0.94 (3)	C13—C16	1.515 (2)
O7—C23	1.337 (2)	C13—C14	1.529 (2)
O7—C15	1.458 (2)	C14—H14A	0.9900
O8—C23	1.208 (2)	C14—H14B	0.9900
C1—C2	1.523 (2)	C15—C16	1.511 (2)
C1—C10	1.539 (2)	C15—H15	1.0000
C1—H1	1.0000	C16—C17	1.320 (2)
C2—C3	1.516 (2)	C17—H17A	0.9500
C2—H2A	0.9900	C17—H17B	0.9500
C2—H2B	0.9900	C18—H18A	0.9800
C3—C4	1.533 (2)	C18—H18B	0.9800
C3—H3A	0.9900	C18—H18C	0.9800
C3—H3B	0.9900	C19—H19A	0.9800
C4—C19	1.527 (2)	C19—H19B	0.9800
C4—C18	1.536 (2)	C19—H19C	0.9800
C4—C5	1.562 (2)	C20—H20A	0.9900
C5—C6	1.534 (2)	C20—H20B	0.9900
C5—C10	1.561 (2)	C21—C22	1.489 (2)
C5—H5	1.0000	C22—H22A	0.9800
C6—C7	1.523 (2)	C22—H22B	0.9800
C6—H6	1.0000	C22—H22C	0.9800
C7—C8	1.524 (2)	C23—C24	1.497 (3)
C8—C14	1.544 (2)	C24—H24A	0.9800
C8—C15	1.546 (2)	C24—H24B	0.9800
C8—C9	1.565 (2)	C24—H24C	0.9800
C7—O1—C20	113.28 (11)	C12—C11—H11B	109.4
C1—O2—H2O	108.9 (18)	C9—C11—H11B	109.4
C21—O3—C6	116.25 (13)	H11A—C11—H11B	108.0
C7—O5—H5O	106.4 (16)	C11—C12—C13	112.37 (13)
C13—O6—H6O	111.6 (16)	C11—C12—H12A	109.1
C23—O7—C15	117.28 (12)	C13—C12—H12A	109.1
O2—C1—C2	109.35 (14)	C11—C12—H12B	109.1
O2—C1—C10	107.36 (12)	C13—C12—H12B	109.1
C2—C1—C10	112.80 (13)	H12A—C12—H12B	107.9
O2—C1—H1	109.1	O6—C13—C16	112.32 (13)
C2—C1—H1	109.1	O6—C13—C14	115.17 (13)
C10—C1—H1	109.1	C16—C13—C14	100.76 (12)
C3—C2—C1	110.61 (13)	O6—C13—C12	106.89 (12)
C3—C2—H2A	109.5	C16—C13—C12	112.34 (13)
C1—C2—H2A	109.5	C14—C13—C12	109.42 (13)
C3—C2—H2B	109.5	C13—C14—C8	100.61 (12)
C1—C2—H2B	109.5	C13—C14—H14A	111.7
H2A—C2—H2B	108.1	C8—C14—H14A	111.7
C2—C3—C4	113.00 (13)	C13—C14—H14B	111.7
C2—C3—H3A	109.0	C8—C14—H14B	111.7
C4—C3—H3A	109.0	H14A—C14—H14B	109.4
C2—C3—H3B	109.0	O7—C15—C16	111.13 (12)
C4—C3—H3B	109.0	O7—C15—C8	112.12 (11)
H3A—C3—H3B	107.8	C16—C15—C8	104.46 (12)
C19—C4—C3	109.39 (14)	O7—C15—H15	109.7
C19—C4—C18	107.29 (14)	C16—C15—H15	109.7
C3—C4—C18	108.41 (14)	C8—C15—H15	109.7
C19—C4—C5	115.24 (13)	C17—C16—C15	126.22 (15)
C3—C4—C5	107.95 (13)	C17—C16—C13	125.76 (15)
C18—C4—C5	108.38 (13)	C15—C16—C13	107.82 (13)
C6—C5—C4	112.86 (12)	C16—C17—H17A	120.0
C6—C5—C10	107.54 (12)	C16—C17—H17B	120.0
C4—C5—C10	117.94 (13)	H17A—C17—H17B	120.0
C6—C5—H5	105.9	C4—C18—H18A	109.5
C4—C5—H5	105.9	C4—C18—H18B	109.5
C10—C5—H5	105.9	H18A—C18—H18B	109.5
O3—C6—C7	112.79 (12)	C4—C18—H18C	109.5
O3—C6—C5	109.17 (12)	H18A—C18—H18C	109.5
C7—C6—C5	110.47 (12)	H18B—C18—H18C	109.5
O3—C6—H6	108.1	C4—C19—H19A	109.5
C7—C6—H6	108.1	C4—C19—H19B	109.5
C5—C6—H6	108.1	H19A—C19—H19B	109.5
O5—C7—O1	106.61 (12)	C4—C19—H19C	109.5
O5—C7—C6	111.98 (13)	H19A—C19—H19C	109.5
O1—C7—C6	104.41 (12)	H19B—C19—H19C	109.5
O5—C7—C8	109.21 (12)	O1—C20—C10	110.77 (12)
O1—C7—C8	109.07 (12)	O1—C20—H20A	109.5
C6—C7—C8	115.11 (13)	C10—C20—H20A	109.5
C7—C8—C14	111.42 (13)	O1—C20—H20B	109.5
C7—C8—C15	114.96 (12)	C10—C20—H20B	109.5
C14—C8—C15	99.67 (11)	H20A—C20—H20B	108.1
C7—C8—C9	108.37 (12)	O4—C21—O3	123.60 (15)
C14—C8—C9	110.66 (12)	O4—C21—C22	125.26 (15)
C15—C8—C9	111.57 (12)	O3—C21—C22	111.11 (14)
C11—C9—C10	115.62 (13)	C21—C22—H22A	109.5
C11—C9—C8	110.98 (13)	C21—C22—H22B	109.5
C10—C9—C8	109.17 (12)	H22A—C22—H22B	109.5
C11—C9—H9	106.9	C21—C22—H22C	109.5
C10—C9—H9	106.9	H22A—C22—H22C	109.5
C8—C9—H9	106.9	H22B—C22—H22C	109.5
C20—C10—C1	110.99 (12)	O8—C23—O7	123.25 (16)
C20—C10—C9	107.30 (13)	O8—C23—C24	125.35 (16)
C1—C10—C9	110.06 (12)	O7—C23—C24	111.40 (15)
C20—C10—C5	109.87 (12)	C23—C24—H24A	109.5
C1—C10—C5	111.67 (13)	C23—C24—H24B	109.5
C9—C10—C5	106.78 (12)	H24A—C24—H24B	109.5
C12—C11—C9	111.26 (13)	C23—C24—H24C	109.5
C12—C11—H11A	109.4	H24A—C24—H24C	109.5
C9—C11—H11A	109.4	H24B—C24—H24C	109.5
O2—C1—C2—C3	−62.53 (16)	C8—C9—C10—C20	−54.65 (15)
C10—C1—C2—C3	56.86 (18)	C11—C9—C10—C1	−49.55 (18)
C1—C2—C3—C4	−62.82 (18)	C8—C9—C10—C1	−175.51 (13)
C2—C3—C4—C19	−71.09 (17)	C11—C9—C10—C5	−170.93 (13)
C2—C3—C4—C18	172.21 (14)	C8—C9—C10—C5	63.11 (15)
C2—C3—C4—C5	55.00 (18)	C6—C5—C10—C20	47.55 (15)
C19—C4—C5—C6	−49.47 (19)	C4—C5—C10—C20	−81.40 (16)
C3—C4—C5—C6	−172.06 (13)	C6—C5—C10—C1	171.15 (12)
C18—C4—C5—C6	70.72 (17)	C4—C5—C10—C1	42.20 (18)
C19—C4—C5—C10	76.95 (18)	C6—C5—C10—C9	−68.50 (15)
C3—C4—C5—C10	−45.64 (18)	C4—C5—C10—C9	162.55 (13)
C18—C4—C5—C10	−162.86 (14)	C10—C9—C11—C12	−173.29 (14)
C21—O3—C6—C7	−94.07 (15)	C8—C9—C11—C12	−48.25 (18)
C21—O3—C6—C5	142.72 (13)	C9—C11—C12—C13	45.16 (19)
C4—C5—C6—O3	−91.32 (15)	C11—C12—C13—O6	141.31 (14)
C10—C5—C6—O3	136.89 (12)	C11—C12—C13—C16	−95.05 (16)
C4—C5—C6—C7	144.10 (13)	C11—C12—C13—C14	15.98 (19)
C10—C5—C6—C7	12.31 (16)	O6—C13—C14—C8	168.34 (12)
C20—O1—C7—O5	−178.14 (11)	C16—C13—C14—C8	47.24 (14)
C20—O1—C7—C6	63.19 (15)	C12—C13—C14—C8	−71.27 (15)
C20—O1—C7—C8	−60.34 (15)	C7—C8—C14—C13	−171.67 (12)
O3—C6—C7—O5	53.61 (16)	C15—C8—C14—C13	−49.89 (13)
C5—C6—C7—O5	176.09 (12)	C9—C8—C14—C13	67.68 (15)
O3—C6—C7—O1	168.56 (11)	C23—O7—C15—C16	−97.73 (16)
C5—C6—C7—O1	−68.96 (15)	C23—O7—C15—C8	145.78 (13)
O3—C6—C7—C8	−71.91 (16)	C7—C8—C15—O7	−87.21 (15)
C5—C6—C7—C8	50.57 (17)	C14—C8—C15—O7	153.57 (12)
O5—C7—C8—C14	55.65 (16)	C9—C8—C15—O7	36.68 (16)
O1—C7—C8—C14	−60.50 (15)	C7—C8—C15—C16	152.35 (13)
C6—C7—C8—C14	−177.42 (12)	C14—C8—C15—C16	33.14 (14)
O5—C7—C8—C15	−56.79 (17)	C9—C8—C15—C16	−83.76 (14)
O1—C7—C8—C15	−172.94 (11)	O7—C15—C16—C17	59.4 (2)
C6—C7—C8—C15	70.14 (17)	C8—C15—C16—C17	−179.46 (16)
O5—C7—C8—C9	177.63 (12)	O7—C15—C16—C13	−125.49 (13)
O1—C7—C8—C9	61.48 (15)	C8—C15—C16—C13	−4.39 (15)
C6—C7—C8—C9	−55.43 (16)	O6—C13—C16—C17	25.4 (2)
C7—C8—C9—C11	−131.48 (14)	C14—C13—C16—C17	148.54 (17)
C14—C8—C9—C11	−9.03 (17)	C12—C13—C16—C17	−95.1 (2)
C15—C8—C9—C11	100.98 (15)	O6—C13—C16—C15	−149.65 (13)
C7—C8—C9—C10	−2.89 (17)	C14—C13—C16—C15	−26.56 (15)
C14—C8—C9—C10	119.55 (14)	C12—C13—C16—C15	89.81 (15)
C15—C8—C9—C10	−130.43 (13)	C7—O1—C20—C10	−1.88 (17)
O2—C1—C10—C20	−162.52 (13)	C1—C10—C20—O1	−179.99 (12)
C2—C1—C10—C20	76.95 (17)	C9—C10—C20—O1	59.73 (16)
O2—C1—C10—C9	−43.89 (17)	C5—C10—C20—O1	−56.00 (16)
C2—C1—C10—C9	−164.43 (14)	C6—O3—C21—O4	8.8 (2)
O2—C1—C10—C5	74.52 (15)	C6—O3—C21—C22	−169.57 (13)
C2—C1—C10—C5	−46.02 (18)	C15—O7—C23—O8	1.0 (2)
C11—C9—C10—C20	71.31 (16)	C15—O7—C23—C24	−179.03 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O6i	0.85 (3)	1.96 (3)	2.7811 (17)	163 (3)
O5—H5O···O4	0.88 (3)	2.19 (3)	2.9373 (18)	142 (2)
O6—H6O···O8ii	0.94 (3)	1.83 (3)	2.7600 (17)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O6i	0.85 (3)	1.96 (3)	2.7811 (17)	163 (3)
O5—H5O⋯O4	0.88 (3)	2.19 (3)	2.9373 (18)	142 (2)
O6—H6O⋯O8ii	0.94 (3)	1.83 (3)	2.7600 (17)	170 (2)

Symmetry codes: (i) ; (ii) .