6β-Acet-oxy-1α,7β,11β,15β-tetra-hydr-oxy-7α,20-ep-oxy-ent-kaur-16-ene.

The title compound, C(22)H(32)O(7), a natural ent-kaurane diterpenoid also referred to as Maoyecrystal F, was obtained from the medicinal plant Isodon nervosa. There are four rings with the expected cis and trans junctions. Cyclohexane ring A adopts a chair conformation, rings B and C adopt boat conformations, while the five-membered ring has an envelope conformation. The mol-ecules stack along the a axis in the crystal and are linked together by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For related literature on the genus Isodon and diterpenoids, see: Sun et al. (2001 ▶); Zhang et al. (2003 ▶); Yan et al. (2008 ▶).

Experimental

Crystal data

C22H32O7

M = 408.21

Monoclinic,

a = 9.759 (3) Å

b = 6.6712 (17) Å

c = 14.927 (4) Å

β = 90.002 (4)°

V = 971.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 93 K

0.50 × 0.33 × 0.23 mm

Data collection

Rigaku AFC10 Saturn724+ diffractometer

7880 measured reflections

2412 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.00

2412 reflections

281 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536810000231/hg2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000231/hg2621Isup2.hkl

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

C22H32O7	F(000) = 440
Mr = 408.21	Dx = 1.396 Mg m−3
Monoclinic, P21	Melting point = 489–491 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.759 (3) Å	Cell parameters from 3508 reflections
b = 6.6712 (17) Å	θ = 3.3–27.5°
c = 14.927 (4) Å	µ = 0.10 mm−1
β = 90.002 (4)°	T = 93 K
V = 971.8 (4) Å3	Prism, colorless
Z = 2	0.50 × 0.33 × 0.23 mm

Rigaku AFC10 Saturn724+ diffractometer	2262 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.025
graphite	θmax = 27.5°, θmin = 3.3°
Detector resolution: 28.5714 pixels mm-1	h = −9→12
ω scans	k = −8→8
7880 measured reflections	l = −19→19
2412 independent reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0336P)2 + 0.163P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.17 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	0.71560 (11)	0.24172 (19)	0.19745 (8)	0.0137 (3)
O2	0.39948 (13)	0.6243 (2)	0.07687 (8)	0.0153 (3)
O3	0.76328 (11)	0.54105 (18)	0.39884 (7)	0.0130 (3)
O4	0.91072 (12)	0.2840 (2)	0.27898 (9)	0.0146 (3)
O5	0.57949 (12)	0.90169 (19)	0.06925 (8)	0.0149 (3)
O6	0.87086 (12)	0.86646 (19)	0.30694 (8)	0.0143 (3)
O7	0.78961 (13)	0.2859 (2)	0.49762 (9)	0.0232 (3)
C1	0.41761 (16)	0.6066 (3)	0.17186 (11)	0.0124 (3)
H1	0.4059	0.7432	0.1983	0.015*
C2	0.30078 (17)	0.4772 (3)	0.20568 (11)	0.0157 (4)
H2A	0.3104	0.3398	0.1814	0.019*
H2B	0.2125	0.5326	0.1843	0.019*
C3	0.30058 (17)	0.4693 (3)	0.30758 (11)	0.0162 (4)
H3A	0.2223	0.3867	0.3280	0.019*
H3B	0.2878	0.6065	0.3314	0.019*
C4	0.43380 (16)	0.3814 (3)	0.34543 (11)	0.0132 (3)
C5	0.55753 (16)	0.4991 (3)	0.30404 (11)	0.0116 (3)
H5	0.5535	0.6368	0.3304	0.014*
C6	0.69539 (16)	0.4098 (3)	0.33418 (10)	0.0119 (3)
H6	0.6780	0.2771	0.3632	0.014*
C7	0.78918 (16)	0.3783 (3)	0.25387 (11)	0.0121 (3)
C8	0.82107 (16)	0.5716 (3)	0.20203 (11)	0.0116 (3)
C9	0.68182 (16)	0.6785 (3)	0.17895 (11)	0.0111 (3)
H9	0.6720	0.7965	0.2198	0.013*
C10	0.56065 (16)	0.5289 (3)	0.19985 (11)	0.0111 (3)
C11	0.68778 (17)	0.7582 (3)	0.08150 (11)	0.0132 (3)
H11	0.6716	0.6433	0.0398	0.016*
C12	0.82467 (17)	0.8558 (3)	0.05703 (11)	0.0166 (4)
H12A	0.8296	0.9898	0.0854	0.020*
H12B	0.8285	0.8750	−0.0087	0.020*
C13	0.95062 (17)	0.7303 (3)	0.08700 (11)	0.0160 (4)
H13	1.0228	0.7243	0.0395	0.019*
C14	0.90325 (17)	0.5203 (3)	0.11600 (11)	0.0143 (3)
H14A	0.9820	0.4315	0.1292	0.017*
H14B	0.8444	0.4569	0.0700	0.017*
C15	0.92640 (16)	0.7137 (3)	0.24989 (11)	0.0132 (3)
H15	0.9913	0.6298	0.2857	0.016*
C16	1.00555 (17)	0.8127 (3)	0.17408 (11)	0.0152 (4)
C17	1.10478 (18)	0.9460 (3)	0.18423 (13)	0.0210 (4)
H17A	1.1495	1.0001	0.1332	0.025*
H17B	1.1313	0.9875	0.2426	0.025*
C18	0.43741 (17)	0.4168 (3)	0.44718 (11)	0.0165 (4)
H18A	0.3619	0.3437	0.4756	0.020*
H18B	0.4278	0.5604	0.4595	0.020*
H18C	0.5248	0.3689	0.4713	0.020*
C19	0.43608 (18)	0.1517 (3)	0.32907 (12)	0.0169 (4)
H19A	0.3618	0.0884	0.3630	0.020*
H19B	0.5243	0.0970	0.3488	0.020*
H19C	0.4236	0.1247	0.2651	0.020*
C20	0.59817 (16)	0.3306 (3)	0.15381 (11)	0.0124 (3)
H20A	0.5194	0.2372	0.1568	0.015*
H20B	0.6194	0.3554	0.0899	0.015*
C21	0.81536 (17)	0.4540 (3)	0.47425 (11)	0.0158 (4)
C22	0.90964 (19)	0.5955 (3)	0.52190 (12)	0.0221 (4)
H22A	0.9963	0.6051	0.4890	0.027*
H22B	0.9273	0.5457	0.5826	0.027*
H22C	0.8670	0.7283	0.5253	0.027*
H5O	0.597 (2)	0.957 (4)	0.0218 (15)	0.022 (6)*
H6O	0.834 (2)	0.812 (4)	0.3491 (15)	0.025 (6)*
H2O	0.444 (2)	0.730 (4)	0.0632 (15)	0.029 (6)*
H4O	0.892 (2)	0.166 (4)	0.2884 (16)	0.031 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0143 (5)	0.0100 (6)	0.0166 (6)	0.0011 (5)	−0.0030 (4)	−0.0022 (5)
O2	0.0183 (6)	0.0157 (7)	0.0119 (6)	−0.0004 (5)	−0.0039 (5)	−0.0004 (5)
O3	0.0139 (5)	0.0136 (6)	0.0116 (5)	−0.0020 (5)	−0.0024 (4)	−0.0010 (5)
O4	0.0116 (5)	0.0100 (7)	0.0223 (6)	0.0012 (5)	−0.0015 (5)	0.0024 (5)
O5	0.0174 (6)	0.0129 (6)	0.0143 (6)	0.0027 (5)	−0.0016 (5)	0.0034 (5)
O6	0.0178 (6)	0.0108 (6)	0.0145 (6)	−0.0008 (5)	0.0011 (5)	−0.0015 (5)
O7	0.0194 (6)	0.0275 (8)	0.0227 (7)	−0.0025 (6)	−0.0052 (5)	0.0115 (6)
C1	0.0137 (8)	0.0126 (8)	0.0109 (7)	0.0022 (7)	−0.0028 (6)	−0.0008 (6)
C2	0.0127 (7)	0.0170 (9)	0.0174 (8)	−0.0002 (7)	−0.0035 (6)	−0.0001 (7)
C3	0.0116 (7)	0.0191 (9)	0.0179 (8)	0.0000 (7)	0.0011 (6)	0.0005 (7)
C4	0.0118 (7)	0.0144 (9)	0.0135 (7)	−0.0011 (7)	−0.0003 (6)	−0.0003 (7)
C5	0.0118 (7)	0.0112 (8)	0.0117 (7)	0.0005 (7)	−0.0011 (6)	−0.0012 (6)
C6	0.0116 (7)	0.0111 (8)	0.0130 (7)	−0.0015 (7)	−0.0026 (6)	0.0002 (7)
C7	0.0122 (7)	0.0090 (8)	0.0150 (7)	0.0012 (7)	−0.0027 (6)	−0.0013 (7)
C8	0.0116 (7)	0.0100 (8)	0.0132 (7)	0.0013 (6)	0.0007 (6)	−0.0001 (7)
C9	0.0122 (7)	0.0095 (8)	0.0115 (7)	0.0013 (6)	−0.0013 (6)	−0.0003 (6)
C10	0.0114 (7)	0.0102 (8)	0.0116 (7)	0.0003 (7)	−0.0011 (6)	0.0001 (6)
C11	0.0160 (7)	0.0117 (8)	0.0119 (7)	0.0033 (7)	0.0000 (6)	−0.0002 (6)
C12	0.0179 (8)	0.0157 (9)	0.0161 (8)	−0.0009 (8)	0.0016 (6)	0.0014 (7)
C13	0.0157 (8)	0.0155 (9)	0.0169 (8)	0.0006 (7)	0.0042 (6)	0.0010 (7)
C14	0.0149 (7)	0.0128 (9)	0.0154 (8)	0.0023 (7)	0.0031 (6)	−0.0019 (7)
C15	0.0127 (7)	0.0112 (9)	0.0158 (8)	0.0018 (7)	−0.0011 (6)	0.0000 (7)
C16	0.0133 (7)	0.0123 (9)	0.0199 (8)	0.0038 (7)	0.0017 (6)	0.0007 (7)
C17	0.0184 (8)	0.0189 (10)	0.0257 (9)	−0.0017 (8)	0.0036 (7)	0.0006 (8)
C18	0.0158 (8)	0.0189 (10)	0.0147 (8)	−0.0005 (7)	0.0017 (6)	0.0006 (7)
C19	0.0167 (8)	0.0156 (9)	0.0186 (8)	−0.0040 (7)	−0.0005 (7)	0.0028 (7)
C20	0.0134 (7)	0.0103 (8)	0.0136 (7)	0.0010 (7)	−0.0014 (6)	−0.0017 (7)
C21	0.0115 (7)	0.0236 (10)	0.0124 (7)	0.0018 (7)	−0.0002 (6)	0.0026 (7)
C22	0.0190 (9)	0.0298 (11)	0.0175 (8)	0.0000 (8)	−0.0049 (7)	−0.0014 (8)

O1—C7	1.434 (2)	C8—C9	1.573 (2)
O1—C20	1.4453 (19)	C9—C11	1.550 (2)
O2—C1	1.4337 (19)	C9—C10	1.578 (2)
O2—H2O	0.85 (3)	C9—H9	1.0000
O3—C21	1.365 (2)	C10—C20	1.535 (2)
O3—C6	1.4620 (19)	C11—C12	1.530 (2)
O4—C7	1.394 (2)	C11—H11	1.0000
O4—H4O	0.82 (3)	C12—C13	1.553 (2)
O5—C11	1.438 (2)	C12—H12A	0.9900
O5—H5O	0.82 (2)	C12—H12B	0.9900
O6—C15	1.434 (2)	C13—C16	1.510 (2)
O6—H6O	0.81 (2)	C13—C14	1.537 (3)
O7—C21	1.201 (2)	C13—H13	1.0000
C1—C2	1.517 (2)	C14—H14A	0.9900
C1—C10	1.546 (2)	C14—H14B	0.9900
C1—H1	1.0000	C15—C16	1.521 (2)
C2—C3	1.522 (2)	C15—H15	1.0000
C2—H2A	0.9900	C16—C17	1.323 (3)
C2—H2B	0.9900	C17—H17A	0.9500
C3—C4	1.534 (2)	C17—H17B	0.9500
C3—H3A	0.9900	C18—H18A	0.9800
C3—H3B	0.9900	C18—H18B	0.9800
C4—C18	1.538 (2)	C18—H18C	0.9800
C4—C19	1.552 (3)	C19—H19A	0.9800
C4—C5	1.567 (2)	C19—H19B	0.9800
C5—C6	1.539 (2)	C19—H19C	0.9800
C5—C10	1.568 (2)	C20—H20A	0.9900
C5—H5	1.0000	C20—H20B	0.9900
C6—C7	1.523 (2)	C21—C22	1.498 (3)
C6—H6	1.0000	C22—H22A	0.9800
C7—C8	1.535 (2)	C22—H22B	0.9800
C8—C14	1.552 (2)	C22—H22C	0.9800
C8—C15	1.570 (2)
C7—O1—C20	113.65 (13)	C5—C10—C9	106.89 (12)
C1—O2—H2O	104.1 (16)	O5—C11—C12	109.13 (14)
C21—O3—C6	117.28 (14)	O5—C11—C9	108.68 (13)
C7—O4—H4O	106.7 (17)	C12—C11—C9	113.75 (13)
C11—O5—H5O	104.9 (16)	O5—C11—H11	108.4
C15—O6—H6O	108.2 (17)	C12—C11—H11	108.4
O2—C1—C2	106.46 (13)	C9—C11—H11	108.4
O2—C1—C10	113.96 (13)	C11—C12—C13	113.12 (14)
C2—C1—C10	113.43 (14)	C11—C12—H12A	109.0
O2—C1—H1	107.6	C13—C12—H12A	109.0
C2—C1—H1	107.6	C11—C12—H12B	109.0
C10—C1—H1	107.6	C13—C12—H12B	109.0
C1—C2—C3	110.70 (14)	H12A—C12—H12B	107.8
C1—C2—H2A	109.5	C16—C13—C14	101.32 (14)
C3—C2—H2A	109.5	C16—C13—C12	109.43 (15)
C1—C2—H2B	109.5	C14—C13—C12	109.54 (14)
C3—C2—H2B	109.5	C16—C13—H13	112.0
H2A—C2—H2B	108.1	C14—C13—H13	112.0
C2—C3—C4	112.34 (14)	C12—C13—H13	112.0
C2—C3—H3A	109.1	C13—C14—C8	100.80 (13)
C4—C3—H3A	109.1	C13—C14—H14A	111.6
C2—C3—H3B	109.1	C8—C14—H14A	111.6
C4—C3—H3B	109.1	C13—C14—H14B	111.6
H3A—C3—H3B	107.9	C8—C14—H14B	111.6
C3—C4—C18	108.92 (14)	H14A—C14—H14B	109.4
C3—C4—C19	109.37 (15)	O6—C15—C16	108.98 (15)
C18—C4—C19	107.88 (15)	O6—C15—C8	116.86 (13)
C3—C4—C5	108.42 (14)	C16—C15—C8	104.85 (13)
C18—C4—C5	107.14 (13)	O6—C15—H15	108.6
C19—C4—C5	114.95 (14)	C16—C15—H15	108.6
C6—C5—C4	111.35 (14)	C8—C15—H15	108.6
C6—C5—C10	108.79 (13)	C17—C16—C13	127.09 (17)
C4—C5—C10	117.99 (13)	C17—C16—C15	125.33 (16)
C6—C5—H5	106.0	C13—C16—C15	107.58 (14)
C4—C5—H5	106.0	C16—C17—H17A	120.0
C10—C5—H5	106.0	C16—C17—H17B	120.0
O3—C6—C7	109.26 (12)	H17A—C17—H17B	120.0
O3—C6—C5	110.92 (14)	C4—C18—H18A	109.5
C7—C6—C5	110.41 (13)	C4—C18—H18B	109.5
O3—C6—H6	108.7	H18A—C18—H18B	109.5
C7—C6—H6	108.7	C4—C18—H18C	109.5
C5—C6—H6	108.7	H18A—C18—H18C	109.5
O4—C7—O1	107.27 (13)	H18B—C18—H18C	109.5
O4—C7—C6	111.22 (13)	C4—C19—H19A	109.5
O1—C7—C6	104.41 (12)	C4—C19—H19B	109.5
O4—C7—C8	110.02 (13)	H19A—C19—H19B	109.5
O1—C7—C8	109.84 (13)	C4—C19—H19C	109.5
C6—C7—C8	113.76 (14)	H19A—C19—H19C	109.5
C7—C8—C14	109.67 (14)	H19B—C19—H19C	109.5
C7—C8—C15	114.24 (13)	O1—C20—C10	109.92 (12)
C14—C8—C15	99.86 (13)	O1—C20—H20A	109.7
C7—C8—C9	108.42 (13)	C10—C20—H20A	109.7
C14—C8—C9	111.41 (13)	O1—C20—H20B	109.7
C15—C8—C9	113.04 (14)	C10—C20—H20B	109.7
C11—C9—C8	109.19 (12)	H20A—C20—H20B	108.2
C11—C9—C10	115.50 (13)	O7—C21—O3	123.98 (17)
C8—C9—C10	108.50 (13)	O7—C21—C22	125.39 (16)
C11—C9—H9	107.8	O3—C21—C22	110.63 (16)
C8—C9—H9	107.8	C21—C22—H22A	109.5
C10—C9—H9	107.8	C21—C22—H22B	109.5
C20—C10—C1	112.54 (13)	H22A—C22—H22B	109.5
C20—C10—C5	109.85 (14)	C21—C22—H22C	109.5
C1—C10—C5	107.03 (12)	H22A—C22—H22C	109.5
C20—C10—C9	106.13 (13)	H22B—C22—H22C	109.5
C1—C10—C9	114.25 (14)
O2—C1—C2—C3	−173.23 (14)	C2—C1—C10—C9	−170.68 (14)
C10—C1—C2—C3	60.63 (19)	C6—C5—C10—C20	54.20 (17)
C1—C2—C3—C4	−60.1 (2)	C4—C5—C10—C20	−73.84 (17)
C2—C3—C4—C18	168.91 (15)	C6—C5—C10—C1	176.66 (14)
C2—C3—C4—C19	−73.40 (19)	C4—C5—C10—C1	48.62 (19)
C2—C3—C4—C5	52.65 (19)	C6—C5—C10—C9	−60.52 (17)
C3—C4—C5—C6	−176.20 (14)	C4—C5—C10—C9	171.44 (14)
C18—C4—C5—C6	66.39 (18)	C11—C9—C10—C20	73.03 (17)
C19—C4—C5—C6	−53.47 (19)	C8—C9—C10—C20	−49.90 (16)
C3—C4—C5—C10	−49.38 (19)	C11—C9—C10—C1	−51.57 (18)
C18—C4—C5—C10	−166.79 (15)	C8—C9—C10—C1	−174.50 (13)
C19—C4—C5—C10	73.35 (19)	C11—C9—C10—C5	−169.77 (14)
C21—O3—C6—C7	−104.90 (15)	C8—C9—C10—C5	67.31 (16)
C21—O3—C6—C5	133.16 (14)	C8—C9—C11—O5	−163.90 (13)
C4—C5—C6—O3	−107.33 (15)	C10—C9—C11—O5	73.54 (17)
C10—C5—C6—O3	120.97 (14)	C8—C9—C11—C12	−42.11 (19)
C4—C5—C6—C7	131.41 (15)	C10—C9—C11—C12	−164.67 (15)
C10—C5—C6—C7	−0.29 (19)	O5—C11—C12—C13	167.63 (13)
C20—O1—C7—O4	−170.16 (13)	C9—C11—C12—C13	46.1 (2)
C20—O1—C7—C6	71.74 (15)	C11—C12—C13—C16	−98.54 (17)
C20—O1—C7—C8	−50.61 (16)	C11—C12—C13—C14	11.7 (2)
O3—C6—C7—O4	62.10 (17)	C16—C13—C14—C8	47.88 (15)
C5—C6—C7—O4	−175.65 (14)	C12—C13—C14—C8	−67.65 (16)
O3—C6—C7—O1	177.48 (13)	C7—C8—C14—C13	−168.02 (13)
C5—C6—C7—O1	−60.27 (17)	C15—C8—C14—C13	−47.72 (15)
O3—C6—C7—C8	−62.79 (17)	C9—C8—C14—C13	71.94 (16)
C5—C6—C7—C8	59.46 (18)	C7—C8—C15—O6	−92.48 (18)
O4—C7—C8—C14	60.79 (17)	C14—C8—C15—O6	150.59 (14)
O1—C7—C8—C14	−57.07 (17)	C9—C8—C15—O6	32.1 (2)
C6—C7—C8—C14	−173.68 (13)	C7—C8—C15—C16	146.76 (14)
O4—C7—C8—C15	−50.34 (18)	C14—C8—C15—C16	29.83 (16)
O1—C7—C8—C15	−168.19 (13)	C9—C8—C15—C16	−88.63 (15)
C6—C7—C8—C15	75.20 (17)	C14—C13—C16—C17	150.63 (18)
O4—C7—C8—C9	−177.37 (13)	C12—C13—C16—C17	−93.8 (2)
O1—C7—C8—C9	64.77 (16)	C14—C13—C16—C15	−29.05 (16)
C6—C7—C8—C9	−51.83 (17)	C12—C13—C16—C15	86.56 (17)
C7—C8—C9—C11	−137.89 (14)	O6—C15—C16—C17	53.7 (2)
C14—C8—C9—C11	−17.12 (19)	C8—C15—C16—C17	179.54 (17)
C15—C8—C9—C11	94.40 (16)	O6—C15—C16—C13	−126.61 (14)
C7—C8—C9—C10	−11.23 (17)	C8—C15—C16—C13	−0.78 (18)
C14—C8—C9—C10	109.54 (15)	C7—O1—C20—C10	−15.94 (18)
C15—C8—C9—C10	−138.94 (14)	C1—C10—C20—O1	−166.48 (13)
O2—C1—C10—C20	−53.85 (19)	C5—C10—C20—O1	−47.35 (17)
C2—C1—C10—C20	68.20 (17)	C9—C10—C20—O1	67.87 (16)
O2—C1—C10—C5	−174.62 (14)	C6—O3—C21—O7	−12.8 (2)
C2—C1—C10—C5	−52.56 (18)	C6—O3—C21—C22	166.23 (14)
O2—C1—C10—C9	67.26 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O5	0.85 (3)	1.75 (3)	2.5539 (19)	156 (2)
O4—H4O···O6i	0.82 (3)	2.03 (3)	2.843 (2)	172 (2)
O5—H5O···O2ii	0.82 (2)	1.85 (2)	2.6467 (18)	165 (2)
O6—H6O···O3	0.81 (2)	2.07 (3)	2.7743 (18)	145 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O5	0.85 (3)	1.75 (3)	2.5539 (19)	156 (2)
O4—H4O⋯O6i	0.82 (3)	2.03 (3)	2.843 (2)	172 (2)
O5—H5O⋯O2ii	0.82 (2)	1.85 (2)	2.6467 (18)	165 (2)
O6—H6O⋯O3	0.81 (2)	2.07 (3)	2.7743 (18)	145 (2)

Symmetry codes: (i) ; (ii) .