An ent-kaurane diterpenoid from Isodon japonica var. glaucocalyx.

The title compound, 14β-acet-oxy-7α-hydr-oxy-ent-kaur-16-ene-3,15-dione or glaucocalyxin B, C(22)H(30)O(5), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans ring junctions. In the crystal structure, there are two mol-ecules in the asymmetric unit related by a noncrystallographic twofold screw axis, and ring A is disordered [ratio occupancies 0.829 (19):0.171 (19)], such that both chair and boat conformations are present, but with the boat conformation as the major component. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For related literature on the genus Isodon and diterpenoids therefrom, see: Liu et al. (1988 ▶); Kim et al. (1992 ▶); Sun et al. (2001 ▶); Bai et al. (2005 ▶). For expected bond-length ranges, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H30O5

M = 374.46

Monoclinic,

a = 8.485 (4) Å

b = 23.786 (10) Å

c = 9.930 (4) Å

β = 91.039 (17)°

V = 2003.8 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.36 × 0.34 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

19620 measured reflections

4669 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.164

S = 1.00

4669 reflections

524 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027159/ez2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027159/ez2171Isup2.hkl

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

C22H30O5	Dx = 1.241 Mg m−3
Mr = 374.46	Melting point: 463 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.485 (4) Å	Cell parameters from 12776 reflections
b = 23.786 (10) Å	θ = 3.1–27.6°
c = 9.930 (4) Å	µ = 0.09 mm−1
β = 91.039 (17)°	T = 296 K
V = 2003.8 (15) Å3	Block, colourless
Z = 4	0.36 × 0.34 × 0.32 mm
F(000) = 808

Rigaku R-AXIS RAPID diffractometer	2856 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.070
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −10→11
19620 measured reflections	k = −30→28
4669 independent reflections	l = −12→12

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0896P)2 + 0.022P] where P = (Fo2 + 2Fc2)/3
4669 reflections	(Δ/σ)max = 0.001
524 parameters	Δρmax = 0.19 e Å−3
14 restraints	Δρmin = −0.20 e Å−3

Experimental. The assignment of absolute structure was based on comparison of the optical rotation with that of related compounds with known stereochemistry.

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	Occ. (<1)
O2	0.1468 (4)	0.62378 (17)	0.4126 (3)	0.0622 (9)
H2O	0.1223	0.6421	0.3455	0.075*
O3	−0.1799 (5)	0.69449 (15)	0.3591 (3)	0.0678 (10)
O4	−0.0788 (4)	0.53978 (13)	0.3705 (3)	0.0528 (8)
O5	0.1013 (6)	0.4948 (2)	0.4969 (5)	0.1003 (17)
O1	0.1366 (10)	0.6324 (4)	1.1368 (5)	0.097 (3)	0.677 (9)
C1	−0.1799 (14)	0.6575 (9)	0.9035 (12)	0.0647 (16)	0.677 (9)
H1A	−0.2358	0.6891	0.8638	0.078*	0.677 (9)
H1B	−0.2575	0.6331	0.9438	0.078*	0.677 (9)
C2	−0.0687 (12)	0.6796 (5)	1.0157 (8)	0.077 (3)	0.677 (9)
H2A	−0.0502	0.7193	0.9995	0.092*	0.677 (9)
H2B	−0.1227	0.6766	1.1007	0.092*	0.677 (9)
O1"	0.1487 (19)	0.6698 (7)	1.1325 (10)	0.097 (3)	0.323 (9)
C1"	−0.173 (3)	0.6548 (19)	0.9108 (18)	0.0647 (16)	0.323 (9)
H1C	−0.1763	0.6949	0.8932	0.078*	0.323 (9)
H1D	−0.2805	0.6418	0.9200	0.078*	0.323 (9)
C2"	−0.082 (3)	0.6443 (12)	1.0439 (18)	0.077 (3)	0.323 (9)
H2C	−0.1191	0.6701	1.1117	0.092*	0.323 (9)
H2D	−0.1030	0.6064	1.0746	0.092*	0.323 (9)
C3	0.0870 (6)	0.6513 (2)	1.0308 (4)	0.0596 (13)
C4	0.1788 (6)	0.6446 (2)	0.9042 (4)	0.0522 (11)
C5	0.0705 (5)	0.64895 (18)	0.7754 (4)	0.0391 (9)
H5	0.0561	0.6893	0.7597	0.047*
C6	0.1477 (5)	0.6264 (2)	0.6482 (4)	0.0444 (10)
H6A	0.2535	0.6416	0.6425	0.053*
H6B	0.1559	0.5858	0.6542	0.053*
C7	0.0559 (5)	0.64180 (19)	0.5227 (4)	0.0442 (10)
H7	0.0513	0.6829	0.5189	0.053*
C8	−0.1146 (5)	0.62046 (18)	0.5220 (4)	0.0380 (9)
C9	−0.1924 (5)	0.63960 (18)	0.6580 (4)	0.0443 (10)
H9	−0.1918	0.6808	0.6543	0.053*
C10	−0.0983 (5)	0.62477 (17)	0.7901 (3)	0.0428 (10)
C11	−0.3706 (6)	0.6233 (2)	0.6593 (5)	0.0604 (13)
H11A	−0.4033	0.6220	0.7523	0.073*
H11B	−0.4300	0.6532	0.6154	0.073*
C12	−0.4176 (6)	0.5680 (3)	0.5925 (5)	0.0669 (14)
H12A	−0.5306	0.5674	0.5762	0.080*
H12B	−0.3907	0.5370	0.6521	0.080*
C13	−0.3319 (6)	0.5609 (2)	0.4582 (5)	0.0566 (12)
H13	−0.3673	0.5271	0.4100	0.068*
C14	−0.1555 (5)	0.55858 (18)	0.4915 (4)	0.0462 (10)
H14	−0.1320	0.5340	0.5685	0.055*
C15	−0.2106 (6)	0.6491 (2)	0.4093 (4)	0.0500 (11)
C16	−0.3460 (6)	0.6124 (2)	0.3714 (5)	0.0575 (13)
C17	−0.4607 (8)	0.6273 (3)	0.2837 (6)	0.091 (2)
H17A	−0.4583	0.6625	0.2428	0.109*
H17B	−0.5426	0.6025	0.2638	0.109*
C18	0.2971 (7)	0.6944 (3)	0.9021 (5)	0.0727 (16)
H18A	0.2405	0.7292	0.9077	0.087*
H18B	0.3548	0.6935	0.8199	0.087*
H18C	0.3692	0.6913	0.9774	0.087*
C19	0.2760 (6)	0.5904 (2)	0.9127 (5)	0.0645 (14)
H19A	0.3420	0.5913	0.9922	0.077*
H19B	0.3405	0.5874	0.8346	0.077*
H19C	0.2064	0.5587	0.9166	0.077*
C20	−0.0951 (6)	0.5615 (2)	0.8243 (5)	0.0592 (13)
H20A	−0.0239	0.5425	0.7655	0.071*
H20B	−0.1990	0.5461	0.8125	0.071*
H20C	−0.0604	0.5565	0.9161	0.071*
C21	0.0542 (7)	0.5098 (2)	0.3887 (5)	0.0637 (14)
C22	0.1285 (10)	0.4971 (3)	0.2562 (7)	0.106 (3)
H22A	0.2276	0.4786	0.2717	0.128*
H22B	0.1453	0.5316	0.2081	0.128*
H22C	0.0599	0.4731	0.2041	0.128*
O2'	0.3469 (4)	0.85034 (16)	0.0269 (3)	0.0586 (9)
H2O'	0.3975	0.8477	−0.0424	0.070*
O3'	0.6721 (5)	0.77771 (15)	−0.0252 (4)	0.0660 (10)
O4'	0.5734 (4)	0.93369 (14)	−0.0081 (3)	0.0550 (9)
O5'	0.4016 (6)	0.9800 (2)	0.1187 (4)	0.1003 (16)
O1'	0.3864 (11)	0.8451 (4)	0.7516 (5)	0.090 (3)	0.829 (19)
C1'	0.6870 (10)	0.8126 (4)	0.5231 (7)	0.064 (2)	0.829 (19)
H1'1	0.7421	0.7807	0.4855	0.077*	0.829 (19)
H1'2	0.7649	0.8368	0.5661	0.077*	0.829 (19)
C2'	0.5725 (10)	0.7913 (5)	0.6304 (8)	0.072 (3)	0.829 (19)
H2'1	0.5420	0.7531	0.6076	0.087*	0.829 (19)
H2'2	0.6284	0.7900	0.7164	0.087*	0.829 (19)
O1*	0.350 (5)	0.818 (2)	0.746 (3)	0.090 (3)	0.171 (19)
C1*	0.666 (8)	0.806 (2)	0.521 (2)	0.064 (2)	0.171 (19)
H1*1	0.6369	0.7680	0.5005	0.077*	0.171 (19)
H1*2	0.7805	0.8085	0.5255	0.077*	0.171 (19)
C2*	0.599 (3)	0.8233 (17)	0.658 (2)	0.039 (8)	0.171 (19)
H2*1	0.6315	0.7962	0.7264	0.047*	0.171 (19)
H2*2	0.6387	0.8599	0.6848	0.047*	0.171 (19)
C3'	0.4290 (6)	0.8247 (2)	0.6466 (4)	0.0588 (13)
C4'	0.3273 (6)	0.8314 (2)	0.5166 (4)	0.0476 (11)
C5'	0.4329 (5)	0.82451 (17)	0.3899 (4)	0.0399 (9)
H5'	0.4410	0.7839	0.3754	0.048*
C6'	0.3526 (5)	0.84739 (19)	0.2639 (4)	0.0438 (10)
H6'1	0.3479	0.8881	0.2694	0.053*
H6'2	0.2454	0.8333	0.2583	0.053*
C7'	0.4394 (5)	0.83058 (19)	0.1374 (4)	0.0416 (9)
H7'	0.4407	0.7894	0.1331	0.050*
C8'	0.6112 (5)	0.85099 (16)	0.1395 (4)	0.0373 (9)
C9'	0.6931 (5)	0.83068 (19)	0.2744 (4)	0.0429 (10)
H9'	0.6895	0.7895	0.2694	0.051*
C10'	0.6046 (5)	0.84534 (16)	0.4075 (3)	0.0415 (10)
C11'	0.8721 (5)	0.8451 (2)	0.2767 (5)	0.0597 (13)
H11C	0.9092	0.8451	0.3697	0.072*
H11D	0.9275	0.8154	0.2305	0.072*
C12'	0.9178 (6)	0.9010 (3)	0.2136 (5)	0.0667 (14)
H12C	0.8945	0.9313	0.2754	0.080*
H12D	1.0302	0.9013	0.1977	0.080*
C13'	0.8294 (6)	0.9105 (2)	0.0819 (5)	0.0585 (12)
H13'	0.8646	0.9449	0.0370	0.070*
C14'	0.6525 (5)	0.91288 (19)	0.1136 (4)	0.0459 (10)
H14'	0.6315	0.9366	0.1919	0.055*
C15'	0.7050 (6)	0.8232 (2)	0.0252 (4)	0.0501 (11)
C16'	0.8382 (6)	0.8602 (2)	−0.0094 (5)	0.0587 (13)
C17'	0.9457 (7)	0.8461 (3)	−0.0995 (6)	0.088 (2)
H17C	0.9389	0.8117	−0.1437	0.106*
H17D	1.0277	0.8707	−0.1183	0.106*
C18'	0.2105 (7)	0.7819 (3)	0.5205 (6)	0.0732 (16)
H18D	0.1380	0.7875	0.5924	0.088*
H18E	0.2674	0.7475	0.5350	0.088*
H18F	0.1532	0.7798	0.4363	0.088*
C19'	0.2339 (6)	0.8872 (2)	0.5239 (5)	0.0613 (13)
H19D	0.1804	0.8892	0.6081	0.074*
H19E	0.1581	0.8887	0.4510	0.074*
H19F	0.3054	0.9183	0.5170	0.074*
C20'	0.6079 (6)	0.9084 (2)	0.4436 (5)	0.0559 (12)
H20D	0.5455	0.9290	0.3788	0.067*
H20E	0.7146	0.9217	0.4427	0.067*
H20F	0.5657	0.9137	0.5317	0.067*
C21'	0.4459 (7)	0.9658 (2)	0.0084 (5)	0.0643 (14)
C22'	0.3709 (9)	0.9785 (3)	−0.1242 (7)	0.095 (2)
H22D	0.2715	0.9594	−0.1315	0.114*
H22E	0.4384	0.9661	−0.1948	0.114*
H22F	0.3542	1.0183	−0.1320	0.114*

	U11	U22	U33	U12	U13	U23
O2	0.053 (2)	0.099 (3)	0.0356 (15)	−0.0010 (19)	0.0084 (15)	0.0041 (16)
O3	0.087 (3)	0.059 (2)	0.057 (2)	0.0069 (19)	−0.0092 (19)	0.0131 (17)
O4	0.063 (2)	0.0525 (18)	0.0430 (16)	0.0125 (16)	−0.0033 (15)	−0.0103 (13)
O5	0.112 (4)	0.113 (4)	0.076 (3)	0.068 (3)	0.006 (3)	0.016 (2)
O1	0.120 (4)	0.138 (8)	0.033 (2)	0.059 (6)	0.007 (2)	0.027 (4)
C1	0.051 (3)	0.097 (5)	0.046 (3)	0.013 (3)	0.007 (2)	−0.016 (3)
C2	0.095 (6)	0.097 (8)	0.038 (4)	0.032 (7)	0.001 (4)	−0.015 (5)
O1"	0.120 (4)	0.138 (8)	0.033 (2)	0.059 (6)	0.007 (2)	0.027 (4)
C1"	0.051 (3)	0.097 (5)	0.046 (3)	0.013 (3)	0.007 (2)	−0.016 (3)
C2"	0.095 (6)	0.097 (8)	0.038 (4)	0.032 (7)	0.001 (4)	−0.015 (5)
C3	0.069 (4)	0.076 (3)	0.033 (2)	0.003 (3)	−0.006 (2)	0.000 (2)
C4	0.056 (3)	0.064 (3)	0.037 (2)	−0.004 (2)	0.002 (2)	0.002 (2)
C5	0.045 (2)	0.038 (2)	0.0333 (18)	−0.0027 (18)	−0.0041 (17)	0.0023 (16)
C6	0.037 (2)	0.061 (3)	0.036 (2)	−0.006 (2)	0.0068 (18)	0.0014 (19)
C7	0.050 (3)	0.053 (2)	0.0302 (18)	0.002 (2)	0.0048 (18)	0.0022 (17)
C8	0.038 (2)	0.043 (2)	0.0332 (18)	0.0036 (18)	−0.0027 (17)	−0.0001 (16)
C9	0.041 (2)	0.046 (2)	0.046 (2)	0.0038 (19)	0.0025 (19)	−0.0091 (18)
C10	0.044 (2)	0.047 (2)	0.037 (2)	−0.001 (2)	0.0069 (18)	0.0002 (18)
C11	0.037 (3)	0.088 (4)	0.056 (3)	0.006 (3)	0.005 (2)	−0.015 (3)
C12	0.044 (3)	0.088 (4)	0.069 (3)	−0.018 (3)	0.003 (2)	−0.013 (3)
C13	0.049 (3)	0.060 (3)	0.061 (3)	−0.007 (2)	−0.005 (2)	−0.016 (2)
C14	0.054 (3)	0.042 (2)	0.042 (2)	0.001 (2)	0.003 (2)	−0.0048 (18)
C15	0.059 (3)	0.052 (3)	0.039 (2)	0.015 (2)	−0.001 (2)	−0.003 (2)
C16	0.048 (3)	0.068 (3)	0.057 (3)	0.011 (2)	−0.009 (2)	−0.011 (2)
C17	0.068 (4)	0.103 (5)	0.100 (5)	0.016 (4)	−0.034 (4)	−0.010 (4)
C18	0.065 (4)	0.098 (4)	0.055 (3)	−0.025 (3)	−0.010 (3)	−0.003 (3)
C19	0.055 (3)	0.088 (4)	0.051 (3)	0.011 (3)	−0.012 (2)	0.011 (2)
C20	0.059 (3)	0.066 (3)	0.052 (3)	−0.015 (2)	−0.001 (2)	0.015 (2)
C21	0.070 (4)	0.063 (3)	0.059 (3)	0.021 (3)	0.004 (3)	−0.006 (2)
C22	0.128 (7)	0.109 (5)	0.084 (4)	0.039 (5)	0.029 (4)	−0.035 (4)
O2'	0.0475 (19)	0.096 (3)	0.0321 (14)	0.0080 (18)	−0.0098 (13)	0.0048 (16)
O3'	0.075 (3)	0.063 (2)	0.060 (2)	0.0144 (19)	0.0030 (18)	−0.0161 (17)
O4'	0.063 (2)	0.0590 (19)	0.0433 (16)	0.0187 (17)	0.0021 (15)	0.0113 (14)
O5'	0.121 (4)	0.108 (3)	0.072 (3)	0.068 (3)	−0.003 (3)	−0.019 (2)
O1'	0.115 (5)	0.125 (7)	0.0296 (18)	0.023 (5)	−0.004 (2)	−0.004 (3)
C1'	0.062 (5)	0.087 (4)	0.043 (2)	0.012 (4)	−0.013 (2)	0.010 (3)
C2'	0.084 (6)	0.085 (7)	0.048 (4)	0.009 (5)	−0.009 (4)	0.025 (4)
O1*	0.115 (5)	0.125 (7)	0.0296 (18)	0.023 (5)	−0.004 (2)	−0.004 (3)
C1*	0.062 (5)	0.087 (4)	0.043 (2)	0.012 (4)	−0.013 (2)	0.010 (3)
C2*	0.046 (16)	0.046 (19)	0.025 (11)	−0.016 (13)	−0.019 (10)	−0.005 (12)
C3'	0.075 (4)	0.067 (3)	0.033 (2)	−0.012 (3)	−0.002 (2)	0.005 (2)
C4'	0.053 (3)	0.054 (3)	0.035 (2)	−0.003 (2)	−0.0004 (19)	0.0050 (19)
C5'	0.047 (2)	0.042 (2)	0.0309 (18)	−0.0028 (18)	−0.0043 (17)	0.0004 (16)
C6'	0.040 (2)	0.056 (3)	0.035 (2)	−0.003 (2)	−0.0070 (18)	0.0007 (19)
C7'	0.041 (2)	0.052 (2)	0.0312 (19)	0.000 (2)	−0.0090 (17)	−0.0043 (18)
C8'	0.038 (2)	0.039 (2)	0.0343 (19)	0.0083 (18)	−0.0045 (17)	0.0039 (16)
C9'	0.041 (2)	0.047 (2)	0.041 (2)	0.0046 (19)	−0.0070 (18)	0.0029 (18)
C10'	0.043 (2)	0.047 (2)	0.034 (2)	−0.0011 (19)	−0.0075 (17)	0.0014 (17)
C11'	0.040 (3)	0.082 (3)	0.057 (3)	0.010 (3)	−0.010 (2)	0.004 (2)
C12'	0.041 (3)	0.092 (4)	0.067 (3)	−0.010 (3)	0.001 (2)	0.004 (3)
C13'	0.058 (3)	0.059 (3)	0.059 (3)	−0.001 (2)	0.006 (2)	0.007 (2)
C14'	0.047 (3)	0.049 (2)	0.041 (2)	0.004 (2)	−0.004 (2)	0.0032 (19)
C15'	0.047 (3)	0.062 (3)	0.041 (2)	0.014 (2)	−0.002 (2)	0.006 (2)
C16'	0.052 (3)	0.079 (3)	0.045 (2)	0.014 (3)	0.004 (2)	0.011 (2)
C17'	0.071 (4)	0.115 (5)	0.080 (4)	0.029 (4)	0.029 (3)	0.008 (4)
C18'	0.078 (4)	0.084 (4)	0.057 (3)	−0.028 (3)	0.006 (3)	0.009 (3)
C19'	0.056 (3)	0.076 (3)	0.052 (3)	0.013 (3)	0.007 (2)	0.001 (2)
C20'	0.059 (3)	0.055 (3)	0.054 (3)	−0.012 (2)	−0.001 (2)	−0.013 (2)
C21'	0.075 (4)	0.051 (3)	0.066 (3)	0.024 (3)	−0.006 (3)	0.006 (2)
C22'	0.092 (5)	0.100 (5)	0.091 (4)	0.042 (4)	−0.018 (4)	0.027 (4)

O2—C7	1.416 (5)	O2'—C7'	1.417 (5)
O2—H2O	0.8200	O2'—H2O'	0.8200
O3—C15	1.218 (6)	O3'—C15'	1.223 (6)
O4—C21	1.344 (6)	O4'—C21'	1.337 (6)
O4—C14	1.447 (5)	O4'—C14'	1.458 (5)
O5—C21	1.195 (6)	O5'—C21'	1.213 (6)
O1—C3	1.212 (3)	O1'—C3'	1.211 (3)
C1—C2	1.540 (3)	C1'—C2'	1.540 (3)
C1—C10	1.543 (3)	C1'—C10'	1.543 (3)
C1—H1A	0.9700	C1'—H1'1	0.9700
C1—H1B	0.9700	C1'—H1'2	0.9700
C2—C3	1.488 (11)	C2'—C3'	1.464 (3)
C2—H2A	0.9700	C2'—H2'1	0.9700
C2—H2B	0.9700	C2'—H2'2	0.9700
O1"—C3	1.212 (3)	O1*—C3'	1.210 (3)
C1"—C2"	1.540 (3)	C1*—C2*	1.540 (3)
C1"—C10	1.541 (3)	C1*—C10'	1.541 (3)
C1"—H1C	0.9700	C1*—H1*1	0.9700
C1"—H1D	0.9700	C1*—H1*2	0.9700
C2"—C3	1.45 (3)	C2*—C3'	1.45 (3)
C2"—H2C	0.9700	C2*—H2*1	0.9700
C2"—H2D	0.9700	C2*—H2*2	0.9700
C3—C4	1.499 (6)	C3'—C4'	1.548 (6)
C4—C19	1.532 (7)	C4'—C18'	1.541 (7)
C4—C18	1.553 (7)	C4'—C19'	1.548 (7)
C4—C5	1.565 (6)	C4'—C5'	1.567 (6)
C5—C6	1.530 (5)	C5'—C6'	1.515 (5)
C5—C10	1.553 (6)	C5'—C10'	1.545 (6)
C5—H5	0.9800	C5'—H5'	0.9800
C6—C7	1.502 (6)	C6'—C7'	1.521 (5)
C6—H6A	0.9700	C6'—H6'1	0.9700
C6—H6B	0.9700	C6'—H6'2	0.9700
C7—C8	1.533 (6)	C7'—C8'	1.536 (6)
C7—H7	0.9800	C7'—H7'	0.9800
C8—C15	1.533 (6)	C8'—C14'	1.536 (6)
C8—C14	1.541 (6)	C8'—C15'	1.546 (6)
C8—C9	1.580 (5)	C8'—C9'	1.574 (5)
C9—C11	1.562 (6)	C9'—C11'	1.558 (6)
C9—C10	1.563 (6)	C9'—C10'	1.571 (5)
C9—H9	0.9800	C9'—H9'	0.9800
C10—C20	1.543 (7)	C10'—C20'	1.542 (6)
C11—C12	1.524 (8)	C11'—C12'	1.521 (8)
C11—H11A	0.9700	C11'—H11C	0.9700
C11—H11B	0.9700	C11'—H11D	0.9700
C12—C13	1.540 (7)	C12'—C13'	1.512 (8)
C12—H12A	0.9700	C12'—H12C	0.9700
C12—H12B	0.9700	C12'—H12D	0.9700
C13—C16	1.502 (7)	C13'—C16'	1.504 (7)
C13—C14	1.528 (7)	C13'—C14'	1.540 (7)
C13—H13	0.9800	C13'—H13'	0.9800
C14—H14	0.9800	C14'—H14'	0.9800
C15—C16	1.487 (7)	C15'—C16'	1.478 (7)
C16—C17	1.342 (8)	C16'—C17'	1.332 (7)
C17—H17A	0.9300	C17'—H17C	0.9300
C17—H17B	0.9300	C17'—H17D	0.9300
C18—H18A	0.9600	C18'—H18D	0.9600
C18—H18B	0.9600	C18'—H18E	0.9600
C18—H18C	0.9600	C18'—H18F	0.9600
C19—H19A	0.9600	C19'—H19D	0.9600
C19—H19B	0.9600	C19'—H19E	0.9600
C19—H19C	0.9600	C19'—H19F	0.9600
C20—H20A	0.9600	C20'—H20D	0.9600
C20—H20B	0.9600	C20'—H20E	0.9600
C20—H20C	0.9600	C20'—H20F	0.9600
C21—C22	1.499 (8)	C21'—C22'	1.482 (8)
C22—H22A	0.9600	C22'—H22D	0.9600
C22—H22B	0.9600	C22'—H22E	0.9600
C22—H22C	0.9600	C22'—H22F	0.9600
C7—O2—H2O	109.5	C7'—O2'—H2O'	109.5
C21—O4—C14	116.2 (4)	C21'—O4'—C14'	117.0 (4)
C2—C1—C10	115.1 (7)	C2'—C1'—C10'	113.4 (5)
C2—C1—H1A	108.5	C2'—C1'—H1'1	108.9
C10—C1—H1A	108.5	C10'—C1'—H1'1	108.9
C2—C1—H1B	108.5	C2'—C1'—H1'2	108.9
C10—C1—H1B	108.5	C10'—C1'—H1'2	108.9
H1A—C1—H1B	107.5	H1'1—C1'—H1'2	107.7
C3—C2—C1	116.7 (7)	C3'—C2'—C1'	115.7 (5)
C3—C2—H2A	108.1	C3'—C2'—H2'1	108.4
C1—C2—H2A	108.1	C1'—C2'—H2'1	108.4
C3—C2—H2B	108.1	C3'—C2'—H2'2	108.4
C1—C2—H2B	108.1	C1'—C2'—H2'2	108.4
H2A—C2—H2B	107.3	H2'1—C2'—H2'2	107.4
C2"—C1"—C10	112.6 (12)	C2*—C1*—C10'	111.4 (16)
C2"—C1"—H1C	109.1	C2*—C1*—H1*1	109.3
C10—C1"—H1C	109.1	C10'—C1*—H1*1	109.3
C2"—C1"—H1D	109.1	C2*—C1*—H1*2	109.3
C10—C1"—H1D	109.1	C10'—C1*—H1*2	109.3
H1C—C1"—H1D	107.8	H1*1—C1*—H1*2	108.0
C3—C2"—C1"	112.7 (19)	C3'—C2*—C1*	109 (3)
C3—C2"—H2C	109.0	C3'—C2*—H2*1	110.0
C1"—C2"—H2C	109.0	C1*—C2*—H2*1	110.0
C3—C2"—H2D	109.0	C3'—C2*—H2*2	110.0
C1"—C2"—H2D	109.0	C1*—C2*—H2*2	110.0
H2C—C2"—H2D	107.8	H2*1—C2*—H2*2	108.3
O1"—C3—O1	43.4 (7)	O1*—C3'—O1'	34 (2)
O1"—C3—C2"	112.3 (12)	O1*—C3'—C2*	120 (2)
O1—C3—C2"	102.0 (10)	O1'—C3'—C2*	104.7 (12)
O1"—C3—C2	106.7 (9)	O1*—C3'—C2'	120 (2)
O1—C3—C2	123.3 (6)	O1'—C3'—C2'	125.0 (7)
C2"—C3—C2	35.4 (9)	C2*—C3'—C2'	33.5 (12)
O1"—C3—C4	121.0 (9)	O1*—C3'—C4'	113 (2)
O1—C3—C4	120.7 (6)	O1'—C3'—C4'	120.4 (5)
C2"—C3—C4	126.3 (8)	C2*—C3'—C4'	127.6 (10)
C2—C3—C4	115.9 (5)	C2'—C3'—C4'	114.6 (5)
C3—C4—C19	109.3 (4)	C18'—C4'—C19'	108.9 (4)
C3—C4—C18	106.0 (4)	C18'—C4'—C3'	104.4 (4)
C19—C4—C18	107.2 (4)	C19'—C4'—C3'	109.2 (4)
C3—C4—C5	111.8 (4)	C18'—C4'—C5'	108.5 (4)
C19—C4—C5	114.1 (4)	C19'—C4'—C5'	115.3 (3)
C18—C4—C5	108.0 (4)	C3'—C4'—C5'	109.9 (4)
C6—C5—C10	110.9 (3)	C6'—C5'—C10'	112.8 (3)
C6—C5—C4	113.5 (4)	C6'—C5'—C4'	111.8 (4)
C10—C5—C4	115.4 (3)	C10'—C5'—C4'	115.3 (3)
C6—C5—H5	105.4	C6'—C5'—H5'	105.3
C10—C5—H5	105.4	C10'—C5'—H5'	105.3
C4—C5—H5	105.4	C4'—C5'—H5'	105.3
C7—C6—C5	112.1 (4)	C5'—C6'—C7'	111.8 (4)
C7—C6—H6A	109.2	C5'—C6'—H6'1	109.3
C5—C6—H6A	109.2	C7'—C6'—H6'1	109.3
C7—C6—H6B	109.2	C5'—C6'—H6'2	109.3
C5—C6—H6B	109.2	C7'—C6'—H6'2	109.3
H6A—C6—H6B	107.9	H6'1—C6'—H6'2	107.9
O2—C7—C6	106.6 (4)	O2'—C7'—C6'	106.4 (3)
O2—C7—C8	115.1 (4)	O2'—C7'—C8'	114.7 (3)
C6—C7—C8	113.5 (3)	C6'—C7'—C8'	112.3 (3)
O2—C7—H7	107.1	O2'—C7'—H7'	107.7
C6—C7—H7	107.1	C6'—C7'—H7'	107.7
C8—C7—H7	107.1	C8'—C7'—H7'	107.7
C15—C8—C7	110.2 (4)	C14'—C8'—C7'	121.3 (3)
C15—C8—C14	99.6 (3)	C14'—C8'—C15'	99.5 (3)
C7—C8—C14	121.8 (4)	C7'—C8'—C15'	110.9 (3)
C15—C8—C9	105.7 (3)	C14'—C8'—C9'	109.8 (3)
C7—C8—C9	108.0 (3)	C7'—C8'—C9'	108.6 (3)
C14—C8—C9	110.3 (3)	C15'—C8'—C9'	105.6 (3)
C11—C9—C10	114.7 (4)	C11'—C9'—C10'	114.8 (4)
C11—C9—C8	110.8 (3)	C11'—C9'—C8'	111.1 (3)
C10—C9—C8	115.9 (3)	C10'—C9'—C8'	116.0 (3)
C11—C9—H9	104.7	C11'—C9'—H9'	104.5
C10—C9—H9	104.7	C10'—C9'—H9'	104.5
C8—C9—H9	104.7	C8'—C9'—H9'	104.5
C1"—C10—C20	106.6 (18)	C1*—C10'—C20'	114 (2)
C1"—C10—C1	4.2 (17)	C1*—C10'—C1'	8(3)
C20—C10—C1	109.7 (9)	C20'—C10'—C1'	108.2 (5)
C1"—C10—C5	107.1 (16)	C1*—C10'—C5'	101 (3)
C20—C10—C5	111.7 (4)	C20'—C10'—C5'	110.6 (4)
C1—C10—C5	108.0 (7)	C1'—C10'—C5'	109.6 (5)
C1"—C10—C9	109.7 (9)	C1*—C10'—C9'	108.7 (12)
C20—C10—C9	114.3 (4)	C20'—C10'—C9'	113.8 (3)
C1—C10—C9	105.6 (6)	C1'—C10'—C9'	107.2 (4)
C5—C10—C9	107.2 (3)	C5'—C10'—C9'	107.3 (3)
C12—C11—C9	117.1 (4)	C12'—C11'—C9'	116.3 (4)
C12—C11—H11A	108.0	C12'—C11'—H11C	108.2
C9—C11—H11A	108.0	C9'—C11'—H11C	108.2
C12—C11—H11B	108.0	C12'—C11'—H11D	108.2
C9—C11—H11B	108.0	C9'—C11'—H11D	108.2
H11A—C11—H11B	107.3	H11C—C11'—H11D	107.4
C11—C12—C13	110.3 (4)	C13'—C12'—C11'	111.2 (4)
C11—C12—H12A	109.6	C13'—C12'—H12C	109.4
C13—C12—H12A	109.6	C11'—C12'—H12C	109.4
C11—C12—H12B	109.6	C13'—C12'—H12D	109.4
C13—C12—H12B	109.6	C11'—C12'—H12D	109.4
H12A—C12—H12B	108.1	H12C—C12'—H12D	108.0
C16—C13—C14	102.8 (4)	C16'—C13'—C12'	111.9 (4)
C16—C13—C12	112.0 (4)	C16'—C13'—C14'	102.2 (4)
C14—C13—C12	107.0 (4)	C12'—C13'—C14'	107.4 (4)
C16—C13—H13	111.5	C16'—C13'—H13'	111.6
C14—C13—H13	111.5	C12'—C13'—H13'	111.6
C12—C13—H13	111.5	C14'—C13'—H13'	111.6
O4—C14—C13	106.6 (4)	O4'—C14'—C8'	111.2 (4)
O4—C14—C8	110.8 (3)	O4'—C14'—C13'	106.2 (3)
C13—C14—C8	103.0 (4)	C8'—C14'—C13'	103.0 (3)
O4—C14—H14	112.0	O4'—C14'—H14'	112.0
C13—C14—H14	112.0	C8'—C14'—H14'	112.0
C8—C14—H14	112.0	C13'—C14'—H14'	112.0
O3—C15—C16	125.9 (5)	O3'—C15'—C16'	127.0 (4)
O3—C15—C8	125.3 (5)	O3'—C15'—C8'	124.2 (4)
C16—C15—C8	108.7 (4)	C16'—C15'—C8'	108.8 (4)
C17—C16—C15	123.8 (5)	C17'—C16'—C15'	122.9 (6)
C17—C16—C13	129.7 (6)	C17'—C16'—C13'	130.3 (6)
C15—C16—C13	106.3 (4)	C15'—C16'—C13'	106.7 (4)
C16—C17—H17A	120.0	C16'—C17'—H17C	120.0
C16—C17—H17B	120.0	C16'—C17'—H17D	120.0
H17A—C17—H17B	120.0	H17C—C17'—H17D	120.0
C4—C18—H18A	109.5	C4'—C18'—H18D	109.5
C4—C18—H18B	109.5	C4'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C4—C18—H18C	109.5	C4'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C4—C19—H19A	109.5	C4'—C19'—H19D	109.5
C4—C19—H19B	109.5	C4'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C4—C19—H19C	109.5	C4'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C10—C20—H20A	109.5	C10'—C20'—H20D	109.5
C10—C20—H20B	109.5	C10'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C10—C20—H20C	109.5	C10'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
O5—C21—O4	123.1 (5)	O5'—C21'—O4'	122.3 (5)
O5—C21—C22	126.1 (6)	O5'—C21'—C22'	127.6 (5)
O4—C21—C22	110.7 (5)	O4'—C21'—C22'	110.1 (5)
C21—C22—H22A	109.5	C21'—C22'—H22D	109.5
C21—C22—H22B	109.5	C21'—C22'—H22E	109.5
H22A—C22—H22B	109.5	H22D—C22'—H22E	109.5
C21—C22—H22C	109.5	C21'—C22'—H22F	109.5
H22A—C22—H22C	109.5	H22D—C22'—H22F	109.5
H22B—C22—H22C	109.5	H22E—C22'—H22F	109.5
C10—C1—C2—C3	−21 (2)	C10'—C1*—C2*—C3'	54 (6)
C10—C1"—C2"—C3	47 (4)	C1*—C2*—C3'—O1*	156 (4)
C1"—C2"—C3—O1"	147 (2)	C1*—C2*—C3'—O1'	−171 (3)
C1"—C2"—C3—O1	−169 (2)	C1*—C2*—C3'—C2'	56 (3)
C1"—C2"—C3—C2	59 (2)	C1*—C2*—C3'—C4'	−22 (4)
C1"—C2"—C3—C4	−26 (3)	C1'—C2'—C3'—O1*	−164 (3)
C1—C2—C3—O1"	−172.2 (14)	C1'—C2'—C3'—O1'	−124.4 (13)
C1—C2—C3—O1	−127.4 (14)	C1'—C2'—C3'—C2*	−64 (2)
C1—C2—C3—C2"	−67 (2)	C1'—C2'—C3'—C4'	57.3 (12)
C1—C2—C3—C4	49.8 (13)	O1*—C3'—C4'—C18'	−50 (3)
O1"—C3—C4—C19	80.5 (11)	O1'—C3'—C4'—C18'	−87.0 (8)
O1—C3—C4—C19	29.5 (9)	C2*—C3'—C4'—C18'	128 (2)
C2"—C3—C4—C19	−107.9 (14)	C2'—C3'—C4'—C18'	91.3 (7)
C2—C3—C4—C19	−147.8 (7)	O1*—C3'—C4'—C19'	66 (3)
O1"—C3—C4—C18	−34.7 (11)	O1'—C3'—C4'—C19'	29.4 (9)
O1—C3—C4—C18	−85.8 (8)	C2*—C3'—C4'—C19'	−116 (2)
C2"—C3—C4—C18	136.9 (14)	C2'—C3'—C4'—C19'	−152.3 (6)
C2—C3—C4—C18	97.0 (7)	O1*—C3'—C4'—C5'	−166 (3)
O1"—C3—C4—C5	−152.2 (10)	O1'—C3'—C4'—C5'	156.8 (8)
O1—C3—C4—C5	156.8 (7)	C2*—C3'—C4'—C5'	12 (2)
C2"—C3—C4—C5	19.4 (15)	C2'—C3'—C4'—C5'	−24.8 (7)
C2—C3—C4—C5	−20.5 (8)	C18'—C4'—C5'—C6'	83.3 (5)
C3—C4—C5—C6	−163.8 (4)	C19'—C4'—C5'—C6'	−39.1 (5)
C19—C4—C5—C6	−39.2 (5)	C3'—C4'—C5'—C6'	−163.1 (4)
C18—C4—C5—C6	79.9 (5)	C18'—C4'—C5'—C10'	−146.2 (4)
C3—C4—C5—C10	−34.3 (5)	C19'—C4'—C5'—C10'	91.3 (5)
C19—C4—C5—C10	90.3 (5)	C3'—C4'—C5'—C10'	−32.6 (5)
C18—C4—C5—C10	−150.6 (4)	C10'—C5'—C6'—C7'	59.5 (5)
C10—C5—C6—C7	60.0 (5)	C4'—C5'—C6'—C7'	−168.8 (4)
C4—C5—C6—C7	−168.2 (4)	C5'—C6'—C7'—O2'	175.4 (3)
C5—C6—C7—O2	174.2 (3)	C5'—C6'—C7'—C8'	−58.4 (5)
C5—C6—C7—C8	−58.2 (5)	O2'—C7'—C8'—C14'	45.9 (5)
O2—C7—C8—C15	−70.4 (5)	C6'—C7'—C8'—C14'	−75.7 (5)
C6—C7—C8—C15	166.5 (3)	O2'—C7'—C8'—C15'	−70.0 (4)
O2—C7—C8—C14	45.5 (5)	C6'—C7'—C8'—C15'	168.3 (4)
C6—C7—C8—C14	−77.6 (5)	O2'—C7'—C8'—C9'	174.4 (3)
O2—C7—C8—C9	174.6 (3)	C6'—C7'—C8'—C9'	52.8 (4)
C6—C7—C8—C9	51.5 (5)	C14'—C8'—C9'—C11'	−50.7 (4)
C15—C8—C9—C11	57.6 (5)	C7'—C8'—C9'—C11'	174.6 (4)
C7—C8—C9—C11	175.5 (4)	C15'—C8'—C9'—C11'	55.7 (5)
C14—C8—C9—C11	−49.2 (5)	C14'—C8'—C9'—C10'	82.8 (4)
C15—C8—C9—C10	−169.5 (4)	C7'—C8'—C9'—C10'	−51.9 (4)
C7—C8—C9—C10	−51.6 (5)	C15'—C8'—C9'—C10'	−170.8 (4)
C14—C8—C9—C10	83.7 (4)	C2*—C1*—C10'—C20'	45 (6)
C2"—C1"—C10—C20	58 (3)	C2*—C1*—C10'—C1'	92 (11)
C2"—C1"—C10—C5	−61 (3)	C2*—C1*—C10'—C5'	−74 (5)
C2"—C1"—C10—C9	−177 (2)	C2*—C1*—C10'—C9'	173 (4)
C2—C1—C10—C20	91.6 (15)	C2'—C1'—C10'—C1*	−43 (9)
C2—C1—C10—C5	−30.3 (17)	C2'—C1'—C10'—C20'	92.9 (9)
C2—C1—C10—C9	−144.8 (13)	C2'—C1'—C10'—C5'	−27.7 (10)
C6—C5—C10—C1"	−173.6 (14)	C2'—C1'—C10'—C9'	−143.9 (8)
C4—C5—C10—C1"	55.6 (14)	C6'—C5'—C10'—C1*	−168.0 (14)
C6—C5—C10—C20	70.0 (4)	C4'—C5'—C10'—C1*	62.0 (14)
C4—C5—C10—C20	−60.8 (4)	C6'—C5'—C10'—C20'	70.6 (4)
C6—C5—C10—C1	−169.3 (8)	C4'—C5'—C10'—C20'	−59.4 (4)
C4—C5—C10—C1	59.9 (9)	C6'—C5'—C10'—C1'	−170.3 (5)
C6—C5—C10—C9	−55.9 (4)	C4'—C5'—C10'—C1'	59.7 (6)
C4—C5—C10—C9	173.3 (3)	C6'—C5'—C10'—C9'	−54.1 (4)
C11—C9—C10—C1"	−59 (2)	C4'—C5'—C10'—C9'	175.9 (3)
C8—C9—C10—C1"	170 (2)	C11'—C9'—C10'—C1*	−67 (3)
C11—C9—C10—C20	61.0 (5)	C8'—C9'—C10'—C1*	161 (3)
C8—C9—C10—C20	−70.1 (5)	C11'—C9'—C10'—C20'	61.1 (5)
C11—C9—C10—C1	−59.7 (10)	C8'—C9'—C10'—C20'	−70.7 (5)
C8—C9—C10—C1	169.2 (9)	C11'—C9'—C10'—C1'	−58.6 (6)
C11—C9—C10—C5	−174.7 (4)	C8'—C9'—C10'—C1'	169.7 (6)
C8—C9—C10—C5	54.2 (4)	C11'—C9'—C10'—C5'	−176.3 (4)
C10—C9—C11—C12	−97.5 (5)	C8'—C9'—C10'—C5'	52.0 (4)
C8—C9—C11—C12	36.1 (6)	C10'—C9'—C11'—C12'	−96.8 (5)
C9—C11—C12—C13	−42.9 (7)	C8'—C9'—C11'—C12'	37.2 (6)
C11—C12—C13—C16	−49.3 (6)	C9'—C11'—C12'—C13'	−43.4 (6)
C11—C12—C13—C14	62.6 (6)	C11'—C12'—C13'—C16'	−49.3 (6)
C21—O4—C14—C13	−149.3 (4)	C11'—C12'—C13'—C14'	62.1 (5)
C21—O4—C14—C8	99.4 (5)	C21'—O4'—C14'—C8'	102.2 (5)
C16—C13—C14—O4	−74.1 (4)	C21'—O4'—C14'—C13'	−146.4 (4)
C12—C13—C14—O4	167.8 (4)	C7'—C8'—C14'—O4'	−49.8 (5)
C16—C13—C14—C8	42.5 (4)	C15'—C8'—C14'—O4'	71.8 (4)
C12—C13—C14—C8	−75.6 (4)	C9'—C8'—C14'—O4'	−177.8 (3)
C15—C8—C14—O4	71.9 (4)	C7'—C8'—C14'—C13'	−163.2 (4)
C7—C8—C14—O4	−49.2 (5)	C15'—C8'—C14'—C13'	−41.6 (4)
C9—C8—C14—O4	−177.3 (3)	C9'—C8'—C14'—C13'	68.9 (4)
C15—C8—C14—C13	−41.7 (4)	C16'—C13'—C14'—O4'	−73.8 (4)
C7—C8—C14—C13	−162.8 (4)	C12'—C13'—C14'—O4'	168.3 (4)
C9—C8—C14—C13	69.1 (4)	C16'—C13'—C14'—C8'	43.1 (4)
C7—C8—C15—O3	−24.0 (6)	C12'—C13'—C14'—C8'	−74.7 (4)
C14—C8—C15—O3	−153.2 (4)	C14'—C8'—C15'—O3'	−154.8 (5)
C9—C8—C15—O3	92.4 (5)	C7'—C8'—C15'—O3'	−26.0 (6)
C7—C8—C15—C16	155.7 (3)	C9'—C8'—C15'—O3'	91.4 (5)
C14—C8—C15—C16	26.5 (4)	C14'—C8'—C15'—C16'	25.8 (4)
C9—C8—C15—C16	−87.9 (4)	C7'—C8'—C15'—C16'	154.7 (4)
O3—C15—C16—C17	−6.3 (8)	C9'—C8'—C15'—C16'	−87.9 (4)
C8—C15—C16—C17	174.1 (5)	O3'—C15'—C16'—C17'	−3.1 (8)
O3—C15—C16—C13	178.7 (4)	C8'—C15'—C16'—C17'	176.2 (5)
C8—C15—C16—C13	−1.0 (5)	O3'—C15'—C16'—C13'	−179.1 (5)
C14—C13—C16—C17	159.8 (5)	C8'—C15'—C16'—C13'	0.3 (5)
C12—C13—C16—C17	−85.6 (7)	C12'—C13'—C16'—C17'	−87.3 (7)
C14—C13—C16—C15	−25.4 (4)	C14'—C13'—C16'—C17'	158.1 (6)
C12—C13—C16—C15	89.1 (5)	C12'—C13'—C16'—C15'	88.2 (5)
C14—O4—C21—O5	6.5 (8)	C14'—C13'—C16'—C15'	−26.4 (5)
C14—O4—C21—C22	−175.3 (5)	C14'—O4'—C21'—O5'	4.0 (8)
C10'—C1'—C2'—C3'	−28.0 (14)	C14'—O4'—C21'—C22'	−174.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.82	2.09	2.747 (6)	137
O2—H2O···O1i	0.82	2.09	2.747 (6)	137
O2'—H2O'···O1'i	0.82	2.05	2.764 (5)	146
O2'—H2O'···O1*i	0.82	2.24	2.89 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.82	2.09	2.747 (6)	137
O2—H2O⋯O1i	0.82	2.09	2.747 (6)	137
O2′—H2O′⋯O1′i	0.82	2.05	2.764 (5)	146
O2′—H2O′⋯O1*i	0.82	2.24	2.89 (3)	136

Symmetry code: (i) .