(2S,4aR,6aR,7R,9S,10aS,10bR)-7-Carb-oxy-2-(3-fur-yl)-6a,10b-dimethyl-4,10-dioxoperhydro-benzo[f]isochromen-9-yl acetate.

The asymmetric unit of the title compound, C(22)H(26)O(8), contains two crystallographically independent mol-ecules with closely comparable conformations (r.m.s. overlay = 0.54 Å for 30 non-H atoms). All six-membered rings display chair conformations, with a slight distortion for the lactone ring. The mol-ecules are connected by O-H⋯O hydrogen bonds into chains along [010], with the independent mol-ecules segregated into separate chains. The two mol-ecules in the asymmetric unit face each other in a head-to-tail fashion, with the furan ring of one mol-ecule turned towards the carboxylic acid terminal of the other mol-ecule.

Related literature

For the biosynthesis of Salvinorin A, see: Kutrzeba et al. (2007 ▶). For the isolation of Salvinorin A and further synthesis details, see: Lee, Karnati et al. (2005 ▶); Lee, He et al. (2005 ▶); Stewart (2005 ▶). For details on epimerization at the C-8 stereogenic center, see: Harding et al. (2005 ▶).

Experimental

Crystal data

C22H26O8

M = 418.43

Monoclinic,

a = 11.2735 (6) Å

b = 16.8015 (9) Å

c = 11.3765 (6) Å

β = 111.934 (3)°

V = 1998.86 (18) Å3

Z = 4

Cu Kα radiation

μ = 0.89 mm−1

T = 100 (2) K

0.19 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: none

33644 measured reflections

7269 independent reflections

6962 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.074

S = 1.10

7269 reflections

549 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 3360 Friedel pairs

Flack parameter: −0.09 (13)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536809002074/bi2338sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002074/bi2338Isup2.hkl

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

C22H26O8	F(000) = 888
Mr = 418.43	Dx = 1.390 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 9847 reflections
a = 11.2735 (6) Å	θ = 4.2–69.3°
b = 16.8015 (9) Å	µ = 0.89 mm−1
c = 11.3765 (6) Å	T = 100 K
β = 111.934 (3)°	Block, colourless
V = 1998.86 (18) Å3	0.19 × 0.12 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	6962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Siemens KFF Cu 2 K90	Rint = 0.034
graphite	θmax = 69.7°, θmin = 4.2°
φ and ω scans	h = −13→13
33644 measured reflections	k = −20→20
7269 independent reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0314P)2 + 0.6446P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
7269 reflections	Δρmax = 0.22 e Å−3
549 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 3360 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (13)

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
C17	0.15137 (16)	0.28832 (12)	0.49869 (18)	0.0206 (4)
C21	−0.01037 (17)	0.36406 (10)	−0.21255 (17)	0.0184 (4)
C10	0.05570 (16)	0.40092 (10)	0.18239 (17)	0.0171 (4)
H10	0.1460	0.4079	0.1953	0.021*
C2	0.02643 (18)	0.44739 (11)	−0.03640 (17)	0.0200 (4)
H2	0.1187	0.4446	−0.0167	0.024*
C13	0.22704 (17)	0.12615 (11)	0.32982 (18)	0.0209 (4)
C3	−0.00836 (19)	0.53085 (11)	−0.00734 (19)	0.0216 (4)
H3A	−0.1005	0.5356	−0.0341	0.026*
H3B	0.0208	0.5699	−0.0533	0.026*
C2'	0.52134 (17)	0.21987 (11)	0.57588 (17)	0.0184 (4)
H2'	0.4293	0.2214	0.5260	0.022*
C7	0.07910 (19)	0.43150 (12)	0.44293 (18)	0.0230 (4)
H7A	−0.0087	0.4227	0.4347	0.028*
H7B	0.1289	0.4445	0.5307	0.028*
C1	−0.01037 (16)	0.38607 (10)	0.04262 (18)	0.0184 (4)
C14	0.25349 (19)	0.05608 (11)	0.4068 (2)	0.0260 (4)
H14	0.2213	0.0437	0.4688	0.031*
C6	0.08460 (18)	0.50046 (11)	0.35771 (18)	0.0220 (4)
H6A	0.1734	0.5116	0.3723	0.026*
H6B	0.0490	0.5475	0.3816	0.026*
C20	−0.08067 (17)	0.30143 (11)	0.25474 (18)	0.0200 (4)
H20A	−0.1174	0.2710	0.1782	0.030*
H20B	−0.1339	0.3466	0.2514	0.030*
H20C	−0.0744	0.2688	0.3261	0.030*
C12	0.13705 (17)	0.19141 (11)	0.33016 (17)	0.0198 (4)
H12	0.0513	0.1681	0.3033	0.024*
C5	0.01218 (16)	0.48472 (11)	0.21544 (17)	0.0188 (4)
C8	0.13200 (17)	0.35598 (11)	0.40574 (17)	0.0194 (4)
H8	0.2173	0.3698	0.4079	0.023*
C22	−0.09694 (18)	0.34694 (12)	−0.34524 (18)	0.0229 (4)
H22A	−0.0585	0.3075	−0.3809	0.034*
H22B	−0.1110	0.3949	−0.3946	0.034*
H22C	−0.1772	0.3274	−0.3459	0.034*
C9	0.05392 (16)	0.33013 (11)	0.26855 (17)	0.0177 (4)
C16	0.2942 (2)	0.11820 (13)	0.2545 (2)	0.0297 (4)
H16	0.2956	0.1555	0.1947	0.036*
C11	0.13007 (17)	0.26038 (11)	0.24228 (17)	0.0184 (4)
H11A	0.0888	0.2432	0.1550	0.022*
H11B	0.2158	0.2780	0.2547	0.022*
C18	0.03699 (18)	0.63203 (11)	0.17068 (19)	0.0227 (4)
C19	−0.13340 (17)	0.49154 (11)	0.18207 (19)	0.0220 (4)
H19A	−0.1551	0.4673	0.2478	0.033*
H19B	−0.1781	0.4649	0.1032	0.033*
H19C	−0.1576	0.5467	0.1744	0.033*
C4	0.05507 (17)	0.54636 (11)	0.13572 (19)	0.0202 (4)
H4	0.1472	0.5387	0.1585	0.024*
C15	0.33360 (19)	0.01185 (12)	0.3722 (2)	0.0296 (4)
H15	0.3667	−0.0370	0.4078	0.036*
O6	0.07866 (12)	0.32321 (8)	−0.14752 (12)	0.0217 (3)
O2	−0.04114 (12)	0.43277 (8)	−0.16960 (12)	0.0213 (3)
O4	0.17443 (12)	0.21504 (8)	0.46368 (12)	0.0229 (3)
O1	−0.08635 (12)	0.33368 (8)	−0.00508 (12)	0.0223 (3)
O7	0.11380 (13)	0.66586 (8)	0.25955 (14)	0.0309 (3)
O8	−0.07111 (13)	0.66571 (8)	0.09307 (13)	0.0281 (3)
H8A	−0.0768	0.7108	0.1179	0.042*
O3	0.15754 (12)	0.29677 (8)	0.60630 (12)	0.0246 (3)
O5	0.36018 (14)	0.04804 (9)	0.27771 (16)	0.0341 (3)
O4'	0.33614 (12)	0.44634 (7)	0.94502 (12)	0.0201 (3)
O3'	0.34121 (12)	0.36271 (7)	1.09451 (11)	0.0196 (3)
O2'	0.58986 (12)	0.23688 (7)	0.49500 (12)	0.0196 (3)
O1'	0.62849 (12)	0.33263 (8)	0.69732 (12)	0.0220 (3)
O8'	0.61511 (12)	0.00106 (7)	0.76991 (13)	0.0221 (3)
H8'	0.6248	−0.0429	0.8036	0.033*
O6'	0.45406 (13)	0.33889 (8)	0.41371 (13)	0.0287 (3)
O7'	0.42832 (12)	−0.00338 (7)	0.79601 (14)	0.0253 (3)
O5'	0.12409 (13)	0.60011 (8)	0.65291 (13)	0.0253 (3)
C17'	0.35561 (16)	0.37244 (10)	0.99497 (17)	0.0173 (4)
C9'	0.47726 (16)	0.33266 (10)	0.85748 (16)	0.0166 (4)
C3'	0.55835 (18)	0.13668 (10)	0.63141 (18)	0.0183 (4)
H3'1	0.6498	0.1341	0.6789	0.022*
H3'2	0.5364	0.0977	0.5638	0.022*
C21'	0.54660 (18)	0.30114 (11)	0.41882 (17)	0.0211 (4)
C1'	0.55327 (16)	0.27937 (10)	0.68357 (16)	0.0165 (3)
C13'	0.30056 (17)	0.53252 (10)	0.76765 (17)	0.0184 (4)
C16'	0.17621 (19)	0.54538 (11)	0.74745 (19)	0.0232 (4)
H16'	0.1320	0.5205	0.7917	0.028*
C14'	0.32831 (18)	0.58268 (11)	0.67923 (19)	0.0233 (4)
H14'	0.4063	0.5874	0.6695	0.028*
C12'	0.39011 (17)	0.47249 (11)	0.85204 (17)	0.0185 (4)
H12'	0.4720	0.4988	0.8979	0.022*
C4'	0.48608 (17)	0.11855 (10)	0.71910 (17)	0.0180 (4)
H4'	0.3949	0.1247	0.6677	0.022*
C11'	0.41363 (17)	0.40455 (10)	0.77524 (17)	0.0175 (4)
H11C	0.4677	0.4233	0.7318	0.021*
H11D	0.3327	0.3881	0.7114	0.021*
C5'	0.51693 (16)	0.17822 (10)	0.83185 (17)	0.0170 (4)
C15'	0.22000 (19)	0.62152 (11)	0.61333 (19)	0.0241 (4)
H15'	0.2113	0.6581	0.5493	0.029*
C6'	0.42909 (18)	0.16156 (11)	0.90570 (18)	0.0210 (4)
H6'1	0.3432	0.1515	0.8453	0.025*
H6'2	0.4585	0.1136	0.9555	0.025*
C10'	0.48050 (16)	0.26283 (10)	0.76984 (16)	0.0160 (4)
H10'	0.3914	0.2571	0.7116	0.019*
C22'	0.62893 (19)	0.31710 (12)	0.34423 (19)	0.0250 (4)
H22D	0.5924	0.3596	0.2853	0.037*
H22E	0.6341	0.2700	0.2987	0.037*
H22F	0.7131	0.3320	0.4008	0.037*
C8'	0.38328 (17)	0.30620 (10)	0.91970 (17)	0.0179 (4)
H8'1	0.3022	0.2948	0.8499	0.021*
C19'	0.65936 (17)	0.17049 (12)	0.92042 (18)	0.0225 (4)
H19D	0.6715	0.1930	1.0017	0.034*
H19E	0.7117	0.1984	0.8841	0.034*
H19F	0.6831	0.1153	0.9304	0.034*
C18'	0.50473 (17)	0.03240 (11)	0.76516 (17)	0.0183 (4)
C7'	0.42364 (19)	0.22877 (11)	0.99402 (18)	0.0223 (4)
H7'1	0.3630	0.2153	1.0329	0.027*
H7'2	0.5070	0.2355	1.0609	0.027*
C20'	0.60724 (17)	0.35762 (11)	0.95727 (18)	0.0213 (4)
H20D	0.5946	0.3991	1.0095	0.032*
H20E	0.6615	0.3767	0.9155	0.032*
H20F	0.6467	0.3126	1.0091	0.032*

	U11	U22	U33	U12	U13	U23
C17	0.0127 (8)	0.0244 (9)	0.0235 (10)	0.0000 (7)	0.0056 (7)	−0.0009 (8)
C21	0.0201 (9)	0.0183 (9)	0.0200 (9)	−0.0027 (7)	0.0112 (7)	0.0016 (8)
C10	0.0137 (8)	0.0179 (9)	0.0200 (9)	−0.0004 (7)	0.0066 (7)	−0.0011 (7)
C2	0.0213 (9)	0.0199 (9)	0.0175 (9)	0.0011 (7)	0.0057 (7)	−0.0005 (8)
C13	0.0174 (9)	0.0194 (9)	0.0232 (10)	−0.0038 (7)	0.0046 (7)	−0.0038 (8)
C3	0.0238 (9)	0.0183 (9)	0.0231 (9)	0.0012 (7)	0.0092 (7)	0.0023 (8)
C2'	0.0171 (9)	0.0194 (9)	0.0201 (9)	0.0009 (7)	0.0086 (7)	0.0024 (8)
C7	0.0256 (10)	0.0236 (9)	0.0198 (10)	0.0015 (8)	0.0084 (8)	−0.0037 (8)
C1	0.0154 (9)	0.0159 (9)	0.0252 (10)	0.0032 (7)	0.0092 (7)	−0.0010 (8)
C14	0.0279 (10)	0.0199 (9)	0.0272 (10)	−0.0013 (8)	0.0070 (8)	−0.0010 (8)
C6	0.0223 (9)	0.0205 (9)	0.0222 (9)	−0.0002 (7)	0.0069 (7)	−0.0053 (8)
C20	0.0180 (9)	0.0213 (9)	0.0210 (9)	−0.0006 (7)	0.0074 (7)	0.0021 (8)
C12	0.0188 (9)	0.0201 (9)	0.0197 (9)	−0.0014 (7)	0.0062 (7)	−0.0015 (7)
C5	0.0172 (9)	0.0176 (9)	0.0215 (9)	0.0008 (7)	0.0070 (7)	−0.0022 (8)
C8	0.0170 (9)	0.0217 (9)	0.0193 (9)	−0.0005 (7)	0.0064 (7)	0.0009 (8)
C22	0.0222 (9)	0.0272 (10)	0.0217 (9)	−0.0007 (8)	0.0108 (7)	0.0002 (8)
C9	0.0167 (8)	0.0181 (9)	0.0190 (9)	−0.0011 (7)	0.0076 (7)	−0.0012 (8)
C16	0.0296 (11)	0.0256 (10)	0.0369 (12)	0.0056 (8)	0.0160 (9)	0.0047 (9)
C11	0.0165 (8)	0.0203 (9)	0.0188 (9)	−0.0008 (7)	0.0071 (7)	−0.0023 (7)
C18	0.0200 (10)	0.0205 (9)	0.0285 (11)	−0.0002 (7)	0.0101 (8)	0.0022 (8)
C19	0.0185 (9)	0.0209 (9)	0.0286 (10)	0.0019 (7)	0.0111 (8)	−0.0006 (8)
C4	0.0160 (9)	0.0183 (9)	0.0264 (10)	−0.0006 (7)	0.0082 (7)	−0.0015 (8)
C15	0.0293 (11)	0.0166 (9)	0.0384 (12)	0.0013 (8)	0.0074 (9)	−0.0012 (9)
O6	0.0187 (6)	0.0196 (6)	0.0267 (7)	0.0009 (5)	0.0083 (5)	0.0008 (6)
O2	0.0253 (7)	0.0201 (6)	0.0174 (7)	0.0037 (5)	0.0069 (5)	0.0017 (5)
O4	0.0267 (7)	0.0221 (7)	0.0199 (7)	0.0041 (5)	0.0087 (5)	0.0027 (6)
O1	0.0206 (6)	0.0242 (7)	0.0212 (7)	−0.0027 (5)	0.0069 (5)	−0.0010 (6)
O7	0.0258 (7)	0.0225 (7)	0.0362 (8)	−0.0001 (6)	0.0021 (6)	−0.0070 (7)
O8	0.0260 (7)	0.0161 (6)	0.0354 (8)	0.0042 (5)	0.0039 (6)	−0.0037 (6)
O3	0.0232 (7)	0.0309 (7)	0.0199 (7)	0.0024 (5)	0.0084 (5)	0.0012 (6)
O5	0.0321 (8)	0.0276 (8)	0.0475 (9)	0.0056 (6)	0.0203 (7)	−0.0017 (7)
O4'	0.0247 (7)	0.0172 (6)	0.0204 (7)	0.0027 (5)	0.0107 (5)	0.0005 (5)
O3'	0.0228 (7)	0.0198 (6)	0.0177 (6)	−0.0008 (5)	0.0092 (5)	−0.0016 (5)
O2'	0.0233 (7)	0.0178 (6)	0.0203 (7)	0.0031 (5)	0.0112 (5)	0.0027 (5)
O1'	0.0227 (6)	0.0178 (6)	0.0292 (7)	−0.0028 (5)	0.0139 (6)	−0.0011 (6)
O8'	0.0239 (7)	0.0146 (6)	0.0318 (7)	0.0032 (5)	0.0149 (6)	0.0057 (6)
O6'	0.0266 (7)	0.0284 (7)	0.0334 (8)	0.0101 (6)	0.0138 (6)	0.0108 (6)
O7'	0.0249 (7)	0.0172 (6)	0.0395 (8)	−0.0016 (5)	0.0184 (6)	0.0005 (6)
O5'	0.0257 (7)	0.0217 (7)	0.0292 (7)	0.0066 (5)	0.0111 (6)	0.0031 (6)
C17'	0.0132 (8)	0.0174 (9)	0.0187 (9)	−0.0002 (6)	0.0030 (7)	−0.0002 (8)
C9'	0.0165 (8)	0.0155 (8)	0.0183 (9)	−0.0014 (7)	0.0071 (7)	−0.0020 (7)
C3'	0.0212 (9)	0.0148 (8)	0.0200 (9)	0.0003 (7)	0.0088 (7)	−0.0021 (7)
C21'	0.0239 (9)	0.0187 (9)	0.0183 (9)	0.0005 (7)	0.0051 (7)	0.0000 (7)
C1'	0.0151 (8)	0.0146 (8)	0.0190 (9)	0.0037 (7)	0.0055 (7)	0.0043 (7)
C13'	0.0243 (10)	0.0122 (8)	0.0193 (9)	−0.0006 (7)	0.0088 (7)	−0.0045 (7)
C16'	0.0292 (10)	0.0191 (9)	0.0250 (10)	0.0042 (8)	0.0145 (8)	0.0033 (8)
C14'	0.0247 (10)	0.0189 (9)	0.0287 (11)	−0.0008 (8)	0.0126 (8)	0.0007 (8)
C12'	0.0179 (9)	0.0170 (9)	0.0207 (9)	−0.0030 (7)	0.0075 (7)	−0.0018 (7)
C4'	0.0158 (9)	0.0162 (9)	0.0225 (9)	−0.0004 (7)	0.0079 (7)	0.0010 (8)
C11'	0.0192 (9)	0.0163 (8)	0.0193 (9)	−0.0012 (7)	0.0096 (7)	−0.0006 (7)
C5'	0.0180 (9)	0.0141 (8)	0.0187 (9)	0.0006 (7)	0.0069 (7)	0.0005 (7)
C15'	0.0329 (11)	0.0156 (9)	0.0261 (10)	−0.0005 (8)	0.0138 (8)	0.0015 (8)
C6'	0.0273 (10)	0.0149 (8)	0.0230 (9)	0.0016 (7)	0.0121 (8)	0.0030 (8)
C10'	0.0135 (8)	0.0154 (9)	0.0180 (9)	0.0003 (6)	0.0045 (7)	0.0007 (7)
C22'	0.0278 (10)	0.0249 (10)	0.0232 (10)	0.0016 (8)	0.0108 (8)	0.0059 (8)
C8'	0.0172 (8)	0.0178 (9)	0.0194 (9)	−0.0003 (7)	0.0077 (7)	−0.0008 (7)
C19'	0.0233 (10)	0.0189 (9)	0.0219 (10)	0.0037 (7)	0.0045 (7)	−0.0004 (8)
C18'	0.0212 (9)	0.0154 (9)	0.0187 (9)	−0.0017 (7)	0.0079 (7)	−0.0035 (7)
C7'	0.0275 (10)	0.0196 (9)	0.0227 (10)	0.0035 (7)	0.0128 (8)	0.0017 (8)
C20'	0.0198 (9)	0.0190 (9)	0.0242 (10)	−0.0003 (7)	0.0070 (7)	−0.0041 (8)

C17—O3	1.208 (2)	C4—H4	0.980
C17—O4	1.349 (2)	C15—O5	1.362 (3)
C17—C8	1.512 (3)	C15—H15	0.930
C21—O6	1.213 (2)	O8—H8A	0.820
C21—O2	1.348 (2)	O4'—C17'	1.349 (2)
C21—C22	1.488 (3)	O4'—C12'	1.471 (2)
C10—C1	1.504 (3)	O3'—C17'	1.214 (2)
C10—C9	1.546 (3)	O2'—C21'	1.356 (2)
C10—C5	1.582 (2)	O1'—C1'	1.202 (2)
C10—H10	0.980	O8'—C18'	1.334 (2)
C2—O2	1.440 (2)	O8'—H8'	0.820
C2—C1	1.523 (3)	O6'—C21'	1.204 (2)
C2—C3	1.525 (3)	O7'—C18'	1.205 (2)
C2—H2	0.980	O5'—C15'	1.366 (2)
C13—C16	1.345 (3)	O5'—C16'	1.370 (2)
C13—C14	1.431 (3)	C17'—C8'	1.506 (2)
C13—C12	1.495 (3)	C9'—C11'	1.532 (2)
C3—C4	1.536 (3)	C9'—C20'	1.539 (2)
C3—H3A	0.970	C9'—C8'	1.543 (2)
C3—H3B	0.970	C9'—C10'	1.549 (2)
C2'—O2'	1.434 (2)	C3'—C4'	1.536 (2)
C2'—C1'	1.517 (3)	C3'—H3'1	0.970
C2'—C3'	1.526 (2)	C3'—H3'2	0.970
C2'—H2'	0.980	C21'—C22'	1.497 (3)
C7—C6	1.527 (3)	C1'—C10'	1.522 (2)
C7—C8	1.527 (3)	C13'—C16'	1.351 (3)
C7—H7A	0.970	C13'—C14'	1.434 (3)
C7—H7B	0.970	C13'—C12'	1.495 (3)
C1—O1	1.206 (2)	C16'—H16'	0.930
C14—C15	1.337 (3)	C14'—C15'	1.340 (3)
C14—H14	0.930	C14'—H14'	0.930
C6—C5	1.539 (2)	C12'—C11'	1.520 (2)
C6—H6A	0.970	C12'—H12'	0.980
C6—H6B	0.970	C4'—C18'	1.527 (2)
C20—C9	1.543 (2)	C4'—C5'	1.561 (3)
C20—H20A	0.960	C4'—H4'	0.980
C20—H20B	0.960	C11'—H11C	0.970
C20—H20C	0.960	C11'—H11D	0.970
C12—O4	1.471 (2)	C5'—C6'	1.545 (2)
C12—C11	1.513 (3)	C5'—C19'	1.550 (2)
C12—H12	0.980	C5'—C10'	1.572 (2)
C5—C19	1.544 (2)	C15'—H15'	0.930
C5—C4	1.567 (3)	C6'—C7'	1.528 (3)
C8—C9	1.541 (2)	C6'—H6'1	0.970
C8—H8	0.980	C6'—H6'2	0.970
C22—H22A	0.960	C10'—H10'	0.980
C22—H22B	0.960	C22'—H22D	0.960
C22—H22C	0.960	C22'—H22E	0.960
C9—C11	1.546 (2)	C22'—H22F	0.960
C16—O5	1.366 (3)	C8'—C7'	1.525 (2)
C16—H16	0.930	C8'—H8'1	0.980
C11—H11A	0.970	C19'—H19D	0.960
C11—H11B	0.970	C19'—H19E	0.960
C18—O7	1.200 (2)	C19'—H19F	0.960
C18—O8	1.335 (2)	C7'—H7'1	0.970
C18—C4	1.527 (3)	C7'—H7'2	0.970
C19—H19A	0.960	C20'—H20D	0.960
C19—H19B	0.960	C20'—H20E	0.960
C19—H19C	0.960	C20'—H20F	0.960
O3—C17—O4	117.51 (17)	C14—C15—H15	124.6
O3—C17—C8	123.97 (17)	O5—C15—H15	124.6
O4—C17—C8	118.25 (15)	C21—O2—C2	114.88 (14)
O6—C21—O2	121.98 (16)	C17—O4—C12	122.60 (14)
O6—C21—C22	126.11 (17)	C18—O8—H8A	109.5
O2—C21—C22	111.91 (16)	C15—O5—C16	105.86 (16)
C1—C10—C9	115.10 (15)	C17'—O4'—C12'	122.14 (14)
C1—C10—C5	108.90 (14)	C21'—O2'—C2'	114.68 (14)
C9—C10—C5	117.10 (15)	C18'—O8'—H8'	109.5
C1—C10—H10	104.8	C15'—O5'—C16'	106.00 (14)
C9—C10—H10	104.8	O3'—C17'—O4'	117.37 (16)
C5—C10—H10	104.8	O3'—C17'—C8'	124.00 (16)
O2—C2—C1	110.60 (14)	O4'—C17'—C8'	118.44 (15)
O2—C2—C3	107.88 (15)	C11'—C9'—C20'	109.58 (14)
C1—C2—C3	110.20 (15)	C11'—C9'—C8'	105.19 (14)
O2—C2—H2	109.4	C20'—C9'—C8'	111.58 (14)
C1—C2—H2	109.4	C11'—C9'—C10'	108.80 (14)
C3—C2—H2	109.4	C20'—C9'—C10'	115.87 (14)
C16—C13—C14	105.66 (17)	C8'—C9'—C10'	105.21 (14)
C16—C13—C12	128.21 (18)	C2'—C3'—C4'	108.73 (14)
C14—C13—C12	126.05 (17)	C2'—C3'—H3'1	109.9
C2—C3—C4	109.27 (15)	C4'—C3'—H3'1	109.9
C2—C3—H3A	109.8	C2'—C3'—H3'2	109.9
C4—C3—H3A	109.8	C4'—C3'—H3'2	109.9
C2—C3—H3B	109.8	H3'1—C3'—H3'2	108.3
C4—C3—H3B	109.8	O6'—C21'—O2'	123.28 (17)
H3A—C3—H3B	108.3	O6'—C21'—C22'	126.00 (17)
O2'—C2'—C1'	111.40 (14)	O2'—C21'—C22'	110.72 (16)
O2'—C2'—C3'	108.58 (14)	O1'—C1'—C2'	122.59 (16)
C1'—C2'—C3'	108.88 (15)	O1'—C1'—C10'	125.18 (16)
O2'—C2'—H2'	109.3	C2'—C1'—C10'	112.22 (14)
C1'—C2'—H2'	109.3	C16'—C13'—C14'	105.75 (16)
C3'—C2'—H2'	109.3	C16'—C13'—C12'	128.77 (17)
C6—C7—C8	109.98 (15)	C14'—C13'—C12'	125.13 (16)
C6—C7—H7A	109.7	C13'—C16'—O5'	110.76 (16)
C8—C7—H7A	109.7	C13'—C16'—H16'	124.6
C6—C7—H7B	109.7	O5'—C16'—H16'	124.6
C8—C7—H7B	109.7	C15'—C14'—C13'	106.67 (17)
H7A—C7—H7B	108.2	C15'—C14'—H14'	126.7
O1—C1—C10	125.78 (17)	C13'—C14'—H14'	126.7
O1—C1—C2	122.15 (17)	O4'—C12'—C13'	107.57 (14)
C10—C1—C2	112.04 (15)	O4'—C12'—C11'	113.40 (14)
C15—C14—C13	106.63 (18)	C13'—C12'—C11'	111.01 (15)
C15—C14—H14	126.7	O4'—C12'—H12'	108.2
C13—C14—H14	126.7	C13'—C12'—H12'	108.2
C7—C6—C5	113.95 (15)	C11'—C12'—H12'	108.2
C7—C6—H6A	108.8	C18'—C4'—C3'	111.86 (14)
C5—C6—H6A	108.8	C18'—C4'—C5'	111.53 (15)
C7—C6—H6B	108.8	C3'—C4'—C5'	113.38 (14)
C5—C6—H6B	108.8	C18'—C4'—H4'	106.5
H6A—C6—H6B	107.7	C3'—C4'—H4'	106.5
C9—C20—H20A	109.5	C5'—C4'—H4'	106.5
C9—C20—H20B	109.5	C12'—C11'—C9'	112.55 (14)
H20A—C20—H20B	109.5	C12'—C11'—H11C	109.1
C9—C20—H20C	109.5	C9'—C11'—H11C	109.1
H20A—C20—H20C	109.5	C12'—C11'—H11D	109.1
H20B—C20—H20C	109.5	C9'—C11'—H11D	109.1
O4—C12—C13	105.53 (14)	H11C—C11'—H11D	107.8
O4—C12—C11	113.56 (14)	C6'—C5'—C19'	110.49 (15)
C13—C12—C11	115.33 (15)	C6'—C5'—C4'	109.82 (14)
O4—C12—H12	107.3	C19'—C5'—C4'	109.82 (14)
C13—C12—H12	107.3	C6'—C5'—C10'	107.14 (14)
C11—C12—H12	107.3	C19'—C5'—C10'	113.65 (14)
C6—C5—C19	110.08 (14)	C4'—C5'—C10'	105.75 (14)
C6—C5—C4	109.75 (15)	C14'—C15'—O5'	110.82 (17)
C19—C5—C4	109.75 (15)	C14'—C15'—H15'	124.6
C6—C5—C10	108.25 (14)	O5'—C15'—H15'	124.6
C19—C5—C10	113.76 (14)	C7'—C6'—C5'	114.53 (15)
C4—C5—C10	105.10 (14)	C7'—C6'—H6'1	108.6
C17—C8—C7	113.59 (15)	C5'—C6'—H6'1	108.6
C17—C8—C9	112.03 (15)	C7'—C6'—H6'2	108.6
C7—C8—C9	112.36 (15)	C5'—C6'—H6'2	108.6
C17—C8—H8	106.1	H6'1—C6'—H6'2	107.6
C7—C8—H8	106.1	C1'—C10'—C9'	115.14 (14)
C9—C8—H8	106.1	C1'—C10'—C5'	109.95 (14)
C21—C22—H22A	109.5	C9'—C10'—C5'	117.47 (14)
C21—C22—H22B	109.5	C1'—C10'—H10'	104.2
H22A—C22—H22B	109.5	C9'—C10'—H10'	104.2
C21—C22—H22C	109.5	C5'—C10'—H10'	104.2
H22A—C22—H22C	109.5	C21'—C22'—H22D	109.5
H22B—C22—H22C	109.5	C21'—C22'—H22E	109.5
C8—C9—C20	111.05 (14)	H22D—C22'—H22E	109.5
C8—C9—C10	106.71 (14)	C21'—C22'—H22F	109.5
C20—C9—C10	114.89 (14)	H22D—C22'—H22F	109.5
C8—C9—C11	105.14 (14)	H22E—C22'—H22F	109.5
C20—C9—C11	109.83 (15)	C17'—C8'—C7'	113.41 (14)
C10—C9—C11	108.72 (14)	C17'—C8'—C9'	111.80 (14)
C13—C16—O5	110.99 (19)	C7'—C8'—C9'	112.71 (15)
C13—C16—H16	124.5	C17'—C8'—H8'1	106.1
O5—C16—H16	124.5	C7'—C8'—H8'1	106.1
C12—C11—C9	110.38 (15)	C9'—C8'—H8'1	106.1
C12—C11—H11A	109.6	C5'—C19'—H19D	109.5
C9—C11—H11A	109.6	C5'—C19'—H19E	109.5
C12—C11—H11B	109.6	H19D—C19'—H19E	109.5
C9—C11—H11B	109.6	C5'—C19'—H19F	109.5
H11A—C11—H11B	108.1	H19D—C19'—H19F	109.5
O7—C18—O8	123.35 (18)	H19E—C19'—H19F	109.5
O7—C18—C4	122.76 (17)	O7'—C18'—O8'	123.29 (17)
O8—C18—C4	113.89 (16)	O7'—C18'—C4'	123.43 (16)
C5—C19—H19A	109.5	O8'—C18'—C4'	113.26 (15)
C5—C19—H19B	109.5	C8'—C7'—C6'	110.04 (15)
H19A—C19—H19B	109.5	C8'—C7'—H7'1	109.7
C5—C19—H19C	109.5	C6'—C7'—H7'1	109.7
H19A—C19—H19C	109.5	C8'—C7'—H7'2	109.7
H19B—C19—H19C	109.5	C6'—C7'—H7'2	109.7
C18—C4—C3	112.41 (16)	H7'1—C7'—H7'2	108.2
C18—C4—C5	111.84 (15)	C9'—C20'—H20D	109.5
C3—C4—C5	112.27 (15)	C9'—C20'—H20E	109.5
C18—C4—H4	106.6	H20D—C20'—H20E	109.5
C3—C4—H4	106.6	C9'—C20'—H20F	109.5
C5—C4—H4	106.6	H20D—C20'—H20F	109.5
C14—C15—O5	110.86 (18)	H20E—C20'—H20F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O6i	0.82	1.92	2.7264 (18)	168
O8'—H8'···O3'ii	0.82	1.92	2.7308 (17)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O6i	0.82	1.92	2.7264 (18)	168
O8′—H8′⋯O3′ii	0.82	1.92	2.7308 (17)	172

Symmetry code: (i) ; (ii) .