Acanthoic Acid.

THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,4aR,7S,8aS,10aS)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodeca-hydro-phenanthrene-1-carb-oxy-lic acid], C(20)H(30)O(2), is a pimarane-type diterpene extracted from Croton oblongifolius. There are two independent mol-ecules in the asymmetric unit. In both of these, the six-membered rings A, B and C adopt chair, boat and half-chair conformations, respectively. Rings A and B are trans-fused. The two mol-ecules in the asymmetric unit form O-H⋯O hydrogen-bonded R(2) (2)(8) dimers. The absolute configuration was assigned on the basis of the published literature on analogous structures.

Related literature

For background to the structure of acanthoic acid, see: Kim et al. (1998 ▶); Ling et al. (2001 ▶); Suh et al. (2001 ▶). For the related absolute configuration, see: Ling et al. (2000 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H30O2

M = 302.44

Tetragonal,

a = 12.8697 (16) Å

c = 21.768 (2) Å

V = 3605.5 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.40 × 0.20 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

21616 measured reflections

4824 independent reflections

3830 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.158

S = 1.02

4824 reflections

405 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019483/fj2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019483/fj2300Isup2.hkl

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

C20H30O2	Dx = 1.114 Mg m−3
Mr = 302.44	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 9639 reflections
Hall symbol: P 4cw	θ = 1.6–30.2°
a = 12.8697 (16) Å	µ = 0.07 mm−1
c = 21.768 (2) Å	T = 100 K
V = 3605.5 (7) Å3	Needle, colourless
Z = 8	0.40 × 0.20 × 0.02 mm
F(000) = 1328

Bruker SMART APEXII CCD area-detector diffractometer	3830 reflections with I > 2σ(I)
Radiation source: Mo	Rint = 0.050
graphite	θmax = 30.2°, θmin = 1.6°
φ and ω scans	h = −16→16
21616 measured reflections	k = −17→17
4824 independent reflections	l = −25→28

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0853P)2 + 1.0669P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.158	(Δ/σ)max = 0.002
S = 1.02	Δρmax = 0.37 e Å−3
4824 reflections	Δρmin = −0.29 e Å−3
405 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.2020 (3)	0.6538 (3)	0.07071 (16)	0.0369 (7)
H1A	0.133	0.6753	0.0833	0.044*
H1B	0.208	0.6659	0.0269	0.044*
C2	0.2143 (3)	0.5365 (3)	0.08320 (18)	0.0395 (8)
H2A	0.1582	0.4991	0.0633	0.047*
H2B	0.2793	0.5125	0.0657	0.047*
C3	0.2130 (3)	0.5131 (3)	0.15123 (18)	0.0389 (7)
H3A	0.2246	0.4393	0.157	0.047*
H3B	0.1446	0.5293	0.1673	0.047*
C4	0.2946 (2)	0.5735 (2)	0.18865 (14)	0.0283 (6)
C5	0.2819 (2)	0.6927 (2)	0.17370 (13)	0.0257 (6)
H5	0.2117	0.7103	0.1876	0.031*
C6	0.3540 (2)	0.7641 (2)	0.21113 (15)	0.0332 (6)
H6A	0.4256	0.7438	0.2041	0.04*
H6B	0.3393	0.7553	0.2545	0.04*
C7	0.3407 (3)	0.8792 (3)	0.19396 (17)	0.0384 (7)
H7A	0.3387	0.9204	0.2313	0.046*
H7B	0.4005	0.9015	0.1703	0.046*
C8	0.2417 (2)	0.9002 (2)	0.15664 (15)	0.0309 (6)
H8	0.182	0.8755	0.1805	0.037*
C9	0.2483 (2)	0.8366 (2)	0.09816 (14)	0.0307 (6)
C10	0.2833 (2)	0.7217 (2)	0.10447 (13)	0.0261 (6)
C11	0.2242 (3)	0.8779 (3)	0.04395 (17)	0.0439 (8)
H11	0.2322	0.8361	0.0094	0.053*
C12	0.1851 (4)	0.9870 (3)	0.03404 (18)	0.0535 (10)
H12A	0.1287	0.9856	0.0045	0.064*
H12B	0.2406	1.0289	0.0169	0.064*
C13	0.1463 (3)	1.0377 (3)	0.09429 (18)	0.0481 (9)
C14	0.2265 (3)	1.0152 (3)	0.14356 (18)	0.0436 (8)
H14A	0.2055	1.0496	0.1812	0.052*
H14B	0.2925	1.0447	0.131	0.052*
C15	0.1282 (5)	1.1516 (4)	0.0829 (2)	0.0853 (19)
H15	0.0933	1.1636	0.0461	0.102*
C16	0.1472 (8)	1.2286 (4)	0.1089 (3)	0.123 (3)
H16A	0.182	1.2263	0.1463	0.147*
H16B	0.1275	1.2921	0.0922	0.147*
C17	0.0409 (3)	0.9895 (4)	0.1120 (2)	0.0610 (12)
H17A	0.0484	0.9156	0.1159	0.092*
H17B	−0.0093	1.0047	0.0806	0.092*
H17C	0.018	1.0181	0.1504	0.092*
C18	0.2726 (3)	0.5543 (3)	0.25738 (17)	0.0429 (8)
H18A	0.2051	0.5811	0.2676	0.064*
H18B	0.3243	0.5888	0.2817	0.064*
H18C	0.2745	0.481	0.2656	0.064*
C19	0.4032 (2)	0.5295 (2)	0.17572 (14)	0.0312 (6)
C20	0.3915 (2)	0.7082 (2)	0.07483 (14)	0.0332 (7)
H20A	0.3909	0.7371	0.0342	0.05*
H20B	0.4083	0.6356	0.0726	0.05*
H20C	0.4427	0.7434	0.0993	0.05*
O1	0.42045 (17)	0.46242 (17)	0.13726 (11)	0.0352 (5)
O2	0.47604 (18)	0.5668 (2)	0.21170 (12)	0.0437 (6)
H2	0.532	0.5404	0.2027	0.066*
C1'	0.8991 (3)	0.6408 (3)	0.09529 (17)	0.0415 (8)
H1'1	0.9703	0.6216	0.086	0.05*
H1'2	0.8959	0.716	0.0969	0.05*
C2'	0.8713 (3)	0.5981 (3)	0.15830 (16)	0.0468 (9)
H2'1	0.9222	0.6216	0.1881	0.056*
H2'2	0.8039	0.6248	0.1706	0.056*
C3'	0.8682 (3)	0.4805 (3)	0.15808 (16)	0.0429 (8)
H3'1	0.8463	0.4564	0.1983	0.051*
H3'2	0.9377	0.4542	0.1507	0.051*
C4'	0.7945 (2)	0.4360 (2)	0.10933 (15)	0.0322 (6)
C5'	0.8256 (2)	0.4816 (2)	0.04527 (14)	0.0271 (6)
H5'	0.8981	0.4603	0.0397	0.033*
C6'	0.7679 (2)	0.4328 (2)	−0.00971 (15)	0.0316 (6)
H6'1	0.7876	0.3603	−0.0131	0.038*
H6'2	0.6937	0.4357	−0.0021	0.038*
C7'	0.7919 (2)	0.4880 (2)	−0.07080 (14)	0.0299 (6)
H7'1	0.7984	0.4365	−0.1031	0.036*
H7'2	0.7342	0.5333	−0.0813	0.036*
C8'	0.8922 (2)	0.5526 (2)	−0.06797 (13)	0.0257 (6)
H8'	0.9494	0.5068	−0.0557	0.031*
C9'	0.8790 (2)	0.6354 (2)	−0.01921 (15)	0.0301 (6)
C10'	0.8288 (2)	0.6029 (2)	0.04225 (14)	0.0285 (6)
C11'	0.9096 (3)	0.7328 (2)	−0.02861 (17)	0.0402 (8)
H11'	0.8987	0.7801	0.003	0.048*
C12'	0.9605 (3)	0.7729 (3)	−0.08629 (19)	0.0435 (8)
H12C	1.018	0.8177	−0.0751	0.052*
H12D	0.9106	0.8144	−0.109	0.052*
C13'	1.0012 (2)	0.6844 (3)	−0.12842 (16)	0.0355 (7)
C14'	0.9179 (2)	0.5993 (2)	−0.13061 (14)	0.0332 (6)
H14C	0.8549	0.6283	−0.1481	0.04*
H14D	0.9414	0.5442	−0.1576	0.04*
C15'	1.0229 (3)	0.7320 (3)	−0.1906 (2)	0.0536 (10)
H15'	1.0743	0.7829	−0.1908	0.064*
C16'	0.9827 (4)	0.7138 (5)	−0.2418 (2)	0.0762 (15)
H16C	0.9307	0.664	−0.2453	0.091*
H16D	1.0047	0.7502	−0.2763	0.091*
C17'	1.1037 (2)	0.6415 (3)	−0.10289 (17)	0.0401 (8)
H17D	1.1267	0.5847	−0.128	0.06*
H17E	1.0932	0.6176	−0.0616	0.06*
H17F	1.1553	0.6954	−0.1031	0.06*
C18'	0.8066 (3)	0.3167 (3)	0.10861 (19)	0.0447 (8)
H18D	0.7936	0.2897	0.149	0.067*
H18E	0.876	0.2989	0.0963	0.067*
H18F	0.7579	0.2872	0.0801	0.067*
C19'	0.6819 (2)	0.4561 (2)	0.12987 (15)	0.0318 (6)
C20'	0.7191 (2)	0.6510 (2)	0.04652 (16)	0.0338 (7)
H20D	0.723	0.7242	0.0383	0.051*
H20E	0.6916	0.6401	0.087	0.051*
H20F	0.6743	0.6185	0.0169	0.051*
O1'	0.66053 (17)	0.4932 (2)	0.17988 (11)	0.0402 (5)
O2'	0.61042 (16)	0.42401 (18)	0.09132 (11)	0.0362 (5)
H2'	0.5527	0.4336	0.1063	0.054*

	U11	U22	U33	U12	U13	U23
C1	0.0352 (16)	0.0399 (17)	0.0356 (17)	0.0035 (13)	−0.0104 (13)	−0.0085 (13)
C2	0.0300 (15)	0.0364 (17)	0.052 (2)	−0.0012 (13)	−0.0083 (14)	−0.0164 (15)
C3	0.0293 (15)	0.0311 (15)	0.056 (2)	−0.0040 (12)	0.0048 (14)	−0.0024 (15)
C4	0.0268 (13)	0.0308 (14)	0.0273 (14)	0.0015 (11)	0.0060 (11)	0.0024 (11)
C5	0.0238 (12)	0.0294 (14)	0.0241 (14)	0.0008 (10)	0.0007 (10)	−0.0004 (11)
C6	0.0321 (15)	0.0382 (16)	0.0292 (15)	−0.0013 (12)	−0.0035 (12)	−0.0085 (13)
C7	0.0365 (16)	0.0379 (17)	0.0408 (19)	−0.0064 (13)	−0.0014 (14)	−0.0107 (14)
C8	0.0306 (14)	0.0302 (14)	0.0320 (15)	−0.0015 (11)	0.0090 (12)	−0.0022 (12)
C9	0.0304 (14)	0.0284 (14)	0.0333 (16)	0.0010 (11)	0.0095 (12)	0.0000 (12)
C10	0.0267 (13)	0.0283 (13)	0.0232 (14)	0.0010 (10)	0.0013 (10)	−0.0035 (11)
C11	0.056 (2)	0.0450 (19)	0.0308 (17)	0.0130 (16)	0.0074 (15)	0.0021 (14)
C12	0.070 (3)	0.050 (2)	0.041 (2)	0.0220 (19)	0.0139 (18)	0.0119 (17)
C13	0.064 (2)	0.0360 (17)	0.044 (2)	0.0177 (16)	0.0181 (18)	0.0112 (15)
C14	0.054 (2)	0.0311 (16)	0.046 (2)	0.0001 (14)	0.0140 (16)	−0.0039 (14)
C15	0.152 (5)	0.046 (3)	0.057 (3)	0.037 (3)	0.043 (3)	0.019 (2)
C16	0.259 (10)	0.047 (3)	0.063 (4)	0.002 (4)	0.052 (5)	0.001 (3)
C17	0.049 (2)	0.066 (3)	0.068 (3)	0.019 (2)	0.007 (2)	0.017 (2)
C18	0.0443 (19)	0.0463 (19)	0.0381 (19)	0.0087 (15)	0.0151 (15)	0.0136 (15)
C19	0.0302 (14)	0.0334 (15)	0.0301 (16)	0.0031 (12)	0.0049 (12)	0.0063 (12)
C20	0.0337 (15)	0.0368 (16)	0.0290 (16)	0.0009 (12)	0.0090 (12)	−0.0002 (12)
O1	0.0297 (11)	0.0339 (11)	0.0420 (13)	0.0043 (9)	0.0057 (9)	−0.0020 (9)
O2	0.0306 (11)	0.0593 (16)	0.0413 (14)	0.0109 (11)	−0.0038 (10)	−0.0125 (12)
C1'	0.0365 (17)	0.0484 (19)	0.0395 (18)	−0.0164 (14)	0.0051 (14)	−0.0145 (15)
C2'	0.0376 (18)	0.070 (2)	0.0332 (18)	−0.0149 (17)	0.0003 (14)	−0.0156 (17)
C3'	0.0282 (15)	0.070 (2)	0.0309 (17)	−0.0012 (15)	0.0022 (13)	−0.0002 (16)
C4'	0.0258 (14)	0.0394 (16)	0.0312 (16)	0.0013 (12)	0.0038 (12)	0.0000 (12)
C5'	0.0217 (12)	0.0287 (13)	0.0309 (15)	−0.0003 (10)	0.0043 (11)	−0.0007 (11)
C6'	0.0336 (15)	0.0293 (14)	0.0319 (16)	−0.0072 (12)	0.0048 (12)	−0.0071 (12)
C7'	0.0295 (14)	0.0318 (14)	0.0284 (15)	−0.0045 (11)	−0.0005 (11)	−0.0061 (12)
C8'	0.0259 (13)	0.0252 (13)	0.0261 (14)	0.0008 (10)	0.0033 (11)	−0.0027 (11)
C9'	0.0251 (13)	0.0291 (14)	0.0363 (16)	−0.0030 (11)	0.0088 (12)	−0.0072 (12)
C10'	0.0255 (13)	0.0261 (13)	0.0337 (16)	−0.0048 (10)	0.0063 (11)	−0.0087 (11)
C11'	0.0442 (18)	0.0266 (15)	0.050 (2)	−0.0019 (13)	0.0177 (15)	−0.0090 (14)
C12'	0.0411 (18)	0.0291 (16)	0.060 (2)	−0.0036 (13)	0.0171 (16)	0.0034 (15)
C13'	0.0319 (15)	0.0380 (16)	0.0366 (17)	−0.0001 (12)	0.0098 (13)	0.0089 (13)
C14'	0.0330 (15)	0.0371 (16)	0.0296 (15)	0.0026 (12)	0.0022 (12)	0.0000 (12)
C15'	0.045 (2)	0.063 (2)	0.053 (3)	0.0037 (17)	0.0147 (18)	0.022 (2)
C16'	0.079 (3)	0.111 (4)	0.039 (3)	0.004 (3)	0.008 (2)	0.013 (2)
C17'	0.0322 (16)	0.0484 (19)	0.0398 (19)	−0.0012 (13)	0.0072 (14)	0.0047 (15)
C18'	0.0447 (19)	0.0415 (18)	0.048 (2)	0.0055 (15)	0.0097 (16)	0.0135 (16)
C19'	0.0259 (14)	0.0368 (16)	0.0328 (16)	−0.0006 (11)	0.0042 (12)	0.0027 (12)
C20'	0.0332 (15)	0.0296 (14)	0.0387 (17)	0.0017 (12)	0.0126 (13)	−0.0055 (13)
O1'	0.0287 (11)	0.0606 (15)	0.0312 (12)	0.0039 (10)	0.0038 (9)	−0.0057 (11)
O2'	0.0251 (10)	0.0459 (13)	0.0374 (12)	−0.0053 (9)	0.0070 (9)	−0.0049 (10)

C1—C2	1.542 (5)	C1'—C2'	1.520 (5)
C1—C10	1.548 (4)	C1'—C10'	1.545 (4)
C1—H1A	0.97	C1'—H1'1	0.97
C1—H1B	0.97	C1'—H1'2	0.97
C2—C3	1.511 (6)	C2'—C3'	1.514 (6)
C2—H2A	0.97	C2'—H2'1	0.97
C2—H2B	0.97	C2'—H2'2	0.97
C3—C4	1.540 (4)	C3'—C4'	1.534 (5)
C3—H3A	0.97	C3'—H3'1	0.97
C3—H3B	0.97	C3'—H3'2	0.97
C4—C19	1.534 (4)	C4'—C19'	1.538 (4)
C4—C18	1.543 (4)	C4'—C18'	1.544 (5)
C4—C5	1.577 (4)	C4'—C5'	1.565 (4)
C5—C6	1.539 (4)	C5'—C6'	1.542 (4)
C5—C10	1.553 (4)	C5'—C10'	1.563 (4)
C5—H5	0.98	C5'—H5'	0.98
C6—C7	1.537 (5)	C6'—C7'	1.539 (4)
C6—H6A	0.97	C6'—H6'1	0.97
C6—H6B	0.97	C6'—H6'2	0.97
C7—C8	1.535 (5)	C7'—C8'	1.536 (4)
C7—H7A	0.97	C7'—H7'1	0.97
C7—H7B	0.97	C7'—H7'2	0.97
C8—C9	1.515 (4)	C8'—C9'	1.514 (4)
C8—C14	1.520 (4)	C8'—C14'	1.526 (4)
C8—H8	0.98	C8'—H8'	0.98
C9—C11	1.331 (5)	C9'—C11'	1.329 (4)
C9—C10	1.552 (4)	C9'—C10'	1.544 (4)
C10—C20	1.545 (4)	C10'—C20'	1.545 (4)
C11—C12	1.507 (5)	C11'—C12'	1.507 (5)
C11—H11	0.93	C11'—H11'	0.93
C12—C13	1.548 (5)	C12'—C13'	1.553 (5)
C12—H12A	0.97	C12'—H12C	0.97
C12—H12B	0.97	C12'—H12D	0.97
C13—C15	1.505 (5)	C13'—C15'	1.511 (5)
C13—C14	1.516 (6)	C13'—C17'	1.534 (5)
C13—C17	1.540 (6)	C13'—C14'	1.534 (5)
C14—H14A	0.97	C14'—H14C	0.97
C14—H14B	0.97	C14'—H14D	0.97
C15—C16	1.167 (8)	C15'—C16'	1.251 (7)
C15—H15	0.93	C15'—H15'	0.93
C16—H16A	0.93	C16'—H16C	0.93
C16—H16B	0.93	C16'—H16D	0.93
C17—H17A	0.96	C17'—H17D	0.96
C17—H17B	0.96	C17'—H17E	0.96
C17—H17C	0.96	C17'—H17F	0.96
C18—H18A	0.96	C18'—H18D	0.96
C18—H18B	0.96	C18'—H18E	0.96
C18—H18C	0.96	C18'—H18F	0.96
C19—O1	1.223 (4)	C19'—O1'	1.220 (4)
C19—O2	1.313 (4)	C19'—O2'	1.312 (4)
C20—H20A	0.96	C20'—H20D	0.96
C20—H20B	0.96	C20'—H20E	0.96
C20—H20C	0.96	C20'—H20F	0.96
O2—H2	0.82	O2'—H2'	0.82
C2—C1—C10	113.6 (3)	C2'—C1'—C10'	115.0 (3)
C2—C1—H1A	108.9	C2'—C1'—H1'1	108.5
C10—C1—H1A	108.9	C10'—C1'—H1'1	108.5
C2—C1—H1B	108.9	C2'—C1'—H1'2	108.5
C10—C1—H1B	108.9	C10'—C1'—H1'2	108.5
H1A—C1—H1B	107.7	H1'1—C1'—H1'2	107.5
C3—C2—C1	111.5 (3)	C3'—C2'—C1'	111.4 (3)
C3—C2—H2A	109.3	C3'—C2'—H2'1	109.4
C1—C2—H2A	109.3	C1'—C2'—H2'1	109.4
C3—C2—H2B	109.3	C3'—C2'—H2'2	109.4
C1—C2—H2B	109.3	C1'—C2'—H2'2	109.4
H2A—C2—H2B	108	H2'1—C2'—H2'2	108
C2—C3—C4	114.2 (3)	C2'—C3'—C4'	113.1 (3)
C2—C3—H3A	108.7	C2'—C3'—H3'1	109
C4—C3—H3A	108.7	C4'—C3'—H3'1	109
C2—C3—H3B	108.7	C2'—C3'—H3'2	109
C4—C3—H3B	108.7	C4'—C3'—H3'2	109
H3A—C3—H3B	107.6	H3'1—C3'—H3'2	107.8
C19—C4—C3	109.8 (3)	C3'—C4'—C19'	108.6 (3)
C19—C4—C18	106.6 (2)	C3'—C4'—C18'	108.4 (3)
C3—C4—C18	107.9 (3)	C19'—C4'—C18'	105.4 (3)
C19—C4—C5	114.6 (2)	C3'—C4'—C5'	108.6 (2)
C3—C4—C5	108.1 (2)	C19'—C4'—C5'	115.9 (3)
C18—C4—C5	109.7 (2)	C18'—C4'—C5'	109.8 (3)
C6—C5—C10	111.3 (2)	C6'—C5'—C10'	112.8 (2)
C6—C5—C4	114.2 (2)	C6'—C5'—C4'	114.6 (2)
C10—C5—C4	115.6 (2)	C10'—C5'—C4'	114.8 (2)
C6—C5—H5	104.8	C6'—C5'—H5'	104.4
C10—C5—H5	104.8	C10'—C5'—H5'	104.4
C4—C5—H5	104.8	C4'—C5'—H5'	104.4
C5—C6—C7	112.3 (2)	C7'—C6'—C5'	112.7 (2)
C5—C6—H6A	109.1	C7'—C6'—H6'1	109
C7—C6—H6A	109.1	C5'—C6'—H6'1	109
C5—C6—H6B	109.1	C7'—C6'—H6'2	109
C7—C6—H6B	109.1	C5'—C6'—H6'2	109
H6A—C6—H6B	107.9	H6'1—C6'—H6'2	107.8
C8—C7—C6	113.0 (2)	C8'—C7'—C6'	112.5 (2)
C8—C7—H7A	109	C8'—C7'—H7'1	109.1
C6—C7—H7A	109	C6'—C7'—H7'1	109.1
C8—C7—H7B	109	C8'—C7'—H7'2	109.1
C6—C7—H7B	109	C6'—C7'—H7'2	109.1
H7A—C7—H7B	107.8	H7'1—C7'—H7'2	107.8
C9—C8—C14	112.0 (3)	C9'—C8'—C14'	111.9 (2)
C9—C8—C7	107.7 (3)	C9'—C8'—C7'	108.4 (2)
C14—C8—C7	112.1 (3)	C14'—C8'—C7'	111.1 (2)
C9—C8—H8	108.3	C9'—C8'—H8'	108.5
C14—C8—H8	108.3	C14'—C8'—H8'	108.5
C7—C8—H8	108.3	C7'—C8'—H8'	108.5
C11—C9—C8	121.1 (3)	C11'—C9'—C8'	121.5 (3)
C11—C9—C10	121.8 (3)	C11'—C9'—C10'	120.9 (3)
C8—C9—C10	117.1 (3)	C8'—C9'—C10'	117.6 (2)
C20—C10—C1	110.3 (3)	C20'—C10'—C9'	109.0 (3)
C20—C10—C9	109.4 (2)	C20'—C10'—C1'	111.3 (2)
C1—C10—C9	107.5 (2)	C9'—C10'—C1'	108.5 (2)
C20—C10—C5	112.8 (2)	C20'—C10'—C5'	111.9 (2)
C1—C10—C5	108.5 (2)	C9'—C10'—C5'	108.6 (2)
C9—C10—C5	108.1 (2)	C1'—C10'—C5'	107.4 (3)
C9—C11—C12	125.2 (3)	C9'—C11'—C12'	125.5 (3)
C9—C11—H11	117.4	C9'—C11'—H11'	117.3
C12—C11—H11	117.4	C12'—C11'—H11'	117.3
C11—C12—C13	112.3 (3)	C11'—C12'—C13'	112.8 (3)
C11—C12—H12A	109.1	C11'—C12'—H12C	109
C13—C12—H12A	109.1	C13'—C12'—H12C	109
C11—C12—H12B	109.1	C11'—C12'—H12D	109
C13—C12—H12B	109.1	C13'—C12'—H12D	109
H12A—C12—H12B	107.9	H12C—C12'—H12D	107.8
C15—C13—C14	114.1 (4)	C15'—C13'—C17'	108.1 (3)
C15—C13—C17	107.3 (4)	C15'—C13'—C14'	113.0 (3)
C14—C13—C17	110.2 (3)	C17'—C13'—C14'	110.8 (3)
C15—C13—C12	108.7 (3)	C15'—C13'—C12'	107.1 (3)
C14—C13—C12	107.4 (3)	C17'—C13'—C12'	109.9 (3)
C17—C13—C12	109.0 (4)	C14'—C13'—C12'	107.8 (3)
C13—C14—C8	114.0 (3)	C8'—C14'—C13'	113.9 (3)
C13—C14—H14A	108.8	C8'—C14'—H14C	108.8
C8—C14—H14A	108.8	C13'—C14'—H14C	108.8
C13—C14—H14B	108.8	C8'—C14'—H14D	108.8
C8—C14—H14B	108.8	C13'—C14'—H14D	108.8
H14A—C14—H14B	107.7	H14C—C14'—H14D	107.7
C16—C15—C13	135.5 (7)	C16'—C15'—C13'	130.2 (4)
C16—C15—H15	112.2	C16'—C15'—H15'	114.9
C13—C15—H15	112.2	C13'—C15'—H15'	114.9
C15—C16—H16A	120	C15'—C16'—H16C	120
C15—C16—H16B	120	C15'—C16'—H16D	120
H16A—C16—H16B	120	H16C—C16'—H16D	120
C13—C17—H17A	109.5	C13'—C17'—H17D	109.5
C13—C17—H17B	109.5	C13'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
C13—C17—H17C	109.5	C13'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5
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
O1—C19—O2	122.5 (3)	O1'—C19'—O2'	122.4 (3)
O1—C19—C4	123.5 (3)	O1'—C19'—C4'	122.5 (3)
O2—C19—C4	114.0 (3)	O2'—C19'—C4'	114.9 (3)
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
C19—O2—H2	109.5	C19'—O2'—H2'	109.5
C10—C1—C2—C3	54.8 (4)	C10'—C1'—C2'—C3'	54.7 (4)
C1—C2—C3—C4	−55.4 (4)	C1'—C2'—C3'—C4'	−55.4 (4)
C2—C3—C4—C19	−72.7 (3)	C2'—C3'—C4'—C19'	−72.1 (3)
C2—C3—C4—C18	171.5 (3)	C2'—C3'—C4'—C18'	173.9 (3)
C2—C3—C4—C5	52.9 (3)	C2'—C3'—C4'—C5'	54.7 (3)
C19—C4—C5—C6	−61.0 (3)	C3'—C4'—C5'—C6'	172.2 (3)
C3—C4—C5—C6	176.2 (3)	C19'—C4'—C5'—C6'	−65.4 (3)
C18—C4—C5—C6	58.8 (3)	C18'—C4'—C5'—C6'	53.8 (3)
C19—C4—C5—C10	70.1 (3)	C3'—C4'—C5'—C10'	−55.0 (3)
C3—C4—C5—C10	−52.7 (3)	C19'—C4'—C5'—C10'	67.5 (3)
C18—C4—C5—C10	−170.1 (3)	C18'—C4'—C5'—C10'	−173.3 (3)
C10—C5—C6—C7	45.5 (3)	C10'—C5'—C6'—C7'	39.9 (3)
C4—C5—C6—C7	178.7 (2)	C4'—C5'—C6'—C7'	173.7 (2)
C5—C6—C7—C8	14.7 (4)	C5'—C6'—C7'—C8'	19.4 (4)
C6—C7—C8—C9	−59.8 (3)	C6'—C7'—C8'—C9'	−61.1 (3)
C6—C7—C8—C14	176.4 (3)	C6'—C7'—C8'—C14'	175.6 (2)
C14—C8—C9—C11	−11.1 (4)	C14'—C8'—C9'—C11'	−13.8 (4)
C7—C8—C9—C11	−134.9 (3)	C7'—C8'—C9'—C11'	−136.6 (3)
C14—C8—C9—C10	169.4 (3)	C14'—C8'—C9'—C10'	166.3 (3)
C7—C8—C9—C10	45.6 (3)	C7'—C8'—C9'—C10'	43.5 (3)
C2—C1—C10—C20	71.9 (4)	C11'—C9'—C10'—C20'	71.0 (4)
C2—C1—C10—C9	−169.0 (3)	C8'—C9'—C10'—C20'	−109.2 (3)
C2—C1—C10—C5	−52.2 (3)	C11'—C9'—C10'—C1'	−50.4 (4)
C11—C9—C10—C20	68.8 (4)	C8'—C9'—C10'—C1'	129.4 (3)
C8—C9—C10—C20	−111.7 (3)	C11'—C9'—C10'—C5'	−166.9 (3)
C11—C9—C10—C1	−51.0 (4)	C8'—C9'—C10'—C5'	13.0 (3)
C8—C9—C10—C1	128.5 (3)	C2'—C1'—C10'—C20'	70.8 (4)
C11—C9—C10—C5	−168.0 (3)	C2'—C1'—C10'—C9'	−169.3 (3)
C8—C9—C10—C5	11.6 (3)	C2'—C1'—C10'—C5'	−52.1 (4)
C6—C5—C10—C20	62.5 (3)	C6'—C5'—C10'—C20'	64.1 (3)
C4—C5—C10—C20	−70.0 (3)	C4'—C5'—C10'—C20'	−69.6 (3)
C6—C5—C10—C1	−174.9 (2)	C6'—C5'—C10'—C9'	−56.3 (3)
C4—C5—C10—C1	52.6 (3)	C4'—C5'—C10'—C9'	170.0 (2)
C6—C5—C10—C9	−58.7 (3)	C6'—C5'—C10'—C1'	−173.5 (2)
C4—C5—C10—C9	168.9 (2)	C4'—C5'—C10'—C1'	52.8 (3)
C8—C9—C11—C12	−2.4 (6)	C8'—C9'—C11'—C12'	−0.6 (6)
C10—C9—C11—C12	177.1 (3)	C10'—C9'—C11'—C12'	179.2 (3)
C9—C11—C12—C13	−16.0 (6)	C9'—C11'—C12'—C13'	−15.2 (5)
C11—C12—C13—C15	169.3 (4)	C11'—C12'—C13'—C15'	165.0 (3)
C11—C12—C13—C14	45.4 (5)	C11'—C12'—C13'—C17'	−77.8 (4)
C11—C12—C13—C17	−74.0 (4)	C11'—C12'—C13'—C14'	43.1 (4)
C15—C13—C14—C8	177.8 (3)	C9'—C8'—C14'—C13'	45.2 (3)
C17—C13—C14—C8	57.1 (4)	C7'—C8'—C14'—C13'	166.5 (3)
C12—C13—C14—C8	−61.6 (4)	C15'—C13'—C14'—C8'	−178.1 (3)
C9—C8—C14—C13	44.4 (4)	C17'—C13'—C14'—C8'	60.3 (4)
C7—C8—C14—C13	165.6 (3)	C12'—C13'—C14'—C8'	−60.0 (4)
C14—C13—C15—C16	−15.6 (10)	C17'—C13'—C15'—C16'	124.4 (5)
C17—C13—C15—C16	106.8 (9)	C14'—C13'—C15'—C16'	1.3 (6)
C12—C13—C15—C16	−135.4 (8)	C12'—C13'—C15'—C16'	−117.2 (5)
C3—C4—C19—O1	5.7 (4)	C3'—C4'—C19'—O1'	−6.0 (4)
C18—C4—C19—O1	122.2 (3)	C18'—C4'—C19'—O1'	110.0 (4)
C5—C4—C19—O1	−116.2 (3)	C5'—C4'—C19'—O1'	−128.4 (3)
C3—C4—C19—O2	−171.4 (3)	C3'—C4'—C19'—O2'	178.4 (3)
C18—C4—C19—O2	−54.8 (3)	C18'—C4'—C19'—O2'	−65.6 (3)
C5—C4—C19—O2	66.8 (3)	C5'—C4'—C19'—O2'	55.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2'—H2'···O1	0.82	1.87	2.687 (3)	177
O2—H2···O1'	0.82	1.83	2.649 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2′—H2′⋯O1	0.82	1.87	2.687 (3)	177
O2—H2⋯O1′	0.82	1.83	2.649 (3)	175