(E)-(20S,25S)-20,23-Di­acetyl-5β-furost-22-ene-3β,26-diyl di­acetate

The crystal structure of the title compound, C₃₅H₅₂O₇, obtained by the Lewis-acid-catalysed acetolysis of sarsasapogenin, confirms that the configuration around the double bond of the side chain is E and that of the chiral C atom α to this double bond is S. This geometry is in agreement with NMR data.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C27'

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3710
           Count of symmetry unique reflns         3737
           Completeness (_total/calc)             99.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

(E)-(20S,25S)-20,23-Diacetyl-5β-furost-22-ene-3β,26-diyl diacetate

Crystal data

C35H52O7	Z = 1
Mr = 584.77	F(000) = 318
Triclinic, P1	Dx = 1.189 Mg m^−3
Hall symbol: P 1	Melting point: 436 K
a = 7.6789 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2222 (11) Å	Cell parameters from 65 reflections
c = 11.3519 (13) Å	θ = 4.7–13.4°
α = 102.368 (9)°	µ = 0.08 mm^−1
β = 103.812 (10)°	T = 296 K
γ = 101.113 (9)°	Plate, colorless
V = 816.81 (16) Å^3	0.60 × 0.60 × 0.20 mm

Data collection

Bruker P4 diffractometer	Rint = 0.037
Radiation source: fine-focus sealed tube, FN4	θmax = 27.5°, θmin = 1.9°
Graphite monochromator	h = −9→3
2θ/ω scans	k = −12→12
5573 measured reflections	l = −14→14
3710 independent reflections	3 standard reflections every 97 reflections
3430 reflections with I > 2σ(I)	intensity decay: 10.1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.078P)^2 + 0.0696P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.17 e Å^−3
3710 reflections	Δρmin = −0.17 e Å^−3
388 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.022 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: see text
Secondary atom site location: difference Fourier map

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4839 (3)	−0.1690 (2)	0.3700 (2)	0.0438 (5)
H1A	0.4167	−0.2377	0.2904	0.053*
H1B	0.6005	−0.1216	0.3614	0.053*
C2	0.5254 (3)	−0.2435 (2)	0.4725 (2)	0.0477 (5)
H2A	0.5945	−0.3097	0.4489	0.057*
H2B	0.6019	−0.1765	0.5509	0.057*
C3	0.3492 (3)	−0.3184 (2)	0.4923 (2)	0.0476 (5)
H3A	0.3806	−0.3553	0.5653	0.057*
O3'	0.2594 (2)	−0.43366 (18)	0.37763 (18)	0.0522 (4)
C4	0.2223 (3)	−0.2235 (3)	0.5126 (2)	0.0472 (5)
H4A	0.2760	−0.1590	0.5959	0.057*
H4B	0.1037	−0.2793	0.5108	0.057*
C4'	0.1424 (4)	−0.5444 (3)	0.3860 (3)	0.0615 (7)
C5	0.1880 (3)	−0.1403 (2)	0.4151 (2)	0.0418 (5)
H5A	0.1138	−0.2063	0.3342	0.050*
C5'	0.0779 (5)	−0.6566 (4)	0.2661 (5)	0.0850 (11)
H5B	0.0262	−0.7425	0.2813	0.128*
H5C	0.1809	−0.6653	0.2336	0.128*
H5D	−0.0151	−0.6347	0.2059	0.128*
C6	0.0715 (3)	−0.0398 (3)	0.4528 (3)	0.0502 (5)
H6A	0.0272	−0.0027	0.3828	0.060*
H6B	−0.0358	−0.0905	0.4699	0.060*
O6'	0.0983 (4)	−0.5505 (3)	0.4800 (3)	0.0878 (8)
C7	0.1830 (3)	0.0799 (2)	0.5690 (2)	0.0470 (5)
H7A	0.2129	0.0437	0.6415	0.056*
H7B	0.1073	0.1435	0.5852	0.056*
C8	0.3630 (3)	0.1590 (2)	0.55313 (19)	0.0367 (4)
H8A	0.3319	0.2067	0.4878	0.044*
C9	0.4802 (3)	0.0600 (2)	0.51394 (18)	0.0350 (4)
H9A	0.5140	0.0184	0.5836	0.042*
C10	0.3695 (3)	−0.0623 (2)	0.39527 (19)	0.0378 (4)
C11	0.6638 (3)	0.1422 (2)	0.5033 (2)	0.0433 (5)
H11A	0.7375	0.0785	0.4826	0.052*
H11B	0.6364	0.1848	0.4348	0.052*
C12	0.7785 (3)	0.2556 (2)	0.6248 (2)	0.0409 (4)
H12A	0.8202	0.2127	0.6911	0.049*
H12B	0.8874	0.3078	0.6104	0.049*
C13	0.6648 (3)	0.3546 (2)	0.66750 (18)	0.0343 (4)
C14	0.4822 (3)	0.2663 (2)	0.67601 (19)	0.0358 (4)
H14A	0.5201	0.2131	0.7355	0.043*
C15	0.3987 (3)	0.3743 (2)	0.7445 (2)	0.0461 (5)
H15A	0.3366	0.4204	0.6873	0.055*
H15B	0.3118	0.3321	0.7836	0.055*
C16	0.5712 (3)	0.4750 (2)	0.8438 (2)	0.0463 (5)
H16A	0.5749	0.4645	0.9281	0.056*
C17	0.7442 (3)	0.4436 (2)	0.80740 (19)	0.0401 (4)
H17A	0.7948	0.3861	0.8586	0.048*
C18	0.6251 (3)	0.4419 (2)	0.5736 (2)	0.0429 (5)
H18A	0.7331	0.4685	0.5470	0.064*
H18B	0.5945	0.5234	0.6139	0.064*
H18C	0.5228	0.3880	0.5016	0.064*
C19	0.3198 (4)	−0.0111 (3)	0.2769 (2)	0.0537 (6)
H19A	0.2487	−0.0882	0.2058	0.081*
H19B	0.4316	0.0318	0.2613	0.081*
H19C	0.2481	0.0551	0.2895	0.081*
C20	0.8846 (3)	0.5896 (2)	0.8502 (2)	0.0425 (5)
C21	1.0144 (3)	0.6067 (3)	0.7668 (3)	0.0561 (6)
H21A	1.1286	0.6740	0.8156	0.084*
H21B	0.9557	0.6373	0.6968	0.084*
H21C	1.0397	0.5194	0.7360	0.084*
C21'	0.9919 (4)	0.6031 (3)	0.9881 (2)	0.0559 (6)
O21'	0.9208 (4)	0.6302 (3)	1.07141 (19)	0.0775 (6)
C22	0.7568 (3)	0.6875 (2)	0.8545 (2)	0.0412 (4)
C22'	1.1793 (5)	0.5723 (4)	1.0153 (4)	0.0832 (11)
H22A	1.2123	0.5589	1.0981	0.125*
H22B	1.2703	0.6486	1.0110	0.125*
H22C	1.1747	0.4898	0.9540	0.125*
O22'	0.5809 (2)	0.61671 (17)	0.84133 (18)	0.0524 (4)
C23	0.7936 (3)	0.8244 (2)	0.8688 (2)	0.0420 (5)
C23'	0.9855 (3)	0.9063 (3)	0.8902 (2)	0.0466 (5)
C23"	1.0106 (5)	1.0291 (4)	0.8365 (4)	0.0743 (9)
H23A	1.1405	1.0722	0.8562	0.111*
H23B	0.9504	1.0947	0.8724	0.111*
H23C	0.9567	0.9986	0.7466	0.111*
O23"	1.1210 (3)	0.8772 (2)	0.9485 (2)	0.0619 (5)
C24	0.6455 (3)	0.9033 (2)	0.8733 (2)	0.0451 (5)
H24A	0.5269	0.8381	0.8572	0.054*
H24B	0.6347	0.9506	0.8074	0.054*
C25	0.6911 (3)	1.0106 (2)	1.0024 (2)	0.0439 (5)
H25A	0.8125	1.0739	1.0177	0.053*
C26	0.5489 (3)	1.0946 (3)	0.9963 (2)	0.0508 (5)
H26A	0.5285	1.1232	0.9190	0.061*
H26B	0.4317	1.0394	0.9975	0.061*
O26'	0.6194 (3)	1.2154 (2)	1.10498 (19)	0.0622 (5)
C27	0.7038 (6)	0.9416 (4)	1.1081 (3)	0.0717 (9)
H27A	0.7285	1.0103	1.1865	0.107*
H27B	0.8025	0.8960	1.1124	0.107*
H27C	0.5887	0.8747	1.0925	0.107*
C27'	0.5166 (4)	1.3055 (3)	1.1136 (3)	0.0583 (6)
C28'	0.6078 (6)	1.4313 (4)	1.2226 (4)	0.0869 (11)
H28A	0.5154	1.4753	1.2438	0.130*
H28B	0.6953	1.4948	1.2001	0.130*
H28C	0.6713	1.4048	1.2938	0.130*
O29'	0.3703 (4)	1.2895 (3)	1.0377 (3)	0.0965 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0436 (11)	0.0385 (11)	0.0449 (11)	0.0116 (8)	0.0183 (9)	−0.0044 (8)
C2	0.0435 (11)	0.0385 (11)	0.0569 (13)	0.0178 (9)	0.0121 (9)	0.0010 (9)
C3	0.0527 (12)	0.0401 (11)	0.0487 (12)	0.0147 (9)	0.0141 (10)	0.0082 (9)
O3'	0.0554 (9)	0.0377 (8)	0.0590 (10)	0.0109 (7)	0.0191 (8)	0.0023 (7)
C4	0.0475 (12)	0.0428 (11)	0.0526 (12)	0.0124 (9)	0.0222 (10)	0.0064 (9)
C4'	0.0485 (13)	0.0473 (14)	0.0824 (19)	0.0109 (11)	0.0163 (12)	0.0092 (13)
C5	0.0349 (9)	0.0406 (11)	0.0432 (10)	0.0097 (8)	0.0093 (8)	0.0001 (8)
C5'	0.0692 (19)	0.0542 (17)	0.107 (3)	−0.0003 (14)	0.0214 (18)	−0.0086 (18)
C6	0.0347 (10)	0.0481 (13)	0.0637 (14)	0.0147 (9)	0.0142 (9)	0.0035 (10)
O6'	0.0871 (16)	0.0801 (16)	0.0926 (18)	−0.0024 (13)	0.0378 (14)	0.0247 (14)
C7	0.0363 (10)	0.0461 (12)	0.0575 (13)	0.0135 (9)	0.0214 (9)	0.0005 (10)
C8	0.0365 (9)	0.0355 (10)	0.0389 (10)	0.0145 (8)	0.0138 (7)	0.0037 (8)
C9	0.0353 (9)	0.0361 (9)	0.0340 (9)	0.0131 (7)	0.0134 (7)	0.0030 (7)
C10	0.0392 (10)	0.0379 (10)	0.0351 (9)	0.0139 (8)	0.0127 (8)	0.0019 (7)
C11	0.0402 (10)	0.0408 (11)	0.0473 (11)	0.0133 (8)	0.0206 (9)	−0.0027 (9)
C12	0.0346 (9)	0.0371 (10)	0.0479 (11)	0.0131 (8)	0.0128 (8)	0.0007 (8)
C13	0.0365 (9)	0.0340 (9)	0.0336 (9)	0.0146 (7)	0.0137 (7)	0.0028 (7)
C14	0.0389 (9)	0.0352 (10)	0.0351 (9)	0.0126 (8)	0.0170 (8)	0.0038 (7)
C15	0.0472 (11)	0.0405 (11)	0.0509 (12)	0.0116 (9)	0.0273 (10)	−0.0019 (9)
C16	0.0565 (12)	0.0407 (11)	0.0423 (10)	0.0109 (9)	0.0276 (9)	−0.0010 (9)
C17	0.0464 (10)	0.0391 (10)	0.0334 (9)	0.0138 (8)	0.0136 (8)	0.0024 (8)
C18	0.0460 (11)	0.0455 (11)	0.0408 (10)	0.0156 (9)	0.0150 (8)	0.0132 (8)
C19	0.0650 (14)	0.0556 (14)	0.0369 (10)	0.0173 (11)	0.0122 (10)	0.0069 (9)
C20	0.0420 (10)	0.0398 (11)	0.0401 (10)	0.0119 (8)	0.0107 (8)	−0.0006 (8)
C21	0.0447 (11)	0.0533 (14)	0.0633 (15)	0.0092 (10)	0.0240 (11)	−0.0044 (11)
C21'	0.0618 (14)	0.0456 (12)	0.0454 (12)	0.0139 (10)	0.0010 (10)	−0.0019 (9)
O21'	0.0925 (16)	0.0896 (17)	0.0424 (10)	0.0308 (13)	0.0105 (10)	0.0058 (10)
C22	0.0426 (10)	0.0413 (11)	0.0370 (9)	0.0126 (8)	0.0150 (8)	0.0000 (8)
C22'	0.0695 (19)	0.080 (2)	0.079 (2)	0.0325 (17)	−0.0111 (16)	0.0028 (17)
O22'	0.0467 (8)	0.0382 (8)	0.0691 (11)	0.0112 (6)	0.0270 (8)	−0.0032 (7)
C23	0.0458 (11)	0.0415 (11)	0.0366 (10)	0.0126 (9)	0.0131 (8)	0.0037 (8)
C23'	0.0503 (12)	0.0454 (12)	0.0413 (11)	0.0117 (9)	0.0166 (9)	0.0032 (9)
C23"	0.0702 (18)	0.083 (2)	0.087 (2)	0.0188 (16)	0.0384 (17)	0.0426 (19)
O23"	0.0471 (9)	0.0544 (11)	0.0709 (12)	0.0083 (8)	0.0049 (8)	0.0077 (9)
C24	0.0472 (11)	0.0407 (11)	0.0431 (11)	0.0146 (9)	0.0109 (9)	0.0022 (9)
C25	0.0434 (10)	0.0441 (11)	0.0419 (11)	0.0131 (9)	0.0152 (8)	0.0025 (9)
C26	0.0511 (12)	0.0451 (12)	0.0506 (13)	0.0161 (10)	0.0119 (10)	0.0016 (10)
O26'	0.0618 (11)	0.0567 (11)	0.0592 (11)	0.0249 (9)	0.0155 (9)	−0.0085 (9)
C27	0.099 (2)	0.085 (2)	0.0516 (15)	0.0499 (19)	0.0346 (15)	0.0236 (14)
C27'	0.0698 (16)	0.0541 (15)	0.0589 (15)	0.0259 (12)	0.0291 (13)	0.0110 (12)
C28'	0.108 (3)	0.073 (2)	0.078 (2)	0.039 (2)	0.036 (2)	−0.0064 (18)
O29'	0.0934 (18)	0.0785 (17)	0.106 (2)	0.0506 (15)	0.0078 (15)	−0.0001 (15)

Geometric parameters (Å, º)

C1—C2	1.527 (4)	C16—O22'	1.443 (3)
C1—C10	1.549 (3)	C16—C17	1.552 (3)
C1—H1A	0.9700	C16—H16A	0.9800
C1—H1B	0.9700	C17—C20	1.563 (3)
C2—C3	1.512 (3)	C17—H17A	0.9800
C2—H2A	0.9700	C18—H18A	0.9600
C2—H2B	0.9700	C18—H18B	0.9600
C3—O3'	1.469 (3)	C18—H18C	0.9600
C3—C4	1.523 (3)	C19—H19A	0.9600
C3—H3A	0.9800	C19—H19B	0.9600
O3'—C4'	1.339 (4)	C19—H19C	0.9600
C4—C5	1.539 (4)	C20—C22	1.532 (3)
C4—H4A	0.9700	C20—C21	1.541 (3)
C4—H4B	0.9700	C20—C21'	1.548 (3)
C4'—O6'	1.204 (4)	C21—H21A	0.9600
C4'—C5'	1.485 (5)	C21—H21B	0.9600
C5—C6	1.545 (3)	C21—H21C	0.9600
C5—C10	1.558 (3)	C21'—O21'	1.209 (4)
C5—H5A	0.9800	C21'—C22'	1.506 (4)
C5'—H5B	0.9600	C22—C23	1.340 (3)
C5'—H5C	0.9600	C22—O22'	1.360 (3)
C5'—H5D	0.9600	C22'—H22A	0.9600
C6—C7	1.528 (3)	C22'—H22B	0.9600
C6—H6A	0.9700	C22'—H22C	0.9600
C6—H6B	0.9700	C23—C23'	1.482 (3)
C7—C8	1.532 (3)	C23—C24	1.520 (3)
C7—H7A	0.9700	C23'—O23"	1.218 (3)
C7—H7B	0.9700	C23'—C23"	1.508 (4)
C8—C14	1.527 (3)	C23"—H23A	0.9600
C8—C9	1.543 (2)	C23"—H23B	0.9600
C8—H8A	0.9800	C23"—H23C	0.9600
C9—C11	1.542 (3)	C24—C25	1.546 (3)
C9—C10	1.557 (3)	C24—H24A	0.9700
C9—H9A	0.9800	C24—H24B	0.9700
C10—C19	1.536 (3)	C25—C27	1.509 (4)
C11—C12	1.537 (3)	C25—C26	1.512 (3)
C11—H11A	0.9700	C25—H25A	0.9800
C11—H11B	0.9700	C26—O26'	1.453 (3)
C12—C13	1.534 (2)	C26—H26A	0.9700
C12—H12A	0.9700	C26—H26B	0.9700
C12—H12B	0.9700	O26'—C27'	1.327 (3)
C13—C18	1.543 (3)	C27—H27A	0.9600
C13—C14	1.551 (3)	C27—H27B	0.9600
C13—C17	1.558 (3)	C27—H27C	0.9600
C14—C15	1.542 (3)	C27'—O29'	1.199 (4)
C14—H14A	0.9800	C27'—C28'	1.494 (5)
C15—C16	1.533 (3)	C28'—H28A	0.9600
C15—H15A	0.9700	C28'—H28B	0.9600
C15—H15B	0.9700	C28'—H28C	0.9600
C2—C1—C10	114.33 (17)	C14—C15—H15B	111.3
C2—C1—H1A	108.7	H15A—C15—H15B	109.2
C10—C1—H1A	108.7	O22'—C16—C15	111.8 (2)
C2—C1—H1B	108.7	O22'—C16—C17	105.01 (17)
C10—C1—H1B	108.7	C15—C16—C17	107.73 (16)
H1A—C1—H1B	107.6	O22'—C16—H16A	110.7
C3—C2—C1	111.57 (18)	C15—C16—H16A	110.7
C3—C2—H2A	109.3	C17—C16—H16A	110.7
C1—C2—H2A	109.3	C16—C17—C13	104.05 (16)
C3—C2—H2B	109.3	C16—C17—C20	103.19 (16)
C1—C2—H2B	109.3	C13—C17—C20	123.39 (18)
H2A—C2—H2B	108.0	C16—C17—H17A	108.4
O3'—C3—C2	105.50 (18)	C13—C17—H17A	108.4
O3'—C3—C4	110.91 (19)	C20—C17—H17A	108.4
C2—C3—C4	111.77 (19)	C13—C18—H18A	109.5
O3'—C3—H3A	109.5	C13—C18—H18B	109.5
C2—C3—H3A	109.5	H18A—C18—H18B	109.5
C4—C3—H3A	109.5	C13—C18—H18C	109.5
C4'—O3'—C3	117.9 (2)	H18A—C18—H18C	109.5
C3—C4—C5	114.73 (19)	H18B—C18—H18C	109.5
C3—C4—H4A	108.6	C10—C19—H19A	109.5
C5—C4—H4A	108.6	C10—C19—H19B	109.5
C3—C4—H4B	108.6	H19A—C19—H19B	109.5
C5—C4—H4B	108.6	C10—C19—H19C	109.5
H4A—C4—H4B	107.6	H19A—C19—H19C	109.5
O6'—C4'—O3'	123.4 (3)	H19B—C19—H19C	109.5
O6'—C4'—C5'	125.3 (3)	C22—C20—C21	116.1 (2)
O3'—C4'—C5'	111.2 (3)	C22—C20—C21'	107.34 (18)
C4—C5—C6	109.44 (19)	C21—C20—C21'	112.4 (2)
C4—C5—C10	113.52 (17)	C22—C20—C17	102.43 (17)
C6—C5—C10	111.34 (19)	C21—C20—C17	113.59 (17)
C4—C5—H5A	107.4	C21'—C20—C17	103.8 (2)
C6—C5—H5A	107.4	C20—C21—H21A	109.5
C10—C5—H5A	107.4	C20—C21—H21B	109.5
C4'—C5'—H5B	109.5	H21A—C21—H21B	109.5
C4'—C5'—H5C	109.5	C20—C21—H21C	109.5
H5B—C5'—H5C	109.5	H21A—C21—H21C	109.5
C4'—C5'—H5D	109.5	H21B—C21—H21C	109.5
H5B—C5'—H5D	109.5	O21'—C21'—C22'	120.7 (3)
H5C—C5'—H5D	109.5	O21'—C21'—C20	120.0 (3)
C7—C6—C5	112.11 (18)	C22'—C21'—C20	119.1 (3)
C7—C6—H6A	109.2	C23—C22—O22'	118.98 (19)
C5—C6—H6A	109.2	C23—C22—C20	130.3 (2)
C7—C6—H6B	109.2	O22'—C22—C20	110.74 (19)
C5—C6—H6B	109.2	C21'—C22'—H22A	109.5
H6A—C6—H6B	107.9	C21'—C22'—H22B	109.5
C6—C7—C8	112.52 (19)	H22A—C22'—H22B	109.5
C6—C7—H7A	109.1	C21'—C22'—H22C	109.5
C8—C7—H7A	109.1	H22A—C22'—H22C	109.5
C6—C7—H7B	109.1	H22B—C22'—H22C	109.5
C8—C7—H7B	109.1	C22—O22'—C16	111.54 (17)
H7A—C7—H7B	107.8	C22—C23—C23'	120.6 (2)
C14—C8—C7	111.17 (17)	C22—C23—C24	121.9 (2)
C14—C8—C9	107.65 (15)	C23'—C23—C24	117.4 (2)
C7—C8—C9	111.25 (16)	O23"—C23'—C23	122.3 (2)
C14—C8—H8A	108.9	O23"—C23'—C23"	119.8 (3)
C7—C8—H8A	108.9	C23—C23'—C23"	117.9 (2)
C9—C8—H8A	108.9	C23'—C23"—H23A	109.5
C11—C9—C8	110.40 (16)	C23'—C23"—H23B	109.5
C11—C9—C10	113.86 (15)	H23A—C23"—H23B	109.5
C8—C9—C10	113.02 (15)	C23'—C23"—H23C	109.5
C11—C9—H9A	106.3	H23A—C23"—H23C	109.5
C8—C9—H9A	106.3	H23B—C23"—H23C	109.5
C10—C9—H9A	106.3	C23—C24—C25	111.88 (18)
C19—C10—C1	107.49 (18)	C23—C24—H24A	109.2
C19—C10—C9	111.33 (19)	C25—C24—H24A	109.2
C1—C10—C9	111.13 (16)	C23—C24—H24B	109.2
C19—C10—C5	109.23 (18)	C25—C24—H24B	109.2
C1—C10—C5	107.28 (18)	H24A—C24—H24B	107.9
C9—C10—C5	110.26 (16)	C27—C25—C26	112.6 (2)
C12—C11—C9	113.23 (17)	C27—C25—C24	111.4 (2)
C12—C11—H11A	108.9	C26—C25—C24	109.09 (18)
C9—C11—H11A	108.9	C27—C25—H25A	107.9
C12—C11—H11B	108.9	C26—C25—H25A	107.9
C9—C11—H11B	108.9	C24—C25—H25A	107.9
H11A—C11—H11B	107.7	O26'—C26—C25	107.91 (18)
C13—C12—C11	111.44 (16)	O26'—C26—H26A	110.1
C13—C12—H12A	109.3	C25—C26—H26A	110.1
C11—C12—H12A	109.3	O26'—C26—H26B	110.1
C13—C12—H12B	109.3	C25—C26—H26B	110.1
C11—C12—H12B	109.3	H26A—C26—H26B	108.4
H12A—C12—H12B	108.0	C27'—O26'—C26	116.9 (2)
C12—C13—C18	110.13 (16)	C25—C27—H27A	109.5
C12—C13—C14	107.95 (15)	C25—C27—H27B	109.5
C18—C13—C14	111.23 (16)	H27A—C27—H27B	109.5
C12—C13—C17	115.08 (16)	C25—C27—H27C	109.5
C18—C13—C17	113.14 (17)	H27A—C27—H27C	109.5
C14—C13—C17	98.68 (15)	H27B—C27—H27C	109.5
C8—C14—C15	120.09 (17)	O29'—C27'—O26'	122.9 (3)
C8—C14—C13	114.68 (15)	O29'—C27'—C28'	124.2 (3)
C15—C14—C13	103.69 (15)	O26'—C27'—C28'	112.8 (3)
C8—C14—H14A	105.8	C27'—C28'—H28A	109.5
C15—C14—H14A	105.8	C27'—C28'—H28B	109.5
C13—C14—H14A	105.8	H28A—C28'—H28B	109.5
C16—C15—C14	102.16 (17)	C27'—C28'—H28C	109.5
C16—C15—H15A	111.3	H28A—C28'—H28C	109.5
C14—C15—H15A	111.3	H28B—C28'—H28C	109.5
C16—C15—H15B	111.3
C10—C1—C2—C3	57.7 (2)	C13—C14—C15—C16	−39.4 (2)
C1—C2—C3—O3'	69.2 (2)	C14—C15—C16—O22'	128.86 (18)
C1—C2—C3—C4	−51.5 (2)	C14—C15—C16—C17	14.0 (2)
C2—C3—O3'—C4'	155.7 (2)	O22'—C16—C17—C13	−103.25 (19)
C4—C3—O3'—C4'	−83.1 (3)	C15—C16—C17—C13	16.0 (2)
O3'—C3—C4—C5	−68.4 (3)	O22'—C16—C17—C20	26.6 (2)
C2—C3—C4—C5	49.0 (3)	C15—C16—C17—C20	145.88 (19)
C3—O3'—C4'—O6'	4.9 (4)	C12—C13—C17—C16	−153.37 (19)
C3—O3'—C4'—C5'	−174.4 (2)	C18—C13—C17—C16	78.8 (2)
C3—C4—C5—C6	−175.25 (19)	C14—C13—C17—C16	−38.8 (2)
C3—C4—C5—C10	−50.2 (3)	C12—C13—C17—C20	90.1 (2)
C4—C5—C6—C7	71.3 (3)	C18—C13—C17—C20	−37.7 (3)
C10—C5—C6—C7	−55.0 (3)	C14—C13—C17—C20	−155.33 (19)
C5—C6—C7—C8	54.7 (3)	C16—C17—C20—C22	−21.8 (2)
C6—C7—C8—C14	−173.11 (19)	C13—C17—C20—C22	95.2 (2)
C6—C7—C8—C9	−53.1 (3)	C16—C17—C20—C21	−147.8 (2)
C14—C8—C9—C11	−55.9 (2)	C13—C17—C20—C21	−30.9 (3)
C7—C8—C9—C11	−177.91 (19)	C16—C17—C20—C21'	89.9 (2)
C14—C8—C9—C10	175.30 (17)	C13—C17—C20—C21'	−153.2 (2)
C7—C8—C9—C10	53.3 (2)	C22—C20—C21'—O21'	30.8 (3)
C2—C1—C10—C19	−173.06 (19)	C21—C20—C21'—O21'	159.6 (3)
C2—C1—C10—C9	64.9 (2)	C17—C20—C21'—O21'	−77.2 (3)
C2—C1—C10—C5	−55.7 (2)	C22—C20—C21'—C22'	−153.4 (3)
C11—C9—C10—C19	−59.3 (2)	C21—C20—C21'—C22'	−24.6 (4)
C8—C9—C10—C19	67.7 (2)	C17—C20—C21'—C22'	98.6 (3)
C11—C9—C10—C1	60.5 (2)	C21—C20—C22—C23	−45.7 (3)
C8—C9—C10—C1	−172.52 (17)	C21'—C20—C22—C23	81.0 (3)
C11—C9—C10—C5	179.28 (18)	C17—C20—C22—C23	−170.1 (2)
C8—C9—C10—C5	−53.7 (2)	C21—C20—C22—O22'	134.3 (2)
C4—C5—C10—C19	167.16 (18)	C21'—C20—C22—O22'	−99.0 (2)
C6—C5—C10—C19	−68.8 (2)	C17—C20—C22—O22'	9.9 (2)
C4—C5—C10—C1	50.9 (2)	C23—C22—O22'—C16	−172.42 (19)
C6—C5—C10—C1	174.98 (18)	C20—C22—O22'—C16	7.5 (2)
C4—C5—C10—C9	−70.2 (2)	C15—C16—O22'—C22	−138.47 (18)
C6—C5—C10—C9	53.8 (2)	C17—C16—O22'—C22	−22.0 (2)
C8—C9—C11—C12	56.0 (2)	O22'—C22—C23—C23'	176.8 (2)
C10—C9—C11—C12	−175.66 (18)	C20—C22—C23—C23'	−3.2 (3)
C9—C11—C12—C13	−55.0 (3)	O22'—C22—C23—C24	1.3 (3)
C11—C12—C13—C18	−68.5 (2)	C20—C22—C23—C24	−178.6 (2)
C11—C12—C13—C14	53.2 (2)	C22—C23—C23'—O23"	−33.0 (3)
C11—C12—C13—C17	162.23 (19)	C24—C23—C23'—O23"	142.7 (2)
C7—C8—C14—C15	−53.6 (3)	C22—C23—C23'—C23"	146.7 (3)
C9—C8—C14—C15	−175.70 (18)	C24—C23—C23'—C23"	−37.7 (3)
C7—C8—C14—C13	−178.19 (17)	C22—C23—C24—C25	116.1 (2)
C9—C8—C14—C13	59.7 (2)	C23'—C23—C24—C25	−59.4 (3)
C12—C13—C14—C8	−58.3 (2)	C23—C24—C25—C27	−60.6 (3)
C18—C13—C14—C8	62.6 (2)	C23—C24—C25—C26	174.5 (2)
C17—C13—C14—C8	−178.36 (16)	C27—C25—C26—O26'	70.0 (3)
C12—C13—C14—C15	168.81 (18)	C24—C25—C26—O26'	−165.8 (2)
C18—C13—C14—C15	−70.3 (2)	C25—C26—O26'—C27'	177.3 (2)
C17—C13—C14—C15	48.8 (2)	C26—O26'—C27'—O29'	1.2 (5)
C8—C14—C15—C16	−169.01 (19)	C26—O26'—C27'—C28'	−175.3 (3)