Solving the problem of the configuration of the double bond at C22 in (25S)-23-acetyl-5β-furost-22-ene-3β,26-diyl di­acetate

The crystal structure of the title compound, C₃₃H₅₀O₆, confirms that the double bond at C22, with a length of 1.355 (3) Å, has an E configuration, in agreement with NMR data.

Key indicators

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.133
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....       C27'

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....       O26'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....       C23'
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C25
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......       C23"
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

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           28.00
           From the CIF: _reflns_number_total               4144
           Count of symmetry unique reflns         4145
           Completeness (_total/calc)             99.98%
           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
   2 ALERT level B = Potentially serious problem
   9 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 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.

(I)

Crystal data

C33H50O6	F(000) = 592
Mr = 542.73	Dx = 1.131 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 68 reflections
a = 12.9463 (14) Å	θ = 4.6–12.5°
b = 7.3819 (10) Å	µ = 0.08 mm^−1
c = 16.8664 (17) Å	T = 300 K
β = 98.562 (6)°	Prism, colorless
V = 1593.9 (3) Å^3	0.65 × 0.50 × 0.38 mm
Z = 2

Data collection

Bruker P4 diffractometer	Rint = 0.028
Radiation source: fine-focus sealed tube, FN4	θmax = 28.0°, θmin = 1.6°
Graphite monochromator	h = −17→8
2θ/ω scans	k = −1→9
7849 measured reflections	l = −22→22
4144 independent reflections	3 standard reflections every 97 reflections
3498 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0712P)^2 + 0.1538P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4144 reflections	Δρmax = 0.25 e Å^−3
363 parameters	Δρmin = −0.19 e Å^−3
1 restraint	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

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	Occ. (<1)
C1	0.8280 (2)	0.8269 (5)	0.15861 (12)	0.0606 (7)
H1A	0.8801	0.8204	0.1229	0.073*
H1B	0.7975	0.7073	0.1606	0.073*
C2	0.7442 (2)	0.9561 (6)	0.12383 (14)	0.0715 (9)
H2A	0.6872	0.9511	0.1551	0.086*
H2B	0.7172	0.9190	0.0695	0.086*
C3	0.7837 (2)	1.1492 (5)	0.12267 (15)	0.0706 (8)
H3A	0.7253	1.2316	0.1057	0.085*
O3'	0.85872 (15)	1.1570 (4)	0.06517 (10)	0.0766 (6)
C4'	0.8451 (3)	1.2727 (6)	0.00780 (19)	0.0904 (11)
C5'	0.9293 (2)	1.2709 (5)	−0.04377 (15)	0.0783 (9)
H5'A	0.9518	1.1486	−0.0501	0.118*
H5'B	0.9873	1.3423	−0.0190	0.118*
H5'C	0.9029	1.3208	−0.0954	0.118*
O6'	0.7500 (5)	1.3115 (17)	−0.0225 (4)	0.105 (4)	0.532 (16)
O6'A	0.8021 (12)	1.4236 (14)	0.0237 (8)	0.128 (6)	0.468 (16)
C4	0.8408 (2)	1.2072 (4)	0.20367 (15)	0.0649 (7)
H4A	0.7903	1.2227	0.2402	0.078*
H4B	0.8734	1.3239	0.1979	0.078*
C5	0.92394 (18)	1.0745 (4)	0.24030 (12)	0.0544 (6)
H5A	0.9780	1.0731	0.2053	0.065*
C6	0.9769 (2)	1.1381 (5)	0.32293 (13)	0.0694 (8)
H6A	1.0389	1.0655	0.3392	0.083*
H6B	0.9988	1.2631	0.3192	0.083*
C7	0.9047 (2)	1.1231 (4)	0.38647 (13)	0.0619 (7)
H7A	0.8479	1.2089	0.3742	0.074*
H7B	0.9434	1.1551	0.4383	0.074*
C8	0.85951 (16)	0.9325 (4)	0.39116 (11)	0.0476 (5)
H8A	0.9160	0.8489	0.4118	0.057*
C9	0.80689 (16)	0.8662 (4)	0.30687 (11)	0.0459 (5)
H9A	0.7505	0.9522	0.2892	0.055*
C10	0.88312 (17)	0.8768 (4)	0.24352 (12)	0.0503 (5)
C11	0.7544 (2)	0.6803 (4)	0.31129 (12)	0.0560 (6)
H11A	0.8074	0.5899	0.3285	0.067*
H11B	0.7199	0.6467	0.2583	0.067*
C12	0.67375 (18)	0.6816 (4)	0.36990 (11)	0.0528 (6)
H12A	0.6171	0.7633	0.3501	0.063*
H12B	0.6448	0.5611	0.3730	0.063*
C13	0.72405 (16)	0.7422 (3)	0.45369 (11)	0.0434 (4)
C14	0.77652 (17)	0.9286 (3)	0.44662 (11)	0.0448 (5)
H14A	0.7207	1.0093	0.4219	0.054*
C15	0.80277 (19)	0.9913 (4)	0.53439 (11)	0.0545 (6)
H15A	0.8658	0.9335	0.5611	0.065*
H15B	0.8112	1.1217	0.5379	0.065*
C16	0.70632 (18)	0.9293 (3)	0.57018 (11)	0.0481 (5)
H16A	0.6632	1.0331	0.5807	0.058*
C17	0.64457 (15)	0.7985 (3)	0.50959 (10)	0.0440 (5)
H17A	0.5863	0.8637	0.4783	0.053*
C18	0.79967 (18)	0.5962 (4)	0.49181 (14)	0.0548 (6)
H18A	0.8475	0.5651	0.4556	0.082*
H18B	0.7610	0.4905	0.5028	0.082*
H18C	0.8380	0.6414	0.5409	0.082*
C19	0.9746 (2)	0.7446 (5)	0.26413 (17)	0.0733 (8)
H19A	1.0203	0.7535	0.2244	0.110*
H19B	0.9482	0.6232	0.2651	0.110*
H19C	1.0125	0.7744	0.3158	0.110*
C20	0.60167 (15)	0.6580 (3)	0.56277 (10)	0.0444 (5)
H20A	0.5987	0.5374	0.5382	0.053*
C21	0.49508 (17)	0.7147 (4)	0.58314 (13)	0.0562 (6)
H21A	0.4702	0.6241	0.6165	0.084*
H21B	0.4465	0.7274	0.5346	0.084*
H21C	0.5016	0.8283	0.6111	0.084*
C22	0.67995 (15)	0.6638 (3)	0.63885 (11)	0.0437 (4)
O22'	0.73500 (12)	0.8205 (3)	0.64298 (7)	0.0512 (4)
C23	0.69628 (17)	0.5453 (3)	0.70078 (11)	0.0471 (5)
C23'	0.6438 (2)	0.3698 (4)	0.69456 (14)	0.0560 (6)
C23"	0.6662 (4)	0.2353 (6)	0.7619 (2)	0.1128 (15)
H23A	0.6257	0.1276	0.7486	0.169*
H23B	0.6479	0.2871	0.8101	0.169*
H23C	0.7392	0.2053	0.7699	0.169*
O23"	0.58358 (16)	0.3182 (3)	0.63582 (11)	0.0718 (5)
C24	0.77170 (18)	0.6009 (4)	0.77514 (12)	0.0542 (6)
H24A	0.8355	0.6456	0.7584	0.065*
H24B	0.7895	0.4944	0.8080	0.065*
C25	0.7291 (2)	0.7460 (4)	0.82632 (12)	0.0579 (6)
H25A	0.7079	0.8507	0.7920	0.069*
C26	0.6343 (3)	0.6793 (6)	0.86092 (18)	0.0777 (8)
H26A	0.5813	0.6377	0.8180	0.093*
H26B	0.6539	0.5784	0.8969	0.093*
C27	0.8146 (3)	0.8070 (7)	0.89287 (19)	0.1007 (13)
H27A	0.7874	0.8980	0.9248	0.151*
H27B	0.8719	0.8562	0.8697	0.151*
H27C	0.8383	0.7052	0.9261	0.151*
O26'	0.5933 (2)	0.8252 (5)	0.90403 (14)	0.1071 (10)
C27'	0.5010 (3)	0.8905 (8)	0.8799 (3)	0.1030 (13)
C28'	0.4712 (4)	1.0416 (9)	0.9277 (3)	0.141 (2)
H28A	0.4022	1.0815	0.9061	0.211*
H28B	0.5196	1.1395	0.9262	0.211*
H28C	0.4722	1.0029	0.9821	0.211*
O29'	0.4520 (3)	0.8393 (10)	0.8191 (3)	0.204 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0705 (14)	0.0774 (17)	0.0375 (9)	−0.0182 (15)	0.0207 (10)	−0.0093 (12)
C2	0.0592 (14)	0.116 (3)	0.0401 (10)	−0.0178 (17)	0.0084 (10)	0.0002 (14)
C3	0.0631 (14)	0.101 (2)	0.0500 (12)	0.0137 (17)	0.0164 (10)	0.0216 (15)
O3'	0.0730 (11)	0.1063 (17)	0.0541 (9)	0.0144 (12)	0.0208 (8)	0.0325 (12)
C4'	0.102 (2)	0.107 (3)	0.0681 (17)	0.025 (2)	0.0310 (17)	0.039 (2)
C5'	0.0900 (19)	0.093 (2)	0.0549 (13)	−0.0091 (19)	0.0195 (13)	0.0199 (16)
O6'	0.092 (3)	0.150 (8)	0.073 (4)	0.043 (4)	0.017 (3)	0.052 (5)
O6'A	0.189 (11)	0.096 (6)	0.117 (8)	0.053 (7)	0.083 (9)	0.052 (6)
C4	0.0774 (16)	0.0671 (17)	0.0540 (12)	−0.0042 (15)	0.0218 (12)	0.0051 (12)
C5	0.0527 (11)	0.0718 (17)	0.0408 (10)	−0.0144 (13)	0.0137 (9)	0.0014 (11)
C6	0.0658 (14)	0.097 (2)	0.0471 (11)	−0.0366 (16)	0.0132 (10)	−0.0058 (14)
C7	0.0670 (14)	0.0778 (19)	0.0415 (10)	−0.0272 (14)	0.0097 (9)	−0.0086 (12)
C8	0.0457 (10)	0.0625 (14)	0.0348 (9)	−0.0068 (11)	0.0064 (8)	0.0003 (9)
C9	0.0471 (10)	0.0580 (13)	0.0339 (8)	−0.0036 (10)	0.0104 (7)	−0.0001 (9)
C10	0.0507 (11)	0.0653 (15)	0.0369 (9)	−0.0057 (11)	0.0138 (8)	0.0002 (10)
C11	0.0676 (13)	0.0646 (15)	0.0383 (9)	−0.0171 (13)	0.0163 (9)	−0.0091 (11)
C12	0.0566 (11)	0.0677 (15)	0.0352 (9)	−0.0199 (12)	0.0102 (8)	−0.0055 (10)
C13	0.0457 (10)	0.0536 (12)	0.0319 (8)	−0.0051 (10)	0.0087 (7)	−0.0004 (9)
C14	0.0478 (10)	0.0552 (12)	0.0313 (8)	−0.0048 (10)	0.0062 (7)	0.0010 (9)
C15	0.0664 (13)	0.0628 (15)	0.0352 (9)	−0.0145 (13)	0.0101 (9)	−0.0044 (10)
C16	0.0622 (12)	0.0501 (12)	0.0329 (8)	−0.0007 (11)	0.0099 (8)	0.0001 (9)
C17	0.0450 (9)	0.0552 (12)	0.0320 (8)	0.0004 (10)	0.0061 (7)	0.0010 (9)
C18	0.0551 (12)	0.0605 (14)	0.0512 (11)	0.0078 (12)	0.0161 (9)	0.0036 (11)
C19	0.0693 (15)	0.089 (2)	0.0678 (15)	0.0152 (17)	0.0292 (13)	0.0070 (16)
C20	0.0457 (10)	0.0538 (12)	0.0341 (8)	−0.0010 (10)	0.0077 (7)	0.0011 (9)
C21	0.0490 (11)	0.0701 (17)	0.0505 (11)	0.0000 (12)	0.0103 (9)	0.0061 (12)
C22	0.0451 (9)	0.0530 (12)	0.0342 (8)	0.0023 (10)	0.0102 (7)	−0.0020 (9)
O22'	0.0613 (8)	0.0612 (10)	0.0306 (6)	−0.0091 (9)	0.0049 (6)	0.0005 (7)
C23	0.0516 (11)	0.0556 (13)	0.0348 (9)	0.0100 (11)	0.0087 (8)	0.0016 (9)
C23'	0.0670 (14)	0.0546 (14)	0.0474 (10)	0.0104 (12)	0.0116 (10)	0.0044 (10)
C23"	0.187 (4)	0.065 (2)	0.077 (2)	−0.016 (3)	−0.015 (2)	0.0201 (18)
O23"	0.0820 (12)	0.0638 (12)	0.0661 (10)	−0.0129 (11)	−0.0004 (9)	0.0058 (10)
C24	0.0563 (12)	0.0666 (15)	0.0384 (9)	0.0115 (12)	0.0028 (8)	0.0042 (11)
C25	0.0754 (15)	0.0612 (14)	0.0364 (9)	0.0071 (13)	0.0055 (10)	0.0006 (10)
C26	0.0845 (18)	0.087 (2)	0.0670 (15)	0.0103 (19)	0.0278 (13)	−0.0126 (17)
C27	0.099 (2)	0.126 (3)	0.0724 (18)	−0.015 (3)	−0.0007 (16)	−0.040 (2)
O26'	0.0982 (16)	0.139 (3)	0.0842 (14)	0.0391 (19)	0.0151 (12)	−0.0392 (17)
C27'	0.082 (2)	0.123 (4)	0.108 (3)	0.016 (3)	0.028 (2)	−0.014 (3)
C28'	0.124 (3)	0.139 (5)	0.173 (4)	0.039 (4)	0.068 (3)	−0.026 (4)
O29'	0.116 (2)	0.250 (7)	0.232 (5)	0.066 (4)	−0.024 (3)	−0.087 (5)

Geometric parameters (Å, º)

C1—C2	1.497 (5)	C15—C16	1.535 (3)
C1—C10	1.547 (3)	C15—H15A	0.970
C1—H1A	0.970	C15—H15B	0.970
C1—H1B	0.970	C16—O22'	1.468 (2)
C2—C3	1.515 (6)	C16—C17	1.540 (3)
C2—H2A	0.970	C16—H16A	0.980
C2—H2B	0.970	C17—C20	1.529 (3)
C3—O3'	1.472 (3)	C17—H17A	0.980
C3—C4	1.515 (4)	C18—H18A	0.960
C3—H3A	0.980	C18—H18B	0.960
O3'—C4'	1.283 (4)	C18—H18C	0.960
C4'—O6'A	1.291 (9)	C19—H19A	0.960
C4'—O6'	1.292 (6)	C19—H19B	0.960
C4'—C5'	1.493 (4)	C19—H19C	0.960
C5'—H5'A	0.960	C20—C22	1.513 (3)
C5'—H5'B	0.960	C20—C21	1.529 (3)
C5'—H5'C	0.960	C20—H20A	0.980
O6'—O6'A	1.262 (11)	C21—H21A	0.960
C4—C5	1.517 (4)	C21—H21B	0.960
C4—H4A	0.970	C21—H21C	0.960
C4—H4B	0.970	C22—O22'	1.355 (3)
C5—C6	1.533 (3)	C22—C23	1.355 (3)
C5—C10	1.556 (4)	C23—C23'	1.459 (4)
C5—H5A	0.980	C23—C24	1.526 (3)
C6—C7	1.527 (3)	C23'—O23"	1.227 (3)
C6—H6A	0.970	C23'—C23"	1.503 (4)
C6—H6B	0.970	C23"—H23A	0.960
C7—C8	1.531 (4)	C23"—H23B	0.960
C7—H7A	0.970	C23"—H23C	0.960
C7—H7B	0.970	C24—C25	1.530 (4)
C8—C14	1.526 (3)	C24—H24A	0.970
C8—C9	1.561 (3)	C24—H24B	0.970
C8—H8A	0.980	C25—C26	1.517 (4)
C9—C11	1.538 (4)	C25—C27	1.522 (4)
C9—C10	1.561 (3)	C25—H25A	0.980
C9—H9A	0.980	C26—O26'	1.444 (4)
C10—C19	1.533 (4)	C26—H26A	0.970
C11—C12	1.541 (3)	C26—H26B	0.970
C11—H11A	0.970	C27—H27A	0.960
C11—H11B	0.970	C27—H27B	0.960
C12—C13	1.532 (3)	C27—H27C	0.960
C12—H12A	0.970	O26'—C27'	1.297 (5)
C12—H12B	0.970	C27'—O29'	1.185 (6)
C13—C18	1.532 (3)	C27'—C28'	1.461 (7)
C13—C14	1.547 (3)	C28'—H28A	0.960
C13—C17	1.552 (3)	C28'—H28B	0.960
C14—C15	1.540 (3)	C28'—H28C	0.960
C14—H14A	0.980
C2—C1—C10	114.7 (2)	C8—C14—H14A	105.6
C2—C1—H1A	108.6	C15—C14—H14A	105.6
C10—C1—H1A	108.6	C13—C14—H14A	105.6
C2—C1—H1B	108.6	C16—C15—C14	102.25 (17)
C10—C1—H1B	108.6	C16—C15—H15A	111.3
H1A—C1—H1B	107.6	C14—C15—H15A	111.3
C1—C2—C3	112.2 (2)	C16—C15—H15B	111.3
C1—C2—H2A	109.2	C14—C15—H15B	111.3
C3—C2—H2A	109.2	H15A—C15—H15B	109.2
C1—C2—H2B	109.2	O22'—C16—C15	111.88 (18)
C3—C2—H2B	109.2	O22'—C16—C17	104.71 (18)
H2A—C2—H2B	107.9	C15—C16—C17	107.35 (16)
O3'—C3—C4	107.6 (2)	O22'—C16—H16A	110.9
O3'—C3—C2	107.6 (3)	C15—C16—H16A	110.9
C4—C3—C2	112.0 (2)	C17—C16—H16A	110.9
O3'—C3—H3A	109.9	C20—C17—C16	103.54 (15)
C4—C3—H3A	109.9	C20—C17—C13	120.4 (2)
C2—C3—H3A	109.9	C16—C17—C13	104.20 (16)
C4'—O3'—C3	119.5 (3)	C20—C17—H17A	109.3
O3'—C4'—O6'A	115.6 (5)	C16—C17—H17A	109.3
O3'—C4'—O6'	117.5 (4)	C13—C17—H17A	109.3
O6'A—C4'—O6'	58.5 (5)	C13—C18—H18A	109.5
O3'—C4'—C5'	113.8 (3)	C13—C18—H18B	109.5
O6'A—C4'—C5'	120.2 (5)	H18A—C18—H18B	109.5
O6'—C4'—C5'	120.4 (3)	C13—C18—H18C	109.5
C4'—C5'—H5'A	109.5	H18A—C18—H18C	109.5
C4'—C5'—H5'B	109.5	H18B—C18—H18C	109.5
H5'A—C5'—H5'B	109.5	C10—C19—H19A	109.5
C4'—C5'—H5'C	109.5	C10—C19—H19B	109.5
H5'A—C5'—H5'C	109.5	H19A—C19—H19B	109.5
H5'B—C5'—H5'C	109.5	C10—C19—H19C	109.5
O6'A—O6'—C4'	60.7 (5)	H19A—C19—H19C	109.5
O6'—O6'A—C4'	60.8 (6)	H19B—C19—H19C	109.5
C3—C4—C5	113.9 (3)	C22—C20—C17	102.84 (17)
C3—C4—H4A	108.8	C22—C20—C21	108.32 (15)
C5—C4—H4A	108.8	C17—C20—C21	111.4 (2)
C3—C4—H4B	108.8	C22—C20—H20A	111.3
C5—C4—H4B	108.8	C17—C20—H20A	111.3
H4A—C4—H4B	107.7	C21—C20—H20A	111.3
C4—C5—C6	111.5 (3)	C20—C21—H21A	109.5
C4—C5—C10	113.3 (2)	C20—C21—H21B	109.5
C6—C5—C10	111.3 (2)	H21A—C21—H21B	109.5
C4—C5—H5A	106.7	C20—C21—H21C	109.5
C6—C5—H5A	106.7	H21A—C21—H21C	109.5
C10—C5—H5A	106.7	H21B—C21—H21C	109.5
C7—C6—C5	112.21 (19)	O22'—C22—C23	119.43 (18)
C7—C6—H6A	109.2	O22'—C22—C20	110.42 (18)
C5—C6—H6A	109.2	C23—C22—C20	130.0 (2)
C7—C6—H6B	109.2	C22—O22'—C16	110.99 (15)
C5—C6—H6B	109.2	C22—C23—C23'	120.0 (2)
H6A—C6—H6B	107.9	C22—C23—C24	117.8 (2)
C6—C7—C8	112.4 (2)	C23'—C23—C24	122.1 (2)
C6—C7—H7A	109.1	O23"—C23'—C23	124.5 (2)
C8—C7—H7A	109.1	O23"—C23'—C23"	115.6 (3)
C6—C7—H7B	109.1	C23—C23'—C23"	119.8 (3)
C8—C7—H7B	109.1	C23'—C23"—H23A	109.5
H7A—C7—H7B	107.9	C23'—C23"—H23B	109.5
C14—C8—C7	111.0 (2)	H23A—C23"—H23B	109.5
C14—C8—C9	107.50 (16)	C23'—C23"—H23C	109.5
C7—C8—C9	111.08 (18)	H23A—C23"—H23C	109.5
C14—C8—H8A	109.1	H23B—C23"—H23C	109.5
C7—C8—H8A	109.1	C23—C24—C25	114.32 (19)
C9—C8—H8A	109.1	C23—C24—H24A	108.7
C11—C9—C10	114.01 (19)	C25—C24—H24A	108.7
C11—C9—C8	111.82 (17)	C23—C24—H24B	108.7
C10—C9—C8	111.91 (16)	C25—C24—H24B	108.7
C11—C9—H9A	106.1	H24A—C24—H24B	107.6
C10—C9—H9A	106.1	C26—C25—C27	110.7 (2)
C8—C9—H9A	106.1	C26—C25—C24	111.7 (3)
C19—C10—C1	107.0 (2)	C27—C25—C24	109.8 (2)
C19—C10—C5	110.5 (2)	C26—C25—H25A	108.2
C1—C10—C5	107.7 (2)	C27—C25—H25A	108.2
C19—C10—C9	111.0 (2)	C24—C25—H25A	108.2
C1—C10—C9	111.74 (17)	O26'—C26—C25	109.3 (3)
C5—C10—C9	108.9 (2)	O26'—C26—H26A	109.8
C9—C11—C12	111.8 (2)	C25—C26—H26A	109.8
C9—C11—H11A	109.3	O26'—C26—H26B	109.8
C12—C11—H11A	109.3	C25—C26—H26B	109.8
C9—C11—H11B	109.3	H26A—C26—H26B	108.3
C12—C11—H11B	109.3	C25—C27—H27A	109.5
H11A—C11—H11B	107.9	C25—C27—H27B	109.5
C13—C12—C11	111.00 (17)	H27A—C27—H27B	109.5
C13—C12—H12A	109.4	C25—C27—H27C	109.5
C11—C12—H12A	109.4	H27A—C27—H27C	109.5
C13—C12—H12B	109.4	H27B—C27—H27C	109.5
C11—C12—H12B	109.4	C27'—O26'—C26	120.7 (3)
H12A—C12—H12B	108.0	O29'—C27'—O26'	120.2 (4)
C18—C13—C12	109.8 (2)	O29'—C27'—C28'	124.7 (5)
C18—C13—C14	113.43 (18)	O26'—C27'—C28'	114.7 (4)
C12—C13—C14	108.65 (17)	C27'—C28'—H28A	109.5
C18—C13—C17	111.93 (16)	C27'—C28'—H28B	109.5
C12—C13—C17	114.16 (16)	H28A—C28'—H28B	109.5
C14—C13—C17	98.46 (18)	C27'—C28'—H28C	109.5
C8—C14—C15	120.58 (18)	H28A—C28'—H28C	109.5
C8—C14—C13	114.92 (19)	H28B—C28'—H28C	109.5
C15—C14—C13	103.29 (17)
C10—C1—C2—C3	55.1 (3)	C18—C13—C14—C8	64.3 (2)
C1—C2—C3—O3'	67.2 (3)	C12—C13—C14—C8	−58.2 (2)
C1—C2—C3—C4	−50.8 (3)	C17—C13—C14—C8	−177.30 (16)
C4—C3—O3'—C4'	−114.0 (4)	C18—C13—C14—C15	−69.1 (2)
C2—C3—O3'—C4'	125.2 (3)	C12—C13—C14—C15	168.50 (18)
C3—O3'—C4'—O6'A	32.3 (11)	C17—C13—C14—C15	49.4 (2)
C3—O3'—C4'—O6'	−33.9 (9)	C8—C14—C15—C16	−169.2 (2)
C3—O3'—C4'—C5'	177.5 (3)	C13—C14—C15—C16	−39.2 (2)
O3'—C4'—O6'—O6'A	104.6 (6)	C14—C15—C16—O22'	127.6 (2)
C5'—C4'—O6'—O6'A	−109.0 (6)	C14—C15—C16—C17	13.2 (3)
O3'—C4'—O6'A—O6'	−107.9 (7)	O22'—C16—C17—C20	25.0 (2)
C5'—C4'—O6'A—O6'	109.3 (6)	C15—C16—C17—C20	144.02 (19)
O3'—C3—C4—C5	−68.0 (3)	O22'—C16—C17—C13	−101.79 (18)
C2—C3—C4—C5	50.0 (3)	C15—C16—C17—C13	17.3 (2)
C3—C4—C5—C6	−178.6 (2)	C18—C13—C17—C20	−36.0 (3)
C3—C4—C5—C10	−52.0 (3)	C12—C13—C17—C20	89.6 (2)
C4—C5—C6—C7	71.2 (3)	C14—C13—C17—C20	−155.52 (17)
C10—C5—C6—C7	−56.5 (3)	C18—C13—C17—C16	79.4 (2)
C5—C6—C7—C8	54.1 (4)	C12—C13—C17—C16	−155.0 (2)
C6—C7—C8—C14	−172.2 (2)	C14—C13—C17—C16	−40.14 (19)
C6—C7—C8—C9	−52.6 (3)	C16—C17—C20—C22	−26.4 (2)
C14—C8—C9—C11	−54.4 (3)	C13—C17—C20—C22	89.3 (2)
C7—C8—C9—C11	−176.1 (2)	C16—C17—C20—C21	89.4 (2)
C14—C8—C9—C10	176.3 (2)	C13—C17—C20—C21	−154.89 (18)
C7—C8—C9—C10	54.6 (3)	C17—C20—C22—O22'	19.6 (2)
C2—C1—C10—C19	−172.8 (2)	C21—C20—C22—O22'	−98.4 (2)
C2—C1—C10—C5	−54.0 (3)	C17—C20—C22—C23	−164.4 (2)
C2—C1—C10—C9	65.5 (3)	C21—C20—C22—C23	77.6 (3)
C4—C5—C10—C19	168.00 (19)	C23—C22—O22'—C16	179.75 (19)
C6—C5—C10—C19	−65.3 (2)	C20—C22—O22'—C16	−3.7 (2)
C4—C5—C10—C1	51.5 (2)	C15—C16—O22'—C22	−129.7 (2)
C6—C5—C10—C1	178.2 (2)	C17—C16—O22'—C22	−13.7 (2)
C4—C5—C10—C9	−69.8 (2)	O22'—C22—C23—C23'	−175.10 (19)
C6—C5—C10—C9	56.9 (2)	C20—C22—C23—C23'	9.2 (3)
C11—C9—C10—C19	−62.6 (3)	O22'—C22—C23—C24	3.9 (3)
C8—C9—C10—C19	65.6 (3)	C20—C22—C23—C24	−171.8 (2)
C11—C9—C10—C1	56.8 (3)	C22—C23—C23'—O23"	−0.2 (4)
C8—C9—C10—C1	−175.1 (2)	C24—C23—C23'—O23"	−179.2 (2)
C11—C9—C10—C5	175.58 (19)	C22—C23—C23'—C23"	177.1 (3)
C8—C9—C10—C5	−56.3 (3)	C24—C23—C23'—C23"	−1.9 (4)
C10—C9—C11—C12	−175.58 (18)	C22—C23—C24—C25	72.8 (3)
C8—C9—C11—C12	56.2 (3)	C23'—C23—C24—C25	−108.2 (3)
C9—C11—C12—C13	−56.4 (3)	C23—C24—C25—C26	63.4 (3)
C11—C12—C13—C18	−69.4 (3)	C23—C24—C25—C27	−173.3 (3)
C11—C12—C13—C14	55.2 (3)	C27—C25—C26—O26'	61.1 (4)
C11—C12—C13—C17	163.9 (2)	C24—C25—C26—O26'	−176.2 (2)
C7—C8—C14—C15	−56.8 (3)	C25—C26—O26'—C27'	115.6 (4)
C9—C8—C14—C15	−178.4 (2)	C26—O26'—C27'—O29'	−5.1 (8)
C7—C8—C14—C13	178.56 (18)	C26—O26'—C27'—C28'	−178.0 (4)
C9—C8—C14—C13	56.9 (2)