20-Oxopregn-5-ene-3β,16α-diyl di­acetate

The title compound, C₂₅H₃₆O₅, has two independent mol­ecules in the asymmetric unit with similar geometry. The main difference between the two mol­ecules relates to the conformation of the 17β-methyl ketone and 3β-acetoxy groups, the latter being disordered in one of the mol­ecules. The five-membered ring adopts an unusual 13β-envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.043
• wR factor = 0.124
• Data-to-parameter ratio = 8.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_213  Alert C Atom C21     has ADP max/min Ratio ...........       3.60 prolate

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           71.91
         From the CIF: _reflns_number_total               4918
         Count of symmetry unique reflns         4936
         Completeness (_total/calc)             99.64%
         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
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

20-Oxopregn-5-ene-3β,16α-diyl diacetate

Crystal data

C25H36O5	F(000) = 904
Mr = 416.54	Dx = 1.173 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54180 Å
a = 14.892 (2) Å	Cell parameters from 25 reflections
b = 9.375 (3) Å	θ = 10.2–29.2°
c = 17.119 (7) Å	µ = 0.64 mm^−1
β = 99.18 (2)°	T = 293 K
V = 2359.3 (13) Å^3	Prism, colourless
Z = 4	0.55 × 0.24 × 0.22 mm

Data collection

Enraf-Nonius MACH3 diffractometer	Rint = 0.034
Graphite monochromator	θmax = 71.9°, θmin = 4.3°
profile data from ω–2θ scans	h = −18→18
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.831, Tmax = 0.868	l = −21→5
7913 measured reflections	3 standard reflections every 180 min
4918 independent reflections	intensity decay: 5.7%
4607 reflections with I > 2σ(I)

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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.3449P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4918 reflections	Δρmax = 0.27 e Å^−3
559 parameters	Δρmin = −0.21 e Å^−3
19 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.26743 (14)	1.0714 (3)	−0.15071 (12)	0.0402 (5)
H1	0.2153	1.0711	−0.1232	0.048*
H2	0.2929	1.1669	−0.1467	0.048*
C2	0.23502 (16)	1.0375 (3)	−0.23795 (13)	0.0473 (5)
H3	0.2053	0.9451	−0.2426	0.057*
H4	0.1912	1.1086	−0.2607	0.057*
C3	0.31479 (17)	1.0361 (3)	−0.28261 (13)	0.0492 (6)
H5	0.3402	1.1324	−0.2836	0.059*
C4	0.38824 (15)	0.9331 (3)	−0.24550 (12)	0.0466 (5)
H6	0.3661	0.8362	−0.2545	0.056*
H7	0.4412	0.9439	−0.2715	0.056*
C5	0.41630 (14)	0.9564 (3)	−0.15757 (12)	0.0384 (4)
C6	0.50353 (14)	0.9618 (3)	−0.12594 (13)	0.0449 (5)
H8	0.5461	0.9575	−0.1602	0.054*
C7	0.53864 (14)	0.9745 (3)	−0.03917 (13)	0.0467 (6)
H9	0.5633	1.0695	−0.0282	0.056*
H10	0.5877	0.9067	−0.0249	0.056*
C8	0.46513 (13)	0.9473 (3)	0.01179 (11)	0.0366 (4)
H11	0.4532	0.8446	0.0125	0.044*
C9	0.37675 (13)	1.0243 (3)	−0.02481 (11)	0.0362 (4)
H12	0.3937	1.1238	−0.0321	0.043*
C10	0.33931 (13)	0.9664 (2)	−0.10865 (11)	0.0350 (4)
C11	0.30510 (14)	1.0276 (3)	0.03064 (12)	0.0446 (5)
H13	0.2574	1.0939	0.0093	0.054*
H14	0.2778	0.9337	0.0311	0.054*
C12	0.34218 (16)	1.0711 (3)	0.11631 (13)	0.0489 (6)
H15	0.3605	1.1705	0.1176	0.059*
H16	0.2946	1.0608	0.1486	0.059*
C13	0.42348 (15)	0.9787 (3)	0.15022 (12)	0.0414 (5)
C14	0.49571 (14)	0.9976 (3)	0.09621 (12)	0.0390 (5)
H17	0.5071	1.1003	0.0934	0.047*
C15	0.58139 (16)	0.9316 (3)	0.14376 (14)	0.0516 (6)
H18	0.6357	0.9768	0.1307	0.062*
H19	0.5842	0.8301	0.1333	0.062*
C16	0.57225 (17)	0.9591 (3)	0.23074 (14)	0.0491 (5)
H20	0.5755	0.8687	0.2597	0.059*
C17	0.47905 (16)	1.0283 (3)	0.23044 (12)	0.0494 (6)
H21	0.4875	1.1316	0.2266	0.059*
C18	0.39438 (19)	0.8229 (3)	0.15759 (16)	0.0539 (6)
H22	0.3721	0.7853	0.1059	0.065*
H23	0.3471	0.8181	0.1897	0.065*
H24	0.4456	0.7676	0.1818	0.065*
C19	0.29632 (16)	0.8175 (3)	−0.10503 (13)	0.0437 (5)
H25	0.2877	0.7751	−0.1567	0.052*
H26	0.2386	0.8263	−0.0872	0.052*
H27	0.3359	0.7583	−0.0689	0.052*
C20	0.4319 (2)	1.0023 (5)	0.30185 (15)	0.0715 (9)
C21	0.4801 (4)	0.9208 (13)	0.3698 (3)	0.199 (5)
H28	0.5346	0.9705	0.3919	0.299*
H29	0.4955	0.8279	0.3523	0.299*
H30	0.4414	0.9109	0.4093	0.299*
C22	0.7234 (2)	1.0019 (4)	0.29556 (19)	0.0670 (8)
C23	0.7868 (3)	1.1103 (5)	0.3367 (3)	0.1005 (15)
H31	0.8340	1.0634	0.3723	0.121*
H32	0.7539	1.1735	0.3661	0.121*
H33	0.8133	1.1639	0.2984	0.121*
C24	0.3232 (3)	1.0304 (6)	−0.42116 (17)	0.0830 (12)
C25	0.2799 (4)	0.9711 (9)	−0.49828 (19)	0.126 (2)
H34	0.2160	0.9923	−0.5065	0.151*
H35	0.2884	0.8696	−0.4983	0.151*
H36	0.3071	1.0131	−0.5400	0.151*
O3	0.27999 (13)	0.9902 (3)	−0.36243 (10)	0.0641 (6)
O16	0.64080 (13)	1.0570 (2)	0.26956 (11)	0.0585 (5)
O20	0.35677 (19)	1.0427 (4)	0.30273 (13)	0.1002 (10)
O22	0.74277 (18)	0.8810 (3)	0.2837 (2)	0.1015 (10)
O24	0.3903 (3)	1.1018 (5)	−0.41074 (18)	0.1195 (13)
O3'	1.01408 (16)	1.0022 (3)	1.19400 (10)	0.0700 (6)
O16'	0.85990 (15)	0.8047 (3)	0.53584 (10)	0.0627 (5)
O20'	0.6692 (2)	1.0199 (5)	0.50838 (17)	0.1202 (13)
O22'	0.9502 (2)	0.9442 (4)	0.47721 (15)	0.0928 (9)
C1'	0.83948 (16)	0.9112 (4)	1.01638 (12)	0.0523 (7)
H1'	0.7737	0.9201	1.0077	0.063*
H2'	0.8540	0.8114	1.0102	0.063*
C2'	0.87613 (17)	0.9567 (4)	1.10112 (13)	0.0584 (7)
H3'	0.8584	1.0544	1.1094	0.070*
H4'	0.8506	0.8963	1.1380	0.070*
C3'	0.97846 (17)	0.9447 (3)	1.11596 (13)	0.0521 (6)
H5'	0.9962	0.8444	1.1133	0.062*
C4'	1.02101 (16)	1.0306 (4)	1.05689 (13)	0.0516 (6)
H6'	1.0123	1.1313	1.0661	0.062*
H7'	1.0859	1.0122	1.0647	0.062*
C5'	0.98088 (14)	0.9951 (3)	0.97280 (13)	0.0415 (5)
C6'	1.03424 (15)	0.9629 (3)	0.91967 (14)	0.0482 (6)
H8'	1.0965	0.9591	0.9375	0.058*
C7'	1.00259 (15)	0.9326 (4)	0.83432 (14)	0.0521 (6)
H9'	1.0081	0.8312	0.8249	0.062*
H10'	1.0414	0.9825	0.8029	0.062*
C8'	0.90374 (14)	0.9785 (3)	0.80781 (12)	0.0403 (5)
H11'	0.9017	1.0828	0.8043	0.048*
C9'	0.84546 (13)	0.9306 (3)	0.86991 (11)	0.0368 (4)
H12'	0.8550	0.8276	0.8766	0.044*
C10'	0.87759 (14)	0.9988 (3)	0.95212 (12)	0.0386 (5)
C11'	0.74330 (14)	0.9517 (4)	0.84108 (12)	0.0474 (6)
H13'	0.7296	1.0527	0.8426	0.057*
H14'	0.7098	0.9040	0.8776	0.057*
C12'	0.70933 (15)	0.8957 (4)	0.75715 (13)	0.0524 (7)
H15'	0.7137	0.7925	0.7568	0.063*
H16'	0.6460	0.9216	0.7414	0.063*
C13'	0.76543 (16)	0.9580 (3)	0.69870 (12)	0.0471 (6)
C14'	0.86516 (15)	0.9174 (3)	0.72774 (12)	0.0426 (5)
H17'	0.8662	0.8135	0.7340	0.051*
C15'	0.91405 (19)	0.9495 (4)	0.65724 (14)	0.0586 (7)
H18'	0.9358	1.0472	0.6591	0.070*
H19'	0.9652	0.8856	0.6567	0.070*
C16'	0.8408 (2)	0.9251 (4)	0.58459 (14)	0.0575 (7)
H20'	0.8326	1.0120	0.5524	0.069*
C17'	0.75196 (18)	0.8882 (4)	0.61512 (13)	0.0556 (7)
H21'	0.7505	0.7846	0.6223	0.067*
C18'	0.7514 (3)	1.1203 (4)	0.68946 (18)	0.0677 (8)
H22'	0.6884	1.1399	0.6704	0.081*
H23'	0.7879	1.1563	0.6524	0.081*
H24'	0.7691	1.1658	0.7398	0.081*
C19'	0.84553 (18)	1.1545 (3)	0.95438 (11)	0.0562 (7)
H25'	0.8785	1.2013	1.0000	0.067*
H26'	0.7817	1.1565	0.9571	0.067*
H27'	0.8564	1.2030	0.9074	0.067*
C20'	0.66675 (16)	0.9300 (3)	0.55996 (10)	0.0764 (10)
C21'	0.57991 (14)	0.8635 (3)	0.57203 (11)	0.1007 (17)
H28'	0.5339	0.9356	0.5701	0.121*
H29'	0.5878	0.8171	0.6227	0.121*
H30'	0.5617	0.7944	0.5311	0.121*
C22'	0.9147 (2)	0.8312 (4)	0.48243 (15)	0.0612 (7)
C23'	0.9240 (3)	0.7050 (5)	0.4318 (2)	0.0845 (11)
H31'	0.9568	0.7316	0.3901	0.101*
H32'	0.8647	0.6708	0.4094	0.101*
H33'	0.9566	0.6311	0.4632	0.101*
C24a'	1.0321 (3)	0.9168 (5)	1.25419 (19)	0.0617 (12)	0.721 (5)
C25a'	1.0745 (6)	0.9923 (10)	1.3274 (3)	0.088 (2)	0.721 (5)
H34a'	1.1346	1.0230	1.3216	0.105*	0.721 (5)
H35a'	1.0781	0.9288	1.3717	0.105*	0.721 (5)
H36a'	1.0383	1.0738	1.3360	0.105*	0.721 (5)
O24a'	1.0068 (3)	0.7943 (4)	1.24975 (19)	0.0952 (14)	0.721 (5)
C24b'	1.0870 (6)	0.9461 (13)	1.2355 (5)	0.065 (3)*	0.279 (5)
C25b'	1.1039 (13)	0.994 (3)	1.3190 (7)	0.076 (6)*	0.279 (5)
H34b'	1.1374	0.9222	1.3513	0.091*	0.279 (5)
H35b'	1.0468	1.0104	1.3369	0.091*	0.279 (5)
H36b'	1.1383	1.0812	1.3230	0.091*	0.279 (5)
O24b'	1.1362 (7)	0.8763 (13)	1.2036 (6)	0.101 (4)*	0.279 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0351 (9)	0.0473 (13)	0.0383 (10)	0.0019 (9)	0.0057 (8)	0.0036 (9)
C2	0.0439 (11)	0.0577 (15)	0.0387 (10)	0.0025 (12)	0.0015 (8)	0.0055 (11)
C3	0.0528 (12)	0.0579 (15)	0.0369 (10)	0.0003 (12)	0.0076 (9)	0.0065 (11)
C4	0.0449 (11)	0.0588 (15)	0.0366 (10)	0.0012 (11)	0.0080 (8)	−0.0004 (10)
C5	0.0382 (10)	0.0420 (12)	0.0359 (9)	−0.0001 (9)	0.0085 (8)	0.0000 (9)
C6	0.0365 (10)	0.0598 (15)	0.0404 (10)	0.0022 (11)	0.0119 (8)	−0.0004 (11)
C7	0.0322 (9)	0.0636 (16)	0.0440 (11)	0.0001 (11)	0.0053 (8)	−0.0015 (11)
C8	0.0338 (9)	0.0396 (11)	0.0357 (9)	−0.0005 (9)	0.0034 (7)	−0.0007 (9)
C9	0.0363 (9)	0.0376 (11)	0.0347 (9)	0.0004 (9)	0.0053 (7)	−0.0005 (8)
C10	0.0327 (9)	0.0374 (11)	0.0351 (9)	−0.0013 (9)	0.0063 (7)	0.0010 (8)
C11	0.0379 (10)	0.0585 (15)	0.0374 (10)	0.0065 (11)	0.0060 (8)	−0.0015 (10)
C12	0.0479 (12)	0.0607 (16)	0.0381 (11)	0.0105 (12)	0.0074 (9)	−0.0065 (11)
C13	0.0444 (11)	0.0442 (13)	0.0350 (9)	0.0019 (10)	0.0043 (8)	−0.0022 (9)
C14	0.0392 (10)	0.0391 (11)	0.0371 (10)	−0.0017 (9)	0.0016 (8)	−0.0021 (9)
C15	0.0450 (11)	0.0606 (16)	0.0452 (11)	0.0068 (12)	−0.0054 (9)	−0.0040 (12)
C16	0.0524 (12)	0.0453 (13)	0.0449 (11)	0.0012 (11)	−0.0063 (9)	−0.0020 (10)
C17	0.0552 (12)	0.0544 (15)	0.0361 (10)	0.0046 (12)	−0.0006 (9)	−0.0040 (11)
C18	0.0593 (14)	0.0526 (15)	0.0495 (12)	−0.0086 (13)	0.0077 (11)	0.0062 (12)
C19	0.0466 (11)	0.0427 (12)	0.0415 (10)	−0.0083 (10)	0.0066 (9)	0.0007 (10)
C20	0.0761 (18)	0.100 (3)	0.0371 (11)	0.010 (2)	0.0047 (11)	−0.0027 (15)
C21	0.115 (3)	0.421 (15)	0.065 (2)	0.088 (6)	0.026 (2)	0.105 (5)
C22	0.0610 (16)	0.0562 (18)	0.0735 (18)	−0.0009 (14)	−0.0206 (14)	0.0077 (15)
C23	0.083 (2)	0.078 (3)	0.119 (3)	−0.008 (2)	−0.048 (2)	0.005 (2)
C24	0.084 (2)	0.122 (3)	0.0474 (14)	0.025 (3)	0.0233 (14)	0.0204 (19)
C25	0.132 (3)	0.208 (7)	0.0393 (15)	0.038 (5)	0.0154 (18)	0.002 (3)
O3	0.0660 (11)	0.0900 (17)	0.0351 (8)	0.0057 (12)	0.0044 (7)	0.0050 (9)
O16	0.0627 (10)	0.0487 (11)	0.0549 (10)	0.0008 (9)	−0.0187 (8)	−0.0016 (8)
O20	0.0988 (18)	0.147 (3)	0.0599 (12)	0.041 (2)	0.0290 (12)	0.0137 (17)
O22	0.0680 (14)	0.0635 (17)	0.159 (3)	0.0096 (13)	−0.0247 (16)	−0.0088 (17)
O24	0.123 (2)	0.163 (4)	0.0847 (18)	−0.007 (3)	0.0516 (18)	0.033 (2)
O3'	0.0925 (14)	0.0726 (15)	0.0381 (9)	−0.0007 (12)	−0.0106 (8)	−0.0027 (9)
O16'	0.0817 (13)	0.0684 (13)	0.0424 (8)	−0.0016 (11)	0.0237 (8)	−0.0074 (9)
O20'	0.110 (2)	0.167 (4)	0.0743 (16)	0.004 (2)	−0.0135 (14)	0.048 (2)
O22'	0.1130 (19)	0.103 (2)	0.0750 (15)	−0.0253 (19)	0.0524 (14)	−0.0179 (15)
C1'	0.0434 (11)	0.0793 (19)	0.0352 (10)	−0.0086 (12)	0.0101 (8)	0.0020 (12)
C2'	0.0583 (14)	0.083 (2)	0.0357 (10)	−0.0013 (15)	0.0120 (9)	−0.0014 (13)
C3'	0.0585 (13)	0.0586 (16)	0.0362 (10)	−0.0001 (13)	−0.0012 (9)	−0.0022 (11)
C4'	0.0452 (11)	0.0652 (17)	0.0416 (11)	−0.0065 (12)	−0.0013 (9)	−0.0007 (12)
C5'	0.0384 (10)	0.0469 (13)	0.0385 (10)	−0.0037 (9)	0.0045 (8)	0.0029 (9)
C6'	0.0329 (9)	0.0648 (17)	0.0468 (11)	−0.0010 (11)	0.0062 (8)	0.0036 (12)
C7'	0.0379 (10)	0.0752 (19)	0.0462 (11)	−0.0002 (12)	0.0160 (9)	−0.0022 (12)
C8'	0.0384 (10)	0.0481 (13)	0.0366 (9)	−0.0020 (10)	0.0127 (8)	−0.0001 (9)
C9'	0.0346 (9)	0.0436 (12)	0.0333 (9)	0.0002 (9)	0.0091 (7)	−0.0006 (9)
C10'	0.0370 (10)	0.0456 (13)	0.0335 (9)	0.0017 (9)	0.0069 (7)	−0.0014 (9)
C11'	0.0358 (10)	0.0738 (17)	0.0341 (9)	−0.0002 (12)	0.0102 (7)	−0.0043 (11)
C12'	0.0386 (11)	0.083 (2)	0.0355 (10)	−0.0050 (12)	0.0068 (8)	−0.0042 (12)
C13'	0.0477 (11)	0.0621 (16)	0.0321 (10)	0.0048 (12)	0.0083 (8)	−0.0011 (11)
C14'	0.0434 (11)	0.0510 (14)	0.0360 (10)	0.0005 (10)	0.0146 (8)	−0.0020 (10)
C15'	0.0590 (14)	0.082 (2)	0.0393 (11)	−0.0113 (15)	0.0211 (10)	−0.0051 (13)
C16'	0.0725 (16)	0.0660 (18)	0.0372 (11)	−0.0010 (15)	0.0189 (11)	−0.0019 (12)
C17'	0.0617 (14)	0.0739 (19)	0.0315 (10)	−0.0001 (15)	0.0085 (9)	−0.0035 (12)
C18'	0.084 (2)	0.065 (2)	0.0526 (14)	0.0188 (17)	0.0055 (14)	0.0032 (14)
C19'	0.0614 (15)	0.0556 (16)	0.0491 (13)	0.0144 (13)	0.0007 (11)	−0.0135 (12)
C20'	0.0744 (18)	0.118 (3)	0.0349 (11)	0.005 (2)	0.0019 (11)	0.0021 (16)
C21'	0.0643 (18)	0.180 (5)	0.0535 (16)	−0.002 (3)	−0.0054 (13)	0.006 (2)
C22'	0.0660 (16)	0.081 (2)	0.0386 (11)	0.0047 (17)	0.0149 (11)	−0.0033 (13)
C23'	0.099 (3)	0.098 (3)	0.0621 (18)	0.007 (2)	0.0289 (17)	−0.0191 (19)
C24a'	0.073 (3)	0.072 (3)	0.0379 (17)	0.015 (2)	0.0032 (16)	0.0011 (17)
C25a'	0.092 (5)	0.134 (7)	0.0320 (18)	−0.008 (5)	−0.006 (2)	0.000 (3)
O24a'	0.166 (4)	0.067 (2)	0.0516 (16)	0.013 (3)	0.0132 (19)	0.0066 (15)

Geometric parameters (Å, º)

C1—C2	1.528 (3)	O16'—C22'	1.342 (3)
C1—C10	1.545 (3)	O16'—C16'	1.458 (4)
C1—H1	0.9700	O20'—C20'	1.226 (4)
C1—H2	0.9700	O22'—C22'	1.194 (5)
C2—C3	1.512 (3)	C1'—C2'	1.527 (3)
C2—H3	0.9700	C1'—C10'	1.551 (3)
C2—H4	0.9700	C1'—H1'	0.9700
C3—O3	1.448 (3)	C1'—H2'	0.9700
C3—C4	1.520 (4)	C2'—C3'	1.509 (4)
C3—H5	0.9800	C2'—H3'	0.9700
C4—C5	1.512 (3)	C2'—H4'	0.9700
C4—H6	0.9700	C3'—C4'	1.509 (4)
C4—H7	0.9700	C3'—H5'	0.9800
C5—C6	1.326 (3)	C4'—C5'	1.505 (3)
C5—C10	1.527 (3)	C4'—H6'	0.9700
C6—C7	1.499 (3)	C4'—H7'	0.9700
C6—H8	0.9300	C5'—C6'	1.334 (3)
C7—C8	1.526 (3)	C5'—C10'	1.523 (3)
C7—H9	0.9700	C6'—C7'	1.489 (3)
C7—H10	0.9700	C6'—H8'	0.9300
C8—C14	1.519 (3)	C7'—C8'	1.531 (3)
C8—C9	1.543 (3)	C7'—H9'	0.9700
C8—H11	0.9800	C7'—H10'	0.9700
C9—C11	1.537 (3)	C8'—C14'	1.512 (3)
C9—C10	1.552 (3)	C8'—C9'	1.543 (3)
C9—H12	0.9800	C8'—H11'	0.9800
C10—C19	1.542 (3)	C9'—C11'	1.536 (3)
C11—C12	1.537 (3)	C9'—C10'	1.551 (3)
C11—H13	0.9700	C9'—H12'	0.9800
C11—H14	0.9700	C10'—C19'	1.538 (3)
C12—C13	1.526 (3)	C11'—C12'	1.537 (3)
C12—H15	0.9700	C11'—H13'	0.9700
C12—H16	0.9700	C11'—H14'	0.9700
C13—C18	1.535 (4)	C12'—C13'	1.519 (3)
C13—C14	1.536 (3)	C12'—H15'	0.9700
C13—C17	1.557 (3)	C12'—H16'	0.9700
C14—C15	1.530 (3)	C13'—C14'	1.537 (3)
C14—H17	0.9800	C13'—C18'	1.541 (5)
C15—C16	1.539 (4)	C13'—C17'	1.557 (3)
C15—H18	0.9700	C14'—C15'	1.535 (3)
C15—H19	0.9700	C14'—H17'	0.9800
C16—O16	1.452 (3)	C15'—C16'	1.535 (4)
C16—C17	1.531 (4)	C15'—H18'	0.9700
C16—H20	0.9800	C15'—H19'	0.9700
C17—C20	1.523 (4)	C16'—C17'	1.537 (4)
C17—H21	0.9800	C16'—H20'	0.9800
C18—H22	0.9600	C17'—C20'	1.508 (3)
C18—H23	0.9600	C17'—H21'	0.9800
C18—H24	0.9600	C18'—H22'	0.9600
C19—H25	0.9600	C18'—H23'	0.9600
C19—H26	0.9600	C18'—H24'	0.9600
C19—H27	0.9600	C19'—H25'	0.9600
C20—O20	1.184 (4)	C19'—H26'	0.9600
C20—C21	1.478 (6)	C19'—H27'	0.9600
C21—H28	0.9600	C20'—C21'	1.480 (3)
C21—H29	0.9600	C21'—H28'	0.9600
C21—H30	0.9600	C21'—H29'	0.9600
C22—O22	1.195 (5)	C21'—H30'	0.9600
C22—O16	1.343 (4)	C22'—C23'	1.486 (5)
C22—C23	1.485 (5)	C23'—H31'	0.9600
C23—H31	0.9600	C23'—H32'	0.9600
C23—H32	0.9600	C23'—H33'	0.9600
C23—H33	0.9600	C24a'—O24a'	1.208 (5)
C24—O24	1.192 (6)	C24a'—C25a'	1.489 (5)
C24—O3	1.332 (4)	C25a'—H34a'	0.9600
C24—C25	1.482 (6)	C25a'—H35a'	0.9600
C25—H34	0.9600	C25a'—H36a'	0.9600
C25—H35	0.9600	C24b'—O24b'	1.179 (7)
C25—H36	0.9600	C24b'—C25b'	1.482 (7)
O3'—C24a'	1.298 (4)	C25b'—H34b'	0.9600
O3'—C24b'	1.310 (6)	C25b'—H35b'	0.9600
O3'—C3'	1.459 (3)	C25b'—H36b'	0.9600
C2—C1—C10	114.2 (2)	C22'—O16'—C16'	116.3 (3)
C2—C1—H1	108.7	C2'—C1'—C10'	114.2 (2)
C10—C1—H1	108.7	C2'—C1'—H1'	108.7
C2—C1—H2	108.7	C10'—C1'—H1'	108.7
C10—C1—H2	108.7	C2'—C1'—H2'	108.7
H1—C1—H2	107.6	C10'—C1'—H2'	108.7
C3—C2—C1	110.17 (18)	H1'—C1'—H2'	107.6
C3—C2—H3	109.6	C3'—C2'—C1'	109.7 (2)
C1—C2—H3	109.6	C3'—C2'—H3'	109.7
C3—C2—H4	109.6	C1'—C2'—H3'	109.7
C1—C2—H4	109.6	C3'—C2'—H4'	109.7
H3—C2—H4	108.1	C1'—C2'—H4'	109.7
O3—C3—C2	106.74 (19)	H3'—C2'—H4'	108.2
O3—C3—C4	109.3 (2)	O3'—C3'—C2'	109.7 (2)
C2—C3—C4	111.4 (2)	O3'—C3'—C4'	106.7 (2)
O3—C3—H5	109.8	C2'—C3'—C4'	111.6 (2)
C2—C3—H5	109.8	O3'—C3'—H5'	109.6
C4—C3—H5	109.8	C2'—C3'—H5'	109.6
C5—C4—C3	113.0 (2)	C4'—C3'—H5'	109.6
C5—C4—H6	109.0	C5'—C4'—C3'	112.2 (2)
C3—C4—H6	109.0	C5'—C4'—H6'	109.2
C5—C4—H7	109.0	C3'—C4'—H6'	109.2
C3—C4—H7	109.0	C5'—C4'—H7'	109.2
H6—C4—H7	107.8	C3'—C4'—H7'	109.2
C6—C5—C4	120.61 (19)	H6'—C4'—H7'	107.9
C6—C5—C10	123.09 (19)	C6'—C5'—C4'	120.9 (2)
C4—C5—C10	116.25 (17)	C6'—C5'—C10'	122.41 (19)
C5—C6—C7	124.88 (19)	C4'—C5'—C10'	116.71 (19)
C5—C6—H8	117.6	C5'—C6'—C7'	125.6 (2)
C7—C6—H8	117.6	C5'—C6'—H8'	117.2
C6—C7—C8	112.62 (17)	C7'—C6'—H8'	117.2
C6—C7—H9	109.1	C6'—C7'—C8'	112.07 (19)
C8—C7—H9	109.1	C6'—C7'—H9'	109.2
C6—C7—H10	109.1	C8'—C7'—H9'	109.2
C8—C7—H10	109.1	C6'—C7'—H10'	109.2
H9—C7—H10	107.8	C8'—C7'—H10'	109.2
C14—C8—C7	111.00 (17)	H9'—C7'—H10'	107.9
C14—C8—C9	110.36 (17)	C14'—C8'—C7'	111.74 (19)
C7—C8—C9	109.43 (17)	C14'—C8'—C9'	109.89 (17)
C14—C8—H11	108.7	C7'—C8'—C9'	109.49 (18)
C7—C8—H11	108.7	C14'—C8'—H11'	108.6
C9—C8—H11	108.7	C7'—C8'—H11'	108.6
C11—C9—C8	112.94 (17)	C9'—C8'—H11'	108.6
C11—C9—C10	113.32 (16)	C11'—C9'—C8'	112.23 (17)
C8—C9—C10	111.67 (17)	C11'—C9'—C10'	112.64 (17)
C11—C9—H12	106.1	C8'—C9'—C10'	112.28 (17)
C8—C9—H12	106.1	C11'—C9'—H12'	106.4
C10—C9—H12	106.1	C8'—C9'—H12'	106.4
C5—C10—C19	108.61 (19)	C10'—C9'—H12'	106.4
C5—C10—C1	107.99 (17)	C5'—C10'—C19'	108.8 (2)
C19—C10—C1	109.54 (17)	C5'—C10'—C9'	110.82 (17)
C5—C10—C9	109.78 (16)	C19'—C10'—C9'	111.24 (17)
C19—C10—C9	111.68 (17)	C5'—C10'—C1'	107.06 (18)
C1—C10—C9	109.18 (18)	C19'—C10'—C1'	109.5 (2)
C12—C11—C9	114.55 (18)	C9'—C10'—C1'	109.29 (19)
C12—C11—H13	108.6	C9'—C11'—C12'	114.70 (18)
C9—C11—H13	108.6	C9'—C11'—H13'	108.6
C12—C11—H14	108.6	C12'—C11'—H13'	108.6
C9—C11—H14	108.6	C9'—C11'—H14'	108.6
H13—C11—H14	107.6	C12'—C11'—H14'	108.6
C13—C12—C11	110.8 (2)	H13'—C11'—H14'	107.6
C13—C12—H15	109.5	C13'—C12'—C11'	110.6 (2)
C11—C12—H15	109.5	C13'—C12'—H15'	109.5
C13—C12—H16	109.5	C11'—C12'—H15'	109.5
C11—C12—H16	109.5	C13'—C12'—H16'	109.5
H15—C12—H16	108.1	C11'—C12'—H16'	109.5
C12—C13—C18	110.7 (2)	H15'—C12'—H16'	108.1
C12—C13—C14	107.13 (19)	C12'—C13'—C14'	107.26 (19)
C18—C13—C14	113.2 (2)	C12'—C13'—C18'	111.5 (3)
C12—C13—C17	116.3 (2)	C14'—C13'—C18'	112.7 (3)
C18—C13—C17	109.2 (2)	C12'—C13'—C17'	116.1 (2)
C14—C13—C17	99.88 (17)	C14'—C13'—C17'	99.77 (19)
C8—C14—C15	118.59 (19)	C18'—C13'—C17'	109.0 (2)
C8—C14—C13	113.84 (17)	C8'—C14'—C15'	118.6 (2)
C15—C14—C13	103.74 (18)	C8'—C14'—C13'	114.05 (18)
C8—C14—H17	106.6	C15'—C14'—C13'	104.61 (19)
C15—C14—H17	106.6	C8'—C14'—H17'	106.2
C13—C14—H17	106.6	C15'—C14'—H17'	106.2
C14—C15—C16	104.6 (2)	C13'—C14'—H17'	106.2
C14—C15—H18	110.8	C16'—C15'—C14'	104.1 (2)
C16—C15—H18	110.8	C16'—C15'—H18'	110.9
C14—C15—H19	110.8	C14'—C15'—H18'	110.9
C16—C15—H19	110.8	C16'—C15'—H19'	110.9
H18—C15—H19	108.9	C14'—C15'—H19'	110.9
O16—C16—C17	107.7 (2)	H18'—C15'—H19'	109.0
O16—C16—C15	112.6 (2)	O16'—C16'—C15'	113.6 (3)
C17—C16—C15	106.72 (18)	O16'—C16'—C17'	106.1 (2)
O16—C16—H20	109.9	C15'—C16'—C17'	107.27 (19)
C17—C16—H20	109.9	O16'—C16'—H20'	109.9
C15—C16—H20	109.9	C15'—C16'—H20'	109.9
C20—C17—C16	117.5 (2)	C17'—C16'—H20'	109.9
C20—C17—C13	114.3 (2)	C20'—C17'—C16'	114.4 (2)
C16—C17—C13	103.30 (19)	C20'—C17'—C13'	116.0 (2)
C20—C17—H21	107.0	C16'—C17'—C13'	103.1 (2)
C16—C17—H21	107.0	C20'—C17'—H21'	107.6
C13—C17—H21	107.0	C16'—C17'—H21'	107.6
C13—C18—H22	109.5	C13'—C17'—H21'	107.6
C13—C18—H23	109.5	C13'—C18'—H22'	109.5
H22—C18—H23	109.5	C13'—C18'—H23'	109.5
C13—C18—H24	109.5	H22'—C18'—H23'	109.5
H22—C18—H24	109.5	C13'—C18'—H24'	109.5
H23—C18—H24	109.5	H22'—C18'—H24'	109.5
C10—C19—H25	109.5	H23'—C18'—H24'	109.5
C10—C19—H26	109.5	C10'—C19'—H25'	109.5
H25—C19—H26	109.5	C10'—C19'—H26'	109.5
C10—C19—H27	109.5	H25'—C19'—H26'	109.5
H25—C19—H27	109.5	C10'—C19'—H27'	109.5
H26—C19—H27	109.5	H25'—C19'—H27'	109.5
O20—C20—C21	119.8 (3)	H26'—C19'—H27'	109.5
O20—C20—C17	121.1 (3)	O20'—C20'—C21'	121.2 (2)
C21—C20—C17	119.1 (3)	O20'—C20'—C17'	120.7 (3)
C20—C21—H28	109.5	C21'—C20'—C17'	118.03 (15)
C20—C21—H29	109.5	C20'—C21'—H28'	109.5
H28—C21—H29	109.5	C20'—C21'—H29'	109.5
C20—C21—H30	109.5	H28'—C21'—H29'	109.5
H28—C21—H30	109.5	C20'—C21'—H30'	109.5
H29—C21—H30	109.5	H28'—C21'—H30'	109.5
O22—C22—O16	122.8 (3)	H29'—C21'—H30'	109.5
O22—C22—C23	125.3 (3)	O22'—C22'—O16'	122.7 (3)
O16—C22—C23	111.9 (3)	O22'—C22'—C23'	125.4 (3)
C22—C23—H31	109.5	O16'—C22'—C23'	112.0 (3)
C22—C23—H32	109.5	C22'—C23'—H31'	109.5
H31—C23—H32	109.5	C22'—C23'—H32'	109.5
C22—C23—H33	109.5	H31'—C23'—H32'	109.5
H31—C23—H33	109.5	C22'—C23'—H33'	109.5
H32—C23—H33	109.5	H31'—C23'—H33'	109.5
O24—C24—O3	122.7 (3)	H32'—C23'—H33'	109.5
O24—C24—C25	125.4 (4)	O24a'—C24a'—O3'	120.9 (4)
O3—C24—C25	111.9 (4)	O24a'—C24a'—C25a'	126.3 (5)
C24—C25—H34	109.5	O3'—C24a'—C25a'	112.4 (4)
C24—C25—H35	109.5	O24b'—C24b'—O3'	119.5 (9)
H34—C25—H35	109.5	O24b'—C24b'—C25b'	126.5 (11)
C24—C25—H36	109.5	O3'—C24b'—C25b'	113.6 (11)
H34—C25—H36	109.5	C24a'—C25a'—H34a'	109.5
H35—C25—H36	109.5	C24a'—C25a'—H35a'	109.5
C24—O3—C3	119.0 (3)	H34a'—C25a'—H35a'	109.5
C22—O16—C16	116.7 (2)	C24b'—C25b'—H36b'	109.5
C24a'—O3'—C3'	119.9 (3)	H34b'—C25b'—H36b'	109.5
C24b'—O3'—C3'	119.8 (5)	H35b'—C25b'—H36b'	109.5
C10—C1—C2—C3	−58.1 (3)	C24b'—O3'—C3'—C4'	−92.4 (8)
C1—C2—C3—O3	174.7 (2)	C1'—C2'—C3'—O3'	174.1 (3)
C1—C2—C3—C4	55.4 (3)	C1'—C2'—C3'—C4'	56.1 (4)
O3—C3—C4—C5	−169.3 (2)	O3'—C3'—C4'—C5'	−172.6 (2)
C2—C3—C4—C5	−51.6 (3)	C2'—C3'—C4'—C5'	−52.8 (3)
C3—C4—C5—C6	−132.9 (3)	C3'—C4'—C5'—C6'	−129.1 (3)
C3—C4—C5—C10	49.5 (3)	C3'—C4'—C5'—C10'	51.2 (3)
C4—C5—C6—C7	−175.7 (3)	C4'—C5'—C6'—C7'	−177.1 (3)
C10—C5—C6—C7	1.7 (5)	C10'—C5'—C6'—C7'	2.6 (5)
C5—C6—C7—C8	12.9 (4)	C5'—C6'—C7'—C8'	14.5 (4)
C6—C7—C8—C14	−165.4 (2)	C6'—C7'—C8'—C14'	−166.7 (2)
C6—C7—C8—C9	−43.3 (3)	C6'—C7'—C8'—C9'	−44.7 (3)
C14—C8—C9—C11	−46.2 (3)	C14'—C8'—C9'—C11'	−47.8 (3)
C7—C8—C9—C11	−168.7 (2)	C7'—C8'—C9'—C11'	−170.9 (2)
C14—C8—C9—C10	−175.35 (17)	C14'—C8'—C9'—C10'	−175.86 (19)
C7—C8—C9—C10	62.2 (2)	C7'—C8'—C9'—C10'	61.1 (3)
C6—C5—C10—C19	−106.9 (3)	C6'—C5'—C10'—C19'	−110.5 (3)
C4—C5—C10—C19	70.6 (3)	C4'—C5'—C10'—C19'	69.2 (3)
C6—C5—C10—C1	134.4 (3)	C6'—C5'—C10'—C9'	12.1 (3)
C4—C5—C10—C1	−48.1 (3)	C4'—C5'—C10'—C9'	−168.2 (2)
C6—C5—C10—C9	15.5 (3)	C6'—C5'—C10'—C1'	131.2 (3)
C4—C5—C10—C9	−167.0 (2)	C4'—C5'—C10'—C1'	−49.1 (3)
C2—C1—C10—C5	52.5 (2)	C11'—C9'—C10'—C5'	−171.5 (2)
C2—C1—C10—C19	−65.6 (2)	C8'—C9'—C10'—C5'	−43.6 (3)
C2—C1—C10—C9	171.83 (18)	C11'—C9'—C10'—C19'	−50.3 (3)
C11—C9—C10—C5	−175.8 (2)	C8'—C9'—C10'—C19'	77.6 (2)
C8—C9—C10—C5	−46.9 (2)	C11'—C9'—C10'—C1'	70.8 (3)
C11—C9—C10—C19	−55.3 (2)	C8'—C9'—C10'—C1'	−161.3 (2)
C8—C9—C10—C19	73.6 (2)	C2'—C1'—C10'—C5'	52.6 (3)
C11—C9—C10—C1	66.0 (2)	C2'—C1'—C10'—C19'	−65.2 (3)
C8—C9—C10—C1	−165.10 (17)	C2'—C1'—C10'—C9'	172.7 (2)
C8—C9—C11—C12	46.3 (3)	C8'—C9'—C11'—C12'	47.8 (3)
C10—C9—C11—C12	174.6 (2)	C10'—C9'—C11'—C12'	175.7 (2)
C9—C11—C12—C13	−53.1 (3)	C9'—C11'—C12'—C13'	−53.5 (3)
C11—C12—C13—C18	−65.5 (3)	C11'—C12'—C13'—C14'	57.6 (3)
C11—C12—C13—C14	58.4 (3)	C11'—C12'—C13'—C18'	−66.2 (3)
C11—C12—C13—C17	169.0 (2)	C11'—C12'—C13'—C17'	168.1 (2)
C7—C8—C14—C15	−59.8 (3)	C7'—C8'—C14'—C15'	−57.1 (3)
C9—C8—C14—C15	178.7 (2)	C9'—C8'—C14'—C15'	−178.8 (2)
C7—C8—C14—C13	177.8 (2)	C7'—C8'—C14'—C13'	179.0 (2)
C9—C8—C14—C13	56.3 (3)	C9'—C8'—C14'—C13'	57.3 (3)
C12—C13—C14—C8	−62.5 (3)	C12'—C13'—C14'—C8'	−62.4 (3)
C18—C13—C14—C8	59.9 (3)	C18'—C13'—C14'—C8'	60.7 (3)
C17—C13—C14—C8	175.9 (2)	C17'—C13'—C14'—C8'	176.1 (2)
C12—C13—C14—C15	167.3 (2)	C12'—C13'—C14'—C15'	166.4 (2)
C18—C13—C14—C15	−70.4 (2)	C18'—C13'—C14'—C15'	−70.5 (3)
C17—C13—C14—C15	45.6 (2)	C17'—C13'—C14'—C15'	44.9 (3)
C8—C14—C15—C16	−158.9 (2)	C8'—C14'—C15'—C16'	−158.6 (2)
C13—C14—C15—C16	−31.5 (3)	C13'—C14'—C15'—C16'	−30.2 (3)
C14—C15—C16—O16	−113.5 (2)	C22'—O16'—C16'—C15'	−84.2 (3)
C14—C15—C16—C17	4.5 (3)	C22'—O16'—C16'—C17'	158.2 (2)
O16—C16—C17—C20	−88.2 (3)	C14'—C15'—C16'—O16'	−114.0 (3)
C15—C16—C17—C20	150.6 (3)	C14'—C15'—C16'—C17'	3.0 (3)
O16—C16—C17—C13	144.9 (2)	O16'—C16'—C17'—C20'	−86.7 (3)
C15—C16—C17—C13	23.7 (3)	C15'—C16'—C17'—C20'	151.5 (3)
C12—C13—C17—C20	74.0 (3)	O16'—C16'—C17'—C13'	146.5 (2)
C18—C13—C17—C20	−52.2 (3)	C15'—C16'—C17'—C13'	24.7 (3)
C14—C13—C17—C20	−171.2 (3)	C12'—C13'—C17'—C20'	77.3 (3)
C12—C13—C17—C16	−157.1 (2)	C14'—C13'—C17'—C20'	−167.9 (2)
C18—C13—C17—C16	76.7 (2)	C18'—C13'—C17'—C20'	−49.6 (3)
C14—C13—C17—C16	−42.3 (2)	C12'—C13'—C17'—C16'	−156.9 (2)
C16—C17—C20—O20	−173.8 (4)	C14'—C13'—C17'—C16'	−42.1 (3)
C13—C17—C20—O20	−52.4 (5)	C18'—C13'—C17'—C16'	76.2 (3)
C16—C17—C20—C21	4.1 (7)	C16'—C17'—C20'—O20'	−19.8 (4)
C13—C17—C20—C21	125.5 (6)	C13'—C17'—C20'—O20'	100.1 (3)
O24—C24—O3—C3	0.8 (6)	C16'—C17'—C20'—C21'	162.55 (19)
C25—C24—O3—C3	178.6 (4)	C13'—C17'—C20'—C21'	−77.6 (3)
C2—C3—O3—C24	154.1 (3)	C16'—O16'—C22'—O22'	3.8 (4)
C4—C3—O3—C24	−85.3 (4)	C16'—O16'—C22'—C23'	−175.6 (3)
O22—C22—O16—C16	4.5 (5)	C24b'—O3'—C24a'—O24a'	−115.0 (9)
C23—C22—O16—C16	−177.9 (3)	C3'—O3'—C24a'—O24a'	−11.8 (6)
C17—C16—O16—C22	161.9 (3)	C24b'—O3'—C24a'—C25a'	72.3 (8)
C15—C16—O16—C22	−80.7 (3)	C3'—O3'—C24a'—C25a'	175.5 (4)
C10'—C1'—C2'—C3'	−58.1 (4)	C24a'—O3'—C24b'—O24b'	122.3 (17)
C24a'—O3'—C3'—C2'	96.1 (4)	C3'—O3'—C24b'—O24b'	19.1 (17)
C24b'—O3'—C3'—C2'	146.6 (7)	C24a'—O3'—C24b'—C25b'	−64.7 (12)
C24a'—O3'—C3'—C4'	−142.9 (3)	C3'—O3'—C24b'—C25b'	−167.9 (11)