17-Oxo-5β-hydroxy­androstan-3β­-yl acetate

The title compound, C₂₁H₃₂O₄ crystallizes in a triclinic unit cell, which is very unusual for steroids. The asymmetric unit contains two independent mol­ecules with almost identical geometry, although they are slighly twisted in opposite directions. These mol­ecules form a dimer inter­connected via hydrogen bonds. Both mol­ecules have a cis A/B ring junction characteristic of a 5β-configuration, but differ in the orientation of their hydroxyl groups.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.092
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C20'

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.01 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

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           71.78
           From the CIF: _reflns_number_total               3750
           Count of symmetry unique reflns         3740
           Completeness (_total/calc)            100.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        10
           Fraction of Friedel pairs measured     0.003
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

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.

17-Oxo-5β-hydroxyandrostan-3β-yl acetate

Crystal data

C21H32O4	Z = 2
Mr = 348.47	F(000) = 380
Triclinic, P1	Dx = 1.214 Mg m^−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.6386 (9) Å	Cell parameters from 25 reflections
b = 8.259 (2) Å	θ = 22.0–28.7°
c = 15.7610 (12) Å	µ = 0.66 mm^−1
α = 84.415 (12)°	T = 292 K
β = 89.480 (8)°	Prism, colourless
γ = 74.529 (19)°	0.20 × 0.20 × 0.07 mm
V = 953.6 (3) Å^3

Data collection

Enraf–Nonius MACH3 diffractometer	3510 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 71.8°, θmin = 5.6°
profile data from ω scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.869, Tmax = 0.951	l = −19→19
7274 measured reflections	3 standard reflections every 180 min
3750 independent reflections	intensity decay: 10.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 0.0858P] where P = (Fo^2 + 2Fc^2)/3
3750 reflections	(Δ/σ)max < 0.001
463 parameters	Δρmax = 0.15 e Å^−3
3 restraints	Δρmin = −0.16 e Å^−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
O3	0.4882 (2)	1.34201 (19)	0.22603 (11)	0.0528 (4)
O5	0.46439 (19)	1.00218 (19)	0.26898 (9)	0.0446 (3)
H5	0.497 (4)	0.907 (4)	0.305 (2)	0.067*
O17	0.9968 (3)	0.6114 (3)	−0.20569 (12)	0.0816 (6)
O20	0.1997 (3)	1.4826 (3)	0.19830 (14)	0.0764 (6)
C1	0.7909 (3)	1.0620 (3)	0.18350 (14)	0.0465 (5)
H1A	0.7718	1.0828	0.2428	0.056*
H1B	0.9209	1.0281	0.1746	0.056*
C2	0.7087 (3)	1.2246 (3)	0.12784 (17)	0.0540 (5)
H2A	0.7652	1.3110	0.1419	0.065*
H2B	0.7322	1.2065	0.0684	0.065*
C3	0.5060 (3)	1.2837 (3)	0.14074 (14)	0.0472 (5)
H3	0.4536	1.3795	0.0986	0.057*
C4	0.4127 (3)	1.1452 (2)	0.13186 (12)	0.0391 (4)
H4A	0.4080	1.1288	0.0719	0.047*
H4B	0.2885	1.1836	0.1506	0.047*
C5	0.5009 (2)	0.9743 (2)	0.18122 (11)	0.0341 (4)
C6	0.4084 (3)	0.8414 (3)	0.15775 (14)	0.0432 (4)
H6A	0.4467	0.7424	0.1985	0.052*
H6B	0.2780	0.8858	0.1626	0.052*
C7	0.4494 (3)	0.7880 (3)	0.06813 (14)	0.0434 (4)
H7A	0.3934	0.8820	0.0267	0.052*
H7B	0.3962	0.6961	0.0601	0.052*
C8	0.6530 (3)	0.7314 (2)	0.05216 (12)	0.0349 (4)
H8	0.7069	0.6289	0.0899	0.042*
C9	0.7428 (2)	0.8712 (2)	0.07181 (11)	0.0328 (4)
H9	0.6797	0.9727	0.0354	0.039*
C10	0.7110 (2)	0.9166 (2)	0.16558 (11)	0.0334 (4)
C11	0.9450 (3)	0.8326 (3)	0.04707 (12)	0.0403 (4)
H11A	0.9884	0.9310	0.0535	0.048*
H11B	1.0150	0.7404	0.0861	0.048*
C12	0.9780 (3)	0.7849 (3)	−0.04497 (13)	0.0451 (5)
H12A	0.9234	0.8820	−0.0849	0.054*
H12B	1.1075	0.7510	−0.0552	0.054*
C13	0.8962 (3)	0.6412 (3)	−0.05890 (12)	0.0427 (4)
C14	0.6922 (3)	0.6945 (2)	−0.03997 (12)	0.0398 (4)
H14	0.6426	0.8018	−0.0748	0.048*
C15	0.6139 (4)	0.5643 (3)	−0.07893 (16)	0.0553 (6)
H15A	0.4850	0.6091	−0.0916	0.066*
H15B	0.6333	0.4609	−0.0411	0.066*
C16	0.7237 (4)	0.5345 (3)	−0.16113 (15)	0.0620 (6)
H16A	0.7589	0.4153	−0.1693	0.074*
H16B	0.6516	0.5959	−0.2102	0.074*
C17	0.8896 (4)	0.5972 (3)	−0.15051 (14)	0.0547 (6)
C18	1.0013 (3)	0.4746 (3)	−0.00730 (15)	0.0541 (5)
H18A	1.1245	0.4429	−0.0262	0.081*
H18B	0.9441	0.3870	−0.0160	0.081*
H18C	1.0003	0.4908	0.0522	0.081*
C19	0.8014 (3)	0.7646 (3)	0.22918 (13)	0.0508 (5)
H19A	0.9275	0.7240	0.2159	0.076*
H19B	0.7424	0.6764	0.2254	0.076*
H19C	0.7908	0.7984	0.2860	0.076*
C20	0.3265 (3)	1.4379 (3)	0.24653 (16)	0.0515 (5)
C21	0.3284 (4)	1.4805 (4)	0.33669 (18)	0.0672 (7)
H21A	0.2079	1.5391	0.3520	0.101*
H21B	0.4084	1.5512	0.3418	0.101*
H21C	0.3702	1.3785	0.3740	0.101*
O3'	0.8692 (2)	0.4515 (2)	0.45722 (10)	0.0596 (4)
O5'	0.5725 (2)	0.72854 (19)	0.41167 (8)	0.0419 (3)
H5'	0.670 (4)	0.657 (4)	0.4025 (19)	0.063*
O17'	0.4767 (3)	1.1935 (3)	0.90350 (11)	0.0669 (5)
O20'	1.0660 (5)	0.2129 (4)	0.50245 (18)	0.1264 (13)
C1'	0.8652 (3)	0.7953 (3)	0.51445 (12)	0.0414 (4)
H1'1	0.8863	0.7847	0.4542	0.050*
H1'2	0.9320	0.8716	0.5319	0.050*
C2'	0.9410 (3)	0.6226 (3)	0.56373 (14)	0.0515 (5)
H2'1	1.0672	0.5785	0.5489	0.062*
H2'2	0.9369	0.6351	0.6243	0.062*
C3'	0.8366 (3)	0.4983 (3)	0.54517 (14)	0.0520 (5)
H3'	0.8755	0.3968	0.5854	0.062*
C4'	0.6334 (3)	0.5716 (3)	0.55105 (13)	0.0459 (5)
H4'1	0.6031	0.5793	0.6107	0.055*
H4'2	0.5733	0.4936	0.5298	0.055*
C5'	0.5565 (2)	0.7456 (2)	0.50244 (11)	0.0352 (4)
C6'	0.3534 (3)	0.8085 (3)	0.51729 (15)	0.0475 (5)
H6'1	0.2951	0.7227	0.5043	0.057*
H6'2	0.3032	0.9087	0.4786	0.057*
C7'	0.3104 (3)	0.8502 (3)	0.60849 (14)	0.0471 (5)
H7'1	0.3466	0.7474	0.6469	0.057*
H7'2	0.1804	0.8969	0.6134	0.057*
C8'	0.4086 (2)	0.9763 (2)	0.63453 (12)	0.0359 (4)
H8'	0.3615	1.0832	0.5990	0.043*
C9'	0.6162 (2)	0.9141 (2)	0.62086 (11)	0.0321 (4)
H9'	0.6593	0.8070	0.6567	0.038*
C10'	0.6608 (2)	0.8745 (2)	0.52680 (11)	0.0334 (4)
C11'	0.7174 (3)	1.0357 (3)	0.65239 (13)	0.0459 (5)
H11C	0.8472	0.9853	0.6492	0.055*
H11D	0.6876	1.1395	0.6146	0.055*
C12'	0.6715 (3)	1.0783 (3)	0.74404 (13)	0.0462 (5)
H12C	0.7185	0.9783	0.7833	0.055*
H12D	0.7292	1.1640	0.7579	0.055*
C13'	0.4671 (3)	1.1423 (2)	0.75410 (12)	0.0389 (4)
C14'	0.3770 (2)	1.0090 (2)	0.72748 (12)	0.0360 (4)
H14'	0.4376	0.9031	0.7612	0.043*
C15'	0.1828 (3)	1.0632 (3)	0.76148 (15)	0.0512 (5)
H15C	0.1062	1.1544	0.7242	0.061*
H15D	0.1284	0.9693	0.7679	0.061*
C16'	0.2137 (3)	1.1220 (4)	0.84821 (16)	0.0588 (6)
H16C	0.1192	1.2226	0.8584	0.071*
H16D	0.2127	1.0343	0.8937	0.071*
C17'	0.3979 (3)	1.1592 (3)	0.84435 (13)	0.0467 (5)
C18'	0.3901 (4)	1.3184 (3)	0.70618 (16)	0.0567 (6)
H18D	0.2613	1.3547	0.7141	0.085*
H18E	0.4145	1.3134	0.6465	0.085*
H18F	0.4466	1.3970	0.7280	0.085*
C19'	0.6047 (3)	1.0377 (3)	0.46616 (13)	0.0467 (5)
H19D	0.6757	1.1124	0.4791	0.070*
H19E	0.4783	1.0916	0.4731	0.070*
H19F	0.6252	1.0111	0.4083	0.070*
C20'	0.9809 (3)	0.3020 (3)	0.44587 (17)	0.0569 (6)
C21'	0.9802 (5)	0.2635 (4)	0.3556 (2)	0.0772 (8)
H21D	1.0796	0.1674	0.3473	0.116*
H21E	0.9926	0.3591	0.3186	0.116*
H21F	0.8678	0.2392	0.3427	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0580 (9)	0.0456 (8)	0.0543 (9)	−0.0070 (7)	0.0020 (7)	−0.0221 (7)
O5	0.0494 (8)	0.0495 (8)	0.0284 (6)	−0.0007 (6)	0.0074 (5)	−0.0084 (6)
O17	0.0974 (14)	0.1032 (16)	0.0434 (9)	−0.0193 (12)	0.0227 (9)	−0.0266 (10)
O20	0.0692 (11)	0.0711 (12)	0.0696 (12)	0.0203 (9)	−0.0072 (9)	−0.0222 (9)
C1	0.0384 (10)	0.0549 (12)	0.0494 (11)	−0.0112 (9)	0.0015 (8)	−0.0244 (9)
C2	0.0602 (13)	0.0445 (11)	0.0643 (14)	−0.0223 (10)	0.0170 (11)	−0.0187 (10)
C3	0.0595 (12)	0.0342 (9)	0.0451 (11)	−0.0062 (9)	0.0042 (9)	−0.0081 (8)
C4	0.0379 (9)	0.0386 (10)	0.0356 (9)	0.0003 (8)	−0.0019 (7)	−0.0078 (7)
C5	0.0357 (9)	0.0357 (9)	0.0292 (8)	−0.0054 (7)	0.0024 (7)	−0.0069 (7)
C6	0.0405 (9)	0.0445 (10)	0.0464 (11)	−0.0132 (8)	0.0106 (8)	−0.0091 (8)
C7	0.0409 (10)	0.0451 (10)	0.0493 (11)	−0.0159 (8)	0.0045 (8)	−0.0170 (9)
C8	0.0396 (9)	0.0326 (9)	0.0323 (9)	−0.0081 (7)	0.0023 (7)	−0.0066 (7)
C9	0.0352 (9)	0.0341 (9)	0.0284 (8)	−0.0067 (7)	0.0002 (6)	−0.0073 (7)
C10	0.0324 (8)	0.0367 (9)	0.0278 (8)	−0.0016 (7)	−0.0011 (6)	−0.0081 (7)
C11	0.0385 (9)	0.0485 (11)	0.0362 (10)	−0.0123 (8)	0.0055 (7)	−0.0135 (8)
C12	0.0446 (10)	0.0558 (12)	0.0356 (10)	−0.0126 (9)	0.0102 (8)	−0.0108 (9)
C13	0.0502 (11)	0.0437 (10)	0.0296 (9)	−0.0023 (9)	0.0053 (8)	−0.0104 (8)
C14	0.0474 (11)	0.0381 (10)	0.0335 (9)	−0.0083 (8)	−0.0002 (8)	−0.0103 (8)
C15	0.0671 (14)	0.0527 (13)	0.0501 (12)	−0.0178 (11)	−0.0058 (10)	−0.0189 (10)
C16	0.0833 (17)	0.0574 (13)	0.0431 (12)	−0.0085 (12)	−0.0070 (11)	−0.0231 (10)
C17	0.0701 (15)	0.0514 (12)	0.0361 (11)	−0.0011 (11)	0.0048 (10)	−0.0161 (9)
C18	0.0601 (13)	0.0475 (12)	0.0455 (11)	0.0041 (10)	0.0022 (10)	−0.0111 (9)
C19	0.0487 (11)	0.0559 (12)	0.0330 (10)	0.0114 (9)	−0.0011 (8)	−0.0027 (9)
C20	0.0598 (13)	0.0379 (10)	0.0563 (13)	−0.0090 (9)	0.0095 (10)	−0.0149 (9)
C21	0.0796 (17)	0.0698 (16)	0.0610 (15)	−0.0272 (14)	0.0139 (13)	−0.0302 (13)
O3'	0.0771 (11)	0.0479 (9)	0.0421 (8)	0.0056 (8)	0.0064 (7)	−0.0108 (7)
O5'	0.0487 (8)	0.0486 (8)	0.0301 (6)	−0.0127 (6)	−0.0004 (5)	−0.0120 (6)
O17'	0.0854 (12)	0.0804 (12)	0.0396 (8)	−0.0248 (10)	0.0026 (8)	−0.0216 (8)
O20'	0.149 (3)	0.0907 (17)	0.0884 (17)	0.0624 (18)	−0.0211 (16)	−0.0235 (14)
C1'	0.0345 (9)	0.0590 (12)	0.0345 (9)	−0.0162 (8)	0.0068 (7)	−0.0129 (8)
C2'	0.0366 (9)	0.0667 (14)	0.0429 (11)	0.0027 (9)	−0.0023 (8)	−0.0113 (10)
C3'	0.0672 (14)	0.0460 (11)	0.0340 (10)	−0.0002 (10)	0.0045 (9)	−0.0025 (8)
C4'	0.0605 (12)	0.0433 (11)	0.0382 (10)	−0.0207 (9)	0.0094 (9)	−0.0070 (8)
C5'	0.0362 (9)	0.0439 (10)	0.0285 (9)	−0.0142 (8)	0.0031 (7)	−0.0093 (7)
C6'	0.0359 (9)	0.0652 (13)	0.0496 (12)	−0.0212 (9)	0.0016 (8)	−0.0240 (10)
C7'	0.0333 (9)	0.0671 (14)	0.0496 (11)	−0.0224 (9)	0.0102 (8)	−0.0238 (10)
C8'	0.0295 (8)	0.0454 (10)	0.0348 (9)	−0.0113 (7)	0.0006 (7)	−0.0101 (8)
C9'	0.0281 (8)	0.0408 (9)	0.0280 (8)	−0.0090 (7)	0.0011 (6)	−0.0083 (7)
C10'	0.0327 (8)	0.0416 (10)	0.0286 (8)	−0.0131 (7)	0.0016 (7)	−0.0072 (7)
C11'	0.0384 (9)	0.0661 (13)	0.0426 (11)	−0.0243 (9)	0.0057 (8)	−0.0223 (10)
C12'	0.0441 (10)	0.0624 (13)	0.0373 (10)	−0.0183 (9)	−0.0002 (8)	−0.0194 (9)
C13'	0.0442 (10)	0.0398 (10)	0.0334 (9)	−0.0105 (8)	0.0015 (8)	−0.0092 (7)
C14'	0.0332 (9)	0.0409 (10)	0.0339 (9)	−0.0084 (7)	0.0036 (7)	−0.0082 (7)
C15'	0.0396 (10)	0.0665 (14)	0.0487 (12)	−0.0122 (10)	0.0117 (9)	−0.0193 (10)
C16'	0.0624 (14)	0.0688 (15)	0.0466 (12)	−0.0155 (12)	0.0189 (10)	−0.0207 (11)
C17'	0.0607 (12)	0.0419 (10)	0.0352 (10)	−0.0073 (9)	0.0047 (9)	−0.0109 (8)
C18'	0.0740 (15)	0.0450 (12)	0.0504 (12)	−0.0152 (11)	0.0039 (11)	−0.0039 (10)
C19'	0.0647 (13)	0.0449 (11)	0.0330 (9)	−0.0195 (9)	0.0017 (8)	−0.0023 (8)
C20'	0.0519 (12)	0.0507 (12)	0.0655 (15)	−0.0051 (10)	0.0037 (11)	−0.0177 (11)
C21'	0.0862 (19)	0.081 (2)	0.0752 (18)	−0.0288 (16)	0.0195 (15)	−0.0429 (16)

Geometric parameters (Å, º)

O3—C20	1.334 (3)	O3'—C20'	1.328 (3)
O3—C3	1.464 (2)	O3'—C3'	1.476 (3)
O5—C5	1.437 (2)	O5'—C5'	1.452 (2)
O5—H5	0.90 (3)	O5'—H5'	0.84 (3)
O17—C17	1.208 (3)	O17'—C17'	1.210 (3)
O20—C20	1.192 (3)	O20'—C20'	1.178 (4)
C1—C2	1.516 (4)	C1'—C2'	1.525 (3)
C1—C10	1.535 (3)	C1'—C10'	1.542 (3)
C1—H1A	0.9700	C1'—H1'1	0.9700
C1—H1B	0.9700	C1'—H1'2	0.9700
C2—C3	1.513 (3)	C2'—C3'	1.508 (4)
C2—H2A	0.9700	C2'—H2'1	0.9700
C2—H2B	0.9700	C2'—H2'2	0.9700
C3—C4	1.518 (3)	C3'—C4'	1.514 (3)
C3—H3	0.9800	C3'—H3'	0.9800
C4—C5	1.529 (3)	C4'—C5'	1.530 (3)
C4—H4A	0.9700	C4'—H4'1	0.9700
C4—H4B	0.9700	C4'—H4'2	0.9700
C5—C6	1.530 (3)	C5'—C6'	1.523 (3)
C5—C10	1.572 (2)	C5'—C10'	1.566 (2)
C6—C7	1.526 (3)	C6'—C7'	1.523 (3)
C6—H6A	0.9700	C6'—H6'1	0.9700
C6—H6B	0.9700	C6'—H6'2	0.9700
C7—C8	1.526 (3)	C7'—C8'	1.524 (3)
C7—H7A	0.9700	C7'—H7'1	0.9700
C7—H7B	0.9700	C7'—H7'2	0.9700
C8—C14	1.523 (2)	C8'—C14'	1.521 (2)
C8—C9	1.548 (2)	C8'—C9'	1.551 (2)
C8—H8	0.9800	C8'—H8'	0.9800
C9—C11	1.546 (3)	C9'—C11'	1.540 (3)
C9—C10	1.561 (2)	C9'—C10'	1.564 (2)
C9—H9	0.9800	C9'—H9'	0.9800
C10—C19	1.537 (3)	C10'—C19'	1.537 (3)
C11—C12	1.541 (3)	C11'—C12'	1.535 (3)
C11—H11A	0.9700	C11'—H11C	0.9700
C11—H11B	0.9700	C11'—H11D	0.9700
C12—C13	1.515 (3)	C12'—C13'	1.522 (3)
C12—H12A	0.9700	C12'—H12C	0.9700
C12—H12B	0.9700	C12'—H12D	0.9700
C13—C17	1.528 (3)	C13'—C17'	1.519 (3)
C13—C14	1.537 (3)	C13'—C14'	1.537 (3)
C13—C18	1.551 (3)	C13'—C18'	1.539 (3)
C14—C15	1.539 (3)	C14'—C15'	1.538 (3)
C14—H14	0.9800	C14'—H14'	0.9800
C15—C16	1.541 (4)	C15'—C16'	1.535 (3)
C15—H15A	0.9700	C15'—H15C	0.9700
C15—H15B	0.9700	C15'—H15D	0.9700
C16—C17	1.507 (4)	C16'—C17'	1.518 (4)
C16—H16A	0.9700	C16'—H16C	0.9700
C16—H16B	0.9700	C16'—H16D	0.9700
C18—H18A	0.9600	C18'—H18D	0.9600
C18—H18B	0.9600	C18'—H18E	0.9600
C18—H18C	0.9600	C18'—H18F	0.9600
C19—H19A	0.9600	C19'—H19D	0.9600
C19—H19B	0.9600	C19'—H19E	0.9600
C19—H19C	0.9600	C19'—H19F	0.9600
C20—C21	1.498 (3)	C20'—C21'	1.488 (4)
C21—H21A	0.9600	C21'—H21D	0.9600
C21—H21B	0.9600	C21'—H21E	0.9600
C21—H21C	0.9600	C21'—H21F	0.9600
C20—O3—C3	117.44 (18)	C20'—O3'—C3'	118.30 (18)
C5—O5—H5	113 (2)	C5'—O5'—H5'	110 (2)
C2—C1—C10	113.49 (17)	C2'—C1'—C10'	114.58 (17)
C2—C1—H1A	108.9	C2'—C1'—H1'1	108.6
C10—C1—H1A	108.9	C10'—C1'—H1'1	108.6
C2—C1—H1B	108.9	C2'—C1'—H1'2	108.6
C10—C1—H1B	108.9	C10'—C1'—H1'2	108.6
H1A—C1—H1B	107.7	H1'1—C1'—H1'2	107.6
C3—C2—C1	110.68 (18)	C3'—C2'—C1'	112.41 (17)
C3—C2—H2A	109.5	C3'—C2'—H2'1	109.1
C1—C2—H2A	109.5	C1'—C2'—H2'1	109.1
C3—C2—H2B	109.5	C3'—C2'—H2'2	109.1
C1—C2—H2B	109.5	C1'—C2'—H2'2	109.1
H2A—C2—H2B	108.1	H2'1—C2'—H2'2	107.9
O3—C3—C2	104.56 (18)	O3'—C3'—C2'	110.43 (19)
O3—C3—C4	112.66 (17)	O3'—C3'—C4'	105.93 (18)
C2—C3—C4	112.18 (17)	C2'—C3'—C4'	112.18 (18)
O3—C3—H3	109.1	O3'—C3'—H3'	109.4
C2—C3—H3	109.1	C2'—C3'—H3'	109.4
C4—C3—H3	109.1	C4'—C3'—H3'	109.4
C3—C4—C5	115.92 (16)	C3'—C4'—C5'	115.56 (17)
C3—C4—H4A	108.3	C3'—C4'—H4'1	108.4
C5—C4—H4A	108.3	C5'—C4'—H4'1	108.4
C3—C4—H4B	108.3	C3'—C4'—H4'2	108.4
C5—C4—H4B	108.3	C5'—C4'—H4'2	108.4
H4A—C4—H4B	107.4	H4'1—C4'—H4'2	107.5
O5—C5—C4	104.33 (14)	O5'—C5'—C6'	105.14 (15)
O5—C5—C6	108.36 (15)	O5'—C5'—C4'	108.56 (15)
C4—C5—C6	110.36 (15)	C6'—C5'—C4'	110.23 (18)
O5—C5—C10	111.12 (14)	O5'—C5'—C10'	109.54 (14)
C4—C5—C10	111.49 (15)	C6'—C5'—C10'	111.76 (16)
C6—C5—C10	110.95 (15)	C4'—C5'—C10'	111.37 (15)
C7—C6—C5	114.06 (16)	C5'—C6'—C7'	112.73 (16)
C7—C6—H6A	108.7	C5'—C6'—H6'1	109.0
C5—C6—H6A	108.7	C7'—C6'—H6'1	109.0
C7—C6—H6B	108.7	C5'—C6'—H6'2	109.0
C5—C6—H6B	108.7	C7'—C6'—H6'2	109.0
H6A—C6—H6B	107.6	H6'1—C6'—H6'2	107.8
C6—C7—C8	112.24 (16)	C6'—C7'—C8'	111.41 (17)
C6—C7—H7A	109.2	C6'—C7'—H7'1	109.3
C8—C7—H7A	109.2	C8'—C7'—H7'1	109.3
C6—C7—H7B	109.2	C6'—C7'—H7'2	109.3
C8—C7—H7B	109.2	C8'—C7'—H7'2	109.3
H7A—C7—H7B	107.9	H7'1—C7'—H7'2	108.0
C14—C8—C7	111.77 (16)	C14'—C8'—C7'	111.67 (16)
C14—C8—C9	108.31 (15)	C14'—C8'—C9'	108.48 (13)
C7—C8—C9	109.89 (15)	C7'—C8'—C9'	111.50 (15)
C14—C8—H8	108.9	C14'—C8'—H8'	108.4
C7—C8—H8	108.9	C7'—C8'—H8'	108.4
C9—C8—H8	108.9	C9'—C8'—H8'	108.4
C11—C9—C8	113.04 (14)	C11'—C9'—C8'	111.67 (15)
C11—C9—C10	112.77 (14)	C11'—C9'—C10'	113.15 (15)
C8—C9—C10	111.96 (14)	C8'—C9'—C10'	111.82 (13)
C11—C9—H9	106.1	C11'—C9'—H9'	106.6
C8—C9—H9	106.1	C8'—C9'—H9'	106.6
C10—C9—H9	106.1	C10'—C9'—H9'	106.6
C1—C10—C19	107.16 (17)	C19'—C10'—C1'	107.33 (16)
C1—C10—C9	111.89 (16)	C19'—C10'—C9'	110.17 (15)
C19—C10—C9	110.92 (15)	C1'—C10'—C9'	112.37 (14)
C1—C10—C5	107.72 (15)	C19'—C10'—C5'	110.28 (15)
C19—C10—C5	110.13 (16)	C1'—C10'—C5'	107.76 (15)
C9—C10—C5	108.96 (14)	C9'—C10'—C5'	108.89 (14)
C12—C11—C9	113.15 (15)	C12'—C11'—C9'	113.57 (16)
C12—C11—H11A	108.9	C12'—C11'—H11C	108.9
C9—C11—H11A	108.9	C9'—C11'—H11C	108.9
C12—C11—H11B	108.9	C12'—C11'—H11D	108.9
C9—C11—H11B	108.9	C9'—C11'—H11D	108.9
H11A—C11—H11B	107.8	H11C—C11'—H11D	107.7
C13—C12—C11	109.97 (16)	C13'—C12'—C11'	110.69 (16)
C13—C12—H12A	109.7	C13'—C12'—H12C	109.5
C11—C12—H12A	109.7	C11'—C12'—H12C	109.5
C13—C12—H12B	109.7	C13'—C12'—H12D	109.5
C11—C12—H12B	109.7	C11'—C12'—H12D	109.5
H12A—C12—H12B	108.2	H12C—C12'—H12D	108.1
C12—C13—C17	116.70 (18)	C17'—C13'—C12'	116.91 (17)
C12—C13—C14	109.18 (16)	C17'—C13'—C14'	100.42 (16)
C17—C13—C14	100.28 (16)	C12'—C13'—C14'	108.82 (16)
C12—C13—C18	111.39 (18)	C17'—C13'—C18'	104.89 (17)
C17—C13—C18	105.16 (17)	C12'—C13'—C18'	111.84 (19)
C14—C13—C18	113.80 (18)	C14'—C13'—C18'	113.59 (17)
C8—C14—C13	113.18 (15)	C8'—C14'—C13'	112.65 (15)
C8—C14—C15	120.22 (18)	C8'—C14'—C15'	120.47 (15)
C13—C14—C15	104.74 (17)	C13'—C14'—C15'	104.27 (16)
C8—C14—H14	105.9	C8'—C14'—H14'	106.2
C13—C14—H14	105.9	C13'—C14'—H14'	106.2
C15—C14—H14	105.9	C15'—C14'—H14'	106.2
C14—C15—C16	102.4 (2)	C16'—C15'—C14'	102.33 (17)
C14—C15—H15A	111.3	C16'—C15'—H15C	111.3
C16—C15—H15A	111.3	C14'—C15'—H15C	111.3
C14—C15—H15B	111.3	C16'—C15'—H15D	111.3
C16—C15—H15B	111.3	C14'—C15'—H15D	111.3
H15A—C15—H15B	109.2	H15C—C15'—H15D	109.2
C17—C16—C15	106.71 (18)	C17'—C16'—C15'	106.32 (17)
C17—C16—H16A	110.4	C17'—C16'—H16C	110.5
C15—C16—H16A	110.4	C15'—C16'—H16C	110.5
C17—C16—H16B	110.4	C17'—C16'—H16D	110.5
C15—C16—H16B	110.4	C15'—C16'—H16D	110.5
H16A—C16—H16B	108.6	H16C—C16'—H16D	108.7
O17—C17—C16	125.4 (2)	O17'—C17'—C16'	125.7 (2)
O17—C17—C13	126.4 (2)	O17'—C17'—C13'	126.2 (2)
C16—C17—C13	108.20 (19)	C16'—C17'—C13'	108.14 (17)
C13—C18—H18A	109.5	C13'—C18'—H18D	109.5
C13—C18—H18B	109.5	C13'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C13—C18—H18C	109.5	C13'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C10—C19—H19A	109.5	C10'—C19'—H19D	109.5
C10—C19—H19B	109.5	C10'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C10—C19—H19C	109.5	C10'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
O20—C20—O3	123.4 (2)	O20'—C20'—O3'	122.2 (2)
O20—C20—C21	125.7 (2)	O20'—C20'—C21'	125.9 (3)
O3—C20—C21	110.9 (2)	O3'—C20'—C21'	111.9 (2)
C20—C21—H21A	109.5	C20'—C21'—H21D	109.5
C20—C21—H21B	109.5	C20'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
C20—C21—H21C	109.5	C20'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5
C10—C1—C2—C3	59.5 (2)	C20'—O3'—C3'—C2'	103.6 (2)
C20—O3—C3—C2	164.26 (18)	C20'—O3'—C3'—C4'	−134.7 (2)
C20—O3—C3—C4	−73.7 (2)	C1'—C2'—C3'—O3'	69.7 (2)
C1—C2—C3—O3	71.3 (2)	C1'—C2'—C3'—C4'	−48.3 (2)
C1—C2—C3—C4	−51.1 (2)	O3'—C3'—C4'—C5'	−71.4 (2)
O3—C3—C4—C5	−69.6 (2)	C2'—C3'—C4'—C5'	49.1 (2)
C2—C3—C4—C5	48.1 (2)	C3'—C4'—C5'—O5'	68.2 (2)
C3—C4—C5—O5	71.0 (2)	C3'—C4'—C5'—C6'	−177.09 (17)
C3—C4—C5—C6	−172.77 (16)	C3'—C4'—C5'—C10'	−52.5 (2)
C3—C4—C5—C10	−49.0 (2)	O5'—C5'—C6'—C7'	−174.55 (17)
O5—C5—C6—C7	−175.02 (15)	C4'—C5'—C6'—C7'	68.6 (2)
C4—C5—C6—C7	71.3 (2)	C10'—C5'—C6'—C7'	−55.8 (2)
C10—C5—C6—C7	−52.8 (2)	C5'—C6'—C7'—C8'	55.0 (3)
C5—C6—C7—C8	53.2 (2)	C6'—C7'—C8'—C14'	−175.97 (17)
C6—C7—C8—C14	−174.55 (16)	C6'—C7'—C8'—C9'	−54.4 (2)
C6—C7—C8—C9	−54.3 (2)	C14'—C8'—C9'—C11'	−53.0 (2)
C14—C8—C9—C11	−50.83 (19)	C7'—C8'—C9'—C11'	−176.38 (17)
C7—C8—C9—C11	−173.18 (16)	C14'—C8'—C9'—C10'	179.06 (15)
C14—C8—C9—C10	−179.52 (15)	C7'—C8'—C9'—C10'	55.7 (2)
C7—C8—C9—C10	58.13 (19)	C2'—C1'—C10'—C19'	−174.44 (16)
C2—C1—C10—C19	−177.57 (17)	C2'—C1'—C10'—C9'	64.3 (2)
C2—C1—C10—C9	60.6 (2)	C2'—C1'—C10'—C5'	−55.7 (2)
C2—C1—C10—C5	−59.1 (2)	C11'—C9'—C10'—C19'	−60.9 (2)
C11—C9—C10—C1	54.4 (2)	C8'—C9'—C10'—C19'	66.3 (2)
C8—C9—C10—C1	−176.81 (15)	C11'—C9'—C10'—C1'	58.8 (2)
C11—C9—C10—C19	−65.2 (2)	C8'—C9'—C10'—C1'	−174.10 (15)
C8—C9—C10—C19	63.6 (2)	C11'—C9'—C10'—C5'	178.07 (16)
C11—C9—C10—C5	173.36 (15)	C8'—C9'—C10'—C5'	−54.79 (19)
C8—C9—C10—C5	−57.81 (19)	O5'—C5'—C10'—C19'	49.8 (2)
O5—C5—C10—C1	−63.9 (2)	C6'—C5'—C10'—C19'	−66.3 (2)
C4—C5—C10—C1	52.0 (2)	C4'—C5'—C10'—C19'	169.92 (16)
C6—C5—C10—C1	175.45 (15)	O5'—C5'—C10'—C1'	−67.06 (18)
O5—C5—C10—C19	52.6 (2)	C6'—C5'—C10'—C1'	176.83 (16)
C4—C5—C10—C19	168.55 (15)	C4'—C5'—C10'—C1'	53.06 (19)
C6—C5—C10—C19	−68.0 (2)	O5'—C5'—C10'—C9'	170.80 (14)
O5—C5—C10—C9	174.50 (14)	C6'—C5'—C10'—C9'	54.7 (2)
C4—C5—C10—C9	−69.57 (18)	C4'—C5'—C10'—C9'	−69.09 (19)
C6—C5—C10—C9	53.9 (2)	C8'—C9'—C11'—C12'	51.6 (2)
C8—C9—C11—C12	50.8 (2)	C10'—C9'—C11'—C12'	178.79 (17)
C10—C9—C11—C12	179.07 (16)	C9'—C11'—C12'—C13'	−53.2 (3)
C9—C11—C12—C13	−53.6 (2)	C11'—C12'—C13'—C17'	169.07 (18)
C11—C12—C13—C17	170.40 (17)	C11'—C12'—C13'—C14'	56.3 (2)
C11—C12—C13—C14	57.7 (2)	C11'—C12'—C13'—C18'	−70.0 (2)
C11—C12—C13—C18	−68.8 (2)	C7'—C8'—C14'—C13'	−177.21 (16)
C7—C8—C14—C13	178.60 (16)	C9'—C8'—C14'—C13'	59.5 (2)
C9—C8—C14—C13	57.4 (2)	C7'—C8'—C14'—C15'	−53.5 (2)
C7—C8—C14—C15	−56.7 (2)	C9'—C8'—C14'—C15'	−176.76 (18)
C9—C8—C14—C15	−177.86 (17)	C17'—C13'—C14'—C8'	174.81 (15)
C12—C13—C14—C8	−62.4 (2)	C12'—C13'—C14'—C8'	−61.9 (2)
C17—C13—C14—C8	174.52 (16)	C18'—C13'—C14'—C8'	63.4 (2)
C18—C13—C14—C8	62.8 (2)	C17'—C13'—C14'—C15'	42.5 (2)
C12—C13—C14—C15	164.89 (17)	C12'—C13'—C14'—C15'	165.80 (17)
C17—C13—C14—C15	41.8 (2)	C18'—C13'—C14'—C15'	−68.9 (2)
C18—C13—C14—C15	−70.0 (2)	C8'—C14'—C15'—C16'	−166.93 (19)
C8—C14—C15—C16	−166.22 (18)	C13'—C14'—C15'—C16'	−39.3 (2)
C13—C14—C15—C16	−37.6 (2)	C14'—C15'—C16'—C17'	20.2 (3)
C14—C15—C16—C17	18.1 (3)	C15'—C16'—C17'—O17'	−172.7 (2)
C15—C16—C17—O17	−171.4 (3)	C15'—C16'—C17'—C13'	6.1 (3)
C15—C16—C17—C13	7.8 (3)	C12'—C13'—C17'—O17'	31.7 (3)
C12—C13—C17—O17	31.2 (3)	C14'—C13'—C17'—O17'	149.2 (2)
C14—C13—C17—O17	148.9 (3)	C18'—C13'—C17'—O17'	−92.8 (3)
C18—C13—C17—O17	−92.8 (3)	C12'—C13'—C17'—C16'	−147.17 (19)
C12—C13—C17—C16	−148.0 (2)	C14'—C13'—C17'—C16'	−29.7 (2)
C14—C13—C17—C16	−30.3 (2)	C18'—C13'—C17'—C16'	88.3 (2)
C18—C13—C17—C16	88.0 (2)	C3'—O3'—C20'—O20'	−6.7 (4)
C3—O3—C20—O20	−2.7 (3)	C3'—O3'—C20'—C21'	172.2 (2)
C3—O3—C20—C21	177.53 (19)	C19—C10—C13—C18	−1.31 (18)
C10'—C1'—C2'—C3'	54.4 (2)	C19'—C10'—C13'—C18'	3.06 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O5′	0.90 (3)	2.11 (3)	2.983 (2)	165 (3)
O5′—H5′···O3′	0.84 (3)	2.07 (3)	2.798 (2)	144 (3)