1-β-Hydro­xy­corticosterone hemihydrate

The title compound, 4-pregnene-1β,11β,21-triol-3,20-dione hemihydrate, C₂₁H₃₀O₅·0.5H₂O, has two independent steroid mol­ecules and one water molecule in the asymmetric unit, and these steroid molecules have nearly identical conformations. In each, the two OH groups attached to the ring system form an intramolecular hydrogen bond, with O...O distances 2.738 (3) and 2.768 (3) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.089
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2W    ..  H10A     =       2.06 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1B    -   H10B     =       1.01 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O5B    -   H50B     =       1.02 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1W    ..  H10B     =       2.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

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               4338
           Count of symmetry unique reflns         4402
           Completeness (_total/calc)             98.55%
           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
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

4-Pregnen-1β, 11β, 21-triol-3, 20-dione

Crystal data

C21H30O5·0.5H2O	Z = 2
Mr = 371.46	F(000) = 402
Triclinic, P1	Dx = 1.284 Mg m^−3
Hall symbol: P 1	Melting point = 473–475 K
a = 7.781 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.598 (3) Å	Cell parameters from 4095 reflections
c = 12.432 (4) Å	θ = 2.5–27.5°
α = 95.131 (11)°	µ = 0.09 mm^−1
β = 107.490 (12)°	T = 100 K
γ = 97.32 (2)°	Needle, colorless
V = 960.9 (5) Å^3	0.50 × 0.10 × 0.07 mm

Data collection

Nonius KappaCCD (with an Oxford Cryosystems Cryostream coller ) diffractometer	3588 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
ω scans with κ offsets	h = −10→9
21194 measured reflections	k = −13→13
4338 independent reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 0.0079P] where P = (Fo^2 + 2Fc^2)/3
4338 reflections	(Δ/σ)max = 0.001
507 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.21 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
O1A	1.0576 (2)	0.6421 (2)	0.17473 (16)	0.0343 (4)
H10A	1.091 (5)	0.572 (4)	0.141 (3)	0.052*
O2A	0.5148 (2)	0.57543 (19)	−0.13459 (16)	0.0356 (4)
O3A	1.1285 (2)	0.70032 (18)	0.40450 (16)	0.0290 (4)
H30A	1.137 (4)	0.689 (3)	0.333 (3)	0.044*
O4A	1.0802 (2)	0.70597 (17)	0.84557 (15)	0.0312 (4)
O5A	1.1793 (2)	0.46711 (18)	0.85838 (15)	0.0285 (4)
H50A	1.272 (5)	0.513 (3)	0.857 (3)	0.043*
C1A	0.8635 (3)	0.6338 (3)	0.1324 (2)	0.0270 (5)
H1A	0.8061	0.5475	0.1422	0.032*
C2A	0.8063 (4)	0.6460 (3)	0.0054 (2)	0.0324 (6)
H2A1	0.8656	0.7297	−0.0064	0.039*
H2A2	0.8464	0.5771	−0.0358	0.039*
C3A	0.6025 (3)	0.6362 (3)	−0.0407 (2)	0.0292 (6)
C4A	0.5198 (3)	0.7069 (3)	0.0317 (2)	0.0292 (6)
H4A	0.3952	0.7162	0.0014	0.035*
C5A	0.6122 (3)	0.7591 (2)	0.1392 (2)	0.0275 (5)
C6A	0.5274 (4)	0.8455 (3)	0.2043 (2)	0.0319 (6)
H6A1	0.3975	0.8420	0.1597	0.038*
H6A2	0.5897	0.9350	0.2128	0.038*
C7A	0.5385 (3)	0.8094 (3)	0.3224 (2)	0.0278 (6)
H7A1	0.4483	0.7313	0.3137	0.033*
H7A2	0.5047	0.8796	0.3660	0.033*
C8A	0.7285 (3)	0.7846 (2)	0.3905 (2)	0.0227 (5)
H8A	0.8173	0.8667	0.4108	0.027*
C9A	0.7897 (3)	0.6863 (2)	0.3163 (2)	0.0222 (5)
H9A	0.6842	0.6141	0.2893	0.027*
C10A	0.8050 (3)	0.7377 (2)	0.2034 (2)	0.0244 (5)
C11A	0.9522 (3)	0.6229 (2)	0.3799 (2)	0.0236 (5)
H11A	0.9506	0.5433	0.3297	0.028*
C12A	0.9367 (3)	0.5816 (2)	0.4926 (2)	0.0232 (5)
H12A	0.8383	0.5066	0.4756	0.028*
H12B	1.0525	0.5544	0.5348	0.028*
C13A	0.8961 (3)	0.6876 (2)	0.5681 (2)	0.0198 (5)
C14A	0.7188 (3)	0.7307 (2)	0.4987 (2)	0.0218 (5)
H14A	0.6248	0.6513	0.4729	0.026*
C15A	0.6615 (3)	0.8130 (3)	0.5864 (2)	0.0266 (5)
H15A	0.5275	0.8097	0.5620	0.032*
H15B	0.7214	0.9035	0.5976	0.032*
C16A	0.7272 (4)	0.7507 (3)	0.6967 (2)	0.0297 (6)
H16A	0.6216	0.7132	0.7187	0.036*
H16B	0.8075	0.8155	0.7600	0.036*
C17A	0.8338 (3)	0.6443 (2)	0.6698 (2)	0.0232 (5)
H17A	0.7461	0.5619	0.6417	0.028*
C18A	1.0590 (3)	0.7971 (2)	0.6135 (2)	0.0245 (5)
H18A	1.1684	0.7627	0.6533	0.037*
H18B	1.0333	0.8607	0.6663	0.037*
H18C	1.0795	0.8381	0.5498	0.037*
C19A	0.9341 (4)	0.8669 (3)	0.2226 (2)	0.0320 (6)
H19A	0.9358	0.8919	0.1489	0.048*
H19B	1.0577	0.8576	0.2679	0.048*
H19C	0.8905	0.9331	0.2631	0.048*
C20A	0.9900 (3)	0.6224 (2)	0.7701 (2)	0.0229 (5)
C21A	1.0283 (3)	0.4859 (2)	0.7685 (2)	0.0276 (5)
H21A	0.9186	0.4291	0.7709	0.033*
H21B	1.0490	0.4594	0.6956	0.033*
O1B	0.8738 (2)	0.2188 (2)	0.95230 (16)	0.0352 (5)
H10B	0.973 (5)	0.294 (4)	0.992 (3)	0.053*
O2B	0.6672 (3)	0.3147 (2)	1.26097 (16)	0.0362 (5)
O3B	0.6900 (3)	0.1646 (2)	0.72107 (17)	0.0327 (4)
H30B	0.765 (5)	0.162 (3)	0.780 (3)	0.049*
O4B	0.2029 (3)	0.21180 (18)	0.28973 (16)	0.0337 (4)
O5B	0.3954 (2)	0.43956 (18)	0.27052 (16)	0.0311 (4)
H50B	0.487 (5)	0.380 (3)	0.268 (3)	0.047*
C1B	0.7282 (3)	0.2366 (3)	0.9971 (2)	0.0271 (5)
H1B	0.7041	0.3265	0.9900	0.033*
C2B	0.7872 (4)	0.2216 (3)	1.1233 (2)	0.0329 (6)
H2B1	0.8136	0.1337	1.1333	0.039*
H2B2	0.8994	0.2834	1.1646	0.039*
C3B	0.6366 (3)	0.2461 (3)	1.1695 (2)	0.0289 (6)
C4B	0.4543 (3)	0.1831 (2)	1.0997 (2)	0.0274 (5)
H4B	0.3585	0.1787	1.1325	0.033 (8)*
C5B	0.4163 (3)	0.1310 (2)	0.9914 (2)	0.0243 (5)
C6B	0.2300 (3)	0.0576 (2)	0.9262 (2)	0.0263 (5)
H6B1	0.1490	0.0624	0.9740	0.032*
H6B2	0.2393	−0.0338	0.9090	0.032*
C7B	0.1456 (3)	0.1102 (2)	0.8149 (2)	0.0238 (5)
H7B1	0.1120	0.1948	0.8327	0.029*
H7B2	0.0322	0.0516	0.7698	0.029*
C8B	0.2744 (3)	0.1253 (2)	0.74280 (19)	0.0207 (5)
H8B	0.2952	0.0389	0.7150	0.025*
C9B	0.4569 (3)	0.2060 (2)	0.8162 (2)	0.0208 (5)
H9B	0.4219	0.2856	0.8474	0.025*
C10B	0.5527 (3)	0.1440 (2)	0.9252 (2)	0.0230 (5)
C11B	0.5854 (3)	0.2554 (2)	0.7496 (2)	0.0242 (5)
H11B	0.6744	0.3291	0.8004	0.029*
C12B	0.4867 (3)	0.3072 (2)	0.6408 (2)	0.0253 (5)
H12C	0.5711	0.3213	0.5957	0.030*
H12D	0.4549	0.3915	0.6618	0.030*
C13B	0.3127 (3)	0.2186 (2)	0.5666 (2)	0.0208 (5)
C14B	0.1904 (3)	0.1933 (2)	0.6420 (2)	0.0209 (5)
H14B	0.1778	0.2799	0.6751	0.025*
C15B	0.0022 (3)	0.1361 (2)	0.5584 (2)	0.0253 (5)
H15C	−0.0957	0.1555	0.5899	0.030*
H15D	−0.0092	0.0419	0.5410	0.030*
C16B	−0.0081 (3)	0.2016 (3)	0.4511 (2)	0.0278 (5)
H16C	−0.1036	0.2570	0.4379	0.033*
H16D	−0.0370	0.1364	0.3833	0.033*
C17B	0.1828 (3)	0.2829 (2)	0.4741 (2)	0.0234 (5)
H17B	0.1798	0.3709	0.5093	0.028*
C18B	0.3556 (3)	0.0943 (2)	0.5130 (2)	0.0251 (5)
H18D	0.4352	0.1160	0.4673	0.038*
H18E	0.2416	0.0410	0.4644	0.038*
H18F	0.4172	0.0468	0.5735	0.038*
C19B	0.5963 (4)	0.0076 (3)	0.8989 (2)	0.0306 (6)
H19D	0.6452	−0.0272	0.9703	0.046*
H19E	0.6869	0.0129	0.8585	0.046*
H19F	0.4844	−0.0488	0.8513	0.046*
C20B	0.2372 (3)	0.2967 (2)	0.3685 (2)	0.0247 (5)
C21B	0.3426 (4)	0.4267 (2)	0.3687 (2)	0.0277 (5)
H21C	0.2666	0.4930	0.3766	0.033*
H21D	0.4536	0.4438	0.4362	0.033*
O1W	0.1339 (3)	0.4297 (2)	0.06350 (19)	0.0345 (4)
H1W	0.170 (5)	0.460 (3)	0.012 (3)	0.052*
H2W	0.228 (5)	0.422 (3)	0.122 (3)	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0251 (9)	0.0537 (12)	0.0249 (10)	0.0100 (8)	0.0090 (8)	−0.0005 (9)
O2A	0.0366 (10)	0.0437 (12)	0.0226 (10)	0.0003 (8)	0.0068 (8)	0.0014 (9)
O3A	0.0210 (9)	0.0405 (11)	0.0252 (10)	0.0037 (7)	0.0080 (7)	0.0027 (8)
O4A	0.0377 (10)	0.0281 (10)	0.0245 (10)	0.0051 (8)	0.0063 (8)	−0.0006 (8)
O5A	0.0282 (9)	0.0308 (10)	0.0266 (10)	0.0061 (7)	0.0066 (8)	0.0094 (8)
C1A	0.0214 (12)	0.0367 (15)	0.0227 (13)	0.0039 (10)	0.0069 (10)	0.0035 (11)
C2A	0.0347 (14)	0.0391 (16)	0.0243 (14)	0.0029 (11)	0.0124 (11)	0.0020 (12)
C3A	0.0339 (14)	0.0311 (14)	0.0194 (14)	−0.0012 (11)	0.0058 (11)	0.0059 (11)
C4A	0.0269 (12)	0.0328 (14)	0.0267 (14)	0.0034 (10)	0.0059 (11)	0.0085 (12)
C5A	0.0277 (13)	0.0298 (14)	0.0256 (14)	0.0039 (10)	0.0087 (10)	0.0068 (11)
C6A	0.0333 (14)	0.0331 (15)	0.0291 (15)	0.0115 (11)	0.0066 (11)	0.0059 (12)
C7A	0.0275 (13)	0.0297 (14)	0.0274 (14)	0.0100 (10)	0.0080 (11)	0.0044 (11)
C8A	0.0254 (12)	0.0230 (13)	0.0195 (12)	0.0049 (9)	0.0069 (9)	0.0015 (10)
C9A	0.0213 (11)	0.0262 (13)	0.0185 (12)	0.0033 (9)	0.0060 (9)	0.0015 (10)
C10A	0.0258 (12)	0.0278 (13)	0.0203 (13)	0.0038 (10)	0.0077 (10)	0.0055 (10)
C11A	0.0224 (12)	0.0274 (13)	0.0209 (13)	0.0049 (9)	0.0069 (10)	0.0011 (10)
C12A	0.0252 (12)	0.0229 (12)	0.0210 (13)	0.0060 (9)	0.0060 (10)	0.0015 (10)
C13A	0.0231 (12)	0.0209 (12)	0.0160 (12)	0.0038 (9)	0.0067 (9)	0.0032 (9)
C14A	0.0222 (12)	0.0219 (12)	0.0217 (12)	0.0042 (9)	0.0077 (10)	0.0013 (10)
C15A	0.0281 (13)	0.0285 (13)	0.0273 (14)	0.0111 (10)	0.0126 (11)	0.0033 (11)
C16A	0.0346 (14)	0.0318 (14)	0.0288 (15)	0.0097 (11)	0.0173 (12)	0.0049 (12)
C17A	0.0283 (13)	0.0206 (12)	0.0232 (13)	0.0027 (10)	0.0119 (10)	0.0046 (10)
C18A	0.0249 (12)	0.0252 (13)	0.0232 (13)	0.0026 (10)	0.0082 (10)	0.0030 (10)
C19A	0.0339 (14)	0.0344 (15)	0.0263 (14)	−0.0012 (11)	0.0098 (11)	0.0050 (12)
C20A	0.0272 (12)	0.0254 (13)	0.0206 (13)	0.0038 (10)	0.0140 (10)	0.0044 (11)
C21A	0.0269 (12)	0.0258 (14)	0.0282 (14)	0.0022 (10)	0.0071 (10)	0.0034 (11)
O1B	0.0222 (9)	0.0552 (13)	0.0275 (11)	0.0069 (8)	0.0089 (8)	−0.0036 (9)
O2B	0.0342 (10)	0.0495 (12)	0.0243 (10)	0.0123 (9)	0.0070 (8)	0.0006 (9)
O3B	0.0253 (9)	0.0511 (12)	0.0261 (10)	0.0155 (8)	0.0109 (7)	0.0045 (9)
O4B	0.0360 (10)	0.0366 (11)	0.0260 (10)	0.0006 (8)	0.0100 (8)	−0.0014 (9)
O5B	0.0309 (10)	0.0375 (11)	0.0280 (10)	0.0067 (8)	0.0114 (8)	0.0113 (8)
C1B	0.0229 (13)	0.0387 (15)	0.0213 (13)	0.0070 (10)	0.0088 (10)	0.0027 (11)
C2B	0.0261 (13)	0.0469 (17)	0.0247 (14)	0.0101 (11)	0.0051 (11)	0.0035 (12)
C3B	0.0323 (14)	0.0347 (15)	0.0189 (13)	0.0103 (11)	0.0039 (10)	0.0075 (11)
C4B	0.0283 (13)	0.0327 (14)	0.0245 (14)	0.0070 (10)	0.0117 (10)	0.0064 (11)
C5B	0.0248 (12)	0.0234 (13)	0.0273 (14)	0.0076 (9)	0.0091 (10)	0.0082 (10)
C6B	0.0297 (13)	0.0258 (13)	0.0257 (13)	0.0024 (10)	0.0128 (10)	0.0038 (11)
C7B	0.0230 (11)	0.0238 (13)	0.0252 (13)	0.0022 (9)	0.0097 (10)	0.0008 (10)
C8B	0.0202 (11)	0.0210 (12)	0.0204 (12)	0.0033 (9)	0.0060 (9)	0.0018 (10)
C9B	0.0196 (11)	0.0238 (12)	0.0186 (12)	0.0030 (9)	0.0060 (9)	0.0009 (10)
C10B	0.0221 (11)	0.0278 (13)	0.0201 (13)	0.0063 (9)	0.0073 (9)	0.0031 (10)
C11B	0.0191 (11)	0.0328 (14)	0.0203 (13)	0.0030 (9)	0.0065 (9)	0.0025 (11)
C12B	0.0241 (12)	0.0282 (13)	0.0218 (13)	−0.0016 (10)	0.0073 (10)	0.0011 (11)
C13B	0.0193 (11)	0.0205 (12)	0.0210 (13)	0.0012 (9)	0.0056 (9)	−0.0002 (10)
C14B	0.0199 (11)	0.0211 (12)	0.0211 (13)	0.0042 (9)	0.0060 (9)	0.0001 (10)
C15B	0.0202 (12)	0.0297 (14)	0.0245 (13)	0.0043 (9)	0.0043 (10)	0.0050 (10)
C16B	0.0222 (12)	0.0322 (14)	0.0262 (14)	0.0046 (10)	0.0030 (10)	0.0041 (11)
C17B	0.0257 (12)	0.0223 (12)	0.0223 (13)	0.0069 (9)	0.0065 (10)	0.0028 (10)
C18B	0.0253 (12)	0.0286 (13)	0.0221 (13)	0.0082 (10)	0.0079 (10)	−0.0001 (10)
C19B	0.0304 (13)	0.0335 (15)	0.0316 (15)	0.0141 (11)	0.0106 (11)	0.0072 (12)
C20B	0.0237 (12)	0.0288 (14)	0.0199 (13)	0.0065 (9)	0.0030 (10)	0.0045 (11)
C21B	0.0320 (13)	0.0290 (14)	0.0229 (14)	0.0053 (10)	0.0088 (10)	0.0064 (11)
O1W	0.0265 (10)	0.0520 (13)	0.0255 (10)	0.0070 (8)	0.0083 (8)	0.0065 (9)

Geometric parameters (Å, º)

O1A—C1A	1.430 (3)	O1B—H10B	1.01 (4)
O1A—H10A	0.93 (4)	O2B—C3B	1.234 (3)
O2A—C3A	1.232 (3)	O3B—C11B	1.424 (3)
O3A—C11A	1.437 (3)	O3B—H30B	0.79 (4)
O3A—H30A	0.91 (3)	O4B—C20B	1.210 (3)
O4A—C20A	1.206 (3)	O5B—C21B	1.413 (3)
O5A—C21A	1.407 (3)	O5B—H50B	1.01 (3)
O5A—H50A	0.82 (4)	C1B—C2B	1.526 (4)
C1A—C2A	1.529 (4)	C1B—C10B	1.548 (3)
C1A—C10A	1.548 (3)	C1B—H1B	1.0000
C1A—H1A	1.0000	C2B—C3B	1.492 (4)
C2A—C3A	1.502 (4)	C2B—H2B1	0.9900
C2A—H2A1	0.9900	C2B—H2B2	0.9900
C2A—H2A2	0.9900	C3B—C4B	1.458 (4)
C3A—C4A	1.462 (4)	C4B—C5B	1.338 (3)
C4A—C5A	1.340 (4)	C4B—H4B	0.9500
C4A—H4A	0.9500	C5B—C6B	1.502 (4)
C5A—C6A	1.508 (4)	C5B—C10B	1.527 (3)
C5A—C10A	1.529 (3)	C6B—C7B	1.531 (4)
C6A—C7A	1.529 (4)	C6B—H6B1	0.9900
C6A—H6A1	0.9900	C6B—H6B2	0.9900
C6A—H6A2	0.9900	C7B—C8B	1.536 (3)
C7A—C8A	1.536 (3)	C7B—H7B1	0.9900
C7A—H7A1	0.9900	C7B—H7B2	0.9900
C7A—H7A2	0.9900	C8B—C14B	1.519 (3)
C8A—C14A	1.526 (3)	C8B—C9B	1.533 (3)
C8A—C9A	1.543 (3)	C8B—H8B	1.0000
C8A—H8A	1.0000	C9B—C11B	1.550 (3)
C9A—C11A	1.544 (3)	C9B—C10B	1.582 (3)
C9A—C10A	1.581 (3)	C9B—H9B	1.0000
C9A—H9A	1.0000	C10B—C19B	1.555 (4)
C10A—C19A	1.546 (4)	C11B—C12B	1.528 (4)
C11A—C12A	1.539 (3)	C11B—H11B	1.0000
C11A—H11A	1.0000	C12B—C13B	1.529 (3)
C12A—C13A	1.524 (3)	C12B—H12C	0.9900
C12A—H12A	0.9900	C12B—H12D	0.9900
C12A—H12B	0.9900	C13B—C14B	1.539 (3)
C13A—C18A	1.533 (3)	C13B—C18B	1.542 (3)
C13A—C14A	1.541 (3)	C13B—C17B	1.558 (3)
C13A—C17A	1.568 (3)	C14B—C15B	1.529 (3)
C14A—C15A	1.539 (3)	C14B—H14B	1.0000
C14A—H14A	1.0000	C15B—C16B	1.544 (4)
C15A—C16A	1.550 (4)	C15B—H15C	0.9900
C15A—H15A	0.9900	C15B—H15D	0.9900
C15A—H15B	0.9900	C16B—C17B	1.551 (3)
C16A—C17A	1.552 (3)	C16B—H16C	0.9900
C16A—H16A	0.9900	C16B—H16D	0.9900
C16A—H16B	0.9900	C17B—C20B	1.509 (3)
C17A—C20A	1.516 (4)	C17B—H17B	1.0000
C17A—H17A	1.0000	C18B—H18D	0.9800
C18A—H18A	0.9800	C18B—H18E	0.9800
C18A—H18B	0.9800	C18B—H18F	0.9800
C18A—H18C	0.9800	C19B—H19D	0.9800
C19A—H19A	0.9800	C19B—H19E	0.9800
C19A—H19B	0.9800	C19B—H19F	0.9800
C19A—H19C	0.9800	C20B—C21B	1.510 (4)
C20A—C21A	1.513 (4)	C21B—H21C	0.9900
C21A—H21A	0.9900	C21B—H21D	0.9900
C21A—H21B	0.9900	O1W—H1W	0.84 (4)
O1B—C1B	1.430 (3)	O1W—H2W	0.89 (4)
C1A—O1A—H10A	109 (2)	C11B—O3B—H30B	103 (3)
C11A—O3A—H30A	97 (2)	C21B—O5B—H50B	108.8 (19)
C21A—O5A—H50A	110 (2)	O1B—C1B—C2B	109.5 (2)
O1A—C1A—C2A	109.20 (19)	O1B—C1B—C10B	109.65 (19)
O1A—C1A—C10A	109.0 (2)	C2B—C1B—C10B	113.7 (2)
C2A—C1A—C10A	113.2 (2)	O1B—C1B—H1B	107.9
O1A—C1A—H1A	108.5	C2B—C1B—H1B	107.9
C2A—C1A—H1A	108.5	C10B—C1B—H1B	107.9
C10A—C1A—H1A	108.5	C3B—C2B—C1B	108.7 (2)
C3A—C2A—C1A	109.9 (2)	C3B—C2B—H2B1	110.0
C3A—C2A—H2A1	109.7	C1B—C2B—H2B1	110.0
C1A—C2A—H2A1	109.7	C3B—C2B—H2B2	110.0
C3A—C2A—H2A2	109.7	C1B—C2B—H2B2	110.0
C1A—C2A—H2A2	109.7	H2B1—C2B—H2B2	108.3
H2A1—C2A—H2A2	108.2	O2B—C3B—C4B	123.3 (2)
O2A—C3A—C4A	123.4 (2)	O2B—C3B—C2B	121.4 (2)
O2A—C3A—C2A	121.3 (2)	C4B—C3B—C2B	115.3 (2)
C4A—C3A—C2A	115.2 (2)	C5B—C4B—C3B	122.8 (2)
C5A—C4A—C3A	122.8 (2)	C5B—C4B—H4B	118.6
C5A—C4A—H4A	118.6	C3B—C4B—H4B	118.6
C3A—C4A—H4A	118.6	C4B—C5B—C6B	120.7 (2)
C4A—C5A—C6A	120.2 (2)	C4B—C5B—C10B	123.6 (2)
C4A—C5A—C10A	124.1 (2)	C6B—C5B—C10B	115.7 (2)
C6A—C5A—C10A	115.7 (2)	C5B—C6B—C7B	111.9 (2)
C5A—C6A—C7A	113.4 (2)	C5B—C6B—H6B1	109.2
C5A—C6A—H6A1	108.9	C7B—C6B—H6B1	109.2
C7A—C6A—H6A1	108.9	C5B—C6B—H6B2	109.2
C5A—C6A—H6A2	108.9	C7B—C6B—H6B2	109.2
C7A—C6A—H6A2	108.9	H6B1—C6B—H6B2	107.9
H6A1—C6A—H6A2	107.7	C6B—C7B—C8B	113.0 (2)
C6A—C7A—C8A	113.5 (2)	C6B—C7B—H7B1	109.0
C6A—C7A—H7A1	108.9	C8B—C7B—H7B1	109.0
C8A—C7A—H7A1	108.9	C6B—C7B—H7B2	109.0
C6A—C7A—H7A2	108.9	C8B—C7B—H7B2	109.0
C8A—C7A—H7A2	108.9	H7B1—C7B—H7B2	107.8
H7A1—C7A—H7A2	107.7	C14B—C8B—C9B	109.13 (18)
C14A—C8A—C7A	109.43 (19)	C14B—C8B—C7B	109.60 (19)
C14A—C8A—C9A	109.6 (2)	C9B—C8B—C7B	109.01 (18)
C7A—C8A—C9A	108.58 (19)	C14B—C8B—H8B	109.7
C14A—C8A—H8A	109.7	C9B—C8B—H8B	109.7
C7A—C8A—H8A	109.7	C7B—C8B—H8B	109.7
C9A—C8A—H8A	109.7	C8B—C9B—C11B	115.10 (19)
C8A—C9A—C11A	115.81 (19)	C8B—C9B—C10B	112.74 (19)
C8A—C9A—C10A	112.0 (2)	C11B—C9B—C10B	114.64 (18)
C11A—C9A—C10A	114.68 (18)	C8B—C9B—H9B	104.2
C8A—C9A—H9A	104.2	C11B—C9B—H9B	104.2
C11A—C9A—H9A	104.2	C10B—C9B—H9B	104.2
C10A—C9A—H9A	104.2	C5B—C10B—C1B	109.96 (19)
C5A—C10A—C19A	107.5 (2)	C5B—C10B—C19B	107.3 (2)
C5A—C10A—C1A	109.8 (2)	C1B—C10B—C19B	110.7 (2)
C19A—C10A—C1A	110.4 (2)	C5B—C10B—C9B	105.65 (19)
C5A—C10A—C9A	105.12 (18)	C1B—C10B—C9B	108.6 (2)
C19A—C10A—C9A	114.6 (2)	C19B—C10B—C9B	114.4 (2)
C1A—C10A—C9A	109.3 (2)	O3B—C11B—C12B	108.10 (19)
O3A—C11A—C12A	107.48 (19)	O3B—C11B—C9B	114.8 (2)
O3A—C11A—C9A	114.8 (2)	C12B—C11B—C9B	113.38 (19)
C12A—C11A—C9A	112.77 (18)	O3B—C11B—H11B	106.7
O3A—C11A—H11A	107.1	C12B—C11B—H11B	106.7
C12A—C11A—H11A	107.1	C9B—C11B—H11B	106.7
C9A—C11A—H11A	107.1	C11B—C12B—C13B	113.8 (2)
C13A—C12A—C11A	113.25 (19)	C11B—C12B—H12C	108.8
C13A—C12A—H12A	108.9	C13B—C12B—H12C	108.8
C11A—C12A—H12A	108.9	C11B—C12B—H12D	108.8
C13A—C12A—H12B	108.9	C13B—C12B—H12D	108.8
C11A—C12A—H12B	108.9	H12C—C12B—H12D	107.7
H12A—C12A—H12B	107.7	C12B—C13B—C14B	107.00 (19)
C12A—C13A—C18A	111.08 (19)	C12B—C13B—C18B	111.66 (19)
C12A—C13A—C14A	107.59 (19)	C14B—C13B—C18B	112.98 (19)
C18A—C13A—C14A	113.58 (19)	C12B—C13B—C17B	114.7 (2)
C12A—C13A—C17A	115.88 (19)	C14B—C13B—C17B	99.10 (18)
C18A—C13A—C17A	109.36 (19)	C18B—C13B—C17B	110.74 (19)
C14A—C13A—C17A	98.90 (17)	C8B—C14B—C15B	119.6 (2)
C8A—C14A—C15A	118.9 (2)	C8B—C14B—C13B	113.85 (18)
C8A—C14A—C13A	114.51 (18)	C15B—C14B—C13B	104.78 (19)
C15A—C14A—C13A	104.91 (19)	C8B—C14B—H14B	105.8
C8A—C14A—H14A	105.8	C15B—C14B—H14B	105.8
C15A—C14A—H14A	105.8	C13B—C14B—H14B	105.8
C13A—C14A—H14A	105.8	C14B—C15B—C16B	104.34 (19)
C14A—C15A—C16A	103.9 (2)	C14B—C15B—H15C	110.9
C14A—C15A—H15A	111.0	C16B—C15B—H15C	110.9
C16A—C15A—H15A	111.0	C14B—C15B—H15D	110.9
C14A—C15A—H15B	111.0	C16B—C15B—H15D	110.9
C16A—C15A—H15B	111.0	H15C—C15B—H15D	108.9
H15A—C15A—H15B	109.0	C15B—C16B—C17B	106.1 (2)
C15A—C16A—C17A	106.45 (19)	C15B—C16B—H16C	110.5
C15A—C16A—H16A	110.4	C17B—C16B—H16C	110.5
C17A—C16A—H16A	110.4	C15B—C16B—H16D	110.5
C15A—C16A—H16B	110.4	C17B—C16B—H16D	110.5
C17A—C16A—H16B	110.4	H16C—C16B—H16D	108.7
H16A—C16A—H16B	108.6	C20B—C17B—C16B	114.0 (2)
C20A—C17A—C16A	114.6 (2)	C20B—C17B—C13B	115.33 (19)
C20A—C17A—C13A	113.48 (19)	C16B—C17B—C13B	104.09 (19)
C16A—C17A—C13A	103.73 (19)	C20B—C17B—H17B	107.7
C20A—C17A—H17A	108.2	C16B—C17B—H17B	107.7
C16A—C17A—H17A	108.2	C13B—C17B—H17B	107.7
C13A—C17A—H17A	108.2	C13B—C18B—H18D	109.5
C13A—C18A—H18A	109.5	C13B—C18B—H18E	109.5
C13A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
H18A—C18A—H18B	109.5	C13B—C18B—H18F	109.5
C13A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18E—C18B—H18F	109.5
H18B—C18A—H18C	109.5	C10B—C19B—H19D	109.5
C10A—C19A—H19A	109.5	C10B—C19B—H19E	109.5
C10A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
H19A—C19A—H19B	109.5	C10B—C19B—H19F	109.5
C10A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19E—C19B—H19F	109.5
H19B—C19A—H19C	109.5	O4B—C20B—C17B	124.0 (2)
O4A—C20A—C21A	121.4 (2)	O4B—C20B—C21B	121.6 (2)
O4A—C20A—C17A	123.8 (2)	C17B—C20B—C21B	114.4 (2)
C21A—C20A—C17A	114.8 (2)	O5B—C21B—C20B	114.5 (2)
O5A—C21A—C20A	114.8 (2)	O5B—C21B—H21C	108.6
O5A—C21A—H21A	108.6	C20B—C21B—H21C	108.6
C20A—C21A—H21A	108.6	O5B—C21B—H21D	108.6
O5A—C21A—H21B	108.6	C20B—C21B—H21D	108.6
C20A—C21A—H21B	108.6	H21C—C21B—H21D	107.6
H21A—C21A—H21B	107.6	H1W—O1W—H2W	111 (3)
C1B—O1B—H10B	105 (2)
O1A—C1A—C2A—C3A	179.5 (2)	O1B—C1B—C2B—C3B	177.6 (2)
C10A—C1A—C2A—C3A	−58.9 (3)	C10B—C1B—C2B—C3B	−59.4 (3)
C1A—C2A—C3A—O2A	−139.3 (3)	C1B—C2B—C3B—O2B	−134.7 (3)
C1A—C2A—C3A—C4A	42.7 (3)	C1B—C2B—C3B—C4B	45.7 (3)
O2A—C3A—C4A—C5A	171.4 (3)	O2B—C3B—C4B—C5B	166.0 (3)
C2A—C3A—C4A—C5A	−10.6 (4)	C2B—C3B—C4B—C5B	−14.4 (4)
C3A—C4A—C5A—C6A	171.9 (2)	C3B—C4B—C5B—C6B	174.9 (2)
C3A—C4A—C5A—C10A	−7.9 (4)	C3B—C4B—C5B—C10B	−6.7 (4)
C4A—C5A—C6A—C7A	130.2 (3)	C4B—C5B—C6B—C7B	125.3 (2)
C10A—C5A—C6A—C7A	−50.0 (3)	C10B—C5B—C6B—C7B	−53.2 (3)
C5A—C6A—C7A—C8A	46.8 (3)	C5B—C6B—C7B—C8B	50.4 (3)
C6A—C7A—C8A—C14A	−171.8 (2)	C6B—C7B—C8B—C14B	−172.86 (19)
C6A—C7A—C8A—C9A	−52.2 (3)	C6B—C7B—C8B—C9B	−53.5 (3)
C14A—C8A—C9A—C11A	−45.1 (3)	C14B—C8B—C9B—C11B	−47.2 (3)
C7A—C8A—C9A—C11A	−164.6 (2)	C7B—C8B—C9B—C11B	−166.9 (2)
C14A—C8A—C9A—C10A	−179.20 (18)	C14B—C8B—C9B—C10B	178.70 (18)
C7A—C8A—C9A—C10A	61.3 (2)	C7B—C8B—C9B—C10B	59.0 (2)
C4A—C5A—C10A—C19A	112.4 (3)	C4B—C5B—C10B—C1B	−6.2 (3)
C6A—C5A—C10A—C19A	−67.4 (3)	C6B—C5B—C10B—C1B	172.3 (2)
C4A—C5A—C10A—C1A	−7.7 (3)	C4B—C5B—C10B—C19B	114.3 (3)
C6A—C5A—C10A—C1A	172.5 (2)	C6B—C5B—C10B—C19B	−67.2 (3)
C4A—C5A—C10A—C9A	−125.2 (3)	C4B—C5B—C10B—C9B	−123.2 (2)
C6A—C5A—C10A—C9A	55.1 (3)	C6B—C5B—C10B—C9B	55.3 (3)
O1A—C1A—C10A—C5A	162.5 (2)	O1B—C1B—C10B—C5B	162.3 (2)
C2A—C1A—C10A—C5A	40.8 (3)	C2B—C1B—C10B—C5B	39.4 (3)
O1A—C1A—C10A—C19A	44.2 (3)	O1B—C1B—C10B—C19B	43.9 (3)
C2A—C1A—C10A—C19A	−77.5 (3)	C2B—C1B—C10B—C19B	−79.1 (3)
O1A—C1A—C10A—C9A	−82.7 (2)	O1B—C1B—C10B—C9B	−82.5 (2)
C2A—C1A—C10A—C9A	155.6 (2)	C2B—C1B—C10B—C9B	154.5 (2)
C8A—C9A—C10A—C5A	−61.3 (2)	C8B—C9B—C10B—C5B	−58.4 (2)
C11A—C9A—C10A—C5A	164.1 (2)	C11B—C9B—C10B—C5B	167.30 (19)
C8A—C9A—C10A—C19A	56.5 (3)	C8B—C9B—C10B—C1B	−176.33 (18)
C11A—C9A—C10A—C19A	−78.1 (3)	C11B—C9B—C10B—C1B	49.4 (3)
C8A—C9A—C10A—C1A	−179.05 (19)	C8B—C9B—C10B—C19B	59.4 (3)
C11A—C9A—C10A—C1A	46.3 (3)	C11B—C9B—C10B—C19B	−74.9 (3)
C8A—C9A—C11A—O3A	−79.7 (3)	C8B—C9B—C11B—O3B	−81.7 (3)
C10A—C9A—C11A—O3A	53.1 (3)	C10B—C9B—C11B—O3B	51.5 (3)
C8A—C9A—C11A—C12A	43.8 (3)	C8B—C9B—C11B—C12B	43.3 (3)
C10A—C9A—C11A—C12A	176.62 (19)	C10B—C9B—C11B—C12B	176.5 (2)
O3A—C11A—C12A—C13A	77.5 (2)	O3B—C11B—C12B—C13B	80.7 (2)
C9A—C11A—C12A—C13A	−49.9 (3)	C9B—C11B—C12B—C13B	−47.8 (3)
C11A—C12A—C13A—C18A	−68.1 (3)	C11B—C12B—C13B—C14B	55.4 (3)
C11A—C12A—C13A—C14A	56.8 (2)	C11B—C12B—C13B—C18B	−68.7 (3)
C11A—C12A—C13A—C17A	166.31 (19)	C11B—C12B—C13B—C17B	164.24 (19)
C7A—C8A—C14A—C15A	−61.4 (3)	C9B—C8B—C14B—C15B	−176.83 (19)
C9A—C8A—C14A—C15A	179.6 (2)	C7B—C8B—C14B—C15B	−57.5 (3)
C7A—C8A—C14A—C13A	173.54 (19)	C9B—C8B—C14B—C13B	58.2 (2)
C9A—C8A—C14A—C13A	54.6 (3)	C7B—C8B—C14B—C13B	177.55 (19)
C12A—C13A—C14A—C8A	−60.7 (2)	C12B—C13B—C14B—C8B	−62.2 (2)
C18A—C13A—C14A—C8A	62.7 (3)	C18B—C13B—C14B—C8B	61.1 (3)
C17A—C13A—C14A—C8A	178.42 (19)	C17B—C13B—C14B—C8B	178.33 (18)
C12A—C13A—C14A—C15A	167.15 (19)	C12B—C13B—C14B—C15B	165.29 (19)
C18A—C13A—C14A—C15A	−69.5 (2)	C18B—C13B—C14B—C15B	−71.4 (2)
C17A—C13A—C14A—C15A	46.3 (2)	C17B—C13B—C14B—C15B	45.8 (2)
C8A—C14A—C15A—C16A	−162.1 (2)	C8B—C14B—C15B—C16B	−161.64 (19)
C13A—C14A—C15A—C16A	−32.5 (2)	C13B—C14B—C15B—C16B	−32.5 (2)
C14A—C15A—C16A—C17A	5.0 (3)	C14B—C15B—C16B—C17B	5.6 (2)
C15A—C16A—C17A—C20A	147.8 (2)	C15B—C16B—C17B—C20B	149.3 (2)
C15A—C16A—C17A—C13A	23.5 (2)	C15B—C16B—C17B—C13B	22.8 (2)
C12A—C13A—C17A—C20A	78.3 (3)	C12B—C13B—C17B—C20B	79.3 (3)
C18A—C13A—C17A—C20A	−48.2 (3)	C14B—C13B—C17B—C20B	−167.1 (2)
C14A—C13A—C17A—C20A	−167.17 (19)	C18B—C13B—C17B—C20B	−48.2 (3)
C12A—C13A—C17A—C16A	−156.7 (2)	C12B—C13B—C17B—C16B	−155.0 (2)
C18A—C13A—C17A—C16A	76.8 (2)	C14B—C13B—C17B—C16B	−41.5 (2)
C14A—C13A—C17A—C16A	−42.1 (2)	C18B—C13B—C17B—C16B	77.5 (2)
C16A—C17A—C20A—O4A	−31.9 (3)	C16B—C17B—C20B—O4B	−37.9 (3)
C13A—C17A—C20A—O4A	87.0 (3)	C13B—C17B—C20B—O4B	82.5 (3)
C16A—C17A—C20A—C21A	148.9 (2)	C16B—C17B—C20B—C21B	143.0 (2)
C13A—C17A—C20A—C21A	−92.1 (2)	C13B—C17B—C20B—C21B	−96.7 (3)
O4A—C20A—C21A—O5A	−2.4 (3)	O4B—C20B—C21B—O5B	0.2 (4)
C17A—C20A—C21A—O5A	176.80 (19)	C17B—C20B—C21B—O5B	179.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H10A···O1W^i	0.93 (4)	1.84 (4)	2.759 (3)	174 (3)
O3A—H30A···O1A	0.91 (3)	1.88 (3)	2.738 (3)	158 (3)
O5A—H50A···O2A^ii	0.82 (4)	1.89 (4)	2.687 (3)	163 (3)
O1B—H10B···O1W^ii	1.01 (4)	1.75 (4)	2.760 (3)	176 (3)
O3B—H30B···O1B	0.79 (4)	2.06 (4)	2.768 (3)	150 (3)
O5B—H50B···O2B^iii	1.01 (3)	1.67 (3)	2.659 (3)	166 (3)
O1W—H1W···O5A^iv	0.84 (4)	1.95 (4)	2.733 (3)	156 (3)
O1W—H2W···O5B	0.89 (4)	1.89 (4)	2.743 (3)	162 (3)

Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) x, y, z−1; (iv) x−1, y, z−1.