Solid forms and β-cyclo­dextrin com­plexation of turinabol

4-Chloro-17β-hy­droxy-17α-methyl­androsta-1,4-dien-3-one (C₂₀H₂₇ClO₂), known as turinabol, is a synthetic anabolic–androgenic agent which belongs to the steroid class. Recrystallization from various solvents was performed and the following new solid forms of turinabol were obtained: the hemihydrate (C₂₀H₂₇ClO₂·0.5H₂O), the anhydrous form (C₂₀H₂₇ClO₂), the multicom­ponent acetic acid hydrate (2C₂₀H₂₇ClO₂·C₂H₄O₂·H₂O) and the 2,2,2-tri­fluoro­ethanol hemisolvate (C₂₀H₂₇ClO₂·0.5C₂H₃F₃O). The absolute structures were determined by single-crystal X-ray diffraction. The starting hemihydrate form contains one turinabol mol­ecule in the asymmetric unit, while the others contain two mol­ecules in the asymmetric unit. Structural features were investigated in terms of the conformational analysis of the steroid skeleton rings and inter­molecular inter­actions. The magnitudes, the nature of the crystal structure energies and the inter­molecular inter­actions were also evaluated. Complexation with β-cyclo­dextrin was performed and the obtained com­plex was investigated using powder X-ray diffraction, Fourier-transform infrared (FT–IR) spectroscopy and differential thermal analysis/thermogravimetric analysis (DTA/TGA).

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018) for TBOL1, TBOL2, TBOL3; CrysAlis PRO (Rigaku OD, 2019) for TBOL4. Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for TBOL1, TBOL2, TBOL3; CrysAlis PRO (Rigaku OD, 2019) for TBOL4. Data reduction: CrysAlis PRO (Rigaku OD, 2018) for TBOL1, TBOL2, TBOL3; CrysAlis PRO (Rigaku OD, 2019) for TBOL4. Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for TBOL1; SHELXT (Sheldrick, 2015a) for TBOL2; SHELXS (Sheldrick, 2008) for TBOL3, TBOL4. For all structures, program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one hemihydrate (TBOL1)

Crystal data

C20H27ClO2·0.5H2O	Dx = 1.238 Mg m^−3
Mr = 343.87	Cu Kα radiation, λ = 1.54184 Å
Trigonal, P3121	Cell parameters from 23373 reflections
a = 10.5989 (1) Å	θ = 4.7–70.4°
c = 28.4478 (2) Å	µ = 1.91 mm^−1
V = 2767.58 (6) Å^3	T = 293 K
Z = 6	Block, colourless
F(000) = 1110	0.15 × 0.1 × 0.1 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	3528 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3429 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.024
Detector resolution: 16.4335 pixels mm^-1	θmax = 70.6°, θmin = 4.7°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −12→12
Tmin = 0.859, Tmax = 1.000	l = −34→34
40408 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.3945P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.17 e Å^−3
3528 reflections	Δρmin = −0.25 e Å^−3
221 parameters	Absolute structure: Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.008 (3)
Primary atom site location: iterative

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cl1	0.11422 (8)	0.47769 (7)	0.60134 (2)	0.0705 (2)
O2	0.79425 (16)	0.77704 (17)	0.33300 (5)	0.0482 (3)
H2	0.882116	0.833733	0.330884	0.072*
O3	0.000000	0.1040 (2)	0.666667	0.0643 (7)
C17	0.7520 (2)	0.7584 (2)	0.38156 (6)	0.0372 (4)
C13	0.58332 (19)	0.68269 (19)	0.38527 (6)	0.0342 (4)
C4	0.1017 (2)	0.4178 (2)	0.54388 (7)	0.0423 (4)
O1	−0.0237 (3)	0.1766 (2)	0.57266 (6)	0.0903 (7)
C14	0.5650 (2)	0.72662 (19)	0.43540 (6)	0.0355 (4)
H14	0.596538	0.675751	0.457015	0.043*
C5	0.1566 (2)	0.5091 (2)	0.50743 (6)	0.0394 (4)
C8	0.4083 (2)	0.6787 (2)	0.44800 (6)	0.0373 (4)
H8	0.370754	0.721533	0.425327	0.045*
C10	0.1526 (2)	0.4531 (2)	0.45796 (6)	0.0415 (4)
C9	0.3172 (2)	0.5117 (2)	0.44414 (6)	0.0360 (4)
H9	0.356330	0.472939	0.467724	0.043*
C16	0.8035 (2)	0.9064 (2)	0.40632 (7)	0.0490 (5)
H16A	0.890515	0.933479	0.424650	0.059*
H16B	0.825814	0.982014	0.383196	0.059*
C11	0.3362 (2)	0.4554 (2)	0.39604 (7)	0.0491 (5)
H11A	0.287889	0.349845	0.396913	0.059*
H11B	0.289449	0.482473	0.371936	0.059*
C18	0.5283 (3)	0.7483 (3)	0.34765 (7)	0.0523 (5)
H18A	0.580739	0.852527	0.350282	0.078*
H18B	0.426218	0.712481	0.352239	0.078*
H18C	0.543732	0.720628	0.316976	0.078*
C12	0.4969 (2)	0.5163 (2)	0.38289 (7)	0.0451 (5)
H12A	0.540012	0.476910	0.404167	0.054*
H12B	0.502788	0.485254	0.351296	0.054*
C3	0.0261 (3)	0.2582 (2)	0.53918 (7)	0.0524 (5)
C1	0.0706 (2)	0.2909 (3)	0.45523 (7)	0.0534 (6)
H1	0.059096	0.248492	0.425761	0.064*
C2	0.0133 (3)	0.2035 (2)	0.49155 (8)	0.0563 (6)
H2A	−0.037112	0.103331	0.486565	0.068*
C15	0.6793 (2)	0.8890 (2)	0.43859 (8)	0.0524 (5)
H15A	0.713312	0.916118	0.470644	0.063*
H15B	0.639493	0.948685	0.427728	0.063*
C6	0.2384 (3)	0.6713 (2)	0.51233 (8)	0.0537 (5)
H6A	0.235200	0.698137	0.544724	0.064*
H6B	0.194106	0.713501	0.492748	0.064*
C22	0.8177 (2)	0.6756 (3)	0.40503 (9)	0.0575 (6)
H22A	0.781304	0.582555	0.390072	0.086*
H22B	0.791454	0.661548	0.437691	0.086*
H22C	0.921868	0.730363	0.402134	0.086*
C7	0.3961 (2)	0.7287 (2)	0.49730 (8)	0.0501 (5)
H7A	0.442648	0.695624	0.519551	0.060*
H7B	0.447677	0.834383	0.498154	0.060*
C19	0.0769 (3)	0.5063 (4)	0.42336 (8)	0.0659 (7)
H19A	−0.021032	0.472952	0.433722	0.099*
H19B	0.074943	0.468209	0.392590	0.099*
H19C	0.129585	0.610841	0.422258	0.099*
H3	−0.008 (5)	0.153 (4)	0.6447 (11)	0.110 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0943 (5)	0.0732 (4)	0.0334 (2)	0.0339 (4)	0.0052 (3)	−0.0089 (2)
O2	0.0472 (7)	0.0558 (9)	0.0353 (7)	0.0210 (7)	0.0066 (6)	−0.0006 (6)
O3	0.093 (2)	0.0617 (10)	0.0484 (12)	0.0465 (10)	−0.0065 (13)	−0.0033 (6)
C17	0.0377 (9)	0.0389 (9)	0.0304 (8)	0.0157 (8)	0.0007 (7)	0.0014 (7)
C13	0.0359 (9)	0.0348 (9)	0.0300 (8)	0.0163 (8)	−0.0029 (7)	−0.0029 (7)
C4	0.0446 (10)	0.0460 (10)	0.0326 (8)	0.0200 (9)	−0.0014 (7)	−0.0037 (8)
O1	0.1275 (19)	0.0553 (10)	0.0542 (10)	0.0204 (12)	0.0092 (11)	0.0153 (8)
C14	0.0373 (9)	0.0314 (9)	0.0310 (8)	0.0122 (8)	−0.0019 (7)	−0.0038 (7)
C5	0.0375 (9)	0.0419 (10)	0.0369 (9)	0.0184 (8)	0.0027 (7)	−0.0020 (7)
C8	0.0423 (10)	0.0338 (9)	0.0338 (9)	0.0176 (8)	0.0007 (7)	−0.0017 (7)
C10	0.0354 (9)	0.0501 (11)	0.0307 (8)	0.0151 (9)	−0.0012 (7)	−0.0024 (8)
C9	0.0355 (9)	0.0357 (9)	0.0302 (8)	0.0130 (8)	−0.0029 (7)	−0.0058 (7)
C16	0.0437 (11)	0.0401 (10)	0.0461 (11)	0.0081 (9)	0.0065 (9)	−0.0049 (8)
C11	0.0407 (10)	0.0466 (11)	0.0431 (10)	0.0091 (9)	0.0010 (9)	−0.0172 (9)
C18	0.0525 (12)	0.0723 (15)	0.0387 (10)	0.0363 (11)	−0.0029 (9)	0.0072 (10)
C12	0.0444 (11)	0.0385 (10)	0.0446 (10)	0.0149 (9)	0.0039 (9)	−0.0126 (8)
C3	0.0545 (12)	0.0472 (11)	0.0428 (10)	0.0159 (10)	0.0017 (9)	0.0032 (9)
C1	0.0395 (10)	0.0546 (12)	0.0412 (10)	0.0048 (10)	−0.0007 (8)	−0.0169 (9)
C2	0.0473 (12)	0.0417 (11)	0.0563 (12)	0.0046 (9)	0.0041 (10)	−0.0104 (9)
C15	0.0506 (12)	0.0363 (10)	0.0514 (11)	0.0076 (9)	0.0091 (10)	−0.0088 (9)
C6	0.0627 (14)	0.0413 (11)	0.0543 (12)	0.0240 (10)	0.0181 (11)	−0.0027 (9)
C22	0.0439 (12)	0.0626 (14)	0.0679 (14)	0.0281 (11)	0.0024 (11)	0.0154 (12)
C7	0.0528 (12)	0.0350 (10)	0.0477 (11)	0.0107 (9)	0.0096 (9)	−0.0118 (9)
C19	0.0453 (12)	0.105 (2)	0.0468 (11)	0.0373 (13)	0.0007 (10)	0.0128 (13)

Geometric parameters (Å, º)

Cl1—C4	1.7344 (19)	C5—C10	1.520 (2)
O2—C17	1.435 (2)	C5—C6	1.495 (3)
C17—C13	1.554 (2)	C8—C9	1.539 (2)
C17—C16	1.549 (3)	C8—C7	1.527 (3)
C17—C22	1.521 (3)	C10—C9	1.582 (3)
C13—C14	1.542 (2)	C10—C1	1.491 (3)
C13—C18	1.541 (3)	C10—C19	1.544 (3)
C13—C12	1.529 (3)	C9—C11	1.546 (2)
C4—C5	1.337 (3)	C16—C15	1.538 (3)
C4—C3	1.472 (3)	C11—C12	1.535 (3)
O1—C3	1.215 (3)	C3—C2	1.453 (3)
C14—C8	1.518 (3)	C1—C2	1.316 (3)
C14—C15	1.533 (3)	C6—C7	1.526 (3)
O2—C17—C13	109.61 (14)	C14—C8—C7	111.67 (16)
O2—C17—C16	111.76 (15)	C7—C8—C9	110.58 (15)
O2—C17—C22	107.49 (17)	C5—C10—C9	105.47 (14)
C16—C17—C13	102.93 (15)	C5—C10—C19	111.48 (18)
C22—C17—C13	114.37 (16)	C1—C10—C5	112.63 (16)
C22—C17—C16	110.73 (17)	C1—C10—C9	109.40 (17)
C14—C13—C17	101.11 (13)	C1—C10—C19	106.14 (18)
C18—C13—C17	108.47 (15)	C19—C10—C9	111.80 (16)
C18—C13—C14	111.91 (16)	C8—C9—C10	111.57 (16)
C12—C13—C17	117.63 (15)	C8—C9—C11	112.31 (15)
C12—C13—C14	107.21 (14)	C11—C9—C10	113.54 (14)
C12—C13—C18	110.23 (16)	C15—C16—C17	107.61 (16)
C5—C4—Cl1	122.68 (16)	C12—C11—C9	112.60 (16)
C5—C4—C3	123.46 (18)	C13—C12—C11	111.94 (16)
C3—C4—Cl1	113.86 (15)	O1—C3—C4	122.6 (2)
C8—C14—C13	113.54 (14)	O1—C3—C2	121.8 (2)
C8—C14—C15	118.66 (17)	C2—C3—C4	115.59 (19)
C15—C14—C13	104.21 (15)	C2—C1—C10	124.66 (18)
C4—C5—C10	121.24 (18)	C1—C2—C3	122.2 (2)
C4—C5—C6	123.52 (18)	C14—C15—C16	104.36 (16)
C6—C5—C10	114.97 (17)	C5—C6—C7	108.81 (17)
C14—C8—C9	108.64 (15)	C6—C7—C8	112.62 (18)

4-Chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one (TBOL2)

Crystal data

C20H27ClO2	F(000) = 720
Mr = 334.86	Dx = 1.221 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 10.8409 (3) Å	Cell parameters from 11218 reflections
b = 10.2250 (2) Å	θ = 4.1–69.9°
c = 16.4751 (5) Å	µ = 1.90 mm^−1
β = 93.759 (2)°	T = 293 K
V = 1822.31 (8) Å^3	Block, colourless
Z = 4	0.18 × 0.11 × 0.10 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	6891 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	6235 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 16.4335 pixels mm^-1	θmax = 70.8°, θmin = 4.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −12→12
Tmin = 0.922, Tmax = 1.000	l = −20→19
26247 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0897P)^2 + 0.0816P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.68 e Å^−3
6891 reflections	Δρmin = −0.21 e Å^−3
423 parameters	Absolute structure: Flack x determined using 2594 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.010 (5)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cl1B	0.05772 (9)	0.66389 (9)	0.60807 (6)	0.0563 (2)
Cl1A	−0.23673 (11)	0.46894 (11)	0.72554 (8)	0.0769 (3)
O1B	0.2885 (3)	0.6089 (3)	0.53697 (18)	0.0701 (8)
O2B	0.3276 (3)	0.1126 (3)	1.0874 (2)	0.0738 (9)
H2B	0.304316	0.042733	1.105446	0.111*
O2A	0.5272 (3)	0.0219 (4)	0.5785 (3)	0.0902 (11)
H2A	0.584047	0.050918	0.553386	0.135*
O1A	−0.2431 (3)	0.3287 (4)	0.8775 (2)	0.0855 (11)
C8B	0.1975 (3)	0.4553 (3)	0.8893 (2)	0.0417 (7)
H8B	0.213544	0.521523	0.931677	0.050*
C7B	0.0814 (3)	0.4935 (4)	0.8374 (2)	0.0461 (7)
H7BA	0.063161	0.426176	0.796962	0.055*
H7BB	0.012225	0.498135	0.871840	0.055*
C9B	0.3084 (3)	0.4503 (3)	0.8357 (2)	0.0402 (7)
H9B	0.287151	0.385786	0.793076	0.048*
C5B	0.2042 (3)	0.6167 (3)	0.7438 (2)	0.0437 (7)
C10B	0.3264 (3)	0.5842 (4)	0.7906 (2)	0.0481 (8)
C12A	0.2939 (3)	0.0223 (4)	0.6999 (2)	0.0542 (9)
H12C	0.326294	0.083297	0.741135	0.065*
H12D	0.337169	−0.060066	0.708400	0.065*
C4B	0.1959 (3)	0.6277 (3)	0.6628 (2)	0.0443 (7)
C3B	0.3010 (4)	0.6053 (4)	0.6119 (2)	0.0514 (8)
C13A	0.3178 (3)	0.0754 (3)	0.6161 (2)	0.0477 (8)
C4A	−0.1767 (3)	0.3127 (4)	0.7440 (3)	0.0542 (9)
C13B	0.3004 (3)	0.2767 (4)	0.9800 (2)	0.0462 (7)
C11B	0.4262 (3)	0.3996 (4)	0.8821 (2)	0.0518 (9)
H11A	0.490719	0.389657	0.844376	0.062*
H11B	0.454200	0.463470	0.922719	0.062*
C14B	0.1836 (3)	0.3229 (3)	0.9296 (2)	0.0436 (7)
H14B	0.168117	0.259083	0.885675	0.052*
C11A	0.1548 (3)	0.0012 (4)	0.7095 (2)	0.0508 (8)
H11C	0.124379	−0.066817	0.672293	0.061*
H11D	0.142758	−0.027994	0.764423	0.061*
C12B	0.4058 (3)	0.2687 (4)	0.9237 (3)	0.0537 (9)
H12A	0.387098	0.202254	0.882696	0.064*
H12B	0.480964	0.243188	0.954787	0.064*
C18A	0.2843 (4)	−0.0283 (4)	0.5511 (3)	0.0631 (10)
H18D	0.328851	−0.107460	0.564211	0.095*
H18E	0.306114	0.003037	0.498977	0.095*
H18F	0.197128	−0.045266	0.549364	0.095*
C14A	0.2414 (3)	0.2016 (3)	0.6023 (2)	0.0471 (8)
H14A	0.268037	0.261487	0.646428	0.056*
C5A	−0.1207 (3)	0.2466 (4)	0.6874 (2)	0.0513 (8)
C9A	0.0803 (3)	0.1268 (3)	0.6922 (2)	0.0408 (7)
H9A	0.112698	0.191689	0.731839	0.049*
C17B	0.2525 (4)	0.1454 (4)	1.0147 (2)	0.0566 (9)
C1B	0.4297 (4)	0.5699 (5)	0.7356 (3)	0.0630 (11)
H1B	0.508384	0.554409	0.759641	0.076*
C6B	0.0944 (4)	0.6242 (4)	0.7947 (2)	0.0518 (8)
H6BA	0.020221	0.642837	0.760518	0.062*
H6BB	0.106038	0.693743	0.834551	0.062*
C6A	−0.1027 (4)	0.2993 (5)	0.6049 (3)	0.0629 (10)
H6AA	−0.141443	0.384553	0.598996	0.076*
H6AB	−0.141533	0.241556	0.564106	0.076*
C10A	−0.0628 (3)	0.1122 (4)	0.7056 (2)	0.0489 (8)
C1A	−0.0789 (4)	0.0686 (4)	0.7900 (3)	0.0602 (10)
H1A	−0.044097	−0.011163	0.806179	0.072*
C8A	0.1035 (3)	0.1827 (3)	0.6072 (2)	0.0444 (7)
H8A	0.074056	0.119486	0.565649	0.053*
C3A	−0.1913 (4)	0.2658 (5)	0.8263 (3)	0.0634 (11)
C17A	0.4506 (4)	0.1272 (4)	0.6019 (3)	0.0665 (12)
C18B	0.3354 (4)	0.3699 (4)	1.0514 (3)	0.0590 (9)
H18A	0.345892	0.456849	1.030962	0.088*
H18B	0.411297	0.341127	1.079081	0.088*
H18C	0.270926	0.369756	1.088635	0.088*
C19A	−0.1243 (4)	0.0099 (4)	0.6481 (3)	0.0663 (11)
H19D	−0.212526	0.016641	0.649083	0.100*
H19E	−0.098328	−0.075963	0.665357	0.100*
H19F	−0.100541	0.025150	0.593749	0.100*
C15B	0.0804 (4)	0.3055 (5)	0.9877 (3)	0.0605 (10)
H15A	0.000773	0.294655	0.958060	0.073*
H15B	0.076410	0.379675	1.024152	0.073*
C2B	0.4181 (4)	0.5774 (5)	0.6557 (3)	0.0661 (11)
H2BA	0.487491	0.564357	0.626358	0.079*
C19B	0.3610 (5)	0.6953 (4)	0.8516 (3)	0.0677 (12)
H19A	0.305757	0.693797	0.894809	0.102*
H19B	0.354470	0.778040	0.824126	0.102*
H19C	0.444334	0.683010	0.873765	0.102*
C7A	0.0355 (4)	0.3111 (4)	0.5921 (3)	0.0570 (9)
H7AA	0.045909	0.339498	0.536760	0.068*
H7AB	0.071679	0.377173	0.628584	0.068*
C2A	−0.1396 (4)	0.1353 (5)	0.8444 (3)	0.0690 (12)
H2AA	−0.149419	0.098314	0.895153	0.083*
C16B	0.1186 (4)	0.1801 (5)	1.0349 (3)	0.0696 (12)
H16A	0.062973	0.109002	1.018897	0.084*
H16B	0.115066	0.194393	1.092897	0.084*
C15A	0.2889 (5)	0.2593 (5)	0.5239 (3)	0.0710 (12)
H15C	0.249196	0.218123	0.476023	0.085*
H15D	0.274964	0.352888	0.520959	0.085*
C20B	0.2559 (6)	0.0309 (5)	0.9562 (3)	0.0824 (15)
H20A	0.340218	0.007747	0.948810	0.124*
H20B	0.215535	0.054986	0.904797	0.124*
H20C	0.213980	−0.042567	0.978130	0.124*
C16A	0.4272 (5)	0.2277 (5)	0.5322 (4)	0.0884 (17)
H16C	0.474292	0.306762	0.544377	0.106*
H16D	0.453236	0.191653	0.481649	0.106*
C20A	0.5145 (5)	0.1903 (7)	0.6777 (4)	0.100 (2)
H20D	0.533237	0.124356	0.718142	0.150*
H20E	0.460754	0.254599	0.699038	0.150*
H20F	0.589724	0.231639	0.663611	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1B	0.0591 (5)	0.0552 (5)	0.0529 (5)	0.0043 (4)	−0.0092 (4)	0.0074 (4)
Cl1A	0.0611 (6)	0.0684 (6)	0.1005 (8)	0.0216 (5)	0.0000 (5)	−0.0194 (6)
O1B	0.083 (2)	0.0773 (19)	0.0507 (16)	0.0064 (17)	0.0133 (14)	0.0067 (14)
O2B	0.0728 (19)	0.076 (2)	0.0708 (19)	−0.0097 (16)	−0.0119 (15)	0.0335 (16)
O2A	0.071 (2)	0.072 (2)	0.132 (3)	0.0072 (17)	0.050 (2)	−0.012 (2)
O1A	0.081 (2)	0.097 (3)	0.081 (2)	0.0141 (19)	0.0229 (18)	−0.026 (2)
C8B	0.0408 (16)	0.0454 (17)	0.0392 (15)	0.0023 (13)	0.0037 (13)	−0.0004 (13)
C7B	0.0368 (16)	0.058 (2)	0.0443 (17)	0.0071 (14)	0.0064 (13)	0.0023 (15)
C9B	0.0367 (16)	0.0417 (16)	0.0425 (16)	−0.0018 (13)	0.0035 (13)	0.0009 (13)
C5B	0.0434 (17)	0.0394 (15)	0.0482 (18)	0.0016 (13)	0.0021 (14)	0.0064 (14)
C10B	0.0435 (18)	0.0518 (19)	0.0488 (19)	−0.0022 (15)	0.0006 (15)	0.0077 (15)
C12A	0.0456 (19)	0.057 (2)	0.060 (2)	0.0090 (17)	0.0031 (16)	−0.0002 (18)
C4B	0.0475 (17)	0.0383 (16)	0.0467 (17)	0.0014 (13)	−0.0009 (14)	0.0058 (13)
C3B	0.063 (2)	0.0445 (18)	0.0479 (19)	0.0021 (16)	0.0129 (16)	0.0076 (15)
C13A	0.0464 (18)	0.0419 (16)	0.056 (2)	−0.0028 (14)	0.0124 (15)	−0.0087 (15)
C4A	0.0349 (16)	0.059 (2)	0.068 (2)	0.0030 (15)	−0.0020 (15)	−0.0156 (18)
C13B	0.0441 (18)	0.0476 (18)	0.0464 (18)	0.0005 (14)	−0.0001 (14)	0.0078 (15)
C11B	0.0386 (18)	0.059 (2)	0.058 (2)	0.0039 (15)	0.0042 (16)	0.0139 (17)
C14B	0.0421 (17)	0.0490 (18)	0.0394 (16)	−0.0002 (14)	0.0020 (13)	0.0043 (14)
C11A	0.0503 (19)	0.049 (2)	0.054 (2)	0.0046 (16)	0.0102 (15)	0.0034 (15)
C12B	0.0458 (18)	0.054 (2)	0.062 (2)	0.0103 (16)	0.0071 (16)	0.0123 (17)
C18A	0.071 (3)	0.052 (2)	0.068 (2)	−0.0051 (19)	0.014 (2)	−0.0180 (19)
C14A	0.055 (2)	0.0402 (16)	0.0475 (18)	−0.0040 (14)	0.0116 (15)	−0.0079 (13)
C5A	0.0394 (17)	0.055 (2)	0.058 (2)	0.0031 (15)	−0.0045 (15)	−0.0115 (16)
C9A	0.0411 (16)	0.0409 (16)	0.0404 (16)	0.0000 (12)	0.0022 (13)	−0.0047 (12)
C17B	0.058 (2)	0.059 (2)	0.052 (2)	−0.0076 (18)	−0.0035 (16)	0.0190 (17)
C1B	0.0383 (18)	0.076 (3)	0.074 (3)	−0.0034 (18)	0.0043 (18)	0.029 (2)
C6B	0.0509 (19)	0.059 (2)	0.0457 (18)	0.0159 (16)	0.0041 (15)	0.0013 (15)
C6A	0.068 (3)	0.065 (2)	0.054 (2)	0.021 (2)	−0.0091 (18)	−0.0028 (18)
C10A	0.0424 (17)	0.0498 (19)	0.055 (2)	0.0021 (15)	0.0038 (15)	−0.0074 (16)
C1A	0.055 (2)	0.059 (2)	0.068 (3)	0.0039 (18)	0.0152 (19)	0.0067 (19)
C8A	0.0512 (18)	0.0405 (17)	0.0413 (16)	−0.0003 (14)	0.0011 (13)	−0.0064 (13)
C3A	0.047 (2)	0.076 (3)	0.068 (3)	−0.0024 (19)	0.0120 (18)	−0.021 (2)
C17A	0.048 (2)	0.059 (2)	0.095 (3)	−0.0060 (18)	0.023 (2)	−0.023 (2)
C18B	0.061 (2)	0.062 (2)	0.052 (2)	0.0003 (19)	−0.0080 (17)	0.0014 (18)
C19A	0.049 (2)	0.059 (2)	0.092 (3)	−0.0071 (18)	0.004 (2)	−0.019 (2)
C15B	0.0434 (19)	0.083 (3)	0.056 (2)	−0.0013 (19)	0.0085 (16)	0.015 (2)
C2B	0.056 (2)	0.079 (3)	0.066 (3)	0.009 (2)	0.0218 (19)	0.027 (2)
C19B	0.076 (3)	0.049 (2)	0.075 (3)	−0.0146 (19)	−0.020 (2)	0.0074 (19)
C7A	0.069 (3)	0.048 (2)	0.053 (2)	0.0077 (18)	0.0001 (18)	0.0039 (16)
C2A	0.065 (3)	0.076 (3)	0.069 (3)	−0.002 (2)	0.025 (2)	0.000 (2)
C16B	0.060 (2)	0.084 (3)	0.066 (2)	−0.013 (2)	0.0094 (19)	0.024 (2)
C15A	0.089 (3)	0.058 (2)	0.069 (3)	−0.004 (2)	0.030 (2)	0.005 (2)
C20B	0.119 (4)	0.051 (2)	0.076 (3)	−0.010 (3)	0.004 (3)	0.012 (2)
C16A	0.086 (3)	0.068 (3)	0.117 (5)	−0.010 (3)	0.055 (3)	0.000 (3)
C20A	0.050 (3)	0.110 (5)	0.140 (5)	−0.020 (3)	0.009 (3)	−0.045 (4)

Geometric parameters (Å, º)

Cl1B—C4B	1.737 (4)	C14A—C15A	1.539 (5)
Cl1A—C4A	1.744 (4)	C5A—C6A	1.486 (6)
O1B—C3B	1.234 (5)	C5A—C10A	1.532 (5)
O2B—H2B	0.8200	C9A—H9A	0.9800
O2B—C17B	1.443 (5)	C9A—C10A	1.589 (5)
O2A—H2A	0.8200	C9A—C8A	1.547 (5)
O2A—C17A	1.428 (5)	C17B—C16B	1.552 (6)
O1A—C3A	1.226 (5)	C17B—C20B	1.518 (7)
C8B—H8B	0.9800	C1B—H1B	0.9300
C8B—C7B	1.526 (5)	C1B—C2B	1.317 (7)
C8B—C9B	1.538 (4)	C6B—H6BA	0.9700
C8B—C14B	1.520 (5)	C6B—H6BB	0.9700
C7B—H7BA	0.9700	C6A—H6AA	0.9700
C7B—H7BB	0.9700	C6A—H6AB	0.9700
C7B—C6B	1.521 (5)	C6A—C7A	1.532 (6)
C9B—H9B	0.9800	C10A—C1A	1.481 (6)
C9B—C10B	1.576 (5)	C10A—C19A	1.534 (5)
C9B—C11B	1.535 (5)	C1A—H1A	0.9300
C5B—C10B	1.525 (5)	C1A—C2A	1.335 (6)
C5B—C4B	1.336 (5)	C8A—H8A	0.9800
C5B—C6B	1.503 (5)	C8A—C7A	1.518 (5)
C10B—C1B	1.494 (6)	C3A—C2A	1.470 (7)
C10B—C19B	1.547 (6)	C17A—C16A	1.548 (8)
C12A—H12C	0.9700	C17A—C20A	1.532 (8)
C12A—H12D	0.9700	C18B—H18A	0.9600
C12A—C13A	1.522 (5)	C18B—H18B	0.9600
C12A—C11A	1.542 (5)	C18B—H18C	0.9600
C4B—C3B	1.476 (5)	C19A—H19D	0.9600
C3B—C2B	1.446 (6)	C19A—H19E	0.9600
C13A—C18A	1.534 (5)	C19A—H19F	0.9600
C13A—C14A	1.542 (5)	C15B—H15A	0.9700
C13A—C17A	1.566 (5)	C15B—H15B	0.9700
C4A—C5A	1.331 (5)	C15B—C16B	1.542 (7)
C4A—C3A	1.457 (7)	C2B—H2BA	0.9300
C13B—C14B	1.542 (5)	C19B—H19A	0.9600
C13B—C12B	1.520 (5)	C19B—H19B	0.9600
C13B—C17B	1.561 (5)	C19B—H19C	0.9600
C13B—C18B	1.543 (6)	C7A—H7AA	0.9700
C11B—H11A	0.9700	C7A—H7AB	0.9700
C11B—H11B	0.9700	C2A—H2AA	0.9300
C11B—C12B	1.526 (5)	C16B—H16A	0.9700
C14B—H14B	0.9800	C16B—H16B	0.9700
C14B—C15B	1.531 (5)	C15A—H15C	0.9700
C11A—H11C	0.9700	C15A—H15D	0.9700
C11A—H11D	0.9700	C15A—C16A	1.531 (8)
C11A—C9A	1.534 (5)	C20B—H20A	0.9600
C12B—H12A	0.9700	C20B—H20B	0.9600
C12B—H12B	0.9700	C20B—H20C	0.9600
C18A—H18D	0.9600	C16A—H16C	0.9700
C18A—H18E	0.9600	C16A—H16D	0.9700
C18A—H18F	0.9600	C20A—H20D	0.9600
C14A—H14A	0.9800	C20A—H20E	0.9600
C14A—C8A	1.515 (5)	C20A—H20F	0.9600
C17B—O2B—H2B	109.5	C20B—C17B—C16B	112.0 (4)
C17A—O2A—H2A	109.5	C10B—C1B—H1B	117.5
C7B—C8B—H8B	108.8	C2B—C1B—C10B	125.1 (4)
C7B—C8B—C9B	109.5 (3)	C2B—C1B—H1B	117.5
C9B—C8B—H8B	108.8	C7B—C6B—H6BA	110.0
C14B—C8B—H8B	108.8	C7B—C6B—H6BB	110.0
C14B—C8B—C7B	111.8 (3)	C5B—C6B—C7B	108.3 (3)
C14B—C8B—C9B	109.0 (3)	C5B—C6B—H6BA	110.0
C8B—C7B—H7BA	109.0	C5B—C6B—H6BB	110.0
C8B—C7B—H7BB	109.0	H6BA—C6B—H6BB	108.4
H7BA—C7B—H7BB	107.8	C5A—C6A—H6AA	109.6
C6B—C7B—C8B	112.7 (3)	C5A—C6A—H6AB	109.6
C6B—C7B—H7BA	109.0	C5A—C6A—C7A	110.1 (3)
C6B—C7B—H7BB	109.0	H6AA—C6A—H6AB	108.2
C8B—C9B—H9B	106.1	C7A—C6A—H6AA	109.6
C8B—C9B—C10B	111.6 (3)	C7A—C6A—H6AB	109.6
C10B—C9B—H9B	106.1	C5A—C10A—C9A	106.2 (3)
C11B—C9B—C8B	112.4 (3)	C5A—C10A—C19A	109.5 (3)
C11B—C9B—H9B	106.1	C1A—C10A—C5A	112.5 (3)
C11B—C9B—C10B	113.8 (3)	C1A—C10A—C9A	109.6 (3)
C4B—C5B—C10B	121.5 (3)	C1A—C10A—C19A	107.5 (4)
C4B—C5B—C6B	123.3 (3)	C19A—C10A—C9A	111.5 (3)
C6B—C5B—C10B	115.0 (3)	C10A—C1A—H1A	117.6
C5B—C10B—C9B	107.3 (3)	C2A—C1A—C10A	124.7 (4)
C5B—C10B—C19B	109.5 (3)	C2A—C1A—H1A	117.6
C1B—C10B—C9B	108.8 (3)	C14A—C8A—C9A	108.4 (3)
C1B—C10B—C5B	112.1 (3)	C14A—C8A—H8A	108.9
C1B—C10B—C19B	107.9 (3)	C14A—C8A—C7A	110.6 (3)
C19B—C10B—C9B	111.3 (3)	C9A—C8A—H8A	108.9
H12C—C12A—H12D	108.0	C7A—C8A—C9A	111.2 (3)
C13A—C12A—H12C	109.3	C7A—C8A—H8A	108.9
C13A—C12A—H12D	109.3	O1A—C3A—C4A	123.4 (5)
C13A—C12A—C11A	111.6 (3)	O1A—C3A—C2A	121.5 (5)
C11A—C12A—H12C	109.3	C4A—C3A—C2A	115.1 (3)
C11A—C12A—H12D	109.3	O2A—C17A—C13A	110.0 (3)
C5B—C4B—Cl1B	122.4 (3)	O2A—C17A—C16A	111.8 (4)
C5B—C4B—C3B	123.4 (3)	O2A—C17A—C20A	107.3 (4)
C3B—C4B—Cl1B	114.2 (3)	C16A—C17A—C13A	103.2 (4)
O1B—C3B—C4B	121.7 (4)	C20A—C17A—C13A	113.1 (4)
O1B—C3B—C2B	122.7 (4)	C20A—C17A—C16A	111.6 (5)
C2B—C3B—C4B	115.6 (3)	C13B—C18B—H18A	109.5
C12A—C13A—C18A	109.9 (3)	C13B—C18B—H18B	109.5
C12A—C13A—C14A	108.1 (3)	C13B—C18B—H18C	109.5
C12A—C13A—C17A	118.0 (4)	H18A—C18B—H18B	109.5
C18A—C13A—C14A	112.0 (3)	H18A—C18B—H18C	109.5
C18A—C13A—C17A	107.9 (3)	H18B—C18B—H18C	109.5
C14A—C13A—C17A	100.7 (3)	C10A—C19A—H19D	109.5
C5A—C4A—Cl1A	121.7 (4)	C10A—C19A—H19E	109.5
C5A—C4A—C3A	124.6 (4)	C10A—C19A—H19F	109.5
C3A—C4A—Cl1A	113.7 (3)	H19D—C19A—H19E	109.5
C14B—C13B—C17B	100.3 (3)	H19D—C19A—H19F	109.5
C14B—C13B—C18B	111.9 (3)	H19E—C19A—H19F	109.5
C12B—C13B—C14B	108.1 (3)	C14B—C15B—H15A	111.1
C12B—C13B—C17B	117.3 (3)	C14B—C15B—H15B	111.1
C12B—C13B—C18B	110.0 (3)	C14B—C15B—C16B	103.2 (3)
C18B—C13B—C17B	108.8 (3)	H15A—C15B—H15B	109.1
C9B—C11B—H11A	109.2	C16B—C15B—H15A	111.1
C9B—C11B—H11B	109.2	C16B—C15B—H15B	111.1
H11A—C11B—H11B	107.9	C3B—C2B—H2BA	118.9
C12B—C11B—C9B	112.3 (3)	C1B—C2B—C3B	122.2 (4)
C12B—C11B—H11A	109.2	C1B—C2B—H2BA	118.9
C12B—C11B—H11B	109.2	C10B—C19B—H19A	109.5
C8B—C14B—C13B	114.0 (3)	C10B—C19B—H19B	109.5
C8B—C14B—H14B	106.7	C10B—C19B—H19C	109.5
C8B—C14B—C15B	118.3 (3)	H19A—C19B—H19B	109.5
C13B—C14B—H14B	106.7	H19A—C19B—H19C	109.5
C15B—C14B—C13B	103.6 (3)	H19B—C19B—H19C	109.5
C15B—C14B—H14B	106.7	C6A—C7A—H7AA	109.2
C12A—C11A—H11C	109.3	C6A—C7A—H7AB	109.2
C12A—C11A—H11D	109.3	C8A—C7A—C6A	112.2 (3)
H11C—C11A—H11D	107.9	C8A—C7A—H7AA	109.2
C9A—C11A—C12A	111.7 (3)	C8A—C7A—H7AB	109.2
C9A—C11A—H11C	109.3	H7AA—C7A—H7AB	107.9
C9A—C11A—H11D	109.3	C1A—C2A—C3A	121.7 (4)
C13B—C12B—C11B	111.4 (3)	C1A—C2A—H2AA	119.1
C13B—C12B—H12A	109.4	C3A—C2A—H2AA	119.1
C13B—C12B—H12B	109.4	C17B—C16B—H16A	110.1
C11B—C12B—H12A	109.4	C17B—C16B—H16B	110.1
C11B—C12B—H12B	109.3	C15B—C16B—C17B	107.9 (3)
H12A—C12B—H12B	108.0	C15B—C16B—H16A	110.1
C13A—C18A—H18D	109.5	C15B—C16B—H16B	110.1
C13A—C18A—H18E	109.5	H16A—C16B—H16B	108.4
C13A—C18A—H18F	109.5	C14A—C15A—H15C	111.2
H18D—C18A—H18E	109.5	C14A—C15A—H15D	111.2
H18D—C18A—H18F	109.5	H15C—C15A—H15D	109.1
H18E—C18A—H18F	109.5	C16A—C15A—C14A	103.0 (4)
C13A—C14A—H14A	106.5	C16A—C15A—H15C	111.2
C8A—C14A—C13A	114.1 (3)	C16A—C15A—H15D	111.2
C8A—C14A—H14A	106.5	C17B—C20B—H20A	109.5
C8A—C14A—C15A	118.7 (4)	C17B—C20B—H20B	109.5
C15A—C14A—C13A	103.8 (3)	C17B—C20B—H20C	109.5
C15A—C14A—H14A	106.5	H20A—C20B—H20B	109.5
C4A—C5A—C6A	123.4 (4)	H20A—C20B—H20C	109.5
C4A—C5A—C10A	121.2 (4)	H20B—C20B—H20C	109.5
C6A—C5A—C10A	115.4 (3)	C17A—C16A—H16C	110.0
C11A—C9A—H9A	106.3	C17A—C16A—H16D	110.0
C11A—C9A—C10A	113.7 (3)	C15A—C16A—C17A	108.5 (4)
C11A—C9A—C8A	111.3 (3)	C15A—C16A—H16C	110.0
C10A—C9A—H9A	106.3	C15A—C16A—H16D	110.0
C8A—C9A—H9A	106.3	H16C—C16A—H16D	108.4
C8A—C9A—C10A	112.3 (3)	C17A—C20A—H20D	109.5
O2B—C17B—C13B	108.7 (3)	C17A—C20A—H20E	109.5
O2B—C17B—C16B	111.1 (3)	C17A—C20A—H20F	109.5
O2B—C17B—C20B	108.2 (4)	H20D—C20A—H20E	109.5
C16B—C17B—C13B	102.7 (3)	H20D—C20A—H20F	109.5
C20B—C17B—C13B	114.1 (3)	H20E—C20A—H20F	109.5

4-Chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one acetic acid hemisolvate hemihydrate (TBOL3)

Crystal data

2C20H27ClO2·C2H4O2·H2O	Dx = 1.262 Mg m^−3
Mr = 747.80	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P43212	Cell parameters from 32928 reflections
a = 10.70311 (10) Å	θ = 4.2–71.3°
c = 68.7275 (8) Å	µ = 1.87 mm^−1
V = 7873.20 (18) Å^3	T = 293 K
Z = 8	Needle, colourless
F(000) = 3216	0.1 × 0.02 × 0.01 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	Rint = 0.048
Radiation source: micro-focus sealed X-ray tube	θmax = 71.3°, θmin = 4.2°
ω scans	h = −12→12
116676 measured reflections	k = −13→13
7557 independent reflections	l = −84→83
7057 reflections with I > 2σ(I)

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 2.5992P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max < 0.001
wR(F^2) = 0.098	Δρmax = 0.26 e Å^−3
S = 1.06	Δρmin = −0.25 e Å^−3
7557 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
501 parameters	Extinction coefficient: 0.00061 (5)
5 restraints	Absolute structure: Flack x determined using 2580 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (4)
Hydrogen site location: mixed

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Suitable single crystals were attached on a nylon loop coated in oil and mounted on the goniometer of a SuperNova diffractometer equipped with dual (Mo and Cu) microsources and Eos CCD detector. The X-ray tube was set to operate at 50 kV and 0.8 mA. Experimental data were collected and corrected for Lorentz, polarization and absorption effects by CrysAlis PRO software (Rigaku, 2018). The crystal structure of TBOL-2 was solved with SHELXT (Sheldrick, 2015) using Intrinsic Phasing, while direct methods (SHELXS; Sheldrick, 2008) was employed for the other structures. They were refined using SHELXL (Sheldrick, 2015) refinement package using least-squares minimization. Both methods are implemented in OLEX2 software (Dolomanov et al., 2009).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1B	0.99172 (8)	0.76821 (8)	0.09065 (2)	0.0650 (2)
O1B	0.9729 (3)	1.0032 (3)	0.11095 (3)	0.0731 (7)
C9B	0.7385 (3)	1.0238 (2)	0.04413 (4)	0.0399 (6)
H9B	0.686181	1.002115	0.055334	0.048*
C14B	0.5940 (3)	0.8984 (3)	0.02345 (4)	0.0418 (6)
H14B	0.544710	0.883523	0.035239	0.050*
C13B	0.5393 (3)	1.0154 (3)	0.01394 (4)	0.0457 (7)
C8B	0.7296 (3)	0.9117 (3)	0.03008 (4)	0.0409 (6)
H8B	0.781639	0.929053	0.018665	0.049*
C4B	0.9472 (3)	0.9087 (3)	0.08007 (4)	0.0453 (6)
O2B	0.3495 (3)	1.0376 (3)	−0.00725 (3)	0.0742 (7)
H2B	0.340022	1.110208	−0.003720	0.111*
C5B	0.9151 (3)	0.9176 (3)	0.06121 (4)	0.0441 (6)
C3B	0.9435 (3)	1.0144 (3)	0.09376 (4)	0.0521 (7)
C10B	0.8747 (3)	1.0412 (3)	0.05244 (4)	0.0447 (7)
C12B	0.5470 (3)	1.1233 (3)	0.02852 (5)	0.0556 (8)
H12A	0.493885	1.105149	0.039604	0.067*
H12B	0.516555	1.199224	0.022444	0.067*
C6B	0.9099 (3)	0.8077 (3)	0.04765 (5)	0.0555 (8)
H6BA	0.934055	0.732300	0.054525	0.067*
H6BB	0.967770	0.820108	0.036957	0.067*
C15B	0.5597 (3)	0.7938 (3)	0.00922 (5)	0.0556 (8)
H15A	0.552425	0.714390	0.015935	0.067*
H15B	0.622198	0.786107	−0.000932	0.067*
C7B	0.7774 (3)	0.7937 (3)	0.03979 (4)	0.0492 (7)
H7BA	0.775579	0.725822	0.030446	0.059*
H7BB	0.721917	0.771860	0.050420	0.059*
C18B	0.6103 (4)	1.0520 (4)	−0.00482 (4)	0.0646 (9)
H18A	0.698175	1.056924	−0.002111	0.097*
H18B	0.581063	1.131688	−0.009328	0.097*
H18C	0.595803	0.990054	−0.014668	0.097*
C11B	0.6814 (3)	1.1435 (3)	0.03551 (5)	0.0556 (8)
H11A	0.682332	1.208748	0.045302	0.067*
H11B	0.732237	1.171249	0.024656	0.067*
C1B	0.8729 (3)	1.1442 (3)	0.06714 (5)	0.0543 (7)
H1B	0.850378	1.223346	0.062806	0.065*
C17B	0.4070 (3)	0.9666 (3)	0.00824 (4)	0.0552 (8)
C19B	0.9684 (3)	1.0798 (4)	0.03626 (5)	0.0702 (10)
H19A	0.965388	1.019851	0.025875	0.105*
H19B	1.051337	1.082456	0.041562	0.105*
H19C	0.946382	1.160770	0.031344	0.105*
C20B	0.3137 (3)	0.9646 (4)	0.02490 (5)	0.0749 (11)
H20A	0.347602	0.917394	0.035541	0.112*
H20B	0.237320	0.926614	0.020599	0.112*
H20C	0.297314	1.048586	0.029096	0.112*
C2B	0.9007 (3)	1.1320 (3)	0.08570 (5)	0.0597 (8)
H2BA	0.892579	1.200829	0.093869	0.072*
C16B	0.4333 (4)	0.8337 (3)	0.00066 (5)	0.0672 (9)
H16A	0.367926	0.776887	0.004805	0.081*
H16B	0.436752	0.833417	−0.013444	0.081*
Cl1A	0.75010 (8)	0.49281 (8)	0.06458 (2)	0.0667 (2)
C8A	0.5253 (2)	0.8534 (2)	0.10165 (3)	0.0349 (5)
H8A	0.479301	0.826443	0.113240	0.042*
O2A	0.3790 (2)	1.2842 (2)	0.11353 (4)	0.0634 (6)
H2A	0.411990	1.344942	0.118674	0.095*
C9A	0.4460 (2)	0.8230 (2)	0.08349 (3)	0.0344 (5)
H9A	0.494389	0.851695	0.072238	0.041*
C14A	0.5436 (2)	0.9944 (2)	0.10266 (3)	0.0366 (5)
H14A	0.585808	1.018694	0.090585	0.044*
C4A	0.6002 (3)	0.5557 (3)	0.06533 (4)	0.0469 (7)
C11A	0.3237 (3)	0.8975 (3)	0.08331 (4)	0.0457 (6)
H11C	0.271337	0.869520	0.093973	0.055*
H11D	0.279593	0.880855	0.071264	0.055*
C18A	0.3441 (3)	1.0380 (3)	0.12162 (5)	0.0558 (8)
H18D	0.265487	1.081114	0.121039	0.084*
H18E	0.388886	1.063868	0.133030	0.084*
H18F	0.329486	0.949568	0.122173	0.084*
C13A	0.4213 (2)	1.0691 (2)	0.10342 (4)	0.0369 (6)
C10A	0.4280 (3)	0.6777 (2)	0.08080 (4)	0.0389 (6)
C12A	0.3455 (3)	1.0391 (3)	0.08522 (4)	0.0477 (7)
H12C	0.389633	1.069237	0.073822	0.057*
H12D	0.265605	1.081623	0.085861	0.057*
C5A	0.5569 (3)	0.6196 (2)	0.08077 (4)	0.0405 (6)
O1A	0.5704 (3)	0.4755 (3)	0.03384 (4)	0.0849 (8)
C19A	0.3497 (3)	0.6218 (3)	0.09762 (4)	0.0512 (7)
H19D	0.347752	0.532472	0.096435	0.077*
H19E	0.266102	0.654014	0.097012	0.077*
H19F	0.386784	0.644322	0.109849	0.077*
C6A	0.6342 (3)	0.6442 (3)	0.09850 (4)	0.0472 (7)
H6AA	0.715511	0.605169	0.097099	0.057*
H6AB	0.593654	0.608898	0.109856	0.057*
C15A	0.6213 (3)	1.0483 (3)	0.11928 (5)	0.0533 (7)
H15C	0.709873	1.037337	0.116875	0.064*
H15D	0.599934	1.008977	0.131557	0.064*
C17A	0.4740 (3)	1.2041 (3)	0.10549 (4)	0.0462 (7)
C7A	0.6499 (3)	0.7850 (3)	0.10113 (4)	0.0450 (6)
H7AA	0.694534	0.800911	0.113156	0.054*
H7AB	0.699836	0.817738	0.090507	0.054*
C3A	0.5270 (3)	0.5342 (3)	0.04768 (4)	0.0566 (8)
C1A	0.3578 (3)	0.6529 (3)	0.06237 (4)	0.0507 (7)
H1A	0.277748	0.685810	0.061224	0.061*
C2A	0.4024 (3)	0.5871 (3)	0.04752 (4)	0.0576 (8)
H2AA	0.351992	0.574457	0.036672	0.069*
C20A	0.5149 (4)	1.2624 (3)	0.08624 (5)	0.0717 (10)
H20D	0.572458	1.207451	0.079798	0.108*
H20E	0.554926	1.341104	0.088720	0.108*
H20F	0.443140	1.275373	0.078116	0.108*
C16A	0.5858 (3)	1.1879 (3)	0.11938 (5)	0.0632 (9)
H16C	0.563155	1.214156	0.132422	0.076*
H16D	0.655780	1.238195	0.115019	0.076*
O4	0.0479 (4)	0.4108 (4)	0.04510 (4)	0.1153 (13)
H4	0.062292	0.402023	0.033462	0.173*
C2	0.1314 (5)	0.3846 (5)	0.07617 (5)	0.1071 (18)
H2C	0.106109	0.469014	0.078750	0.161*
H2D	0.212237	0.369949	0.081770	0.161*
H2E	0.071919	0.327948	0.081804	0.161*
O3	0.2218 (4)	0.3014 (4)	0.04773 (5)	0.1191 (12)
C1	0.1372 (5)	0.3642 (5)	0.05497 (6)	0.0806 (12)
O2W	0.2672 (5)	0.2692 (6)	0.00919 (8)	0.0758 (14)	0.5
O1WA	0.443 (3)	0.424 (5)	−0.0006 (8)	0.072 (7)	0.25
H1WA	0.380444	0.361029	0.001301	0.05 (3)*	0.25
H1WB	0.479631	0.435400	0.011976	0.02 (3)*	0.25
O1WB	0.480 (3)	0.405 (5)	−0.0011 (8)	0.072 (7)	0.25
H1WC	0.483552	0.476007	−0.009701	0.00 (2)*	0.25
H1WD	0.538674	0.425200	0.009023	0.12 (9)*	0.25
H2WA	0.264 (9)	0.295 (8)	0.0229 (4)	0.11 (3)*	0.5
H2WB	0.30 (2)	0.344 (10)	0.0029 (14)	0.24 (8)*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1B	0.0570 (5)	0.0636 (5)	0.0746 (5)	0.0067 (4)	−0.0158 (4)	0.0126 (4)
O1B	0.0867 (18)	0.0864 (18)	0.0462 (11)	−0.0038 (15)	−0.0138 (11)	−0.0030 (12)
C9B	0.0458 (15)	0.0373 (14)	0.0368 (12)	−0.0002 (11)	0.0017 (11)	0.0005 (10)
C14B	0.0452 (16)	0.0458 (16)	0.0343 (12)	0.0023 (12)	0.0003 (11)	−0.0022 (11)
C13B	0.0515 (17)	0.0492 (16)	0.0363 (13)	0.0085 (13)	−0.0002 (11)	0.0020 (12)
C8B	0.0464 (15)	0.0423 (15)	0.0339 (12)	0.0059 (12)	0.0026 (11)	−0.0017 (10)
C4B	0.0351 (15)	0.0481 (16)	0.0526 (15)	−0.0027 (12)	−0.0025 (12)	0.0026 (13)
O2B	0.0786 (17)	0.0824 (19)	0.0615 (13)	0.0254 (15)	−0.0245 (12)	0.0009 (12)
C5B	0.0350 (14)	0.0464 (16)	0.0508 (14)	−0.0001 (12)	0.0002 (12)	−0.0018 (12)
C3B	0.0462 (17)	0.0578 (19)	0.0523 (16)	−0.0099 (14)	−0.0021 (13)	−0.0028 (14)
C10B	0.0492 (16)	0.0407 (15)	0.0443 (14)	−0.0035 (12)	0.0006 (12)	0.0007 (11)
C12B	0.063 (2)	0.0489 (18)	0.0545 (16)	0.0175 (15)	−0.0063 (15)	−0.0014 (14)
C6B	0.0556 (19)	0.0510 (18)	0.0600 (18)	0.0142 (15)	−0.0072 (15)	−0.0069 (14)
C15B	0.061 (2)	0.0524 (19)	0.0540 (16)	0.0067 (15)	−0.0105 (15)	−0.0104 (14)
C7B	0.0581 (19)	0.0411 (16)	0.0485 (15)	0.0074 (14)	−0.0081 (13)	−0.0061 (12)
C18B	0.073 (2)	0.077 (2)	0.0431 (16)	0.0080 (19)	0.0044 (15)	0.0145 (15)
C11B	0.073 (2)	0.0387 (16)	0.0553 (16)	0.0041 (15)	−0.0062 (15)	0.0012 (13)
C1B	0.059 (2)	0.0405 (16)	0.0631 (18)	−0.0075 (14)	−0.0070 (15)	−0.0024 (14)
C17B	0.0521 (18)	0.065 (2)	0.0480 (15)	0.0116 (15)	−0.0088 (13)	0.0000 (14)
C19B	0.058 (2)	0.082 (3)	0.071 (2)	−0.0203 (19)	0.0104 (17)	0.0119 (19)
C20B	0.049 (2)	0.101 (3)	0.075 (2)	0.004 (2)	0.0025 (17)	−0.001 (2)
C2B	0.063 (2)	0.0537 (19)	0.0622 (19)	−0.0066 (16)	−0.0066 (16)	−0.0137 (15)
C16B	0.065 (2)	0.068 (2)	0.068 (2)	0.0044 (17)	−0.0179 (18)	−0.0131 (17)
Cl1A	0.0640 (5)	0.0488 (4)	0.0872 (5)	0.0142 (4)	0.0114 (4)	−0.0055 (4)
C8A	0.0360 (14)	0.0349 (13)	0.0337 (11)	0.0006 (11)	0.0012 (10)	0.0004 (10)
O2A	0.0597 (14)	0.0448 (13)	0.0857 (16)	0.0076 (10)	0.0107 (12)	−0.0189 (11)
C9A	0.0363 (14)	0.0316 (13)	0.0354 (12)	−0.0045 (10)	−0.0007 (10)	0.0033 (10)
C14A	0.0340 (13)	0.0387 (14)	0.0370 (12)	−0.0051 (11)	0.0027 (10)	−0.0026 (11)
C4A	0.0558 (18)	0.0296 (14)	0.0552 (16)	0.0016 (12)	0.0047 (13)	0.0013 (12)
C11A	0.0368 (15)	0.0422 (16)	0.0581 (16)	0.0015 (12)	−0.0113 (12)	−0.0011 (13)
C18A	0.0574 (19)	0.0490 (18)	0.0612 (18)	0.0013 (14)	0.0259 (15)	0.0011 (14)
C13A	0.0370 (14)	0.0322 (13)	0.0414 (13)	−0.0001 (11)	0.0056 (11)	0.0009 (10)
C10A	0.0400 (15)	0.0351 (14)	0.0415 (13)	−0.0028 (11)	−0.0029 (11)	0.0004 (10)
C12A	0.0491 (17)	0.0375 (15)	0.0565 (16)	0.0072 (12)	−0.0094 (13)	0.0018 (12)
C5A	0.0468 (16)	0.0292 (13)	0.0454 (14)	−0.0007 (11)	−0.0010 (12)	0.0034 (11)
O1A	0.114 (2)	0.0799 (19)	0.0611 (13)	0.0165 (17)	0.0017 (14)	−0.0256 (13)
C19A	0.0521 (18)	0.0410 (16)	0.0605 (17)	−0.0101 (13)	0.0051 (14)	0.0078 (13)
C6A	0.0487 (17)	0.0402 (15)	0.0526 (15)	0.0122 (13)	−0.0068 (13)	0.0013 (12)
C15A	0.0460 (17)	0.0518 (18)	0.0622 (17)	0.0001 (14)	−0.0094 (14)	−0.0164 (14)
C17A	0.0481 (17)	0.0354 (14)	0.0552 (16)	−0.0005 (12)	0.0099 (13)	−0.0041 (12)
C7A	0.0421 (15)	0.0446 (16)	0.0482 (14)	0.0052 (13)	−0.0085 (12)	−0.0060 (12)
C3A	0.079 (2)	0.0395 (16)	0.0513 (16)	−0.0032 (15)	0.0048 (16)	−0.0039 (13)
C1A	0.0527 (18)	0.0435 (16)	0.0559 (17)	−0.0061 (14)	−0.0131 (14)	−0.0030 (13)
C2A	0.072 (2)	0.0480 (18)	0.0525 (16)	−0.0073 (16)	−0.0139 (16)	−0.0077 (14)
C20A	0.091 (3)	0.0381 (17)	0.086 (2)	−0.0090 (17)	0.024 (2)	0.0101 (16)
C16A	0.057 (2)	0.0478 (18)	0.085 (2)	−0.0029 (15)	−0.0060 (18)	−0.0204 (16)
O4	0.150 (3)	0.131 (3)	0.0647 (16)	0.037 (3)	−0.007 (2)	0.0128 (19)
C2	0.135 (4)	0.123 (4)	0.063 (2)	−0.066 (3)	−0.012 (3)	0.003 (2)
O3	0.118 (3)	0.136 (3)	0.103 (3)	0.006 (3)	−0.006 (2)	−0.006 (2)
C1	0.094 (3)	0.081 (3)	0.067 (2)	−0.032 (3)	−0.006 (2)	0.007 (2)
O2W	0.073 (3)	0.077 (4)	0.077 (3)	0.019 (3)	0.000 (3)	0.003 (3)
O1WA	0.059 (19)	0.092 (16)	0.066 (4)	0.001 (14)	−0.003 (15)	0.006 (9)
O1WB	0.059 (19)	0.092 (16)	0.066 (4)	0.001 (14)	−0.003 (15)	0.006 (9)

Geometric parameters (Å, º)

Cl1B—C4B	1.737 (3)	C9A—H9A	0.9800
O1B—C3B	1.229 (3)	C9A—C11A	1.533 (4)
C9B—H9B	0.9800	C9A—C10A	1.578 (3)
C9B—C8B	1.543 (4)	C14A—H14A	0.9800
C9B—C10B	1.576 (4)	C14A—C13A	1.535 (4)
C9B—C11B	1.538 (4)	C14A—C15A	1.526 (4)
C14B—H14B	0.9800	C4A—C5A	1.344 (4)
C14B—C13B	1.530 (4)	C4A—C3A	1.462 (4)
C14B—C8B	1.528 (4)	C11A—H11C	0.9700
C14B—C15B	1.532 (4)	C11A—H11D	0.9700
C13B—C12B	1.531 (4)	C11A—C12A	1.539 (4)
C13B—C18B	1.547 (4)	C18A—H18D	0.9600
C13B—C17B	1.560 (4)	C18A—H18E	0.9600
C8B—H8B	0.9800	C18A—H18F	0.9600
C8B—C7B	1.517 (4)	C18A—C13A	1.537 (4)
C4B—C5B	1.344 (4)	C13A—C12A	1.525 (4)
C4B—C3B	1.472 (4)	C13A—C17A	1.557 (4)
O2B—H2B	0.8200	C10A—C5A	1.514 (4)
O2B—C17B	1.445 (4)	C10A—C19A	1.548 (4)
C5B—C10B	1.517 (4)	C10A—C1A	1.496 (4)
C5B—C6B	1.502 (4)	C12A—H12C	0.9700
C3B—C2B	1.449 (5)	C12A—H12D	0.9700
C10B—C1B	1.495 (4)	C5A—C6A	1.496 (4)
C10B—C19B	1.553 (4)	O1A—C3A	1.232 (4)
C12B—H12A	0.9700	C19A—H19D	0.9600
C12B—H12B	0.9700	C19A—H19E	0.9600
C12B—C11B	1.532 (5)	C19A—H19F	0.9600
C6B—H6BA	0.9700	C6A—H6AA	0.9700
C6B—H6BB	0.9700	C6A—H6AB	0.9700
C6B—C7B	1.525 (4)	C6A—C7A	1.527 (4)
C15B—H15A	0.9700	C15A—H15C	0.9700
C15B—H15B	0.9700	C15A—H15D	0.9700
C15B—C16B	1.536 (5)	C15A—C16A	1.542 (4)
C7B—H7BA	0.9700	C17A—C20A	1.527 (4)
C7B—H7BB	0.9700	C17A—C16A	1.541 (5)
C18B—H18A	0.9600	C7A—H7AA	0.9700
C18B—H18B	0.9600	C7A—H7AB	0.9700
C18B—H18C	0.9600	C3A—C2A	1.448 (5)
C11B—H11A	0.9700	C1A—H1A	0.9300
C11B—H11B	0.9700	C1A—C2A	1.329 (4)
C1B—H1B	0.9300	C2A—H2AA	0.9300
C1B—C2B	1.316 (4)	C20A—H20D	0.9600
C17B—C20B	1.520 (5)	C20A—H20E	0.9600
C17B—C16B	1.540 (5)	C20A—H20F	0.9600
C19B—H19A	0.9600	C16A—H16C	0.9700
C19B—H19B	0.9600	C16A—H16D	0.9700
C19B—H19C	0.9600	O4—H4	0.8200
C20B—H20A	0.9600	O4—C1	1.274 (6)
C20B—H20B	0.9600	C2—H2C	0.9600
C20B—H20C	0.9600	C2—H2D	0.9600
C2B—H2BA	0.9300	C2—H2E	0.9600
C16B—H16A	0.9700	C2—C1	1.475 (5)
C16B—H16B	0.9700	O3—C1	1.232 (6)
Cl1A—C4A	1.741 (3)	O2W—H2WA	0.982 (14)
C8A—H8A	0.9800	O2W—H2WB	0.98 (3)
C8A—C9A	1.544 (3)	O1WA—H1WA	0.9581
C8A—C14A	1.524 (4)	O1WA—H1WB	0.9592
C8A—C7A	1.521 (4)	O1WB—H1WC	0.9590
O2A—H2A	0.8200	O1WB—H1WD	0.9588
O2A—C17A	1.440 (3)
C8B—C9B—H9B	105.8	C8A—C9A—H9A	106.3
C8B—C9B—C10B	112.1 (2)	C8A—C9A—C10A	111.70 (19)
C10B—C9B—H9B	105.8	C11A—C9A—C8A	111.5 (2)
C11B—C9B—H9B	105.8	C11A—C9A—H9A	106.3
C11B—C9B—C8B	112.4 (2)	C11A—C9A—C10A	114.0 (2)
C11B—C9B—C10B	114.1 (2)	C10A—C9A—H9A	106.3
C13B—C14B—H14B	106.3	C8A—C14A—H14A	106.4
C13B—C14B—C15B	103.5 (2)	C8A—C14A—C13A	114.1 (2)
C8B—C14B—H14B	106.3	C8A—C14A—C15A	118.6 (2)
C8B—C14B—C13B	114.5 (2)	C13A—C14A—H14A	106.4
C8B—C14B—C15B	119.1 (2)	C15A—C14A—H14A	106.4
C15B—C14B—H14B	106.3	C15A—C14A—C13A	104.0 (2)
C14B—C13B—C12B	108.5 (2)	C5A—C4A—Cl1A	122.5 (2)
C14B—C13B—C18B	112.0 (2)	C5A—C4A—C3A	123.4 (3)
C14B—C13B—C17B	100.4 (2)	C3A—C4A—Cl1A	114.1 (2)
C12B—C13B—C18B	109.2 (3)	C9A—C11A—H11C	109.1
C12B—C13B—C17B	117.8 (3)	C9A—C11A—H11D	109.1
C18B—C13B—C17B	108.8 (2)	C9A—C11A—C12A	112.5 (2)
C9B—C8B—H8B	108.6	H11C—C11A—H11D	107.8
C14B—C8B—C9B	108.5 (2)	C12A—C11A—H11C	109.1
C14B—C8B—H8B	108.6	C12A—C11A—H11D	109.1
C7B—C8B—C9B	110.6 (2)	H18D—C18A—H18E	109.5
C7B—C8B—C14B	111.9 (2)	H18D—C18A—H18F	109.5
C7B—C8B—H8B	108.6	H18E—C18A—H18F	109.5
C5B—C4B—Cl1B	122.4 (2)	C13A—C18A—H18D	109.5
C5B—C4B—C3B	123.7 (3)	C13A—C18A—H18E	109.5
C3B—C4B—Cl1B	113.9 (2)	C13A—C18A—H18F	109.5
C17B—O2B—H2B	109.5	C14A—C13A—C18A	111.9 (2)
C4B—C5B—C10B	121.2 (3)	C14A—C13A—C17A	100.3 (2)
C4B—C5B—C6B	123.5 (3)	C18A—C13A—C17A	108.8 (2)
C6B—C5B—C10B	115.2 (2)	C12A—C13A—C14A	108.4 (2)
O1B—C3B—C4B	122.2 (3)	C12A—C13A—C18A	109.6 (2)
O1B—C3B—C2B	122.2 (3)	C12A—C13A—C17A	117.6 (2)
C2B—C3B—C4B	115.6 (3)	C5A—C10A—C9A	107.1 (2)
C5B—C10B—C9B	107.7 (2)	C5A—C10A—C19A	109.6 (2)
C5B—C10B—C19B	109.4 (3)	C19A—C10A—C9A	111.1 (2)
C1B—C10B—C9B	108.7 (2)	C1A—C10A—C9A	109.6 (2)
C1B—C10B—C5B	112.2 (2)	C1A—C10A—C5A	112.5 (2)
C1B—C10B—C19B	107.2 (3)	C1A—C10A—C19A	107.0 (2)
C19B—C10B—C9B	111.7 (2)	C11A—C12A—H12C	109.4
C13B—C12B—H12A	109.4	C11A—C12A—H12D	109.4
C13B—C12B—H12B	109.4	C13A—C12A—C11A	111.0 (2)
C13B—C12B—C11B	111.2 (3)	C13A—C12A—H12C	109.4
H12A—C12B—H12B	108.0	C13A—C12A—H12D	109.4
C11B—C12B—H12A	109.4	H12C—C12A—H12D	108.0
C11B—C12B—H12B	109.4	C4A—C5A—C10A	121.6 (3)
C5B—C6B—H6BA	109.8	C4A—C5A—C6A	122.8 (3)
C5B—C6B—H6BB	109.8	C6A—C5A—C10A	115.5 (2)
C5B—C6B—C7B	109.3 (2)	C10A—C19A—H19D	109.5
H6BA—C6B—H6BB	108.3	C10A—C19A—H19E	109.5
C7B—C6B—H6BA	109.8	C10A—C19A—H19F	109.5
C7B—C6B—H6BB	109.8	H19D—C19A—H19E	109.5
C14B—C15B—H15A	110.8	H19D—C19A—H19F	109.5
C14B—C15B—H15B	110.8	H19E—C19A—H19F	109.5
C14B—C15B—C16B	104.6 (3)	C5A—C6A—H6AA	109.8
H15A—C15B—H15B	108.9	C5A—C6A—H6AB	109.8
C16B—C15B—H15A	110.8	C5A—C6A—C7A	109.3 (2)
C16B—C15B—H15B	110.8	H6AA—C6A—H6AB	108.3
C8B—C7B—C6B	112.8 (3)	C7A—C6A—H6AA	109.8
C8B—C7B—H7BA	109.0	C7A—C6A—H6AB	109.8
C8B—C7B—H7BB	109.0	C14A—C15A—H15C	111.0
C6B—C7B—H7BA	109.0	C14A—C15A—H15D	111.0
C6B—C7B—H7BB	109.0	C14A—C15A—C16A	103.6 (3)
H7BA—C7B—H7BB	107.8	H15C—C15A—H15D	109.0
C13B—C18B—H18A	109.5	C16A—C15A—H15C	111.0
C13B—C18B—H18B	109.5	C16A—C15A—H15D	111.0
C13B—C18B—H18C	109.5	O2A—C17A—C13A	109.4 (2)
H18A—C18B—H18B	109.5	O2A—C17A—C20A	106.9 (3)
H18A—C18B—H18C	109.5	O2A—C17A—C16A	112.2 (2)
H18B—C18B—H18C	109.5	C20A—C17A—C13A	113.8 (2)
C9B—C11B—H11A	109.2	C20A—C17A—C16A	111.1 (3)
C9B—C11B—H11B	109.2	C16A—C17A—C13A	103.5 (2)
C12B—C11B—C9B	112.1 (3)	C8A—C7A—C6A	112.4 (2)
C12B—C11B—H11A	109.2	C8A—C7A—H7AA	109.1
C12B—C11B—H11B	109.2	C8A—C7A—H7AB	109.1
H11A—C11B—H11B	107.9	C6A—C7A—H7AA	109.1
C10B—C1B—H1B	117.3	C6A—C7A—H7AB	109.1
C2B—C1B—C10B	125.4 (3)	H7AA—C7A—H7AB	107.9
C2B—C1B—H1B	117.3	O1A—C3A—C4A	121.3 (3)
O2B—C17B—C13B	113.3 (3)	O1A—C3A—C2A	122.7 (3)
O2B—C17B—C20B	106.4 (3)	C2A—C3A—C4A	116.0 (3)
O2B—C17B—C16B	108.3 (3)	C10A—C1A—H1A	117.8
C20B—C17B—C13B	114.3 (3)	C2A—C1A—C10A	124.3 (3)
C20B—C17B—C16B	111.2 (3)	C2A—C1A—H1A	117.8
C16B—C17B—C13B	103.2 (3)	C3A—C2A—H2AA	118.9
C10B—C19B—H19A	109.5	C1A—C2A—C3A	122.1 (3)
C10B—C19B—H19B	109.5	C1A—C2A—H2AA	118.9
C10B—C19B—H19C	109.5	C17A—C20A—H20D	109.5
H19A—C19B—H19B	109.5	C17A—C20A—H20E	109.5
H19A—C19B—H19C	109.5	C17A—C20A—H20F	109.5
H19B—C19B—H19C	109.5	H20D—C20A—H20E	109.5
C17B—C20B—H20A	109.5	H20D—C20A—H20F	109.5
C17B—C20B—H20B	109.5	H20E—C20A—H20F	109.5
C17B—C20B—H20C	109.5	C15A—C16A—H16C	110.3
H20A—C20B—H20B	109.5	C15A—C16A—H16D	110.3
H20A—C20B—H20C	109.5	C17A—C16A—C15A	107.3 (2)
H20B—C20B—H20C	109.5	C17A—C16A—H16C	110.3
C3B—C2B—H2BA	119.1	C17A—C16A—H16D	110.3
C1B—C2B—C3B	121.8 (3)	H16C—C16A—H16D	108.5
C1B—C2B—H2BA	119.1	C1—O4—H4	109.5
C15B—C16B—C17B	106.8 (3)	H2C—C2—H2D	109.5
C15B—C16B—H16A	110.4	H2C—C2—H2E	109.5
C15B—C16B—H16B	110.4	H2D—C2—H2E	109.5
C17B—C16B—H16A	110.4	C1—C2—H2C	109.5
C17B—C16B—H16B	110.4	C1—C2—H2D	109.5
H16A—C16B—H16B	108.6	C1—C2—H2E	109.5
C9A—C8A—H8A	108.6	O4—C1—C2	115.9 (5)
C14A—C8A—H8A	108.6	O3—C1—O4	123.3 (4)
C14A—C8A—C9A	108.4 (2)	O3—C1—C2	120.7 (5)
C7A—C8A—H8A	108.6	H2WA—O2W—H2WB	102 (3)
C7A—C8A—C9A	111.2 (2)	H1WA—O1WA—H1WB	104.5
C7A—C8A—C14A	111.4 (2)	H1WC—O1WB—H1WD	104.5
C17A—O2A—H2A	109.5
Cl1B—C4B—C5B—C10B	179.1 (2)	Cl1A—C4A—C5A—C10A	177.63 (19)
Cl1B—C4B—C5B—C6B	2.3 (4)	Cl1A—C4A—C5A—C6A	1.1 (4)
Cl1B—C4B—C3B—O1B	1.9 (4)	Cl1A—C4A—C3A—O1A	0.6 (4)
Cl1B—C4B—C3B—C2B	−177.0 (2)	Cl1A—C4A—C3A—C2A	−178.9 (2)
O1B—C3B—C2B—C1B	177.9 (3)	C8A—C9A—C11A—C12A	54.5 (3)
C9B—C8B—C7B—C6B	−55.3 (3)	C8A—C9A—C10A—C5A	−54.0 (3)
C9B—C10B—C1B—C2B	118.0 (4)	C8A—C9A—C10A—C19A	65.6 (3)
C14B—C13B—C12B—C11B	56.1 (3)	C8A—C9A—C10A—C1A	−176.4 (2)
C14B—C13B—C17B—O2B	−157.9 (2)	C8A—C14A—C13A—C18A	61.9 (3)
C14B—C13B—C17B—C20B	79.9 (3)	C8A—C14A—C13A—C12A	−59.2 (3)
C14B—C13B—C17B—C16B	−41.0 (3)	C8A—C14A—C13A—C17A	177.0 (2)
C14B—C8B—C7B—C6B	−176.4 (2)	C8A—C14A—C15A—C16A	−163.0 (3)
C14B—C15B—C16B—C17B	6.9 (4)	O2A—C17A—C16A—C15A	136.4 (3)
C13B—C14B—C8B—C9B	56.4 (3)	C9A—C8A—C14A—C13A	57.8 (3)
C13B—C14B—C8B—C7B	178.7 (2)	C9A—C8A—C14A—C15A	−179.1 (2)
C13B—C14B—C15B—C16B	−33.1 (3)	C9A—C8A—C7A—C6A	−54.4 (3)
C13B—C12B—C11B—C9B	−55.4 (3)	C9A—C11A—C12A—C13A	−55.5 (3)
C13B—C17B—C16B—C15B	21.3 (3)	C9A—C10A—C5A—C4A	−119.3 (3)
C8B—C9B—C10B—C5B	−53.4 (3)	C9A—C10A—C5A—C6A	57.5 (3)
C8B—C9B—C10B—C1B	−175.2 (2)	C9A—C10A—C1A—C2A	119.2 (3)
C8B—C9B—C10B—C19B	66.7 (3)	C14A—C8A—C9A—C11A	−53.8 (3)
C8B—C9B—C11B—C12B	53.6 (3)	C14A—C8A—C9A—C10A	177.3 (2)
C8B—C14B—C13B—C12B	−58.7 (3)	C14A—C8A—C7A—C6A	−175.5 (2)
C8B—C14B—C13B—C18B	61.9 (3)	C14A—C13A—C12A—C11A	55.6 (3)
C8B—C14B—C13B—C17B	177.2 (2)	C14A—C13A—C17A—O2A	−158.9 (2)
C8B—C14B—C15B—C16B	−161.6 (3)	C14A—C13A—C17A—C20A	81.5 (3)
C4B—C5B—C10B—C9B	−121.0 (3)	C14A—C13A—C17A—C16A	−39.2 (3)
C4B—C5B—C10B—C1B	−1.4 (4)	C14A—C15A—C16A—C17A	9.7 (3)
C4B—C5B—C10B—C19B	117.5 (3)	C4A—C5A—C6A—C7A	118.5 (3)
C4B—C5B—C6B—C7B	119.7 (3)	C4A—C3A—C2A—C1A	1.1 (5)
C4B—C3B—C2B—C1B	−3.2 (5)	C11A—C9A—C10A—C5A	178.5 (2)
O2B—C17B—C16B—C15B	141.6 (3)	C11A—C9A—C10A—C19A	−61.9 (3)
C5B—C4B—C3B—O1B	179.7 (3)	C11A—C9A—C10A—C1A	56.1 (3)
C5B—C4B—C3B—C2B	0.8 (4)	C18A—C13A—C12A—C11A	−66.8 (3)
C5B—C10B—C1B—C2B	−1.0 (5)	C18A—C13A—C17A—O2A	−41.4 (3)
C5B—C6B—C7B—C8B	55.3 (3)	C18A—C13A—C17A—C20A	−160.9 (3)
C3B—C4B—C5B—C10B	1.5 (4)	C18A—C13A—C17A—C16A	78.4 (3)
C3B—C4B—C5B—C6B	−175.3 (3)	C13A—C14A—C15A—C16A	−35.0 (3)
C10B—C9B—C8B—C14B	177.6 (2)	C13A—C17A—C16A—C15A	18.6 (3)
C10B—C9B—C8B—C7B	54.5 (3)	C10A—C9A—C11A—C12A	−177.9 (2)
C10B—C9B—C11B—C12B	−177.3 (2)	C10A—C5A—C6A—C7A	−58.3 (3)
C10B—C5B—C6B—C7B	−57.3 (3)	C10A—C1A—C2A—C3A	−1.4 (5)
C10B—C1B—C2B—C3B	3.4 (6)	C12A—C13A—C17A—O2A	83.9 (3)
C12B—C13B—C17B—O2B	84.7 (3)	C12A—C13A—C17A—C20A	−35.7 (4)
C12B—C13B—C17B—C20B	−37.5 (4)	C12A—C13A—C17A—C16A	−156.4 (3)
C12B—C13B—C17B—C16B	−158.4 (3)	C5A—C4A—C3A—O1A	179.8 (3)
C6B—C5B—C10B—C9B	56.1 (3)	C5A—C4A—C3A—C2A	0.4 (4)
C6B—C5B—C10B—C1B	175.6 (3)	C5A—C10A—C1A—C2A	0.2 (4)
C6B—C5B—C10B—C19B	−65.5 (3)	C5A—C6A—C7A—C8A	54.5 (3)
C15B—C14B—C13B—C12B	170.0 (3)	O1A—C3A—C2A—C1A	−178.3 (3)
C15B—C14B—C13B—C18B	−69.4 (3)	C19A—C10A—C5A—C4A	120.2 (3)
C15B—C14B—C13B—C17B	45.9 (3)	C19A—C10A—C5A—C6A	−63.0 (3)
C15B—C14B—C8B—C9B	179.6 (2)	C19A—C10A—C1A—C2A	−120.3 (3)
C15B—C14B—C8B—C7B	−58.1 (3)	C15A—C14A—C13A—C18A	−68.8 (3)
C18B—C13B—C12B—C11B	−66.3 (3)	C15A—C14A—C13A—C12A	170.1 (2)
C18B—C13B—C17B—O2B	−40.2 (3)	C15A—C14A—C13A—C17A	46.3 (3)
C18B—C13B—C17B—C20B	−162.3 (3)	C17A—C13A—C12A—C11A	168.3 (2)
C18B—C13B—C17B—C16B	76.7 (3)	C7A—C8A—C9A—C11A	−176.6 (2)
C11B—C9B—C8B—C14B	−52.3 (3)	C7A—C8A—C9A—C10A	54.5 (3)
C11B—C9B—C8B—C7B	−175.4 (3)	C7A—C8A—C14A—C13A	−179.5 (2)
C11B—C9B—C10B—C5B	177.3 (2)	C7A—C8A—C14A—C15A	−56.4 (3)
C11B—C9B—C10B—C1B	55.5 (3)	C3A—C4A—C5A—C10A	−1.5 (4)
C11B—C9B—C10B—C19B	−62.6 (3)	C3A—C4A—C5A—C6A	−178.1 (3)
C17B—C13B—C12B—C11B	169.1 (3)	C1A—C10A—C5A—C4A	1.2 (4)
C19B—C10B—C1B—C2B	−121.2 (4)	C1A—C10A—C5A—C6A	178.0 (2)
C20B—C17B—C16B—C15B	−101.7 (3)	C20A—C17A—C16A—C15A	−104.0 (3)

4-Chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one 2,2,2_trifluoroethanol hemisolvate (TBOL4)

Crystal data

2C20H27ClO2·C2H3F3O	Dx = 1.293 Mg m^−3
Mr = 769.77	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 7938 reflections
a = 10.3088 (3) Å	θ = 3.7–68.8°
b = 12.9337 (3) Å	µ = 1.95 mm^−1
c = 29.6661 (7) Å	T = 293 K
V = 3955.44 (17) Å^3	Plate, colourless
Z = 4	0.1 × 0.1 × 0.02 mm
F(000) = 1640

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Eos detector	7527 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	6093 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 16.4335 pixels mm^-1	θmax = 70.9°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −15→14
Tmin = 0.701, Tmax = 1.000	l = −36→35
27841 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 0.6178P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.34 e Å^−3
7527 reflections	Δρmin = −0.29 e Å^−3
484 parameters	Absolute structure: Flack x determined using 2168 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.001 (9)
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cl1B	0.66677 (11)	0.89280 (10)	0.03824 (4)	0.0663 (3)
Cl1A	0.46649 (12)	1.05544 (12)	−0.03647 (4)	0.0781 (4)
O2A	0.0135 (3)	0.7075 (3)	0.21636 (10)	0.0681 (9)
H2A	−0.016750	0.653529	0.206313	0.102*
O1	0.8808 (3)	1.5046 (3)	0.18663 (12)	0.0661 (8)
O2B	0.0522 (3)	1.3413 (2)	0.20598 (11)	0.0600 (8)
O1B	0.6300 (4)	0.7247 (3)	0.10073 (13)	0.0784 (10)
C9B	0.4369 (3)	1.0677 (3)	0.16339 (12)	0.0406 (8)
H9B	0.375949	1.022179	0.147591	0.049*
C5B	0.6123 (4)	1.0001 (3)	0.11402 (14)	0.0491 (9)
C14A	0.1957 (4)	0.7863 (3)	0.11457 (13)	0.0444 (8)
H14A	0.253382	0.836193	0.129291	0.053*
C11B	0.3809 (4)	1.0832 (3)	0.21068 (13)	0.0515 (9)
H11A	0.376496	1.016891	0.225871	0.062*
H11B	0.438648	1.127451	0.227850	0.062*
C8B	0.4385 (4)	1.1699 (3)	0.13665 (13)	0.0441 (8)
H8B	0.495443	1.219055	0.152164	0.053*
C5A	0.2466 (4)	0.9746 (3)	−0.00289 (13)	0.0477 (9)
C8A	0.1812 (4)	0.8229 (3)	0.06606 (13)	0.0443 (8)
H8A	0.121591	0.776353	0.050210	0.053*
C4A	0.3099 (4)	1.0607 (4)	−0.01551 (13)	0.0547 (10)
C13A	0.0690 (4)	0.7875 (3)	0.14167 (13)	0.0445 (8)
C9A	0.1230 (3)	0.9329 (3)	0.06631 (12)	0.0419 (8)
H9A	0.184993	0.976299	0.082735	0.050*
C7A	0.3108 (4)	0.8224 (3)	0.04202 (15)	0.0542 (10)
H7AA	0.341949	0.751754	0.039968	0.065*
H7AB	0.372947	0.861392	0.059723	0.065*
C13B	0.2428 (4)	1.2328 (3)	0.18353 (12)	0.0419 (8)
C10A	0.1120 (4)	0.9807 (3)	0.01780 (13)	0.0458 (9)
C4B	0.6282 (4)	0.9071 (3)	0.09480 (14)	0.0500 (9)
C11A	−0.0043 (4)	0.9366 (3)	0.09347 (13)	0.0502 (9)
H11C	−0.035687	1.007244	0.094567	0.060*
H11D	−0.069399	0.894922	0.078377	0.060*
C18B	0.3187 (5)	1.3153 (3)	0.20943 (15)	0.0570 (10)
H18A	0.408898	1.296958	0.210146	0.086*
H18B	0.286129	1.319888	0.239685	0.086*
H18C	0.308668	1.380962	0.194717	0.086*
C1B	0.5561 (4)	0.9079 (3)	0.18549 (15)	0.0574 (10)
H1B	0.530995	0.907925	0.215598	0.069*
C17A	0.1172 (4)	0.7429 (3)	0.18733 (14)	0.0549 (10)
C15A	0.2534 (5)	0.6789 (3)	0.12423 (15)	0.0603 (11)
H15C	0.347277	0.680415	0.122351	0.072*
H15D	0.220506	0.628058	0.103091	0.072*
C6B	0.6217 (5)	1.1001 (4)	0.08908 (16)	0.0620 (11)
H6BA	0.649115	1.087366	0.058304	0.074*
H6BB	0.685583	1.144336	0.103357	0.074*
C3B	0.6135 (4)	0.8080 (3)	0.11890 (16)	0.0560 (10)
C14B	0.3005 (4)	1.2135 (3)	0.13643 (12)	0.0432 (8)
H14B	0.246074	1.160162	0.122522	0.052*
C2B	0.5758 (5)	0.8168 (4)	0.16605 (16)	0.0614 (11)
H2BA	0.565138	0.756928	0.183011	0.074*
C12A	0.0146 (4)	0.8965 (3)	0.14156 (14)	0.0542 (10)
H12C	0.073494	0.941994	0.157593	0.065*
H12D	−0.067978	0.897181	0.157222	0.065*
C20B	0.0070 (5)	1.1968 (4)	0.1583 (2)	0.0769 (15)
H20A	−0.010980	1.153853	0.183878	0.115*
H20B	0.039512	1.154954	0.134035	0.115*
H20C	−0.071178	1.230827	0.148826	0.115*
C2A	0.1256 (5)	1.1721 (4)	0.00705 (18)	0.0707 (13)
H2AA	0.086688	1.236607	0.009838	0.085*
F1	0.6080 (4)	1.4283 (4)	0.12197 (13)	0.1126 (13)
C7B	0.4887 (5)	1.1538 (3)	0.08917 (14)	0.0580 (11)
H7BA	0.496023	1.220223	0.074191	0.070*
H7BB	0.427237	1.112086	0.072381	0.070*
F2	0.6088 (5)	1.5087 (6)	0.18289 (17)	0.182 (3)
C12B	0.2456 (4)	1.1316 (3)	0.20976 (14)	0.0528 (9)
H12A	0.185283	1.083322	0.196104	0.063*
H12B	0.217129	1.144323	0.240431	0.063*
C18A	−0.0322 (4)	0.7133 (4)	0.12193 (15)	0.0602 (11)
H18D	−0.056398	0.736164	0.092320	0.090*
H18E	−0.107401	0.712211	0.140995	0.090*
H18F	0.003963	0.644991	0.120114	0.090*
C6A	0.3040 (4)	0.8684 (3)	−0.00526 (14)	0.0554 (10)
H6AA	0.390322	0.871880	−0.018158	0.066*
H6AB	0.250916	0.824808	−0.024435	0.066*
O1A	0.3142 (5)	1.2415 (3)	−0.02535 (18)	0.1152 (17)
C1A	0.0626 (5)	1.0891 (4)	0.02066 (15)	0.0607 (11)
H1A	−0.019393	1.098827	0.033049	0.073*
C17B	0.1083 (4)	1.2776 (3)	0.17097 (14)	0.0513 (9)
C19B	0.6762 (5)	1.0706 (4)	0.19002 (17)	0.0712 (13)
H19A	0.681363	1.140262	0.178976	0.107*
H19B	0.758759	1.037322	0.186390	0.107*
H19C	0.653164	1.071499	0.221376	0.107*
C15B	0.2715 (5)	1.3136 (3)	0.11092 (14)	0.0591 (11)
H15A	0.265369	1.301221	0.078744	0.071*
H15B	0.337962	1.365145	0.116476	0.071*
C20A	0.1897 (5)	0.8204 (4)	0.21676 (16)	0.0717 (14)
H20D	0.131972	0.875253	0.225318	0.108*
H20E	0.261462	0.848560	0.200172	0.108*
H20F	0.221329	0.786281	0.243308	0.108*
F3	0.6815 (5)	1.3590 (4)	0.1811 (2)	0.187 (3)
C19A	0.0153 (4)	0.9202 (4)	−0.01215 (15)	0.0638 (12)
H19D	0.018415	0.946707	−0.042352	0.096*
H19E	−0.070910	0.928101	−0.000362	0.096*
H19F	0.038243	0.848272	−0.012298	0.096*
C2	0.8045 (5)	1.4860 (4)	0.14812 (17)	0.0699 (13)
H2C	0.850051	1.438014	0.128606	0.084*
H2D	0.793913	1.550332	0.131724	0.084*
C10B	0.5711 (4)	1.0102 (3)	0.16295 (14)	0.0483 (9)
C1	0.6778 (6)	1.4443 (5)	0.15821 (18)	0.0775 (15)
C16B	0.1396 (5)	1.3479 (4)	0.13052 (15)	0.0658 (12)
H16A	0.144018	1.419504	0.140150	0.079*
H16B	0.072386	1.341805	0.107787	0.079*
C3A	0.2553 (5)	1.1646 (4)	−0.01230 (18)	0.0716 (14)
C16A	0.2083 (5)	0.6542 (4)	0.17280 (17)	0.0675 (13)
H16C	0.162677	0.588678	0.173569	0.081*
H16D	0.282317	0.650111	0.192906	0.081*
H1	0.933 (5)	1.458 (4)	0.192 (2)	0.09 (2)*
H2B	0.043 (8)	1.306 (5)	0.2290 (17)	0.14 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1B	0.0573 (6)	0.0862 (8)	0.0552 (6)	0.0104 (6)	0.0068 (5)	−0.0107 (5)
Cl1A	0.0643 (7)	0.1033 (10)	0.0666 (7)	−0.0283 (7)	0.0067 (6)	0.0222 (7)
O2A	0.081 (2)	0.067 (2)	0.0560 (18)	−0.0239 (17)	0.0189 (17)	−0.0011 (15)
O1	0.067 (2)	0.0555 (18)	0.076 (2)	−0.0040 (17)	−0.0102 (17)	−0.0042 (17)
O2B	0.0643 (19)	0.0545 (17)	0.0613 (19)	0.0144 (15)	0.0063 (15)	−0.0060 (15)
O1B	0.095 (3)	0.060 (2)	0.080 (2)	0.0095 (19)	0.002 (2)	−0.0157 (18)
C9B	0.0403 (18)	0.0422 (19)	0.0393 (18)	−0.0032 (16)	−0.0011 (14)	0.0018 (15)
C5B	0.0379 (19)	0.058 (2)	0.051 (2)	0.0010 (18)	0.0028 (17)	−0.0001 (18)
C14A	0.046 (2)	0.0418 (19)	0.045 (2)	−0.0061 (16)	0.0038 (16)	0.0003 (16)
C11B	0.059 (2)	0.056 (2)	0.0397 (19)	0.008 (2)	0.0048 (17)	0.0067 (17)
C8B	0.047 (2)	0.0425 (19)	0.0431 (19)	−0.0021 (16)	0.0037 (16)	0.0000 (16)
C5A	0.050 (2)	0.054 (2)	0.0389 (19)	−0.0096 (18)	−0.0030 (17)	−0.0040 (16)
C8A	0.044 (2)	0.0418 (19)	0.047 (2)	−0.0071 (16)	0.0080 (17)	−0.0090 (16)
C4A	0.052 (2)	0.070 (3)	0.043 (2)	−0.018 (2)	−0.0069 (17)	0.0133 (19)
C13A	0.045 (2)	0.046 (2)	0.0419 (19)	−0.0086 (17)	0.0057 (16)	−0.0073 (16)
C9A	0.0393 (18)	0.0422 (19)	0.0440 (19)	−0.0036 (16)	0.0024 (15)	−0.0076 (16)
C7A	0.048 (2)	0.052 (2)	0.062 (3)	0.0031 (18)	0.017 (2)	−0.0023 (19)
C13B	0.0430 (19)	0.0428 (19)	0.0399 (19)	0.0004 (16)	−0.0015 (16)	−0.0019 (15)
C10A	0.045 (2)	0.050 (2)	0.043 (2)	−0.0059 (17)	−0.0010 (16)	−0.0016 (17)
C4B	0.0355 (18)	0.063 (2)	0.052 (2)	0.0038 (18)	0.0005 (16)	−0.006 (2)
C11A	0.046 (2)	0.054 (2)	0.050 (2)	0.0017 (18)	0.0075 (17)	−0.0030 (18)
C18B	0.063 (3)	0.057 (2)	0.051 (2)	−0.004 (2)	−0.005 (2)	−0.0134 (19)
C1B	0.063 (3)	0.061 (2)	0.048 (2)	0.017 (2)	−0.0050 (19)	0.005 (2)
C17A	0.059 (2)	0.059 (2)	0.047 (2)	−0.014 (2)	0.0096 (19)	0.0022 (19)
C15A	0.059 (3)	0.059 (2)	0.063 (3)	0.008 (2)	0.006 (2)	0.001 (2)
C6B	0.063 (3)	0.059 (3)	0.064 (3)	0.001 (2)	0.020 (2)	0.005 (2)
C3B	0.048 (2)	0.058 (3)	0.062 (3)	0.007 (2)	−0.006 (2)	−0.010 (2)
C14B	0.048 (2)	0.0423 (19)	0.0390 (18)	−0.0021 (16)	−0.0017 (16)	−0.0008 (16)
C2B	0.071 (3)	0.056 (3)	0.058 (3)	0.014 (2)	−0.001 (2)	0.008 (2)
C12A	0.054 (2)	0.055 (2)	0.054 (2)	−0.002 (2)	0.0130 (19)	−0.0107 (19)
C20B	0.052 (3)	0.076 (3)	0.103 (4)	0.004 (2)	−0.017 (3)	−0.023 (3)
C2A	0.080 (3)	0.057 (3)	0.075 (3)	0.008 (3)	−0.017 (3)	0.012 (2)
F1	0.094 (2)	0.150 (3)	0.094 (2)	−0.040 (2)	−0.033 (2)	0.017 (2)
C7B	0.074 (3)	0.054 (2)	0.046 (2)	0.004 (2)	0.015 (2)	0.0085 (18)
F2	0.096 (3)	0.335 (9)	0.115 (4)	0.046 (4)	0.014 (3)	−0.052 (5)
C12B	0.056 (2)	0.055 (2)	0.047 (2)	0.006 (2)	0.0086 (19)	0.0093 (18)
C18A	0.058 (3)	0.064 (3)	0.060 (3)	−0.021 (2)	0.005 (2)	−0.005 (2)
C6A	0.058 (2)	0.056 (2)	0.052 (2)	−0.008 (2)	0.0155 (19)	−0.0128 (19)
O1A	0.105 (3)	0.076 (3)	0.165 (5)	−0.027 (2)	−0.020 (3)	0.057 (3)
C1A	0.064 (3)	0.064 (3)	0.054 (2)	0.009 (2)	−0.004 (2)	0.004 (2)
C17B	0.053 (2)	0.053 (2)	0.047 (2)	0.0046 (19)	−0.0030 (18)	−0.0080 (18)
C19B	0.050 (2)	0.081 (3)	0.082 (3)	0.003 (2)	−0.019 (2)	−0.021 (3)
C15B	0.077 (3)	0.054 (2)	0.046 (2)	0.011 (2)	0.004 (2)	0.0086 (18)
C20A	0.080 (3)	0.082 (3)	0.053 (3)	−0.026 (3)	−0.004 (2)	−0.001 (2)
F3	0.171 (5)	0.186 (5)	0.205 (5)	−0.117 (4)	−0.101 (4)	0.133 (4)
C19A	0.049 (2)	0.088 (3)	0.054 (2)	−0.015 (2)	−0.0044 (19)	−0.007 (2)
C2	0.066 (3)	0.078 (3)	0.066 (3)	−0.016 (3)	−0.002 (2)	0.000 (2)
C10B	0.043 (2)	0.055 (2)	0.047 (2)	0.0027 (18)	−0.0048 (16)	−0.0064 (17)
C1	0.073 (3)	0.094 (4)	0.066 (3)	−0.022 (3)	−0.009 (3)	0.013 (3)
C16B	0.082 (3)	0.063 (3)	0.053 (2)	0.023 (2)	−0.004 (2)	0.007 (2)
C3A	0.079 (3)	0.060 (3)	0.076 (3)	−0.015 (3)	−0.027 (3)	0.026 (2)
C16A	0.074 (3)	0.060 (3)	0.068 (3)	0.000 (2)	0.007 (2)	0.009 (2)

Geometric parameters (Å, º)

Cl1B—C4B	1.734 (4)	C7A—C6A	1.525 (6)
Cl1A—C4A	1.731 (4)	C13B—C18B	1.530 (5)
O2A—C17A	1.448 (5)	C13B—C14B	1.539 (5)
O1—C2	1.408 (6)	C13B—C12B	1.523 (5)
O2B—C17B	1.446 (5)	C13B—C17B	1.549 (5)
O1B—C3B	1.216 (5)	C10A—C1A	1.494 (6)
C9B—C11B	1.530 (5)	C10A—C19A	1.548 (6)
C9B—C8B	1.542 (5)	C4B—C3B	1.476 (6)
C9B—C10B	1.571 (5)	C11A—C12A	1.530 (6)
C5B—C4B	1.341 (6)	C1B—C2B	1.328 (6)
C5B—C6B	1.493 (6)	C1B—C10B	1.490 (6)
C5B—C10B	1.518 (6)	C17A—C20A	1.525 (6)
C14A—C8A	1.522 (5)	C17A—C16A	1.543 (7)
C14A—C13A	1.534 (5)	C15A—C16A	1.547 (6)
C14A—C15A	1.538 (6)	C6B—C7B	1.537 (7)
C11B—C12B	1.530 (6)	C3B—C2B	1.456 (6)
C8B—C14B	1.529 (5)	C14B—C15B	1.529 (5)
C8B—C7B	1.515 (5)	C20B—C17B	1.524 (6)
C5A—C4A	1.344 (6)	C2A—C1A	1.318 (7)
C5A—C10A	1.520 (6)	C2A—C3A	1.458 (8)
C5A—C6A	1.497 (6)	F1—C1	1.310 (6)
C8A—C9A	1.544 (5)	F2—C1	1.317 (8)
C8A—C7A	1.515 (5)	O1A—C3A	1.228 (6)
C4A—C3A	1.460 (7)	C17B—C16B	1.540 (6)
C13A—C17A	1.554 (6)	C19B—C10B	1.559 (6)
C13A—C12A	1.518 (6)	C15B—C16B	1.544 (7)
C13A—C18A	1.533 (5)	F3—C1	1.296 (7)
C9A—C10A	1.570 (5)	C2—C1	1.444 (7)
C9A—C11A	1.541 (5)
C11B—C9B—C8B	111.3 (3)	C2B—C1B—C10B	125.2 (4)
C11B—C9B—C10B	113.7 (3)	O2A—C17A—C13A	113.5 (4)
C8B—C9B—C10B	113.1 (3)	O2A—C17A—C20A	103.3 (3)
C4B—C5B—C6B	123.9 (4)	O2A—C17A—C16A	112.4 (4)
C4B—C5B—C10B	121.2 (4)	C20A—C17A—C13A	114.3 (4)
C6B—C5B—C10B	114.7 (4)	C20A—C17A—C16A	110.5 (4)
C8A—C14A—C13A	114.1 (3)	C16A—C17A—C13A	103.1 (3)
C8A—C14A—C15A	119.6 (3)	C14A—C15A—C16A	104.1 (4)
C13A—C14A—C15A	103.9 (3)	C5B—C6B—C7B	109.5 (4)
C12B—C11B—C9B	112.4 (3)	O1B—C3B—C4B	122.7 (4)
C14B—C8B—C9B	107.9 (3)	O1B—C3B—C2B	122.1 (4)
C7B—C8B—C9B	111.3 (3)	C2B—C3B—C4B	115.1 (4)
C7B—C8B—C14B	111.4 (3)	C8B—C14B—C13B	114.5 (3)
C4A—C5A—C10A	120.9 (4)	C15B—C14B—C8B	119.7 (3)
C4A—C5A—C6A	123.8 (4)	C15B—C14B—C13B	103.7 (3)
C6A—C5A—C10A	115.3 (3)	C1B—C2B—C3B	121.8 (4)
C14A—C8A—C9A	108.6 (3)	C13A—C12A—C11A	111.3 (3)
C7A—C8A—C14A	110.9 (3)	C1A—C2A—C3A	121.3 (5)
C7A—C8A—C9A	110.4 (3)	C8B—C7B—C6B	111.6 (4)
C5A—C4A—Cl1A	121.3 (4)	C13B—C12B—C11B	112.2 (3)
C5A—C4A—C3A	123.9 (4)	C5A—C6A—C7A	109.5 (3)
C3A—C4A—Cl1A	114.8 (3)	C2A—C1A—C10A	125.3 (4)
C14A—C13A—C17A	100.4 (3)	O2B—C17B—C13B	113.5 (3)
C12A—C13A—C14A	108.8 (3)	O2B—C17B—C20B	107.1 (4)
C12A—C13A—C17A	117.7 (3)	O2B—C17B—C16B	107.9 (3)
C12A—C13A—C18A	109.2 (4)	C20B—C17B—C13B	114.6 (4)
C18A—C13A—C14A	111.9 (3)	C20B—C17B—C16B	110.8 (4)
C18A—C13A—C17A	108.6 (3)	C16B—C17B—C13B	102.8 (3)
C8A—C9A—C10A	112.7 (3)	C14B—C15B—C16B	103.3 (3)
C11A—C9A—C8A	111.2 (3)	O1—C2—C1	113.6 (4)
C11A—C9A—C10A	113.9 (3)	C5B—C10B—C9B	107.2 (3)
C8A—C7A—C6A	113.0 (4)	C5B—C10B—C19B	109.9 (4)
C18B—C13B—C14B	111.8 (3)	C1B—C10B—C9B	109.0 (3)
C18B—C13B—C17B	108.5 (3)	C1B—C10B—C5B	112.5 (3)
C14B—C13B—C17B	100.9 (3)	C1B—C10B—C19B	106.6 (4)
C12B—C13B—C18B	109.5 (3)	C19B—C10B—C9B	111.7 (3)
C12B—C13B—C14B	108.5 (3)	F1—C1—F2	105.0 (5)
C12B—C13B—C17B	117.5 (3)	F1—C1—C2	112.7 (5)
C5A—C10A—C9A	106.5 (3)	F2—C1—C2	111.6 (6)
C5A—C10A—C19A	109.3 (3)	F3—C1—F1	108.2 (5)
C1A—C10A—C5A	112.5 (4)	F3—C1—F2	105.2 (6)
C1A—C10A—C9A	110.0 (3)	F3—C1—C2	113.6 (6)
C1A—C10A—C19A	106.7 (4)	C17B—C16B—C15B	107.9 (3)
C19A—C10A—C9A	111.9 (3)	C2A—C3A—C4A	116.1 (4)
C5B—C4B—Cl1B	122.4 (3)	O1A—C3A—C4A	122.3 (5)
C5B—C4B—C3B	124.1 (4)	O1A—C3A—C2A	121.6 (5)
C3B—C4B—Cl1B	113.5 (3)	C17A—C16A—C15A	106.8 (4)
C12A—C11A—C9A	111.6 (3)