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).
Supporting information
CCDC references: 2112860; 2112861; 2112862; 2112863
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-17
β-hydroxy-17
α-methylandrosta-1,4-dien-3-one hemihydrate (TBOL1)
top
Crystal data top
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) Å3 | T = 293 K |
Z = 6 | Block, colourless |
F(000) = 1110 | 0.15 × 0.1 × 0.1 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.3945P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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-17
β-hydroxy-17
α-methylandrosta-1,4-dien-3-one (TBOL2)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.11 × 0.10 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0897P)2 + 0.0816P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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-17
β-hydroxy-17
α-methylandrosta-1,4-dien-3-one
acetic acid hemisolvate hemihydrate (TBOL3)
top
Crystal data top
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) Å3 | T = 293 K |
Z = 8 | Needle, colourless |
F(000) = 3216 | 0.1 × 0.02 × 0.01 mm |
Data collection top
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0382P)2 + 2.5992P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.042 | (Δ/σ)max < 0.001 |
wR(F2) = 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+0.001xFc2λ3/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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-17
β-hydroxy-17
α-methylandrosta-1,4-dien-3-one
2,2,2_trifluoroethanol hemisolvate (TBOL4)
top
Crystal data top
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) Å3 | Plate, colourless |
Z = 4 | 0.1 × 0.1 × 0.02 mm |
F(000) = 1640 | |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.6178P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) | | |
Interaction energies for selected contacts (kJ mol-1) topCrystal | Interaction pair | Contact | Eele | Epol | Edisp | Erep | Etot |
TBOL-1 | TBOL–water | O3—H3···O1 | -27.5 | -4.1 | -4.2 | 15.8 | -20.0 |
| TBOL–water | O2—H2···O3 | -31.6 | -5.3 | -5.9 | 16.6 | -26.2 |
| TBOL–TBOL | C7—H7A···H22B-C22 | -10.8 | -3.3 | -55.0 | 17.3 | -51.8 |
| TBOL–TBOL | C19—H19A···H7B-C7 | -7.6 | -1.8 | -31.0 | 10.6 | -29.8 |
| TBOL–TBOL | C1—H1···O2 | -7.5 | -1.7 | -23.2 | 10.6 | -21.8 |
TBOL-2 | TBOL A–TBOL B | C7A—H7AB···Cl1B | -16.5 | -5.1 | -79.6 | 33.0 | -68.2 |
| TBOL B–TBOL A | O2B—H2B···O1A | -26.1 | -5.2 | -10.6 | 11.6 | -30.3 |
| TBOL A–TBOL B | O2A—H2A···O1B | -30.5 | -5.3 | -13.1 | 18.1 | -30.9 |
| TBOL A–TBOL B | C11A—H11C···Cl1B | -4.5 | -1.8 | -27.5 | 9.7 | -24.1 |
| TBOL A–TBOL B | C6A—H6AB···O1B | -12.7 | -4.1 | -16.9 | 9.3 | -24.4 |
| TBOL B–TBOL B | C19B—H19C···O2B | -7.8 | -1.7 | -22.5 | 11.1 | -20.9 |
| TBOL B–TBOL B | C1B—H1B···Cl1A | -8.7 | -2.3 | -11.0 | 4.7 | -17.3 |
TBOL-3 | TBOL A–TBOL B | C7B—H7BB···C4A | -14.7 | -4.7 | -79.3 | 30.8 | -67.9 |
| TBOL A–TBOL B | O2A—H2A···O1B | -28.0 | -4.7 | -13.0 | 14.3 | -31.4 |
| Water–TBOL A | O1—H1···O1A | -44.4 | -6.7 | -5.0 | 27.6 | -28.5 |
| Acetic acid–TBOL B | C2—H2E···C2B | -8.1 | -1.3 | -14.2 | 7.6 | -16.0 |
| TBOL B–TBOL B | C7—H7AB···H15B-C15B | -1.9 | -1.1 | -33.8 | 14.4 | -22.4 |
TBOL-4 | TBOL A-TBOL B | C7A—H7AB···C4B (C—H···π) | -14.0 | -4.4 | -78.5 | 31.1 | -65.8 |
| TBOL B–2,2,2-trifluoroethanol | O1—H1···O2B | -43.2 | -7.8 | -13.5 | 25.7 | -38.8 |
| TBOL A–TBOL B | O2B—H2B···O2A | -30.0 | -5.2 | -17.5 | 19.3 | -33.4 |
| TBOL A–TBOL B | C11A—H2B···Cl1B | -9.5 | -2.1 | -26.5 | 11.2 | -26.9 |
| TBOL A–2,2,2-trifluoroethanol | O2A—H2A···O1 | -19.4 | -2.9 | -14.4 | 15.6 | -21.1 |
| TBOL A–TBOL B | C6A—H6AB···O1B | -11.7 | -4.0 | -15.1 | 8.6 | -22.2 |
| TBOL A–TBOL A | C7A—H7AA···C19A | -1.8 | -0.7 | -18.7 | 5.3 | -15.9 |
| TBOL B–2,2,2-trifluoroethanol | C8B- H8B···F3 | -2.7 | -0.5 | -14.0 | 3.7 | -13.5 |
| TBOL A–2,2,2-trifluoroethanol | C20A—H20F···F3 | -4.0 | -0.5 | -6.7 | 2.8 | -8.4 |
Crystal energies (kJ mol-1) topEcoul is Coulombic, Epol is polarization, Edisp
is dispersion, Eatt is the attraction term (sum of Coulombic,
polarization and dispersion components), Erep is repulsion and
Elatt is total crystal energy. |
Crystal | Ecoul | Epol | Edisp | Eatt | Erep | Elatt |
TBOL-1 | -17.4 | -12.7 | -27.6 | -57.7 | 15.4 | -42.3 |
TBOL-2 | -29.3 | -42.4 | -136.3 | -208.0 | 52.8 | -155.2 |
TBOL-3 | -15.7 | -16.9 | -52.38 | -84.9 | 18.4 | -66.5 |
TBOL-4 | -35.1 | -35.1 | -108.6 | -178.8 | 46.6 | -132.2 |