Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026803/bt2381sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026803/bt2381Isup2.hkl |
CCDC reference: 654877
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.090
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C50 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.05
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 4861 Count of symmetry unique reflns 3878 Completeness (_total/calc) 125.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 983 Fraction of Friedel pairs measured 0.253 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C35 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C36 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C44 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 18 ALERT level G = General alerts; check 17 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
3β-acetoxy-5α-chloro-6β-hydroxy-17-androstanone, in a form of a white powder, was synthesized according to Mousseron-Canet et al. (1968). Crystals suitable for structure analysis were obtained by slow evaporation from a mixture of tetrahydrofuran, acetone and water (volume proportion, 2:2:1) as colourless prisms (m.p. 518 K).
The absolute stereochemistry of the title compound was known from the synthetic route (Mousseron-Canet et al., 1968) and it was confirmed by the structure determination. The hydroxy atom H3X and H7X were located in a difference Fourier map but refined using a riding model with Uiso(H) = 1.2Ueq(O). Methyl H atoms were placed in calculated positions with C—H = 0.96 Å and torsion angles were refined to fit the electron density, Uiso(H) = 1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.97 or C—H = 0.98, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
Many anabolic steroids have a reduced androgenic side effect (Stanley et al., 1997). Androstane derivatives may be used for oral therapy aginst weight gain after extensive surgery, chronic infections and severe traumata (Alvarez-Ginarte et al., 2005). In continuation of our work on the structure-activity relationship of androstanone derivatives, we present here the structure of the title compound (Fig. 1).
The title compound crystallizes with two molecules in the asymmetric unit. All bond lengths and angles correspond well to those observed in similar steriod structures (Rendle et al., 1974; Xia et al., 2007). Rings A, B and C adopt a chair conformation, while ring D shows an envelope conformation. The hydroxyl group is involved in an intramolecular O—H···O hydrogen bond (Table 1).
For related literature, see: Alvarez-Ginarte, Crespo, Montero-Cabrera, Ruiz-Garcia, Ponce, Santana, Pardillo-Fontdevila & Alonso-Becerra (2005); Mousseron-Canet, Labeeuw & Lanet (1968); Rendle & Trotter (1974); Stanley et al. (1997); Xia et al. (2007).
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of one molecule in the asymmetric unit of the title compound, shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
C21H31ClO4 | Z = 2 |
Mr = 382.91 | F(000) = 412 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1025 (12) Å | Cell parameters from 2891 reflections |
b = 9.9840 (16) Å | θ = 2.4–22.1° |
c = 15.552 (3) Å | µ = 0.22 mm−1 |
α = 100.521 (2)° | T = 296 K |
β = 99.211 (2)° | Prismatic, colourless |
γ = 110.470 (2)° | 0.30 × 0.20 × 0.15 mm |
V = 985.3 (3) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 4861 independent reflections |
Radiation source: fine-focus sealed tube | 4372 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.938, Tmax = 0.962 | k = −12→12 |
5701 measured reflections | l = −19→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.128P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.14 e Å−3 |
4861 reflections | Δρmin = −0.17 e Å−3 |
476 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.007 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 983 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (5) |
C21H31ClO4 | γ = 110.470 (2)° |
Mr = 382.91 | V = 985.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.1025 (12) Å | Mo Kα radiation |
b = 9.9840 (16) Å | µ = 0.22 mm−1 |
c = 15.552 (3) Å | T = 296 K |
α = 100.521 (2)° | 0.30 × 0.20 × 0.15 mm |
β = 99.211 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 4861 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4372 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 0.962 | Rint = 0.020 |
5701 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.090 | Δρmax = 0.14 e Å−3 |
S = 1.06 | Δρmin = −0.17 e Å−3 |
4861 reflections | Absolute structure: Flack (1983), with 983 Friedel pairs |
476 parameters | Absolute structure parameter: 0.00 (5) |
3 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.17673 (11) | 0.05164 (8) | 0.62739 (5) | 0.0546 (2) | |
O1 | 0.7135 (4) | 0.4524 (2) | 0.63658 (16) | 0.0629 (6) | |
O2 | 0.6585 (6) | 0.3949 (3) | 0.4876 (2) | 0.1031 (11) | |
O3 | 0.3879 (4) | 0.2852 (2) | 0.88199 (15) | 0.0569 (6) | |
H3X | 0.3583 | 0.3580 | 0.8939 | 0.085* | |
O4 | 0.1729 (4) | −0.5336 (2) | 0.89166 (19) | 0.0684 (7) | |
C1 | 0.6278 (5) | 0.0694 (3) | 0.6709 (2) | 0.0507 (7) | |
H1A | 0.7268 | 0.0246 | 0.6836 | 0.061* | |
H1B | 0.5207 | 0.0035 | 0.6180 | 0.061* | |
C2 | 0.7389 (6) | 0.2187 (4) | 0.6503 (3) | 0.0610 (9) | |
H2A | 0.8576 | 0.2803 | 0.7000 | 0.073* | |
H2B | 0.7889 | 0.2015 | 0.5965 | 0.073* | |
C3 | 0.5950 (5) | 0.2993 (3) | 0.6362 (2) | 0.0540 (8) | |
H3 | 0.4917 | 0.2486 | 0.5786 | 0.065* | |
C4 | 0.4876 (5) | 0.3124 (3) | 0.7115 (2) | 0.0475 (7) | |
H4A | 0.3867 | 0.3543 | 0.6957 | 0.057* | |
H4B | 0.5890 | 0.3798 | 0.7657 | 0.057* | |
C5 | 0.3783 (4) | 0.1642 (3) | 0.73129 (18) | 0.0401 (6) | |
C6 | 0.2540 (5) | 0.1776 (3) | 0.8018 (2) | 0.0435 (7) | |
H6 | 0.1471 | 0.2115 | 0.7782 | 0.052* | |
C7 | 0.1487 (5) | 0.0306 (3) | 0.8224 (2) | 0.0446 (7) | |
H7A | 0.0354 | −0.0335 | 0.7711 | 0.054* | |
H7B | 0.0901 | 0.0470 | 0.8736 | 0.054* | |
C8 | 0.2942 (4) | −0.0476 (3) | 0.84321 (18) | 0.0356 (6) | |
H8 | 0.3996 | 0.0129 | 0.8989 | 0.043* | |
C9 | 0.4043 (4) | −0.0669 (3) | 0.76705 (18) | 0.0371 (6) | |
H9 | 0.2953 | −0.1227 | 0.7117 | 0.044* | |
C10 | 0.5290 (4) | 0.0854 (3) | 0.75172 (19) | 0.0392 (6) | |
C11 | 0.5344 (5) | −0.1600 (3) | 0.7817 (2) | 0.0470 (7) | |
H11A | 0.6544 | −0.1026 | 0.8316 | 0.056* | |
H11B | 0.5839 | −0.1807 | 0.7282 | 0.056* | |
C12 | 0.4125 (5) | −0.3077 (3) | 0.8018 (2) | 0.0461 (7) | |
H12A | 0.3041 | −0.3719 | 0.7489 | 0.055* | |
H12B | 0.5049 | −0.3569 | 0.8162 | 0.055* | |
C13 | 0.3171 (4) | −0.2796 (3) | 0.88046 (19) | 0.0378 (6) | |
C14 | 0.1758 (4) | −0.1985 (3) | 0.85734 (18) | 0.0373 (6) | |
H14 | 0.0798 | −0.2584 | 0.7992 | 0.045* | |
C15 | 0.0463 (5) | −0.2124 (3) | 0.9272 (2) | 0.0482 (7) | |
H15A | −0.0805 | −0.1989 | 0.9066 | 0.058* | |
H15B | 0.1236 | −0.1409 | 0.9844 | 0.058* | |
C16 | 0.0003 (5) | −0.3715 (3) | 0.9351 (3) | 0.0539 (8) | |
H16A | 0.0079 | −0.3760 | 0.9973 | 0.065* | |
H16B | −0.1365 | −0.4381 | 0.8987 | 0.065* | |
C17 | 0.1666 (5) | −0.4119 (3) | 0.9006 (2) | 0.0462 (7) | |
C18 | 0.4835 (5) | −0.1995 (3) | 0.9694 (2) | 0.0494 (7) | |
H18A | 0.5567 | −0.2607 | 0.9828 | 0.074* | |
H18B | 0.4186 | −0.1801 | 1.0172 | 0.074* | |
H18C | 0.5790 | −0.1078 | 0.9637 | 0.074* | |
C19 | 0.7040 (4) | 0.1796 (3) | 0.8360 (2) | 0.0489 (7) | |
H19A | 0.7732 | 0.2766 | 0.8283 | 0.073* | |
H19B | 0.8013 | 0.1336 | 0.8447 | 0.073* | |
H19C | 0.6468 | 0.1875 | 0.8877 | 0.073* | |
C20 | 0.7226 (6) | 0.4851 (4) | 0.5575 (3) | 0.0629 (9) | |
C21 | 0.8229 (7) | 0.6486 (4) | 0.5700 (3) | 0.0785 (12) | |
H21A | 0.8258 | 0.6694 | 0.5123 | 0.118* | |
H21B | 0.9619 | 0.6852 | 0.6064 | 0.118* | |
H21C | 0.7453 | 0.6961 | 0.5994 | 0.118* | |
Cl2 | 0.02987 (12) | 0.94245 (8) | 0.40404 (5) | 0.0557 (2) | |
O5 | 0.1815 (4) | 0.5505 (2) | 0.40842 (17) | 0.0656 (6) | |
O6 | 0.2826 (6) | 0.6093 (4) | 0.5582 (2) | 0.0982 (10) | |
O7 | −0.1161 (3) | 0.7115 (2) | 0.14985 (15) | 0.0588 (6) | |
H7X | −0.2290 | 0.6472 | 0.1372 | 0.088* | |
O8 | 0.4767 (4) | 1.5323 (2) | 0.1432 (2) | 0.0817 (8) | |
C31 | 0.4535 (5) | 0.9362 (3) | 0.3801 (2) | 0.0540 (8) | |
H31A | 0.5922 | 0.9836 | 0.3725 | 0.065* | |
H31B | 0.4369 | 1.0006 | 0.4306 | 0.065* | |
C32 | 0.4305 (6) | 0.7887 (4) | 0.4023 (3) | 0.0614 (9) | |
H32A | 0.4676 | 0.7298 | 0.3564 | 0.074* | |
H32B | 0.5256 | 0.8077 | 0.4596 | 0.074* | |
C33 | 0.2126 (5) | 0.7024 (4) | 0.4075 (2) | 0.0554 (8) | |
H33 | 0.1857 | 0.7506 | 0.4623 | 0.067* | |
C34 | 0.0500 (5) | 0.6868 (3) | 0.3261 (2) | 0.0491 (7) | |
H34A | −0.0863 | 0.6421 | 0.3368 | 0.059* | |
H34B | 0.0589 | 0.6210 | 0.2741 | 0.059* | |
C35 | 0.0747 (4) | 0.8347 (3) | 0.30524 (19) | 0.0403 (6) | |
C36 | −0.1024 (4) | 0.8177 (3) | 0.2280 (2) | 0.0451 (7) | |
H36 | −0.2326 | 0.7820 | 0.2468 | 0.054* | |
C37 | −0.0746 (4) | 0.9647 (3) | 0.2056 (2) | 0.0464 (7) | |
H37A | −0.1756 | 0.9464 | 0.1503 | 0.056* | |
H37B | −0.1027 | 1.0267 | 0.2534 | 0.056* | |
C38 | 0.1410 (4) | 1.0482 (3) | 0.19419 (19) | 0.0385 (6) | |
H38 | 0.1624 | 0.9897 | 0.1416 | 0.046* | |
C39 | 0.3107 (4) | 1.0710 (3) | 0.27751 (19) | 0.0389 (6) | |
H39 | 0.2798 | 1.1235 | 0.3295 | 0.047* | |
C40 | 0.2954 (4) | 0.9187 (3) | 0.29435 (19) | 0.0401 (6) | |
C41 | 0.5284 (4) | 1.1703 (3) | 0.2727 (2) | 0.0505 (7) | |
H41A | 0.6244 | 1.1933 | 0.3303 | 0.061* | |
H41B | 0.5726 | 1.1159 | 0.2274 | 0.061* | |
C42 | 0.5396 (5) | 1.3155 (3) | 0.2498 (2) | 0.0526 (7) | |
H42A | 0.5169 | 1.3780 | 0.2993 | 0.063* | |
H42B | 0.6760 | 1.3679 | 0.2414 | 0.063* | |
C43 | 0.3770 (4) | 1.2835 (3) | 0.1647 (2) | 0.0437 (7) | |
C44 | 0.1637 (4) | 1.1982 (3) | 0.1781 (2) | 0.0424 (6) | |
H44 | 0.1516 | 1.2563 | 0.2334 | 0.051* | |
C45 | 0.0106 (5) | 1.2077 (4) | 0.1005 (3) | 0.0588 (8) | |
H45A | −0.1234 | 1.1900 | 0.1139 | 0.071* | |
H45B | −0.0068 | 1.1376 | 0.0447 | 0.071* | |
C46 | 0.1169 (6) | 1.3678 (4) | 0.0952 (3) | 0.0687 (10) | |
H46A | 0.0955 | 1.3735 | 0.0330 | 0.082* | |
H46B | 0.0622 | 1.4316 | 0.1284 | 0.082* | |
C47 | 0.3440 (5) | 1.4129 (3) | 0.1368 (2) | 0.0566 (8) | |
C48 | 0.4288 (5) | 1.2055 (3) | 0.0830 (2) | 0.0549 (8) | |
H48A | 0.3259 | 1.1881 | 0.0295 | 0.082* | |
H48B | 0.4306 | 1.1128 | 0.0909 | 0.082* | |
H48C | 0.5624 | 1.2668 | 0.0775 | 0.082* | |
C49 | 0.3373 (5) | 0.8272 (3) | 0.2138 (2) | 0.0502 (7) | |
H49A | 0.4703 | 0.8825 | 0.2049 | 0.075* | |
H49B | 0.2318 | 0.8060 | 0.1605 | 0.075* | |
H49C | 0.3360 | 0.7361 | 0.2261 | 0.075* | |
C50 | 0.2136 (6) | 0.5192 (4) | 0.4881 (3) | 0.0652 (9) | |
C51 | 0.1468 (7) | 0.3559 (4) | 0.4753 (3) | 0.0844 (13) | |
H51A | 0.0008 | 0.3079 | 0.4482 | 0.127* | |
H51B | 0.1760 | 0.3351 | 0.5327 | 0.127* | |
H51C | 0.2209 | 0.3197 | 0.4367 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0556 (5) | 0.0553 (4) | 0.0446 (4) | 0.0200 (4) | −0.0035 (3) | 0.0104 (3) |
O1 | 0.0739 (16) | 0.0501 (12) | 0.0605 (15) | 0.0153 (11) | 0.0133 (12) | 0.0248 (11) |
O2 | 0.144 (3) | 0.088 (2) | 0.0557 (19) | 0.016 (2) | 0.0311 (19) | 0.0215 (16) |
O3 | 0.0799 (16) | 0.0516 (12) | 0.0463 (13) | 0.0407 (12) | 0.0107 (11) | 0.0035 (10) |
O4 | 0.0709 (16) | 0.0387 (11) | 0.107 (2) | 0.0280 (11) | 0.0326 (15) | 0.0214 (11) |
C1 | 0.0559 (19) | 0.0529 (16) | 0.0543 (19) | 0.0288 (15) | 0.0211 (15) | 0.0182 (14) |
C2 | 0.062 (2) | 0.066 (2) | 0.070 (2) | 0.0292 (18) | 0.0318 (18) | 0.0309 (18) |
C3 | 0.063 (2) | 0.0438 (16) | 0.0555 (19) | 0.0185 (15) | 0.0133 (16) | 0.0192 (14) |
C4 | 0.0541 (18) | 0.0419 (15) | 0.0464 (17) | 0.0210 (14) | 0.0052 (14) | 0.0129 (13) |
C5 | 0.0436 (16) | 0.0405 (13) | 0.0343 (15) | 0.0193 (12) | 0.0016 (12) | 0.0065 (11) |
C6 | 0.0477 (17) | 0.0481 (16) | 0.0485 (18) | 0.0330 (14) | 0.0120 (14) | 0.0161 (13) |
C7 | 0.0439 (17) | 0.0504 (16) | 0.0531 (18) | 0.0307 (14) | 0.0165 (14) | 0.0162 (13) |
C8 | 0.0339 (14) | 0.0362 (12) | 0.0397 (15) | 0.0192 (11) | 0.0066 (11) | 0.0076 (11) |
C9 | 0.0361 (14) | 0.0396 (13) | 0.0364 (14) | 0.0191 (11) | 0.0064 (11) | 0.0055 (11) |
C10 | 0.0395 (15) | 0.0391 (13) | 0.0432 (15) | 0.0199 (12) | 0.0109 (12) | 0.0102 (11) |
C11 | 0.0508 (18) | 0.0477 (15) | 0.0592 (19) | 0.0322 (14) | 0.0253 (15) | 0.0167 (13) |
C12 | 0.0501 (17) | 0.0405 (14) | 0.0544 (18) | 0.0271 (13) | 0.0148 (14) | 0.0074 (12) |
C13 | 0.0363 (15) | 0.0336 (12) | 0.0442 (15) | 0.0169 (11) | 0.0069 (12) | 0.0073 (11) |
C14 | 0.0346 (14) | 0.0368 (13) | 0.0401 (15) | 0.0176 (11) | 0.0060 (11) | 0.0047 (11) |
C15 | 0.0456 (17) | 0.0446 (15) | 0.061 (2) | 0.0219 (14) | 0.0208 (15) | 0.0145 (14) |
C16 | 0.0527 (19) | 0.0415 (16) | 0.071 (2) | 0.0178 (14) | 0.0224 (17) | 0.0169 (15) |
C17 | 0.0459 (17) | 0.0362 (14) | 0.0548 (18) | 0.0181 (13) | 0.0076 (13) | 0.0081 (12) |
C18 | 0.0430 (17) | 0.0507 (16) | 0.0519 (18) | 0.0190 (13) | 0.0021 (14) | 0.0139 (13) |
C19 | 0.0401 (16) | 0.0450 (15) | 0.061 (2) | 0.0175 (13) | 0.0069 (14) | 0.0138 (14) |
C20 | 0.065 (2) | 0.074 (2) | 0.058 (2) | 0.0274 (19) | 0.0231 (18) | 0.0299 (19) |
C21 | 0.081 (3) | 0.069 (2) | 0.098 (3) | 0.025 (2) | 0.034 (2) | 0.049 (2) |
Cl2 | 0.0674 (5) | 0.0598 (4) | 0.0461 (4) | 0.0281 (4) | 0.0242 (4) | 0.0128 (3) |
O5 | 0.0881 (18) | 0.0547 (12) | 0.0625 (15) | 0.0336 (13) | 0.0169 (13) | 0.0250 (11) |
O6 | 0.140 (3) | 0.096 (2) | 0.065 (2) | 0.056 (2) | 0.0091 (19) | 0.0288 (17) |
O7 | 0.0478 (13) | 0.0588 (13) | 0.0467 (13) | 0.0033 (10) | 0.0051 (10) | 0.0000 (10) |
O8 | 0.0619 (15) | 0.0400 (12) | 0.133 (3) | 0.0076 (11) | 0.0193 (16) | 0.0271 (14) |
C31 | 0.0447 (18) | 0.0548 (17) | 0.057 (2) | 0.0176 (15) | 0.0009 (15) | 0.0167 (15) |
C32 | 0.058 (2) | 0.066 (2) | 0.064 (2) | 0.0299 (17) | 0.0041 (17) | 0.0252 (17) |
C33 | 0.065 (2) | 0.0505 (16) | 0.0541 (19) | 0.0242 (16) | 0.0120 (16) | 0.0206 (15) |
C34 | 0.0514 (18) | 0.0429 (15) | 0.0513 (18) | 0.0154 (14) | 0.0143 (14) | 0.0122 (13) |
C35 | 0.0385 (15) | 0.0428 (14) | 0.0388 (15) | 0.0149 (12) | 0.0120 (12) | 0.0084 (11) |
C36 | 0.0277 (14) | 0.0485 (16) | 0.0483 (18) | 0.0035 (12) | 0.0060 (12) | 0.0124 (13) |
C37 | 0.0280 (14) | 0.0536 (16) | 0.0548 (18) | 0.0117 (13) | 0.0057 (13) | 0.0200 (14) |
C38 | 0.0295 (14) | 0.0427 (14) | 0.0374 (14) | 0.0093 (11) | 0.0066 (11) | 0.0071 (11) |
C39 | 0.0322 (14) | 0.0418 (14) | 0.0380 (15) | 0.0118 (11) | 0.0055 (11) | 0.0071 (11) |
C40 | 0.0338 (15) | 0.0411 (13) | 0.0403 (15) | 0.0113 (12) | 0.0068 (12) | 0.0076 (11) |
C41 | 0.0312 (15) | 0.0515 (16) | 0.0556 (19) | 0.0054 (13) | 0.0001 (13) | 0.0133 (14) |
C42 | 0.0377 (16) | 0.0437 (15) | 0.059 (2) | 0.0017 (13) | 0.0034 (14) | 0.0070 (14) |
C43 | 0.0372 (15) | 0.0356 (13) | 0.0489 (17) | 0.0068 (12) | 0.0091 (13) | 0.0050 (12) |
C44 | 0.0376 (15) | 0.0417 (14) | 0.0462 (17) | 0.0141 (12) | 0.0106 (13) | 0.0098 (12) |
C45 | 0.0423 (18) | 0.0583 (19) | 0.075 (2) | 0.0151 (15) | 0.0072 (16) | 0.0311 (17) |
C46 | 0.059 (2) | 0.058 (2) | 0.096 (3) | 0.0241 (17) | 0.018 (2) | 0.037 (2) |
C47 | 0.0534 (19) | 0.0433 (16) | 0.069 (2) | 0.0134 (15) | 0.0171 (17) | 0.0135 (15) |
C48 | 0.058 (2) | 0.0531 (17) | 0.053 (2) | 0.0170 (15) | 0.0225 (16) | 0.0138 (14) |
C49 | 0.0431 (17) | 0.0518 (16) | 0.0599 (19) | 0.0208 (14) | 0.0205 (15) | 0.0127 (14) |
C50 | 0.069 (2) | 0.076 (2) | 0.069 (3) | 0.038 (2) | 0.023 (2) | 0.036 (2) |
C51 | 0.096 (3) | 0.078 (3) | 0.104 (3) | 0.046 (3) | 0.030 (3) | 0.052 (2) |
Cl1—C5 | 1.842 (3) | Cl2—C35 | 1.848 (3) |
O1—C20 | 1.334 (4) | O5—C50 | 1.337 (4) |
O1—C3 | 1.463 (4) | O5—C33 | 1.456 (4) |
O2—C20 | 1.183 (5) | O6—C50 | 1.183 (5) |
O3—C6 | 1.425 (4) | O7—C36 | 1.425 (4) |
O3—H3X | 0.8229 | O7—H7X | 0.7983 |
O4—C17 | 1.215 (3) | O8—C47 | 1.209 (4) |
C1—C2 | 1.543 (4) | C31—C32 | 1.534 (4) |
C1—C10 | 1.544 (4) | C31—C40 | 1.539 (4) |
C1—H1A | 0.9700 | C31—H31A | 0.9700 |
C1—H1B | 0.9700 | C31—H31B | 0.9700 |
C2—C3 | 1.519 (5) | C32—C33 | 1.509 (5) |
C2—H2A | 0.9700 | C32—H32A | 0.9700 |
C2—H2B | 0.9700 | C32—H32B | 0.9700 |
C3—C4 | 1.507 (4) | C33—C34 | 1.515 (5) |
C3—H3 | 0.9800 | C33—H33 | 0.9800 |
C4—C5 | 1.525 (4) | C34—C35 | 1.525 (4) |
C4—H4A | 0.9700 | C34—H34A | 0.9700 |
C4—H4B | 0.9700 | C34—H34B | 0.9700 |
C5—C6 | 1.530 (4) | C35—C36 | 1.532 (4) |
C5—C10 | 1.561 (3) | C35—C40 | 1.551 (4) |
C6—C7 | 1.515 (4) | C36—C37 | 1.523 (4) |
C6—H6 | 0.9800 | C36—H36 | 0.9800 |
C7—C8 | 1.528 (3) | C37—C38 | 1.523 (4) |
C7—H7A | 0.9700 | C37—H37A | 0.9700 |
C7—H7B | 0.9700 | C37—H37B | 0.9700 |
C8—C14 | 1.523 (4) | C38—C44 | 1.520 (4) |
C8—C9 | 1.540 (3) | C38—C39 | 1.544 (4) |
C8—H8 | 0.9800 | C38—H38 | 0.9800 |
C9—C11 | 1.542 (3) | C39—C41 | 1.540 (4) |
C9—C10 | 1.553 (4) | C39—C40 | 1.559 (4) |
C9—H9 | 0.9800 | C39—H39 | 0.9800 |
C10—C19 | 1.536 (4) | C40—C49 | 1.544 (4) |
C11—C12 | 1.544 (4) | C41—C42 | 1.533 (4) |
C11—H11A | 0.9700 | C41—H41A | 0.9700 |
C11—H11B | 0.9700 | C41—H41B | 0.9700 |
C12—C13 | 1.519 (4) | C42—C43 | 1.512 (4) |
C12—H12A | 0.9700 | C42—H42A | 0.9700 |
C12—H12B | 0.9700 | C42—H42B | 0.9700 |
C13—C17 | 1.503 (4) | C43—C47 | 1.516 (4) |
C13—C14 | 1.533 (3) | C43—C44 | 1.526 (4) |
C13—C18 | 1.536 (4) | C43—C48 | 1.531 (4) |
C14—C15 | 1.527 (4) | C44—C45 | 1.530 (4) |
C14—H14 | 0.9800 | C44—H44 | 0.9800 |
C15—C16 | 1.538 (4) | C45—C46 | 1.534 (4) |
C15—H15A | 0.9700 | C45—H45A | 0.9700 |
C15—H15B | 0.9700 | C45—H45B | 0.9700 |
C16—C17 | 1.517 (4) | C46—C47 | 1.508 (5) |
C16—H16A | 0.9700 | C46—H46A | 0.9700 |
C16—H16B | 0.9700 | C46—H46B | 0.9700 |
C18—H18A | 0.9600 | C48—H48A | 0.9600 |
C18—H18B | 0.9600 | C48—H48B | 0.9600 |
C18—H18C | 0.9600 | C48—H48C | 0.9600 |
C19—H19A | 0.9600 | C49—H49A | 0.9600 |
C19—H19B | 0.9600 | C49—H49B | 0.9600 |
C19—H19C | 0.9600 | C49—H49C | 0.9600 |
C20—C21 | 1.495 (5) | C50—C51 | 1.494 (5) |
C21—H21A | 0.9600 | C51—H51A | 0.9600 |
C21—H21B | 0.9600 | C51—H51B | 0.9600 |
C21—H21C | 0.9600 | C51—H51C | 0.9600 |
C20—O1—C3 | 118.3 (3) | C50—O5—C33 | 118.4 (3) |
C6—O3—H3X | 113.1 | C36—O7—H7X | 107.3 |
C2—C1—C10 | 112.8 (2) | C32—C31—C40 | 113.2 (3) |
C2—C1—H1A | 109.0 | C32—C31—H31A | 108.9 |
C10—C1—H1A | 109.0 | C40—C31—H31A | 108.9 |
C2—C1—H1B | 109.0 | C32—C31—H31B | 108.9 |
C10—C1—H1B | 109.0 | C40—C31—H31B | 108.9 |
H1A—C1—H1B | 107.8 | H31A—C31—H31B | 107.8 |
C3—C2—C1 | 111.4 (3) | C33—C32—C31 | 112.0 (3) |
C3—C2—H2A | 109.3 | C33—C32—H32A | 109.2 |
C1—C2—H2A | 109.3 | C31—C32—H32A | 109.2 |
C3—C2—H2B | 109.3 | C33—C32—H32B | 109.2 |
C1—C2—H2B | 109.3 | C31—C32—H32B | 109.2 |
H2A—C2—H2B | 108.0 | H32A—C32—H32B | 107.9 |
O1—C3—C4 | 104.5 (2) | O5—C33—C32 | 111.1 (3) |
O1—C3—C2 | 110.2 (3) | O5—C33—C34 | 104.3 (3) |
C4—C3—C2 | 112.8 (3) | C32—C33—C34 | 112.9 (3) |
O1—C3—H3 | 109.7 | O5—C33—H33 | 109.5 |
C4—C3—H3 | 109.7 | C32—C33—H33 | 109.5 |
C2—C3—H3 | 109.7 | C34—C33—H33 | 109.5 |
C3—C4—C5 | 112.8 (2) | C33—C34—C35 | 112.7 (2) |
C3—C4—H4A | 109.0 | C33—C34—H34A | 109.0 |
C5—C4—H4A | 109.0 | C35—C34—H34A | 109.0 |
C3—C4—H4B | 109.0 | C33—C34—H34B | 109.0 |
C5—C4—H4B | 109.0 | C35—C34—H34B | 109.0 |
H4A—C4—H4B | 107.8 | H34A—C34—H34B | 107.8 |
C4—C5—C6 | 111.9 (2) | C34—C35—C36 | 111.6 (2) |
C4—C5—C10 | 111.9 (2) | C34—C35—C40 | 112.1 (2) |
C6—C5—C10 | 114.5 (2) | C36—C35—C40 | 115.0 (2) |
C4—C5—Cl1 | 105.02 (18) | C34—C35—Cl2 | 104.84 (19) |
C6—C5—Cl1 | 103.4 (2) | C36—C35—Cl2 | 103.07 (19) |
C10—C5—Cl1 | 109.34 (17) | C40—C35—Cl2 | 109.35 (18) |
O3—C6—C7 | 110.3 (2) | O7—C36—C37 | 109.9 (2) |
O3—C6—C5 | 109.4 (2) | O7—C36—C35 | 110.2 (2) |
C7—C6—C5 | 111.7 (2) | C37—C36—C35 | 111.6 (2) |
O3—C6—H6 | 108.5 | O7—C36—H36 | 108.4 |
C7—C6—H6 | 108.5 | C37—C36—H36 | 108.4 |
C5—C6—H6 | 108.5 | C35—C36—H36 | 108.4 |
C6—C7—C8 | 113.5 (2) | C38—C37—C36 | 113.8 (2) |
C6—C7—H7A | 108.9 | C38—C37—H37A | 108.8 |
C8—C7—H7A | 108.9 | C36—C37—H37A | 108.8 |
C6—C7—H7B | 108.9 | C38—C37—H37B | 108.8 |
C8—C7—H7B | 108.9 | C36—C37—H37B | 108.8 |
H7A—C7—H7B | 107.7 | H37A—C37—H37B | 107.7 |
C14—C8—C7 | 110.7 (2) | C44—C38—C37 | 111.3 (2) |
C14—C8—C9 | 109.35 (19) | C44—C38—C39 | 108.9 (2) |
C7—C8—C9 | 111.4 (2) | C37—C38—C39 | 111.4 (2) |
C14—C8—H8 | 108.5 | C44—C38—H38 | 108.3 |
C7—C8—H8 | 108.5 | C37—C38—H38 | 108.3 |
C9—C8—H8 | 108.5 | C39—C38—H38 | 108.3 |
C8—C9—C11 | 112.3 (2) | C41—C39—C38 | 112.6 (2) |
C8—C9—C10 | 110.65 (19) | C41—C39—C40 | 113.8 (2) |
C11—C9—C10 | 113.5 (2) | C38—C39—C40 | 110.2 (2) |
C8—C9—H9 | 106.6 | C41—C39—H39 | 106.5 |
C11—C9—H9 | 106.6 | C38—C39—H39 | 106.5 |
C10—C9—H9 | 106.6 | C40—C39—H39 | 106.5 |
C19—C10—C1 | 107.9 (2) | C31—C40—C49 | 107.9 (2) |
C19—C10—C9 | 109.7 (2) | C31—C40—C35 | 108.4 (2) |
C1—C10—C9 | 112.1 (2) | C49—C40—C35 | 109.8 (2) |
C19—C10—C5 | 110.6 (2) | C31—C40—C39 | 112.1 (2) |
C1—C10—C5 | 107.9 (2) | C49—C40—C39 | 109.8 (2) |
C9—C10—C5 | 108.7 (2) | C35—C40—C39 | 108.8 (2) |
C9—C11—C12 | 113.2 (2) | C42—C41—C39 | 113.7 (2) |
C9—C11—H11A | 108.9 | C42—C41—H41A | 108.8 |
C12—C11—H11A | 108.9 | C39—C41—H41A | 108.8 |
C9—C11—H11B | 108.9 | C42—C41—H41B | 108.8 |
C12—C11—H11B | 108.9 | C39—C41—H41B | 108.8 |
H11A—C11—H11B | 107.8 | H41A—C41—H41B | 107.7 |
C13—C12—C11 | 110.1 (2) | C43—C42—C41 | 109.9 (2) |
C13—C12—H12A | 109.6 | C43—C42—H42A | 109.7 |
C11—C12—H12A | 109.6 | C41—C42—H42A | 109.7 |
C13—C12—H12B | 109.6 | C43—C42—H42B | 109.7 |
C11—C12—H12B | 109.6 | C41—C42—H42B | 109.7 |
H12A—C12—H12B | 108.1 | H42A—C42—H42B | 108.2 |
C17—C13—C12 | 117.4 (2) | C42—C43—C47 | 118.3 (2) |
C17—C13—C14 | 100.4 (2) | C42—C43—C44 | 109.2 (2) |
C12—C13—C14 | 108.9 (2) | C47—C43—C44 | 100.8 (2) |
C17—C13—C18 | 104.4 (2) | C42—C43—C48 | 110.6 (3) |
C12—C13—C18 | 111.6 (2) | C47—C43—C48 | 103.8 (2) |
C14—C13—C18 | 113.8 (2) | C44—C43—C48 | 114.0 (2) |
C8—C14—C15 | 120.5 (2) | C38—C44—C43 | 112.6 (2) |
C8—C14—C13 | 112.4 (2) | C38—C44—C45 | 119.7 (2) |
C15—C14—C13 | 104.5 (2) | C43—C44—C45 | 104.7 (2) |
C8—C14—H14 | 106.2 | C38—C44—H44 | 106.3 |
C15—C14—H14 | 106.2 | C43—C44—H44 | 106.3 |
C13—C14—H14 | 106.2 | C45—C44—H44 | 106.3 |
C14—C15—C16 | 102.8 (2) | C44—C45—C46 | 102.2 (3) |
C14—C15—H15A | 111.2 | C44—C45—H45A | 111.3 |
C16—C15—H15A | 111.2 | C46—C45—H45A | 111.3 |
C14—C15—H15B | 111.2 | C44—C45—H45B | 111.3 |
C16—C15—H15B | 111.2 | C46—C45—H45B | 111.3 |
H15A—C15—H15B | 109.1 | H45A—C45—H45B | 109.2 |
C17—C16—C15 | 104.9 (2) | C47—C46—C45 | 105.7 (3) |
C17—C16—H16A | 110.8 | C47—C46—H46A | 110.6 |
C15—C16—H16A | 110.8 | C45—C46—H46A | 110.6 |
C17—C16—H16B | 110.8 | C47—C46—H46B | 110.6 |
C15—C16—H16B | 110.8 | C45—C46—H46B | 110.6 |
H16A—C16—H16B | 108.8 | H46A—C46—H46B | 108.7 |
O4—C17—C13 | 126.7 (3) | O8—C47—C46 | 124.4 (3) |
O4—C17—C16 | 123.9 (3) | O8—C47—C43 | 126.5 (3) |
C13—C17—C16 | 109.5 (2) | C46—C47—C43 | 109.1 (3) |
C13—C18—H18A | 109.5 | C43—C48—H48A | 109.5 |
C13—C18—H18B | 109.5 | C43—C48—H48B | 109.5 |
H18A—C18—H18B | 109.5 | H48A—C48—H48B | 109.5 |
C13—C18—H18C | 109.5 | C43—C48—H48C | 109.5 |
H18A—C18—H18C | 109.5 | H48A—C48—H48C | 109.5 |
H18B—C18—H18C | 109.5 | H48B—C48—H48C | 109.5 |
C10—C19—H19A | 109.5 | C40—C49—H49A | 109.5 |
C10—C19—H19B | 109.5 | C40—C49—H49B | 109.5 |
H19A—C19—H19B | 109.5 | H49A—C49—H49B | 109.5 |
C10—C19—H19C | 109.5 | C40—C49—H49C | 109.5 |
H19A—C19—H19C | 109.5 | H49A—C49—H49C | 109.5 |
H19B—C19—H19C | 109.5 | H49B—C49—H49C | 109.5 |
O2—C20—O1 | 123.5 (3) | O6—C50—O5 | 124.0 (3) |
O2—C20—C21 | 125.5 (4) | O6—C50—C51 | 125.7 (4) |
O1—C20—C21 | 111.0 (3) | O5—C50—C51 | 110.3 (4) |
C20—C21—H21A | 109.5 | C50—C51—H51A | 109.5 |
C20—C21—H21B | 109.5 | C50—C51—H51B | 109.5 |
H21A—C21—H21B | 109.5 | H51A—C51—H51B | 109.5 |
C20—C21—H21C | 109.5 | C50—C51—H51C | 109.5 |
H21A—C21—H21C | 109.5 | H51A—C51—H51C | 109.5 |
H21B—C21—H21C | 109.5 | H51B—C51—H51C | 109.5 |
C10—C1—C2—C3 | −54.8 (4) | C40—C31—C32—C33 | −53.9 (4) |
C20—O1—C3—C4 | −140.8 (3) | C50—O5—C33—C32 | 92.6 (4) |
C20—O1—C3—C2 | 97.8 (3) | C50—O5—C33—C34 | −145.5 (3) |
C1—C2—C3—O1 | 167.6 (3) | C31—C32—C33—O5 | 167.2 (3) |
C1—C2—C3—C4 | 51.3 (4) | C31—C32—C33—C34 | 50.4 (4) |
O1—C3—C4—C5 | −172.0 (2) | O5—C33—C34—C35 | −172.2 (2) |
C2—C3—C4—C5 | −52.3 (4) | C32—C33—C34—C35 | −51.4 (4) |
C3—C4—C5—C6 | −174.7 (3) | C33—C34—C35—C36 | −174.9 (3) |
C3—C4—C5—C10 | 55.3 (3) | C33—C34—C35—C40 | 54.5 (3) |
C3—C4—C5—Cl1 | −63.3 (3) | C33—C34—C35—Cl2 | −64.0 (3) |
C4—C5—C6—O3 | −56.6 (3) | C34—C35—C36—O7 | −56.2 (3) |
C10—C5—C6—O3 | 72.0 (3) | C40—C35—C36—O7 | 72.9 (3) |
Cl1—C5—C6—O3 | −169.16 (17) | Cl2—C35—C36—O7 | −168.19 (18) |
C4—C5—C6—C7 | −179.0 (2) | C34—C35—C36—C37 | −178.5 (2) |
C10—C5—C6—C7 | −50.3 (3) | C40—C35—C36—C37 | −49.4 (3) |
Cl1—C5—C6—C7 | 68.5 (3) | Cl2—C35—C36—C37 | 69.5 (2) |
O3—C6—C7—C8 | −72.0 (3) | O7—C36—C37—C38 | −73.7 (3) |
C5—C6—C7—C8 | 49.8 (3) | C35—C36—C37—C38 | 48.8 (3) |
C6—C7—C8—C14 | −176.4 (2) | C36—C37—C38—C44 | −176.2 (2) |
C6—C7—C8—C9 | −54.6 (3) | C36—C37—C38—C39 | −54.4 (3) |
C14—C8—C9—C11 | −51.4 (3) | C44—C38—C39—C41 | −50.2 (3) |
C7—C8—C9—C11 | −174.0 (2) | C37—C38—C39—C41 | −173.4 (2) |
C14—C8—C9—C10 | −179.3 (2) | C44—C38—C39—C40 | −178.5 (2) |
C7—C8—C9—C10 | 58.1 (3) | C37—C38—C39—C40 | 58.3 (3) |
C2—C1—C10—C19 | −63.3 (3) | C32—C31—C40—C49 | −63.4 (3) |
C2—C1—C10—C9 | 175.8 (3) | C32—C31—C40—C35 | 55.4 (3) |
C2—C1—C10—C5 | 56.2 (3) | C32—C31—C40—C39 | 175.5 (2) |
C8—C9—C10—C19 | 64.5 (3) | C34—C35—C40—C31 | −55.3 (3) |
C11—C9—C10—C19 | −62.8 (3) | C36—C35—C40—C31 | 175.8 (2) |
C8—C9—C10—C1 | −175.6 (2) | Cl2—C35—C40—C31 | 60.5 (2) |
C11—C9—C10—C1 | 57.1 (3) | C34—C35—C40—C49 | 62.3 (3) |
C8—C9—C10—C5 | −56.5 (3) | C36—C35—C40—C49 | −66.5 (3) |
C11—C9—C10—C5 | 176.2 (2) | Cl2—C35—C40—C49 | 178.1 (2) |
C4—C5—C10—C19 | 61.9 (3) | C34—C35—C40—C39 | −177.5 (2) |
C6—C5—C10—C19 | −66.8 (3) | C36—C35—C40—C39 | 53.6 (3) |
Cl1—C5—C10—C19 | 177.8 (2) | Cl2—C35—C40—C39 | −61.7 (2) |
C4—C5—C10—C1 | −55.9 (3) | C41—C39—C40—C31 | 55.8 (3) |
C6—C5—C10—C1 | 175.4 (2) | C38—C39—C40—C31 | −176.6 (2) |
Cl1—C5—C10—C1 | 60.0 (2) | C41—C39—C40—C49 | −64.2 (3) |
C4—C5—C10—C9 | −177.6 (2) | C38—C39—C40—C49 | 63.4 (3) |
C6—C5—C10—C9 | 53.7 (3) | C41—C39—C40—C35 | 175.6 (2) |
Cl1—C5—C10—C9 | −61.7 (2) | C38—C39—C40—C35 | −56.8 (3) |
C8—C9—C11—C12 | 50.6 (3) | C38—C39—C41—C42 | 49.7 (3) |
C10—C9—C11—C12 | 177.0 (2) | C40—C39—C41—C42 | 176.1 (2) |
C9—C11—C12—C13 | −53.7 (3) | C39—C41—C42—C43 | −53.2 (3) |
C11—C12—C13—C17 | 171.0 (2) | C41—C42—C43—C47 | 172.5 (3) |
C11—C12—C13—C14 | 58.0 (3) | C41—C42—C43—C44 | 58.1 (3) |
C11—C12—C13—C18 | −68.5 (3) | C41—C42—C43—C48 | −68.1 (3) |
C7—C8—C14—C15 | −55.0 (3) | C37—C38—C44—C43 | −179.0 (2) |
C9—C8—C14—C15 | −178.1 (2) | C39—C38—C44—C43 | 57.7 (3) |
C7—C8—C14—C13 | −178.8 (2) | C37—C38—C44—C45 | −55.3 (3) |
C9—C8—C14—C13 | 58.2 (3) | C39—C38—C44—C45 | −178.6 (2) |
C17—C13—C14—C8 | 173.8 (2) | C42—C43—C44—C38 | −62.9 (3) |
C12—C13—C14—C8 | −62.3 (3) | C47—C43—C44—C38 | 171.9 (2) |
C18—C13—C14—C8 | 62.8 (3) | C48—C43—C44—C38 | 61.3 (3) |
C17—C13—C14—C15 | 41.6 (3) | C42—C43—C44—C45 | 165.4 (2) |
C12—C13—C14—C15 | 165.4 (2) | C47—C43—C44—C45 | 40.2 (3) |
C18—C13—C14—C15 | −69.4 (3) | C48—C43—C44—C45 | −70.4 (3) |
C8—C14—C15—C16 | −166.9 (3) | C38—C44—C45—C46 | −167.4 (3) |
C13—C14—C15—C16 | −39.5 (3) | C43—C44—C45—C46 | −40.0 (3) |
C14—C15—C16—C17 | 21.2 (3) | C44—C45—C46—C47 | 23.4 (4) |
C12—C13—C17—O4 | 34.2 (4) | C45—C46—C47—O8 | 178.9 (4) |
C14—C13—C17—O4 | 151.9 (3) | C45—C46—C47—C43 | 1.3 (4) |
C18—C13—C17—O4 | −90.0 (4) | C42—C43—C47—O8 | 38.3 (5) |
C12—C13—C17—C16 | −146.0 (3) | C44—C43—C47—O8 | 157.1 (4) |
C14—C13—C17—C16 | −28.3 (3) | C48—C43—C47—O8 | −84.6 (4) |
C18—C13—C17—C16 | 89.9 (3) | C42—C43—C47—C46 | −144.2 (3) |
C15—C16—C17—O4 | −175.4 (3) | C44—C43—C47—C46 | −25.4 (3) |
C15—C16—C17—C13 | 4.7 (4) | C48—C43—C47—C46 | 92.9 (3) |
C3—O1—C20—O2 | −8.1 (6) | C33—O5—C50—O6 | −6.6 (6) |
C3—O1—C20—C21 | 171.7 (3) | C33—O5—C50—C51 | 172.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3X···O4i | 0.82 | 1.98 | 2.745 (3) | 155 |
O7—H7X···O8ii | 0.80 | 2.03 | 2.791 (3) | 160 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H31ClO4 |
Mr | 382.91 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.1025 (12), 9.9840 (16), 15.552 (3) |
α, β, γ (°) | 100.521 (2), 99.211 (2), 110.470 (2) |
V (Å3) | 985.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.30 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.938, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5701, 4861, 4372 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.090, 1.06 |
No. of reflections | 4861 |
No. of parameters | 476 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.17 |
Absolute structure | Flack (1983), with 983 Friedel pairs |
Absolute structure parameter | 0.00 (5) |
Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3X···O4i | 0.82 | 1.98 | 2.745 (3) | 155.4 |
O7—H7X···O8ii | 0.80 | 2.03 | 2.791 (3) | 159.7 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z. |
Many anabolic steroids have a reduced androgenic side effect (Stanley et al., 1997). Androstane derivatives may be used for oral therapy aginst weight gain after extensive surgery, chronic infections and severe traumata (Alvarez-Ginarte et al., 2005). In continuation of our work on the structure-activity relationship of androstanone derivatives, we present here the structure of the title compound (Fig. 1).
The title compound crystallizes with two molecules in the asymmetric unit. All bond lengths and angles correspond well to those observed in similar steriod structures (Rendle et al., 1974; Xia et al., 2007). Rings A, B and C adopt a chair conformation, while ring D shows an envelope conformation. The hydroxyl group is involved in an intramolecular O—H···O hydrogen bond (Table 1).