The title compound (systematic name: 17-acetyl-16-bromo-17-hydroxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14, 15,16,17-dodecahydro-2
H-cyclopenta[
a]phenanthrene-3,11-dione chloroform solvate), C
21H
27BrO
4·CHCl
3, is an important intermediate in the synthesis of hormone pharmaceuticals. The asymmetric unit consists of one steroid and one chloroform molecule. The crystal structure is predominantly stabilized by strong intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 608353
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.091
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.85 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion Cl Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C22
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.09
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.86
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 43.00 Perc.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Cl1 .. 3.57 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.30 Deg.
O1 -C3 -O1' 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.40 Deg.
CL1' -C22 -CL1 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.00 Deg.
CL3' -C22 -CL3 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.50 Deg.
CL2' -C22 -CL2 1.555 1.555 1.555
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.50
From the CIF: _reflns_number_total 4527
Count of symmetry unique reflns 2582
Completeness (_total/calc) 175.33%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1945
Fraction of Friedel pairs measured 0.753
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
17-acetyl-16-bromo-17-hydroxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14,
15,16,17-dodecahydro-2
H-cyclopenta[
a]phenanthrene-3,11-dione
chloroform solvate
top
Crystal data top
C21H27BrO4·CHCl3 | Dx = 1.480 Mg m−3 |
Mr = 542.70 | Melting point: 472.2 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 16366 reflections |
a = 10.443 (2) Å | θ = 3.3–27.5° |
b = 12.324 (3) Å | µ = 2.04 mm−1 |
c = 18.927 (4) Å | T = 296 K |
V = 2435.9 (9) Å3 | Plate, colorless |
Z = 4 | 0.23 × 0.18 × 0.05 mm |
F(000) = 1112 | |
Data collection top
Rigaku R-AXIS RAPID IP area-detector diffractometer | 4527 independent reflections |
Radiation source: fine-focus sealed tube | 3310 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
φ? ω? scans | θmax = 25.5°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.648, Tmax = 0.901 | k = −14→14 |
20190 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0364P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.091 | (Δ/σ)max = 0.001 |
S = 0.95 | Δρmax = 0.27 e Å−3 |
4527 reflections | Δρmin = −0.30 e Å−3 |
309 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.0070 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1972 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (1) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Br1 | 0.01979 (5) | 0.98165 (4) | 0.191311 (19) | 0.07040 (19) | |
Cl1 | −0.0126 (7) | 0.4280 (8) | 0.1234 (4) | 0.136 (3) | 0.488 (9) |
Cl2 | 0.1017 (4) | 0.2558 (4) | 0.1122 (2) | 0.0847 (15) | 0.488 (9) |
Cl3 | −0.1541 (6) | 0.2742 (9) | 0.0629 (6) | 0.115 (3) | 0.488 (9) |
Cl1' | −0.0059 (6) | 0.4614 (3) | 0.0857 (4) | 0.0987 (18) | 0.512 (9) |
Cl2' | 0.1164 (6) | 0.2499 (5) | 0.0692 (9) | 0.256 (5) | 0.512 (9) |
Cl3' | −0.1411 (9) | 0.2707 (9) | 0.0350 (6) | 0.152 (4) | 0.512 (9) |
C1 | 0.0966 (4) | 0.8674 (4) | −0.26704 (17) | 0.0603 (12) | |
H1A | 0.1858 | 0.8491 | −0.2593 | 0.072* | |
H1B | 0.0463 | 0.8021 | −0.2599 | 0.072* | |
C2 | 0.0797 (4) | 0.9057 (5) | −0.34310 (19) | 0.0697 (14) | |
H2A | 0.1372 | 0.9660 | −0.3522 | 0.084* | |
H2B | 0.1018 | 0.8473 | −0.3752 | 0.084* | |
C3 | −0.0539 (5) | 0.9403 (6) | −0.3562 (2) | 0.108 (2) | |
C4 | −0.1211 (4) | 0.9909 (5) | −0.29772 (19) | 0.0863 (16) | |
H4A | −0.2028 | 1.0181 | −0.3060 | 0.104* | |
C5 | −0.0729 (3) | 1.0008 (4) | −0.23266 (17) | 0.0535 (11) | |
C6 | −0.1443 (4) | 1.0646 (4) | −0.17798 (19) | 0.0642 (12) | |
H6A | −0.2301 | 1.0791 | −0.1951 | 0.077* | |
H6B | −0.1018 | 1.1339 | −0.1713 | 0.077* | |
C7 | −0.1531 (3) | 1.0065 (3) | −0.10701 (16) | 0.0485 (9) | |
H7A | −0.1894 | 1.0555 | −0.0722 | 0.058* | |
H7B | −0.2100 | 0.9447 | −0.1114 | 0.058* | |
C8 | −0.0225 (3) | 0.9679 (3) | −0.08164 (15) | 0.0370 (7) | |
H8A | 0.0321 | 1.0314 | −0.0736 | 0.044* | |
C9 | 0.0406 (3) | 0.8955 (3) | −0.13884 (15) | 0.0348 (8) | |
H9A | −0.0210 | 0.8369 | −0.1472 | 0.042* | |
C10 | 0.0554 (3) | 0.9534 (3) | −0.21207 (16) | 0.0433 (9) | |
C11 | 0.1600 (3) | 0.8392 (3) | −0.11102 (15) | 0.0399 (8) | |
C12 | 0.1470 (3) | 0.7815 (3) | −0.04081 (15) | 0.0373 (8) | |
H12A | 0.2296 | 0.7537 | −0.0259 | 0.045* | |
H12B | 0.0884 | 0.7208 | −0.0454 | 0.045* | |
C13 | 0.0958 (3) | 0.8622 (3) | 0.01417 (15) | 0.0333 (8) | |
C14 | −0.0329 (3) | 0.9039 (3) | −0.01293 (14) | 0.0331 (7) | |
H14A | −0.0865 | 0.8403 | −0.0225 | 0.040* | |
C15 | −0.0904 (4) | 0.9619 (3) | 0.05090 (16) | 0.0460 (9) | |
H15A | −0.1830 | 0.9644 | 0.0478 | 0.055* | |
H15B | −0.0576 | 1.0353 | 0.0549 | 0.055* | |
C16 | −0.0468 (4) | 0.8918 (3) | 0.11386 (15) | 0.0428 (9) | |
H16A | −0.1213 | 0.8518 | 0.1315 | 0.051* | |
C17 | 0.0509 (3) | 0.8087 (3) | 0.08501 (15) | 0.0357 (8) | |
C18 | 0.1547 (4) | 0.7726 (3) | 0.13801 (16) | 0.0418 (9) | |
C19 | 0.1094 (4) | 0.7143 (4) | 0.20317 (18) | 0.0636 (12) | |
H19A | 0.1816 | 0.6962 | 0.2322 | 0.095* | |
H19B | 0.0654 | 0.6490 | 0.1897 | 0.095* | |
H19C | 0.0521 | 0.7603 | 0.2292 | 0.095* | |
C20 | 0.1536 (4) | 1.0461 (4) | −0.2089 (2) | 0.0685 (13) | |
H20A | 0.1271 | 1.0983 | −0.1743 | 0.103* | |
H20B | 0.1592 | 1.0804 | −0.2543 | 0.103* | |
H20C | 0.2359 | 1.0174 | −0.1961 | 0.103* | |
C21 | 0.1945 (4) | 0.9521 (3) | 0.02571 (17) | 0.0449 (9) | |
H21A | 0.2193 | 0.9819 | −0.0191 | 0.067* | |
H21B | 0.2684 | 0.9226 | 0.0490 | 0.067* | |
H21C | 0.1578 | 1.0082 | 0.0545 | 0.067* | |
C22 | −0.0018 (4) | 0.3354 (3) | 0.0564 (2) | 0.0810 (15) | |
H22A | 0.0317 | 0.3501 | 0.0090 | 0.097* | |
O1 | −0.0875 (16) | 0.9716 (15) | −0.4182 (6) | 0.127 (6) | 0.488 (9) |
O1' | −0.1131 (13) | 0.9001 (12) | −0.4106 (6) | 0.098 (4) | 0.512 (9) |
O2 | 0.2625 (2) | 0.8404 (2) | −0.14253 (11) | 0.0547 (7) | |
O3 | −0.0139 (2) | 0.71145 (18) | 0.06626 (10) | 0.0445 (6) | |
H3A | −0.0772 | 0.7040 | 0.0914 | 0.067* | |
O4 | 0.2681 (3) | 0.7823 (2) | 0.12630 (13) | 0.0594 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0798 (3) | 0.0796 (3) | 0.0518 (2) | 0.0131 (2) | −0.0065 (2) | −0.0256 (2) |
Cl1 | 0.105 (4) | 0.164 (6) | 0.138 (4) | −0.014 (4) | 0.025 (4) | −0.080 (4) |
Cl2 | 0.067 (3) | 0.061 (2) | 0.126 (3) | 0.0094 (17) | −0.024 (2) | 0.0188 (18) |
Cl3 | 0.055 (3) | 0.095 (4) | 0.196 (8) | −0.012 (2) | −0.021 (3) | −0.054 (5) |
Cl1' | 0.080 (3) | 0.0490 (18) | 0.168 (4) | 0.0156 (16) | −0.026 (3) | −0.020 (2) |
Cl2' | 0.094 (4) | 0.089 (4) | 0.585 (16) | 0.003 (3) | 0.108 (7) | −0.081 (7) |
Cl3' | 0.180 (7) | 0.082 (4) | 0.196 (8) | −0.016 (4) | −0.098 (6) | −0.018 (4) |
C1 | 0.054 (3) | 0.090 (3) | 0.0372 (18) | 0.013 (2) | 0.0035 (17) | 0.002 (2) |
C2 | 0.049 (3) | 0.116 (4) | 0.044 (2) | 0.018 (3) | 0.0055 (18) | 0.012 (2) |
C3 | 0.067 (4) | 0.215 (7) | 0.041 (2) | 0.053 (4) | −0.003 (2) | 0.007 (3) |
C4 | 0.053 (3) | 0.153 (5) | 0.054 (2) | 0.035 (3) | −0.0008 (18) | 0.018 (3) |
C5 | 0.034 (2) | 0.078 (3) | 0.0479 (18) | 0.009 (2) | 0.0030 (14) | 0.021 (2) |
C6 | 0.053 (3) | 0.075 (3) | 0.065 (3) | 0.024 (2) | −0.001 (2) | 0.017 (2) |
C7 | 0.040 (2) | 0.058 (3) | 0.0477 (17) | 0.017 (2) | 0.0009 (14) | 0.0023 (18) |
C8 | 0.0284 (19) | 0.0391 (19) | 0.0436 (15) | 0.0050 (17) | −0.0011 (13) | 0.0017 (14) |
C9 | 0.026 (2) | 0.042 (2) | 0.0367 (15) | 0.0004 (16) | −0.0004 (13) | 0.0059 (13) |
C10 | 0.030 (2) | 0.057 (3) | 0.0423 (17) | 0.0057 (17) | −0.0001 (13) | 0.0133 (15) |
C11 | 0.037 (2) | 0.047 (2) | 0.0353 (16) | 0.0077 (18) | −0.0013 (14) | −0.0017 (15) |
C12 | 0.031 (2) | 0.040 (2) | 0.0402 (16) | 0.0082 (17) | 0.0026 (14) | 0.0040 (15) |
C13 | 0.0287 (19) | 0.037 (2) | 0.0344 (16) | 0.0018 (16) | 0.0022 (13) | −0.0008 (13) |
C14 | 0.0246 (18) | 0.0366 (19) | 0.0382 (15) | 0.0016 (17) | −0.0001 (13) | 0.0001 (13) |
C15 | 0.040 (2) | 0.048 (2) | 0.0498 (18) | 0.0102 (19) | 0.0047 (15) | −0.0020 (17) |
C16 | 0.037 (2) | 0.052 (2) | 0.0399 (17) | −0.0026 (18) | 0.0036 (15) | −0.0040 (15) |
C17 | 0.030 (2) | 0.040 (2) | 0.0371 (15) | −0.0016 (16) | 0.0011 (13) | 0.0031 (14) |
C18 | 0.040 (3) | 0.046 (2) | 0.0393 (17) | 0.0015 (18) | 0.0022 (16) | 0.0008 (16) |
C19 | 0.062 (3) | 0.084 (3) | 0.044 (2) | 0.004 (2) | 0.0071 (18) | 0.019 (2) |
C20 | 0.058 (3) | 0.082 (4) | 0.065 (3) | −0.015 (2) | −0.003 (2) | 0.026 (2) |
C21 | 0.037 (2) | 0.048 (2) | 0.0495 (18) | −0.0101 (18) | −0.0036 (15) | 0.0058 (16) |
C22 | 0.095 (5) | 0.071 (3) | 0.077 (3) | −0.010 (3) | 0.007 (3) | −0.008 (2) |
O1 | 0.107 (11) | 0.234 (18) | 0.040 (4) | 0.080 (12) | −0.011 (5) | 0.020 (9) |
O1' | 0.053 (5) | 0.190 (14) | 0.050 (5) | 0.002 (8) | −0.014 (4) | 0.004 (7) |
O2 | 0.0292 (15) | 0.090 (2) | 0.0452 (13) | 0.0170 (14) | 0.0075 (10) | 0.0147 (13) |
O3 | 0.0430 (17) | 0.0440 (14) | 0.0466 (12) | −0.0101 (12) | 0.0107 (11) | 0.0007 (9) |
O4 | 0.0338 (17) | 0.083 (2) | 0.0613 (14) | 0.0054 (15) | −0.0018 (13) | 0.0167 (14) |
Geometric parameters (Å, º) top
Br1—C16 | 1.964 (3) | C9—H9A | 0.9800 |
Cl1—C22 | 1.709 (6) | C10—C20 | 1.536 (5) |
Cl2—C22 | 1.802 (5) | C11—O2 | 1.225 (4) |
Cl3—C22 | 1.765 (7) | C11—C12 | 1.514 (4) |
Cl1'—C22 | 1.650 (5) | C12—C13 | 1.536 (4) |
Cl2'—C22 | 1.641 (7) | C12—H12A | 0.9700 |
Cl3'—C22 | 1.708 (8) | C12—H12B | 0.9700 |
C1—C2 | 1.525 (5) | C13—C14 | 1.528 (4) |
C1—C10 | 1.546 (5) | C13—C21 | 1.528 (5) |
C1—H1A | 0.9700 | C13—C17 | 1.566 (4) |
C1—H1B | 0.9700 | C14—C15 | 1.527 (4) |
C2—C3 | 1.480 (6) | C14—H14A | 0.9800 |
C2—H2A | 0.9700 | C15—C16 | 1.540 (5) |
C2—H2B | 0.9700 | C15—H15A | 0.9700 |
C3—O1 | 1.285 (12) | C15—H15B | 0.9700 |
C3—O1' | 1.299 (14) | C16—C17 | 1.545 (5) |
C3—C4 | 1.452 (6) | C16—H16A | 0.9800 |
C4—C5 | 1.336 (5) | C17—O3 | 1.421 (4) |
C4—H4A | 0.9300 | C17—C18 | 1.542 (5) |
C5—C6 | 1.499 (5) | C18—O4 | 1.211 (4) |
C5—C10 | 1.512 (5) | C18—C19 | 1.504 (5) |
C6—C7 | 1.525 (5) | C19—H19A | 0.9600 |
C6—H6A | 0.9700 | C19—H19B | 0.9600 |
C6—H6B | 0.9700 | C19—H19C | 0.9600 |
C7—C8 | 1.522 (4) | C20—H20A | 0.9600 |
C7—H7A | 0.9700 | C20—H20B | 0.9600 |
C7—H7B | 0.9700 | C20—H20C | 0.9600 |
C8—C14 | 1.525 (4) | C21—H21A | 0.9600 |
C8—C9 | 1.550 (4) | C21—H21B | 0.9600 |
C8—H8A | 0.9800 | C21—H21C | 0.9600 |
C9—C11 | 1.521 (5) | C22—H22A | 0.9800 |
C9—C10 | 1.567 (4) | O3—H3A | 0.8200 |
| | | |
C2—C1—C10 | 113.0 (4) | C12—C13—C17 | 114.3 (3) |
C2—C1—H1A | 109.0 | C8—C14—C15 | 117.4 (3) |
C10—C1—H1A | 109.0 | C8—C14—C13 | 113.4 (3) |
C2—C1—H1B | 109.0 | C15—C14—C13 | 103.7 (2) |
C10—C1—H1B | 109.0 | C8—C14—H14A | 107.2 |
H1A—C1—H1B | 107.8 | C15—C14—H14A | 107.2 |
C3—C2—C1 | 110.9 (3) | C13—C14—H14A | 107.2 |
C3—C2—H2A | 109.5 | C14—C15—C16 | 103.5 (3) |
C1—C2—H2A | 109.5 | C14—C15—H15A | 111.1 |
C3—C2—H2B | 109.5 | C16—C15—H15A | 111.1 |
C1—C2—H2B | 109.5 | C14—C15—H15B | 111.1 |
H2A—C2—H2B | 108.1 | C16—C15—H15B | 111.1 |
O1—C3—O1' | 42.3 (8) | H15A—C15—H15B | 109.0 |
O1—C3—C4 | 115.8 (8) | C15—C16—C17 | 107.1 (2) |
O1'—C3—C4 | 122.5 (8) | C15—C16—Br1 | 111.4 (2) |
O1—C3—C2 | 119.8 (8) | C17—C16—Br1 | 113.8 (2) |
O1'—C3—C2 | 118.2 (8) | C15—C16—H16A | 108.1 |
C4—C3—C2 | 116.9 (4) | C17—C16—H16A | 108.1 |
C5—C4—C3 | 124.0 (4) | Br1—C16—H16A | 108.1 |
C5—C4—H4A | 118.0 | O3—C17—C18 | 104.7 (3) |
C3—C4—H4A | 118.0 | O3—C17—C16 | 109.5 (3) |
C4—C5—C6 | 119.8 (4) | C18—C17—C16 | 115.2 (3) |
C4—C5—C10 | 122.5 (4) | O3—C17—C13 | 106.5 (2) |
C6—C5—C10 | 117.7 (3) | C18—C17—C13 | 117.9 (3) |
C5—C6—C7 | 113.1 (3) | C16—C17—C13 | 102.8 (3) |
C5—C6—H6A | 109.0 | O4—C18—C19 | 120.3 (3) |
C7—C6—H6A | 109.0 | O4—C18—C17 | 122.7 (3) |
C5—C6—H6B | 109.0 | C19—C18—C17 | 116.7 (3) |
C7—C6—H6B | 109.0 | C18—C19—H19A | 109.5 |
H6A—C6—H6B | 107.8 | C18—C19—H19B | 109.5 |
C8—C7—C6 | 111.7 (3) | H19A—C19—H19B | 109.5 |
C8—C7—H7A | 109.3 | C18—C19—H19C | 109.5 |
C6—C7—H7A | 109.3 | H19A—C19—H19C | 109.5 |
C8—C7—H7B | 109.3 | H19B—C19—H19C | 109.5 |
C6—C7—H7B | 109.3 | C10—C20—H20A | 109.5 |
H7A—C7—H7B | 107.9 | C10—C20—H20B | 109.5 |
C7—C8—C14 | 111.6 (3) | H20A—C20—H20B | 109.5 |
C7—C8—C9 | 109.9 (2) | C10—C20—H20C | 109.5 |
C14—C8—C9 | 109.1 (3) | H20A—C20—H20C | 109.5 |
C7—C8—H8A | 108.7 | H20B—C20—H20C | 109.5 |
C14—C8—H8A | 108.7 | C13—C21—H21A | 109.5 |
C9—C8—H8A | 108.7 | C13—C21—H21B | 109.5 |
C11—C9—C8 | 111.7 (2) | H21A—C21—H21B | 109.5 |
C11—C9—C10 | 115.7 (3) | C13—C21—H21C | 109.5 |
C8—C9—C10 | 113.4 (3) | H21A—C21—H21C | 109.5 |
C11—C9—H9A | 104.9 | H21B—C21—H21C | 109.5 |
C8—C9—H9A | 104.9 | Cl2'—C22—Cl1' | 125.1 (5) |
C10—C9—H9A | 104.9 | Cl2'—C22—Cl3' | 112.1 (5) |
C5—C10—C20 | 108.3 (3) | Cl1'—C22—Cl3' | 119.8 (5) |
C5—C10—C1 | 109.7 (3) | Cl2'—C22—Cl1 | 111.7 (8) |
C20—C10—C1 | 110.5 (3) | Cl1'—C22—Cl1 | 28.4 (2) |
C5—C10—C9 | 108.4 (3) | Cl3'—C22—Cl1 | 115.5 (5) |
C20—C10—C9 | 111.7 (3) | Cl2'—C22—Cl3 | 113.2 (5) |
C1—C10—C9 | 108.1 (3) | Cl1'—C22—Cl3 | 110.8 (5) |
O2—C11—C12 | 120.8 (3) | Cl3'—C22—Cl3 | 18.0 (6) |
O2—C11—C9 | 122.8 (3) | Cl1—C22—Cl3 | 100.0 (4) |
C12—C11—C9 | 116.4 (3) | Cl2'—C22—Cl2 | 27.5 (5) |
C11—C12—C13 | 108.8 (3) | Cl1'—C22—Cl2 | 109.4 (3) |
C11—C12—H12A | 109.9 | Cl3'—C22—Cl2 | 113.3 (5) |
C13—C12—H12A | 109.9 | Cl1—C22—Cl2 | 88.2 (5) |
C11—C12—H12B | 109.9 | Cl3—C22—Cl2 | 105.5 (5) |
C13—C12—H12B | 109.9 | Cl2'—C22—H22A | 89.2 |
H12A—C12—H12B | 108.3 | Cl1'—C22—H22A | 98.2 |
C14—C13—C21 | 113.4 (3) | Cl3'—C22—H22A | 100.0 |
C14—C13—C12 | 107.2 (3) | Cl1—C22—H22A | 125.4 |
C21—C13—C12 | 109.4 (3) | Cl3—C22—H22A | 117.7 |
C14—C13—C17 | 99.5 (2) | Cl2—C22—H22A | 115.0 |
C21—C13—C17 | 112.6 (2) | C17—O3—H3A | 109.5 |
| | | |
C10—C1—C2—C3 | −55.6 (6) | C11—C12—C13—C14 | 58.8 (4) |
C1—C2—C3—O1 | −177.5 (12) | C11—C12—C13—C21 | −64.6 (3) |
C1—C2—C3—O1' | −128.8 (8) | C11—C12—C13—C17 | 168.0 (3) |
C1—C2—C3—C4 | 33.9 (8) | C7—C8—C14—C15 | −59.6 (4) |
O1—C3—C4—C5 | −154.7 (11) | C9—C8—C14—C15 | 178.8 (3) |
O1'—C3—C4—C5 | 157.1 (9) | C7—C8—C14—C13 | 179.3 (3) |
C2—C3—C4—C5 | −4.8 (10) | C9—C8—C14—C13 | 57.6 (4) |
C3—C4—C5—C6 | 173.6 (6) | C21—C13—C14—C8 | 56.9 (4) |
C3—C4—C5—C10 | −3.8 (8) | C12—C13—C14—C8 | −63.9 (4) |
C4—C5—C6—C7 | 133.7 (4) | C17—C13—C14—C8 | 176.8 (3) |
C10—C5—C6—C7 | −48.8 (6) | C21—C13—C14—C15 | −71.6 (3) |
C5—C6—C7—C8 | 51.0 (5) | C12—C13—C14—C15 | 167.6 (3) |
C6—C7—C8—C14 | −176.5 (3) | C17—C13—C14—C15 | 48.3 (3) |
C6—C7—C8—C9 | −55.3 (4) | C8—C14—C15—C16 | −162.1 (3) |
C7—C8—C9—C11 | −170.0 (3) | C13—C14—C15—C16 | −36.1 (3) |
C14—C8—C9—C11 | −47.4 (4) | C14—C15—C16—C17 | 9.1 (4) |
C7—C8—C9—C10 | 57.1 (4) | C14—C15—C16—Br1 | 134.1 (3) |
C14—C8—C9—C10 | 179.7 (3) | C15—C16—C17—O3 | −92.6 (3) |
C4—C5—C10—C20 | 103.5 (5) | Br1—C16—C17—O3 | 143.8 (2) |
C6—C5—C10—C20 | −74.0 (4) | C15—C16—C17—C18 | 149.8 (3) |
C4—C5—C10—C1 | −17.3 (5) | Br1—C16—C17—C18 | 26.2 (4) |
C6—C5—C10—C1 | 165.3 (4) | C15—C16—C17—C13 | 20.3 (4) |
C4—C5—C10—C9 | −135.1 (4) | Br1—C16—C17—C13 | −103.3 (2) |
C6—C5—C10—C9 | 47.5 (5) | C14—C13—C17—O3 | 73.7 (3) |
C2—C1—C10—C5 | 46.5 (4) | C21—C13—C17—O3 | −165.9 (3) |
C2—C1—C10—C20 | −72.9 (4) | C12—C13—C17—O3 | −40.2 (4) |
C2—C1—C10—C9 | 164.6 (3) | C14—C13—C17—C18 | −169.2 (3) |
C11—C9—C10—C5 | 177.8 (3) | C21—C13—C17—C18 | −48.8 (4) |
C8—C9—C10—C5 | −51.3 (4) | C12—C13—C17—C18 | 76.9 (4) |
C11—C9—C10—C20 | −62.8 (4) | C14—C13—C17—C16 | −41.4 (3) |
C8—C9—C10—C20 | 68.1 (4) | C21—C13—C17—C16 | 79.1 (3) |
C11—C9—C10—C1 | 58.9 (4) | C12—C13—C17—C16 | −155.3 (3) |
C8—C9—C10—C1 | −170.1 (3) | O3—C17—C18—O4 | 116.7 (4) |
C8—C9—C11—O2 | −130.2 (4) | C16—C17—C18—O4 | −123.1 (4) |
C10—C9—C11—O2 | 1.5 (5) | C13—C17—C18—O4 | −1.4 (5) |
C8—C9—C11—C12 | 49.1 (4) | O3—C17—C18—C19 | −57.6 (4) |
C10—C9—C11—C12 | −179.2 (3) | C16—C17—C18—C19 | 62.6 (4) |
O2—C11—C12—C13 | 124.5 (4) | C13—C17—C18—C19 | −175.7 (3) |
C9—C11—C12—C13 | −54.8 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2i | 0.82 | 2.01 | 2.819 (3) | 169 |
Symmetry code: (i) x−1/2, −y+3/2, −z. |