16β-Bromo-17α-hydroxy-pregn-4-ene-3,11,20-trione, C
21H
27BrO
4·CH
4O, is an important intermediate in the synthesis of hormone pharmaceuticals. The crystal structure of its methanol solvate is reported in this paper. The structure is stabilized by strong intermolecular O—H
O hydrogen bonds.
Supporting information
CCDC reference: 621336
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.081
- Data-to-parameter ratio = 19.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 4815
Count of symmetry unique reflns 2750
Completeness (_total/calc) 175.09%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2065
Fraction of Friedel pairs measured 0.751
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
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 C16 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
10 ALERT level G = General alerts; check
9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: RAPID-AUTO (Rigaku, date); 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: SHELXTL97 (Bruker, 1998); software used to prepare material for publication: SHELXTL97.
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
top
Crystal data top
C21H27BrO4·CH4O | Dx = 1.437 Mg m−3 |
Mr = 455.38 | Melting point: 472.2 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 16668 reflections |
a = 8.6030 (17) Å | θ = 3.1–27.5° |
b = 12.235 (2) Å | µ = 1.98 mm−1 |
c = 20.001 (4) Å | T = 293 K |
V = 2105.3 (7) Å3 | Block, colorless |
Z = 4 | 0.24 × 0.24 × 0.22 mm |
F(000) = 952 | |
Data collection top
Rigaku R-axis rapid IP area detector diffractometer | 4815 independent reflections |
Radiation source: rotating anode | 4133 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→11 |
Tmin = 0.648, Tmax = 0.670 | k = −15→15 |
20576 measured reflections | l = −25→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.030P)2 + 0.8713P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
4815 reflections | Δρmax = 0.30 e Å−3 |
254 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2065 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.016 (8) |
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 | |
Br1 | 0.17182 (3) | 0.32344 (3) | 0.886250 (16) | 0.04964 (10) | |
O1 | 1.2893 (2) | −0.1664 (2) | 0.95469 (10) | 0.0567 (6) | |
O2 | 0.8996 (3) | 0.16515 (19) | 0.76128 (9) | 0.0508 (5) | |
O3 | 0.6057 (2) | 0.39963 (17) | 0.94458 (9) | 0.0406 (5) | |
H3A | 0.6818 | 0.4323 | 0.9302 | 0.061* | |
O4 | 0.5169 (3) | 0.46773 (18) | 0.78963 (10) | 0.0564 (6) | |
C1 | 1.0929 (3) | 0.0061 (2) | 0.84126 (14) | 0.0394 (6) | |
H1A | 1.1083 | 0.0354 | 0.7967 | 0.047* | |
H1B | 1.1206 | 0.0628 | 0.8730 | 0.047* | |
C2 | 1.2014 (3) | −0.0911 (3) | 0.85114 (14) | 0.0415 (7) | |
H2A | 1.1789 | −0.1469 | 0.8181 | 0.050* | |
H2B | 1.3084 | −0.0680 | 0.8454 | 0.050* | |
C3 | 1.1792 (4) | −0.1367 (2) | 0.91985 (14) | 0.0395 (6) | |
C4 | 1.0190 (4) | −0.1463 (2) | 0.94176 (14) | 0.0390 (6) | |
H4A | 0.9981 | −0.1869 | 0.9800 | 0.047* | |
C5 | 0.8990 (3) | −0.0993 (2) | 0.90947 (13) | 0.0326 (6) | |
C6 | 0.7345 (4) | −0.1205 (2) | 0.93104 (16) | 0.0433 (7) | |
H6A | 0.7352 | −0.1660 | 0.9707 | 0.052* | |
H6B | 0.6807 | −0.1601 | 0.8960 | 0.052* | |
C7 | 0.6467 (3) | −0.0149 (2) | 0.94597 (13) | 0.0378 (6) | |
H7A | 0.6891 | 0.0183 | 0.9860 | 0.045* | |
H7B | 0.5383 | −0.0318 | 0.9544 | 0.045* | |
C8 | 0.6575 (3) | 0.06665 (19) | 0.88804 (13) | 0.0302 (5) | |
H8A | 0.5995 | 0.0379 | 0.8497 | 0.036* | |
C9 | 0.8288 (3) | 0.08452 (19) | 0.86739 (11) | 0.0277 (5) | |
H9A | 0.8798 | 0.1136 | 0.9074 | 0.033* | |
C10 | 0.9197 (3) | −0.0223 (2) | 0.85024 (12) | 0.0314 (5) | |
C11 | 0.8402 (3) | 0.1760 (2) | 0.81553 (11) | 0.0331 (5) | |
C12 | 0.7674 (3) | 0.2833 (2) | 0.83639 (14) | 0.0338 (6) | |
H12A | 0.7764 | 0.3360 | 0.8004 | 0.041* | |
H12B | 0.8213 | 0.3122 | 0.8751 | 0.041* | |
C13 | 0.5962 (3) | 0.2649 (2) | 0.85324 (12) | 0.0290 (5) | |
C14 | 0.5886 (3) | 0.1770 (2) | 0.90832 (11) | 0.0294 (5) | |
H14A | 0.6508 | 0.2040 | 0.9459 | 0.035* | |
C15 | 0.4187 (3) | 0.1801 (3) | 0.93067 (14) | 0.0399 (6) | |
H15A | 0.4074 | 0.1528 | 0.9759 | 0.048* | |
H15B | 0.3535 | 0.1373 | 0.9010 | 0.048* | |
C16 | 0.3776 (3) | 0.3020 (2) | 0.92675 (13) | 0.0343 (6) | |
H16A | 0.3738 | 0.3306 | 0.9725 | 0.041* | |
C17 | 0.5141 (3) | 0.3603 (2) | 0.88960 (13) | 0.0299 (5) | |
C18 | 0.4737 (3) | 0.4614 (2) | 0.84703 (14) | 0.0381 (6) | |
C19 | 0.3929 (4) | 0.5556 (3) | 0.88012 (18) | 0.0547 (8) | |
H19A | 0.3755 | 0.6125 | 0.8479 | 0.082* | |
H19B | 0.4564 | 0.5831 | 0.9158 | 0.082* | |
H19C | 0.2950 | 0.5315 | 0.8978 | 0.082* | |
C21 | 0.5086 (4) | 0.2293 (2) | 0.78981 (13) | 0.0398 (6) | |
H21A | 0.5154 | 0.2860 | 0.7567 | 0.060* | |
H21B | 0.4014 | 0.2162 | 0.8005 | 0.060* | |
H21C | 0.5543 | 0.1635 | 0.7726 | 0.060* | |
C20 | 0.8577 (4) | −0.0795 (2) | 0.78676 (14) | 0.0461 (7) | |
H20A | 0.7497 | −0.0969 | 0.7927 | 0.069* | |
H20B | 0.9154 | −0.1455 | 0.7791 | 0.069* | |
H20C | 0.8694 | −0.0316 | 0.7491 | 0.069* | |
O5 | 0.7952 (5) | 0.5673 (3) | 0.91790 (14) | 0.1060 (13) | |
H5 | 0.8191 | 0.6037 | 0.9507 | 0.159* | |
C22 | 0.8894 (6) | 0.5940 (4) | 0.8658 (2) | 0.0909 (16) | |
H22A | 0.9961 | 0.5884 | 0.8795 | 0.109* | |
H22B | 0.8680 | 0.6676 | 0.8519 | 0.109* | |
H22C | 0.8707 | 0.5449 | 0.8292 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.03185 (13) | 0.05303 (18) | 0.06404 (18) | 0.00428 (14) | −0.00713 (14) | 0.00416 (16) |
O1 | 0.0457 (12) | 0.0657 (15) | 0.0588 (12) | 0.0091 (12) | −0.0137 (10) | 0.0129 (12) |
O2 | 0.0656 (13) | 0.0484 (13) | 0.0383 (10) | 0.0138 (11) | 0.0168 (10) | 0.0115 (9) |
O3 | 0.0453 (11) | 0.0410 (12) | 0.0354 (10) | −0.0077 (9) | −0.0076 (9) | −0.0059 (8) |
O4 | 0.0836 (17) | 0.0447 (13) | 0.0409 (11) | 0.0121 (13) | 0.0079 (12) | 0.0113 (10) |
C1 | 0.0366 (15) | 0.0422 (17) | 0.0393 (14) | 0.0056 (12) | 0.0043 (12) | 0.0078 (12) |
C2 | 0.0345 (15) | 0.0491 (18) | 0.0409 (14) | 0.0082 (12) | 0.0002 (12) | −0.0012 (12) |
C3 | 0.0439 (15) | 0.0314 (14) | 0.0431 (14) | 0.0049 (13) | −0.0044 (14) | −0.0011 (11) |
C4 | 0.0458 (16) | 0.0334 (16) | 0.0378 (14) | 0.0039 (12) | 0.0002 (13) | 0.0056 (11) |
C5 | 0.0383 (14) | 0.0240 (14) | 0.0355 (13) | −0.0016 (11) | −0.0024 (11) | 0.0004 (10) |
C6 | 0.0431 (16) | 0.0276 (15) | 0.0593 (18) | −0.0030 (12) | 0.0016 (14) | 0.0113 (13) |
C7 | 0.0336 (15) | 0.0342 (15) | 0.0455 (14) | −0.0009 (11) | 0.0037 (12) | 0.0100 (11) |
C8 | 0.0295 (12) | 0.0268 (12) | 0.0345 (12) | −0.0026 (10) | −0.0020 (12) | 0.0055 (10) |
C9 | 0.0292 (11) | 0.0272 (12) | 0.0267 (11) | −0.0019 (11) | −0.0016 (11) | 0.0015 (8) |
C10 | 0.0344 (14) | 0.0291 (14) | 0.0306 (12) | 0.0019 (11) | −0.0021 (11) | 0.0001 (10) |
C11 | 0.0289 (12) | 0.0351 (13) | 0.0354 (12) | 0.0000 (13) | 0.0027 (10) | 0.0073 (11) |
C12 | 0.0379 (14) | 0.0279 (14) | 0.0357 (13) | −0.0029 (11) | 0.0020 (12) | 0.0060 (10) |
C13 | 0.0312 (13) | 0.0278 (14) | 0.0279 (12) | −0.0027 (10) | −0.0011 (11) | 0.0020 (10) |
C14 | 0.0270 (11) | 0.0310 (13) | 0.0302 (11) | −0.0014 (11) | −0.0001 (9) | 0.0034 (11) |
C15 | 0.0284 (13) | 0.0394 (16) | 0.0518 (15) | −0.0006 (13) | 0.0048 (11) | 0.0096 (14) |
C16 | 0.0273 (12) | 0.0420 (17) | 0.0336 (13) | 0.0024 (11) | 0.0004 (10) | 0.0026 (11) |
C17 | 0.0299 (12) | 0.0336 (13) | 0.0262 (11) | −0.0009 (10) | −0.0036 (11) | −0.0002 (10) |
C18 | 0.0398 (15) | 0.0324 (15) | 0.0420 (15) | −0.0010 (12) | −0.0045 (13) | 0.0027 (12) |
C19 | 0.063 (2) | 0.0386 (17) | 0.0625 (19) | 0.0124 (14) | 0.0121 (18) | 0.0020 (15) |
C21 | 0.0444 (16) | 0.0405 (16) | 0.0346 (14) | 0.0032 (13) | −0.0043 (13) | −0.0041 (11) |
C20 | 0.057 (2) | 0.0422 (17) | 0.0388 (14) | 0.0046 (14) | −0.0095 (14) | −0.0070 (12) |
O5 | 0.141 (3) | 0.106 (3) | 0.0715 (17) | −0.085 (2) | 0.040 (2) | −0.0304 (16) |
C22 | 0.115 (4) | 0.066 (3) | 0.092 (3) | −0.023 (3) | 0.052 (3) | −0.018 (2) |
Geometric parameters (Å, º) top
Br1—C16 | 1.965 (3) | C11—C12 | 1.514 (4) |
O1—C3 | 1.231 (3) | C12—C13 | 1.528 (4) |
O2—C11 | 1.207 (3) | C12—H12A | 0.9700 |
O3—C17 | 1.436 (3) | C12—H12B | 0.9700 |
O3—H3A | 0.8200 | C13—C14 | 1.541 (3) |
O4—C18 | 1.209 (3) | C13—C21 | 1.539 (4) |
C1—C2 | 1.525 (4) | C13—C17 | 1.546 (4) |
C1—C10 | 1.540 (4) | C14—C15 | 1.529 (3) |
C1—H1A | 0.9700 | C14—H14A | 0.9800 |
C1—H1B | 0.9700 | C15—C16 | 1.535 (4) |
C2—C3 | 1.496 (4) | C15—H15A | 0.9700 |
C2—H2A | 0.9700 | C15—H15B | 0.9700 |
C2—H2B | 0.9700 | C16—C17 | 1.562 (4) |
C3—C4 | 1.451 (4) | C16—H16A | 0.9800 |
C4—C5 | 1.347 (4) | C17—C18 | 1.541 (4) |
C4—H4A | 0.9300 | C18—C19 | 1.500 (4) |
C5—C6 | 1.501 (4) | C19—H19A | 0.9600 |
C5—C10 | 1.524 (4) | C19—H19B | 0.9600 |
C6—C7 | 1.526 (4) | C19—H19C | 0.9600 |
C6—H6A | 0.9700 | C21—H21A | 0.9600 |
C6—H6B | 0.9700 | C21—H21B | 0.9600 |
C7—C8 | 1.532 (3) | C21—H21C | 0.9600 |
C7—H7A | 0.9700 | C20—H20A | 0.9600 |
C7—H7B | 0.9700 | C20—H20B | 0.9600 |
C8—C14 | 1.529 (4) | C20—H20C | 0.9600 |
C8—C9 | 1.546 (4) | O5—C22 | 1.361 (5) |
C8—H8A | 0.9800 | O5—H5 | 0.8200 |
C9—C11 | 1.529 (3) | C22—H22A | 0.9600 |
C9—C10 | 1.562 (4) | C22—H22B | 0.9600 |
C9—H9A | 0.9800 | C22—H22C | 0.9600 |
C10—C20 | 1.545 (4) | | |
| | | |
C17—O3—H3A | 109.5 | H12A—C12—H12B | 108.2 |
C2—C1—C10 | 113.6 (2) | C12—C13—C14 | 107.53 (19) |
C2—C1—H1A | 108.8 | C12—C13—C21 | 109.4 (2) |
C10—C1—H1A | 108.8 | C14—C13—C21 | 111.8 (2) |
C2—C1—H1B | 108.8 | C12—C13—C17 | 115.7 (2) |
C10—C1—H1B | 108.8 | C14—C13—C17 | 99.87 (19) |
H1A—C1—H1B | 107.7 | C21—C13—C17 | 112.2 (2) |
C3—C2—C1 | 109.4 (2) | C8—C14—C15 | 118.1 (2) |
C3—C2—H2A | 109.8 | C8—C14—C13 | 114.2 (2) |
C1—C2—H2A | 109.8 | C15—C14—C13 | 103.4 (2) |
C3—C2—H2B | 109.8 | C8—C14—H14A | 106.8 |
C1—C2—H2B | 109.8 | C15—C14—H14A | 106.8 |
H2A—C2—H2B | 108.2 | C13—C14—H14A | 106.8 |
O1—C3—C4 | 122.4 (3) | C14—C15—C16 | 103.3 (2) |
O1—C3—C2 | 122.2 (3) | C14—C15—H15A | 111.1 |
C4—C3—C2 | 115.4 (3) | C16—C15—H15A | 111.1 |
C5—C4—C3 | 123.3 (2) | C14—C15—H15B | 111.1 |
C5—C4—H4A | 118.4 | C16—C15—H15B | 111.1 |
C3—C4—H4A | 118.4 | H15A—C15—H15B | 109.1 |
C4—C5—C6 | 120.7 (2) | C15—C16—C17 | 107.1 (2) |
C4—C5—C10 | 123.2 (2) | C15—C16—Br1 | 110.98 (18) |
C6—C5—C10 | 116.1 (2) | C17—C16—Br1 | 114.86 (17) |
C5—C6—C7 | 112.1 (2) | C15—C16—H16A | 107.9 |
C5—C6—H6A | 109.2 | C17—C16—H16A | 107.9 |
C7—C6—H6A | 109.2 | Br1—C16—H16A | 107.9 |
C5—C6—H6B | 109.2 | O3—C17—C18 | 106.1 (2) |
C7—C6—H6B | 109.2 | O3—C17—C13 | 111.26 (19) |
H6A—C6—H6B | 107.9 | C18—C17—C13 | 116.7 (2) |
C6—C7—C8 | 111.9 (2) | O3—C17—C16 | 101.6 (2) |
C6—C7—H7A | 109.2 | C18—C17—C16 | 117.4 (2) |
C8—C7—H7A | 109.2 | C13—C17—C16 | 102.9 (2) |
C6—C7—H7B | 109.2 | O4—C18—C19 | 120.8 (3) |
C8—C7—H7B | 109.2 | O4—C18—C17 | 120.5 (3) |
H7A—C7—H7B | 107.9 | C19—C18—C17 | 118.5 (2) |
C14—C8—C7 | 110.5 (2) | C18—C19—H19A | 109.5 |
C14—C8—C9 | 108.40 (19) | C18—C19—H19B | 109.5 |
C7—C8—C9 | 110.6 (2) | H19A—C19—H19B | 109.5 |
C14—C8—H8A | 109.1 | C18—C19—H19C | 109.5 |
C7—C8—H8A | 109.1 | H19A—C19—H19C | 109.5 |
C9—C8—H8A | 109.1 | H19B—C19—H19C | 109.5 |
C11—C9—C8 | 110.2 (2) | C13—C21—H21A | 109.5 |
C11—C9—C10 | 115.6 (2) | C13—C21—H21B | 109.5 |
C8—C9—C10 | 114.7 (2) | H21A—C21—H21B | 109.5 |
C11—C9—H9A | 105.0 | C13—C21—H21C | 109.5 |
C8—C9—H9A | 105.0 | H21A—C21—H21C | 109.5 |
C10—C9—H9A | 105.0 | H21B—C21—H21C | 109.5 |
C5—C10—C1 | 110.1 (2) | C10—C20—H20A | 109.5 |
C5—C10—C20 | 108.6 (2) | C10—C20—H20B | 109.5 |
C1—C10—C20 | 109.9 (2) | H20A—C20—H20B | 109.5 |
C5—C10—C9 | 106.7 (2) | C10—C20—H20C | 109.5 |
C1—C10—C9 | 108.7 (2) | H20A—C20—H20C | 109.5 |
C20—C10—C9 | 112.7 (2) | H20B—C20—H20C | 109.5 |
O2—C11—C12 | 121.2 (2) | C22—O5—H5 | 109.5 |
O2—C11—C9 | 123.8 (3) | O5—C22—H22A | 109.5 |
C12—C11—C9 | 114.9 (2) | O5—C22—H22B | 109.5 |
C11—C12—C13 | 109.4 (2) | H22A—C22—H22B | 109.5 |
C11—C12—H12A | 109.8 | O5—C22—H22C | 109.5 |
C13—C12—H12A | 109.8 | H22A—C22—H22C | 109.5 |
C11—C12—H12B | 109.8 | H22B—C22—H22C | 109.5 |
C13—C12—H12B | 109.8 | | |
| | | |
C10—C1—C2—C3 | −58.8 (3) | C11—C12—C13—C21 | −64.7 (3) |
C1—C2—C3—O1 | −138.5 (3) | C11—C12—C13—C17 | 167.5 (2) |
C1—C2—C3—C4 | 43.1 (3) | C7—C8—C14—C15 | −58.8 (3) |
O1—C3—C4—C5 | 169.3 (3) | C9—C8—C14—C15 | 179.8 (2) |
C2—C3—C4—C5 | −12.4 (4) | C7—C8—C14—C13 | 179.3 (2) |
C3—C4—C5—C6 | 174.5 (3) | C9—C8—C14—C13 | 57.9 (3) |
C3—C4—C5—C10 | −5.9 (4) | C12—C13—C14—C8 | −60.7 (3) |
C4—C5—C6—C7 | 124.8 (3) | C21—C13—C14—C8 | 59.4 (3) |
C10—C5—C6—C7 | −54.9 (3) | C17—C13—C14—C8 | 178.27 (19) |
C5—C6—C7—C8 | 52.1 (3) | C12—C13—C14—C15 | 169.7 (2) |
C6—C7—C8—C14 | −171.9 (2) | C21—C13—C14—C15 | −70.2 (3) |
C6—C7—C8—C9 | −51.9 (3) | C17—C13—C14—C15 | 48.7 (2) |
C14—C8—C9—C11 | −51.8 (3) | C8—C14—C15—C16 | −164.0 (2) |
C7—C8—C9—C11 | −173.1 (2) | C13—C14—C15—C16 | −36.8 (3) |
C14—C8—C9—C10 | 175.67 (19) | C14—C15—C16—C17 | 10.6 (3) |
C7—C8—C9—C10 | 54.3 (3) | C14—C15—C16—Br1 | 136.77 (18) |
C4—C5—C10—C1 | −8.9 (4) | C12—C13—C17—O3 | −47.6 (3) |
C6—C5—C10—C1 | 170.8 (3) | C14—C13—C17—O3 | 67.4 (2) |
C4—C5—C10—C20 | 111.5 (3) | C21—C13—C17—O3 | −174.0 (2) |
C6—C5—C10—C20 | −68.8 (3) | C12—C13—C17—C18 | 74.3 (3) |
C4—C5—C10—C9 | −126.7 (3) | C14—C13—C17—C18 | −170.6 (2) |
C6—C5—C10—C9 | 53.0 (3) | C21—C13—C17—C18 | −52.1 (3) |
C2—C1—C10—C5 | 41.1 (3) | C12—C13—C17—C16 | −155.7 (2) |
C2—C1—C10—C20 | −78.5 (3) | C14—C13—C17—C16 | −40.6 (2) |
C2—C1—C10—C9 | 157.7 (2) | C21—C13—C17—C16 | 77.9 (2) |
C11—C9—C10—C5 | 177.3 (2) | C15—C16—C17—O3 | −96.2 (2) |
C8—C9—C10—C5 | −52.7 (3) | Br1—C16—C17—O3 | 140.03 (17) |
C11—C9—C10—C1 | 58.6 (3) | C15—C16—C17—C18 | 148.6 (2) |
C8—C9—C10—C1 | −171.5 (2) | Br1—C16—C17—C18 | 24.8 (3) |
C11—C9—C10—C20 | −63.5 (3) | C15—C16—C17—C13 | 19.1 (3) |
C8—C9—C10—C20 | 66.4 (3) | Br1—C16—C17—C13 | −104.7 (2) |
C8—C9—C11—O2 | −124.0 (3) | O3—C17—C18—O4 | 118.6 (3) |
C10—C9—C11—O2 | 8.1 (4) | C13—C17—C18—O4 | −6.0 (4) |
C8—C9—C11—C12 | 54.7 (3) | C16—C17—C18—O4 | −128.7 (3) |
C10—C9—C11—C12 | −173.2 (2) | O3—C17—C18—C19 | −55.9 (3) |
O2—C11—C12—C13 | 121.2 (3) | C13—C17—C18—C19 | 179.5 (3) |
C9—C11—C12—C13 | −57.5 (3) | C16—C17—C18—C19 | 56.8 (3) |
C11—C12—C13—C14 | 56.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.82 | 2.06 | 2.823 (4) | 155 |
O3—H3A···O5 | 0.82 | 1.93 | 2.674 (3) | 150 |
Symmetry code: (i) x−1/2, −y+1/2, −z+2. |