The title compound, C
21H
29BrO
3·CH
3OH, is a steroid and an intermediate for medicinal applications. It is prepared through the reaction of 16,17-epoxypregn-4-ene-3,20-dione and HBr, and the methanol solvate is reported here. The space group is
and is different from the space group of 16β-bromo-17α-hydroxypregn-4-ene-3,20-dione which is
C2 [Wang, Wang, Nie, Xiang & Zhou (2005).
Acta Cryst. E
61, o1–o2].
Supporting information
CCDC reference: 269845
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.066
- wR factor = 0.192
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
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 25.01
From the CIF: _reflns_number_total 3705
Count of symmetry unique reflns 2173
Completeness (_total/calc) 170.50%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1532
Fraction of Friedel pairs measured 0.705
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.
16
β-Bromo-17
α-hydroxypregn-4-ene-3,20-dione methanol solvate
top
Crystal data top
C21H29BrO3·CH4O | Dx = 1.381 Mg m−3 |
Mr = 441.39 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3797 reflections |
a = 12.008 (3) Å | θ = 2.3–25.7° |
b = 25.192 (6) Å | µ = 1.96 mm−1 |
c = 7.0192 (12) Å | T = 293 K |
V = 2123.4 (8) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.38 × 0.30 mm |
F(000) = 928 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3705 independent reflections |
Radiation source: fine-focus sealed tube | 2879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −6→14 |
Tmin = 0.421, Tmax = 0.555 | k = −29→29 |
10348 measured reflections | l = −8→8 |
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)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.192 | w = 1/[σ2(Fo2) + (0.0659P)2 + 10.8219P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3705 reflections | Δρmax = 1.02 e Å−3 |
247 parameters | Δρmin = −0.57 e Å−3 |
6 restraints | Absolute structure: Flack (1983), 0000 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.08 (2) |
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 | −0.12607 (9) | 0.87544 (4) | 0.16222 (12) | 0.0529 (3) | |
O1 | 0.5151 (6) | 0.8119 (3) | 1.3759 (10) | 0.061 (2) | |
O2 | −0.1125 (6) | 1.0042 (3) | 0.4572 (12) | 0.063 (2) | |
O3 | −0.1555 (5) | 0.9017 (3) | 0.7367 (8) | 0.0409 (15) | |
H3 | −0.2109 | 0.8814 | 0.7171 | 0.061* | |
C1 | 0.3565 (7) | 0.9067 (3) | 1.1090 (12) | 0.038 (2) | |
H1A | 0.3590 | 0.9446 | 1.0842 | 0.046* | |
H1B | 0.2948 | 0.9002 | 1.1951 | 0.046* | |
C2 | 0.4638 (7) | 0.8905 (3) | 1.2076 (14) | 0.043 (2) | |
H2A | 0.5270 | 0.9017 | 1.1313 | 0.051* | |
H2B | 0.4688 | 0.9081 | 1.3303 | 0.051* | |
C3 | 0.4676 (8) | 0.8316 (4) | 1.2355 (13) | 0.042 (2) | |
C4 | 0.4161 (8) | 0.7997 (3) | 1.0933 (14) | 0.042 (2) | |
H4 | 0.4224 | 0.7630 | 1.1039 | 0.050* | |
C5 | 0.3584 (7) | 0.8194 (3) | 0.9433 (11) | 0.0346 (18) | |
C6 | 0.3198 (8) | 0.7835 (3) | 0.7827 (15) | 0.045 (2) | |
H6A | 0.3653 | 0.7900 | 0.6710 | 0.054* | |
H6B | 0.3302 | 0.7468 | 0.8202 | 0.054* | |
C7 | 0.1990 (8) | 0.7923 (3) | 0.7323 (14) | 0.042 (2) | |
H7A | 0.1804 | 0.7712 | 0.6211 | 0.051* | |
H7B | 0.1525 | 0.7804 | 0.8370 | 0.051* | |
C8 | 0.1748 (7) | 0.8499 (3) | 0.6916 (11) | 0.0273 (17) | |
H8 | 0.2188 | 0.8609 | 0.5809 | 0.033* | |
C9 | 0.2086 (6) | 0.8849 (3) | 0.8642 (11) | 0.0288 (17) | |
H9 | 0.1651 | 0.8718 | 0.9726 | 0.035* | |
C10 | 0.3336 (6) | 0.8777 (3) | 0.9210 (10) | 0.0269 (15) | |
C11 | 0.1751 (7) | 0.9437 (3) | 0.8382 (15) | 0.0358 (18) | |
H11A | 0.1897 | 0.9626 | 0.9558 | 0.043* | |
H11B | 0.2212 | 0.9593 | 0.7395 | 0.043* | |
C12 | 0.0524 (7) | 0.9510 (3) | 0.7845 (11) | 0.0309 (19) | |
H12A | 0.0055 | 0.9397 | 0.8894 | 0.037* | |
H12B | 0.0376 | 0.9883 | 0.7603 | 0.037* | |
C13 | 0.0248 (7) | 0.9185 (3) | 0.6071 (10) | 0.0270 (17) | |
C14 | −0.1005 (7) | 0.9133 (3) | 0.5617 (12) | 0.0349 (19) | |
C15 | −0.1096 (6) | 0.8620 (3) | 0.4352 (10) | 0.0247 (16) | |
H15 | −0.1736 | 0.8411 | 0.4788 | 0.030* | |
C16 | 0.0005 (8) | 0.8302 (3) | 0.4824 (13) | 0.039 (2) | |
H16A | −0.0166 | 0.7939 | 0.5179 | 0.047* | |
H16B | 0.0503 | 0.8298 | 0.3737 | 0.047* | |
C17 | 0.0525 (7) | 0.8601 (3) | 0.6491 (12) | 0.0286 (17) | |
H17 | 0.0106 | 0.8501 | 0.7634 | 0.034* | |
C18 | 0.4119 (7) | 0.9011 (4) | 0.7644 (15) | 0.044 (2) | |
H18A | 0.4881 | 0.8964 | 0.8022 | 0.066* | |
H18B | 0.3968 | 0.9382 | 0.7487 | 0.066* | |
H18C | 0.3991 | 0.8830 | 0.6461 | 0.066* | |
C19 | 0.0883 (7) | 0.9399 (3) | 0.4300 (12) | 0.035 (2) | |
H19A | 0.0732 | 0.9770 | 0.4149 | 0.053* | |
H19B | 0.0641 | 0.9211 | 0.3185 | 0.053* | |
H19C | 0.1668 | 0.9346 | 0.4473 | 0.053* | |
C20 | −0.1604 (8) | 0.9625 (4) | 0.4785 (13) | 0.044 (2) | |
C21 | −0.2861 (8) | 0.9597 (4) | 0.4574 (16) | 0.057 (3) | |
H21A | −0.3207 | 0.9708 | 0.5740 | 0.085* | |
H21B | −0.3077 | 0.9238 | 0.4292 | 0.085* | |
H21C | −0.3094 | 0.9826 | 0.3556 | 0.085* | |
O4 | 0.6590 (6) | 0.8347 (3) | 0.6709 (14) | 0.070 (2) | |
H4A | 0.6387 | 0.8260 | 0.5639 | 0.106* | |
C22 | 0.6698 (10) | 0.7886 (5) | 0.7866 (18) | 0.072 (4) | |
H22A | 0.7333 | 0.7685 | 0.7455 | 0.108* | |
H22B | 0.6040 | 0.7672 | 0.7752 | 0.108* | |
H22C | 0.6796 | 0.7990 | 0.9171 | 0.108* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0775 (7) | 0.0591 (5) | 0.0221 (4) | −0.0076 (6) | −0.0097 (5) | 0.0029 (4) |
O1 | 0.077 (5) | 0.065 (4) | 0.041 (4) | 0.014 (4) | −0.018 (4) | 0.002 (3) |
O2 | 0.058 (4) | 0.041 (4) | 0.089 (6) | 0.002 (3) | −0.007 (4) | 0.017 (3) |
O3 | 0.032 (3) | 0.072 (4) | 0.019 (3) | −0.007 (3) | 0.004 (2) | 0.001 (3) |
C1 | 0.042 (5) | 0.030 (4) | 0.042 (5) | 0.000 (4) | −0.019 (4) | 0.000 (3) |
C2 | 0.031 (5) | 0.051 (5) | 0.047 (6) | 0.002 (4) | −0.017 (4) | −0.006 (4) |
C3 | 0.042 (5) | 0.053 (6) | 0.031 (5) | 0.007 (4) | −0.007 (4) | 0.001 (4) |
C4 | 0.050 (6) | 0.031 (4) | 0.044 (5) | 0.003 (4) | 0.000 (4) | 0.001 (4) |
C5 | 0.034 (5) | 0.038 (4) | 0.032 (4) | 0.000 (4) | −0.007 (4) | −0.001 (3) |
C6 | 0.051 (6) | 0.028 (4) | 0.055 (6) | 0.010 (4) | −0.006 (5) | −0.008 (4) |
C7 | 0.049 (6) | 0.030 (5) | 0.047 (5) | −0.001 (4) | −0.014 (4) | −0.012 (4) |
C8 | 0.040 (4) | 0.026 (4) | 0.016 (4) | −0.004 (3) | 0.003 (3) | 0.001 (3) |
C9 | 0.029 (4) | 0.032 (4) | 0.026 (4) | −0.004 (3) | 0.002 (3) | −0.004 (3) |
C10 | 0.025 (4) | 0.031 (4) | 0.025 (3) | 0.000 (3) | 0.001 (3) | −0.005 (4) |
C11 | 0.035 (4) | 0.031 (4) | 0.041 (5) | −0.003 (3) | −0.003 (4) | −0.005 (4) |
C12 | 0.040 (5) | 0.028 (4) | 0.025 (4) | 0.002 (3) | −0.004 (3) | 0.000 (3) |
C13 | 0.031 (4) | 0.031 (4) | 0.020 (4) | −0.001 (3) | 0.006 (3) | 0.003 (3) |
C14 | 0.038 (5) | 0.032 (4) | 0.034 (4) | −0.004 (4) | 0.000 (4) | 0.000 (3) |
C15 | 0.0255 (18) | 0.0258 (18) | 0.0228 (17) | −0.0013 (10) | −0.0004 (10) | 0.0000 (10) |
C16 | 0.052 (6) | 0.034 (5) | 0.031 (5) | −0.003 (4) | −0.018 (4) | −0.003 (4) |
C17 | 0.040 (4) | 0.025 (4) | 0.022 (4) | −0.004 (3) | −0.005 (4) | −0.001 (3) |
C18 | 0.038 (5) | 0.041 (5) | 0.053 (6) | −0.003 (4) | 0.003 (4) | 0.004 (4) |
C19 | 0.042 (5) | 0.037 (5) | 0.027 (4) | −0.007 (4) | 0.010 (4) | 0.003 (3) |
C20 | 0.052 (6) | 0.044 (5) | 0.035 (5) | 0.005 (4) | −0.011 (4) | 0.007 (4) |
C21 | 0.046 (6) | 0.071 (7) | 0.053 (6) | 0.004 (5) | −0.018 (5) | 0.007 (5) |
O4 | 0.047 (4) | 0.086 (5) | 0.078 (6) | −0.014 (4) | −0.007 (4) | 0.012 (5) |
C22 | 0.073 (8) | 0.077 (8) | 0.066 (8) | −0.003 (6) | −0.017 (6) | 0.019 (6) |
Geometric parameters (Å, º) top
Br1—C15 | 1.956 (7) | C11—H11A | 0.9700 |
O1—C3 | 1.242 (11) | C11—H11B | 0.9700 |
O2—C20 | 1.206 (11) | C12—C13 | 1.527 (10) |
O3—C14 | 1.426 (10) | C12—H12A | 0.9700 |
O3—H3 | 0.8500 | C12—H12B | 0.9700 |
C1—C2 | 1.519 (11) | C13—C17 | 1.538 (10) |
C1—C10 | 1.533 (11) | C13—C14 | 1.544 (12) |
C1—H1A | 0.9700 | C13—C19 | 1.553 (10) |
C1—H1B | 0.9700 | C14—C20 | 1.548 (12) |
C2—C3 | 1.497 (13) | C14—C15 | 1.573 (10) |
C2—H2A | 0.9700 | C15—C16 | 1.580 (12) |
C2—H2B | 0.9700 | C15—H15 | 0.9800 |
C3—C4 | 1.424 (13) | C16—C17 | 1.525 (11) |
C4—C5 | 1.354 (12) | C16—H16A | 0.9700 |
C4—H4 | 0.9300 | C16—H16B | 0.9700 |
C5—C10 | 1.507 (11) | C17—H17 | 0.9800 |
C5—C6 | 1.518 (12) | C18—H18A | 0.9600 |
C6—C7 | 1.509 (12) | C18—H18B | 0.9600 |
C6—H6A | 0.9700 | C18—H18C | 0.9600 |
C6—H6B | 0.9700 | C19—H19A | 0.9600 |
C7—C8 | 1.508 (11) | C19—H19B | 0.9600 |
C7—H7A | 0.9700 | C19—H19C | 0.9600 |
C7—H7B | 0.9700 | C20—C21 | 1.518 (14) |
C8—C17 | 1.520 (11) | C21—H21A | 0.9600 |
C8—C9 | 1.553 (10) | C21—H21B | 0.9600 |
C8—H8 | 0.9800 | C21—H21C | 0.9600 |
C9—C11 | 1.545 (10) | O4—C22 | 1.424 (13) |
C9—C10 | 1.564 (10) | O4—H4A | 0.8200 |
C9—H9 | 0.9800 | C22—H22A | 0.9600 |
C10—C18 | 1.561 (12) | C22—H22B | 0.9600 |
C11—C12 | 1.532 (11) | C22—H22C | 0.9600 |
| | | |
C14—O3—H3 | 110.3 | C13—C12—H12B | 109.6 |
C2—C1—C10 | 114.6 (7) | C11—C12—H12B | 109.6 |
C2—C1—H1A | 108.6 | H12A—C12—H12B | 108.1 |
C10—C1—H1A | 108.6 | C12—C13—C17 | 108.1 (6) |
C2—C1—H1B | 108.6 | C12—C13—C14 | 115.1 (7) |
C10—C1—H1B | 108.6 | C17—C13—C14 | 99.7 (6) |
H1A—C1—H1B | 107.6 | C12—C13—C19 | 111.1 (6) |
C3—C2—C1 | 110.6 (7) | C17—C13—C19 | 112.2 (7) |
C3—C2—H2A | 109.5 | C14—C13—C19 | 110.0 (7) |
C1—C2—H2A | 109.5 | O3—C14—C13 | 106.9 (6) |
C3—C2—H2B | 109.5 | O3—C14—C20 | 105.9 (7) |
C1—C2—H2B | 109.5 | C13—C14—C20 | 117.6 (7) |
H2A—C2—H2B | 108.1 | O3—C14—C15 | 106.6 (6) |
O1—C3—C4 | 122.0 (8) | C13—C14—C15 | 104.7 (6) |
O1—C3—C2 | 120.9 (9) | C20—C14—C15 | 114.4 (7) |
C4—C3—C2 | 117.0 (8) | C14—C15—C16 | 103.9 (6) |
C5—C4—C3 | 124.1 (8) | C14—C15—Br1 | 114.6 (5) |
C5—C4—H4 | 118.0 | C16—C15—Br1 | 112.2 (5) |
C3—C4—H4 | 118.0 | C14—C15—H15 | 108.6 |
C4—C5—C10 | 122.7 (7) | C16—C15—H15 | 108.6 |
C4—C5—C6 | 121.0 (7) | Br1—C15—H15 | 108.6 |
C10—C5—C6 | 116.3 (7) | C17—C16—C15 | 104.7 (6) |
C7—C6—C5 | 112.4 (7) | C17—C16—H16A | 110.8 |
C7—C6—H6A | 109.1 | C15—C16—H16A | 110.8 |
C5—C6—H6A | 109.1 | C17—C16—H16B | 110.8 |
C7—C6—H6B | 109.1 | C15—C16—H16B | 110.8 |
C5—C6—H6B | 109.1 | H16A—C16—H16B | 108.9 |
H6A—C6—H6B | 107.9 | C8—C17—C16 | 117.6 (7) |
C8—C7—C6 | 111.8 (7) | C8—C17—C13 | 114.1 (6) |
C8—C7—H7A | 109.3 | C16—C17—C13 | 103.7 (6) |
C6—C7—H7A | 109.3 | C8—C17—H17 | 106.9 |
C8—C7—H7B | 109.3 | C16—C17—H17 | 106.9 |
C6—C7—H7B | 109.3 | C13—C17—H17 | 106.9 |
H7A—C7—H7B | 107.9 | C10—C18—H18A | 109.5 |
C7—C8—C17 | 112.7 (6) | C10—C18—H18B | 109.5 |
C7—C8—C9 | 110.4 (6) | H18A—C18—H18B | 109.5 |
C17—C8—C9 | 108.1 (6) | C10—C18—H18C | 109.5 |
C7—C8—H8 | 108.5 | H18A—C18—H18C | 109.5 |
C17—C8—H8 | 108.5 | H18B—C18—H18C | 109.5 |
C9—C8—H8 | 108.5 | C13—C19—H19A | 109.5 |
C11—C9—C8 | 112.6 (6) | C13—C19—H19B | 109.5 |
C11—C9—C10 | 113.0 (6) | H19A—C19—H19B | 109.5 |
C8—C9—C10 | 112.6 (6) | C13—C19—H19C | 109.5 |
C11—C9—H9 | 106.0 | H19A—C19—H19C | 109.5 |
C8—C9—H9 | 106.0 | H19B—C19—H19C | 109.5 |
C10—C9—H9 | 106.0 | O2—C20—C21 | 120.2 (9) |
C5—C10—C1 | 109.8 (6) | O2—C20—C14 | 121.4 (8) |
C5—C10—C18 | 108.7 (6) | C21—C20—C14 | 117.5 (8) |
C1—C10—C18 | 108.6 (7) | C20—C21—H21A | 109.5 |
C5—C10—C9 | 109.2 (6) | C20—C21—H21B | 109.5 |
C1—C10—C9 | 109.7 (6) | H21A—C21—H21B | 109.5 |
C18—C10—C9 | 110.8 (7) | C20—C21—H21C | 109.5 |
C12—C11—C9 | 113.3 (6) | H21A—C21—H21C | 109.5 |
C12—C11—H11A | 108.9 | H21B—C21—H21C | 109.5 |
C9—C11—H11A | 108.9 | C22—O4—H4A | 109.4 |
C12—C11—H11B | 108.9 | O4—C22—H22A | 109.4 |
C9—C11—H11B | 108.9 | O4—C22—H22B | 109.6 |
H11A—C11—H11B | 107.7 | H22A—C22—H22B | 109.5 |
C13—C12—C11 | 110.1 (7) | O4—C22—H22C | 109.4 |
C13—C12—H12A | 109.6 | H22A—C22—H22C | 109.5 |
C11—C12—H12A | 109.6 | H22B—C22—H22C | 109.5 |
| | | |
C10—C1—C2—C3 | −54.0 (11) | C11—C12—C13—C19 | −65.9 (8) |
C1—C2—C3—O1 | −147.6 (9) | C12—C13—C14—O3 | −44.6 (8) |
C1—C2—C3—C4 | 33.3 (12) | C17—C13—C14—O3 | 70.7 (7) |
O1—C3—C4—C5 | 176.4 (9) | C19—C13—C14—O3 | −171.1 (6) |
C2—C3—C4—C5 | −4.5 (15) | C12—C13—C14—C20 | 74.2 (9) |
C3—C4—C5—C10 | −5.8 (15) | C17—C13—C14—C20 | −170.4 (7) |
C3—C4—C5—C6 | 171.3 (9) | C19—C13—C14—C20 | −52.3 (9) |
C4—C5—C6—C7 | 132.1 (9) | C12—C13—C14—C15 | −157.4 (6) |
C10—C5—C6—C7 | −50.7 (11) | C17—C13—C14—C15 | −42.1 (7) |
C5—C6—C7—C8 | 53.1 (11) | C19—C13—C14—C15 | 76.0 (7) |
C6—C7—C8—C17 | −177.4 (8) | O3—C14—C15—C16 | −92.1 (7) |
C6—C7—C8—C9 | −56.5 (10) | C13—C14—C15—C16 | 21.0 (8) |
C7—C8—C9—C11 | −174.4 (7) | C20—C14—C15—C16 | 151.2 (7) |
C17—C8—C9—C11 | −50.7 (8) | O3—C14—C15—Br1 | 145.1 (5) |
C7—C8—C9—C10 | 56.4 (9) | C13—C14—C15—Br1 | −101.8 (6) |
C17—C8—C9—C10 | −179.9 (6) | C20—C14—C15—Br1 | 28.4 (9) |
C4—C5—C10—C1 | −13.9 (11) | C14—C15—C16—C17 | 8.6 (8) |
C6—C5—C10—C1 | 168.9 (7) | Br1—C15—C16—C17 | 133.0 (6) |
C4—C5—C10—C18 | 104.8 (10) | C7—C8—C17—C16 | −58.3 (10) |
C6—C5—C10—C18 | −72.4 (9) | C9—C8—C17—C16 | 179.4 (7) |
C4—C5—C10—C9 | −134.2 (9) | C7—C8—C17—C13 | 179.9 (7) |
C6—C5—C10—C9 | 48.6 (10) | C9—C8—C17—C13 | 57.7 (8) |
C2—C1—C10—C5 | 43.8 (10) | C15—C16—C17—C8 | −162.4 (6) |
C2—C1—C10—C18 | −75.0 (9) | C15—C16—C17—C13 | −35.4 (8) |
C2—C1—C10—C9 | 163.7 (7) | C12—C13—C17—C8 | −62.1 (9) |
C11—C9—C10—C5 | 179.9 (7) | C14—C13—C17—C8 | 177.2 (7) |
C8—C9—C10—C5 | −51.1 (8) | C19—C13—C17—C8 | 60.8 (9) |
C11—C9—C10—C1 | 59.6 (9) | C12—C13—C17—C16 | 168.7 (7) |
C8—C9—C10—C1 | −171.5 (6) | C14—C13—C17—C16 | 48.1 (8) |
C11—C9—C10—C18 | −60.3 (9) | C19—C13—C17—C16 | −68.4 (8) |
C8—C9—C10—C18 | 68.6 (8) | O3—C14—C20—O2 | 116.4 (9) |
C8—C9—C11—C12 | 51.6 (10) | C13—C14—C20—O2 | −3.0 (13) |
C10—C9—C11—C12 | −179.4 (7) | C15—C14—C20—O2 | −126.6 (9) |
C9—C11—C12—C13 | −54.8 (9) | O3—C14—C20—C21 | −53.1 (10) |
C11—C12—C13—C17 | 57.7 (8) | C13—C14—C20—C21 | −172.5 (8) |
C11—C12—C13—C14 | 168.1 (7) | C15—C14—C20—C21 | 64.0 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O1i | 0.82 | 2.02 | 2.757 (11) | 150 |
O3—H3···O4ii | 0.85 | 1.98 | 2.832 (9) | 180 |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z. |