In the title molecule, C
22H
29ClO
4, all bond lengths and angles show normal values. Rings
A and
C have slightly distorted chair conformations, while rings
B and
D show envelope conformations. Weak intermolecular C—H
O hydrogen bonds link the molecules into chains running along the
b axis.
Supporting information
CCDC reference: 636224
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.128
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.49 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
PLAT338_ALERT_2_C Small Average Tau in cyclohexane C5 -C10 34.42 Deg.
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 27.00
From the CIF: _reflns_number_total 4150
Count of symmetry unique reflns 2390
Completeness (_total/calc) 173.64%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1760
Fraction of Friedel pairs measured 0.736
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 C3 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
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 C15 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
14 ALERT level G = General alerts; check
13 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
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.05; Farrugia, 1997); software used to prepare material for publication: SHELXL97.
3
β-Acetoxy-7
α-chloro-5,6
β-epoxy-15
β,16
β-methylene-5
β-androstan-17-one
top
Crystal data top
C22H29ClO4 | F(000) = 420 |
Mr = 392.90 | Dx = 1.291 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 841 reflections |
a = 11.741 (5) Å | θ = 3.4–26.0° |
b = 6.911 (3) Å | µ = 0.21 mm−1 |
c = 12.457 (5) Å | T = 293 K |
β = 90.958 (5)° | Prismatic, colourless |
V = 1010.7 (7) Å3 | 0.20 × 0.15 × 0.14 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3484 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.0°, θmin = 1.6° |
φ and ω scans | h = −14→14 |
4915 measured reflections | k = −8→8 |
4150 independent reflections | l = −9→15 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.0809P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.35 e Å−3 |
4150 reflections | Δρmin = −0.35 e Å−3 |
248 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.062 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with how many Friedel pairs? |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.01 (7) |
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 | |
Cl1 | 0.65638 (6) | 0.33471 (13) | 0.06395 (5) | 0.0711 (3) | |
O1 | 0.14366 (14) | 0.4115 (4) | 0.07417 (14) | 0.0650 (6) | |
O2 | 0.2083 (2) | 0.3478 (6) | −0.0863 (2) | 0.1164 (11) | |
O3 | 0.45286 (16) | 0.1328 (2) | 0.28765 (18) | 0.0585 (5) | |
O4 | 0.99306 (18) | 0.7114 (4) | 0.3824 (2) | 0.0801 (7) | |
C1 | 0.38676 (19) | 0.6600 (3) | 0.2136 (2) | 0.0439 (5) | |
H1A | 0.3900 | 0.7780 | 0.2557 | 0.053* | |
H1B | 0.4309 | 0.6815 | 0.1496 | 0.053* | |
C2 | 0.2627 (2) | 0.6248 (4) | 0.1792 (2) | 0.0488 (6) | |
H2A | 0.2152 | 0.6128 | 0.2418 | 0.059* | |
H2B | 0.2347 | 0.7323 | 0.1361 | 0.059* | |
C3 | 0.25903 (19) | 0.4424 (4) | 0.1152 (2) | 0.0507 (6) | |
H3 | 0.3111 | 0.4536 | 0.0548 | 0.061* | |
C4 | 0.2944 (2) | 0.2738 (4) | 0.1843 (2) | 0.0530 (6) | |
H4A | 0.2901 | 0.1556 | 0.1425 | 0.064* | |
H4B | 0.2426 | 0.2617 | 0.2438 | 0.064* | |
C5 | 0.41482 (19) | 0.3010 (3) | 0.22726 (19) | 0.0440 (5) | |
C6 | 0.5018 (2) | 0.1720 (4) | 0.1863 (2) | 0.0533 (7) | |
H6 | 0.4784 | 0.0870 | 0.1270 | 0.064* | |
C7 | 0.6248 (2) | 0.2251 (4) | 0.1921 (2) | 0.0481 (6) | |
H7 | 0.6701 | 0.1069 | 0.2006 | 0.058* | |
C8 | 0.65179 (18) | 0.3603 (3) | 0.28477 (17) | 0.0377 (5) | |
H8 | 0.6390 | 0.2919 | 0.3524 | 0.045* | |
C9 | 0.57468 (18) | 0.5395 (3) | 0.27993 (17) | 0.0344 (5) | |
H9 | 0.5893 | 0.5988 | 0.2100 | 0.041* | |
C10 | 0.44436 (18) | 0.4972 (3) | 0.27940 (17) | 0.0346 (5) | |
C11 | 0.6106 (2) | 0.6939 (4) | 0.3637 (2) | 0.0448 (6) | |
H11A | 0.5679 | 0.8115 | 0.3494 | 0.054* | |
H11B | 0.5899 | 0.6484 | 0.4344 | 0.054* | |
C12 | 0.7379 (2) | 0.7424 (4) | 0.3650 (2) | 0.0480 (6) | |
H12A | 0.7581 | 0.8040 | 0.2980 | 0.058* | |
H12B | 0.7552 | 0.8315 | 0.4232 | 0.058* | |
C13 | 0.80620 (19) | 0.5575 (4) | 0.37997 (19) | 0.0431 (5) | |
C14 | 0.77437 (19) | 0.4300 (4) | 0.28310 (18) | 0.0418 (5) | |
H14 | 0.7767 | 0.5183 | 0.2216 | 0.050* | |
C15 | 0.8724 (2) | 0.2919 (5) | 0.2654 (2) | 0.0599 (7) | |
H15 | 0.8802 | 0.2351 | 0.1939 | 0.072* | |
C16 | 0.9767 (2) | 0.3903 (5) | 0.3160 (3) | 0.0715 (9) | |
H16 | 1.0478 | 0.3933 | 0.2759 | 0.086* | |
C17 | 0.9352 (2) | 0.5714 (4) | 0.3647 (2) | 0.0558 (7) | |
C18 | 0.7857 (2) | 0.4777 (5) | 0.4939 (2) | 0.0587 (7) | |
H18A | 0.8571 | 0.4406 | 0.5263 | 0.088* | |
H18B | 0.7364 | 0.3671 | 0.4893 | 0.088* | |
H18C | 0.7507 | 0.5759 | 0.5368 | 0.088* | |
C19 | 0.3957 (2) | 0.4926 (4) | 0.3920 (2) | 0.0552 (7) | |
H19A | 0.3179 | 0.4496 | 0.3884 | 0.083* | |
H19B | 0.3988 | 0.6200 | 0.4226 | 0.083* | |
H19C | 0.4395 | 0.4052 | 0.4361 | 0.083* | |
C20 | 0.9331 (2) | 0.1980 (5) | 0.3558 (3) | 0.0738 (10) | |
H20A | 0.9778 | 0.0837 | 0.3403 | 0.089* | |
H20B | 0.8959 | 0.1960 | 0.4247 | 0.089* | |
C21 | 0.1306 (3) | 0.3668 (5) | −0.0282 (2) | 0.0632 (7) | |
C22 | 0.0088 (3) | 0.3531 (7) | −0.0623 (3) | 0.0955 (13) | |
H22A | −0.0090 | 0.4561 | −0.1115 | 0.143* | |
H22B | −0.0386 | 0.3635 | −0.0005 | 0.143* | |
H22C | −0.0046 | 0.2309 | −0.0969 | 0.143* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0788 (5) | 0.0908 (6) | 0.0437 (3) | 0.0003 (4) | 0.0010 (3) | −0.0246 (4) |
O1 | 0.0426 (9) | 0.0966 (16) | 0.0554 (11) | −0.0085 (10) | −0.0094 (8) | −0.0007 (10) |
O2 | 0.1015 (19) | 0.178 (3) | 0.0693 (15) | −0.038 (2) | −0.0047 (13) | −0.035 (2) |
O3 | 0.0581 (11) | 0.0286 (8) | 0.0886 (15) | −0.0030 (8) | −0.0065 (10) | 0.0095 (9) |
O4 | 0.0606 (12) | 0.0726 (14) | 0.1066 (18) | −0.0241 (11) | −0.0171 (12) | −0.0043 (13) |
C1 | 0.0428 (12) | 0.0387 (12) | 0.0501 (13) | 0.0004 (10) | −0.0019 (10) | 0.0095 (10) |
C2 | 0.0437 (13) | 0.0481 (14) | 0.0545 (15) | 0.0016 (11) | −0.0024 (11) | 0.0122 (12) |
C3 | 0.0361 (11) | 0.0693 (18) | 0.0467 (13) | −0.0046 (12) | −0.0028 (10) | 0.0055 (13) |
C4 | 0.0433 (13) | 0.0438 (14) | 0.0717 (17) | −0.0065 (11) | −0.0049 (12) | −0.0037 (12) |
C5 | 0.0428 (12) | 0.0342 (12) | 0.0547 (13) | −0.0032 (10) | −0.0067 (10) | 0.0024 (10) |
C6 | 0.0537 (14) | 0.0331 (13) | 0.0725 (18) | 0.0012 (11) | −0.0158 (13) | −0.0170 (12) |
C7 | 0.0507 (13) | 0.0374 (12) | 0.0559 (14) | 0.0086 (11) | −0.0086 (11) | −0.0116 (11) |
C8 | 0.0397 (10) | 0.0362 (11) | 0.0371 (10) | 0.0023 (10) | −0.0050 (8) | −0.0013 (9) |
C9 | 0.0401 (11) | 0.0311 (11) | 0.0318 (11) | −0.0014 (9) | −0.0020 (8) | −0.0026 (9) |
C10 | 0.0381 (11) | 0.0302 (10) | 0.0354 (11) | 0.0004 (9) | 0.0011 (9) | 0.0036 (9) |
C11 | 0.0517 (13) | 0.0356 (12) | 0.0468 (13) | 0.0028 (11) | −0.0052 (10) | −0.0114 (10) |
C12 | 0.0549 (14) | 0.0393 (13) | 0.0494 (13) | −0.0063 (11) | −0.0091 (11) | −0.0088 (11) |
C13 | 0.0424 (12) | 0.0441 (13) | 0.0427 (13) | −0.0040 (10) | −0.0066 (10) | −0.0033 (10) |
C14 | 0.0423 (12) | 0.0438 (13) | 0.0393 (12) | −0.0001 (10) | 0.0000 (9) | −0.0045 (10) |
C15 | 0.0446 (14) | 0.0695 (19) | 0.0655 (16) | 0.0053 (13) | −0.0018 (11) | −0.0182 (15) |
C16 | 0.0397 (13) | 0.082 (2) | 0.093 (2) | 0.0020 (15) | −0.0008 (13) | −0.0156 (19) |
C17 | 0.0461 (14) | 0.0638 (18) | 0.0570 (16) | −0.0110 (14) | −0.0099 (12) | 0.0014 (13) |
C18 | 0.0611 (15) | 0.0722 (19) | 0.0427 (14) | −0.0027 (15) | −0.0074 (11) | 0.0038 (13) |
C19 | 0.0581 (15) | 0.0640 (17) | 0.0438 (14) | −0.0072 (14) | 0.0103 (11) | 0.0037 (13) |
C20 | 0.0527 (16) | 0.060 (2) | 0.107 (3) | 0.0166 (16) | −0.0235 (17) | −0.0116 (18) |
C21 | 0.0728 (18) | 0.0582 (17) | 0.0580 (16) | −0.0138 (16) | −0.0165 (14) | 0.0035 (14) |
C22 | 0.084 (2) | 0.101 (3) | 0.100 (3) | −0.025 (2) | −0.044 (2) | 0.008 (2) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.811 (3) | C10—C19 | 1.524 (3) |
O1—C21 | 1.319 (3) | C11—C12 | 1.532 (3) |
O1—C3 | 1.456 (3) | C11—H11A | 0.9700 |
O2—C21 | 1.182 (4) | C11—H11B | 0.9700 |
O3—C6 | 1.421 (4) | C12—C13 | 1.519 (3) |
O3—C5 | 1.451 (3) | C12—H12A | 0.9700 |
O4—C17 | 1.201 (3) | C12—H12B | 0.9700 |
C1—C2 | 1.531 (3) | C13—C17 | 1.532 (4) |
C1—C10 | 1.542 (3) | C13—C14 | 1.535 (3) |
C1—H1A | 0.9700 | C13—C18 | 1.545 (4) |
C1—H1B | 0.9700 | C14—C15 | 1.514 (4) |
C2—C3 | 1.492 (4) | C14—H14 | 0.9800 |
C2—H2A | 0.9700 | C15—C20 | 1.473 (4) |
C2—H2B | 0.9700 | C15—C16 | 1.528 (4) |
C3—C4 | 1.503 (4) | C15—H15 | 0.9800 |
C3—H3 | 0.9800 | C16—C17 | 1.477 (5) |
C4—C5 | 1.515 (3) | C16—C20 | 1.511 (5) |
C4—H4A | 0.9700 | C16—H16 | 0.9800 |
C4—H4B | 0.9700 | C18—H18A | 0.9599 |
C5—C6 | 1.454 (4) | C18—H18B | 0.9599 |
C5—C10 | 1.541 (3) | C18—H18C | 0.9599 |
C6—C7 | 1.490 (4) | C19—H19A | 0.9599 |
C6—H6 | 0.9800 | C19—H19B | 0.9599 |
C7—C8 | 1.515 (3) | C19—H19C | 0.9599 |
C7—H7 | 0.9800 | C20—H20A | 0.9700 |
C8—C14 | 1.518 (3) | C20—H20B | 0.9700 |
C8—C9 | 1.535 (3) | C21—C22 | 1.488 (4) |
C8—H8 | 0.9800 | C22—H22A | 0.9599 |
C9—C11 | 1.546 (3) | C22—H22B | 0.9599 |
C9—C10 | 1.558 (3) | C22—H22C | 0.9599 |
C9—H9 | 0.9800 | | |
| | | |
C21—O1—C3 | 117.8 (2) | C9—C11—H11A | 108.7 |
C6—O3—C5 | 60.81 (16) | C12—C11—H11B | 108.7 |
C2—C1—C10 | 116.12 (19) | C9—C11—H11B | 108.7 |
C2—C1—H1A | 108.3 | H11A—C11—H11B | 107.6 |
C10—C1—H1A | 108.3 | C13—C12—C11 | 109.30 (19) |
C2—C1—H1B | 108.3 | C13—C12—H12A | 109.8 |
C10—C1—H1B | 108.3 | C11—C12—H12A | 109.8 |
H1A—C1—H1B | 107.4 | C13—C12—H12B | 109.8 |
C3—C2—C1 | 107.6 (2) | C11—C12—H12B | 109.8 |
C3—C2—H2A | 110.2 | H12A—C12—H12B | 108.3 |
C1—C2—H2A | 110.2 | C12—C13—C17 | 116.9 (2) |
C3—C2—H2B | 110.2 | C12—C13—C14 | 105.38 (17) |
C1—C2—H2B | 110.2 | C17—C13—C14 | 99.58 (19) |
H2A—C2—H2B | 108.5 | C12—C13—C18 | 108.8 (2) |
O1—C3—C2 | 109.3 (2) | C17—C13—C18 | 107.83 (19) |
O1—C3—C4 | 109.5 (2) | C14—C13—C18 | 118.5 (2) |
C2—C3—C4 | 110.1 (2) | C15—C14—C8 | 121.7 (2) |
O1—C3—H3 | 109.3 | C15—C14—C13 | 107.47 (19) |
C2—C3—H3 | 109.3 | C8—C14—C13 | 112.94 (19) |
C4—C3—H3 | 109.3 | C15—C14—H14 | 104.3 |
C3—C4—C5 | 110.7 (2) | C8—C14—H14 | 104.3 |
C3—C4—H4A | 109.5 | C13—C14—H14 | 104.3 |
C5—C4—H4A | 109.5 | C20—C15—C14 | 121.7 (3) |
C3—C4—H4B | 109.5 | C20—C15—C16 | 60.4 (2) |
C5—C4—H4B | 109.5 | C14—C15—C16 | 105.4 (2) |
H4A—C4—H4B | 108.1 | C20—C15—H15 | 117.9 |
O3—C5—C6 | 58.59 (17) | C14—C15—H15 | 117.9 |
O3—C5—C4 | 111.16 (19) | C16—C15—H15 | 117.9 |
C6—C5—C4 | 117.2 (2) | C17—C16—C20 | 119.6 (3) |
O3—C5—C10 | 114.93 (17) | C17—C16—C15 | 106.1 (2) |
C6—C5—C10 | 122.2 (2) | C20—C16—C15 | 58.0 (2) |
C4—C5—C10 | 117.4 (2) | C17—C16—H16 | 118.8 |
O3—C6—C5 | 60.61 (16) | C20—C16—H16 | 118.8 |
O3—C6—C7 | 114.2 (2) | C15—C16—H16 | 118.8 |
C5—C6—C7 | 121.2 (2) | O4—C17—C16 | 124.6 (3) |
O3—C6—H6 | 116.3 | O4—C17—C13 | 125.8 (3) |
C5—C6—H6 | 116.3 | C16—C17—C13 | 109.4 (2) |
C7—C6—H6 | 116.3 | C13—C18—H18A | 109.5 |
C6—C7—C8 | 112.3 (2) | C13—C18—H18B | 109.5 |
C6—C7—Cl1 | 105.87 (18) | H18A—C18—H18B | 109.5 |
C8—C7—Cl1 | 111.72 (17) | C13—C18—H18C | 109.5 |
C6—C7—H7 | 109.0 | H18A—C18—H18C | 109.5 |
C8—C7—H7 | 109.0 | H18B—C18—H18C | 109.5 |
Cl1—C7—H7 | 109.0 | C10—C19—H19A | 109.5 |
C7—C8—C14 | 111.83 (18) | C10—C19—H19B | 109.5 |
C7—C8—C9 | 110.61 (16) | H19A—C19—H19B | 109.5 |
C14—C8—C9 | 107.59 (19) | C10—C19—H19C | 109.5 |
C7—C8—H8 | 108.9 | H19A—C19—H19C | 109.5 |
C14—C8—H8 | 108.9 | H19B—C19—H19C | 109.5 |
C9—C8—H8 | 108.9 | C15—C20—C16 | 61.6 (2) |
C8—C9—C11 | 112.13 (17) | C15—C20—H20A | 117.6 |
C8—C9—C10 | 115.31 (17) | C16—C20—H20A | 117.6 |
C11—C9—C10 | 112.89 (18) | C15—C20—H20B | 117.6 |
C8—C9—H9 | 105.1 | C16—C20—H20B | 117.6 |
C11—C9—H9 | 105.1 | H20A—C20—H20B | 114.7 |
C10—C9—H9 | 105.1 | O2—C21—O1 | 122.7 (3) |
C19—C10—C5 | 106.5 (2) | O2—C21—C22 | 124.5 (3) |
C19—C10—C1 | 109.7 (2) | O1—C21—C22 | 112.8 (3) |
C5—C10—C1 | 108.93 (17) | C21—C22—H22A | 109.5 |
C19—C10—C9 | 112.55 (18) | C21—C22—H22B | 109.5 |
C5—C10—C9 | 112.40 (17) | H22A—C22—H22B | 109.5 |
C1—C10—C9 | 106.71 (17) | C21—C22—H22C | 109.5 |
C12—C11—C9 | 114.39 (19) | H22A—C22—H22C | 109.5 |
C12—C11—H11A | 108.7 | H22B—C22—H22C | 109.5 |
| | | |
C10—C1—C2—C3 | −57.7 (3) | C11—C9—C10—C19 | −39.8 (3) |
C21—O1—C3—C2 | 132.3 (3) | C8—C9—C10—C5 | −29.4 (2) |
C21—O1—C3—C4 | −107.0 (3) | C11—C9—C10—C5 | −160.07 (18) |
C1—C2—C3—O1 | −175.8 (2) | C8—C9—C10—C1 | −148.74 (18) |
C1—C2—C3—C4 | 63.9 (3) | C11—C9—C10—C1 | 80.6 (2) |
O1—C3—C4—C5 | 179.4 (2) | C8—C9—C11—C12 | 48.9 (3) |
C2—C3—C4—C5 | −60.4 (3) | C10—C9—C11—C12 | −178.82 (19) |
C6—O3—C5—C4 | 109.7 (2) | C9—C11—C12—C13 | −54.7 (3) |
C6—O3—C5—C10 | −113.9 (2) | C11—C12—C13—C17 | 170.1 (2) |
C3—C4—C5—O3 | −175.8 (2) | C11—C12—C13—C14 | 60.6 (2) |
C3—C4—C5—C6 | −111.3 (3) | C11—C12—C13—C18 | −67.5 (2) |
C3—C4—C5—C10 | 49.0 (3) | C7—C8—C14—C15 | −46.4 (3) |
C5—O3—C6—C7 | 113.5 (2) | C9—C8—C14—C15 | −168.1 (2) |
C4—C5—C6—O3 | −99.3 (2) | C7—C8—C14—C13 | −176.50 (18) |
C10—C5—C6—O3 | 101.5 (2) | C9—C8—C14—C13 | 61.8 (2) |
O3—C5—C6—C7 | −102.1 (3) | C12—C13—C14—C15 | 155.1 (2) |
C4—C5—C6—C7 | 158.6 (2) | C17—C13—C14—C15 | 33.6 (3) |
C10—C5—C6—C7 | −0.6 (4) | C18—C13—C14—C15 | −82.9 (3) |
O3—C6—C7—C8 | −41.6 (3) | C12—C13—C14—C8 | −67.9 (2) |
C5—C6—C7—C8 | 27.5 (4) | C17—C13—C14—C8 | 170.5 (2) |
O3—C6—C7—Cl1 | −163.72 (17) | C18—C13—C14—C8 | 54.1 (3) |
C5—C6—C7—Cl1 | −94.6 (3) | C8—C14—C15—C20 | −91.6 (3) |
C6—C7—C8—C14 | −174.1 (2) | C13—C14—C15—C20 | 40.8 (3) |
Cl1—C7—C8—C14 | −55.3 (2) | C8—C14—C15—C16 | −156.0 (2) |
C6—C7—C8—C9 | −54.2 (3) | C13—C14—C15—C16 | −23.6 (3) |
Cl1—C7—C8—C9 | 64.6 (2) | C20—C15—C16—C17 | −115.2 (3) |
C7—C8—C9—C11 | −172.1 (2) | C14—C15—C16—C17 | 2.9 (3) |
C14—C8—C9—C11 | −49.7 (2) | C14—C15—C16—C20 | 118.1 (3) |
C7—C8—C9—C10 | 56.8 (3) | C20—C16—C17—O4 | 141.8 (3) |
C14—C8—C9—C10 | 179.26 (17) | C15—C16—C17—O4 | −156.3 (3) |
O3—C5—C10—C19 | −55.1 (2) | C20—C16—C17—C13 | −42.8 (4) |
C6—C5—C10—C19 | −122.4 (3) | C15—C16—C17—C13 | 19.1 (3) |
C4—C5—C10—C19 | 78.4 (2) | C12—C13—C17—O4 | 30.2 (4) |
O3—C5—C10—C1 | −173.4 (2) | C14—C13—C17—O4 | 143.0 (3) |
C6—C5—C10—C1 | 119.4 (2) | C18—C13—C17—O4 | −92.7 (3) |
C4—C5—C10—C1 | −39.8 (3) | C12—C13—C17—C16 | −145.1 (3) |
O3—C5—C10—C9 | 68.6 (2) | C14—C13—C17—C16 | −32.3 (3) |
C6—C5—C10—C9 | 1.3 (3) | C18—C13—C17—C16 | 92.0 (3) |
C4—C5—C10—C9 | −157.9 (2) | C14—C15—C20—C16 | −90.5 (3) |
C2—C1—C10—C19 | −71.8 (3) | C17—C16—C20—C15 | 91.2 (3) |
C2—C1—C10—C5 | 44.4 (3) | C3—O1—C21—O2 | 1.4 (5) |
C2—C1—C10—C9 | 166.0 (2) | C3—O1—C21—C22 | −175.8 (3) |
C8—C9—C10—C19 | 90.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3i | 0.97 | 2.59 | 3.480 (3) | 153 |
Symmetry code: (i) x, y+1, z. |