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In the title compound, C24H34O5, the cyclohexane rings adopt chair conformations while the cyclohexene ring is in a half-chair conformation. Both five-membered rings adopt envelope conformations.
Supporting information
CCDC reference: 618165
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.044
- wR factor = 0.120
- Data-to-parameter ratio = 8.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C23
PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3 ... ?
Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O4
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 25.18
From the CIF: _reflns_number_total 2165
Count of symmetry unique reflns 2163
Completeness (_total/calc) 100.09%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2
Fraction of Friedel pairs measured 0.001
Are heavy atom types Z>Si present no
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 C7 = . R
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
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
12 ALERT level G = General alerts; check
12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 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: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4, PSI and EAC in CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997)'; software used to prepare material for publication: SHELXL97.
3
β-Acetoxy-17,17-ethylenedioxy-15
β,16
β-methylene-5-androsten-7
β-ol
top
Crystal data top
C24H34O5 | F(000) = 872 |
Mr = 402.51 | Dx = 1.269 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.049 (3) Å | θ = 10.1–12.4° |
b = 11.550 (3) Å | µ = 0.09 mm−1 |
c = 18.149 (7) Å | T = 293 K |
V = 2106.5 (11) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.40 × 0.35 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.016 |
Radiation source: fine-focus sealed tube | θmax = 25.2°, θmin = 2.1° |
Graphite monochromator | h = 0→12 |
ω/2θ scans | k = 0→13 |
2307 measured reflections | l = −1→21 |
2165 independent reflections | 3 standard reflections every 60 min |
1415 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.9275P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
2165 reflections | Δρmax = 0.28 e Å−3 |
267 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0097 (11) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1826 (3) | 0.8400 (3) | 1.16673 (15) | 0.0536 (9) | |
O2 | 0.1020 (4) | 0.6696 (3) | 1.20524 (18) | 0.0674 (10) | |
O3 | 0.3316 (5) | 0.5116 (3) | 0.84835 (19) | 0.0739 (12) | |
H3 | 0.334 (7) | 0.487 (5) | 0.8059 (16) | 0.12 (3)* | |
O4 | 0.1531 (3) | 0.7986 (3) | 0.55417 (15) | 0.0537 (8) | |
O5 | −0.0167 (3) | 0.7075 (3) | 0.61390 (15) | 0.0553 (9) | |
C1 | 0.0961 (4) | 0.9030 (4) | 0.9701 (2) | 0.0473 (11) | |
H1A | 0.0854 | 0.9766 | 0.9450 | 0.057* | |
H1B | 0.0116 | 0.8626 | 0.9675 | 0.057* | |
C2 | 0.1290 (5) | 0.9263 (4) | 1.0509 (2) | 0.0497 (11) | |
H2A | 0.2098 | 0.9718 | 1.0544 | 0.060* | |
H2B | 0.0573 | 0.9697 | 1.0736 | 0.060* | |
C3 | 0.1472 (5) | 0.8137 (4) | 1.0902 (2) | 0.0454 (11) | |
H3A | 0.0638 | 0.7698 | 1.0890 | 0.055* | |
C4 | 0.2568 (5) | 0.7430 (4) | 1.0557 (2) | 0.0480 (11) | |
H4A | 0.2626 | 0.6686 | 1.0803 | 0.058* | |
H4B | 0.3411 | 0.7826 | 1.0623 | 0.058* | |
C5 | 0.2320 (4) | 0.7241 (4) | 0.9739 (2) | 0.0405 (10) | |
C6 | 0.2394 (4) | 0.6192 (4) | 0.9448 (2) | 0.0464 (11) | |
H6 | 0.2541 | 0.5580 | 0.9770 | 0.056* | |
C7 | 0.2264 (5) | 0.5901 (3) | 0.8650 (2) | 0.0445 (11) | |
H7 | 0.1415 | 0.5499 | 0.8577 | 0.053* | |
C8 | 0.2275 (4) | 0.6975 (3) | 0.8165 (2) | 0.0349 (9) | |
H8 | 0.3195 | 0.7242 | 0.8107 | 0.042* | |
C9 | 0.1447 (4) | 0.7948 (3) | 0.8526 (2) | 0.0381 (10) | |
H9 | 0.0570 | 0.7610 | 0.8626 | 0.046* | |
C10 | 0.2016 (4) | 0.8313 (3) | 0.9291 (2) | 0.0353 (9) | |
C11 | 0.1193 (5) | 0.8983 (4) | 0.8021 (2) | 0.0508 (12) | |
H11A | 0.2013 | 0.9420 | 0.7973 | 0.061* | |
H11B | 0.0541 | 0.9484 | 0.8253 | 0.061* | |
C12 | 0.0695 (5) | 0.8664 (4) | 0.7247 (2) | 0.0530 (12) | |
H12A | −0.0178 | 0.8309 | 0.7280 | 0.064* | |
H12B | 0.0621 | 0.9357 | 0.6947 | 0.064* | |
C13 | 0.1677 (4) | 0.7820 (3) | 0.6893 (2) | 0.0399 (10) | |
C14 | 0.1686 (4) | 0.6741 (3) | 0.7402 (2) | 0.0377 (10) | |
H14 | 0.0744 | 0.6581 | 0.7496 | 0.045* | |
C15 | 0.2147 (4) | 0.5738 (4) | 0.6929 (2) | 0.0430 (11) | |
H15 | 0.1911 | 0.4951 | 0.7083 | 0.052* | |
C16 | 0.1869 (4) | 0.6089 (4) | 0.6141 (2) | 0.0465 (11) | |
H16 | 0.1472 | 0.5508 | 0.5814 | 0.056* | |
C17 | 0.1249 (4) | 0.7267 (4) | 0.6154 (2) | 0.0435 (10) | |
C18 | 0.3030 (5) | 0.8447 (4) | 0.6791 (3) | 0.0542 (13) | |
H18A | 0.3406 | 0.8239 | 0.6323 | 0.081* | |
H18B | 0.3627 | 0.8220 | 0.7178 | 0.081* | |
H18C | 0.2894 | 0.9269 | 0.6809 | 0.081* | |
C19 | 0.3289 (4) | 0.9040 (4) | 0.9207 (2) | 0.0486 (11) | |
H19A | 0.3763 | 0.9050 | 0.9666 | 0.073* | |
H19B | 0.3056 | 0.9818 | 0.9071 | 0.073* | |
H19C | 0.3842 | 0.8708 | 0.8831 | 0.073* | |
C20 | 0.1523 (5) | 0.7619 (4) | 1.2181 (2) | 0.0489 (11) | |
C21 | 0.1881 (5) | 0.8031 (5) | 1.2935 (2) | 0.0659 (14) | |
H21A | 0.1675 | 0.7438 | 1.3288 | 0.099* | |
H21B | 0.1383 | 0.8717 | 1.3048 | 0.099* | |
H21C | 0.2815 | 0.8201 | 1.2954 | 0.099* | |
C22 | 0.3268 (5) | 0.5888 (4) | 0.6398 (2) | 0.0535 (12) | |
H22A | 0.3718 | 0.5196 | 0.6225 | 0.064* | |
H22B | 0.3838 | 0.6559 | 0.6458 | 0.064* | |
C23 | 0.0453 (6) | 0.7955 (7) | 0.5068 (3) | 0.106 (3) | |
H23A | 0.0579 | 0.7368 | 0.4692 | 0.127* | |
H23B | 0.0332 | 0.8699 | 0.4829 | 0.127* | |
C24 | −0.0703 (5) | 0.7675 (5) | 0.5534 (3) | 0.0755 (16) | |
H24A | −0.1152 | 0.8374 | 0.5694 | 0.091* | |
H24B | −0.1332 | 0.7193 | 0.5268 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.070 (2) | 0.0599 (18) | 0.0312 (16) | −0.0141 (18) | 0.0041 (16) | −0.0075 (15) |
O2 | 0.090 (3) | 0.062 (2) | 0.050 (2) | −0.016 (2) | 0.0048 (19) | −0.0033 (19) |
O3 | 0.118 (3) | 0.055 (2) | 0.049 (2) | 0.037 (2) | −0.017 (2) | −0.0133 (17) |
O4 | 0.0585 (19) | 0.074 (2) | 0.0285 (15) | −0.0093 (17) | −0.0023 (15) | 0.0107 (16) |
O5 | 0.0428 (17) | 0.086 (2) | 0.0369 (16) | −0.0057 (16) | −0.0074 (15) | −0.0011 (18) |
C1 | 0.054 (3) | 0.053 (3) | 0.034 (2) | 0.006 (2) | −0.007 (2) | −0.007 (2) |
C2 | 0.054 (3) | 0.057 (3) | 0.038 (2) | 0.010 (2) | 0.000 (2) | −0.013 (2) |
C3 | 0.054 (3) | 0.055 (3) | 0.027 (2) | −0.009 (2) | 0.000 (2) | −0.013 (2) |
C4 | 0.059 (3) | 0.047 (2) | 0.038 (2) | 0.002 (2) | −0.006 (2) | −0.001 (2) |
C5 | 0.046 (2) | 0.045 (2) | 0.030 (2) | 0.000 (2) | −0.003 (2) | −0.001 (2) |
C6 | 0.060 (3) | 0.042 (2) | 0.037 (2) | 0.000 (2) | −0.008 (2) | 0.005 (2) |
C7 | 0.059 (3) | 0.036 (2) | 0.038 (2) | −0.003 (2) | −0.006 (2) | −0.006 (2) |
C8 | 0.037 (2) | 0.038 (2) | 0.030 (2) | −0.0016 (19) | −0.0043 (18) | −0.0024 (19) |
C9 | 0.038 (2) | 0.043 (2) | 0.033 (2) | −0.002 (2) | −0.0017 (18) | −0.0027 (19) |
C10 | 0.038 (2) | 0.040 (2) | 0.028 (2) | 0.0004 (19) | −0.0008 (18) | −0.0049 (19) |
C11 | 0.066 (3) | 0.047 (3) | 0.039 (2) | 0.019 (2) | −0.012 (2) | −0.007 (2) |
C12 | 0.066 (3) | 0.053 (3) | 0.040 (2) | 0.016 (2) | −0.011 (2) | −0.002 (2) |
C13 | 0.043 (2) | 0.042 (2) | 0.035 (2) | 0.000 (2) | −0.006 (2) | 0.002 (2) |
C14 | 0.036 (2) | 0.043 (2) | 0.034 (2) | −0.005 (2) | 0.0004 (19) | −0.001 (2) |
C15 | 0.048 (2) | 0.043 (2) | 0.038 (2) | −0.002 (2) | −0.001 (2) | −0.003 (2) |
C16 | 0.050 (3) | 0.055 (3) | 0.034 (2) | −0.004 (2) | 0.001 (2) | −0.007 (2) |
C17 | 0.039 (2) | 0.059 (3) | 0.032 (2) | −0.009 (2) | −0.002 (2) | −0.001 (2) |
C18 | 0.063 (3) | 0.052 (3) | 0.048 (3) | −0.013 (2) | −0.013 (3) | 0.008 (2) |
C19 | 0.055 (3) | 0.049 (2) | 0.041 (2) | −0.004 (2) | −0.004 (2) | −0.001 (2) |
C20 | 0.049 (3) | 0.057 (3) | 0.041 (3) | 0.003 (2) | 0.006 (2) | −0.005 (2) |
C21 | 0.082 (4) | 0.083 (3) | 0.033 (2) | −0.005 (3) | 0.001 (3) | −0.008 (3) |
C22 | 0.052 (3) | 0.056 (3) | 0.053 (3) | 0.004 (2) | 0.002 (2) | −0.006 (2) |
C23 | 0.087 (4) | 0.171 (7) | 0.061 (3) | −0.025 (5) | −0.030 (4) | 0.045 (5) |
C24 | 0.062 (3) | 0.104 (4) | 0.061 (3) | 0.000 (3) | −0.017 (3) | 0.019 (3) |
Geometric parameters (Å, º) top
O1—C20 | 1.332 (5) | C11—C12 | 1.536 (6) |
O1—C3 | 1.466 (5) | C11—H11A | 0.97 |
O2—C20 | 1.203 (5) | C11—H11B | 0.97 |
O3—C7 | 1.426 (6) | C12—C13 | 1.529 (6) |
O3—H3 | 0.82 (2) | C12—H12A | 0.97 |
O4—C23 | 1.384 (6) | C12—H12B | 0.97 |
O4—C17 | 1.417 (5) | C13—C17 | 1.546 (6) |
O5—C24 | 1.406 (5) | C13—C18 | 1.551 (6) |
O5—C17 | 1.441 (5) | C13—C14 | 1.551 (5) |
C1—C2 | 1.527 (5) | C14—C15 | 1.515 (5) |
C1—C10 | 1.538 (5) | C14—H14 | 0.98 |
C1—H1A | 0.97 | C15—C22 | 1.493 (6) |
C1—H1B | 0.97 | C15—C16 | 1.512 (6) |
C2—C3 | 1.494 (6) | C15—H15 | 0.98 |
C2—H2A | 0.97 | C16—C17 | 1.496 (6) |
C2—H2B | 0.97 | C16—C22 | 1.500 (6) |
C3—C4 | 1.508 (6) | C16—H16 | 0.98 |
C3—H3A | 0.98 | C18—H18A | 0.96 |
C4—C5 | 1.520 (5) | C18—H18B | 0.96 |
C4—H4A | 0.97 | C18—H18C | 0.96 |
C4—H4B | 0.97 | C19—H19A | 0.96 |
C5—C6 | 1.323 (5) | C19—H19B | 0.96 |
C5—C10 | 1.514 (6) | C19—H19C | 0.96 |
C6—C7 | 1.492 (6) | C20—C21 | 1.493 (6) |
C6—H6 | 0.93 | C21—H21A | 0.96 |
C7—C8 | 1.522 (5) | C21—H21B | 0.96 |
C7—H7 | 0.98 | C21—H21C | 0.96 |
C8—C14 | 1.529 (5) | C22—H22A | 0.97 |
C8—C9 | 1.545 (5) | C22—H22B | 0.97 |
C8—H8 | 0.98 | C23—C24 | 1.473 (8) |
C9—C11 | 1.528 (6) | C23—H23A | 0.97 |
C9—C10 | 1.559 (5) | C23—H23B | 0.97 |
C9—H9 | 0.98 | C24—H24A | 0.97 |
C10—C19 | 1.538 (6) | C24—H24B | 0.97 |
| | | |
C20—O1—C3 | 117.9 (3) | C12—C13—C17 | 116.7 (3) |
C7—O3—H3 | 116 (5) | C12—C13—C18 | 108.5 (3) |
C23—O4—C17 | 108.4 (4) | C17—C13—C18 | 109.5 (3) |
C24—O5—C17 | 108.5 (4) | C12—C13—C14 | 105.4 (3) |
C2—C1—C10 | 114.3 (4) | C17—C13—C14 | 100.7 (3) |
C2—C1—H1A | 108.7 | C18—C13—C14 | 116.1 (3) |
C10—C1—H1A | 108.7 | C15—C14—C8 | 122.1 (3) |
C2—C1—H1B | 108.7 | C15—C14—C13 | 106.1 (3) |
C10—C1—H1B | 108.7 | C8—C14—C13 | 113.5 (3) |
H1A—C1—H1B | 107.6 | C15—C14—H14 | 104.5 |
C3—C2—C1 | 109.4 (4) | C8—C14—H14 | 104.5 |
C3—C2—H2A | 109.8 | C13—C14—H14 | 104.5 |
C1—C2—H2A | 109.8 | C22—C15—C16 | 59.9 (3) |
C3—C2—H2B | 109.8 | C22—C15—C14 | 120.6 (4) |
C1—C2—H2B | 109.8 | C16—C15—C14 | 106.0 (3) |
H2A—C2—H2B | 108.2 | C22—C15—H15 | 118.3 |
O1—C3—C2 | 107.6 (3) | C16—C15—H15 | 118.3 |
O1—C3—C4 | 109.2 (4) | C14—C15—H15 | 118.3 |
C2—C3—C4 | 111.3 (4) | C17—C16—C22 | 121.7 (4) |
O1—C3—H3A | 109.6 | C17—C16—C15 | 107.7 (3) |
C2—C3—H3A | 109.6 | C22—C16—C15 | 59.4 (3) |
C4—C3—H3A | 109.6 | C17—C16—H16 | 117.6 |
C3—C4—C5 | 111.3 (4) | C22—C16—H16 | 117.6 |
C3—C4—H4A | 109.4 | C15—C16—H16 | 117.6 |
C5—C4—H4A | 109.4 | O4—C17—O5 | 105.8 (3) |
C3—C4—H4B | 109.4 | O4—C17—C16 | 115.9 (3) |
C5—C4—H4B | 109.4 | O5—C17—C16 | 105.7 (4) |
H4A—C4—H4B | 108.0 | O4—C17—C13 | 112.5 (3) |
C6—C5—C10 | 123.0 (4) | O5—C17—C13 | 110.8 (3) |
C6—C5—C4 | 120.9 (4) | C16—C17—C13 | 105.9 (3) |
C10—C5—C4 | 116.1 (3) | C13—C18—H18A | 109.5 |
C5—C6—C7 | 126.1 (4) | C13—C18—H18B | 109.5 |
C5—C6—H6 | 116.9 | H18A—C18—H18B | 109.5 |
C7—C6—H6 | 116.9 | C13—C18—H18C | 109.5 |
O3—C7—C6 | 106.5 (4) | H18A—C18—H18C | 109.5 |
O3—C7—C8 | 113.0 (4) | H18B—C18—H18C | 109.5 |
C6—C7—C8 | 112.2 (3) | C10—C19—H19A | 109.5 |
O3—C7—H7 | 108.4 | C10—C19—H19B | 109.5 |
C6—C7—H7 | 108.4 | H19A—C19—H19B | 109.5 |
C8—C7—H7 | 108.4 | C10—C19—H19C | 109.5 |
C7—C8—C14 | 112.1 (3) | H19A—C19—H19C | 109.5 |
C7—C8—C9 | 110.1 (3) | H19B—C19—H19C | 109.5 |
C14—C8—C9 | 107.7 (3) | O2—C20—O1 | 124.1 (4) |
C7—C8—H8 | 109.0 | O2—C20—C21 | 124.1 (5) |
C14—C8—H8 | 109.0 | O1—C20—C21 | 111.8 (4) |
C9—C8—H8 | 109.0 | C20—C21—H21A | 109.5 |
C11—C9—C8 | 113.8 (3) | C20—C21—H21B | 109.5 |
C11—C9—C10 | 112.6 (3) | H21A—C21—H21B | 109.5 |
C8—C9—C10 | 112.2 (3) | C20—C21—H21C | 109.5 |
C11—C9—H9 | 105.8 | H21A—C21—H21C | 109.5 |
C8—C9—H9 | 105.8 | H21B—C21—H21C | 109.5 |
C10—C9—H9 | 105.8 | C15—C22—C16 | 60.7 (3) |
C5—C10—C1 | 108.6 (3) | C15—C22—H22A | 117.7 |
C5—C10—C19 | 109.4 (3) | C16—C22—H22A | 117.7 |
C1—C10—C19 | 109.1 (3) | C15—C22—H22B | 117.7 |
C5—C10—C9 | 109.4 (3) | C16—C22—H22B | 117.7 |
C1—C10—C9 | 108.9 (3) | H22A—C22—H22B | 114.8 |
C19—C10—C9 | 111.4 (3) | O4—C23—C24 | 105.4 (4) |
C9—C11—C12 | 114.5 (4) | O4—C23—H23A | 110.7 |
C9—C11—H11A | 108.6 | C24—C23—H23A | 110.7 |
C12—C11—H11A | 108.6 | O4—C23—H23B | 110.7 |
C9—C11—H11B | 108.6 | C24—C23—H23B | 110.7 |
C12—C11—H11B | 108.6 | H23A—C23—H23B | 108.8 |
H11A—C11—H11B | 107.6 | O5—C24—C23 | 104.8 (4) |
C13—C12—C11 | 109.1 (4) | O5—C24—H24A | 110.8 |
C13—C12—H12A | 109.9 | C23—C24—H24A | 110.8 |
C11—C12—H12A | 109.9 | O5—C24—H24B | 110.8 |
C13—C12—H12B | 109.9 | C23—C24—H24B | 110.8 |
C11—C12—H12B | 109.9 | H24A—C24—H24B | 108.9 |
H12A—C12—H12B | 108.3 | | |
| | | |
C10—C1—C2—C3 | −57.8 (5) | C7—C8—C14—C13 | 179.8 (3) |
C20—O1—C3—C2 | 153.4 (4) | C9—C8—C14—C13 | 58.5 (4) |
C20—O1—C3—C4 | −85.7 (4) | C12—C13—C14—C15 | 156.5 (3) |
C1—C2—C3—O1 | 178.3 (3) | C17—C13—C14—C15 | 34.8 (4) |
C1—C2—C3—C4 | 58.7 (5) | C18—C13—C14—C15 | −83.3 (4) |
O1—C3—C4—C5 | −174.0 (4) | C12—C13—C14—C8 | −66.7 (4) |
C2—C3—C4—C5 | −55.5 (5) | C17—C13—C14—C8 | 171.6 (3) |
C3—C4—C5—C6 | −130.2 (5) | C18—C13—C14—C8 | 53.5 (5) |
C3—C4—C5—C10 | 50.9 (5) | C8—C14—C15—C22 | −90.1 (5) |
C10—C5—C6—C7 | 3.2 (8) | C13—C14—C15—C22 | 42.0 (5) |
C4—C5—C6—C7 | −175.6 (4) | C8—C14—C15—C16 | −154.2 (4) |
C5—C6—C7—O3 | 134.3 (5) | C13—C14—C15—C16 | −22.0 (4) |
C5—C6—C7—C8 | 10.2 (7) | C22—C15—C16—C17 | −116.9 (4) |
O3—C7—C8—C14 | 78.9 (4) | C14—C15—C16—C17 | −0.4 (4) |
C6—C7—C8—C14 | −160.7 (4) | C14—C15—C16—C22 | 116.5 (4) |
O3—C7—C8—C9 | −161.2 (3) | C23—O4—C17—O5 | −16.4 (5) |
C6—C7—C8—C9 | −40.8 (5) | C23—O4—C17—C16 | 100.4 (5) |
C7—C8—C9—C11 | −169.7 (3) | C23—O4—C17—C13 | −137.5 (5) |
C14—C8—C9—C11 | −47.2 (4) | C24—O5—C17—O4 | −0.3 (5) |
C7—C8—C9—C10 | 61.0 (4) | C24—O5—C17—C16 | −123.8 (4) |
C14—C8—C9—C10 | −176.4 (3) | C24—O5—C17—C13 | 121.8 (4) |
C6—C5—C10—C1 | 133.9 (5) | C22—C16—C17—O4 | 83.8 (5) |
C4—C5—C10—C1 | −47.2 (5) | C15—C16—C17—O4 | 148.3 (3) |
C6—C5—C10—C19 | −107.1 (5) | C22—C16—C17—O5 | −159.3 (4) |
C4—C5—C10—C19 | 71.8 (5) | C15—C16—C17—O5 | −94.8 (4) |
C6—C5—C10—C9 | 15.1 (6) | C22—C16—C17—C13 | −41.7 (5) |
C4—C5—C10—C9 | −166.0 (3) | C15—C16—C17—C13 | 22.8 (4) |
C2—C1—C10—C5 | 50.6 (5) | C12—C13—C17—O4 | 84.0 (4) |
C2—C1—C10—C19 | −68.5 (5) | C18—C13—C17—O4 | −39.7 (4) |
C2—C1—C10—C9 | 169.7 (4) | C14—C13—C17—O4 | −162.6 (3) |
C11—C9—C10—C5 | −176.5 (3) | C12—C13—C17—O5 | −34.2 (5) |
C8—C9—C10—C5 | −46.6 (4) | C18—C13—C17—O5 | −157.9 (3) |
C11—C9—C10—C1 | 64.9 (4) | C14—C13—C17—O5 | 79.2 (4) |
C8—C9—C10—C1 | −165.1 (3) | C12—C13—C17—C16 | −148.4 (4) |
C11—C9—C10—C19 | −55.4 (5) | C18—C13—C17—C16 | 87.9 (4) |
C8—C9—C10—C19 | 74.5 (4) | C14—C13—C17—C16 | −35.0 (4) |
C8—C9—C11—C12 | 48.1 (5) | C3—O1—C20—O2 | 2.7 (7) |
C10—C9—C11—C12 | 177.2 (4) | C3—O1—C20—C21 | −177.1 (4) |
C9—C11—C12—C13 | −55.2 (5) | C14—C15—C22—C16 | −91.5 (4) |
C11—C12—C13—C17 | 171.8 (4) | C17—C16—C22—C15 | 92.9 (4) |
C11—C12—C13—C18 | −64.0 (4) | C17—O4—C23—C24 | 26.1 (7) |
C11—C12—C13—C14 | 61.0 (4) | C17—O5—C24—C23 | 15.6 (6) |
C7—C8—C14—C15 | −51.1 (5) | O4—C23—C24—O5 | −25.6 (7) |
C9—C8—C14—C15 | −172.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12A···O5 | 0.97 | 2.51 | 2.857 (5) | 101 |
C18—H18A···O4 | 0.96 | 2.38 | 2.774 (6) | 104 |
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