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In agatholic acid, C
20H
32O
3, the two molecules in the asymmetric unit have essentially the same conformation. The molecules are linked by O—H
O hydrogen bonds between the carboxyl and alcohol groups.
Supporting information
CCDC reference: 203019
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.010 Å
- R factor = 0.051
- wR factor = 0.126
- Data-to-parameter ratio = 6.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5389
| Author response: The diffraction of the crystal is very weak. Data were initially collected
to 55\% 2\T, however significant diffraction was only observed to 45\% and
the higher angle data was discarded.
|
Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a
non-centrosymmetric structure, where ZMAX < 18
sine(theta)/lambda 0.5389
Proportion of unique data used 1.0000
Ratio reflections to parameters 6.1575
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.114
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 22.52
From the CIF: _reflns_number_total 2580
Count of symmetry unique reflns 2581
Completeness (_total/calc) 99.96%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
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.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C20H32O3 | F(000) = 704 |
Mr = 320.46 | Dx = 1.118 Mg m−3 |
Monoclinic, P21 | Melting point: 457 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7955 (14) Å | Cell parameters from 2540 reflections |
b = 23.362 (4) Å | θ = 2.6–22.5° |
c = 10.6973 (19) Å | µ = 0.07 mm−1 |
β = 102.297 (3)° | T = 170 K |
V = 1903.4 (6) Å3 | Plate, white |
Z = 4 | 0.5 × 0.4 × 0.2 mm |
Data collection top
Bruker SMART CCD diffractometer | 1596 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.114 |
Graphite monochromator | θmax = 22.5°, θmin = 1.7° |
φ and ω scans | h = −8→8 |
15289 measured reflections | k = −25→25 |
2580 independent reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3 |
2580 reflections | (Δ/σ)max = 0.002 |
419 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.21 e Å−3 |
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 | |
O1 | 0.8190 (6) | 0.46434 (18) | 0.7794 (5) | 0.0457 (13) | |
H1 | 0.9179 | 0.4544 | 0.7676 | 0.055* | |
O1A | 1.9039 (6) | −0.01527 (18) | 0.9524 (5) | 0.0466 (13) | |
H1A | 2.0064 | −0.0266 | 0.9533 | 0.056* | |
C1A | 1.4799 (8) | 0.1313 (3) | 0.7735 (7) | 0.0389 (18) | |
H11A | 1.4122 | 0.1569 | 0.8188 | 0.047* | |
H12A | 1.4182 | 0.1300 | 0.6825 | 0.047* | |
C1 | 0.4313 (9) | 0.6301 (3) | 0.7329 (7) | 0.048 (2) | |
H11 | 0.3667 | 0.6456 | 0.7956 | 0.058* | |
H12 | 0.3722 | 0.6440 | 0.6472 | 0.058* | |
O2 | 0.2725 (7) | 0.8886 (2) | 1.0716 (5) | 0.0591 (15) | |
H32 | 0.2394 | 0.9166 | 1.1096 | 0.071* | |
O2A | 1.2691 (8) | 0.4113 (3) | 0.9391 (5) | 0.0749 (18) | |
H32A | 1.2120 | 0.4388 | 0.9604 | 0.090* | |
C2 | 0.4199 (9) | 0.5646 (3) | 0.7342 (8) | 0.051 (2) | |
H9 | 0.4661 | 0.5505 | 0.8222 | 0.061* | |
H10 | 0.2953 | 0.5528 | 0.7086 | 0.061* | |
C2A | 1.4801 (9) | 0.0711 (3) | 0.8300 (7) | 0.048 (2) | |
H9A | 1.5292 | 0.0727 | 0.9232 | 0.058* | |
H10A | 1.3579 | 0.0569 | 0.8169 | 0.058* | |
O3A | 1.1411 (7) | 0.4412 (2) | 0.7440 (5) | 0.0646 (16) | |
O3 | 0.2128 (7) | 0.9484 (2) | 0.9067 (5) | 0.0623 (16) | |
C3A | 1.5875 (9) | 0.0298 (3) | 0.7685 (7) | 0.046 (2) | |
H7A | 1.5288 | 0.0245 | 0.6776 | 0.056* | |
H8A | 1.5899 | −0.0079 | 0.8113 | 0.056* | |
C3 | 0.5224 (9) | 0.5378 (3) | 0.6448 (7) | 0.054 (2) | |
H7 | 0.4672 | 0.5485 | 0.5559 | 0.064* | |
H8 | 0.5156 | 0.4956 | 0.6516 | 0.064* | |
C4A | 1.7768 (9) | 0.0495 (3) | 0.7752 (7) | 0.0377 (18) | |
C4 | 0.7164 (9) | 0.5557 (3) | 0.6722 (6) | 0.0417 (19) | |
C5A | 1.7754 (8) | 0.1124 (3) | 0.7261 (6) | 0.0332 (17) | |
H16A | 1.7153 | 0.1096 | 0.6339 | 0.040* | |
C5 | 0.7296 (8) | 0.6219 (3) | 0.6800 (6) | 0.0364 (18) | |
H16 | 0.6759 | 0.6348 | 0.5911 | 0.044* | |
C6 | 0.9177 (9) | 0.6440 (3) | 0.7022 (7) | 0.050 (2) | |
H17 | 0.9821 | 0.6235 | 0.6455 | 0.060* | |
H18 | 0.9782 | 0.6368 | 0.7919 | 0.060* | |
C6A | 1.9571 (8) | 0.1357 (3) | 0.7217 (7) | 0.0433 (19) | |
H17A | 2.0227 | 0.1067 | 0.6831 | 0.052* | |
H18A | 2.0233 | 0.1433 | 0.8099 | 0.052* | |
C7A | 1.9415 (9) | 0.1908 (3) | 0.6434 (8) | 0.053 (2) | |
H19A | 2.0598 | 0.2074 | 0.6489 | 0.063* | |
H20A | 1.8912 | 0.1820 | 0.5524 | 0.063* | |
C7 | 0.9176 (10) | 0.7091 (3) | 0.6741 (9) | 0.062 (2) | |
H19 | 1.0393 | 0.7238 | 0.6975 | 0.074* | |
H20 | 0.8737 | 0.7156 | 0.5813 | 0.074* | |
C8 | 0.8038 (10) | 0.7417 (3) | 0.7480 (8) | 0.052 (2) | |
C8A | 1.8267 (9) | 0.2339 (3) | 0.6908 (7) | 0.0424 (19) | |
C9A | 1.6482 (8) | 0.2120 (3) | 0.6970 (7) | 0.0355 (18) | |
H23A | 1.5921 | 0.1996 | 0.6082 | 0.043* | |
C9 | 0.6166 (9) | 0.7181 (3) | 0.7271 (7) | 0.0389 (18) | |
H23 | 0.5675 | 0.7199 | 0.6329 | 0.047* | |
C10A | 1.6631 (8) | 0.1572 (3) | 0.7817 (6) | 0.0333 (17) | |
C10 | 0.6199 (9) | 0.6534 (3) | 0.7645 (6) | 0.0375 (18) | |
C11A | 1.5287 (9) | 0.2591 (3) | 0.7332 (7) | 0.0404 (18) | |
H24A | 1.4307 | 0.2409 | 0.7639 | 0.049* | |
H25A | 1.5971 | 0.2821 | 0.8044 | 0.049* | |
C11 | 0.4981 (10) | 0.7556 (3) | 0.7896 (7) | 0.0445 (19) | |
H24 | 0.5635 | 0.7685 | 0.8746 | 0.053* | |
H25 | 0.3955 | 0.7331 | 0.8020 | 0.053* | |
C12 | 0.4357 (10) | 0.8076 (3) | 0.7056 (7) | 0.049 (2) | |
H26 | 0.5389 | 0.8241 | 0.6785 | 0.058* | |
H27 | 0.3543 | 0.7938 | 0.6275 | 0.058* | |
C12A | 1.4541 (9) | 0.2985 (3) | 0.6226 (7) | 0.046 (2) | |
H26A | 1.5531 | 0.3136 | 0.5879 | 0.056* | |
H27A | 1.3802 | 0.2753 | 0.5543 | 0.056* | |
C13 | 0.3446 (9) | 0.8557 (3) | 0.7616 (7) | 0.0413 (19) | |
C13A | 1.3458 (9) | 0.3488 (3) | 0.6504 (7) | 0.0386 (18) | |
C14A | 1.3361 (9) | 0.3610 (3) | 0.7682 (8) | 0.046 (2) | |
H31A | 1.3990 | 0.3364 | 0.8327 | 0.055* | |
C14 | 0.3405 (9) | 0.8570 (3) | 0.8837 (8) | 0.047 (2) | |
H31 | 0.3892 | 0.8249 | 0.9332 | 0.057* | |
C15A | 1.2395 (10) | 0.4081 (3) | 0.8123 (9) | 0.050 (2) | |
C15 | 0.2692 (10) | 0.9025 (4) | 0.9521 (8) | 0.051 (2) | |
C16 | 0.2723 (10) | 0.9011 (3) | 0.6662 (7) | 0.062 (2) | |
H28 | 0.2137 | 0.9305 | 0.7074 | 0.093* | |
H29 | 0.1876 | 0.8839 | 0.5951 | 0.093* | |
H30 | 0.3683 | 0.9186 | 0.6335 | 0.093* | |
C16A | 1.2576 (12) | 0.3811 (4) | 0.5339 (8) | 0.083 (3) | |
H28A | 1.1929 | 0.4136 | 0.5591 | 0.125* | |
H29A | 1.1758 | 0.3557 | 0.4773 | 0.125* | |
H30A | 1.3462 | 0.3952 | 0.4888 | 0.125* | |
C17A | 1.8897 (10) | 0.2856 (4) | 0.7256 (9) | 0.079 (3) | |
H21A | 1.8192 | 0.3126 | 0.7580 | 0.095* | |
H22A | 2.0052 | 0.2955 | 0.7180 | 0.095* | |
C17 | 0.8671 (10) | 0.7847 (4) | 0.8199 (9) | 0.076 (3) | |
H21 | 0.9858 | 0.7960 | 0.8264 | 0.091* | |
H22 | 0.7948 | 0.8050 | 0.8659 | 0.091* | |
C18A | 1.8582 (10) | 0.0103 (3) | 0.6873 (7) | 0.050 (2) | |
H4A | 1.8621 | −0.0291 | 0.7190 | 0.076* | |
H5A | 1.9775 | 0.0233 | 0.6868 | 0.076* | |
H6A | 1.7865 | 0.0118 | 0.6001 | 0.076* | |
C18 | 0.7979 (10) | 0.5338 (3) | 0.5607 (7) | 0.056 (2) | |
H4 | 0.7372 | 0.5516 | 0.4804 | 0.083* | |
H5 | 0.7852 | 0.4921 | 0.5538 | 0.083* | |
H6 | 0.9227 | 0.5439 | 0.5774 | 0.083* | |
C19 | 0.8147 (9) | 0.5259 (3) | 0.7939 (7) | 0.0410 (19) | |
H2 | 0.9365 | 0.5406 | 0.8161 | 0.049* | |
H3 | 0.7571 | 0.5354 | 0.8653 | 0.049* | |
C19A | 1.8866 (9) | 0.0436 (3) | 0.9130 (7) | 0.0420 (19) | |
H2A | 2.0047 | 0.0601 | 0.9175 | 0.050* | |
H3A | 1.8295 | 0.0654 | 0.9723 | 0.050* | |
C20 | 0.6953 (9) | 0.6469 (3) | 0.9093 (6) | 0.0432 (19) | |
H13 | 0.6977 | 0.6063 | 0.9326 | 0.065* | |
H14 | 0.6212 | 0.6679 | 0.9571 | 0.065* | |
H15 | 0.8148 | 0.6624 | 0.9303 | 0.065* | |
C20A | 1.7399 (9) | 0.1748 (3) | 0.9231 (6) | 0.047 (2) | |
H13A | 1.7515 | 0.1408 | 0.9778 | 0.070* | |
H14A | 1.6610 | 0.2023 | 0.9512 | 0.070* | |
H15A | 1.8556 | 0.1924 | 0.9293 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.042 (3) | 0.037 (3) | 0.060 (4) | 0.007 (2) | 0.016 (3) | 0.002 (2) |
O1A | 0.043 (3) | 0.039 (3) | 0.060 (4) | 0.007 (2) | 0.017 (3) | 0.013 (3) |
C1A | 0.028 (4) | 0.035 (4) | 0.058 (5) | 0.002 (3) | 0.018 (4) | 0.006 (4) |
C1 | 0.040 (5) | 0.052 (5) | 0.053 (5) | −0.001 (4) | 0.012 (4) | 0.004 (4) |
O2 | 0.079 (4) | 0.051 (4) | 0.054 (4) | 0.023 (3) | 0.029 (3) | 0.003 (3) |
O2A | 0.088 (5) | 0.080 (5) | 0.054 (4) | 0.040 (3) | 0.008 (3) | −0.018 (3) |
C2 | 0.035 (4) | 0.040 (5) | 0.078 (6) | −0.004 (4) | 0.013 (4) | 0.002 (4) |
C2A | 0.038 (5) | 0.042 (5) | 0.067 (6) | 0.005 (4) | 0.019 (4) | 0.010 (4) |
O3A | 0.069 (4) | 0.059 (4) | 0.073 (4) | 0.022 (3) | 0.032 (3) | 0.005 (3) |
O3 | 0.076 (4) | 0.045 (4) | 0.071 (4) | 0.028 (3) | 0.025 (3) | 0.012 (3) |
C3A | 0.056 (5) | 0.029 (4) | 0.049 (5) | −0.004 (4) | 0.001 (4) | −0.002 (4) |
C3 | 0.036 (5) | 0.057 (5) | 0.063 (6) | 0.010 (4) | −0.001 (4) | −0.007 (4) |
C4A | 0.040 (5) | 0.034 (4) | 0.041 (5) | 0.005 (3) | 0.013 (4) | −0.003 (3) |
C4 | 0.049 (5) | 0.046 (5) | 0.030 (4) | 0.004 (4) | 0.005 (4) | −0.003 (4) |
C5A | 0.035 (4) | 0.031 (4) | 0.036 (4) | 0.006 (3) | 0.015 (3) | −0.003 (3) |
C5 | 0.043 (4) | 0.035 (4) | 0.035 (4) | 0.017 (3) | 0.017 (3) | 0.003 (3) |
C6 | 0.041 (5) | 0.051 (5) | 0.064 (6) | 0.009 (4) | 0.028 (4) | 0.006 (4) |
C6A | 0.037 (5) | 0.044 (5) | 0.054 (5) | 0.009 (4) | 0.022 (4) | 0.007 (4) |
C7A | 0.040 (4) | 0.052 (5) | 0.072 (6) | 0.000 (4) | 0.026 (4) | 0.010 (4) |
C7 | 0.058 (5) | 0.041 (5) | 0.101 (7) | 0.004 (4) | 0.047 (5) | 0.002 (5) |
C8 | 0.048 (5) | 0.036 (5) | 0.076 (6) | 0.001 (4) | 0.025 (5) | 0.010 (4) |
C8A | 0.037 (4) | 0.038 (5) | 0.055 (5) | 0.004 (4) | 0.014 (4) | 0.005 (4) |
C9A | 0.037 (4) | 0.022 (4) | 0.051 (5) | 0.009 (3) | 0.017 (4) | −0.001 (3) |
C9 | 0.041 (4) | 0.032 (4) | 0.047 (5) | 0.005 (3) | 0.016 (4) | 0.001 (4) |
C10A | 0.032 (4) | 0.037 (4) | 0.033 (4) | 0.000 (3) | 0.011 (3) | −0.007 (3) |
C10 | 0.036 (4) | 0.036 (4) | 0.042 (5) | 0.003 (3) | 0.010 (4) | −0.001 (3) |
C11A | 0.043 (4) | 0.033 (4) | 0.048 (5) | 0.006 (3) | 0.016 (4) | 0.001 (4) |
C11 | 0.052 (5) | 0.038 (4) | 0.049 (5) | 0.006 (4) | 0.023 (4) | 0.005 (4) |
C12 | 0.061 (5) | 0.041 (5) | 0.046 (5) | 0.018 (4) | 0.017 (4) | 0.010 (4) |
C12A | 0.055 (5) | 0.042 (5) | 0.044 (5) | 0.018 (4) | 0.014 (4) | −0.001 (4) |
C13 | 0.039 (4) | 0.040 (5) | 0.047 (5) | 0.007 (4) | 0.014 (4) | 0.009 (4) |
C13A | 0.040 (4) | 0.037 (4) | 0.038 (5) | 0.008 (4) | 0.007 (4) | 0.002 (4) |
C14A | 0.039 (4) | 0.034 (5) | 0.064 (6) | 0.009 (4) | 0.008 (4) | 0.001 (4) |
C14 | 0.046 (5) | 0.036 (5) | 0.063 (6) | 0.011 (4) | 0.020 (4) | 0.003 (4) |
C15A | 0.045 (5) | 0.040 (5) | 0.067 (6) | 0.011 (4) | 0.017 (5) | 0.002 (5) |
C15 | 0.052 (5) | 0.049 (6) | 0.057 (6) | 0.004 (4) | 0.022 (5) | −0.003 (5) |
C16 | 0.068 (6) | 0.054 (6) | 0.066 (6) | 0.020 (5) | 0.017 (5) | 0.013 (5) |
C16A | 0.106 (7) | 0.081 (7) | 0.061 (6) | 0.054 (6) | 0.014 (6) | 0.010 (5) |
C17A | 0.067 (6) | 0.046 (6) | 0.137 (9) | −0.008 (5) | 0.046 (6) | −0.021 (6) |
C17 | 0.054 (5) | 0.057 (6) | 0.124 (9) | −0.013 (5) | 0.031 (6) | −0.027 (6) |
C18A | 0.052 (5) | 0.049 (5) | 0.049 (5) | 0.011 (4) | 0.009 (4) | −0.005 (4) |
C18 | 0.066 (5) | 0.057 (5) | 0.047 (5) | 0.017 (4) | 0.018 (4) | −0.008 (4) |
C19 | 0.048 (5) | 0.024 (4) | 0.049 (5) | 0.006 (3) | 0.005 (4) | −0.001 (4) |
C19A | 0.049 (5) | 0.025 (4) | 0.051 (5) | 0.003 (3) | 0.009 (4) | 0.004 (3) |
C20 | 0.053 (5) | 0.045 (5) | 0.034 (5) | 0.006 (4) | 0.015 (4) | −0.001 (4) |
C20A | 0.042 (5) | 0.052 (5) | 0.046 (5) | 0.003 (4) | 0.009 (4) | −0.007 (4) |
Geometric parameters (Å, º) top
O1—C19 | 1.448 (7) | C8A—C17A | 1.326 (9) |
O1—H1 | 0.8400 | C8A—C9A | 1.497 (9) |
O1A—C19A | 1.435 (7) | C9A—C11A | 1.544 (8) |
O1A—H1A | 0.8400 | C9A—C10A | 1.557 (9) |
C1A—C2A | 1.531 (8) | C9A—H23A | 1.0000 |
C1A—C10A | 1.537 (8) | C9—C11 | 1.526 (9) |
C1A—H11A | 0.9900 | C9—C10 | 1.562 (9) |
C1A—H12A | 0.9900 | C9—H23 | 1.0000 |
C1—C2 | 1.533 (9) | C10A—C20A | 1.559 (9) |
C1—C10 | 1.537 (9) | C10—C20 | 1.543 (9) |
C1—H11 | 0.9900 | C11A—C12A | 1.514 (9) |
C1—H12 | 0.9900 | C11A—H24A | 0.9900 |
O2—C15 | 1.314 (9) | C11A—H25A | 0.9900 |
O2—H32 | 0.8400 | C11—C12 | 1.526 (9) |
O2A—C15A | 1.329 (9) | C11—H24 | 0.9900 |
O2A—H32A | 0.8400 | C11—H25 | 0.9900 |
C2—C3 | 1.507 (10) | C12—C13 | 1.520 (9) |
C2—H9 | 0.9900 | C12—H26 | 0.9900 |
C2—H10 | 0.9900 | C12—H27 | 0.9900 |
C2A—C3A | 1.516 (9) | C12A—C13A | 1.513 (9) |
C2A—H9A | 0.9900 | C12A—H26A | 0.9900 |
C2A—H10A | 0.9900 | C12A—H27A | 0.9900 |
O3A—C15A | 1.219 (8) | C13—C14 | 1.314 (9) |
O3—C15 | 1.220 (8) | C13—C16 | 1.496 (9) |
C3A—C4A | 1.532 (9) | C13A—C14A | 1.310 (9) |
C3A—H7A | 0.9900 | C13A—C16A | 1.493 (9) |
C3A—H8A | 0.9900 | C14A—C15A | 1.466 (10) |
C3—C4 | 1.536 (9) | C14A—H31A | 0.9500 |
C3—H7 | 0.9900 | C14—C15 | 1.464 (10) |
C3—H8 | 0.9900 | C14—H31 | 0.9500 |
C4A—C18A | 1.542 (9) | C16—H28 | 0.9800 |
C4A—C19A | 1.546 (9) | C16—H29 | 0.9800 |
C4A—C5A | 1.561 (9) | C16—H30 | 0.9800 |
C4—C19 | 1.529 (9) | C16A—H28A | 0.9800 |
C4—C5 | 1.552 (9) | C16A—H29A | 0.9800 |
C4—C18 | 1.553 (9) | C16A—H30A | 0.9800 |
C5A—C6A | 1.526 (9) | C17A—H21A | 0.9500 |
C5A—C10A | 1.562 (8) | C17A—H22A | 0.9500 |
C5A—H16A | 1.0000 | C17—H21 | 0.9500 |
C5—C6 | 1.525 (9) | C17—H22 | 0.9500 |
C5—C10 | 1.556 (8) | C18A—H4A | 0.9800 |
C5—H16 | 1.0000 | C18A—H5A | 0.9800 |
C6—C7 | 1.550 (10) | C18A—H6A | 0.9800 |
C6—H17 | 0.9900 | C18—H4 | 0.9800 |
C6—H18 | 0.9900 | C18—H5 | 0.9800 |
C6A—C7A | 1.528 (9) | C18—H6 | 0.9800 |
C6A—H17A | 0.9900 | C19—H2 | 0.9900 |
C6A—H18A | 0.9900 | C19—H3 | 0.9900 |
C7A—C8A | 1.504 (9) | C19A—H2A | 0.9900 |
C7A—H19A | 0.9900 | C19A—H3A | 0.9900 |
C7A—H20A | 0.9900 | C20—H13 | 0.9800 |
C7—C8 | 1.512 (10) | C20—H14 | 0.9800 |
C7—H19 | 0.9900 | C20—H15 | 0.9800 |
C7—H20 | 0.9900 | C20A—H13A | 0.9800 |
C8—C17 | 1.299 (10) | C20A—H14A | 0.9800 |
C8—C9 | 1.531 (10) | C20A—H15A | 0.9800 |
| | | |
C19—O1—H1 | 109.5 | C1A—C10A—C20A | 108.6 (5) |
C19A—O1A—H1A | 109.5 | C9A—C10A—C20A | 108.3 (5) |
C2A—C1A—C10A | 114.7 (6) | C1A—C10A—C5A | 107.7 (5) |
C2A—C1A—H11A | 108.6 | C9A—C10A—C5A | 107.9 (5) |
C10A—C1A—H11A | 108.6 | C20A—C10A—C5A | 114.5 (5) |
C2A—C1A—H12A | 108.6 | C1—C10—C20 | 109.1 (6) |
C10A—C1A—H12A | 108.6 | C1—C10—C5 | 108.8 (5) |
H11A—C1A—H12A | 107.6 | C20—C10—C5 | 113.4 (5) |
C2—C1—C10 | 114.0 (6) | C1—C10—C9 | 108.9 (5) |
C2—C1—H11 | 108.7 | C20—C10—C9 | 109.6 (5) |
C10—C1—H11 | 108.7 | C5—C10—C9 | 106.8 (5) |
C2—C1—H12 | 108.7 | C12A—C11A—C9A | 112.9 (6) |
C10—C1—H12 | 108.7 | C12A—C11A—H24A | 109.0 |
H11—C1—H12 | 107.6 | C9A—C11A—H24A | 109.0 |
C15—O2—H32 | 109.5 | C12A—C11A—H25A | 109.0 |
C15A—O2A—H32A | 109.5 | C9A—C11A—H25A | 109.0 |
C3—C2—C1 | 111.7 (6) | H24A—C11A—H25A | 107.8 |
C3—C2—H9 | 109.3 | C9—C11—C12 | 110.2 (6) |
C1—C2—H9 | 109.3 | C9—C11—H24 | 109.6 |
C3—C2—H10 | 109.3 | C12—C11—H24 | 109.6 |
C1—C2—H10 | 109.3 | C9—C11—H25 | 109.6 |
H9—C2—H10 | 107.9 | C12—C11—H25 | 109.6 |
C3A—C2A—C1A | 111.6 (6) | H24—C11—H25 | 108.1 |
C3A—C2A—H9A | 109.3 | C13—C12—C11 | 118.3 (6) |
C1A—C2A—H9A | 109.3 | C13—C12—H26 | 107.7 |
C3A—C2A—H10A | 109.3 | C11—C12—H26 | 107.7 |
C1A—C2A—H10A | 109.3 | C13—C12—H27 | 107.7 |
H9A—C2A—H10A | 108.0 | C11—C12—H27 | 107.7 |
C2A—C3A—C4A | 113.8 (6) | H26—C12—H27 | 107.1 |
C2A—C3A—H7A | 108.8 | C13A—C12A—C11A | 117.1 (6) |
C4A—C3A—H7A | 108.8 | C13A—C12A—H26A | 108.0 |
C2A—C3A—H8A | 108.8 | C11A—C12A—H26A | 108.0 |
C4A—C3A—H8A | 108.8 | C13A—C12A—H27A | 108.0 |
H7A—C3A—H8A | 107.7 | C11A—C12A—H27A | 108.0 |
C2—C3—C4 | 113.5 (6) | H26A—C12A—H27A | 107.3 |
C2—C3—H7 | 108.9 | C14—C13—C16 | 125.2 (7) |
C4—C3—H7 | 108.9 | C14—C13—C12 | 121.5 (6) |
C2—C3—H8 | 108.9 | C16—C13—C12 | 113.3 (6) |
C4—C3—H8 | 108.9 | C14A—C13A—C16A | 125.7 (7) |
H7—C3—H8 | 107.7 | C14A—C13A—C12A | 120.4 (6) |
C3A—C4A—C18A | 108.1 (6) | C16A—C13A—C12A | 113.9 (6) |
C3A—C4A—C19A | 110.5 (6) | C13A—C14A—C15A | 127.7 (7) |
C18A—C4A—C19A | 108.2 (5) | C13A—C14A—H31A | 116.2 |
C3A—C4A—C5A | 109.3 (5) | C15A—C14A—H31A | 116.2 |
C18A—C4A—C5A | 109.2 (5) | C13—C14—C15 | 127.3 (7) |
C19A—C4A—C5A | 111.6 (5) | C13—C14—H31 | 116.3 |
C19—C4—C3 | 109.5 (6) | C15—C14—H31 | 116.3 |
C19—C4—C5 | 113.1 (5) | O3A—C15A—O2A | 121.8 (7) |
C3—C4—C5 | 109.5 (6) | O3A—C15A—C14A | 125.8 (8) |
C19—C4—C18 | 106.9 (6) | O2A—C15A—C14A | 112.4 (7) |
C3—C4—C18 | 108.1 (6) | O3—C15—O2 | 122.3 (7) |
C5—C4—C18 | 109.6 (6) | O3—C15—C14 | 125.6 (8) |
C6A—C5A—C4A | 113.9 (5) | O2—C15—C14 | 112.1 (7) |
C6A—C5A—C10A | 111.9 (5) | C13—C16—H28 | 109.5 |
C4A—C5A—C10A | 117.9 (5) | C13—C16—H29 | 109.5 |
C6A—C5A—H16A | 103.7 | H28—C16—H29 | 109.5 |
C4A—C5A—H16A | 103.7 | C13—C16—H30 | 109.5 |
C10A—C5A—H16A | 103.7 | H28—C16—H30 | 109.5 |
C6—C5—C4 | 113.4 (5) | H29—C16—H30 | 109.5 |
C6—C5—C10 | 112.3 (6) | C13A—C16A—H28A | 109.5 |
C4—C5—C10 | 117.7 (6) | C13A—C16A—H29A | 109.5 |
C6—C5—H16 | 103.9 | H28A—C16A—H29A | 109.5 |
C4—C5—H16 | 103.9 | C13A—C16A—H30A | 109.5 |
C10—C5—H16 | 103.9 | H28A—C16A—H30A | 109.5 |
C5—C6—C7 | 109.9 (6) | H29A—C16A—H30A | 109.5 |
C5—C6—H17 | 109.7 | C8A—C17A—H21A | 120.0 |
C7—C6—H17 | 109.7 | C8A—C17A—H22A | 120.0 |
C5—C6—H18 | 109.7 | H21A—C17A—H22A | 120.0 |
C7—C6—H18 | 109.7 | C8—C17—H21 | 120.0 |
H17—C6—H18 | 108.2 | C8—C17—H22 | 120.0 |
C5A—C6A—C7A | 110.5 (5) | H21—C17—H22 | 120.0 |
C5A—C6A—H17A | 109.5 | C4A—C18A—H4A | 109.5 |
C7A—C6A—H17A | 109.5 | C4A—C18A—H5A | 109.5 |
C5A—C6A—H18A | 109.5 | H4A—C18A—H5A | 109.5 |
C7A—C6A—H18A | 109.5 | C4A—C18A—H6A | 109.5 |
H17A—C6A—H18A | 108.1 | H4A—C18A—H6A | 109.5 |
C8A—C7A—C6A | 111.2 (6) | H5A—C18A—H6A | 109.5 |
C8A—C7A—H19A | 109.4 | C4—C18—H4 | 109.5 |
C6A—C7A—H19A | 109.4 | C4—C18—H5 | 109.5 |
C8A—C7A—H20A | 109.4 | H4—C18—H5 | 109.5 |
C6A—C7A—H20A | 109.4 | C4—C18—H6 | 109.5 |
H19A—C7A—H20A | 108.0 | H4—C18—H6 | 109.5 |
C8—C7—C6 | 111.6 (6) | H5—C18—H6 | 109.5 |
C8—C7—H19 | 109.3 | O1—C19—C4 | 112.3 (5) |
C6—C7—H19 | 109.3 | O1—C19—H2 | 109.1 |
C8—C7—H20 | 109.3 | C4—C19—H2 | 109.1 |
C6—C7—H20 | 109.3 | O1—C19—H3 | 109.1 |
H19—C7—H20 | 108.0 | C4—C19—H3 | 109.1 |
C17—C8—C7 | 120.5 (7) | H2—C19—H3 | 107.9 |
C17—C8—C9 | 126.5 (7) | O1A—C19A—C4A | 111.3 (5) |
C7—C8—C9 | 113.0 (7) | O1A—C19A—H2A | 109.4 |
C17A—C8A—C9A | 126.2 (7) | C4A—C19A—H2A | 109.4 |
C17A—C8A—C7A | 119.5 (7) | O1A—C19A—H3A | 109.4 |
C9A—C8A—C7A | 114.3 (6) | C4A—C19A—H3A | 109.4 |
C8A—C9A—C11A | 112.6 (5) | H2A—C19A—H3A | 108.0 |
C8A—C9A—C10A | 110.6 (5) | C10—C20—H13 | 109.5 |
C11A—C9A—C10A | 114.5 (5) | C10—C20—H14 | 109.5 |
C8A—C9A—H23A | 106.2 | H13—C20—H14 | 109.5 |
C11A—C9A—H23A | 106.2 | C10—C20—H15 | 109.5 |
C10A—C9A—H23A | 106.2 | H13—C20—H15 | 109.5 |
C11—C9—C8 | 112.2 (6) | H14—C20—H15 | 109.5 |
C11—C9—C10 | 114.9 (6) | C10A—C20A—H13A | 109.5 |
C8—C9—C10 | 110.3 (6) | C10A—C20A—H14A | 109.5 |
C11—C9—H23 | 106.3 | H13A—C20A—H14A | 109.5 |
C8—C9—H23 | 106.3 | C10A—C20A—H15A | 109.5 |
C10—C9—H23 | 106.3 | H13A—C20A—H15A | 109.5 |
C1A—C10A—C9A | 109.7 (5) | H14A—C20A—H15A | 109.5 |
| | | |
C10—C1—C2—C3 | −56.0 (9) | C8A—C9A—C10A—C5A | −56.0 (7) |
C10A—C1A—C2A—C3A | −56.2 (8) | C11A—C9A—C10A—C5A | 175.6 (5) |
C1A—C2A—C3A—C4A | 55.2 (8) | C6A—C5A—C10A—C1A | 176.3 (6) |
C1—C2—C3—C4 | 56.1 (9) | C4A—C5A—C10A—C1A | −48.8 (7) |
C2A—C3A—C4A—C18A | −169.0 (6) | C6A—C5A—C10A—C9A | 57.9 (7) |
C2A—C3A—C4A—C19A | 72.8 (7) | C4A—C5A—C10A—C9A | −167.2 (5) |
C2A—C3A—C4A—C5A | −50.3 (8) | C6A—C5A—C10A—C20A | −62.8 (7) |
C2—C3—C4—C19 | 73.4 (8) | C4A—C5A—C10A—C20A | 72.1 (7) |
C2—C3—C4—C5 | −51.0 (8) | C2—C1—C10—C20 | −74.5 (8) |
C2—C3—C4—C18 | −170.4 (6) | C2—C1—C10—C5 | 49.8 (8) |
C3A—C4A—C5A—C6A | −177.0 (6) | C2—C1—C10—C9 | 165.9 (6) |
C18A—C4A—C5A—C6A | −59.0 (7) | C6—C5—C10—C1 | 178.1 (6) |
C19A—C4A—C5A—C6A | 60.6 (7) | C4—C5—C10—C1 | −47.6 (8) |
C3A—C4A—C5A—C10A | 49.0 (8) | C6—C5—C10—C20 | −60.2 (7) |
C18A—C4A—C5A—C10A | 167.0 (6) | C4—C5—C10—C20 | 74.1 (8) |
C19A—C4A—C5A—C10A | −73.5 (7) | C6—C5—C10—C9 | 60.6 (7) |
C19—C4—C5—C6 | 59.8 (8) | C4—C5—C10—C9 | −165.1 (6) |
C3—C4—C5—C6 | −177.9 (6) | C11—C9—C10—C1 | 56.3 (8) |
C18—C4—C5—C6 | −59.5 (8) | C8—C9—C10—C1 | −175.7 (6) |
C19—C4—C5—C10 | −74.1 (8) | C11—C9—C10—C20 | −63.0 (8) |
C3—C4—C5—C10 | 48.3 (8) | C8—C9—C10—C20 | 64.9 (7) |
C18—C4—C5—C10 | 166.7 (6) | C11—C9—C10—C5 | 173.7 (6) |
C4—C5—C6—C7 | 165.5 (6) | C8—C9—C10—C5 | −58.3 (7) |
C10—C5—C6—C7 | −58.2 (8) | C8A—C9A—C11A—C12A | 77.4 (8) |
C4A—C5A—C6A—C7A | 166.1 (6) | C10A—C9A—C11A—C12A | −155.2 (6) |
C10A—C5A—C6A—C7A | −57.1 (8) | C8—C9—C11—C12 | 79.7 (8) |
C5A—C6A—C7A—C8A | 53.3 (8) | C10—C9—C11—C12 | −153.3 (6) |
C5—C6—C7—C8 | 53.0 (9) | C9—C11—C12—C13 | −168.8 (6) |
C6—C7—C8—C17 | 126.3 (9) | C9A—C11A—C12A—C13A | −175.7 (6) |
C6—C7—C8—C9 | −53.7 (9) | C11—C12—C13—C14 | 9.4 (11) |
C6A—C7A—C8A—C17A | 124.0 (8) | C11—C12—C13—C16 | −173.7 (7) |
C6A—C7A—C8A—C9A | −54.3 (8) | C11A—C12A—C13A—C14A | 7.9 (10) |
C17A—C8A—C9A—C11A | 7.5 (11) | C11A—C12A—C13A—C16A | −172.4 (7) |
C7A—C8A—C9A—C11A | −174.3 (6) | C16A—C13A—C14A—C15A | −0.3 (13) |
C17A—C8A—C9A—C10A | −122.0 (8) | C12A—C13A—C14A—C15A | 179.3 (7) |
C7A—C8A—C9A—C10A | 56.3 (8) | C16—C13—C14—C15 | −1.3 (13) |
C17—C8—C9—C11 | 6.7 (12) | C12—C13—C14—C15 | 175.3 (7) |
C7—C8—C9—C11 | −173.3 (6) | C13A—C14A—C15A—O3A | 5.9 (13) |
C17—C8—C9—C10 | −122.8 (9) | C13A—C14A—C15A—O2A | −174.6 (7) |
C7—C8—C9—C10 | 57.2 (8) | C13—C14—C15—O3 | −5.4 (13) |
C2A—C1A—C10A—C9A | 168.1 (6) | C13—C14—C15—O2 | 174.9 (8) |
C2A—C1A—C10A—C20A | −73.7 (7) | C3—C4—C19—O1 | 64.6 (7) |
C2A—C1A—C10A—C5A | 50.9 (7) | C5—C4—C19—O1 | −173.0 (5) |
C8A—C9A—C10A—C1A | −173.1 (6) | C18—C4—C19—O1 | −52.3 (8) |
C11A—C9A—C10A—C1A | 58.5 (7) | C3A—C4A—C19A—O1A | 64.8 (7) |
C8A—C9A—C10A—C20A | 68.5 (7) | C18A—C4A—C19A—O1A | −53.4 (7) |
C11A—C9A—C10A—C20A | −59.9 (7) | C5A—C4A—C19A—O1A | −173.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3i | 0.84 | 1.88 | 2.694 (7) | 164 |
O2—H32···O1ii | 0.84 | 1.76 | 2.582 (7) | 166 |
O2A—H32A···O1Aiii | 0.84 | 1.79 | 2.603 (6) | 163 |
O1—H1···O3A | 0.84 | 1.84 | 2.673 (7) | 174 |
Symmetry codes: (i) x+2, y−1, z; (ii) −x+1, y+1/2, −z+2; (iii) −x+3, y+1/2, −z+2. |
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