Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018708/tk2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018708/tk2040Isup2.hkl |
CCDC reference: 610916
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.066
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C20 .. 7.32 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.07 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
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 27.50 From the CIF: _reflns_number_total 4116 Count of symmetry unique reflns 2367 Completeness (_total/calc) 173.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1749 Fraction of Friedel pairs measured 0.739 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C20H25ClO3 | F(000) = 744.00 |
Mr = 348.85 | Dx = 1.285 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 13502 reflections |
a = 7.499 (2) Å | θ = 3.0–27.5° |
b = 15.365 (5) Å | µ = 0.23 mm−1 |
c = 15.647 (4) Å | T = 298 K |
V = 1802.9 (9) Å3 | Chunk, colorless |
Z = 4 | 0.26 × 0.21 × 0.14 mm |
Rigaku R-AXIS RAPID diffractometer | 2498 reflections with F2 > 2σ(F2) |
Detector resolution: 10.0 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.918, Tmax = 0.969 | k = −19→19 |
17271 measured reflections | l = −20→19 |
4116 independent reflections |
Refinement on F2 | (Δ/σ)max < 0.001 |
R[F2 > 2σ(F2)] = 0.036 | Δρmax = 0.24 e Å−3 |
wR(F2) = 0.066 | Δρmin = −0.19 e Å−3 |
S = 1.01 | Extinction correction: Larson (1970), equation 22 |
4116 reflections | Extinction coefficient: 112 (15) |
219 parameters | Absolute structure: Flack (1983), with 1758 Friedel pairs |
H-atom parameters constrained | Absolute structure parameter: 0.054 (5) |
w = 1/[1.0800σ(Fo2)]/(4Fo2) |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.83719 (8) | 0.09270 (4) | 0.77193 (3) | 0.07901 (18) | |
O1 | 0.6732 (2) | 0.97219 (9) | 0.58327 (9) | 0.1026 (6) | |
O2 | 0.72856 (18) | 0.25442 (8) | 0.58983 (6) | 0.0601 (3) | |
O3 | 0.9229 (2) | 0.26526 (10) | 0.69734 (9) | 0.0930 (6) | |
C1 | 0.7281 (2) | 0.47503 (11) | 0.50088 (9) | 0.0479 (5) | |
C2 | 0.6380 (2) | 0.56276 (11) | 0.50757 (9) | 0.0473 (5) | |
C3 | 0.6553 (2) | 0.61813 (12) | 0.42961 (10) | 0.0557 (5) | |
C4 | 0.6663 (2) | 0.70382 (12) | 0.43255 (10) | 0.0568 (6) | |
C5 | 0.6629 (2) | 0.75210 (12) | 0.51193 (10) | 0.0517 (5) | |
C6 | 0.6758 (2) | 0.83927 (12) | 0.51169 (11) | 0.0590 (6) | |
C7 | 0.6653 (2) | 0.89348 (13) | 0.58731 (12) | 0.0674 (6) | |
C8 | 0.6422 (3) | 0.84671 (12) | 0.67129 (12) | 0.0721 (7) | |
C9 | 0.7113 (2) | 0.75364 (12) | 0.66966 (10) | 0.0581 (6) | |
C10 | 0.6358 (2) | 0.70196 (11) | 0.59474 (10) | 0.0479 (5) | |
C11 | 0.7117 (2) | 0.61016 (11) | 0.58667 (9) | 0.0448 (4) | |
C12 | 0.6835 (2) | 0.55417 (10) | 0.66694 (9) | 0.0539 (5) | |
C13 | 0.7570 (2) | 0.46156 (11) | 0.65813 (10) | 0.0549 (5) | |
C14 | 0.6874 (2) | 0.41651 (11) | 0.57805 (9) | 0.0445 (4) | |
C15 | 0.7885 (2) | 0.33497 (11) | 0.54980 (10) | 0.0534 (5) | |
C16 | 0.7543 (3) | 0.32620 (12) | 0.45330 (10) | 0.0706 (7) | |
C17 | 0.6953 (2) | 0.41631 (11) | 0.42340 (9) | 0.0681 (6) | |
C18 | 0.8069 (3) | 0.22846 (12) | 0.66177 (11) | 0.0547 (6) | |
C19 | 0.7199 (2) | 0.14513 (12) | 0.69018 (11) | 0.0626 (6) | |
C20 | 0.4878 (2) | 0.39485 (13) | 0.58625 (12) | 0.0648 (6) | |
H1 | 0.8566 | 0.4863 | 0.5023 | 0.058* | |
H2 | 0.5106 | 0.5525 | 0.5172 | 0.057* | |
H3 | 0.6584 | 0.5910 | 0.3765 | 0.067* | |
H4 | 0.6767 | 0.7344 | 0.3815 | 0.068* | |
H6 | 0.6926 | 0.8668 | 0.4594 | 0.071* | |
H10 | 0.5070 | 0.6964 | 0.6038 | 0.057* | |
H11 | 0.8408 | 0.6160 | 0.5785 | 0.054* | |
H15 | 0.9163 | 0.3429 | 0.5601 | 0.064* | |
H81 | 0.7063 | 0.8786 | 0.7151 | 0.087* | |
H82 | 0.5162 | 0.8455 | 0.6853 | 0.087* | |
H91 | 0.8403 | 0.7549 | 0.6650 | 0.070* | |
H92 | 0.6776 | 0.7250 | 0.7225 | 0.070* | |
H121 | 0.7428 | 0.5822 | 0.7147 | 0.065* | |
H122 | 0.5566 | 0.5506 | 0.6784 | 0.065* | |
H131 | 0.8861 | 0.4643 | 0.6553 | 0.066* | |
H132 | 0.7215 | 0.4280 | 0.7078 | 0.066* | |
H161 | 0.8626 | 0.3087 | 0.4240 | 0.085* | |
H162 | 0.6614 | 0.2837 | 0.4425 | 0.085* | |
H171 | 0.7658 | 0.4353 | 0.3749 | 0.082* | |
H172 | 0.5700 | 0.4161 | 0.4079 | 0.082* | |
H191 | 0.6008 | 0.1583 | 0.7106 | 0.075* | |
H192 | 0.7124 | 0.1062 | 0.6415 | 0.075* | |
H201 | 0.4226 | 0.4469 | 0.5995 | 0.078* | |
H202 | 0.4452 | 0.3711 | 0.5333 | 0.078* | |
H203 | 0.4710 | 0.3530 | 0.6311 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0980 (4) | 0.0720 (3) | 0.0670 (2) | 0.0064 (3) | −0.0090 (3) | 0.0172 (2) |
O1 | 0.1530 (17) | 0.0477 (9) | 0.1073 (10) | −0.0009 (10) | −0.0192 (13) | −0.0102 (8) |
O2 | 0.0714 (9) | 0.0469 (7) | 0.0619 (6) | −0.0040 (7) | −0.0139 (6) | 0.0071 (6) |
O3 | 0.1088 (13) | 0.0803 (11) | 0.0897 (10) | −0.0295 (10) | −0.0462 (10) | 0.0204 (8) |
C1 | 0.0541 (12) | 0.0498 (10) | 0.0399 (8) | 0.0028 (9) | −0.0007 (9) | −0.0003 (8) |
C2 | 0.0503 (11) | 0.0508 (11) | 0.0406 (8) | 0.0013 (9) | −0.0031 (8) | 0.0019 (8) |
C3 | 0.0658 (12) | 0.0611 (13) | 0.0401 (9) | 0.0026 (11) | −0.0026 (9) | 0.0017 (8) |
C4 | 0.0644 (13) | 0.0569 (12) | 0.0491 (10) | 0.0032 (11) | −0.0037 (10) | 0.0069 (9) |
C5 | 0.0471 (11) | 0.0520 (11) | 0.0560 (10) | 0.0019 (10) | 0.0019 (9) | 0.0035 (9) |
C6 | 0.0577 (13) | 0.0566 (12) | 0.0626 (11) | −0.0004 (11) | −0.0049 (10) | 0.0040 (10) |
C7 | 0.0670 (14) | 0.0529 (12) | 0.0823 (13) | 0.0010 (12) | −0.0088 (13) | −0.0016 (11) |
C8 | 0.0801 (17) | 0.0637 (14) | 0.0725 (12) | −0.0057 (13) | 0.0015 (12) | −0.0209 (11) |
C9 | 0.0669 (15) | 0.0558 (11) | 0.0516 (9) | −0.0062 (11) | 0.0002 (9) | −0.0037 (9) |
C10 | 0.0436 (11) | 0.0515 (10) | 0.0485 (9) | −0.0048 (9) | 0.0003 (9) | −0.0021 (8) |
C11 | 0.0433 (10) | 0.0492 (10) | 0.0419 (8) | −0.0010 (9) | −0.0004 (8) | 0.0018 (8) |
C12 | 0.0705 (14) | 0.0541 (11) | 0.0371 (8) | −0.0068 (11) | −0.0018 (9) | −0.0016 (8) |
C13 | 0.0689 (14) | 0.0540 (11) | 0.0419 (9) | −0.0050 (11) | −0.0046 (9) | 0.0065 (8) |
C14 | 0.0464 (11) | 0.0479 (10) | 0.0391 (8) | −0.0027 (9) | −0.0046 (8) | 0.0011 (7) |
C15 | 0.0604 (14) | 0.0462 (10) | 0.0537 (10) | −0.0004 (10) | −0.0034 (9) | 0.0023 (9) |
C16 | 0.1002 (18) | 0.0577 (13) | 0.0540 (10) | 0.0108 (13) | 0.0049 (11) | −0.0039 (9) |
C17 | 0.1002 (17) | 0.0581 (12) | 0.0460 (9) | 0.0081 (13) | 0.0005 (11) | −0.0044 (9) |
C18 | 0.0653 (15) | 0.0473 (12) | 0.0516 (10) | 0.0038 (11) | −0.0057 (10) | −0.0022 (9) |
C19 | 0.0702 (15) | 0.0537 (11) | 0.0639 (10) | 0.0039 (11) | −0.0042 (10) | 0.0052 (9) |
C20 | 0.0608 (13) | 0.0623 (13) | 0.0713 (12) | −0.0053 (11) | 0.0061 (10) | 0.0007 (11) |
Cl1—C19 | 1.7488 (19) | C18—C19 | 1.504 (2) |
O1—C7 | 1.212 (2) | C1—H1 | 0.980 |
O2—C15 | 1.458 (2) | C2—H2 | 0.980 |
O2—C18 | 1.331 (2) | C3—H3 | 0.930 |
O3—C18 | 1.177 (2) | C4—H4 | 0.930 |
C1—C2 | 1.511 (2) | C6—H6 | 0.930 |
C1—C14 | 1.536 (2) | C8—H81 | 0.970 |
C1—C17 | 1.531 (2) | C8—H82 | 0.970 |
C2—C3 | 1.493 (2) | C9—H91 | 0.970 |
C2—C11 | 1.539 (2) | C9—H92 | 0.970 |
C3—C4 | 1.320 (2) | C10—H10 | 0.980 |
C4—C5 | 1.447 (2) | C11—H11 | 0.980 |
C5—C6 | 1.343 (2) | C12—H121 | 0.970 |
C5—C10 | 1.521 (2) | C12—H122 | 0.970 |
C6—C7 | 1.449 (2) | C13—H131 | 0.970 |
C7—C8 | 1.508 (2) | C13—H132 | 0.970 |
C8—C9 | 1.521 (2) | C15—H15 | 0.980 |
C9—C10 | 1.525 (2) | C16—H161 | 0.970 |
C10—C11 | 1.526 (2) | C16—H162 | 0.970 |
C11—C12 | 1.537 (2) | C17—H171 | 0.970 |
C12—C13 | 1.532 (2) | C17—H172 | 0.970 |
C13—C14 | 1.524 (2) | C19—H191 | 0.970 |
C14—C15 | 1.529 (2) | C19—H192 | 0.970 |
C14—C20 | 1.539 (2) | C20—H201 | 0.960 |
C15—C16 | 1.537 (2) | C20—H202 | 0.960 |
C16—C17 | 1.527 (2) | C20—H203 | 0.960 |
O1···C19 | 3.159 (2) | H11···H6 | 2.717 |
O3···C9 | 3.448 (2) | H15···H162 | 2.676 |
C9···O3 | 3.448 (2) | H81···Cl1 | 3.546 |
C19···O1 | 3.159 (2) | H81···O3 | 3.556 |
Cl1···H4 | 3.163 | H81···C20 | 3.441 |
Cl1···H6 | 3.006 | H81···H132 | 3.511 |
Cl1···H11 | 3.382 | H81···H201 | 3.233 |
Cl1···H81 | 3.546 | H81···H203 | 2.778 |
Cl1···H121 | 3.161 | H82···C3 | 3.297 |
Cl1···H122 | 3.122 | H82···C4 | 3.295 |
Cl1···H131 | 3.082 | H82···H3 | 3.014 |
Cl1···H172 | 3.315 | H82···H4 | 3.014 |
Cl1···H201 | 3.586 | H82···H132 | 2.754 |
O1···H1 | 2.800 | H82···H191 | 3.421 |
O1···H2 | 3.003 | H82···H203 | 2.877 |
O1···H171 | 3.433 | H91···O3 | 2.796 |
O1···H172 | 3.438 | H91···C3 | 3.403 |
O1···H191 | 3.527 | H91···C4 | 2.951 |
O1···H192 | 2.270 | H91···H3 | 3.424 |
O2···H161 | 2.919 | H91···H4 | 2.631 |
O2···H162 | 3.337 | H92···O3 | 3.307 |
O2···H202 | 3.174 | H92···C19 | 3.501 |
O3···H4 | 2.977 | H92···H161 | 3.210 |
O3···H81 | 3.556 | H92···H171 | 3.455 |
O3···H91 | 2.796 | H92···H191 | 2.551 |
O3···H92 | 3.307 | H92···H203 | 3.218 |
O3···H162 | 2.925 | H121···Cl1 | 3.161 |
O3···H172 | 3.420 | H121···C17 | 3.299 |
C2···H6 | 3.549 | H121···H171 | 2.522 |
C3···H82 | 3.297 | H121···H172 | 3.334 |
C3···H91 | 3.403 | H121···H191 | 3.062 |
C4···H10 | 3.033 | H122···Cl1 | 3.122 |
C4···H82 | 3.295 | H122···C19 | 3.262 |
C4···H91 | 2.951 | H122···H171 | 3.358 |
C5···H10 | 3.251 | H122···H191 | 2.674 |
C5···H11 | 3.456 | H122···H192 | 3.569 |
C6···H1 | 3.600 | H131···Cl1 | 3.082 |
C6···H2 | 3.046 | H131···H3 | 3.580 |
C6···H10 | 3.121 | H132···C8 | 3.547 |
C6···H11 | 2.963 | H132···H3 | 2.804 |
C7···H1 | 3.277 | H132···H81 | 3.511 |
C7···H2 | 3.173 | H132···H82 | 2.754 |
C7···H11 | 3.561 | H132···H171 | 3.355 |
C7···H192 | 3.395 | H161···O2 | 2.919 |
C8···H132 | 3.547 | H161···C19 | 3.298 |
C8···H203 | 3.208 | H161···C20 | 3.270 |
C9···H4 | 3.585 | H161···H92 | 3.210 |
C9···H191 | 3.337 | H161···H162 | 3.376 |
C10···H4 | 3.599 | H161···H191 | 2.807 |
C10···H6 | 3.589 | H161···H192 | 3.106 |
C10···H191 | 3.589 | H161···H202 | 2.910 |
C12···H171 | 3.280 | H161···H203 | 2.753 |
C12···H191 | 3.283 | H162···O2 | 3.337 |
C13···H3 | 3.568 | H162···O3 | 2.925 |
C15···H162 | 3.341 | H162···C15 | 3.341 |
C16···H202 | 3.360 | H162···C18 | 3.125 |
C16···H203 | 3.459 | H162···H15 | 2.676 |
C17···H121 | 3.299 | H162···H161 | 3.376 |
C18···H4 | 3.487 | H162···H202 | 3.215 |
C18···H162 | 3.125 | H162···H203 | 3.336 |
C18···H172 | 3.165 | H171···O1 | 3.433 |
C18···H202 | 3.568 | H171···C12 | 3.280 |
C19···H92 | 3.501 | H171···H92 | 3.455 |
C19···H122 | 3.262 | H171···H121 | 2.522 |
C19···H161 | 3.298 | H171···H122 | 3.358 |
C19···H172 | 3.184 | H171···H132 | 3.355 |
C20···H81 | 3.441 | H171···H191 | 3.189 |
C20···H161 | 3.270 | H171···H192 | 3.419 |
H1···O1 | 2.800 | H172···Cl1 | 3.315 |
H1···C6 | 3.600 | H172···O1 | 3.438 |
H1···C7 | 3.277 | H172···O3 | 3.420 |
H1···H6 | 3.436 | H172···C18 | 3.165 |
H2···O1 | 3.003 | H172···C19 | 3.184 |
H2···C6 | 3.046 | H172···H121 | 3.334 |
H2···C7 | 3.173 | H172···H192 | 2.812 |
H2···H6 | 2.713 | H191···O1 | 3.527 |
H3···C13 | 3.568 | H191···C9 | 3.337 |
H3···H82 | 3.014 | H191···C10 | 3.589 |
H3···H91 | 3.424 | H191···C12 | 3.283 |
H3···H131 | 3.580 | H191···H4 | 3.558 |
H3···H132 | 2.804 | H191···H10 | 3.071 |
H4···Cl1 | 3.163 | H191···H82 | 3.421 |
H4···O3 | 2.977 | H191···H92 | 2.551 |
H4···C9 | 3.585 | H191···H121 | 3.062 |
H4···C10 | 3.599 | H191···H122 | 2.674 |
H4···C18 | 3.487 | H191···H161 | 2.807 |
H4···H10 | 2.705 | H191···H171 | 3.189 |
H4···H11 | 3.467 | H192···O1 | 2.270 |
H4···H82 | 3.014 | H192···C7 | 3.395 |
H4···H91 | 2.631 | H192···H122 | 3.569 |
H4···H191 | 3.558 | H192···H161 | 3.106 |
H6···Cl1 | 3.006 | H192···H171 | 3.419 |
H6···C2 | 3.549 | H192···H172 | 2.812 |
H6···C10 | 3.589 | H192···H202 | 3.264 |
H6···H1 | 3.436 | H201···Cl1 | 3.586 |
H6···H2 | 2.713 | H201···H6 | 3.467 |
H6···H10 | 2.735 | H201···H81 | 3.233 |
H6···H11 | 2.717 | H202···O2 | 3.174 |
H6···H201 | 3.467 | H202···C16 | 3.360 |
H10···C4 | 3.033 | H202···C18 | 3.568 |
H10···C5 | 3.251 | H202···H161 | 2.910 |
H10···C6 | 3.121 | H202···H162 | 3.215 |
H10···H4 | 2.705 | H202···H192 | 3.264 |
H10···H6 | 2.735 | H203···C8 | 3.208 |
H10···H191 | 3.071 | H203···C16 | 3.459 |
H11···Cl1 | 3.382 | H203···H81 | 2.778 |
H11···C5 | 3.456 | H203···H82 | 2.877 |
H11···C6 | 2.963 | H203···H92 | 3.218 |
H11···C7 | 3.561 | H203···H161 | 2.753 |
H11···H4 | 3.467 | H203···H162 | 3.336 |
C15—O2—C18 | 118.80 (14) | C7—C6—H6 | 117.7 |
C2—C1—C14 | 112.27 (13) | C7—C8—H81 | 108.5 |
C2—C1—C17 | 120.58 (14) | C7—C8—H82 | 108.5 |
C14—C1—C17 | 104.22 (13) | C9—C8—H81 | 108.5 |
C1—C2—C3 | 114.39 (13) | C9—C8—H82 | 108.5 |
C1—C2—C11 | 108.50 (13) | H81—C8—H82 | 109.5 |
C3—C2—C11 | 110.87 (14) | C8—C9—H91 | 108.8 |
C2—C3—C4 | 123.05 (14) | C8—C9—H92 | 108.8 |
C3—C4—C5 | 122.70 (15) | C10—C9—H91 | 108.8 |
C4—C5—C6 | 120.51 (15) | C10—C9—H92 | 108.8 |
C4—C5—C10 | 118.29 (16) | H91—C9—H92 | 109.5 |
C6—C5—C10 | 121.14 (15) | C5—C10—H10 | 107.4 |
C5—C6—C7 | 124.55 (16) | C9—C10—H10 | 107.4 |
O1—C7—C6 | 121.88 (18) | C11—C10—H10 | 107.4 |
O1—C7—C8 | 121.77 (18) | C2—C11—H11 | 107.1 |
C6—C7—C8 | 116.35 (17) | C10—C11—H11 | 107.1 |
C7—C8—C9 | 113.22 (16) | C12—C11—H11 | 107.1 |
C8—C9—C10 | 112.08 (15) | C11—C12—H121 | 108.5 |
C5—C10—C9 | 109.97 (14) | C11—C12—H122 | 108.5 |
C5—C10—C11 | 110.35 (13) | C13—C12—H121 | 108.5 |
C9—C10—C11 | 113.97 (14) | C13—C12—H122 | 108.5 |
C2—C11—C10 | 111.70 (13) | H121—C12—H122 | 109.5 |
C2—C11—C12 | 110.05 (13) | C12—C13—H131 | 108.9 |
C10—C11—C12 | 113.47 (12) | C12—C13—H132 | 108.9 |
C11—C12—C13 | 113.38 (13) | C14—C13—H131 | 108.9 |
C12—C13—C14 | 111.89 (14) | C14—C13—H132 | 108.9 |
C1—C14—C13 | 108.21 (13) | H131—C13—H132 | 109.5 |
C1—C14—C15 | 98.86 (12) | O2—C15—H15 | 109.6 |
C1—C14—C20 | 112.65 (14) | C14—C15—H15 | 109.6 |
C13—C14—C15 | 116.11 (14) | C16—C15—H15 | 109.6 |
C13—C14—C20 | 111.27 (14) | C15—C16—H161 | 110.4 |
C15—C14—C20 | 109.20 (14) | C15—C16—H162 | 110.4 |
O2—C15—C14 | 114.74 (14) | C17—C16—H161 | 110.4 |
O2—C15—C16 | 107.23 (13) | C17—C16—H162 | 110.4 |
C14—C15—C16 | 105.86 (14) | H161—C16—H162 | 109.5 |
C15—C16—C17 | 105.65 (13) | C1—C17—H171 | 110.8 |
C1—C17—C16 | 104.19 (12) | C1—C17—H172 | 110.8 |
O2—C18—O3 | 125.59 (17) | C16—C17—H171 | 110.8 |
O2—C18—C19 | 108.29 (16) | C16—C17—H172 | 110.8 |
O3—C18—C19 | 126.12 (17) | H171—C17—H172 | 109.5 |
Cl1—C19—C18 | 112.98 (14) | Cl1—C19—H191 | 108.6 |
C2—C1—H1 | 106.3 | Cl1—C19—H192 | 108.6 |
C14—C1—H1 | 106.3 | C18—C19—H191 | 108.6 |
C17—C1—H1 | 106.3 | C18—C19—H192 | 108.6 |
C1—C2—H2 | 107.6 | H191—C19—H192 | 109.5 |
C3—C2—H2 | 107.6 | C14—C20—H201 | 109.5 |
C11—C2—H2 | 107.6 | C14—C20—H202 | 109.5 |
C2—C3—H3 | 118.5 | C14—C20—H203 | 109.5 |
C4—C3—H3 | 118.5 | H201—C20—H202 | 109.5 |
C3—C4—H4 | 118.7 | H201—C20—H203 | 109.5 |
C5—C4—H4 | 118.7 | H202—C20—H203 | 109.5 |
C5—C6—H6 | 117.7 | ||
C15—O2—C18—O3 | 0.1 (2) | C10—C5—C6—C7 | −0.1 (2) |
C15—O2—C18—C19 | 179.30 (14) | C5—C6—C7—O1 | −178.1 (2) |
C18—O2—C15—C14 | −91.30 (19) | C5—C6—C7—C8 | 1.3 (3) |
C18—O2—C15—C16 | 151.44 (16) | O1—C7—C8—C9 | −155.8 (2) |
C2—C1—C14—C13 | −60.89 (19) | C6—C7—C8—C9 | 24.8 (2) |
C2—C1—C14—C15 | 177.76 (14) | C7—C8—C9—C10 | −51.8 (2) |
C2—C1—C14—C20 | 62.56 (18) | C8—C9—C10—C5 | 51.3 (2) |
C14—C1—C2—C3 | −173.08 (15) | C8—C9—C10—C11 | 175.79 (15) |
C14—C1—C2—C11 | 62.58 (18) | C5—C10—C11—C2 | −52.86 (19) |
C2—C1—C17—C16 | −161.68 (17) | C5—C10—C11—C12 | −177.97 (15) |
C17—C1—C2—C3 | −49.7 (2) | C9—C10—C11—C2 | −177.16 (14) |
C17—C1—C2—C11 | −174.03 (15) | C9—C10—C11—C12 | 57.7 (2) |
C14—C1—C17—C16 | −34.53 (19) | C2—C11—C12—C13 | 53.0 (2) |
C17—C1—C14—C13 | 166.97 (15) | C10—C11—C12—C13 | 179.01 (15) |
C17—C1—C14—C15 | 45.62 (17) | C11—C12—C13—C14 | −52.5 (2) |
C17—C1—C14—C20 | −69.58 (18) | C12—C13—C14—C1 | 54.00 (19) |
C1—C2—C3—C4 | −146.81 (19) | C12—C13—C14—C15 | 163.99 (15) |
C1—C2—C11—C10 | 176.38 (13) | C12—C13—C14—C20 | −70.28 (18) |
C1—C2—C11—C12 | −56.64 (18) | C1—C14—C15—O2 | −157.87 (13) |
C3—C2—C11—C10 | 49.97 (19) | C1—C14—C15—C16 | −39.84 (17) |
C3—C2—C11—C12 | 176.95 (15) | C13—C14—C15—O2 | 86.74 (18) |
C11—C2—C3—C4 | −23.7 (2) | C13—C14—C15—C16 | −155.22 (15) |
C2—C3—C4—C5 | 0.1 (2) | C20—C14—C15—O2 | −40.03 (18) |
C3—C4—C5—C6 | 179.5 (2) | C20—C14—C15—C16 | 78.00 (17) |
C3—C4—C5—C10 | −3.3 (2) | O2—C15—C16—C17 | 142.74 (16) |
C4—C5—C6—C7 | 176.97 (19) | C14—C15—C16—C17 | 19.8 (2) |
C4—C5—C10—C9 | 156.42 (17) | C15—C16—C17—C1 | 9.0 (2) |
C4—C5—C10—C11 | 29.8 (2) | O2—C18—C19—Cl1 | 168.34 (12) |
C6—C5—C10—C9 | −26.4 (2) | O3—C18—C19—Cl1 | −12.5 (2) |
C6—C5—C10—C11 | −152.97 (18) |
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