


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012118/su5512sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012118/su5512Isup2.hkl |
![]() | Chemdraw file https://doi.org/10.1107/S2056989019012118/su5512Isup3.cdx |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019012118/su5512sup4.pdf |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019012118/su5512sup5.pdf |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019012118/su5512sup6.pdf |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019012118/su5512sup7.pdf |
CCDC reference: 1950725
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00426 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.725 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 17 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 8 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C25H12Cl6O4 | F(000) = 1184 |
Mr = 589.05 | Dx = 1.661 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ybc | Cell parameters from 28116 reflections |
a = 17.9667 (4) Å | θ = 3.0–68.3° |
b = 7.9150 (1) Å | µ = 6.95 mm−1 |
c = 17.6995 (5) Å | T = 193 K |
β = 110.673 (1)° | Platelet, yellow |
V = 2354.91 (9) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 4300 independent reflections |
Radiation source: rotaing anode | 3737 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.110 |
Detector resolution: 10.000 pixels mm-1 | θmax = 68.3°, θmin = 5.1° |
ω scans | h = −21→21 |
Absorption correction: numerical (NUMABS; Higashi, 1999) | k = −9→9 |
Tmin = 0.168, Tmax = 0.337 | l = −21→21 |
41619 measured reflections |
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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0625P)2 + 1.5934P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4300 reflections | Δρmax = 0.50 e Å−3 |
319 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00166 (17) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.13592 (4) | 0.62787 (10) | 0.05084 (5) | 0.0543 (2) | |
Cl2 | 0.00708 (5) | 0.06020 (13) | 0.10904 (5) | 0.0645 (3) | |
Cl3 | 0.32240 (4) | 0.09099 (9) | 0.20159 (4) | 0.0477 (2) | |
Cl4 | 0.09824 (5) | 0.59970 (12) | 0.24340 (5) | 0.0634 (3) | |
Cl5 | 0.10530 (6) | 1.19664 (13) | 0.39062 (6) | 0.0703 (3) | |
Cl6 | 0.37761 (4) | 0.90853 (10) | 0.39693 (4) | 0.0512 (2) | |
O1 | 0.30235 (12) | 0.5154 (3) | 0.07105 (12) | 0.0517 (5) | |
O2 | 0.26606 (11) | 0.6928 (3) | 0.20713 (11) | 0.0422 (5) | |
O3 | 0.44648 (13) | 0.4173 (3) | 0.11247 (14) | 0.0589 (6) | |
H3A | 0.4035 | 0.4583 | 0.0812 | 0.071* | |
O4 | 0.26290 (15) | 0.5184 (3) | 0.41656 (12) | 0.0613 (6) | |
C1 | 0.37736 (16) | 0.4494 (4) | 0.20717 (17) | 0.0413 (6) | |
C2 | 0.44482 (17) | 0.4097 (4) | 0.1885 (2) | 0.0492 (7) | |
C3 | 0.51384 (17) | 0.3460 (4) | 0.2480 (2) | 0.0571 (9) | |
H3 | 0.5593 | 0.3195 | 0.2347 | 0.069* | |
C4 | 0.51548 (18) | 0.3226 (4) | 0.3237 (2) | 0.0584 (9) | |
H4 | 0.5612 | 0.2728 | 0.3625 | 0.070* | |
C5 | 0.45068 (18) | 0.3702 (4) | 0.34747 (19) | 0.0509 (8) | |
C6 | 0.4532 (2) | 0.3417 (4) | 0.42678 (19) | 0.0604 (9) | |
H6 | 0.4992 | 0.2905 | 0.4644 | 0.072* | |
C7 | 0.3920 (2) | 0.3850 (4) | 0.45164 (19) | 0.0583 (9) | |
H7 | 0.3938 | 0.3581 | 0.5046 | 0.070* | |
C8 | 0.3262 (2) | 0.4701 (4) | 0.39744 (17) | 0.0511 (8) | |
C9 | 0.32242 (16) | 0.5103 (4) | 0.31878 (16) | 0.0409 (6) | |
C10 | 0.38174 (16) | 0.4428 (4) | 0.28935 (17) | 0.0418 (6) | |
C11 | 0.30243 (16) | 0.4589 (4) | 0.13587 (16) | 0.0403 (6) | |
C12 | 0.22876 (15) | 0.3656 (4) | 0.13489 (15) | 0.0379 (6) | |
C13 | 0.15151 (17) | 0.4292 (4) | 0.09543 (16) | 0.0431 (7) | |
C14 | 0.08428 (16) | 0.3378 (4) | 0.08818 (16) | 0.0464 (7) | |
H14 | 0.0331 | 0.3860 | 0.0625 | 0.056* | |
C15 | 0.09164 (16) | 0.1760 (4) | 0.11843 (17) | 0.0458 (7) | |
C16 | 0.16576 (17) | 0.1018 (4) | 0.15470 (16) | 0.0457 (7) | |
H16 | 0.1706 | −0.0115 | 0.1736 | 0.055* | |
C17 | 0.23220 (15) | 0.1976 (4) | 0.16237 (15) | 0.0386 (6) | |
C18 | 0.27267 (15) | 0.6515 (4) | 0.27587 (16) | 0.0395 (6) | |
C19 | 0.23318 (16) | 0.7726 (4) | 0.31692 (15) | 0.0398 (6) | |
C20 | 0.15062 (16) | 0.7704 (4) | 0.29719 (16) | 0.0452 (7) | |
C21 | 0.11036 (18) | 0.8971 (4) | 0.31971 (18) | 0.0500 (7) | |
H21 | 0.0543 | 0.8925 | 0.3057 | 0.060* | |
C22 | 0.15427 (18) | 1.0321 (4) | 0.36357 (18) | 0.0503 (7) | |
C23 | 0.23617 (18) | 1.0364 (4) | 0.38688 (17) | 0.0480 (7) | |
H23 | 0.2656 | 1.1279 | 0.4180 | 0.058* | |
C24 | 0.27431 (16) | 0.9059 (4) | 0.36436 (16) | 0.0424 (6) | |
C25 | 0.2684 (3) | 0.5207 (6) | 0.4997 (2) | 0.0862 (14) | |
H25A | 0.2202 | 0.5722 | 0.5036 | 0.103* | |
H25B | 0.3150 | 0.5868 | 0.5317 | 0.103* | |
H25C | 0.2736 | 0.4048 | 0.5205 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0419 (4) | 0.0540 (5) | 0.0572 (4) | 0.0039 (3) | 0.0054 (3) | 0.0116 (3) |
Cl2 | 0.0421 (4) | 0.0769 (6) | 0.0739 (5) | −0.0167 (4) | 0.0198 (4) | 0.0057 (4) |
Cl3 | 0.0375 (4) | 0.0437 (4) | 0.0543 (4) | 0.0019 (3) | 0.0067 (3) | 0.0027 (3) |
Cl4 | 0.0434 (4) | 0.0766 (6) | 0.0739 (5) | −0.0202 (4) | 0.0255 (4) | −0.0219 (4) |
Cl5 | 0.0680 (6) | 0.0673 (6) | 0.0806 (6) | 0.0184 (5) | 0.0324 (5) | −0.0061 (4) |
Cl6 | 0.0357 (4) | 0.0568 (5) | 0.0525 (4) | −0.0032 (3) | 0.0049 (3) | −0.0037 (3) |
O1 | 0.0434 (11) | 0.0682 (15) | 0.0466 (11) | −0.0015 (10) | 0.0198 (9) | 0.0071 (10) |
O2 | 0.0418 (10) | 0.0444 (11) | 0.0401 (10) | 0.0018 (9) | 0.0139 (8) | 0.0033 (8) |
O3 | 0.0461 (12) | 0.0644 (16) | 0.0731 (15) | 0.0009 (11) | 0.0297 (11) | −0.0043 (12) |
O4 | 0.0764 (16) | 0.0679 (16) | 0.0452 (12) | −0.0017 (13) | 0.0284 (11) | 0.0088 (11) |
C1 | 0.0307 (13) | 0.0372 (15) | 0.0531 (16) | −0.0021 (11) | 0.0111 (12) | −0.0008 (12) |
C2 | 0.0356 (15) | 0.0438 (18) | 0.0666 (19) | −0.0069 (13) | 0.0161 (14) | −0.0040 (14) |
C3 | 0.0312 (15) | 0.0483 (19) | 0.086 (2) | −0.0005 (13) | 0.0137 (15) | −0.0100 (17) |
C4 | 0.0330 (15) | 0.0430 (18) | 0.079 (2) | 0.0006 (13) | −0.0053 (15) | −0.0020 (16) |
C5 | 0.0391 (16) | 0.0430 (18) | 0.0542 (17) | −0.0043 (13) | −0.0037 (13) | −0.0053 (13) |
C6 | 0.057 (2) | 0.0471 (19) | 0.0503 (18) | −0.0023 (16) | −0.0145 (15) | 0.0031 (14) |
C7 | 0.069 (2) | 0.052 (2) | 0.0395 (16) | −0.0097 (17) | 0.0013 (15) | 0.0044 (14) |
C8 | 0.0587 (19) | 0.0451 (18) | 0.0425 (15) | −0.0083 (15) | 0.0093 (14) | 0.0011 (13) |
C9 | 0.0370 (14) | 0.0414 (16) | 0.0382 (14) | −0.0050 (12) | 0.0057 (11) | 0.0009 (12) |
C10 | 0.0332 (14) | 0.0337 (15) | 0.0497 (15) | −0.0041 (11) | 0.0036 (11) | 0.0001 (12) |
C11 | 0.0361 (14) | 0.0421 (16) | 0.0414 (14) | 0.0020 (12) | 0.0123 (11) | −0.0003 (12) |
C12 | 0.0336 (13) | 0.0445 (16) | 0.0332 (13) | −0.0010 (12) | 0.0090 (10) | −0.0010 (11) |
C13 | 0.0384 (14) | 0.0486 (17) | 0.0371 (14) | 0.0000 (13) | 0.0068 (11) | 0.0021 (12) |
C14 | 0.0324 (14) | 0.061 (2) | 0.0421 (15) | 0.0021 (13) | 0.0085 (11) | −0.0004 (13) |
C15 | 0.0350 (14) | 0.059 (2) | 0.0423 (15) | −0.0096 (13) | 0.0124 (11) | −0.0020 (13) |
C16 | 0.0418 (16) | 0.0502 (19) | 0.0429 (15) | −0.0053 (13) | 0.0121 (12) | 0.0032 (13) |
C17 | 0.0329 (13) | 0.0451 (16) | 0.0351 (13) | 0.0006 (12) | 0.0088 (10) | −0.0021 (11) |
C18 | 0.0312 (13) | 0.0440 (16) | 0.0398 (14) | −0.0047 (12) | 0.0080 (11) | 0.0000 (12) |
C19 | 0.0358 (13) | 0.0473 (17) | 0.0367 (13) | −0.0022 (12) | 0.0132 (11) | 0.0027 (12) |
C20 | 0.0366 (14) | 0.0576 (19) | 0.0413 (14) | −0.0087 (13) | 0.0138 (11) | −0.0023 (13) |
C21 | 0.0383 (15) | 0.067 (2) | 0.0480 (16) | 0.0024 (14) | 0.0186 (13) | 0.0005 (15) |
C22 | 0.0510 (17) | 0.055 (2) | 0.0489 (16) | 0.0111 (15) | 0.0225 (14) | 0.0034 (14) |
C23 | 0.0494 (17) | 0.0501 (18) | 0.0421 (15) | 0.0006 (14) | 0.0132 (13) | −0.0025 (13) |
C24 | 0.0339 (14) | 0.0523 (18) | 0.0383 (14) | −0.0010 (12) | 0.0096 (11) | 0.0015 (12) |
C25 | 0.127 (4) | 0.090 (3) | 0.049 (2) | −0.016 (3) | 0.040 (2) | −0.003 (2) |
Cl1—C13 | 1.737 (3) | C7—H7 | 0.9500 |
Cl2—C15 | 1.731 (3) | C8—C9 | 1.406 (4) |
Cl3—C17 | 1.740 (3) | C9—C10 | 1.444 (4) |
Cl4—C20 | 1.728 (3) | C9—C18 | 1.465 (4) |
Cl5—C22 | 1.731 (3) | C11—C12 | 1.511 (4) |
Cl6—C24 | 1.738 (3) | C12—C13 | 1.408 (4) |
O1—C11 | 1.231 (3) | C12—C17 | 1.409 (4) |
O2—C18 | 1.224 (3) | C13—C14 | 1.374 (4) |
O3—C2 | 1.358 (4) | C14—C15 | 1.376 (5) |
O3—H3A | 0.8400 | C14—H14 | 0.9500 |
O4—C8 | 1.351 (4) | C15—C16 | 1.388 (4) |
O4—C25 | 1.441 (4) | C16—C17 | 1.380 (4) |
C1—C2 | 1.400 (4) | C16—H16 | 0.9500 |
C1—C10 | 1.430 (4) | C18—C19 | 1.522 (4) |
C1—C11 | 1.487 (4) | C19—C24 | 1.388 (4) |
C2—C3 | 1.407 (4) | C19—C20 | 1.399 (4) |
C3—C4 | 1.342 (5) | C20—C21 | 1.375 (4) |
C3—H3 | 0.9500 | C21—C22 | 1.391 (5) |
C4—C5 | 1.421 (5) | C21—H21 | 0.9500 |
C4—H4 | 0.9500 | C22—C23 | 1.381 (4) |
C5—C6 | 1.407 (5) | C23—C24 | 1.374 (4) |
C5—C10 | 1.422 (4) | C23—H23 | 0.9500 |
C6—C7 | 1.365 (5) | C25—H25A | 0.9800 |
C6—H6 | 0.9500 | C25—H25B | 0.9800 |
C7—C8 | 1.403 (5) | C25—H25C | 0.9800 |
C2—O3—H3A | 109.5 | C12—C13—Cl1 | 121.4 (2) |
C8—O4—C25 | 120.0 (3) | C13—C14—C15 | 119.5 (3) |
C2—C1—C10 | 119.4 (3) | C13—C14—H14 | 120.2 |
C2—C1—C11 | 114.3 (3) | C15—C14—H14 | 120.2 |
C10—C1—C11 | 125.0 (2) | C14—C15—C16 | 121.2 (3) |
O3—C2—C1 | 123.2 (3) | C14—C15—Cl2 | 119.6 (2) |
O3—C2—C3 | 115.8 (3) | C16—C15—Cl2 | 119.1 (3) |
C1—C2—C3 | 120.8 (3) | C17—C16—C15 | 117.9 (3) |
C4—C3—C2 | 120.0 (3) | C17—C16—H16 | 121.0 |
C4—C3—H3 | 120.0 | C15—C16—H16 | 121.0 |
C2—C3—H3 | 120.0 | C16—C17—C12 | 123.6 (3) |
C3—C4—C5 | 121.8 (3) | C16—C17—Cl3 | 115.1 (2) |
C3—C4—H4 | 119.1 | C12—C17—Cl3 | 121.1 (2) |
C5—C4—H4 | 119.1 | O2—C18—C9 | 123.1 (3) |
C6—C5—C4 | 120.7 (3) | O2—C18—C19 | 114.1 (2) |
C6—C5—C10 | 120.0 (3) | C9—C18—C19 | 122.4 (2) |
C4—C5—C10 | 119.2 (3) | C24—C19—C20 | 116.9 (3) |
C7—C6—C5 | 122.4 (3) | C24—C19—C18 | 122.0 (2) |
C7—C6—H6 | 118.8 | C20—C19—C18 | 120.3 (2) |
C5—C6—H6 | 118.8 | C21—C20—C19 | 122.6 (3) |
C6—C7—C8 | 118.7 (3) | C21—C20—Cl4 | 119.3 (2) |
C6—C7—H7 | 120.7 | C19—C20—Cl4 | 118.1 (2) |
C8—C7—H7 | 120.7 | C20—C21—C22 | 118.0 (3) |
O4—C8—C7 | 123.0 (3) | C20—C21—H21 | 121.0 |
O4—C8—C9 | 115.7 (3) | C22—C21—H21 | 121.0 |
C7—C8—C9 | 121.3 (3) | C23—C22—C21 | 121.3 (3) |
C8—C9—C10 | 119.3 (3) | C23—C22—Cl5 | 119.4 (3) |
C8—C9—C18 | 119.6 (3) | C21—C22—Cl5 | 119.3 (2) |
C10—C9—C18 | 119.2 (2) | C24—C23—C22 | 118.9 (3) |
C5—C10—C1 | 118.1 (3) | C24—C23—H23 | 120.6 |
C5—C10—C9 | 117.0 (3) | C22—C23—H23 | 120.6 |
C1—C10—C9 | 124.8 (2) | C23—C24—C19 | 122.2 (3) |
O1—C11—C1 | 120.8 (3) | C23—C24—Cl6 | 118.6 (2) |
O1—C11—C12 | 117.0 (2) | C19—C24—Cl6 | 119.2 (2) |
C1—C11—C12 | 120.8 (2) | O4—C25—H25A | 109.5 |
C13—C12—C17 | 115.1 (3) | O4—C25—H25B | 109.5 |
C13—C12—C11 | 122.5 (3) | H25A—C25—H25B | 109.5 |
C17—C12—C11 | 121.7 (2) | O4—C25—H25C | 109.5 |
C14—C13—C12 | 122.6 (3) | H25A—C25—H25C | 109.5 |
C14—C13—Cl1 | 116.0 (2) | H25B—C25—H25C | 109.5 |
C10—C1—C2—O3 | −178.1 (3) | C17—C12—C13—C14 | 3.5 (4) |
C11—C1—C2—O3 | 14.5 (4) | C11—C12—C13—C14 | 174.0 (3) |
C10—C1—C2—C3 | 7.0 (4) | C17—C12—C13—Cl1 | −175.0 (2) |
C11—C1—C2—C3 | −160.4 (3) | C11—C12—C13—Cl1 | −4.6 (4) |
O3—C2—C3—C4 | −175.3 (3) | C12—C13—C14—C15 | −1.8 (4) |
C1—C2—C3—C4 | 0.0 (5) | Cl1—C13—C14—C15 | 176.8 (2) |
C2—C3—C4—C5 | −3.9 (5) | C13—C14—C15—C16 | −1.4 (4) |
C3—C4—C5—C6 | 178.9 (3) | C13—C14—C15—Cl2 | −179.7 (2) |
C3—C4—C5—C10 | 0.8 (5) | C14—C15—C16—C17 | 2.5 (4) |
C4—C5—C6—C7 | −179.7 (3) | Cl2—C15—C16—C17 | −179.2 (2) |
C10—C5—C6—C7 | −1.6 (5) | C15—C16—C17—C12 | −0.5 (4) |
C5—C6—C7—C8 | −3.9 (5) | C15—C16—C17—Cl3 | −175.5 (2) |
C25—O4—C8—C7 | 15.0 (5) | C13—C12—C17—C16 | −2.3 (4) |
C25—O4—C8—C9 | −165.1 (3) | C11—C12—C17—C16 | −172.9 (3) |
C6—C7—C8—O4 | −179.8 (3) | C13—C12—C17—Cl3 | 172.3 (2) |
C6—C7—C8—C9 | 0.2 (5) | C11—C12—C17—Cl3 | 1.8 (4) |
O4—C8—C9—C10 | −171.3 (3) | C8—C9—C18—O2 | −179.4 (3) |
C7—C8—C9—C10 | 8.7 (4) | C10—C9—C18—O2 | 16.3 (4) |
O4—C8—C9—C18 | 24.5 (4) | C8—C9—C18—C19 | 8.5 (4) |
C7—C8—C9—C18 | −155.6 (3) | C10—C9—C18—C19 | −155.8 (3) |
C6—C5—C10—C1 | −172.0 (3) | O2—C18—C19—C24 | −91.9 (3) |
C4—C5—C10—C1 | 6.1 (4) | C9—C18—C19—C24 | 80.8 (4) |
C6—C5—C10—C9 | 10.2 (4) | O2—C18—C19—C20 | 77.3 (3) |
C4—C5—C10—C9 | −171.7 (3) | C9—C18—C19—C20 | −109.9 (3) |
C2—C1—C10—C5 | −9.9 (4) | C24—C19—C20—C21 | 3.1 (4) |
C11—C1—C10—C5 | 156.1 (3) | C18—C19—C20—C21 | −166.7 (3) |
C2—C1—C10—C9 | 167.7 (3) | C24—C19—C20—Cl4 | −176.2 (2) |
C11—C1—C10—C9 | −26.3 (4) | C18—C19—C20—Cl4 | 14.1 (4) |
C8—C9—C10—C5 | −13.6 (4) | C19—C20—C21—C22 | 0.2 (4) |
C18—C9—C10—C5 | 150.6 (3) | Cl4—C20—C21—C22 | 179.5 (2) |
C8—C9—C10—C1 | 168.7 (3) | C20—C21—C22—C23 | −2.6 (4) |
C18—C9—C10—C1 | −27.0 (4) | C20—C21—C22—Cl5 | 178.3 (2) |
C2—C1—C11—O1 | −36.1 (4) | C21—C22—C23—C24 | 1.6 (4) |
C10—C1—C11—O1 | 157.3 (3) | Cl5—C22—C23—C24 | −179.3 (2) |
C2—C1—C11—C12 | 130.2 (3) | C22—C23—C24—C19 | 2.0 (4) |
C10—C1—C11—C12 | −36.4 (4) | C22—C23—C24—Cl6 | −177.8 (2) |
O1—C11—C12—C13 | −47.0 (4) | C20—C19—C24—C23 | −4.2 (4) |
C1—C11—C12—C13 | 146.3 (3) | C18—C19—C24—C23 | 165.4 (3) |
O1—C11—C12—C17 | 122.9 (3) | C20—C19—C24—Cl6 | 175.5 (2) |
C1—C11—C12—C17 | −43.9 (4) | C18—C19—C24—Cl6 | −14.9 (4) |