Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020907/ac6064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020907/ac6064Isup2.hkl |
CCDC reference: 226949
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C33H22Cl4N2O3 | Dx = 1.411 Mg m−3 |
Mr = 636.33 | Melting point = 527–529 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.464 (3) Å | Cell parameters from 950 reflections |
b = 13.377 (3) Å | θ = 2.9–25.1° |
c = 17.080 (4) Å | µ = 0.43 mm−1 |
β = 114.954 (4)° | T = 293 K |
V = 2996.2 (13) Å3 | Block, colorless |
Z = 4 | 0.28 × 0.22 × 0.20 mm |
F(000) = 1304 |
Bruker SMART CCD area-detector diffractometer | 6135 independent reflections |
Radiation source: fine-focus sealed tube | 3963 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −18→18 |
Tmin = 0.799, Tmax = 0.917 | k = −16→16 |
24667 measured reflections | l = −21→21 |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.56 e Å−3 |
6135 reflections | Δρmin = −0.24 e Å−3 |
379 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.23019 (6) | 0.31869 (6) | 0.18548 (5) | 0.0615 (2) | |
Cl2 | 0.57597 (6) | 0.20161 (6) | 0.16029 (6) | 0.0754 (3) | |
Cl3 | −0.00792 (7) | 0.76867 (7) | 0.04860 (6) | 0.0843 (3) | |
Cl4 | 0.02273 (8) | 0.84458 (8) | −0.25014 (5) | 0.0881 (3) | |
N1 | 0.45130 (16) | 0.41362 (16) | 0.14226 (14) | 0.0502 (5) | |
N2 | 0.03769 (16) | 0.64779 (17) | −0.13501 (15) | 0.0559 (6) | |
O1 | 0.2319 (2) | 0.53014 (17) | 0.09186 (16) | 0.0944 (8) | |
C1 | 0.2481 (2) | 0.53320 (18) | 0.02904 (18) | 0.0502 (6) | |
O2 | 0.42326 (14) | 0.48814 (12) | 0.07763 (11) | 0.0536 (5) | |
O3 | 0.11421 (14) | 0.57319 (13) | −0.10797 (13) | 0.0618 (5) | |
C2 | 0.32208 (18) | 0.46475 (17) | 0.01073 (15) | 0.0406 (5) | |
C3 | 0.3168 (2) | 0.50316 (18) | −0.07489 (16) | 0.0457 (6) | |
H3A | 0.2654 | 0.4674 | −0.1230 | 0.055* | |
H3B | 0.3822 | 0.4957 | −0.0776 | 0.055* | |
C4 | 0.2884 (2) | 0.61410 (18) | −0.07657 (17) | 0.0451 (6) | |
H4A | 0.3472 | 0.6537 | −0.0405 | 0.054* | |
H4B | 0.2607 | 0.6403 | −0.1350 | 0.054* | |
C5 | 0.20851 (17) | 0.61382 (17) | −0.04101 (15) | 0.0399 (5) | |
C6 | 0.30690 (17) | 0.35330 (16) | 0.02414 (14) | 0.0362 (5) | |
H6 | 0.2394 | 0.3430 | 0.0233 | 0.043* | |
C7 | 0.38857 (18) | 0.34139 (17) | 0.11563 (15) | 0.0386 (5) | |
C8 | 0.40216 (19) | 0.25495 (17) | 0.17440 (15) | 0.0426 (6) | |
C9 | 0.3317 (2) | 0.23762 (18) | 0.20899 (16) | 0.0472 (6) | |
C10 | 0.3417 (3) | 0.1587 (2) | 0.26463 (17) | 0.0606 (8) | |
H10 | 0.2925 | 0.1479 | 0.2853 | 0.073* | |
C11 | 0.4247 (3) | 0.0969 (2) | 0.28881 (19) | 0.0691 (9) | |
H11 | 0.4322 | 0.0444 | 0.3267 | 0.083* | |
C12 | 0.4967 (3) | 0.1120 (2) | 0.25750 (18) | 0.0646 (8) | |
H12 | 0.5534 | 0.0703 | 0.2747 | 0.077* | |
C13 | 0.4848 (2) | 0.18960 (19) | 0.20013 (17) | 0.0513 (6) | |
C14 | 0.32116 (18) | 0.28307 (17) | −0.03932 (15) | 0.0400 (5) | |
C15 | 0.4149 (2) | 0.2774 (2) | −0.04358 (19) | 0.0593 (7) | |
H15 | 0.4693 | 0.3156 | −0.0061 | 0.071* | |
C16 | 0.4280 (3) | 0.2163 (3) | −0.1023 (2) | 0.0808 (10) | |
H16 | 0.4913 | 0.2128 | −0.1041 | 0.097* | |
C17 | 0.3494 (4) | 0.1607 (3) | −0.1579 (2) | 0.0874 (12) | |
H17 | 0.3590 | 0.1191 | −0.1974 | 0.105* | |
C18 | 0.2563 (3) | 0.1654 (2) | −0.1561 (2) | 0.0810 (11) | |
H18 | 0.2024 | 0.1276 | −0.1947 | 0.097* | |
C19 | 0.2416 (2) | 0.2271 (2) | −0.09595 (18) | 0.0576 (7) | |
H19 | 0.1781 | 0.2301 | −0.0945 | 0.069* | |
C20 | 0.17402 (17) | 0.70944 (16) | −0.01220 (15) | 0.0392 (5) | |
H20 | 0.1634 | 0.6926 | 0.0392 | 0.047* | |
C21 | 0.06993 (18) | 0.72293 (18) | −0.08555 (16) | 0.0426 (6) | |
C22 | 0.00438 (18) | 0.81248 (18) | −0.10080 (16) | 0.0449 (6) | |
C23 | −0.0355 (2) | 0.8406 (2) | −0.04252 (18) | 0.0546 (7) | |
C24 | −0.0983 (2) | 0.9229 (3) | −0.0562 (2) | 0.0715 (9) | |
H24 | −0.1249 | 0.9393 | −0.0168 | 0.086* | |
C25 | −0.1209 (2) | 0.9800 (2) | −0.1286 (2) | 0.0770 (10) | |
H25 | −0.1627 | 1.0357 | −0.1381 | 0.092* | |
C26 | −0.0828 (2) | 0.9560 (2) | −0.1870 (2) | 0.0714 (9) | |
H26 | −0.0980 | 0.9955 | −0.2357 | 0.086* | |
C27 | −0.0216 (2) | 0.8729 (2) | −0.17338 (18) | 0.0562 (7) | |
C28 | 0.24409 (18) | 0.79874 (18) | 0.01072 (17) | 0.0454 (6) | |
C29 | 0.2960 (2) | 0.8253 (2) | 0.0966 (2) | 0.0612 (8) | |
H29 | 0.2876 | 0.7872 | 0.1387 | 0.073* | |
C30 | 0.3596 (3) | 0.9068 (3) | 0.1210 (3) | 0.0871 (12) | |
H30 | 0.3948 | 0.9230 | 0.1791 | 0.105* | |
C31 | 0.3707 (3) | 0.9635 (3) | 0.0599 (3) | 0.0915 (13) | |
H31 | 0.4120 | 1.0199 | 0.0762 | 0.110* | |
C32 | 0.3214 (3) | 0.9385 (2) | −0.0262 (3) | 0.0862 (11) | |
H32 | 0.3305 | 0.9769 | −0.0677 | 0.103* | |
C33 | 0.2576 (2) | 0.8549 (2) | −0.0506 (2) | 0.0676 (8) | |
H33 | 0.2243 | 0.8375 | −0.1085 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0643 (4) | 0.0681 (5) | 0.0639 (4) | 0.0040 (4) | 0.0384 (4) | 0.0056 (4) |
Cl2 | 0.0602 (5) | 0.0776 (5) | 0.0885 (6) | 0.0218 (4) | 0.0316 (4) | 0.0107 (4) |
Cl3 | 0.0819 (6) | 0.1094 (7) | 0.0839 (6) | 0.0303 (5) | 0.0565 (5) | 0.0311 (5) |
Cl4 | 0.1099 (7) | 0.1027 (7) | 0.0564 (5) | 0.0318 (6) | 0.0395 (5) | 0.0178 (4) |
N1 | 0.0540 (13) | 0.0419 (12) | 0.0494 (13) | −0.0012 (10) | 0.0166 (11) | 0.0016 (10) |
N2 | 0.0441 (12) | 0.0483 (13) | 0.0651 (15) | 0.0044 (11) | 0.0131 (11) | −0.0094 (12) |
O1 | 0.157 (2) | 0.0762 (15) | 0.0968 (17) | 0.0591 (15) | 0.0988 (17) | 0.0367 (13) |
C1 | 0.0672 (18) | 0.0383 (14) | 0.0583 (16) | 0.0107 (12) | 0.0392 (15) | 0.0053 (12) |
O2 | 0.0563 (11) | 0.0402 (10) | 0.0559 (11) | −0.0075 (8) | 0.0155 (9) | 0.0046 (8) |
O3 | 0.0476 (11) | 0.0413 (10) | 0.0824 (14) | 0.0016 (8) | 0.0137 (10) | −0.0198 (10) |
C2 | 0.0439 (14) | 0.0365 (13) | 0.0431 (14) | 0.0048 (11) | 0.0201 (12) | 0.0014 (11) |
C3 | 0.0519 (15) | 0.0440 (14) | 0.0515 (15) | 0.0064 (12) | 0.0317 (13) | 0.0044 (12) |
C4 | 0.0534 (15) | 0.0394 (13) | 0.0483 (15) | 0.0013 (12) | 0.0270 (13) | 0.0056 (11) |
C5 | 0.0389 (13) | 0.0338 (12) | 0.0453 (14) | −0.0003 (10) | 0.0162 (11) | −0.0004 (10) |
C6 | 0.0358 (12) | 0.0341 (12) | 0.0415 (13) | 0.0026 (10) | 0.0189 (11) | 0.0012 (10) |
C7 | 0.0393 (13) | 0.0364 (13) | 0.0418 (13) | 0.0022 (11) | 0.0188 (11) | −0.0026 (10) |
C8 | 0.0504 (15) | 0.0361 (13) | 0.0360 (13) | −0.0017 (11) | 0.0130 (11) | −0.0033 (10) |
C9 | 0.0594 (16) | 0.0421 (14) | 0.0382 (13) | −0.0051 (12) | 0.0187 (13) | −0.0052 (11) |
C10 | 0.085 (2) | 0.0511 (17) | 0.0476 (16) | −0.0133 (16) | 0.0292 (16) | −0.0009 (13) |
C11 | 0.106 (3) | 0.0436 (17) | 0.0501 (18) | −0.0020 (18) | 0.0256 (18) | 0.0057 (13) |
C12 | 0.083 (2) | 0.0400 (16) | 0.0513 (17) | 0.0111 (15) | 0.0097 (17) | 0.0008 (13) |
C13 | 0.0571 (16) | 0.0408 (14) | 0.0471 (15) | 0.0019 (12) | 0.0132 (13) | −0.0037 (12) |
C14 | 0.0449 (14) | 0.0365 (13) | 0.0394 (13) | 0.0073 (11) | 0.0185 (12) | 0.0052 (11) |
C15 | 0.0602 (17) | 0.0631 (18) | 0.0636 (18) | 0.0135 (14) | 0.0348 (15) | 0.0020 (15) |
C16 | 0.105 (3) | 0.083 (2) | 0.077 (2) | 0.039 (2) | 0.061 (2) | 0.010 (2) |
C17 | 0.148 (4) | 0.069 (2) | 0.062 (2) | 0.040 (2) | 0.061 (3) | 0.0054 (18) |
C18 | 0.117 (3) | 0.056 (2) | 0.0535 (19) | 0.002 (2) | 0.020 (2) | −0.0128 (15) |
C19 | 0.0680 (19) | 0.0476 (16) | 0.0526 (16) | 0.0008 (14) | 0.0210 (15) | −0.0027 (13) |
C20 | 0.0389 (13) | 0.0331 (12) | 0.0427 (13) | 0.0036 (10) | 0.0146 (11) | 0.0001 (10) |
C21 | 0.0394 (13) | 0.0387 (13) | 0.0481 (15) | 0.0017 (11) | 0.0169 (12) | 0.0003 (11) |
C22 | 0.0362 (13) | 0.0433 (14) | 0.0490 (15) | 0.0035 (11) | 0.0120 (12) | −0.0005 (12) |
C23 | 0.0442 (15) | 0.0568 (17) | 0.0607 (17) | 0.0083 (13) | 0.0203 (13) | 0.0041 (14) |
C24 | 0.0581 (19) | 0.078 (2) | 0.080 (2) | 0.0178 (17) | 0.0303 (17) | −0.0074 (19) |
C25 | 0.062 (2) | 0.061 (2) | 0.093 (3) | 0.0279 (16) | 0.0178 (19) | 0.0034 (19) |
C26 | 0.072 (2) | 0.0614 (19) | 0.067 (2) | 0.0227 (17) | 0.0158 (17) | 0.0139 (16) |
C27 | 0.0530 (16) | 0.0562 (17) | 0.0518 (16) | 0.0096 (14) | 0.0146 (13) | 0.0026 (13) |
C28 | 0.0411 (14) | 0.0332 (13) | 0.0583 (16) | 0.0048 (11) | 0.0175 (13) | −0.0058 (12) |
C29 | 0.0533 (17) | 0.0611 (18) | 0.070 (2) | −0.0025 (14) | 0.0271 (15) | −0.0242 (15) |
C30 | 0.073 (2) | 0.081 (3) | 0.108 (3) | −0.020 (2) | 0.039 (2) | −0.053 (2) |
C31 | 0.074 (2) | 0.050 (2) | 0.148 (4) | −0.0169 (17) | 0.044 (3) | −0.042 (2) |
C32 | 0.081 (2) | 0.0472 (19) | 0.133 (4) | −0.0005 (17) | 0.048 (2) | 0.015 (2) |
C33 | 0.0633 (19) | 0.0453 (17) | 0.083 (2) | −0.0061 (14) | 0.0202 (17) | 0.0055 (16) |
Cl1—C9 | 1.731 (3) | C14—C19 | 1.371 (4) |
Cl2—C13 | 1.728 (3) | C14—C15 | 1.391 (4) |
Cl3—C23 | 1.727 (3) | C15—C16 | 1.368 (4) |
Cl4—C27 | 1.727 (3) | C15—H15 | 0.9300 |
N1—C7 | 1.271 (3) | C16—C17 | 1.355 (5) |
N1—O2 | 1.414 (3) | C16—H16 | 0.9300 |
N2—C21 | 1.269 (3) | C17—C18 | 1.361 (5) |
N2—O3 | 1.415 (3) | C17—H17 | 0.9300 |
O1—C1 | 1.191 (3) | C18—C19 | 1.402 (4) |
C1—C5 | 1.531 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.538 (3) | C19—H19 | 0.9300 |
O2—C2 | 1.461 (3) | C20—C28 | 1.508 (3) |
O3—C5 | 1.465 (3) | C20—C21 | 1.509 (3) |
C2—C3 | 1.521 (3) | C20—H20 | 0.9800 |
C2—C6 | 1.538 (3) | C21—C22 | 1.481 (3) |
C3—C4 | 1.537 (3) | C22—C27 | 1.392 (4) |
C3—H3A | 0.9700 | C22—C23 | 1.397 (4) |
C3—H3B | 0.9700 | C23—C24 | 1.383 (4) |
C4—C5 | 1.516 (3) | C24—C25 | 1.371 (5) |
C4—H4A | 0.9700 | C24—H24 | 0.9300 |
C4—H4B | 0.9700 | C25—C26 | 1.367 (5) |
C5—C20 | 1.528 (3) | C25—H25 | 0.9300 |
C6—C14 | 1.513 (3) | C26—C27 | 1.378 (4) |
C6—C7 | 1.518 (3) | C26—H26 | 0.9300 |
C6—H6 | 0.9800 | C28—C33 | 1.368 (4) |
C7—C8 | 1.489 (3) | C28—C29 | 1.383 (4) |
C8—C13 | 1.393 (4) | C29—C30 | 1.373 (4) |
C8—C9 | 1.396 (4) | C29—H29 | 0.9300 |
C9—C10 | 1.386 (4) | C30—C31 | 1.353 (5) |
C10—C11 | 1.370 (4) | C30—H30 | 0.9300 |
C10—H10 | 0.9300 | C31—C32 | 1.377 (5) |
C11—C12 | 1.373 (4) | C31—H31 | 0.9300 |
C11—H11 | 0.9300 | C32—C33 | 1.396 (4) |
C12—C13 | 1.387 (4) | C32—H32 | 0.9300 |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C7—N1—O2 | 109.29 (19) | C16—C15—C14 | 120.7 (3) |
C21—N2—O3 | 108.9 (2) | C16—C15—H15 | 119.6 |
O1—C1—C5 | 125.3 (2) | C14—C15—H15 | 119.6 |
O1—C1—C2 | 125.5 (2) | C17—C16—C15 | 120.4 (3) |
C5—C1—C2 | 108.9 (2) | C17—C16—H16 | 119.8 |
N1—O2—C2 | 108.80 (17) | C15—C16—H16 | 119.8 |
N2—O3—C5 | 109.59 (17) | C16—C17—C18 | 120.3 (3) |
O2—C2—C3 | 107.85 (19) | C16—C17—H17 | 119.8 |
O2—C2—C1 | 105.5 (2) | C18—C17—H17 | 119.8 |
C3—C2—C1 | 103.76 (19) | C17—C18—C19 | 120.1 (3) |
O2—C2—C6 | 104.48 (18) | C17—C18—H18 | 120.0 |
C3—C2—C6 | 121.2 (2) | C19—C18—H18 | 120.0 |
C1—C2—C6 | 113.1 (2) | C14—C19—C18 | 119.8 (3) |
C2—C3—C4 | 104.39 (19) | C14—C19—H19 | 120.1 |
C2—C3—H3A | 110.9 | C18—C19—H19 | 120.1 |
C4—C3—H3A | 110.9 | C28—C20—C21 | 116.5 (2) |
C2—C3—H3B | 110.9 | C28—C20—C5 | 118.17 (19) |
C4—C3—H3B | 110.9 | C21—C20—C5 | 100.35 (18) |
H3A—C3—H3B | 108.9 | C28—C20—H20 | 107.0 |
C5—C4—C3 | 103.50 (18) | C21—C20—H20 | 107.0 |
C5—C4—H4A | 111.1 | C5—C20—H20 | 107.0 |
C3—C4—H4A | 111.1 | N2—C21—C22 | 119.7 (2) |
C5—C4—H4B | 111.1 | N2—C21—C20 | 114.6 (2) |
C3—C4—H4B | 111.1 | C22—C21—C20 | 125.7 (2) |
H4A—C4—H4B | 109.0 | C27—C22—C23 | 116.1 (2) |
O3—C5—C4 | 107.7 (2) | C27—C22—C21 | 122.6 (2) |
O3—C5—C20 | 103.83 (17) | C23—C22—C21 | 121.3 (2) |
C4—C5—C20 | 122.33 (19) | C24—C23—C22 | 122.3 (3) |
O3—C5—C1 | 105.45 (19) | C24—C23—Cl3 | 118.8 (2) |
C4—C5—C1 | 102.61 (19) | C22—C23—Cl3 | 118.9 (2) |
C20—C5—C1 | 113.8 (2) | C25—C24—C23 | 119.0 (3) |
C14—C6—C7 | 112.96 (18) | C25—C24—H24 | 120.5 |
C14—C6—C2 | 115.10 (19) | C23—C24—H24 | 120.5 |
C7—C6—C2 | 99.03 (18) | C26—C25—C24 | 120.8 (3) |
C14—C6—H6 | 109.8 | C26—C25—H25 | 119.6 |
C7—C6—H6 | 109.8 | C24—C25—H25 | 119.6 |
C2—C6—H6 | 109.8 | C25—C26—C27 | 119.6 (3) |
N1—C7—C8 | 118.5 (2) | C25—C26—H26 | 120.2 |
N1—C7—C6 | 114.6 (2) | C27—C26—H26 | 120.2 |
C8—C7—C6 | 126.8 (2) | C26—C27—C22 | 122.1 (3) |
C13—C8—C9 | 116.4 (2) | C26—C27—Cl4 | 117.8 (2) |
C13—C8—C7 | 123.5 (2) | C22—C27—Cl4 | 120.1 (2) |
C9—C8—C7 | 120.1 (2) | C33—C28—C29 | 118.8 (3) |
C10—C9—C8 | 122.2 (3) | C33—C28—C20 | 122.3 (2) |
C10—C9—Cl1 | 117.9 (2) | C29—C28—C20 | 118.9 (2) |
C8—C9—Cl1 | 119.80 (19) | C30—C29—C28 | 121.3 (3) |
C11—C10—C9 | 119.4 (3) | C30—C29—H29 | 119.3 |
C11—C10—H10 | 120.3 | C28—C29—H29 | 119.3 |
C9—C10—H10 | 120.3 | C31—C30—C29 | 119.6 (4) |
C10—C11—C12 | 120.4 (3) | C31—C30—H30 | 120.2 |
C10—C11—H11 | 119.8 | C29—C30—H30 | 120.2 |
C12—C11—H11 | 119.8 | C30—C31—C32 | 120.7 (3) |
C11—C12—C13 | 119.8 (3) | C30—C31—H31 | 119.7 |
C11—C12—H12 | 120.1 | C32—C31—H31 | 119.7 |
C13—C12—H12 | 120.1 | C31—C32—C33 | 119.5 (4) |
C12—C13—C8 | 121.8 (3) | C31—C32—H32 | 120.2 |
C12—C13—Cl2 | 117.3 (2) | C33—C32—H32 | 120.2 |
C8—C13—Cl2 | 120.9 (2) | C28—C33—C32 | 120.1 (3) |
C19—C14—C15 | 118.7 (2) | C28—C33—H33 | 120.0 |
C19—C14—C6 | 121.1 (2) | C32—C33—H33 | 120.0 |
C15—C14—C6 | 120.2 (2) | ||
C7—N1—O2—C2 | 10.9 (3) | C7—C8—C13—Cl2 | −3.2 (3) |
C21—N2—O3—C5 | −8.2 (3) | C7—C6—C14—C19 | 131.7 (2) |
N1—O2—C2—C3 | −148.86 (18) | C2—C6—C14—C19 | −115.6 (3) |
N1—O2—C2—C1 | 100.7 (2) | C7—C6—C14—C15 | −51.1 (3) |
N1—O2—C2—C6 | −18.7 (2) | C2—C6—C14—C15 | 61.7 (3) |
O1—C1—C2—O2 | −64.3 (4) | C19—C14—C15—C16 | −0.8 (4) |
C5—C1—C2—O2 | 108.9 (2) | C6—C14—C15—C16 | −178.2 (3) |
O1—C1—C2—C3 | −177.6 (3) | C14—C15—C16—C17 | 0.5 (5) |
C5—C1—C2—C3 | −4.4 (3) | C15—C16—C17—C18 | 0.3 (5) |
O1—C1—C2—C6 | 49.2 (4) | C16—C17—C18—C19 | −0.7 (5) |
C5—C1—C2—C6 | −137.6 (2) | C15—C14—C19—C18 | 0.4 (4) |
O2—C2—C3—C4 | −84.0 (2) | C6—C14—C19—C18 | 177.7 (2) |
C1—C2—C3—C4 | 27.6 (3) | C17—C18—C19—C14 | 0.3 (5) |
C6—C2—C3—C4 | 155.9 (2) | O3—C5—C20—C28 | −143.3 (2) |
C2—C3—C4—C5 | −41.4 (2) | C4—C5—C20—C28 | −21.5 (3) |
N2—O3—C5—C4 | −115.7 (2) | C1—C5—C20—C28 | 102.6 (3) |
N2—O3—C5—C20 | 15.4 (2) | O3—C5—C20—C21 | −15.5 (2) |
N2—O3—C5—C1 | 135.3 (2) | C4—C5—C20—C21 | 106.3 (2) |
C3—C4—C5—O3 | −73.6 (2) | C1—C5—C20—C21 | −129.6 (2) |
C3—C4—C5—C20 | 166.4 (2) | O3—N2—C21—C22 | 179.2 (2) |
C3—C4—C5—C1 | 37.3 (2) | O3—N2—C21—C20 | −3.1 (3) |
O1—C1—C5—O3 | −94.7 (3) | C28—C20—C21—N2 | 141.1 (2) |
C2—C1—C5—O3 | 92.1 (2) | C5—C20—C21—N2 | 12.2 (3) |
O1—C1—C5—C4 | 152.6 (3) | C28—C20—C21—C22 | −41.4 (3) |
C2—C1—C5—C4 | −20.6 (3) | C5—C20—C21—C22 | −170.2 (2) |
O1—C1—C5—C20 | 18.4 (4) | N2—C21—C22—C27 | −67.1 (3) |
C2—C1—C5—C20 | −154.8 (2) | C20—C21—C22—C27 | 115.5 (3) |
O2—C2—C6—C14 | −102.7 (2) | N2—C21—C22—C23 | 112.5 (3) |
C3—C2—C6—C14 | 19.1 (3) | C20—C21—C22—C23 | −64.9 (3) |
C1—C2—C6—C14 | 143.1 (2) | C27—C22—C23—C24 | 0.8 (4) |
O2—C2—C6—C7 | 18.0 (2) | C21—C22—C23—C24 | −178.8 (3) |
C3—C2—C6—C7 | 139.8 (2) | C27—C22—C23—Cl3 | 179.3 (2) |
C1—C2—C6—C7 | −96.2 (2) | C21—C22—C23—Cl3 | −0.3 (4) |
O2—N1—C7—C8 | −178.65 (19) | C22—C23—C24—C25 | −1.2 (5) |
O2—N1—C7—C6 | 2.2 (3) | Cl3—C23—C24—C25 | −179.7 (3) |
C14—C6—C7—N1 | 109.1 (2) | C23—C24—C25—C26 | 0.4 (5) |
C2—C6—C7—N1 | −13.2 (3) | C24—C25—C26—C27 | 0.6 (5) |
C14—C6—C7—C8 | −70.0 (3) | C25—C26—C27—C22 | −0.9 (5) |
C2—C6—C7—C8 | 167.8 (2) | C25—C26—C27—Cl4 | 178.8 (3) |
N1—C7—C8—C13 | −66.9 (3) | C23—C22—C27—C26 | 0.2 (4) |
C6—C7—C8—C13 | 112.1 (3) | C21—C22—C27—C26 | 179.9 (3) |
N1—C7—C8—C9 | 111.1 (3) | C23—C22—C27—Cl4 | −179.5 (2) |
C6—C7—C8—C9 | −69.9 (3) | C21—C22—C27—Cl4 | 0.1 (4) |
C13—C8—C9—C10 | −1.2 (4) | C21—C20—C28—C33 | −46.0 (3) |
C7—C8—C9—C10 | −179.4 (2) | C5—C20—C28—C33 | 73.6 (3) |
C13—C8—C9—Cl1 | 176.56 (18) | C21—C20—C28—C29 | 133.5 (2) |
C7—C8—C9—Cl1 | −1.6 (3) | C5—C20—C28—C29 | −106.8 (3) |
C8—C9—C10—C11 | 1.9 (4) | C33—C28—C29—C30 | 0.5 (4) |
Cl1—C9—C10—C11 | −175.9 (2) | C20—C28—C29—C30 | −179.0 (3) |
C9—C10—C11—C12 | −0.8 (4) | C28—C29—C30—C31 | 1.1 (5) |
C10—C11—C12—C13 | −0.8 (4) | C29—C30—C31—C32 | −2.0 (6) |
C11—C12—C13—C8 | 1.5 (4) | C30—C31—C32—C33 | 1.4 (5) |
C11—C12—C13—Cl2 | −177.8 (2) | C29—C28—C33—C32 | −1.1 (4) |
C9—C8—C13—C12 | −0.5 (4) | C20—C28—C33—C32 | 178.4 (3) |
C7—C8—C13—C12 | 177.6 (2) | C31—C32—C33—C28 | 0.2 (5) |
C9—C8—C13—Cl2 | 178.75 (19) |