Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024632/hg6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024632/hg6003Isup2.hkl |
CCDC reference: 227035
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.
C35H26Cl4N2O3 | Z = 2 |
Mr = 664.38 | F(000) = 684 |
Triclinic, P1 | Dx = 1.410 Mg m−3 |
Hall symbol: -P 1 | Melting point: 517 K |
a = 9.095 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.010 (4) Å | Cell parameters from 954 reflections |
c = 14.078 (4) Å | θ = 3.5–26.1° |
α = 79.674 (5)° | µ = 0.42 mm−1 |
β = 86.207 (5)° | T = 293 K |
γ = 72.793 (4)° | Block, colorless |
V = 1565.3 (8) Å3 | 0.28 × 0.22 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 6351 independent reflections |
Radiation source: fine-focus sealed tube | 3949 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→10 |
Tmin = 0.834, Tmax = 0.960 | k = −16→16 |
9083 measured reflections | l = −17→8 |
Refinement on F2 | 0 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) = 0.135 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.40 e Å−3 |
6351 reflections | Δρmin = −0.40 e Å−3 |
397 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 | 0.42632 (10) | 0.59153 (6) | 0.13737 (6) | 0.0607 (2) | |
Cl2 | 0.64533 (10) | 0.14932 (6) | 0.15517 (7) | 0.0632 (3) | |
Cl3 | 0.17323 (12) | 0.84830 (7) | 0.10099 (8) | 0.0810 (3) | |
Cl4 | −0.11427 (15) | 0.88297 (7) | 0.45068 (6) | 0.0849 (4) | |
N1 | 0.3125 (3) | 0.31528 (17) | 0.15098 (16) | 0.0417 (6) | |
N2 | 0.0929 (3) | 0.68577 (17) | 0.36639 (17) | 0.0441 (6) | |
O1 | 0.0394 (2) | 0.51545 (15) | 0.13853 (13) | 0.0449 (5) | |
O2 | 0.1793 (2) | 0.31318 (14) | 0.20849 (14) | 0.0430 (5) | |
O3 | 0.0686 (2) | 0.58362 (13) | 0.36510 (12) | 0.0416 (5) | |
C1 | 0.0587 (3) | 0.4997 (2) | 0.22420 (19) | 0.0325 (6) | |
C2 | 0.1601 (3) | 0.3887 (2) | 0.27619 (19) | 0.0367 (6) | |
C3 | 0.0841 (3) | 0.3445 (2) | 0.3675 (2) | 0.0427 (7) | |
H3A | 0.1054 | 0.3765 | 0.4203 | 0.051* | |
H3B | 0.1317 | 0.2663 | 0.3827 | 0.051* | |
C4 | −0.0897 (3) | 0.3656 (2) | 0.3627 (2) | 0.0458 (7) | |
H4A | −0.1191 | 0.3079 | 0.4061 | 0.055* | |
H4B | −0.1160 | 0.3628 | 0.2977 | 0.055* | |
C5 | −0.1818 (3) | 0.4757 (2) | 0.3895 (2) | 0.0461 (7) | |
H5A | −0.2878 | 0.4750 | 0.4014 | 0.055* | |
H5B | −0.1423 | 0.4825 | 0.4497 | 0.055* | |
C6 | −0.1812 (3) | 0.5769 (2) | 0.3161 (2) | 0.0421 (7) | |
H6A | −0.2377 | 0.6405 | 0.3439 | 0.051* | |
H6B | −0.2374 | 0.5765 | 0.2600 | 0.051* | |
C7 | −0.0241 (3) | 0.59084 (19) | 0.28147 (18) | 0.0326 (6) | |
C8 | 0.3254 (3) | 0.3963 (2) | 0.28570 (19) | 0.0359 (6) | |
H8 | 0.3225 | 0.4722 | 0.2854 | 0.043* | |
C9 | 0.3921 (3) | 0.36186 (19) | 0.19081 (18) | 0.0361 (6) | |
C10 | 0.5422 (3) | 0.3712 (2) | 0.14744 (19) | 0.0378 (6) | |
C11 | 0.5705 (3) | 0.4728 (2) | 0.12245 (19) | 0.0425 (7) | |
C12 | 0.7092 (4) | 0.4845 (3) | 0.0827 (2) | 0.0507 (8) | |
H12 | 0.7233 | 0.5534 | 0.0657 | 0.061* | |
C13 | 0.8255 (4) | 0.3931 (3) | 0.0688 (2) | 0.0558 (8) | |
H13 | 0.9199 | 0.3999 | 0.0437 | 0.067* | |
C14 | 0.8031 (4) | 0.2917 (3) | 0.0916 (2) | 0.0518 (8) | |
H14 | 0.8820 | 0.2302 | 0.0813 | 0.062* | |
C15 | 0.6635 (3) | 0.2806 (2) | 0.1299 (2) | 0.0434 (7) | |
C16 | 0.4175 (3) | 0.3229 (2) | 0.3711 (2) | 0.0441 (7) | |
C17 | 0.4635 (4) | 0.2099 (3) | 0.3781 (3) | 0.0656 (9) | |
H17 | 0.4364 | 0.1775 | 0.3308 | 0.079* | |
C18 | 0.5507 (5) | 0.1458 (4) | 0.4567 (3) | 0.0913 (14) | |
H18 | 0.5837 | 0.0703 | 0.4613 | 0.110* | |
C19 | 0.5884 (5) | 0.1939 (5) | 0.5276 (3) | 0.0986 (16) | |
H19 | 0.6454 | 0.1507 | 0.5803 | 0.118* | |
C20 | 0.5427 (5) | 0.3032 (4) | 0.5207 (3) | 0.0896 (13) | |
H20 | 0.5697 | 0.3349 | 0.5685 | 0.107* | |
C21 | 0.4563 (4) | 0.3691 (3) | 0.4437 (2) | 0.0598 (9) | |
H21 | 0.4241 | 0.4444 | 0.4405 | 0.072* | |
C22 | −0.0316 (3) | 0.70456 (19) | 0.22034 (19) | 0.0354 (6) | |
H22 | 0.0412 | 0.6927 | 0.1661 | 0.042* | |
C23 | 0.0366 (3) | 0.7520 (2) | 0.2906 (2) | 0.0383 (6) | |
C24 | 0.0399 (3) | 0.8676 (2) | 0.2784 (2) | 0.0446 (7) | |
C25 | 0.1017 (4) | 0.9181 (2) | 0.1963 (2) | 0.0534 (8) | |
C26 | 0.1108 (4) | 1.0239 (3) | 0.1866 (3) | 0.0710 (11) | |
H26 | 0.1555 | 1.0545 | 0.1317 | 0.085* | |
C27 | 0.0526 (5) | 1.0833 (3) | 0.2594 (3) | 0.0814 (13) | |
H27 | 0.0591 | 1.1542 | 0.2538 | 0.098* | |
C28 | −0.0143 (5) | 1.0392 (3) | 0.3398 (3) | 0.0747 (12) | |
H28 | −0.0555 | 1.0802 | 0.3881 | 0.090* | |
C29 | −0.0200 (4) | 0.9327 (2) | 0.3486 (2) | 0.0596 (9) | |
C30 | −0.1860 (3) | 0.7744 (2) | 0.17947 (19) | 0.0384 (6) | |
C31 | −0.2190 (4) | 0.7715 (2) | 0.0853 (2) | 0.0496 (7) | |
H31 | −0.1457 | 0.7282 | 0.0486 | 0.060* | |
C32 | −0.3594 (5) | 0.8320 (3) | 0.0455 (3) | 0.0666 (10) | |
H32 | −0.3807 | 0.8288 | −0.0175 | 0.080* | |
C33 | −0.4668 (4) | 0.8964 (3) | 0.0985 (3) | 0.0688 (10) | |
H33 | −0.5611 | 0.9374 | 0.0715 | 0.083* | |
C34 | −0.4366 (4) | 0.9010 (3) | 0.1915 (3) | 0.0652 (10) | |
H34 | −0.5101 | 0.9454 | 0.2273 | 0.078* | |
C35 | −0.2958 (4) | 0.8394 (2) | 0.2326 (2) | 0.0511 (8) | |
H35 | −0.2760 | 0.8421 | 0.2959 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0640 (6) | 0.0354 (4) | 0.0789 (6) | −0.0141 (4) | 0.0066 (4) | −0.0029 (4) |
Cl2 | 0.0600 (5) | 0.0403 (4) | 0.0864 (6) | −0.0084 (4) | 0.0064 (4) | −0.0165 (4) |
Cl3 | 0.0831 (7) | 0.0607 (5) | 0.1042 (8) | −0.0350 (5) | 0.0403 (6) | −0.0177 (5) |
Cl4 | 0.1464 (11) | 0.0516 (5) | 0.0501 (5) | −0.0150 (6) | −0.0037 (6) | −0.0136 (4) |
N1 | 0.0411 (14) | 0.0362 (12) | 0.0497 (14) | −0.0124 (11) | 0.0050 (11) | −0.0121 (10) |
N2 | 0.0501 (15) | 0.0310 (12) | 0.0530 (15) | −0.0119 (11) | −0.0136 (12) | −0.0066 (11) |
O1 | 0.0545 (13) | 0.0411 (11) | 0.0393 (11) | −0.0132 (9) | −0.0025 (9) | −0.0078 (8) |
O2 | 0.0421 (12) | 0.0355 (10) | 0.0582 (12) | −0.0178 (9) | 0.0056 (9) | −0.0163 (9) |
O3 | 0.0551 (13) | 0.0299 (9) | 0.0410 (11) | −0.0136 (9) | −0.0145 (9) | −0.0018 (8) |
C1 | 0.0310 (14) | 0.0326 (13) | 0.0381 (16) | −0.0162 (11) | 0.0008 (11) | −0.0058 (11) |
C2 | 0.0396 (16) | 0.0286 (13) | 0.0442 (16) | −0.0133 (11) | 0.0024 (12) | −0.0069 (11) |
C3 | 0.0454 (17) | 0.0323 (14) | 0.0486 (17) | −0.0131 (12) | 0.0035 (13) | −0.0008 (12) |
C4 | 0.0449 (18) | 0.0410 (15) | 0.0537 (18) | −0.0213 (13) | 0.0058 (14) | −0.0006 (13) |
C5 | 0.0408 (17) | 0.0450 (16) | 0.0515 (18) | −0.0163 (13) | 0.0108 (14) | −0.0033 (13) |
C6 | 0.0389 (16) | 0.0390 (15) | 0.0474 (17) | −0.0103 (13) | 0.0037 (13) | −0.0076 (12) |
C7 | 0.0359 (15) | 0.0269 (12) | 0.0361 (14) | −0.0119 (11) | −0.0035 (11) | −0.0026 (10) |
C8 | 0.0357 (15) | 0.0284 (12) | 0.0447 (16) | −0.0104 (11) | −0.0006 (12) | −0.0068 (11) |
C9 | 0.0385 (16) | 0.0275 (13) | 0.0407 (15) | −0.0092 (12) | 0.0017 (12) | −0.0030 (11) |
C10 | 0.0391 (16) | 0.0379 (14) | 0.0377 (15) | −0.0131 (12) | −0.0030 (12) | −0.0054 (11) |
C11 | 0.0482 (18) | 0.0421 (15) | 0.0389 (15) | −0.0161 (13) | −0.0019 (13) | −0.0059 (12) |
C12 | 0.058 (2) | 0.062 (2) | 0.0430 (17) | −0.0348 (17) | 0.0033 (15) | −0.0064 (14) |
C13 | 0.046 (2) | 0.077 (2) | 0.0511 (19) | −0.0276 (18) | 0.0089 (15) | −0.0170 (17) |
C14 | 0.0420 (18) | 0.061 (2) | 0.0491 (18) | −0.0073 (15) | 0.0038 (14) | −0.0148 (15) |
C15 | 0.0422 (17) | 0.0447 (16) | 0.0434 (16) | −0.0112 (13) | −0.0025 (13) | −0.0092 (13) |
C16 | 0.0327 (16) | 0.0519 (17) | 0.0447 (17) | −0.0114 (13) | 0.0026 (12) | −0.0023 (13) |
C17 | 0.072 (2) | 0.0482 (19) | 0.064 (2) | −0.0029 (17) | −0.0062 (18) | 0.0010 (16) |
C18 | 0.078 (3) | 0.070 (3) | 0.092 (3) | 0.011 (2) | −0.005 (3) | 0.021 (2) |
C19 | 0.069 (3) | 0.128 (4) | 0.072 (3) | −0.013 (3) | −0.019 (2) | 0.031 (3) |
C20 | 0.077 (3) | 0.129 (4) | 0.065 (3) | −0.038 (3) | −0.023 (2) | 0.001 (3) |
C21 | 0.053 (2) | 0.076 (2) | 0.053 (2) | −0.0232 (18) | −0.0057 (16) | −0.0092 (17) |
C22 | 0.0389 (15) | 0.0278 (12) | 0.0404 (15) | −0.0113 (11) | −0.0040 (12) | −0.0041 (11) |
C23 | 0.0367 (16) | 0.0309 (13) | 0.0494 (17) | −0.0113 (12) | −0.0089 (13) | −0.0065 (12) |
C24 | 0.0475 (18) | 0.0304 (14) | 0.0589 (19) | −0.0139 (13) | −0.0223 (14) | −0.0031 (13) |
C25 | 0.0440 (18) | 0.0394 (16) | 0.080 (2) | −0.0171 (14) | −0.0062 (16) | −0.0080 (15) |
C26 | 0.062 (2) | 0.0403 (17) | 0.112 (3) | −0.0232 (17) | −0.008 (2) | 0.002 (2) |
C27 | 0.097 (3) | 0.0369 (18) | 0.119 (4) | −0.029 (2) | −0.035 (3) | −0.007 (2) |
C28 | 0.111 (3) | 0.0376 (18) | 0.080 (3) | −0.017 (2) | −0.035 (2) | −0.0178 (18) |
C29 | 0.084 (3) | 0.0385 (16) | 0.057 (2) | −0.0146 (16) | −0.0298 (18) | −0.0060 (14) |
C30 | 0.0394 (16) | 0.0287 (13) | 0.0480 (16) | −0.0129 (12) | −0.0100 (13) | 0.0002 (12) |
C31 | 0.057 (2) | 0.0401 (16) | 0.0516 (18) | −0.0154 (14) | −0.0151 (15) | 0.0011 (13) |
C32 | 0.071 (3) | 0.061 (2) | 0.066 (2) | −0.022 (2) | −0.032 (2) | 0.0083 (18) |
C33 | 0.050 (2) | 0.060 (2) | 0.090 (3) | −0.0176 (18) | −0.034 (2) | 0.019 (2) |
C34 | 0.043 (2) | 0.0488 (19) | 0.093 (3) | −0.0046 (15) | 0.0013 (19) | 0.0002 (18) |
C35 | 0.0495 (19) | 0.0431 (16) | 0.0570 (19) | −0.0092 (14) | −0.0060 (15) | −0.0044 (14) |
Cl1—C11 | 1.741 (3) | C13—H13 | 0.9300 |
Cl2—C15 | 1.735 (3) | C14—C15 | 1.383 (4) |
Cl3—C25 | 1.738 (3) | C14—H14 | 0.9300 |
Cl4—C29 | 1.747 (4) | C16—C21 | 1.387 (4) |
N1—C9 | 1.281 (3) | C16—C17 | 1.391 (4) |
N1—O2 | 1.417 (3) | C17—C18 | 1.393 (5) |
N2—C23 | 1.274 (3) | C17—H17 | 0.9300 |
N2—O3 | 1.413 (3) | C18—C19 | 1.379 (7) |
O1—C1 | 1.202 (3) | C18—H18 | 0.9300 |
O2—C2 | 1.455 (3) | C19—C20 | 1.345 (6) |
O3—C7 | 1.467 (3) | C19—H19 | 0.9300 |
C1—C7 | 1.535 (3) | C20—C21 | 1.382 (5) |
C1—C2 | 1.548 (4) | C20—H20 | 0.9300 |
C2—C3 | 1.521 (4) | C21—H21 | 0.9300 |
C2—C8 | 1.552 (4) | C22—C23 | 1.507 (4) |
C3—C4 | 1.526 (4) | C22—C30 | 1.515 (4) |
C3—H3A | 0.9700 | C22—H22 | 0.9800 |
C3—H3B | 0.9700 | C23—C24 | 1.491 (3) |
C4—C5 | 1.529 (4) | C24—C25 | 1.394 (4) |
C4—H4A | 0.9700 | C24—C29 | 1.396 (4) |
C4—H4B | 0.9700 | C25—C26 | 1.385 (4) |
C5—C6 | 1.522 (4) | C26—C27 | 1.377 (5) |
C5—H5A | 0.9700 | C26—H26 | 0.9300 |
C5—H5B | 0.9700 | C27—C28 | 1.365 (5) |
C6—C7 | 1.530 (4) | C27—H27 | 0.9300 |
C6—H6A | 0.9700 | C28—C29 | 1.384 (4) |
C6—H6B | 0.9700 | C28—H28 | 0.9300 |
C7—C22 | 1.558 (3) | C30—C35 | 1.378 (4) |
C8—C9 | 1.516 (4) | C30—C31 | 1.388 (4) |
C8—C16 | 1.519 (4) | C31—C32 | 1.381 (4) |
C8—H8 | 0.9800 | C31—H31 | 0.9300 |
C9—C10 | 1.487 (4) | C32—C33 | 1.362 (5) |
C10—C11 | 1.400 (4) | C32—H32 | 0.9300 |
C10—C15 | 1.402 (4) | C33—C34 | 1.371 (5) |
C11—C12 | 1.384 (4) | C33—H33 | 0.9300 |
C12—C13 | 1.372 (4) | C34—C35 | 1.393 (4) |
C12—H12 | 0.9300 | C34—H34 | 0.9300 |
C13—C14 | 1.373 (4) | C35—H35 | 0.9300 |
C9—N1—O2 | 108.8 (2) | C14—C15—C10 | 121.6 (3) |
C23—N2—O3 | 109.5 (2) | C14—C15—Cl2 | 116.9 (2) |
N1—O2—C2 | 108.61 (18) | C10—C15—Cl2 | 121.5 (2) |
N2—O3—C7 | 109.92 (17) | C21—C16—C17 | 119.3 (3) |
O1—C1—C7 | 118.5 (2) | C21—C16—C8 | 119.5 (3) |
O1—C1—C2 | 120.8 (2) | C17—C16—C8 | 121.2 (3) |
C7—C1—C2 | 120.7 (2) | C16—C17—C18 | 119.3 (4) |
O2—C2—C3 | 107.9 (2) | C16—C17—H17 | 120.4 |
O2—C2—C1 | 105.7 (2) | C18—C17—H17 | 120.4 |
C3—C2—C1 | 112.8 (2) | C19—C18—C17 | 120.3 (4) |
O2—C2—C8 | 103.5 (2) | C19—C18—H18 | 119.8 |
C3—C2—C8 | 116.9 (2) | C17—C18—H18 | 119.8 |
C1—C2—C8 | 109.1 (2) | C20—C19—C18 | 120.1 (4) |
C2—C3—C4 | 115.5 (2) | C20—C19—H19 | 119.9 |
C2—C3—H3A | 108.4 | C18—C19—H19 | 119.9 |
C4—C3—H3A | 108.4 | C19—C20—C21 | 121.0 (4) |
C2—C3—H3B | 108.4 | C19—C20—H20 | 119.5 |
C4—C3—H3B | 108.4 | C21—C20—H20 | 119.5 |
H3A—C3—H3B | 107.5 | C20—C21—C16 | 120.0 (4) |
C3—C4—C5 | 113.2 (2) | C20—C21—H21 | 120.0 |
C3—C4—H4A | 108.9 | C16—C21—H21 | 120.0 |
C5—C4—H4A | 108.9 | C23—C22—C30 | 115.6 (2) |
C3—C4—H4B | 108.9 | C23—C22—C7 | 100.0 (2) |
C5—C4—H4B | 108.9 | C30—C22—C7 | 117.6 (2) |
H4A—C4—H4B | 107.8 | C23—C22—H22 | 107.7 |
C6—C5—C4 | 116.8 (2) | C30—C22—H22 | 107.7 |
C6—C5—H5A | 108.1 | C7—C22—H22 | 107.7 |
C4—C5—H5A | 108.1 | N2—C23—C24 | 119.5 (2) |
C6—C5—H5B | 108.1 | N2—C23—C22 | 115.2 (2) |
C4—C5—H5B | 108.1 | C24—C23—C22 | 125.3 (2) |
H5A—C5—H5B | 107.3 | C25—C24—C29 | 115.5 (3) |
C5—C6—C7 | 117.1 (2) | C25—C24—C23 | 122.6 (3) |
C5—C6—H6A | 108.0 | C29—C24—C23 | 121.9 (3) |
C7—C6—H6A | 108.0 | C26—C25—C24 | 122.6 (3) |
C5—C6—H6B | 108.0 | C26—C25—Cl3 | 117.0 (3) |
C7—C6—H6B | 108.0 | C24—C25—Cl3 | 120.4 (2) |
H6A—C6—H6B | 107.3 | C27—C26—C25 | 119.1 (4) |
O3—C7—C6 | 109.5 (2) | C27—C26—H26 | 120.4 |
O3—C7—C1 | 109.3 (2) | C25—C26—H26 | 120.4 |
C6—C7—C1 | 109.2 (2) | C28—C27—C26 | 120.7 (3) |
O3—C7—C22 | 104.33 (19) | C28—C27—H27 | 119.7 |
C6—C7—C22 | 114.2 (2) | C26—C27—H27 | 119.7 |
C1—C7—C22 | 110.3 (2) | C27—C28—C29 | 119.2 (3) |
C9—C8—C16 | 111.6 (2) | C27—C28—H28 | 120.4 |
C9—C8—C2 | 98.4 (2) | C29—C28—H28 | 120.4 |
C16—C8—C2 | 116.5 (2) | C28—C29—C24 | 122.8 (3) |
C9—C8—H8 | 109.9 | C28—C29—Cl4 | 117.0 (3) |
C16—C8—H8 | 109.9 | C24—C29—Cl4 | 120.1 (2) |
C2—C8—H8 | 109.9 | C35—C30—C31 | 118.8 (3) |
N1—C9—C10 | 120.2 (2) | C35—C30—C22 | 122.6 (3) |
N1—C9—C8 | 114.3 (2) | C31—C30—C22 | 118.6 (3) |
C10—C9—C8 | 125.4 (2) | C32—C31—C30 | 120.8 (3) |
C11—C10—C15 | 115.9 (2) | C32—C31—H31 | 119.6 |
C11—C10—C9 | 121.1 (2) | C30—C31—H31 | 119.6 |
C15—C10—C9 | 122.9 (2) | C33—C32—C31 | 119.9 (3) |
C12—C11—C10 | 122.7 (3) | C33—C32—H32 | 120.0 |
C12—C11—Cl1 | 117.2 (2) | C31—C32—H32 | 120.0 |
C10—C11—Cl1 | 120.1 (2) | C32—C33—C34 | 120.3 (3) |
C13—C12—C11 | 119.1 (3) | C32—C33—H33 | 119.8 |
C13—C12—H12 | 120.4 | C34—C33—H33 | 119.8 |
C11—C12—H12 | 120.4 | C33—C34—C35 | 120.1 (3) |
C12—C13—C14 | 120.3 (3) | C33—C34—H34 | 120.0 |
C12—C13—H13 | 119.8 | C35—C34—H34 | 120.0 |
C14—C13—H13 | 119.8 | C30—C35—C34 | 120.1 (3) |
C13—C14—C15 | 120.3 (3) | C30—C35—H35 | 120.0 |
C13—C14—H14 | 119.9 | C34—C35—H35 | 120.0 |
C15—C14—H14 | 119.9 | ||
C9—N1—O2—C2 | 15.0 (3) | C11—C10—C15—Cl2 | −179.0 (2) |
C23—N2—O3—C7 | −4.7 (3) | C9—C10—C15—Cl2 | 1.7 (4) |
N1—O2—C2—C3 | −148.9 (2) | C9—C8—C16—C21 | 134.6 (3) |
N1—O2—C2—C1 | 90.2 (2) | C2—C8—C16—C21 | −113.5 (3) |
N1—O2—C2—C8 | −24.4 (2) | C9—C8—C16—C17 | −45.6 (4) |
O1—C1—C2—O2 | −15.2 (3) | C2—C8—C16—C17 | 66.3 (3) |
C7—C1—C2—O2 | 162.6 (2) | C21—C16—C17—C18 | −1.5 (5) |
O1—C1—C2—C3 | −132.9 (3) | C8—C16—C17—C18 | 178.6 (3) |
C7—C1—C2—C3 | 44.9 (3) | C16—C17—C18—C19 | 1.2 (6) |
O1—C1—C2—C8 | 95.5 (3) | C17—C18—C19—C20 | −0.8 (7) |
C7—C1—C2—C8 | −86.7 (3) | C18—C19—C20—C21 | 0.8 (7) |
O2—C2—C3—C4 | −79.4 (3) | C19—C20—C21—C16 | −1.1 (6) |
C1—C2—C3—C4 | 36.9 (3) | C17—C16—C21—C20 | 1.5 (5) |
C8—C2—C3—C4 | 164.5 (2) | C8—C16—C21—C20 | −178.7 (3) |
C2—C3—C4—C5 | −87.0 (3) | O3—C7—C22—C23 | −9.8 (2) |
C3—C4—C5—C6 | 72.8 (3) | C6—C7—C22—C23 | 109.7 (2) |
C4—C5—C6—C7 | −54.1 (4) | C1—C7—C22—C23 | −127.0 (2) |
N2—O3—C7—C6 | −113.2 (2) | O3—C7—C22—C30 | −135.8 (2) |
N2—O3—C7—C1 | 127.3 (2) | C6—C7—C22—C30 | −16.2 (3) |
N2—O3—C7—C22 | 9.4 (3) | C1—C7—C22—C30 | 107.0 (3) |
C5—C6—C7—O3 | −53.7 (3) | O3—N2—C23—C24 | 176.4 (2) |
C5—C6—C7—C1 | 65.9 (3) | O3—N2—C23—C22 | −2.6 (3) |
C5—C6—C7—C22 | −170.2 (2) | C30—C22—C23—N2 | 135.4 (3) |
O1—C1—C7—O3 | −150.4 (2) | C7—C22—C23—N2 | 8.1 (3) |
C2—C1—C7—O3 | 31.8 (3) | C30—C22—C23—C24 | −43.6 (4) |
O1—C1—C7—C6 | 89.9 (3) | C7—C22—C23—C24 | −170.9 (3) |
C2—C1—C7—C6 | −87.9 (3) | N2—C23—C24—C25 | 126.7 (3) |
O1—C1—C7—C22 | −36.3 (3) | C22—C23—C24—C25 | −54.3 (4) |
C2—C1—C7—C22 | 145.9 (2) | N2—C23—C24—C29 | −53.7 (4) |
O2—C2—C8—C9 | 23.0 (2) | C22—C23—C24—C29 | 125.3 (3) |
C3—C2—C8—C9 | 141.4 (2) | C29—C24—C25—C26 | 3.2 (5) |
C1—C2—C8—C9 | −89.2 (2) | C23—C24—C25—C26 | −177.2 (3) |
O2—C2—C8—C16 | −96.3 (2) | C29—C24—C25—Cl3 | −177.4 (2) |
C3—C2—C8—C16 | 22.1 (3) | C23—C24—C25—Cl3 | 2.2 (4) |
C1—C2—C8—C16 | 151.5 (2) | C24—C25—C26—C27 | −2.0 (5) |
O2—N1—C9—C10 | 177.5 (2) | Cl3—C25—C26—C27 | 178.7 (3) |
O2—N1—C9—C8 | 1.8 (3) | C25—C26—C27—C28 | −0.5 (6) |
C16—C8—C9—N1 | 106.8 (3) | C26—C27—C28—C29 | 1.5 (6) |
C2—C8—C9—N1 | −16.1 (3) | C27—C28—C29—C24 | −0.1 (6) |
C16—C8—C9—C10 | −68.7 (3) | C27—C28—C29—Cl4 | −177.4 (3) |
C2—C8—C9—C10 | 168.4 (2) | C25—C24—C29—C28 | −2.2 (5) |
N1—C9—C10—C11 | 124.0 (3) | C23—C24—C29—C28 | 178.2 (3) |
C8—C9—C10—C11 | −60.8 (4) | C25—C24—C29—Cl4 | 175.0 (2) |
N1—C9—C10—C15 | −56.7 (4) | C23—C24—C29—Cl4 | −4.6 (4) |
C8—C9—C10—C15 | 118.5 (3) | C23—C22—C30—C35 | −34.8 (4) |
C15—C10—C11—C12 | 0.1 (4) | C7—C22—C30—C35 | 83.1 (3) |
C9—C10—C11—C12 | 179.4 (3) | C23—C22—C30—C31 | 146.3 (2) |
C15—C10—C11—Cl1 | 178.0 (2) | C7—C22—C30—C31 | −95.8 (3) |
C9—C10—C11—Cl1 | −2.7 (4) | C35—C30—C31—C32 | −0.3 (4) |
C10—C11—C12—C13 | −1.4 (5) | C22—C30—C31—C32 | 178.7 (3) |
Cl1—C11—C12—C13 | −179.3 (2) | C30—C31—C32—C33 | 0.6 (5) |
C11—C12—C13—C14 | 1.6 (5) | C31—C32—C33—C34 | −0.3 (5) |
C12—C13—C14—C15 | −0.7 (5) | C32—C33—C34—C35 | −0.3 (5) |
C13—C14—C15—C10 | −0.6 (5) | C31—C30—C35—C34 | −0.4 (4) |
C13—C14—C15—Cl2 | 179.2 (2) | C22—C30—C35—C34 | −179.2 (3) |
C11—C10—C15—C14 | 0.9 (4) | C33—C34—C35—C30 | 0.6 (5) |
C9—C10—C15—C14 | −178.4 (3) |