Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037974/at2114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037974/at2114Isup2.hkl |
CCDC reference: 623975
Key indicators
- Single-crystal X-ray study
- T = 295 K
- R factor = 0.057
- wR factor = 0.134
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
C18H15Cl2N3O | F(000) = 2976 |
Mr = 360.23 | Dx = 1.392 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6442 reflections |
a = 18.9602 (8) Å | θ = 2.2–22.9° |
b = 7.1044 (3) Å | µ = 0.39 mm−1 |
c = 51.387 (2) Å | T = 295 K |
β = 96.529 (1)° | Prism, yellow |
V = 6877.0 (5) Å3 | 0.35 × 0.08 × 0.07 mm |
Z = 16 |
Bruker APEX area-detector diffractometer | 7114 independent reflections |
Radiation source: fine-focus sealed tube | 5532 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 26.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
Tmin = 0.956, Tmax = 0.973 | k = −8→8 |
35938 measured reflections | l = −64→64 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0478P)2 + 7.688P] where P = (Fo2 + 2Fc2)/3 |
7114 reflections | (Δ/σ)max = 0.001 |
437 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
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 | 0.55293 (4) | 0.26083 (10) | 0.116299 (17) | 0.0701 (3) | |
Cl2 | 0.66956 (4) | 0.23148 (11) | 0.077987 (15) | 0.0651 (2) | |
O1 | 0.43058 (11) | 0.5140 (3) | 0.17670 (4) | 0.0598 (5) | |
N1 | 0.41610 (11) | 0.7618 (3) | 0.20490 (4) | 0.0452 (5) | |
N2 | 0.45366 (12) | 0.9274 (3) | 0.21218 (4) | 0.0457 (5) | |
N3 | 0.54767 (11) | 0.7834 (3) | 0.15919 (4) | 0.0461 (5) | |
C1 | 0.32109 (15) | 0.5575 (4) | 0.21376 (6) | 0.0534 (7) | |
H1 | 0.3055 | 0.5578 | 0.1959 | 0.064* | |
C2 | 0.28635 (17) | 0.4504 (5) | 0.23083 (7) | 0.0684 (9) | |
H2 | 0.2478 | 0.3763 | 0.2244 | 0.082* | |
C3 | 0.3084 (2) | 0.4529 (5) | 0.25708 (7) | 0.0744 (10) | |
H3 | 0.2847 | 0.3810 | 0.2685 | 0.089* | |
C4 | 0.36512 (18) | 0.5609 (5) | 0.26664 (6) | 0.0717 (9) | |
H4 | 0.3797 | 0.5625 | 0.2845 | 0.086* | |
C5 | 0.40110 (15) | 0.6682 (4) | 0.24986 (5) | 0.0555 (7) | |
H5 | 0.4396 | 0.7421 | 0.2564 | 0.067* | |
C6 | 0.37912 (13) | 0.6638 (4) | 0.22342 (5) | 0.0437 (6) | |
C7 | 0.44721 (14) | 0.6721 (4) | 0.18480 (5) | 0.0444 (6) | |
C8 | 0.50006 (14) | 0.8021 (3) | 0.17781 (5) | 0.0420 (6) | |
C9 | 0.50072 (14) | 0.9528 (4) | 0.19415 (5) | 0.0456 (6) | |
C10 | 0.54334 (19) | 1.1281 (4) | 0.19379 (6) | 0.0687 (9) | |
H10A | 0.5785 | 1.1131 | 0.1819 | 0.103* | |
H10B | 0.5663 | 1.1529 | 0.2111 | 0.103* | |
H10C | 0.5127 | 1.2314 | 0.1882 | 0.103* | |
C11 | 0.41219 (17) | 1.0827 (4) | 0.22160 (6) | 0.0616 (8) | |
H11A | 0.4433 | 1.1851 | 0.2271 | 0.092* | |
H11B | 0.3886 | 1.0401 | 0.2361 | 0.092* | |
H11C | 0.3775 | 1.1242 | 0.2077 | 0.092* | |
C12 | 0.54534 (13) | 0.6405 (4) | 0.14425 (5) | 0.0452 (6) | |
H12 | 0.5112 | 0.5480 | 0.1455 | 0.054* | |
C13 | 0.59681 (13) | 0.6213 (4) | 0.12500 (5) | 0.0415 (6) | |
C14 | 0.60530 (13) | 0.4538 (4) | 0.11141 (5) | 0.0433 (6) | |
C15 | 0.65691 (14) | 0.4400 (4) | 0.09442 (5) | 0.0437 (6) | |
C16 | 0.69984 (14) | 0.5901 (4) | 0.09035 (5) | 0.0490 (6) | |
H16 | 0.7345 | 0.5794 | 0.0790 | 0.059* | |
C17 | 0.69114 (14) | 0.7564 (4) | 0.10323 (5) | 0.0523 (7) | |
H17 | 0.7197 | 0.8591 | 0.1004 | 0.063* | |
C18 | 0.64046 (14) | 0.7720 (4) | 0.12029 (5) | 0.0478 (6) | |
H18 | 0.6353 | 0.8857 | 0.1288 | 0.057* | |
Cl3 | 0.25248 (4) | 0.64909 (11) | 0.143342 (13) | 0.0583 (2) | |
Cl4 | 0.23014 (5) | 0.99750 (14) | 0.178557 (15) | 0.0763 (3) | |
O2 | 0.31708 (11) | 0.3620 (3) | 0.07082 (4) | 0.0662 (6) | |
N4 | 0.40425 (12) | 0.3307 (3) | 0.04347 (4) | 0.0526 (6) | |
N5 | 0.45955 (11) | 0.4450 (3) | 0.03600 (4) | 0.0516 (6) | |
N6 | 0.40656 (11) | 0.7227 (3) | 0.08800 (4) | 0.0477 (5) | |
C19 | 0.35006 (17) | 0.2526 (5) | −0.00039 (6) | 0.0721 (9) | |
H19 | 0.3543 | 0.3770 | −0.0056 | 0.087* | |
C20 | 0.32156 (19) | 0.1161 (8) | −0.01809 (7) | 0.0907 (13) | |
H20 | 0.3075 | 0.1489 | −0.0354 | 0.109* | |
C21 | 0.3142 (2) | −0.0650 (7) | −0.01013 (9) | 0.0992 (15) | |
H21 | 0.2954 | −0.1557 | −0.0220 | 0.119* | |
C22 | 0.3344 (2) | −0.1121 (6) | 0.01507 (9) | 0.0962 (13) | |
H22 | 0.3284 | −0.2355 | 0.0204 | 0.115* | |
C23 | 0.36350 (18) | 0.0172 (5) | 0.03292 (7) | 0.0703 (9) | |
H23 | 0.3774 | −0.0178 | 0.0502 | 0.084* | |
C24 | 0.37168 (14) | 0.1989 (4) | 0.02494 (5) | 0.0500 (7) | |
C25 | 0.37179 (14) | 0.4180 (4) | 0.06310 (5) | 0.0478 (6) | |
C26 | 0.41562 (13) | 0.5815 (4) | 0.07008 (5) | 0.0451 (6) | |
C27 | 0.46719 (13) | 0.5892 (4) | 0.05380 (5) | 0.0479 (6) | |
C28 | 0.52484 (15) | 0.7318 (5) | 0.05331 (6) | 0.0648 (8) | |
H28A | 0.5195 | 0.8272 | 0.0662 | 0.097* | |
H28B | 0.5219 | 0.7883 | 0.0363 | 0.097* | |
H28C | 0.5701 | 0.6715 | 0.0572 | 0.097* | |
C29 | 0.52048 (16) | 0.3390 (5) | 0.02875 (7) | 0.0732 (9) | |
H29A | 0.5546 | 0.4246 | 0.0229 | 0.110* | |
H29B | 0.5050 | 0.2527 | 0.0149 | 0.110* | |
H29C | 0.5419 | 0.2702 | 0.0437 | 0.110* | |
C30 | 0.36197 (14) | 0.7055 (4) | 0.10466 (5) | 0.0465 (6) | |
H30 | 0.3361 | 0.5947 | 0.1054 | 0.056* | |
C31 | 0.35154 (13) | 0.8601 (4) | 0.12256 (5) | 0.0439 (6) | |
C32 | 0.30227 (13) | 0.8506 (4) | 0.14076 (5) | 0.0432 (6) | |
C33 | 0.29228 (15) | 1.0041 (4) | 0.15655 (5) | 0.0507 (7) | |
C34 | 0.33134 (17) | 1.1664 (4) | 0.15476 (6) | 0.0603 (8) | |
H34 | 0.3245 | 1.2689 | 0.1654 | 0.072* | |
C35 | 0.38016 (17) | 1.1756 (4) | 0.13717 (6) | 0.0639 (8) | |
H35 | 0.4069 | 1.2844 | 0.1361 | 0.077* | |
C36 | 0.38997 (15) | 1.0265 (4) | 0.12123 (6) | 0.0562 (7) | |
H36 | 0.4230 | 1.0361 | 0.1092 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0764 (5) | 0.0466 (4) | 0.0940 (6) | −0.0204 (4) | 0.0383 (5) | −0.0137 (4) |
Cl2 | 0.0797 (5) | 0.0608 (5) | 0.0569 (4) | 0.0085 (4) | 0.0166 (4) | −0.0150 (4) |
O1 | 0.0724 (13) | 0.0468 (11) | 0.0659 (12) | −0.0177 (10) | 0.0322 (10) | −0.0218 (10) |
N1 | 0.0545 (13) | 0.0417 (12) | 0.0414 (11) | −0.0069 (10) | 0.0146 (10) | −0.0099 (9) |
N2 | 0.0579 (14) | 0.0382 (11) | 0.0421 (11) | 0.0032 (10) | 0.0106 (10) | −0.0052 (9) |
N3 | 0.0529 (13) | 0.0410 (12) | 0.0464 (12) | −0.0039 (10) | 0.0136 (10) | −0.0014 (10) |
C1 | 0.0576 (17) | 0.0543 (17) | 0.0502 (15) | −0.0021 (14) | 0.0149 (13) | −0.0109 (13) |
C2 | 0.066 (2) | 0.065 (2) | 0.079 (2) | −0.0172 (16) | 0.0323 (17) | −0.0181 (17) |
C3 | 0.091 (3) | 0.072 (2) | 0.069 (2) | −0.0111 (19) | 0.0446 (19) | 0.0006 (18) |
C4 | 0.078 (2) | 0.093 (3) | 0.0476 (17) | −0.004 (2) | 0.0215 (16) | 0.0031 (17) |
C5 | 0.0501 (16) | 0.0691 (19) | 0.0489 (15) | −0.0040 (14) | 0.0121 (13) | −0.0057 (14) |
C6 | 0.0459 (15) | 0.0425 (14) | 0.0452 (14) | 0.0045 (12) | 0.0166 (11) | −0.0041 (11) |
C7 | 0.0516 (15) | 0.0403 (14) | 0.0430 (14) | −0.0003 (12) | 0.0121 (12) | −0.0059 (11) |
C8 | 0.0509 (15) | 0.0371 (13) | 0.0392 (13) | −0.0002 (11) | 0.0096 (11) | −0.0024 (11) |
C9 | 0.0575 (16) | 0.0368 (13) | 0.0425 (14) | −0.0023 (12) | 0.0059 (12) | 0.0013 (11) |
C10 | 0.094 (2) | 0.0503 (18) | 0.0640 (19) | −0.0190 (17) | 0.0189 (17) | −0.0101 (15) |
C11 | 0.077 (2) | 0.0498 (17) | 0.0584 (17) | 0.0109 (15) | 0.0101 (15) | −0.0148 (14) |
C12 | 0.0465 (15) | 0.0432 (14) | 0.0478 (14) | −0.0068 (12) | 0.0142 (12) | −0.0026 (12) |
C13 | 0.0420 (14) | 0.0419 (14) | 0.0417 (13) | −0.0032 (11) | 0.0097 (11) | −0.0001 (11) |
C14 | 0.0468 (15) | 0.0392 (14) | 0.0452 (14) | −0.0060 (11) | 0.0102 (11) | 0.0018 (11) |
C15 | 0.0481 (15) | 0.0450 (14) | 0.0384 (13) | 0.0029 (12) | 0.0070 (11) | 0.0017 (11) |
C16 | 0.0444 (15) | 0.0607 (17) | 0.0440 (14) | −0.0025 (13) | 0.0143 (11) | 0.0024 (13) |
C17 | 0.0503 (16) | 0.0521 (16) | 0.0568 (16) | −0.0101 (13) | 0.0160 (13) | 0.0031 (13) |
C18 | 0.0520 (16) | 0.0399 (14) | 0.0534 (15) | −0.0065 (12) | 0.0147 (12) | −0.0025 (12) |
Cl3 | 0.0682 (5) | 0.0619 (4) | 0.0465 (4) | −0.0197 (4) | 0.0142 (3) | −0.0035 (3) |
Cl4 | 0.0845 (6) | 0.0935 (6) | 0.0552 (4) | 0.0083 (5) | 0.0275 (4) | −0.0113 (4) |
O2 | 0.0703 (13) | 0.0747 (14) | 0.0603 (12) | −0.0309 (11) | 0.0359 (10) | −0.0214 (11) |
N4 | 0.0546 (14) | 0.0606 (15) | 0.0459 (12) | −0.0166 (11) | 0.0199 (10) | −0.0111 (11) |
N5 | 0.0432 (12) | 0.0679 (15) | 0.0467 (12) | −0.0105 (11) | 0.0187 (10) | −0.0078 (11) |
N6 | 0.0493 (13) | 0.0532 (13) | 0.0417 (12) | −0.0100 (11) | 0.0095 (10) | −0.0052 (10) |
C19 | 0.070 (2) | 0.095 (3) | 0.0527 (18) | −0.0213 (19) | 0.0152 (16) | 0.0014 (18) |
C20 | 0.076 (2) | 0.153 (4) | 0.0458 (18) | −0.039 (3) | 0.0159 (16) | −0.019 (2) |
C21 | 0.082 (3) | 0.133 (4) | 0.087 (3) | −0.040 (3) | 0.026 (2) | −0.061 (3) |
C22 | 0.099 (3) | 0.071 (3) | 0.118 (4) | −0.014 (2) | 0.010 (3) | −0.029 (2) |
C23 | 0.078 (2) | 0.060 (2) | 0.072 (2) | −0.0059 (17) | 0.0014 (17) | −0.0070 (17) |
C24 | 0.0469 (15) | 0.0605 (17) | 0.0454 (15) | −0.0062 (13) | 0.0177 (12) | −0.0131 (13) |
C25 | 0.0529 (16) | 0.0545 (16) | 0.0384 (13) | −0.0094 (13) | 0.0162 (12) | −0.0061 (12) |
C26 | 0.0463 (15) | 0.0508 (15) | 0.0392 (13) | −0.0071 (12) | 0.0094 (11) | −0.0024 (12) |
C27 | 0.0407 (14) | 0.0620 (17) | 0.0421 (14) | −0.0070 (13) | 0.0087 (11) | −0.0018 (13) |
C28 | 0.0489 (17) | 0.084 (2) | 0.0631 (18) | −0.0193 (16) | 0.0155 (14) | −0.0042 (17) |
C29 | 0.0502 (18) | 0.093 (3) | 0.079 (2) | −0.0001 (17) | 0.0200 (16) | −0.0169 (19) |
C30 | 0.0495 (15) | 0.0480 (15) | 0.0423 (14) | −0.0099 (12) | 0.0063 (12) | −0.0064 (12) |
C31 | 0.0448 (14) | 0.0464 (15) | 0.0397 (13) | −0.0059 (12) | 0.0016 (11) | −0.0050 (11) |
C32 | 0.0465 (14) | 0.0479 (15) | 0.0342 (12) | −0.0040 (12) | 0.0005 (11) | −0.0017 (11) |
C33 | 0.0574 (17) | 0.0593 (18) | 0.0352 (13) | 0.0097 (14) | 0.0038 (12) | −0.0027 (12) |
C34 | 0.081 (2) | 0.0454 (16) | 0.0532 (17) | 0.0020 (16) | 0.0015 (15) | −0.0146 (13) |
C35 | 0.075 (2) | 0.0501 (17) | 0.0663 (19) | −0.0169 (16) | 0.0094 (16) | −0.0145 (15) |
C36 | 0.0567 (17) | 0.0537 (17) | 0.0595 (17) | −0.0137 (14) | 0.0130 (14) | −0.0090 (14) |
Cl1—C14 | 1.728 (3) | Cl3—C32 | 1.728 (3) |
Cl2—C15 | 1.735 (3) | Cl4—C33 | 1.724 (3) |
O1—C7 | 1.226 (3) | O2—C25 | 1.219 (3) |
N1—C7 | 1.400 (3) | N4—C25 | 1.386 (3) |
N1—N2 | 1.404 (3) | N4—N5 | 1.413 (3) |
N1—C6 | 1.426 (3) | N4—C24 | 1.425 (3) |
N2—C9 | 1.369 (3) | N5—C27 | 1.370 (3) |
N2—C11 | 1.469 (3) | N5—C29 | 1.462 (4) |
N3—C12 | 1.270 (3) | N6—C30 | 1.276 (3) |
N3—C8 | 1.394 (3) | N6—C26 | 1.386 (3) |
C1—C6 | 1.380 (4) | C19—C24 | 1.374 (4) |
C1—C2 | 1.383 (4) | C19—C20 | 1.396 (5) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.366 (5) | C20—C21 | 1.361 (6) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.366 (5) | C21—C22 | 1.350 (6) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.387 (4) | C22—C23 | 1.369 (5) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.375 (4) | C23—C24 | 1.368 (4) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.438 (4) | C25—C26 | 1.449 (4) |
C8—C9 | 1.360 (3) | C26—C27 | 1.358 (3) |
C9—C10 | 1.486 (4) | C27—C28 | 1.492 (4) |
C10—H10A | 0.9600 | C28—H28A | 0.9600 |
C10—H10B | 0.9600 | C28—H28B | 0.9600 |
C10—H10C | 0.9600 | C28—H28C | 0.9600 |
C11—H11A | 0.9600 | C29—H29A | 0.9600 |
C11—H11B | 0.9600 | C29—H29B | 0.9600 |
C11—H11C | 0.9600 | C29—H29C | 0.9600 |
C12—C13 | 1.473 (3) | C30—C31 | 1.460 (4) |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C18 | 1.391 (3) | C31—C36 | 1.395 (4) |
C13—C14 | 1.399 (3) | C31—C32 | 1.397 (3) |
C14—C15 | 1.387 (3) | C32—C33 | 1.386 (4) |
C15—C16 | 1.372 (4) | C33—C34 | 1.379 (4) |
C16—C17 | 1.373 (4) | C34—C35 | 1.367 (4) |
C16—H16 | 0.9300 | C34—H34 | 0.9300 |
C17—C18 | 1.377 (4) | C35—C36 | 1.364 (4) |
C17—H17 | 0.9300 | C35—H35 | 0.9300 |
C18—H18 | 0.9300 | C36—H36 | 0.9300 |
C7—N1—N2 | 109.53 (19) | C25—N4—N5 | 110.2 (2) |
C7—N1—C6 | 123.4 (2) | C25—N4—C24 | 125.8 (2) |
N2—N1—C6 | 120.28 (19) | N5—N4—C24 | 118.3 (2) |
C9—N2—N1 | 106.27 (19) | C27—N5—N4 | 105.89 (19) |
C9—N2—C11 | 122.6 (2) | C27—N5—C29 | 121.9 (2) |
N1—N2—C11 | 116.3 (2) | N4—N5—C29 | 113.9 (2) |
C12—N3—C8 | 120.7 (2) | C30—N6—C26 | 121.2 (2) |
C6—C1—C2 | 119.4 (3) | C24—C19—C20 | 118.4 (4) |
C6—C1—H1 | 120.3 | C24—C19—H19 | 120.8 |
C2—C1—H1 | 120.3 | C20—C19—H19 | 120.8 |
C3—C2—C1 | 120.3 (3) | C21—C20—C19 | 120.4 (4) |
C3—C2—H2 | 119.9 | C21—C20—H20 | 119.8 |
C1—C2—H2 | 119.9 | C19—C20—H20 | 119.8 |
C2—C3—C4 | 120.2 (3) | C22—C21—C20 | 119.7 (4) |
C2—C3—H3 | 119.9 | C22—C21—H21 | 120.2 |
C4—C3—H3 | 119.9 | C20—C21—H21 | 120.2 |
C3—C4—C5 | 120.5 (3) | C21—C22—C23 | 121.6 (4) |
C3—C4—H4 | 119.8 | C21—C22—H22 | 119.2 |
C5—C4—H4 | 119.8 | C23—C22—H22 | 119.2 |
C6—C5—C4 | 119.1 (3) | C24—C23—C22 | 118.9 (4) |
C6—C5—H5 | 120.4 | C24—C23—H23 | 120.6 |
C4—C5—H5 | 120.4 | C22—C23—H23 | 120.6 |
C5—C6—C1 | 120.5 (2) | C23—C24—C19 | 120.9 (3) |
C5—C6—N1 | 122.1 (2) | C23—C24—N4 | 118.4 (3) |
C1—C6—N1 | 117.3 (2) | C19—C24—N4 | 120.7 (3) |
O1—C7—N1 | 123.6 (2) | O2—C25—N4 | 123.7 (2) |
O1—C7—C8 | 131.5 (2) | O2—C25—C26 | 131.8 (2) |
N1—C7—C8 | 104.8 (2) | N4—C25—C26 | 104.4 (2) |
C9—C8—N3 | 122.5 (2) | C27—C26—N6 | 122.1 (2) |
C9—C8—C7 | 108.0 (2) | C27—C26—C25 | 108.2 (2) |
N3—C8—C7 | 129.3 (2) | N6—C26—C25 | 129.3 (2) |
C8—C9—N2 | 110.7 (2) | C26—C27—N5 | 110.6 (2) |
C8—C9—C10 | 128.2 (2) | C26—C27—C28 | 128.2 (3) |
N2—C9—C10 | 121.1 (2) | N5—C27—C28 | 121.2 (2) |
C9—C10—H10A | 109.5 | C27—C28—H28A | 109.5 |
C9—C10—H10B | 109.5 | C27—C28—H28B | 109.5 |
H10A—C10—H10B | 109.5 | H28A—C28—H28B | 109.5 |
C9—C10—H10C | 109.5 | C27—C28—H28C | 109.5 |
H10A—C10—H10C | 109.5 | H28A—C28—H28C | 109.5 |
H10B—C10—H10C | 109.5 | H28B—C28—H28C | 109.5 |
N2—C11—H11A | 109.5 | N5—C29—H29A | 109.5 |
N2—C11—H11B | 109.5 | N5—C29—H29B | 109.5 |
H11A—C11—H11B | 109.5 | H29A—C29—H29B | 109.5 |
N2—C11—H11C | 109.5 | N5—C29—H29C | 109.5 |
H11A—C11—H11C | 109.5 | H29A—C29—H29C | 109.5 |
H11B—C11—H11C | 109.5 | H29B—C29—H29C | 109.5 |
N3—C12—C13 | 120.0 (2) | N6—C30—C31 | 119.9 (2) |
N3—C12—H12 | 120.0 | N6—C30—H30 | 120.1 |
C13—C12—H12 | 120.0 | C31—C30—H30 | 120.1 |
C18—C13—C14 | 117.6 (2) | C36—C31—C32 | 117.8 (2) |
C18—C13—C12 | 119.9 (2) | C36—C31—C30 | 119.9 (2) |
C14—C13—C12 | 122.5 (2) | C32—C31—C30 | 122.3 (2) |
C15—C14—C13 | 120.3 (2) | C33—C32—C31 | 120.0 (2) |
C15—C14—Cl1 | 119.6 (2) | C33—C32—Cl3 | 119.7 (2) |
C13—C14—Cl1 | 120.14 (19) | C31—C32—Cl3 | 120.3 (2) |
C16—C15—C14 | 120.9 (2) | C34—C33—C32 | 120.6 (3) |
C16—C15—Cl2 | 118.2 (2) | C34—C33—Cl4 | 118.6 (2) |
C14—C15—Cl2 | 120.9 (2) | C32—C33—Cl4 | 120.8 (2) |
C15—C16—C17 | 119.3 (2) | C35—C34—C33 | 119.6 (3) |
C15—C16—H16 | 120.4 | C35—C34—H34 | 120.2 |
C17—C16—H16 | 120.4 | C33—C34—H34 | 120.2 |
C16—C17—C18 | 120.5 (2) | C36—C35—C34 | 120.6 (3) |
C16—C17—H17 | 119.8 | C36—C35—H35 | 119.7 |
C18—C17—H17 | 119.8 | C34—C35—H35 | 119.7 |
C17—C18—C13 | 121.4 (2) | C35—C36—C31 | 121.4 (3) |
C17—C18—H18 | 119.3 | C35—C36—H36 | 119.3 |
C13—C18—H18 | 119.3 | C31—C36—H36 | 119.3 |
C7—N1—N2—C9 | 8.6 (3) | C25—N4—N5—C27 | 8.5 (3) |
C6—N1—N2—C9 | 160.7 (2) | C24—N4—N5—C27 | 163.6 (2) |
C7—N1—N2—C11 | 148.9 (2) | C25—N4—N5—C29 | 145.2 (3) |
C6—N1—N2—C11 | −59.0 (3) | C24—N4—N5—C29 | −59.7 (3) |
C6—C1—C2—C3 | 1.4 (5) | C24—C19—C20—C21 | 1.3 (5) |
C1—C2—C3—C4 | −0.2 (5) | C19—C20—C21—C22 | 0.2 (6) |
C2—C3—C4—C5 | −0.3 (5) | C20—C21—C22—C23 | −1.2 (7) |
C3—C4—C5—C6 | −0.3 (5) | C21—C22—C23—C24 | 0.5 (6) |
C4—C5—C6—C1 | 1.4 (4) | C22—C23—C24—C19 | 1.2 (5) |
C4—C5—C6—N1 | −176.3 (3) | C22—C23—C24—N4 | −177.9 (3) |
C2—C1—C6—C5 | −2.0 (4) | C20—C19—C24—C23 | −2.1 (5) |
C2—C1—C6—N1 | 175.8 (3) | C20—C19—C24—N4 | 177.0 (3) |
C7—N1—C6—C5 | 118.8 (3) | C25—N4—C24—C23 | −77.9 (4) |
N2—N1—C6—C5 | −29.3 (4) | N5—N4—C24—C23 | 131.2 (3) |
C7—N1—C6—C1 | −59.0 (3) | C25—N4—C24—C19 | 103.0 (3) |
N2—N1—C6—C1 | 152.9 (2) | N5—N4—C24—C19 | −47.8 (4) |
N2—N1—C7—O1 | 171.3 (2) | N5—N4—C25—O2 | 170.4 (3) |
C6—N1—C7—O1 | 20.3 (4) | C24—N4—C25—O2 | 17.6 (5) |
N2—N1—C7—C8 | −7.0 (3) | N5—N4—C25—C26 | −7.5 (3) |
C6—N1—C7—C8 | −158.1 (2) | C24—N4—C25—C26 | −160.2 (3) |
C12—N3—C8—C9 | −179.9 (3) | C30—N6—C26—C27 | −173.8 (3) |
C12—N3—C8—C7 | 4.7 (4) | C30—N6—C26—C25 | 13.1 (4) |
O1—C7—C8—C9 | −175.3 (3) | O2—C25—C26—C27 | −173.9 (3) |
N1—C7—C8—C9 | 2.9 (3) | N4—C25—C26—C27 | 3.6 (3) |
O1—C7—C8—N3 | 0.6 (5) | O2—C25—C26—N6 | −0.1 (5) |
N1—C7—C8—N3 | 178.8 (2) | N4—C25—C26—N6 | 177.4 (3) |
N3—C8—C9—N2 | −173.8 (2) | N6—C26—C27—N5 | −172.7 (2) |
C7—C8—C9—N2 | 2.4 (3) | C25—C26—C27—N5 | 1.6 (3) |
N3—C8—C9—C10 | 7.3 (5) | N6—C26—C27—C28 | 5.6 (5) |
C7—C8—C9—C10 | −176.5 (3) | C25—C26—C27—C28 | 179.9 (3) |
N1—N2—C9—C8 | −6.7 (3) | N4—N5—C27—C26 | −6.1 (3) |
C11—N2—C9—C8 | −143.9 (2) | C29—N5—C27—C26 | −138.5 (3) |
N1—N2—C9—C10 | 172.3 (2) | N4—N5—C27—C28 | 175.5 (3) |
C11—N2—C9—C10 | 35.0 (4) | C29—N5—C27—C28 | 43.1 (4) |
C8—N3—C12—C13 | −178.9 (2) | C26—N6—C30—C31 | −177.5 (2) |
N3—C12—C13—C18 | −10.1 (4) | N6—C30—C31—C36 | 0.5 (4) |
N3—C12—C13—C14 | 168.2 (3) | N6—C30—C31—C32 | 178.5 (2) |
C18—C13—C14—C15 | 1.5 (4) | C36—C31—C32—C33 | 0.7 (4) |
C12—C13—C14—C15 | −176.9 (2) | C30—C31—C32—C33 | −177.3 (2) |
C18—C13—C14—Cl1 | 180.0 (2) | C36—C31—C32—Cl3 | 179.7 (2) |
C12—C13—C14—Cl1 | 1.6 (4) | C30—C31—C32—Cl3 | 1.7 (4) |
C13—C14—C15—C16 | −0.8 (4) | C31—C32—C33—C34 | −0.9 (4) |
Cl1—C14—C15—C16 | −179.3 (2) | Cl3—C32—C33—C34 | −179.8 (2) |
C13—C14—C15—Cl2 | 178.5 (2) | C31—C32—C33—Cl4 | 178.3 (2) |
Cl1—C14—C15—Cl2 | 0.0 (3) | Cl3—C32—C33—Cl4 | −0.6 (3) |
C14—C15—C16—C17 | −0.4 (4) | C32—C33—C34—C35 | 0.2 (4) |
Cl2—C15—C16—C17 | −179.6 (2) | Cl4—C33—C34—C35 | −179.1 (2) |
C15—C16—C17—C18 | 0.8 (4) | C33—C34—C35—C36 | 0.7 (5) |
C16—C17—C18—C13 | 0.0 (4) | C34—C35—C36—C31 | −0.9 (5) |
C14—C13—C18—C17 | −1.1 (4) | C32—C31—C36—C35 | 0.2 (4) |
C12—C13—C18—C17 | 177.3 (3) | C30—C31—C36—C35 | 178.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O2i | 0.93 | 2.52 | 3.153 (4) | 125 |
C12—H12···Cl1 | 0.93 | 2.70 | 3.067 (3) | 104 |
C12—H12···O1 | 0.93 | 2.35 | 3.025 (3) | 129 |
C35—H35···O1ii | 0.93 | 2.65 | 3.221 (3) | 121 |
C30—H30···Cl3 | 0.93 | 2.68 | 3.059 (3) | 105 |
C30—H30···O2 | 0.93 | 2.42 | 3.061 (3) | 126 |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1, z. |
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