Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056376/om2085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056376/om2085Isup2.hkl |
CCDC reference: 636771
Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997).
C18H12Cl3N3 | Z = 4 |
Mr = 376.66 | F(000) = 768 |
Triclinic, P1 | Dx = 1.451 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.167 (3) Å | Cell parameters from 25 reflections |
b = 11.534 (3) Å | θ = 11.2–18.0° |
c = 15.799 (3) Å | µ = 0.54 mm−1 |
α = 86.02 (2)° | T = 100 K |
β = 69.58 (2)° | Fragment, colorless |
γ = 65.19 (2)° | 0.50 × 0.40 × 0.35 mm |
V = 1723.9 (8) Å3 |
Enraf–Nonius CAD-4 (with Oxford Cryostream) diffractometer | 6579 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 28.0°, θmin = 2.7° |
ω–2θ scans | h = −13→14 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→15 |
Tmin = 0.733, Tmax = 0.835 | l = −20→20 |
8712 measured reflections | 3 standard reflections every 60 min |
8304 independent reflections | intensity decay: none |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0472P)2 + 0.6927P] where P = (Fo2 + 2Fc2)/3 |
8304 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.32 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 | ||
Cl1A | 0.84155 (5) | −0.08739 (5) | 0.46285 (3) | 0.02717 (12) | |
Cl1B | 0.00492 (5) | 0.81058 (4) | 0.22548 (3) | 0.02203 (11) | |
Cl2A | 0.49257 (5) | 0.18103 (5) | 0.78499 (3) | 0.02402 (11) | |
Cl2B | 0.28166 (5) | 0.46654 (5) | −0.06605 (3) | 0.02244 (11) | |
Cl3A | 0.38770 (6) | 0.35259 (5) | 0.48135 (3) | 0.02840 (12) | |
Cl3B | 0.43543 (5) | 0.36464 (5) | 0.22889 (3) | 0.02397 (11) | |
N1A | 0.74388 (18) | −0.03516 (16) | 0.66182 (11) | 0.0238 (4) | |
N1B | 0.05879 (17) | 0.70632 (15) | 0.04152 (11) | 0.0197 (3) | |
N2A | 0.33516 (17) | 0.36559 (15) | 0.67904 (11) | 0.0198 (3) | |
N2B | 0.45487 (17) | 0.30480 (15) | 0.04198 (11) | 0.0192 (3) | |
N3A | 0.64508 (18) | 0.11543 (16) | 0.38708 (11) | 0.0204 (3) | |
N3B | 0.19296 (17) | 0.61323 (16) | 0.31071 (10) | 0.0198 (3) | |
C1A | 0.6935 (2) | 0.04332 (18) | 0.52507 (12) | 0.0186 (4) | |
C1B | 0.13169 (19) | 0.66150 (17) | 0.17401 (12) | 0.0173 (4) | |
C2A | 0.6593 (2) | 0.05758 (18) | 0.61887 (12) | 0.0181 (4) | |
C2B | 0.14965 (19) | 0.62593 (17) | 0.08622 (12) | 0.0170 (4) | |
C3A | 0.5392 (2) | 0.16439 (18) | 0.66907 (12) | 0.0184 (4) | |
C3B | 0.25683 (19) | 0.50699 (18) | 0.04350 (12) | 0.0170 (4) | |
C4A | 0.45644 (19) | 0.25736 (17) | 0.62703 (12) | 0.0178 (4) | |
C4B | 0.3450 (2) | 0.42335 (17) | 0.08702 (12) | 0.0174 (4) | |
C5A | 0.4919 (2) | 0.24029 (18) | 0.53337 (13) | 0.0184 (4) | |
C5B | 0.3233 (2) | 0.46138 (18) | 0.17544 (12) | 0.0181 (4) | |
C6A | 0.6101 (2) | 0.13284 (18) | 0.48165 (12) | 0.0177 (4) | |
C6B | 0.2155 (2) | 0.57862 (18) | 0.22015 (12) | 0.0175 (4) | |
C7A | 0.8478 (3) | −0.0258 (3) | 0.68476 (17) | 0.0375 (5) | |
H7A | 0.8723 | 0.0448 | 0.6771 | 0.045* | |
C7B | −0.0493 (2) | 0.6864 (2) | 0.03189 (15) | 0.0269 (4) | |
H7B | −0.0788 | 0.6215 | 0.0572 | 0.032* | |
C8A | 0.9090 (3) | −0.1365 (3) | 0.72042 (18) | 0.0472 (7) | |
H8A | 0.9835 | −0.1566 | 0.7429 | 0.057* | |
C8B | −0.1062 (2) | 0.7760 (2) | −0.02015 (16) | 0.0310 (5) | |
H8B | −0.1826 | 0.7850 | −0.0378 | 0.037* | |
C9A | 0.8428 (3) | −0.2160 (3) | 0.71827 (18) | 0.0465 (7) | |
H9A | 0.8649 | −0.2994 | 0.7386 | 0.056* | |
C9B | −0.0311 (2) | 0.8536 (2) | −0.04344 (15) | 0.0306 (5) | |
H9B | −0.0483 | 0.9242 | −0.0793 | 0.037* | |
C10A | 0.7415 (3) | −0.1522 (2) | 0.68194 (17) | 0.0364 (5) | |
H10A | 0.6802 | −0.1829 | 0.6722 | 0.044* | |
C10B | 0.0699 (2) | 0.8088 (2) | −0.00518 (14) | 0.0253 (4) | |
H10B | 0.1363 | 0.8423 | −0.0098 | 0.030* | |
C11A | 0.3328 (2) | 0.47954 (19) | 0.70277 (14) | 0.0249 (4) | |
H11A | 0.4113 | 0.5003 | 0.6863 | 0.030* | |
C11B | 0.5685 (2) | 0.29021 (19) | −0.03632 (13) | 0.0219 (4) | |
H11B | 0.5856 | 0.3575 | −0.0688 | 0.026* | |
C12A | 0.1967 (2) | 0.5572 (2) | 0.75440 (14) | 0.0266 (4) | |
H12A | 0.1636 | 0.6420 | 0.7799 | 0.032* | |
C12B | 0.6512 (2) | 0.1623 (2) | −0.05847 (15) | 0.0275 (4) | |
H12B | 0.7363 | 0.1243 | −0.1090 | 0.033* | |
C13A | 0.1148 (2) | 0.4895 (2) | 0.76308 (16) | 0.0324 (5) | |
H13A | 0.0165 | 0.5197 | 0.7960 | 0.039* | |
C13B | 0.5870 (2) | 0.0959 (2) | 0.00784 (16) | 0.0307 (5) | |
H13B | 0.6217 | 0.0055 | 0.0095 | 0.037* | |
C14A | 0.2018 (2) | 0.3721 (2) | 0.71564 (17) | 0.0329 (5) | |
H14A | 0.1744 | 0.3066 | 0.7092 | 0.039* | |
C14B | 0.4670 (2) | 0.18491 (19) | 0.06855 (15) | 0.0270 (4) | |
H14B | 0.4030 | 0.1676 | 0.1200 | 0.032* | |
C15A | 0.6265 (2) | 0.0284 (2) | 0.34371 (14) | 0.0268 (4) | |
H15A | 0.5871 | −0.0291 | 0.3721 | 0.032* | |
C15B | 0.2650 (2) | 0.6666 (2) | 0.33627 (15) | 0.0301 (5) | |
H15B | 0.3360 | 0.6901 | 0.2967 | 0.036* | |
C16A | 0.6747 (2) | 0.0391 (2) | 0.25277 (14) | 0.0310 (5) | |
H16A | 0.6740 | −0.0089 | 0.2065 | 0.037* | |
C16B | 0.2167 (3) | 0.6803 (2) | 0.42882 (15) | 0.0321 (5) | |
H16B | 0.2476 | 0.7156 | 0.4651 | 0.038* | |
C17A | 0.7255 (2) | 0.1341 (2) | 0.24008 (14) | 0.0320 (5) | |
H17A | 0.7660 | 0.1613 | 0.1834 | 0.038* | |
C17B | 0.1133 (2) | 0.6330 (2) | 0.46100 (14) | 0.0284 (5) | |
H17B | 0.0620 | 0.6303 | 0.5228 | 0.034* | |
C18A | 0.7064 (2) | 0.1805 (2) | 0.32327 (14) | 0.0288 (5) | |
H18A | 0.7310 | 0.2457 | 0.3349 | 0.035* | |
C18B | 0.0999 (2) | 0.5916 (2) | 0.38713 (13) | 0.0284 (5) | |
H18B | 0.0377 | 0.5547 | 0.3883 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0248 (2) | 0.0223 (2) | 0.0204 (2) | 0.00056 (19) | −0.00418 (18) | −0.00342 (18) |
Cl1B | 0.0185 (2) | 0.0197 (2) | 0.0217 (2) | −0.00394 (18) | −0.00379 (17) | −0.00595 (17) |
Cl2A | 0.0273 (2) | 0.0257 (2) | 0.0154 (2) | −0.0080 (2) | −0.00665 (18) | −0.00197 (17) |
Cl2B | 0.0225 (2) | 0.0248 (2) | 0.0177 (2) | −0.00610 (19) | −0.00807 (17) | −0.00494 (17) |
Cl3A | 0.0294 (3) | 0.0244 (2) | 0.0261 (2) | −0.0031 (2) | −0.0146 (2) | 0.00494 (19) |
Cl3B | 0.0290 (2) | 0.0200 (2) | 0.0252 (2) | −0.00752 (19) | −0.0161 (2) | 0.00388 (18) |
N1A | 0.0216 (8) | 0.0232 (9) | 0.0204 (8) | −0.0027 (7) | −0.0086 (7) | 0.0024 (7) |
N1B | 0.0176 (8) | 0.0195 (8) | 0.0221 (8) | −0.0058 (6) | −0.0095 (6) | 0.0003 (6) |
N2A | 0.0192 (8) | 0.0146 (7) | 0.0222 (8) | −0.0049 (6) | −0.0054 (6) | −0.0019 (6) |
N2B | 0.0190 (8) | 0.0157 (8) | 0.0210 (8) | −0.0059 (6) | −0.0058 (6) | −0.0029 (6) |
N3A | 0.0262 (9) | 0.0201 (8) | 0.0171 (8) | −0.0112 (7) | −0.0084 (7) | 0.0015 (6) |
N3B | 0.0240 (8) | 0.0220 (8) | 0.0147 (7) | −0.0110 (7) | −0.0065 (6) | −0.0001 (6) |
C1A | 0.0196 (9) | 0.0161 (9) | 0.0179 (9) | −0.0068 (7) | −0.0048 (7) | −0.0009 (7) |
C1B | 0.0145 (8) | 0.0159 (8) | 0.0192 (9) | −0.0064 (7) | −0.0025 (7) | −0.0028 (7) |
C2A | 0.0187 (9) | 0.0157 (9) | 0.0192 (9) | −0.0061 (7) | −0.0074 (7) | 0.0008 (7) |
C2B | 0.0173 (9) | 0.0167 (9) | 0.0180 (8) | −0.0073 (7) | −0.0070 (7) | −0.0002 (7) |
C3A | 0.0206 (9) | 0.0191 (9) | 0.0158 (8) | −0.0086 (7) | −0.0061 (7) | −0.0019 (7) |
C3B | 0.0193 (9) | 0.0190 (9) | 0.0149 (8) | −0.0098 (7) | −0.0058 (7) | −0.0009 (7) |
C4A | 0.0174 (9) | 0.0146 (8) | 0.0196 (9) | −0.0060 (7) | −0.0052 (7) | −0.0010 (7) |
C4B | 0.0186 (9) | 0.0144 (8) | 0.0197 (9) | −0.0079 (7) | −0.0058 (7) | −0.0002 (7) |
C5A | 0.0203 (9) | 0.0164 (9) | 0.0213 (9) | −0.0080 (7) | −0.0107 (7) | 0.0042 (7) |
C5B | 0.0202 (9) | 0.0175 (9) | 0.0196 (9) | −0.0092 (7) | −0.0093 (7) | 0.0038 (7) |
C6A | 0.0211 (9) | 0.0167 (9) | 0.0169 (8) | −0.0096 (7) | −0.0064 (7) | 0.0010 (7) |
C6B | 0.0187 (9) | 0.0196 (9) | 0.0162 (8) | −0.0110 (7) | −0.0046 (7) | −0.0009 (7) |
C7A | 0.0315 (12) | 0.0407 (14) | 0.0422 (13) | −0.0091 (11) | −0.0225 (11) | 0.0020 (11) |
C7B | 0.0226 (10) | 0.0257 (10) | 0.0344 (11) | −0.0092 (9) | −0.0128 (9) | −0.0009 (9) |
C8A | 0.0311 (13) | 0.0568 (18) | 0.0389 (14) | 0.0008 (12) | −0.0199 (11) | 0.0047 (12) |
C8B | 0.0241 (10) | 0.0283 (11) | 0.0383 (12) | −0.0016 (9) | −0.0188 (9) | −0.0043 (9) |
C9A | 0.0368 (14) | 0.0434 (15) | 0.0408 (14) | −0.0036 (12) | −0.0124 (11) | 0.0210 (12) |
C9B | 0.0339 (12) | 0.0247 (11) | 0.0327 (11) | −0.0067 (9) | −0.0187 (10) | 0.0049 (9) |
C10A | 0.0328 (12) | 0.0310 (12) | 0.0411 (13) | −0.0108 (10) | −0.0142 (10) | 0.0170 (10) |
C10B | 0.0276 (10) | 0.0232 (10) | 0.0265 (10) | −0.0104 (9) | −0.0121 (8) | 0.0048 (8) |
C11A | 0.0256 (10) | 0.0174 (9) | 0.0301 (10) | −0.0078 (8) | −0.0086 (8) | −0.0024 (8) |
C11B | 0.0178 (9) | 0.0242 (10) | 0.0225 (9) | −0.0078 (8) | −0.0062 (7) | −0.0026 (8) |
C12A | 0.0304 (11) | 0.0166 (9) | 0.0239 (10) | −0.0031 (8) | −0.0077 (8) | 0.0005 (8) |
C12B | 0.0186 (10) | 0.0278 (11) | 0.0321 (11) | −0.0043 (8) | −0.0095 (8) | −0.0082 (9) |
C13A | 0.0214 (10) | 0.0251 (11) | 0.0363 (12) | −0.0027 (9) | −0.0024 (9) | 0.0026 (9) |
C13B | 0.0285 (11) | 0.0159 (10) | 0.0458 (13) | −0.0041 (8) | −0.0164 (10) | −0.0041 (9) |
C14A | 0.0214 (10) | 0.0238 (11) | 0.0481 (14) | −0.0101 (9) | −0.0047 (10) | −0.0008 (10) |
C14B | 0.0269 (11) | 0.0188 (10) | 0.0350 (11) | −0.0098 (8) | −0.0105 (9) | 0.0026 (8) |
C15A | 0.0311 (11) | 0.0292 (11) | 0.0254 (10) | −0.0163 (9) | −0.0109 (9) | −0.0015 (8) |
C15B | 0.0375 (12) | 0.0364 (12) | 0.0264 (11) | −0.0245 (10) | −0.0113 (9) | 0.0002 (9) |
C16A | 0.0293 (11) | 0.0370 (12) | 0.0223 (10) | −0.0061 (10) | −0.0124 (9) | −0.0052 (9) |
C16B | 0.0410 (13) | 0.0339 (12) | 0.0249 (10) | −0.0144 (10) | −0.0162 (10) | −0.0040 (9) |
C17A | 0.0308 (11) | 0.0398 (13) | 0.0187 (10) | −0.0104 (10) | −0.0074 (9) | 0.0066 (9) |
C17B | 0.0330 (11) | 0.0263 (11) | 0.0180 (9) | −0.0067 (9) | −0.0067 (8) | −0.0007 (8) |
C18A | 0.0358 (12) | 0.0295 (11) | 0.0241 (10) | −0.0188 (10) | −0.0088 (9) | 0.0070 (8) |
C18B | 0.0311 (11) | 0.0372 (12) | 0.0185 (9) | −0.0197 (10) | −0.0040 (8) | 0.0020 (8) |
Cl1A—C1A | 1.718 (2) | C7B—H7B | 0.9500 |
Cl1B—C1B | 1.7234 (19) | C8A—C9A | 1.408 (4) |
Cl2A—C3A | 1.7209 (19) | C8A—H8A | 0.9500 |
Cl2B—C3B | 1.7201 (18) | C8B—C9B | 1.417 (3) |
Cl3A—C5A | 1.7208 (19) | C8B—H8B | 0.9500 |
Cl3B—C5B | 1.7206 (19) | C9A—C10A | 1.358 (3) |
N1A—C10A | 1.374 (3) | C9A—H9A | 0.9500 |
N1A—C7A | 1.376 (3) | C9B—C10B | 1.360 (3) |
N1A—C2A | 1.412 (2) | C9B—H9B | 0.9500 |
N1B—C10B | 1.377 (3) | C10A—H10A | 0.9500 |
N1B—C7B | 1.378 (3) | C10B—H10B | 0.9500 |
N1B—C2B | 1.417 (2) | C11A—C12A | 1.368 (3) |
N2A—C14A | 1.367 (3) | C11A—H11A | 0.9500 |
N2A—C11A | 1.379 (3) | C11B—C12B | 1.362 (3) |
N2A—C4A | 1.419 (2) | C11B—H11B | 0.9500 |
N2B—C14B | 1.382 (3) | C12A—C13A | 1.401 (3) |
N2B—C11B | 1.387 (2) | C12A—H12A | 0.9500 |
N2B—C4B | 1.414 (2) | C12B—C13B | 1.422 (3) |
N3A—C15A | 1.374 (3) | C12B—H12B | 0.9500 |
N3A—C18A | 1.376 (3) | C13A—C14A | 1.366 (3) |
N3A—C6A | 1.412 (2) | C13A—H13A | 0.9500 |
N3B—C15B | 1.366 (3) | C13B—C14B | 1.362 (3) |
N3B—C18B | 1.378 (3) | C13B—H13B | 0.9500 |
N3B—C6B | 1.419 (2) | C14A—H14A | 0.9500 |
C1A—C6A | 1.395 (3) | C14B—H14B | 0.9500 |
C1A—C2A | 1.398 (3) | C15A—C16A | 1.364 (3) |
C1B—C2B | 1.396 (3) | C15A—H15A | 0.9500 |
C1B—C6B | 1.396 (3) | C15B—C16B | 1.365 (3) |
C2A—C3A | 1.397 (3) | C15B—H15B | 0.9500 |
C2B—C3B | 1.399 (3) | C16A—C17A | 1.404 (3) |
C3A—C4A | 1.394 (3) | C16A—H16A | 0.9500 |
C3B—C4B | 1.398 (3) | C16B—C17B | 1.403 (3) |
C4A—C5A | 1.397 (3) | C16B—H16B | 0.9500 |
C4B—C5B | 1.401 (3) | C17A—C18A | 1.366 (3) |
C5A—C6A | 1.401 (3) | C17A—H17A | 0.9500 |
C5B—C6B | 1.396 (3) | C17B—C18B | 1.368 (3) |
C7A—C8A | 1.360 (4) | C17B—H17B | 0.9500 |
C7A—H7A | 0.9500 | C18A—H18A | 0.9500 |
C7B—C8B | 1.358 (3) | C18B—H18B | 0.9500 |
C10A—N1A—C7A | 109.30 (19) | C7B—C8B—C9B | 107.65 (19) |
C10A—N1A—C2A | 125.35 (19) | C7B—C8B—H8B | 126.2 |
C7A—N1A—C2A | 125.22 (19) | C9B—C8B—H8B | 126.2 |
C10B—N1B—C7B | 108.97 (17) | C10A—C9A—C8A | 107.8 (2) |
C10B—N1B—C2B | 126.53 (17) | C10A—C9A—H9A | 126.1 |
C7B—N1B—C2B | 124.30 (17) | C8A—C9A—H9A | 126.1 |
C14A—N2A—C11A | 108.95 (17) | C10B—C9B—C8B | 107.71 (19) |
C14A—N2A—C4A | 125.17 (17) | C10B—C9B—H9B | 126.1 |
C11A—N2A—C4A | 125.87 (17) | C8B—C9B—H9B | 126.1 |
C14B—N2B—C11B | 108.86 (17) | C9A—C10A—N1A | 107.6 (2) |
C14B—N2B—C4B | 125.81 (17) | C9A—C10A—H10A | 126.2 |
C11B—N2B—C4B | 125.32 (16) | N1A—C10A—H10A | 126.2 |
C15A—N3A—C18A | 108.97 (17) | C9B—C10B—N1B | 107.78 (19) |
C15A—N3A—C6A | 125.45 (17) | C9B—C10B—H10B | 126.1 |
C18A—N3A—C6A | 125.56 (17) | N1B—C10B—H10B | 126.1 |
C15B—N3B—C18B | 109.15 (17) | C12A—C11A—N2A | 107.48 (19) |
C15B—N3B—C6B | 125.63 (17) | C12A—C11A—H11A | 126.3 |
C18B—N3B—C6B | 125.14 (17) | N2A—C11A—H11A | 126.3 |
C6A—C1A—C2A | 121.28 (17) | C12B—C11B—N2B | 107.86 (18) |
C6A—C1A—Cl1A | 119.82 (14) | C12B—C11B—H11B | 126.1 |
C2A—C1A—Cl1A | 118.90 (14) | N2B—C11B—H11B | 126.1 |
C2B—C1B—C6B | 120.99 (17) | C11A—C12A—C13A | 107.86 (19) |
C2B—C1B—Cl1B | 119.25 (15) | C11A—C12A—H12A | 126.1 |
C6B—C1B—Cl1B | 119.76 (14) | C13A—C12A—H12A | 126.1 |
C3A—C2A—C1A | 118.66 (17) | C11B—C12B—C13B | 107.56 (19) |
C3A—C2A—N1A | 120.89 (17) | C11B—C12B—H12B | 126.2 |
C1A—C2A—N1A | 120.45 (17) | C13B—C12B—H12B | 126.2 |
C1B—C2B—C3B | 118.85 (17) | C14A—C13A—C12A | 107.6 (2) |
C1B—C2B—N1B | 121.07 (16) | C14A—C13A—H13A | 126.2 |
C3B—C2B—N1B | 120.04 (16) | C12A—C13A—H13A | 126.2 |
C4A—C3A—C2A | 121.23 (17) | C14B—C13B—C12B | 107.91 (19) |
C4A—C3A—Cl2A | 119.49 (14) | C14B—C13B—H13B | 126.0 |
C2A—C3A—Cl2A | 119.28 (15) | C12B—C13B—H13B | 126.0 |
C4B—C3B—C2B | 121.48 (17) | C13A—C14A—N2A | 108.1 (2) |
C4B—C3B—Cl2B | 120.10 (14) | C13A—C14A—H14A | 126.0 |
C2B—C3B—Cl2B | 118.40 (14) | N2A—C14A—H14A | 126.0 |
C3A—C4A—C5A | 119.03 (17) | C13B—C14B—N2B | 107.81 (19) |
C3A—C4A—N2A | 120.47 (17) | C13B—C14B—H14B | 126.1 |
C5A—C4A—N2A | 120.46 (17) | N2B—C14B—H14B | 126.1 |
C3B—C4B—C5B | 118.25 (17) | C16A—C15A—N3A | 108.1 (2) |
C3B—C4B—N2B | 120.67 (16) | C16A—C15A—H15A | 126.0 |
C5B—C4B—N2B | 121.07 (17) | N3A—C15A—H15A | 126.0 |
C4A—C5A—C6A | 120.89 (17) | C16B—C15B—N3B | 107.7 (2) |
C4A—C5A—Cl3A | 119.33 (15) | C16B—C15B—H15B | 126.1 |
C6A—C5A—Cl3A | 119.78 (14) | N3B—C15B—H15B | 126.1 |
C6B—C5B—C4B | 121.39 (17) | C15A—C16A—C17A | 107.4 (2) |
C6B—C5B—Cl3B | 119.06 (14) | C15A—C16A—H16A | 126.3 |
C4B—C5B—Cl3B | 119.51 (15) | C17A—C16A—H16A | 126.3 |
C1A—C6A—C5A | 118.86 (17) | C15B—C16B—C17B | 108.1 (2) |
C1A—C6A—N3A | 120.39 (17) | C15B—C16B—H16B | 126.0 |
C5A—C6A—N3A | 120.75 (17) | C17B—C16B—H16B | 126.0 |
C1B—C6B—C5B | 118.97 (17) | C18A—C17A—C16A | 108.22 (19) |
C1B—C6B—N3B | 120.71 (17) | C18A—C17A—H17A | 125.9 |
C5B—C6B—N3B | 120.31 (17) | C16A—C17A—H17A | 125.9 |
C8A—C7A—N1A | 107.3 (2) | C18B—C17B—C16B | 107.46 (19) |
C8A—C7A—H7A | 126.4 | C18B—C17B—H17B | 126.3 |
N1A—C7A—H7A | 126.4 | C16B—C17B—H17B | 126.3 |
C8B—C7B—N1B | 107.89 (19) | C17A—C18A—N3A | 107.4 (2) |
C8B—C7B—H7B | 126.1 | C17A—C18A—H18A | 126.3 |
N1B—C7B—H7B | 126.1 | N3A—C18A—H18A | 126.3 |
C7A—C8A—C9A | 108.0 (2) | C17B—C18B—N3B | 107.59 (19) |
C7A—C8A—H8A | 126.0 | C17B—C18B—H18B | 126.2 |
C9A—C8A—H8A | 126.0 | N3B—C18B—H18B | 126.2 |
C6A—C1A—C2A—C3A | −0.3 (3) | C18A—N3A—C6A—C1A | −103.9 (2) |
Cl1A—C1A—C2A—C3A | 179.70 (15) | C15A—N3A—C6A—C5A | −105.9 (2) |
C6A—C1A—C2A—N1A | 179.00 (18) | C18A—N3A—C6A—C5A | 75.8 (3) |
Cl1A—C1A—C2A—N1A | −1.0 (3) | C2B—C1B—C6B—C5B | 3.3 (3) |
C10A—N1A—C2A—C3A | 101.2 (2) | Cl1B—C1B—C6B—C5B | −176.19 (14) |
C7A—N1A—C2A—C3A | −83.2 (3) | C2B—C1B—C6B—N3B | −177.43 (17) |
C10A—N1A—C2A—C1A | −78.0 (3) | Cl1B—C1B—C6B—N3B | 3.1 (2) |
C7A—N1A—C2A—C1A | 97.6 (3) | C4B—C5B—C6B—C1B | −2.7 (3) |
C6B—C1B—C2B—C3B | −2.2 (3) | Cl3B—C5B—C6B—C1B | 174.96 (14) |
Cl1B—C1B—C2B—C3B | 177.27 (14) | C4B—C5B—C6B—N3B | 178.07 (17) |
C6B—C1B—C2B—N1B | 175.84 (17) | Cl3B—C5B—C6B—N3B | −4.3 (2) |
Cl1B—C1B—C2B—N1B | −4.7 (2) | C15B—N3B—C6B—C1B | −96.5 (2) |
C10B—N1B—C2B—C1B | 83.3 (2) | C18B—N3B—C6B—C1B | 87.3 (2) |
C7B—N1B—C2B—C1B | −102.4 (2) | C15B—N3B—C6B—C5B | 82.8 (3) |
C10B—N1B—C2B—C3B | −98.7 (2) | C18B—N3B—C6B—C5B | −93.5 (2) |
C7B—N1B—C2B—C3B | 75.6 (2) | C10A—N1A—C7A—C8A | −0.8 (3) |
C1A—C2A—C3A—C4A | −1.8 (3) | C2A—N1A—C7A—C8A | −177.0 (2) |
N1A—C2A—C3A—C4A | 178.98 (18) | C10B—N1B—C7B—C8B | −0.3 (2) |
C1A—C2A—C3A—Cl2A | 178.09 (14) | C2B—N1B—C7B—C8B | −175.39 (18) |
N1A—C2A—C3A—Cl2A | −1.2 (3) | N1A—C7A—C8A—C9A | 0.8 (3) |
C1B—C2B—C3B—C4B | 0.5 (3) | N1B—C7B—C8B—C9B | 0.0 (2) |
N1B—C2B—C3B—C4B | −177.62 (17) | C7A—C8A—C9A—C10A | −0.4 (3) |
C1B—C2B—C3B—Cl2B | −177.88 (14) | C7B—C8B—C9B—C10B | 0.2 (3) |
N1B—C2B—C3B—Cl2B | 4.1 (2) | C8A—C9A—C10A—N1A | −0.1 (3) |
C2A—C3A—C4A—C5A | 2.5 (3) | C7A—N1A—C10A—C9A | 0.6 (3) |
Cl2A—C3A—C4A—C5A | −177.38 (14) | C2A—N1A—C10A—C9A | 176.7 (2) |
C2A—C3A—C4A—N2A | −179.67 (17) | C8B—C9B—C10B—N1B | −0.4 (2) |
Cl2A—C3A—C4A—N2A | 0.5 (3) | C7B—N1B—C10B—C9B | 0.4 (2) |
C14A—N2A—C4A—C3A | −90.7 (3) | C2B—N1B—C10B—C9B | 175.39 (18) |
C11A—N2A—C4A—C3A | 87.6 (2) | C14A—N2A—C11A—C12A | −0.1 (2) |
C14A—N2A—C4A—C5A | 87.2 (3) | C4A—N2A—C11A—C12A | −178.61 (18) |
C11A—N2A—C4A—C5A | −94.5 (2) | C14B—N2B—C11B—C12B | −0.1 (2) |
C2B—C3B—C4B—C5B | 0.2 (3) | C4B—N2B—C11B—C12B | 179.80 (18) |
Cl2B—C3B—C4B—C5B | 178.47 (14) | N2A—C11A—C12A—C13A | 0.5 (2) |
C2B—C3B—C4B—N2B | −178.51 (17) | N2B—C11B—C12B—C13B | 0.0 (2) |
Cl2B—C3B—C4B—N2B | −0.2 (2) | C11A—C12A—C13A—C14A | −0.8 (3) |
C14B—N2B—C4B—C3B | −118.2 (2) | C11B—C12B—C13B—C14B | 0.1 (3) |
C11B—N2B—C4B—C3B | 61.9 (3) | C12A—C13A—C14A—N2A | 0.7 (3) |
C14B—N2B—C4B—C5B | 63.2 (3) | C11A—N2A—C14A—C13A | −0.4 (3) |
C11B—N2B—C4B—C5B | −116.7 (2) | C4A—N2A—C14A—C13A | 178.13 (19) |
C3A—C4A—C5A—C6A | −1.2 (3) | C12B—C13B—C14B—N2B | −0.1 (2) |
N2A—C4A—C5A—C6A | −179.03 (17) | C11B—N2B—C14B—C13B | 0.2 (2) |
C3A—C4A—C5A—Cl3A | 178.38 (14) | C4B—N2B—C14B—C13B | −179.76 (18) |
N2A—C4A—C5A—Cl3A | 0.5 (3) | C18A—N3A—C15A—C16A | −0.6 (2) |
C3B—C4B—C5B—C6B | 0.9 (3) | C6A—N3A—C15A—C16A | −179.09 (19) |
N2B—C4B—C5B—C6B | 179.62 (17) | C18B—N3B—C15B—C16B | −0.7 (3) |
C3B—C4B—C5B—Cl3B | −176.66 (14) | C6B—N3B—C15B—C16B | −177.38 (19) |
N2B—C4B—C5B—Cl3B | 2.0 (2) | N3A—C15A—C16A—C17A | 0.7 (2) |
C2A—C1A—C6A—C5A | 1.5 (3) | N3B—C15B—C16B—C17B | 0.5 (3) |
Cl1A—C1A—C6A—C5A | −178.45 (14) | C15A—C16A—C17A—C18A | −0.5 (3) |
C2A—C1A—C6A—N3A | −178.83 (17) | C15B—C16B—C17B—C18B | −0.2 (3) |
Cl1A—C1A—C6A—N3A | 1.2 (3) | C16A—C17A—C18A—N3A | 0.2 (3) |
C4A—C5A—C6A—C1A | −0.8 (3) | C15A—N3A—C18A—C17A | 0.2 (2) |
Cl3A—C5A—C6A—C1A | 179.67 (14) | C6A—N3A—C18A—C17A | 178.75 (19) |
C4A—C5A—C6A—N3A | 179.56 (17) | C16B—C17B—C18B—N3B | −0.2 (3) |
Cl3A—C5A—C6A—N3A | 0.0 (3) | C15B—N3B—C18B—C17B | 0.5 (3) |
C15A—N3A—C6A—C1A | 74.4 (3) | C6B—N3B—C18B—C17B | 177.26 (18) |