Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011342/wn2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011342/wn2004Isup2.hkl |
CCDC reference: 267511
Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995) in WinGX (Farrugia, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993) in WinGX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C6H10N3O2+·C2Cl3O2− | F(000) = 648 |
Mr = 318.54 | Dx = 1.661 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4505 (18) Å | Cell parameters from 25 reflections |
b = 25.769 (8) Å | θ = 10–14° |
c = 9.210 (2) Å | µ = 0.73 mm−1 |
β = 99.98 (2)° | T = 293 K |
V = 1274.0 (7) Å3 | Cut from a needle, colourless |
Z = 4 | 0.3 × 0.3 × 0.2 mm |
Enraf–Nonius CAD-4 diffractometer | 2155 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ω–2θ scans | h = 0→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→30 |
Tmin = 0.879, Tmax = 0.999 | l = −10→10 |
2539 measured reflections | 2 standard reflections every 60 min |
2300 independent reflections | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0685P)2 + 0.5935P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.36 e Å−3 |
2300 reflections | Δρmin = −0.29 e Å−3 |
427 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
263 restraints | Extinction coefficient: 0.080 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 253 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.21 (11) |
Experimental. Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. |
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 | Occ. (<1) | |
C1 | 0.7823 (11) | −0.1583 (2) | 0.6214 (6) | 0.0471 (12) | |
C2 | 1.0290 (9) | −0.14907 (19) | 0.4615 (6) | 0.0412 (11) | |
C3 | 0.8872 (8) | −0.10619 (18) | 0.4528 (5) | 0.0305 (9) | |
C4 | 0.8736 (8) | −0.06109 (17) | 0.3510 (5) | 0.0316 (9) | |
H4A | 0.7501 | −0.0687 | 0.2645 | 0.038* | |
H4B | 1.0332 | −0.0577 | 0.3189 | 0.038* | |
C5 | 0.8087 (7) | −0.00863 (15) | 0.4134 (4) | 0.0261 (8) | |
H6 | 0.8933 | −0.0058 | 0.5161 | 0.031* | |
C6 | 0.5258 (7) | −0.00231 (17) | 0.4078 (4) | 0.0287 (8) | |
C7 | 0.2809 (10) | −0.1625 (2) | 0.0293 (6) | 0.0471 (12) | |
C8 | 0.4055 (8) | −0.16412 (18) | −0.1124 (5) | 0.0338 (9) | |
C9 | 0.2924 (12) | 0.1685 (2) | 1.1207 (7) | 0.0536 (14) | |
C10 | 0.5306 (9) | 0.1619 (2) | 0.9564 (6) | 0.0411 (11) | |
C11 | 0.3932 (8) | 0.11810 (19) | 0.9482 (5) | 0.0329 (9) | |
C12 | 0.3634 (9) | 0.07396 (18) | 0.8430 (5) | 0.0365 (10) | |
H12A | 0.4445 | 0.0831 | 0.7607 | 0.044* | |
H12B | 0.1872 | 0.0698 | 0.8045 | 0.044* | |
C13 | 0.4668 (7) | 0.02098 (16) | 0.9041 (4) | 0.0272 (8) | |
H13 | 0.4279 | 0.0157 | 1.0030 | 0.033* | |
C14 | 0.7510 (7) | 0.01860 (18) | 0.9104 (4) | 0.0307 (9) | |
C15 | 0.7900 (13) | 0.1784 (2) | 0.5299 (7) | 0.0550 (14) | |
C16 | 0.9018 (9) | 0.17816 (18) | 0.3840 (6) | 0.0360 (10) | |
N1 | 0.9597 (8) | −0.18083 (14) | 0.5669 (5) | 0.0409 (9) | |
N2 | 0.7307 (8) | −0.11348 (16) | 0.5541 (5) | 0.0436 (10) | |
N3 | 0.9037 (6) | 0.03239 (14) | 0.3254 (4) | 0.0276 (7) | |
H3A | 1.0678 | 0.0289 | 0.3321 | 0.033* | |
H3B | 0.8698 | 0.0634 | 0.3596 | 0.033* | |
H3C | 0.8308 | 0.0295 | 0.2315 | 0.033* | |
N4 | 0.2435 (8) | 0.12337 (17) | 1.0513 (5) | 0.0464 (11) | |
N5 | 0.4653 (8) | 0.19219 (13) | 1.0648 (5) | 0.0423 (10) | |
N6 | 0.3388 (6) | −0.01904 (14) | 0.8022 (4) | 0.0283 (7) | |
H6A | 0.3858 | −0.0160 | 0.7147 | 0.057 (17)* | |
H6B | 0.1747 | −0.0147 | 0.7919 | 0.053 (16)* | |
H6C | 0.3793 | −0.0504 | 0.8389 | 0.027 (9)* | |
O1 | 0.4122 (6) | 0.02412 (17) | 0.3066 (4) | 0.0498 (9) | |
O2 | 0.4336 (5) | −0.02631 (14) | 0.5038 (3) | 0.0363 (7) | |
O3 | 0.4619 (7) | −0.20731 (13) | −0.1501 (4) | 0.0426 (8) | |
O4 | 0.4347 (9) | −0.12222 (15) | −0.1705 (5) | 0.0611 (12) | |
O5 | 0.8256 (5) | −0.00107 (17) | 0.8040 (4) | 0.0482 (9) | |
O6 | 0.8793 (6) | 0.03907 (17) | 1.0212 (4) | 0.0472 (9) | |
O7 | 0.9625 (8) | 0.22106 (14) | 0.3431 (4) | 0.0485 (9) | |
O8 | 0.9148 (9) | 0.13640 (16) | 0.3250 (5) | 0.0622 (12) | |
Cl1 | 0.0142 (14) | −0.1941 (9) | 0.0094 (10) | 0.076 (3) | 0.47 (3) |
Cl1' | 0.058 (2) | −0.2174 (5) | 0.0135 (11) | 0.069 (2) | 0.52 (3) |
Cl2 | 0.5056 (8) | −0.1878 (6) | 0.1829 (5) | 0.0790 (19) | 0.75 (3) |
Cl2' | 0.473 (4) | −0.1629 (13) | 0.1795 (16) | 0.069 (6) | 0.25 (3) |
Cl3' | 0.250 (3) | −0.0970 (2) | 0.0904 (8) | 0.088 (3) | 0.51 (2) |
Cl3 | 0.090 (3) | −0.1077 (3) | 0.0287 (16) | 0.102 (4) | 0.49 (2) |
Cl4' | 0.5827 (15) | 0.2359 (3) | 0.5189 (9) | 0.080 (2) | 0.401 (16) |
Cl4 | 0.5155 (9) | 0.2064 (4) | 0.5132 (5) | 0.085 (3) | 0.579 (16) |
Cl5 | 1.0098 (6) | 0.2116 (2) | 0.6769 (3) | 0.0731 (13) | 0.629 (13) |
Cl5' | 0.9769 (13) | 0.1746 (6) | 0.6735 (6) | 0.095 (4) | 0.353 (13) |
Cl6' | 0.7904 (7) | 0.11324 (12) | 0.6080 (3) | 0.0759 (13) | 0.621 (7) |
Cl6 | 0.5457 (12) | 0.1272 (2) | 0.5035 (7) | 0.099 (3) | 0.416 (8) |
H1' | 0.696 (9) | −0.177 (2) | 0.681 (5) | 0.052 (15)* | |
H1 | 1.019 (14) | −0.2105 (14) | 0.594 (9) | 0.09 (3)* | |
H2' | 1.144 (7) | −0.158 (2) | 0.404 (4) | 0.038 (13)* | |
H2 | 0.637 (8) | −0.0887 (14) | 0.571 (5) | 0.039 (14)* | |
H4 | 0.205 (18) | 0.099 (2) | 1.107 (8) | 0.08 (3)* | |
H5 | 0.510 (9) | 0.2227 (8) | 1.094 (5) | 0.033 (13)* | |
H9 | 0.231 (11) | 0.178 (2) | 1.204 (4) | 0.055 (16)* | |
H10 | 0.647 (8) | 0.172 (3) | 0.901 (5) | 0.052 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.062 (3) | 0.037 (3) | 0.049 (3) | 0.008 (2) | 0.030 (2) | 0.010 (2) |
C2 | 0.045 (3) | 0.031 (2) | 0.053 (3) | 0.005 (2) | 0.025 (2) | 0.004 (2) |
C3 | 0.034 (2) | 0.025 (2) | 0.034 (2) | 0.0008 (17) | 0.0108 (17) | 0.0017 (18) |
C4 | 0.033 (2) | 0.027 (2) | 0.038 (2) | 0.0012 (16) | 0.0143 (18) | 0.0016 (17) |
C5 | 0.0220 (17) | 0.028 (2) | 0.0294 (18) | 0.0008 (15) | 0.0065 (14) | 0.0003 (15) |
C6 | 0.0205 (17) | 0.0287 (18) | 0.037 (2) | −0.0004 (15) | 0.0063 (15) | −0.0026 (16) |
C7 | 0.054 (3) | 0.043 (3) | 0.052 (3) | 0.003 (2) | 0.028 (2) | 0.001 (2) |
C8 | 0.030 (2) | 0.028 (2) | 0.046 (2) | 0.0012 (18) | 0.0141 (18) | 0.006 (2) |
C9 | 0.067 (3) | 0.046 (3) | 0.056 (3) | −0.004 (3) | 0.033 (3) | −0.011 (2) |
C10 | 0.043 (3) | 0.034 (3) | 0.052 (3) | −0.009 (2) | 0.024 (2) | −0.004 (2) |
C11 | 0.029 (2) | 0.029 (2) | 0.043 (2) | 0.0020 (17) | 0.0124 (17) | 0.0027 (19) |
C12 | 0.038 (2) | 0.028 (2) | 0.043 (3) | 0.0014 (18) | 0.0061 (19) | −0.0013 (19) |
C13 | 0.0248 (18) | 0.0252 (18) | 0.0321 (19) | −0.0029 (15) | 0.0065 (15) | −0.0010 (15) |
C14 | 0.0228 (18) | 0.037 (2) | 0.033 (2) | −0.0031 (16) | 0.0058 (15) | 0.0018 (17) |
C15 | 0.066 (4) | 0.044 (3) | 0.063 (3) | −0.006 (3) | 0.034 (3) | −0.002 (3) |
C16 | 0.040 (2) | 0.025 (2) | 0.045 (2) | −0.0008 (18) | 0.013 (2) | 0.0045 (19) |
N1 | 0.049 (2) | 0.0262 (19) | 0.051 (2) | 0.0047 (17) | 0.0191 (19) | 0.0097 (18) |
N2 | 0.050 (2) | 0.037 (2) | 0.052 (2) | 0.0124 (18) | 0.031 (2) | 0.0079 (19) |
N3 | 0.0205 (15) | 0.0268 (17) | 0.0355 (18) | −0.0009 (13) | 0.0048 (13) | 0.0028 (14) |
N4 | 0.050 (2) | 0.034 (2) | 0.062 (3) | −0.0082 (18) | 0.029 (2) | −0.001 (2) |
N5 | 0.053 (2) | 0.024 (2) | 0.052 (2) | −0.0056 (17) | 0.017 (2) | −0.0060 (18) |
N6 | 0.0221 (15) | 0.0248 (17) | 0.0389 (19) | −0.0007 (13) | 0.0074 (13) | −0.0010 (14) |
O1 | 0.0217 (14) | 0.064 (2) | 0.064 (2) | 0.0049 (15) | 0.0078 (13) | 0.0287 (18) |
O2 | 0.0285 (14) | 0.0451 (18) | 0.0378 (16) | 0.0006 (13) | 0.0127 (12) | 0.0044 (13) |
O3 | 0.056 (2) | 0.0255 (17) | 0.051 (2) | 0.0033 (15) | 0.0218 (16) | 0.0023 (14) |
O4 | 0.090 (3) | 0.0276 (19) | 0.079 (3) | 0.0097 (18) | 0.052 (2) | 0.0069 (17) |
O5 | 0.0235 (14) | 0.072 (2) | 0.0512 (19) | −0.0012 (15) | 0.0105 (13) | −0.0173 (17) |
O6 | 0.0338 (16) | 0.067 (2) | 0.0407 (18) | −0.0186 (16) | 0.0071 (14) | −0.0087 (16) |
O7 | 0.069 (2) | 0.0279 (18) | 0.054 (2) | −0.0077 (15) | 0.0253 (18) | −0.0013 (15) |
O8 | 0.097 (3) | 0.028 (2) | 0.074 (3) | −0.0065 (19) | 0.050 (2) | −0.0048 (17) |
Cl1 | 0.035 (2) | 0.108 (8) | 0.086 (3) | −0.018 (3) | 0.0171 (18) | 0.013 (4) |
Cl1' | 0.052 (3) | 0.067 (4) | 0.099 (3) | −0.022 (3) | 0.039 (2) | −0.006 (3) |
Cl2 | 0.0671 (18) | 0.125 (5) | 0.0430 (14) | 0.016 (2) | 0.0042 (10) | 0.010 (2) |
Cl2' | 0.052 (6) | 0.105 (11) | 0.047 (4) | −0.026 (6) | 0.004 (4) | −0.009 (5) |
Cl3' | 0.141 (7) | 0.063 (2) | 0.080 (3) | 0.025 (3) | 0.072 (4) | −0.007 (2) |
Cl3 | 0.130 (7) | 0.067 (3) | 0.135 (7) | 0.042 (4) | 0.100 (6) | 0.011 (4) |
Cl4' | 0.065 (3) | 0.054 (4) | 0.138 (5) | 0.008 (3) | 0.062 (3) | −0.005 (3) |
Cl4 | 0.042 (2) | 0.121 (6) | 0.093 (2) | 0.030 (3) | 0.0198 (15) | −0.007 (3) |
Cl5 | 0.084 (2) | 0.088 (3) | 0.0486 (15) | −0.0215 (17) | 0.0129 (12) | −0.0129 (15) |
Cl5' | 0.065 (4) | 0.172 (11) | 0.047 (3) | 0.025 (5) | 0.003 (2) | 0.018 (4) |
Cl6' | 0.117 (3) | 0.0544 (16) | 0.0664 (18) | −0.0120 (14) | 0.0431 (17) | 0.0116 (12) |
Cl6 | 0.131 (5) | 0.062 (3) | 0.128 (4) | −0.045 (3) | 0.089 (4) | −0.018 (3) |
C1—N1 | 1.301 (7) | C12—H12B | 0.9700 |
C1—N2 | 1.317 (7) | C13—N6 | 1.484 (5) |
C1—H1' | 0.92 (5) | C13—C14 | 1.541 (5) |
C2—C3 | 1.343 (7) | C13—H13 | 0.9800 |
C2—N1 | 1.372 (6) | C14—O5 | 1.233 (5) |
C2—H2' | 0.92 (4) | C14—O6 | 1.249 (5) |
C3—N2 | 1.382 (6) | C15—Cl5' | 1.526 (9) |
C3—C4 | 1.487 (6) | C15—C16 | 1.569 (7) |
C4—C5 | 1.534 (6) | C15—Cl4 | 1.644 (7) |
C4—H4A | 0.9700 | C15—Cl6' | 1.826 (7) |
C4—H4B | 0.9700 | C15—Cl5 | 1.854 (7) |
C5—N3 | 1.479 (5) | C15—Cl4' | 1.855 (9) |
C5—C6 | 1.542 (5) | C15—Cl6 | 1.859 (8) |
C5—H6 | 0.9800 | C16—O8 | 1.213 (6) |
C6—O1 | 1.231 (5) | C16—O7 | 1.231 (6) |
C6—O2 | 1.253 (5) | N1—H1 | 0.85 (5) |
C7—C8 | 1.573 (6) | N2—H2 | 0.85 (4) |
C7—Cl2' | 1.59 (2) | N3—H3A | 0.8900 |
C7—Cl1 | 1.648 (11) | N3—H3B | 0.8900 |
C7—Cl3 | 1.755 (8) | N3—H3C | 0.8900 |
C7—Cl3' | 1.797 (8) | N4—H4 | 0.86 (6) |
C7—Cl2 | 1.824 (8) | N5—H5 | 0.85 (3) |
C7—Cl1' | 1.853 (9) | N6—H6A | 0.8900 |
C8—O3 | 1.221 (6) | N6—H6B | 0.8900 |
C8—O4 | 1.227 (6) | N6—H6C | 0.8900 |
C9—N5 | 1.302 (8) | Cl1—Cl1' | 0.644 (10) |
C9—N4 | 1.332 (8) | Cl1—Cl3 | 2.27 (2) |
C9—H9 | 0.92 (4) | Cl2—Cl2' | 0.66 (3) |
C10—C11 | 1.350 (7) | Cl2'—Cl3' | 2.17 (4) |
C10—N5 | 1.362 (6) | Cl3'—Cl3 | 0.994 (9) |
C10—H10 | 0.92 (5) | Cl4'—Cl4 | 0.841 (6) |
C11—N4 | 1.362 (6) | Cl4—Cl6 | 2.050 (12) |
C11—C12 | 1.485 (7) | Cl5—Cl5' | 0.969 (14) |
C12—C13 | 1.545 (6) | Cl5'—Cl6' | 1.919 (17) |
C12—H12A | 0.9700 | Cl6'—Cl6 | 1.546 (8) |
N1—C1—N2 | 108.8 (4) | C16—C15—Cl4 | 113.8 (5) |
N1—C1—H1' | 119 (4) | Cl5'—C15—Cl6' | 69.2 (7) |
N2—C1—H1' | 131 (4) | C16—C15—Cl6' | 111.1 (4) |
C3—C2—N1 | 107.9 (4) | Cl4—C15—Cl6' | 112.3 (5) |
C3—C2—H2' | 128 (3) | Cl5'—C15—Cl5 | 31.5 (5) |
N1—C2—H2' | 124 (3) | C16—C15—Cl5 | 109.2 (4) |
C2—C3—N2 | 105.3 (4) | Cl4—C15—Cl5 | 109.1 (5) |
C2—C3—C4 | 130.3 (4) | Cl6'—C15—Cl5 | 100.4 (4) |
N2—C3—C4 | 124.2 (4) | Cl5'—C15—Cl4' | 114.0 (7) |
C3—C4—C5 | 116.2 (4) | C16—C15—Cl4' | 106.2 (4) |
C3—C4—H4A | 108.2 | Cl4—C15—Cl4' | 26.9 (2) |
C5—C4—H4A | 108.2 | Cl6'—C15—Cl4' | 135.6 (4) |
C3—C4—H4B | 108.2 | Cl5—C15—Cl4' | 89.0 (5) |
C5—C4—H4B | 108.2 | Cl5'—C15—Cl6 | 115.0 (7) |
H4A—C4—H4B | 107.4 | C16—C15—Cl6 | 105.1 (4) |
N3—C5—C4 | 107.4 (3) | Cl4—C15—Cl6 | 71.3 (5) |
N3—C5—C6 | 110.4 (3) | Cl6'—C15—Cl6 | 49.6 (3) |
C4—C5—C6 | 112.0 (3) | Cl5—C15—Cl6 | 141.3 (4) |
N3—C5—H6 | 109.0 | Cl4'—C15—Cl6 | 98.2 (5) |
C4—C5—H6 | 109.0 | O8—C16—O7 | 128.3 (5) |
C6—C5—H6 | 109.0 | O8—C16—C15 | 116.6 (4) |
O1—C6—O2 | 126.6 (4) | O7—C16—C15 | 115.1 (4) |
O1—C6—C5 | 116.9 (3) | C1—N1—C2 | 108.7 (4) |
O2—C6—C5 | 116.4 (3) | C1—N1—H1 | 124 (6) |
C8—C7—Cl2' | 114.1 (7) | C2—N1—H1 | 128 (6) |
C8—C7—Cl1 | 113.2 (6) | C1—N2—C3 | 109.3 (4) |
Cl2'—C7—Cl1 | 122.1 (7) | C1—N2—H2 | 131 (4) |
C8—C7—Cl3 | 111.1 (4) | C3—N2—H2 | 119 (4) |
Cl2'—C7—Cl3 | 108.1 (14) | C5—N3—H3A | 109.5 |
Cl1—C7—Cl3 | 83.4 (10) | C5—N3—H3B | 109.5 |
C8—C7—Cl3' | 111.2 (4) | H3A—N3—H3B | 109.5 |
Cl2'—C7—Cl3' | 79.4 (14) | C5—N3—H3C | 109.5 |
Cl1—C7—Cl3' | 111.7 (10) | H3A—N3—H3C | 109.5 |
Cl3—C7—Cl3' | 32.5 (3) | H3B—N3—H3C | 109.5 |
C8—C7—Cl2 | 107.8 (4) | C9—N4—C11 | 109.1 (4) |
Cl2'—C7—Cl2 | 21.0 (9) | C9—N4—H4 | 113 (6) |
Cl1—C7—Cl2 | 111.7 (6) | C11—N4—H4 | 126 (7) |
Cl3—C7—Cl2 | 127.5 (8) | C9—N5—C10 | 108.7 (4) |
Cl3'—C7—Cl2 | 100.3 (7) | C9—N5—H5 | 120 (4) |
C8—C7—Cl1' | 106.7 (4) | C10—N5—H5 | 131 (4) |
Cl2'—C7—Cl1' | 112.9 (10) | C13—N6—H6A | 109.5 |
Cl1—C7—Cl1' | 20.1 (4) | C13—N6—H6B | 109.5 |
Cl3—C7—Cl1' | 103.5 (7) | H6A—N6—H6B | 109.5 |
Cl3'—C7—Cl1' | 130.1 (6) | C13—N6—H6C | 109.5 |
Cl2—C7—Cl1' | 97.5 (7) | H6A—N6—H6C | 109.5 |
O3—C8—O4 | 128.3 (4) | H6B—N6—H6C | 109.5 |
O3—C8—C7 | 115.2 (4) | Cl1'—Cl1—C7 | 98.2 (11) |
O4—C8—C7 | 116.5 (5) | Cl1'—Cl1—Cl3 | 148.2 (13) |
N5—C9—N4 | 108.5 (5) | C7—Cl1—Cl3 | 50.3 (7) |
N5—C9—H9 | 127 (4) | Cl1—Cl1'—C7 | 61.7 (10) |
N4—C9—H9 | 124 (4) | Cl2'—Cl2—C7 | 58.8 (14) |
C11—C10—N5 | 107.9 (4) | Cl2—Cl2'—C7 | 100.2 (14) |
C11—C10—H10 | 130 (4) | Cl2—Cl2'—Cl3' | 154.3 (19) |
N5—C10—H10 | 122 (4) | C7—Cl2'—Cl3' | 54.6 (12) |
C10—C11—N4 | 105.7 (4) | Cl3—Cl3'—C7 | 71.4 (5) |
C10—C11—C12 | 132.4 (5) | Cl3—Cl3'—Cl2' | 112.3 (7) |
N4—C11—C12 | 121.4 (4) | C7—Cl3'—Cl2' | 46.0 (4) |
C11—C12—C13 | 116.6 (4) | Cl3'—Cl3—C7 | 76.1 (6) |
C11—C12—H12A | 108.1 | Cl3'—Cl3—Cl1 | 116.5 (7) |
C13—C12—H12A | 108.1 | C7—Cl3—Cl1 | 46.3 (4) |
C11—C12—H12B | 108.1 | Cl4—Cl4'—C15 | 62.4 (5) |
C13—C12—H12B | 108.1 | Cl4'—Cl4—C15 | 90.6 (5) |
H12A—C12—H12B | 107.3 | Cl4'—Cl4—Cl6 | 149.8 (6) |
N6—C13—C14 | 110.8 (3) | C15—Cl4—Cl6 | 59.2 (4) |
N6—C13—C12 | 106.4 (3) | Cl5'—Cl5—C15 | 55.3 (4) |
C14—C13—C12 | 110.5 (3) | Cl5—Cl5'—C15 | 93.3 (7) |
N6—C13—H13 | 109.7 | Cl5—Cl5'—Cl6' | 154.8 (6) |
C14—C13—H13 | 109.7 | C15—Cl5'—Cl6' | 62.8 (6) |
C12—C13—H13 | 109.7 | Cl6—Cl6'—C15 | 66.3 (3) |
O5—C14—O6 | 127.4 (4) | Cl6—Cl6'—Cl5' | 110.9 (3) |
O5—C14—C13 | 117.0 (3) | C15—Cl6'—Cl5' | 48.0 (3) |
O6—C14—C13 | 115.5 (4) | Cl6'—Cl6—C15 | 64.1 (3) |
Cl5'—C15—C16 | 116.2 (5) | Cl6'—Cl6—Cl4 | 105.8 (3) |
Cl5'—C15—Cl4 | 124.7 (5) | C15—Cl6—Cl4 | 49.5 (3) |
N1—C2—C3—N2 | −0.6 (6) | Cl1—C7—Cl3'—Cl3 | −31.4 (7) |
N1—C2—C3—C4 | −175.7 (4) | Cl2—C7—Cl3'—Cl3 | −149.9 (6) |
C2—C3—C4—C5 | −148.7 (5) | Cl1'—C7—Cl3'—Cl3 | −40.7 (8) |
N2—C3—C4—C5 | 37.1 (6) | C8—C7—Cl3'—Cl2' | −111.9 (6) |
C3—C4—C5—N3 | 157.0 (3) | Cl1—C7—Cl3'—Cl2' | 120.5 (6) |
C3—C4—C5—C6 | −81.6 (5) | Cl3—C7—Cl3'—Cl2' | 151.9 (8) |
N3—C5—C6—O1 | 19.0 (5) | Cl2—C7—Cl3'—Cl2' | 2.0 (6) |
C4—C5—C6—O1 | −100.6 (5) | Cl1'—C7—Cl3'—Cl2' | 111.2 (9) |
N3—C5—C6—O2 | −163.6 (4) | Cl2—Cl2'—Cl3'—Cl3 | 16 (4) |
C4—C5—C6—O2 | 76.8 (5) | C7—Cl2'—Cl3'—Cl3 | 28.9 (7) |
Cl2'—C7—C8—O3 | 83.5 (14) | Cl2—Cl2'—Cl3'—C7 | −12 (4) |
Cl1—C7—C8—O3 | −62.2 (9) | Cl2'—Cl3'—Cl3—C7 | −21.5 (6) |
Cl3—C7—C8—O3 | −154.0 (8) | C7—Cl3'—Cl3—Cl1 | 23.1 (5) |
Cl3'—C7—C8—O3 | 171.1 (6) | Cl2'—Cl3'—Cl3—Cl1 | 1.6 (9) |
Cl2—C7—C8—O3 | 62.0 (7) | C8—C7—Cl3—Cl3' | −96.7 (8) |
Cl1'—C7—C8—O3 | −41.9 (7) | Cl2'—C7—Cl3—Cl3' | 29.2 (8) |
Cl2'—C7—C8—O4 | −96.1 (14) | Cl1—C7—Cl3—Cl3' | 150.9 (7) |
Cl1—C7—C8—O4 | 118.2 (9) | Cl2—C7—Cl3—Cl3' | 38.4 (7) |
Cl3—C7—C8—O4 | 26.3 (9) | Cl1'—C7—Cl3—Cl3' | 149.1 (6) |
Cl3'—C7—C8—O4 | −8.6 (8) | C8—C7—Cl3—Cl1 | 112.4 (6) |
Cl2—C7—C8—O4 | −117.7 (7) | Cl2'—C7—Cl3—Cl1 | −121.7 (7) |
Cl1'—C7—C8—O4 | 138.4 (7) | Cl3'—C7—Cl3—Cl1 | −150.9 (7) |
N5—C10—C11—N4 | 1.0 (6) | Cl2—C7—Cl3—Cl1 | −112.4 (7) |
N5—C10—C11—C12 | 172.7 (5) | Cl1'—C7—Cl3—Cl1 | −1.7 (6) |
C10—C11—C12—C13 | 112.5 (6) | Cl1'—Cl1—Cl3—Cl3' | −23 (4) |
N4—C11—C12—C13 | −76.8 (6) | C7—Cl1—Cl3—Cl3' | −31.9 (6) |
C11—C12—C13—N6 | 159.7 (4) | Cl1'—Cl1—Cl3—C7 | 9 (3) |
C11—C12—C13—C14 | −80.0 (5) | Cl5'—C15—Cl4'—Cl4 | −119.8 (9) |
N6—C13—C14—O5 | 23.2 (5) | C16—C15—Cl4'—Cl4 | 110.9 (7) |
C12—C13—C14—O5 | −94.4 (5) | Cl6'—C15—Cl4'—Cl4 | −35.6 (10) |
N6—C13—C14—O6 | −159.8 (4) | Cl5—C15—Cl4'—Cl4 | −139.4 (7) |
C12—C13—C14—O6 | 82.6 (5) | Cl6—C15—Cl4'—Cl4 | 2.4 (7) |
Cl5'—C15—C16—O8 | 93.7 (9) | C15—Cl4'—Cl4—Cl6 | −4.2 (13) |
Cl4—C15—C16—O8 | −110.7 (7) | Cl5'—C15—Cl4—Cl4' | 74.5 (12) |
Cl6'—C15—C16—O8 | 17.2 (7) | C16—C15—Cl4—Cl4' | −78.8 (8) |
Cl5—C15—C16—O8 | 127.0 (5) | Cl6'—C15—Cl4—Cl4' | 153.9 (7) |
Cl4'—C15—C16—O8 | −138.3 (6) | Cl5—C15—Cl4—Cl4' | 43.5 (8) |
Cl6—C15—C16—O8 | −34.8 (7) | Cl6—C15—Cl4—Cl4' | −177.5 (8) |
Cl5'—C15—C16—O7 | −87.2 (9) | Cl5'—C15—Cl4—Cl6 | −108.0 (9) |
Cl4—C15—C16—O7 | 68.3 (7) | C16—C15—Cl4—Cl6 | 98.8 (5) |
Cl6'—C15—C16—O7 | −163.7 (4) | Cl6'—C15—Cl4—Cl6 | −28.6 (3) |
Cl5—C15—C16—O7 | −53.9 (6) | Cl5—C15—Cl4—Cl6 | −139.0 (5) |
Cl4'—C15—C16—O7 | 40.8 (7) | Cl4'—C15—Cl4—Cl6 | 177.5 (8) |
Cl6—C15—C16—O7 | 144.3 (5) | C16—C15—Cl5—Cl5' | −109.1 (7) |
N2—C1—N1—C2 | 0.9 (6) | Cl4—C15—Cl5—Cl5' | 125.9 (7) |
C3—C2—N1—C1 | −0.2 (6) | Cl6'—C15—Cl5—Cl5' | 7.7 (6) |
N1—C1—N2—C3 | −1.4 (7) | Cl4'—C15—Cl5—Cl5' | 144.1 (6) |
C2—C3—N2—C1 | 1.2 (6) | Cl6—C15—Cl5—Cl5' | 42.1 (8) |
C4—C3—N2—C1 | 176.7 (5) | C15—Cl5—Cl5'—Cl6' | −17.2 (12) |
N5—C9—N4—C11 | 0.5 (7) | C16—C15—Cl5'—Cl5 | 84.1 (7) |
C10—C11—N4—C9 | −0.9 (6) | Cl4—C15—Cl5'—Cl5 | −68.5 (9) |
C12—C11—N4—C9 | −173.8 (5) | Cl6'—C15—Cl5'—Cl5 | −171.9 (6) |
N4—C9—N5—C10 | 0.1 (7) | Cl4'—C15—Cl5'—Cl5 | −40.0 (7) |
C11—C10—N5—C9 | −0.7 (6) | Cl6—C15—Cl5'—Cl5 | −152.4 (5) |
C8—C7—Cl1—Cl1' | 74.7 (15) | C16—C15—Cl5'—Cl6' | −104.0 (6) |
Cl2'—C7—Cl1—Cl1' | −68 (2) | Cl4—C15—Cl5'—Cl6' | 103.4 (8) |
Cl3—C7—Cl1—Cl1' | −175.1 (17) | Cl5—C15—Cl5'—Cl6' | 171.9 (6) |
Cl3'—C7—Cl1—Cl1' | −158.8 (16) | Cl4'—C15—Cl5'—Cl6' | 131.9 (5) |
Cl2—C7—Cl1—Cl1' | −47.3 (19) | Cl6—C15—Cl5'—Cl6' | 19.5 (4) |
C8—C7—Cl1—Cl3 | −110.2 (7) | Cl5'—C15—Cl6'—Cl6 | 156.6 (4) |
Cl2'—C7—Cl1—Cl3 | 107.3 (17) | C16—C15—Cl6'—Cl6 | −92.3 (5) |
Cl3'—C7—Cl1—Cl3 | 16.3 (4) | Cl4—C15—Cl6'—Cl6 | 36.5 (4) |
Cl2—C7—Cl1—Cl3 | 127.8 (7) | Cl5—C15—Cl6'—Cl6 | 152.3 (4) |
Cl1'—C7—Cl1—Cl3 | 175.1 (17) | Cl4'—C15—Cl6'—Cl6 | 53.1 (7) |
Cl3—Cl1—Cl1'—C7 | −7 (2) | C16—C15—Cl6'—Cl5' | 111.1 (6) |
C8—C7—Cl1'—Cl1 | −112.3 (16) | Cl4—C15—Cl6'—Cl5' | −120.1 (5) |
Cl2'—C7—Cl1'—Cl1 | 122 (2) | Cl5—C15—Cl6'—Cl5' | −4.3 (3) |
Cl3—C7—Cl1'—Cl1 | 5.0 (17) | Cl4'—C15—Cl6'—Cl5' | −103.6 (8) |
Cl3'—C7—Cl1'—Cl1 | 26 (2) | Cl6—C15—Cl6'—Cl5' | −156.6 (4) |
Cl2—C7—Cl1'—Cl1 | 136.5 (16) | Cl5—Cl5'—Cl6'—Cl6 | −3.5 (16) |
C8—C7—Cl2—Cl2' | 111.0 (16) | C15—Cl5'—Cl6'—Cl6 | −22.9 (4) |
Cl1—C7—Cl2—Cl2' | −123.9 (19) | Cl5—Cl5'—Cl6'—C15 | 19.4 (14) |
Cl3—C7—Cl2—Cl2' | −25.3 (19) | Cl5'—Cl6'—Cl6—C15 | 18.4 (3) |
Cl3'—C7—Cl2—Cl2' | −5.5 (17) | C15—Cl6'—Cl6—Cl4 | −27.3 (3) |
Cl1'—C7—Cl2—Cl2' | −138.7 (17) | Cl5'—Cl6'—Cl6—Cl4 | −8.9 (4) |
C7—Cl2—Cl2'—Cl3' | 10 (3) | Cl5'—C15—Cl6—Cl6' | −24.2 (5) |
C8—C7—Cl2'—Cl2 | −76.8 (16) | C16—C15—Cl6—Cl6' | 105.0 (4) |
Cl1—C7—Cl2'—Cl2 | 65 (2) | Cl4—C15—Cl6—Cl6' | −144.5 (4) |
Cl3—C7—Cl2'—Cl2 | 159.1 (16) | Cl5—C15—Cl6—Cl6' | −46.9 (7) |
Cl3'—C7—Cl2'—Cl2 | 174.5 (17) | Cl4'—C15—Cl6—Cl6' | −145.6 (4) |
Cl1'—C7—Cl2'—Cl2 | 45 (2) | Cl5'—C15—Cl6—Cl4 | 120.3 (6) |
C8—C7—Cl2'—Cl3' | 108.6 (8) | C16—C15—Cl6—Cl4 | −110.5 (5) |
Cl1—C7—Cl2'—Cl3' | −109.0 (13) | Cl6'—C15—Cl6—Cl4 | 144.5 (4) |
Cl3—C7—Cl2'—Cl3' | −15.4 (4) | Cl5—C15—Cl6—Cl4 | 97.6 (7) |
Cl2—C7—Cl2'—Cl3' | −174.5 (17) | Cl4'—C15—Cl6—Cl4 | −1.1 (4) |
Cl1'—C7—Cl2'—Cl3' | −129.3 (8) | Cl4'—Cl4—Cl6—Cl6' | 37.8 (17) |
C8—C7—Cl3'—Cl3 | 96.2 (7) | C15—Cl4—Cl6—Cl6' | 32.9 (3) |
Cl2'—C7—Cl3'—Cl3 | −151.9 (8) | Cl4'—Cl4—Cl6—C15 | 4.9 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.89 | 1.94 | 2.815 (5) | 169 |
N3—H3B···O8 | 0.89 | 1.93 | 2.681 (5) | 141 |
N3—H3C···O6ii | 0.89 | 2.02 | 2.787 (5) | 144 |
N6—H6A···O2 | 0.89 | 2.02 | 2.889 (5) | 164 |
N6—H6B···O5iii | 0.89 | 1.96 | 2.839 (4) | 170 |
N6—H6C···O4iv | 0.89 | 1.88 | 2.713 (5) | 155 |
N1—H1···O7v | 0.85 (5) | 1.85 (3) | 2.671 (5) | 161 (8) |
N2—H2···O2 | 0.85 (4) | 1.99 (3) | 2.761 (5) | 150 (5) |
N4—H4···O6iii | 0.86 (6) | 2.39 (8) | 2.923 (6) | 122 (8) |
N5—H5···O3vi | 0.85 (3) | 1.88 (1) | 2.715 (5) | 168 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1; (iii) x−1, y, z; (iv) x, y, z+1; (v) −x+2, y−1/2, −z+1; (vi) −x+1, y+1/2, −z+1. |