Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619006788/uk3178sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619006788/uk3178Isup2.hkl |
CCDC reference: 1915526
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL (Sheldrick, 2008).
[Cd(C24H18N6)2](ClO4)2·1.5C4H8O | Dx = 1.460 Mg m−3 |
Mr = 1200.34 | Cu Kα radiation, λ = 1.54184 Å |
Tetragonal, P43212 | Cell parameters from 4723 reflections |
a = 15.9167 (2) Å | θ = 4.4–70.6° |
c = 21.5498 (9) Å | µ = 4.68 mm−1 |
V = 5459.5 (2) Å3 | T = 100 K |
Z = 4 | Block, clear light colourless |
F(000) = 2456 | 0.14 × 0.12 × 0.05 mm |
SuperNova Dual Cu at zero Eos diffractometer | 5136 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 4787 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 70.7°, θmin = 5.0° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −12→18 |
Tmin = 0.845, Tmax = 1.000 | l = −12→25 |
11211 measured reflections |
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)] = 0.053 | w = 1/[σ2(Fo2) + (0.0913P)2 + 8.7372P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.152 | (Δ/σ)max = 0.002 |
S = 1.07 | Δρmax = 0.90 e Å−3 |
5136 reflections | Δρmin = −1.18 e Å−3 |
395 parameters | Extinction correction: SHELXL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
66 restraints | Extinction coefficient: 0.00027 (8) |
Primary atom site location: iterative | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.016 (11) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.5859 (3) | −0.3606 (3) | 0.1402 (3) | 0.0303 (11) | |
H1 | 0.5373 | −0.3895 | 0.1510 | 0.036* | |
C2 | 0.6153 (4) | −0.2975 (3) | 0.1807 (3) | 0.0299 (11) | |
H2 | 0.5866 | −0.2859 | 0.2173 | 0.036* | |
C3 | 0.6876 (4) | −0.2527 (3) | 0.1653 (3) | 0.0313 (12) | |
C4 | 0.7301 (4) | −0.2794 (4) | 0.1132 (3) | 0.0346 (12) | |
H4 | 0.7814 | −0.2551 | 0.1031 | 0.041* | |
C5 | 0.6971 (4) | −0.3426 (4) | 0.0754 (3) | 0.0350 (13) | |
H5 | 0.7269 | −0.3589 | 0.0403 | 0.042* | |
C6 | 0.7195 (3) | −0.1809 (3) | 0.2025 (3) | 0.0292 (11) | |
C7 | 0.6921 (3) | −0.1671 (4) | 0.2636 (3) | 0.0339 (13) | |
H7 | 0.6533 | −0.2034 | 0.2816 | 0.041* | |
C8 | 0.7227 (4) | −0.1001 (5) | 0.2970 (3) | 0.0477 (17) | |
H8 | 0.7039 | −0.0911 | 0.3373 | 0.057* | |
C9 | 0.7820 (4) | −0.0450 (4) | 0.2708 (3) | 0.0392 (14) | |
H9 | 0.8025 | 0.0000 | 0.2938 | 0.047* | |
C10 | 0.8100 (3) | −0.0586 (3) | 0.2101 (2) | 0.0253 (10) | |
C11 | 0.7787 (4) | −0.1262 (3) | 0.1773 (3) | 0.0294 (11) | |
H11 | 0.7978 | −0.1356 | 0.1371 | 0.035* | |
C12 | 0.8726 (3) | −0.0036 (3) | 0.1803 (2) | 0.0252 (10) | |
C13 | 0.9235 (3) | 0.0924 (3) | 0.1182 (2) | 0.0249 (10) | |
C14 | 0.9322 (3) | 0.1616 (3) | 0.0747 (2) | 0.0279 (10) | |
C15 | 1.0030 (4) | 0.1632 (4) | 0.0372 (3) | 0.0406 (14) | |
H15 | 1.0430 | 0.1208 | 0.0403 | 0.049* | |
C16 | 1.0141 (4) | 0.2282 (4) | −0.0049 (4) | 0.0473 (16) | |
H16 | 1.0620 | 0.2296 | −0.0296 | 0.057* | |
C17 | 0.9541 (4) | 0.2912 (4) | −0.0105 (3) | 0.0416 (14) | |
H17 | 0.9612 | 0.3335 | −0.0398 | 0.050* | |
C18 | 0.8838 (3) | 0.2914 (4) | 0.0274 (3) | 0.0308 (12) | |
C19 | 0.8718 (3) | 0.2261 (3) | 0.0692 (3) | 0.0284 (11) | |
H19 | 0.8238 | 0.2248 | 0.0937 | 0.034* | |
C20 | 0.8174 (3) | 0.3577 (4) | 0.0222 (3) | 0.0315 (12) | |
C21 | 0.8059 (4) | 0.4015 (4) | −0.0323 (3) | 0.0375 (14) | |
H21 | 0.8422 | 0.3926 | −0.0655 | 0.045* | |
C22 | 0.7401 (4) | 0.4593 (4) | −0.0382 (3) | 0.0379 (14) | |
H22 | 0.7342 | 0.4880 | −0.0755 | 0.045* | |
C23 | 0.6979 (4) | 0.4336 (4) | 0.0612 (3) | 0.0379 (13) | |
H23 | 0.6613 | 0.4439 | 0.0940 | 0.045* | |
C24 | 0.7625 (4) | 0.3764 (4) | 0.0699 (3) | 0.0367 (14) | |
H24 | 0.7690 | 0.3503 | 0.1082 | 0.044* | |
C25 | 0.6123 (12) | 0.9435 (15) | −0.006 (2) | 0.248 (9) | 0.75 |
H25A | 0.6609 | 0.9788 | −0.0100 | 0.371* | 0.75 |
H25B | 0.6032 | 0.9134 | −0.0439 | 0.371* | 0.75 |
H25C | 0.6211 | 0.9042 | 0.0273 | 0.371* | 0.75 |
C26 | 0.5344 (13) | 0.9984 (17) | 0.009 (2) | 0.247 (9) | 0.75 |
H26A | 0.5314 | 1.0425 | −0.0223 | 0.296* | 0.75 |
H26B | 0.4848 | 0.9637 | 0.0036 | 0.296* | 0.75 |
C27 | 0.5298 (15) | 1.0383 (17) | 0.070 (2) | 0.246 (9) | 0.75 |
C28 | 0.4534 (13) | 1.0838 (15) | 0.100 (2) | 0.244 (9) | 0.75 |
H28A | 0.4200 | 1.0441 | 0.1222 | 0.366* | 0.75 |
H28B | 0.4201 | 1.1089 | 0.0674 | 0.366* | 0.75 |
H28C | 0.4730 | 1.1268 | 0.1274 | 0.366* | 0.75 |
Cd1 | 0.557972 (19) | 0.557972 (19) | 0.0000 | 0.02464 (16) | |
Cl2 | 0.88222 (13) | 0.88222 (13) | 1.0000 | 0.0724 (8) | |
N1 | 0.6238 (3) | −0.3805 (3) | 0.0881 (2) | 0.0300 (9) | |
N2 | 0.9547 (3) | −0.0071 (3) | 0.1836 (2) | 0.0282 (9) | |
N3 | 0.9871 (3) | 0.0538 (3) | 0.1443 (2) | 0.0294 (9) | |
N4 | 0.8499 (3) | 0.0580 (3) | 0.1401 (2) | 0.0281 (9) | |
N5 | 0.7679 (3) | 0.0797 (4) | 0.1208 (3) | 0.0463 (14) | |
H5A | 0.7504 | 0.0435 | 0.0920 | 0.069* | |
H5B | 0.7336 | 0.0775 | 0.1534 | 0.069* | |
N6 | 0.6858 (3) | 0.4751 (3) | 0.0071 (2) | 0.0306 (10) | |
O1 | 0.9009 (10) | 0.8341 (11) | 1.0555 (6) | 0.080 (4) | 0.50 |
O2 | 0.9277 (12) | 0.9563 (10) | 1.0212 (9) | 0.133 (7) | 0.50 |
O3 | 0.9467 (10) | 0.8468 (11) | 0.9609 (7) | 0.106 (5) | 0.50 |
O4 | 0.2131 (12) | 0.3541 (8) | −0.0018 (11) | 0.131 (6) | 0.50 |
O5 | 0.3256 (6) | 0.3256 (6) | 0.0000 | 0.131 (4) | |
O6 | 0.2268 (5) | 0.2358 (5) | 0.0532 (3) | 0.085 (2) | |
O7 | 0.5932 (10) | 1.0264 (11) | 0.1180 (16) | 0.250 (9) | 0.75 |
O8 | 0.871 (2) | 0.8066 (12) | 1.0250 (17) | 0.23 (2) | 0.50 |
Cl1 | 0.2548 (3) | 0.2783 (3) | 0.0020 (6) | 0.0564 (17) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.024 (2) | 0.025 (3) | 0.043 (3) | −0.005 (2) | −0.004 (2) | 0.006 (2) |
C2 | 0.032 (3) | 0.022 (2) | 0.035 (3) | −0.003 (2) | −0.002 (2) | 0.001 (2) |
C3 | 0.032 (3) | 0.020 (2) | 0.042 (3) | 0.000 (2) | −0.002 (2) | 0.000 (2) |
C4 | 0.032 (3) | 0.027 (3) | 0.045 (3) | −0.011 (2) | 0.004 (3) | −0.004 (2) |
C5 | 0.029 (3) | 0.029 (3) | 0.047 (3) | −0.007 (2) | 0.000 (2) | −0.003 (2) |
C6 | 0.026 (3) | 0.023 (3) | 0.038 (3) | −0.002 (2) | −0.002 (2) | 0.002 (2) |
C7 | 0.023 (3) | 0.040 (3) | 0.039 (3) | −0.006 (2) | 0.000 (2) | 0.002 (2) |
C8 | 0.040 (4) | 0.064 (4) | 0.039 (3) | −0.020 (3) | 0.009 (3) | −0.012 (3) |
C9 | 0.033 (3) | 0.049 (4) | 0.036 (3) | −0.017 (3) | −0.001 (2) | −0.010 (3) |
C10 | 0.021 (2) | 0.024 (2) | 0.031 (2) | 0.000 (2) | −0.0049 (19) | −0.001 (2) |
C11 | 0.033 (3) | 0.024 (3) | 0.031 (3) | −0.003 (2) | 0.001 (2) | 0.000 (2) |
C12 | 0.021 (3) | 0.024 (2) | 0.031 (2) | −0.0001 (19) | −0.005 (2) | −0.003 (2) |
C13 | 0.022 (3) | 0.017 (2) | 0.035 (2) | −0.0023 (18) | 0.0009 (19) | −0.005 (2) |
C14 | 0.022 (2) | 0.025 (2) | 0.037 (3) | −0.001 (2) | 0.001 (2) | −0.003 (2) |
C15 | 0.031 (3) | 0.034 (3) | 0.057 (4) | 0.013 (2) | 0.006 (3) | 0.007 (3) |
C16 | 0.034 (3) | 0.046 (3) | 0.062 (4) | 0.016 (3) | 0.013 (3) | 0.020 (3) |
C17 | 0.034 (3) | 0.038 (3) | 0.053 (4) | 0.009 (2) | 0.011 (3) | 0.017 (3) |
C18 | 0.020 (2) | 0.026 (3) | 0.046 (3) | 0.000 (2) | 0.001 (2) | 0.005 (2) |
C19 | 0.024 (3) | 0.022 (2) | 0.040 (3) | −0.001 (2) | 0.002 (2) | 0.004 (2) |
C20 | 0.020 (3) | 0.029 (3) | 0.045 (3) | 0.002 (2) | −0.001 (2) | 0.002 (2) |
C21 | 0.029 (3) | 0.033 (3) | 0.051 (3) | 0.016 (2) | 0.004 (3) | 0.006 (3) |
C22 | 0.036 (3) | 0.034 (3) | 0.044 (3) | 0.012 (3) | −0.003 (3) | 0.006 (3) |
C23 | 0.032 (3) | 0.031 (3) | 0.051 (3) | 0.010 (2) | 0.011 (3) | 0.014 (3) |
C24 | 0.026 (3) | 0.035 (3) | 0.049 (3) | 0.009 (2) | 0.006 (3) | 0.013 (3) |
C25 | 0.077 (7) | 0.145 (11) | 0.52 (3) | 0.000 (8) | 0.047 (13) | 0.039 (15) |
C26 | 0.077 (6) | 0.145 (11) | 0.52 (3) | −0.003 (7) | 0.044 (12) | 0.039 (14) |
C27 | 0.078 (6) | 0.142 (10) | 0.52 (3) | 0.002 (7) | 0.038 (12) | 0.043 (14) |
C28 | 0.078 (7) | 0.138 (11) | 0.51 (3) | 0.001 (8) | 0.042 (12) | 0.043 (14) |
Cd1 | 0.01629 (17) | 0.01629 (17) | 0.0413 (3) | −0.00149 (17) | −0.00097 (15) | 0.00097 (15) |
Cl2 | 0.0803 (12) | 0.0803 (12) | 0.0566 (14) | −0.0261 (16) | 0.0070 (13) | −0.0070 (13) |
N1 | 0.023 (2) | 0.023 (2) | 0.045 (2) | −0.0032 (16) | −0.008 (2) | −0.002 (2) |
N2 | 0.025 (2) | 0.0184 (19) | 0.041 (2) | −0.0003 (16) | 0.0012 (19) | 0.0013 (18) |
N3 | 0.019 (2) | 0.022 (2) | 0.047 (2) | 0.0032 (18) | −0.0007 (18) | 0.002 (2) |
N4 | 0.021 (2) | 0.023 (2) | 0.040 (2) | −0.0022 (19) | −0.0069 (17) | 0.008 (2) |
N5 | 0.025 (2) | 0.054 (3) | 0.060 (3) | −0.006 (2) | −0.013 (2) | 0.024 (3) |
N6 | 0.019 (2) | 0.023 (2) | 0.050 (3) | −0.0006 (16) | −0.001 (2) | 0.004 (2) |
O1 | 0.060 (6) | 0.115 (10) | 0.065 (6) | −0.031 (7) | 0.002 (5) | 0.014 (7) |
O2 | 0.141 (8) | 0.126 (8) | 0.133 (8) | 0.004 (5) | −0.015 (5) | −0.015 (5) |
O3 | 0.103 (6) | 0.120 (6) | 0.094 (6) | 0.001 (5) | 0.014 (5) | −0.010 (5) |
O4 | 0.140 (8) | 0.119 (7) | 0.133 (7) | 0.001 (5) | −0.005 (5) | 0.002 (5) |
O5 | 0.133 (4) | 0.133 (4) | 0.128 (6) | −0.024 (5) | 0.012 (3) | −0.012 (3) |
O6 | 0.096 (5) | 0.105 (6) | 0.054 (3) | −0.030 (4) | −0.002 (3) | 0.022 (4) |
O7 | 0.083 (6) | 0.147 (10) | 0.52 (3) | 0.002 (7) | 0.030 (12) | 0.046 (14) |
O8 | 0.31 (4) | 0.054 (10) | 0.33 (5) | 0.018 (17) | 0.22 (4) | 0.037 (18) |
Cl1 | 0.063 (3) | 0.060 (3) | 0.0467 (17) | −0.024 (3) | −0.002 (3) | 0.003 (3) |
C1—H1 | 0.9300 | C24—H24 | 0.9300 |
C1—C2 | 1.409 (8) | C25—H25A | 0.9600 |
C1—N1 | 1.315 (8) | C25—H25B | 0.9600 |
C2—H2 | 0.9300 | C25—H25C | 0.9600 |
C2—C3 | 1.395 (8) | C25—C26 | 1.550 (10) |
C3—C4 | 1.377 (8) | C26—H26A | 0.9700 |
C3—C6 | 1.485 (7) | C26—H26B | 0.9700 |
C4—H4 | 0.9300 | C26—C27 | 1.47 (6) |
C4—C5 | 1.397 (8) | C27—C28 | 1.549 (10) |
C5—H5 | 0.9300 | C27—O7 | 1.45 (5) |
C5—N1 | 1.341 (7) | C28—H28A | 0.9600 |
C6—C7 | 1.405 (8) | C28—H28B | 0.9600 |
C6—C11 | 1.393 (7) | C28—H28C | 0.9600 |
C7—H7 | 0.9300 | Cd1—N1i | 2.379 (4) |
C7—C8 | 1.375 (9) | Cd1—N1ii | 2.379 (4) |
C8—H8 | 0.9300 | Cd1—N2iii | 2.325 (5) |
C8—C9 | 1.406 (9) | Cd1—N2iv | 2.325 (5) |
C9—H9 | 0.9300 | Cd1—N6 | 2.430 (4) |
C9—C10 | 1.400 (8) | Cd1—N6v | 2.430 (4) |
C10—C11 | 1.381 (7) | Cl2—O1vi | 1.452 (11) |
C10—C12 | 1.473 (7) | Cl2—O1 | 1.451 (11) |
C11—H11 | 0.9300 | Cl2—O2 | 1.457 (11) |
C12—N2 | 1.309 (7) | Cl2—O2vi | 1.457 (11) |
C12—N4 | 1.357 (7) | Cl2—O3 | 1.442 (11) |
C13—C14 | 1.453 (7) | Cl2—O3vi | 1.442 (11) |
C13—N3 | 1.311 (6) | Cl2—O8vi | 1.33 (2) |
C13—N4 | 1.378 (6) | Cl2—O8 | 1.33 (2) |
C14—C15 | 1.386 (8) | N1—Cd1vii | 2.379 (4) |
C14—C19 | 1.411 (7) | N2—Cd1viii | 2.325 (5) |
C15—H15 | 0.9300 | N2—N3 | 1.386 (6) |
C15—C16 | 1.388 (9) | N4—N5 | 1.414 (6) |
C16—H16 | 0.9300 | N5—H5A | 0.8901 |
C16—C17 | 1.390 (8) | N5—H5B | 0.8901 |
C17—H17 | 0.9300 | O2—O2vi | 1.12 (4) |
C17—C18 | 1.385 (8) | O2—O3vi | 1.35 (2) |
C18—C19 | 1.390 (8) | O3—O2vi | 1.35 (2) |
C18—C20 | 1.497 (8) | O4—Cl1v | 1.890 (14) |
C19—H19 | 0.9300 | O4—Cl1 | 1.379 (9) |
C20—C21 | 1.378 (8) | O5—Cl1 | 1.354 (14) |
C20—C24 | 1.382 (9) | O5—Cl1v | 1.354 (14) |
C21—H21 | 0.9300 | O6—Cl1v | 1.475 (12) |
C21—C22 | 1.399 (7) | O6—Cl1 | 1.369 (12) |
C22—H22 | 0.9300 | O8—O8vi | 1.81 (7) |
C22—N6 | 1.328 (8) | Cl1—O4v | 1.890 (14) |
C23—H23 | 0.9300 | Cl1—O6v | 1.475 (12) |
C23—C24 | 1.386 (8) | Cl1—Cl1v | 0.536 (12) |
C23—N6 | 1.353 (8) | ||
C2—C1—H1 | 118.4 | C27—C28—H28B | 109.5 |
N1—C1—H1 | 118.4 | C27—C28—H28C | 109.5 |
N1—C1—C2 | 123.2 (5) | H28A—C28—H28B | 109.5 |
C1—C2—H2 | 120.3 | H28A—C28—H28C | 109.5 |
C3—C2—C1 | 119.5 (5) | H28B—C28—H28C | 109.5 |
C3—C2—H2 | 120.3 | N1ii—Cd1—N1i | 105.9 (2) |
C2—C3—C6 | 123.2 (5) | N1ii—Cd1—N6 | 78.71 (17) |
C4—C3—C2 | 116.1 (5) | N1i—Cd1—N6 | 86.84 (17) |
C4—C3—C6 | 120.7 (5) | N1i—Cd1—N6v | 78.72 (17) |
C3—C4—H4 | 119.5 | N1ii—Cd1—N6v | 86.84 (17) |
C3—C4—C5 | 120.9 (5) | N2iv—Cd1—N1ii | 87.95 (15) |
C5—C4—H4 | 119.5 | N2iii—Cd1—N1ii | 159.30 (16) |
C4—C5—H5 | 118.9 | N2iii—Cd1—N1i | 87.95 (15) |
N1—C5—C4 | 122.2 (6) | N2iv—Cd1—N1i | 159.30 (16) |
N1—C5—H5 | 118.9 | N2iii—Cd1—N2iv | 83.4 (2) |
C7—C6—C3 | 121.3 (5) | N2iv—Cd1—N6 | 111.35 (15) |
C11—C6—C3 | 120.1 (5) | N2iii—Cd1—N6v | 111.35 (15) |
C11—C6—C7 | 118.6 (5) | N2iv—Cd1—N6v | 86.93 (15) |
C6—C7—H7 | 119.9 | N2iii—Cd1—N6 | 86.93 (15) |
C8—C7—C6 | 120.1 (5) | N6v—Cd1—N6 | 156.0 (2) |
C8—C7—H7 | 119.9 | O1—Cl2—O1vi | 153.6 (12) |
C7—C8—H8 | 119.6 | O1—Cl2—O2 | 93.9 (11) |
C7—C8—C9 | 120.7 (6) | O1vi—Cl2—O2 | 110.8 (11) |
C9—C8—H8 | 119.6 | O1—Cl2—O2vi | 110.8 (11) |
C8—C9—H9 | 120.2 | O1vi—Cl2—O2vi | 93.9 (11) |
C10—C9—C8 | 119.5 (6) | O2—Cl2—O2vi | 45.1 (15) |
C10—C9—H9 | 120.2 | O3—Cl2—O1 | 97.4 (10) |
C9—C10—C12 | 122.1 (5) | O3vi—Cl2—O1 | 88.5 (10) |
C11—C10—C9 | 118.9 (5) | O3vi—Cl2—O1vi | 97.4 (10) |
C11—C10—C12 | 119.0 (5) | O3—Cl2—O1vi | 88.5 (10) |
C6—C11—H11 | 118.9 | O3vi—Cl2—O2vi | 98.4 (13) |
C10—C11—C6 | 122.1 (5) | O3—Cl2—O2 | 98.4 (13) |
C10—C11—H11 | 118.9 | O3vi—Cl2—O2 | 55.7 (9) |
N2—C12—C10 | 128.8 (5) | O3—Cl2—O2vi | 55.7 (9) |
N2—C12—N4 | 109.3 (5) | O3—Cl2—O3vi | 153.9 (16) |
N4—C12—C10 | 121.8 (4) | O8vi—Cl2—O1 | 117 (2) |
N3—C13—C14 | 124.0 (4) | O8—Cl2—O1 | 38.3 (18) |
N3—C13—N4 | 108.8 (4) | O8—Cl2—O1vi | 117 (2) |
N4—C13—C14 | 127.2 (4) | O8vi—Cl2—O1vi | 38.3 (18) |
C15—C14—C13 | 117.9 (5) | O8vi—Cl2—O2vi | 132 (2) |
C15—C14—C19 | 119.4 (5) | O8—Cl2—O2vi | 133.0 (18) |
C19—C14—C13 | 122.7 (5) | O8—Cl2—O2 | 132 (2) |
C14—C15—H15 | 120.1 | O8vi—Cl2—O2 | 133.0 (18) |
C14—C15—C16 | 119.9 (5) | O8—Cl2—O3 | 88.6 (14) |
C16—C15—H15 | 120.1 | O8vi—Cl2—O3 | 110.9 (14) |
C15—C16—H16 | 119.8 | O8—Cl2—O3vi | 110.9 (14) |
C15—C16—C17 | 120.5 (6) | O8vi—Cl2—O3vi | 88.6 (14) |
C17—C16—H16 | 119.8 | O8vi—Cl2—O8 | 86 (4) |
C16—C17—H17 | 119.8 | C1—N1—C5 | 117.7 (5) |
C18—C17—C16 | 120.4 (6) | C1—N1—Cd1vii | 125.4 (4) |
C18—C17—H17 | 119.8 | C5—N1—Cd1vii | 114.0 (4) |
C17—C18—C19 | 119.4 (5) | C12—N2—Cd1viii | 138.9 (4) |
C17—C18—C20 | 121.9 (5) | C12—N2—N3 | 108.0 (4) |
C19—C18—C20 | 118.7 (5) | N3—N2—Cd1viii | 110.8 (3) |
C14—C19—H19 | 119.8 | C13—N3—N2 | 107.6 (4) |
C18—C19—C14 | 120.4 (5) | C12—N4—C13 | 106.2 (4) |
C18—C19—H19 | 119.8 | C12—N4—N5 | 127.7 (4) |
C21—C20—C18 | 120.9 (5) | C13—N4—N5 | 126.0 (4) |
C21—C20—C24 | 116.2 (5) | N4—N5—H5A | 109.5 |
C24—C20—C18 | 122.8 (5) | N4—N5—H5B | 108.8 |
C20—C21—H21 | 119.7 | H5A—N5—H5B | 109.5 |
C20—C21—C22 | 120.5 (6) | C22—N6—C23 | 116.6 (5) |
C22—C21—H21 | 119.7 | C22—N6—Cd1 | 127.0 (4) |
C21—C22—H22 | 118.5 | C23—N6—Cd1 | 116.0 (4) |
N6—C22—C21 | 123.1 (6) | O2vi—O2—Cl2 | 67.5 (8) |
N6—C22—H22 | 118.5 | O2vi—O2—O3vi | 125.1 (14) |
C24—C23—H23 | 118.6 | O3vi—O2—Cl2 | 61.6 (6) |
N6—C23—H23 | 118.6 | O2vi—O3—Cl2 | 62.7 (6) |
N6—C23—C24 | 122.8 (5) | Cl1—O4—Cl1v | 5.7 (6) |
C20—C24—C23 | 120.6 (6) | Cl1v—O5—Cl1 | 22.8 (5) |
C20—C24—H24 | 119.7 | Cl1—O6—Cl1v | 21.3 (5) |
C23—C24—H24 | 119.7 | Cl2—O8—O8vi | 47.0 (18) |
H25A—C25—H25B | 109.5 | O4—Cl1—O4v | 152.0 (15) |
H25A—C25—H25C | 109.5 | O4—Cl1—O6v | 109.8 (12) |
H25B—C25—H25C | 109.5 | O5—Cl1—O4v | 67.1 (7) |
C26—C25—H25A | 109.5 | O5—Cl1—O4 | 85.0 (9) |
C26—C25—H25B | 109.5 | O5—Cl1—O6v | 117.0 (8) |
C26—C25—H25C | 109.5 | O5—Cl1—O6 | 124.8 (9) |
C25—C26—H26A | 107.9 | O6v—Cl1—O4v | 82.2 (8) |
C25—C26—H26B | 107.9 | O6—Cl1—O4v | 90.1 (9) |
H26A—C26—H26B | 107.2 | O6—Cl1—O4 | 108.8 (12) |
C27—C26—C25 | 118 (3) | O6—Cl1—O6v | 107.9 (6) |
C27—C26—H26A | 107.9 | Cl1v—Cl1—O4 | 160 (2) |
C27—C26—H26B | 107.9 | Cl1v—Cl1—O4v | 14.7 (15) |
C26—C27—C28 | 127 (3) | Cl1v—Cl1—O5 | 78.6 (3) |
O7—C27—C26 | 123 (2) | Cl1v—Cl1—O6v | 68 (2) |
O7—C27—C28 | 109 (3) | Cl1v—Cl1—O6 | 91 (2) |
C27—C28—H28A | 109.5 | ||
C1—C2—C3—C4 | −5.8 (8) | Cd1viii—N2—N3—C13 | −166.4 (3) |
C1—C2—C3—C6 | 175.1 (5) | N1—C1—C2—C3 | 0.6 (9) |
C2—C1—N1—C5 | 4.8 (8) | N1i—Cd1—N6—C22 | −22.3 (5) |
C2—C1—N1—Cd1vii | −154.5 (4) | N1ii—Cd1—N6—C22 | −129.2 (5) |
C2—C3—C4—C5 | 5.9 (9) | N1ii—Cd1—N6—C23 | 58.3 (4) |
C2—C3—C6—C7 | 17.0 (8) | N1i—Cd1—N6—C23 | 165.2 (4) |
C2—C3—C6—C11 | −164.1 (6) | N2—C12—N4—C13 | 0.3 (6) |
C3—C4—C5—N1 | −0.7 (10) | N2—C12—N4—N5 | 176.5 (6) |
C3—C6—C7—C8 | 180.0 (6) | N2iii—Cd1—N6—C22 | 65.8 (5) |
C3—C6—C11—C10 | 179.9 (5) | N2iv—Cd1—N6—C22 | 147.5 (5) |
C4—C3—C6—C7 | −162.1 (6) | N2iii—Cd1—N6—C23 | −106.7 (4) |
C4—C3—C6—C11 | 16.8 (8) | N2iv—Cd1—N6—C23 | −25.0 (5) |
C4—C5—N1—C1 | −4.7 (9) | N3—C13—C14—C15 | 30.8 (8) |
C4—C5—N1—Cd1vii | 156.9 (5) | N3—C13—C14—C19 | −149.4 (5) |
C6—C3—C4—C5 | −175.0 (5) | N3—C13—N4—C12 | −0.4 (6) |
C6—C7—C8—C9 | −0.6 (11) | N3—C13—N4—N5 | −176.7 (5) |
C7—C6—C11—C10 | −1.1 (8) | N4—C12—N2—Cd1viii | 160.1 (4) |
C7—C8—C9—C10 | 0.2 (11) | N4—C12—N2—N3 | −0.1 (6) |
C8—C9—C10—C11 | −0.3 (9) | N4—C13—C14—C15 | −151.0 (6) |
C8—C9—C10—C12 | −179.4 (6) | N4—C13—C14—C19 | 28.8 (8) |
C9—C10—C11—C6 | 0.7 (8) | N4—C13—N3—N2 | 0.4 (6) |
C9—C10—C12—N2 | 84.9 (8) | N6—C23—C24—C20 | −1.3 (10) |
C9—C10—C12—N4 | −99.8 (6) | N6v—Cd1—N6—C22 | −75.1 (5) |
C10—C12—N2—Cd1viii | −24.1 (9) | N6v—Cd1—N6—C23 | 112.4 (4) |
C10—C12—N2—N3 | 175.7 (5) | O1—Cl2—O2—O2vi | 116 (2) |
C10—C12—N4—C13 | −175.8 (5) | O1vi—Cl2—O2—O2vi | −74 (2) |
C10—C12—N4—N5 | 0.4 (9) | O1—Cl2—O2—O3vi | −85.6 (13) |
C11—C6—C7—C8 | 1.1 (9) | O1vi—Cl2—O2—O3vi | 84.7 (14) |
C11—C10—C12—N2 | −94.2 (7) | O1—Cl2—O3—O2vi | −110.1 (14) |
C11—C10—C12—N4 | 81.1 (7) | O1vi—Cl2—O3—O2vi | 95.7 (14) |
C12—C10—C11—C6 | 179.9 (5) | O1vi—Cl2—O8—O8vi | −23 (2) |
C12—N2—N3—C13 | −0.2 (6) | O1—Cl2—O8—O8vi | 145 (3) |
C13—C14—C15—C16 | −179.8 (6) | O2vi—Cl2—O2—O3vi | 159 (3) |
C13—C14—C19—C18 | 179.2 (5) | O2—Cl2—O3—O2vi | −15 (2) |
C14—C13—N3—N2 | 178.8 (5) | O2—Cl2—O8—O8vi | 148.9 (15) |
C14—C13—N4—C12 | −178.8 (5) | O2vi—Cl2—O8—O8vi | −148.4 (14) |
C14—C13—N4—N5 | 4.9 (9) | O3—Cl2—O2—O2vi | 18 (2) |
C14—C15—C16—C17 | −0.9 (11) | O3vi—Cl2—O2—O2vi | −159 (3) |
C15—C14—C19—C18 | −1.1 (8) | O3—Cl2—O2—O3vi | 176.3 (6) |
C15—C16—C17—C18 | 2.1 (11) | O3vi—Cl2—O3—O2vi | −8.2 (12) |
C16—C17—C18—C19 | −2.7 (10) | O3—Cl2—O8—O8vi | −111.0 (15) |
C16—C17—C18—C20 | −179.3 (6) | O3vi—Cl2—O8—O8vi | 86.9 (19) |
C17—C18—C19—C14 | 2.2 (9) | O8—Cl2—O2—O2vi | 113 (3) |
C17—C18—C20—C21 | 24.2 (9) | O8vi—Cl2—O2—O2vi | −111 (3) |
C17—C18—C20—C24 | −158.4 (6) | O8vi—Cl2—O2—O3vi | 47 (3) |
C18—C20—C21—C22 | 175.7 (6) | O8—Cl2—O2—O3vi | −88 (2) |
C18—C20—C24—C23 | −174.9 (6) | O8vi—Cl2—O3—O2vi | 127 (2) |
C19—C14—C15—C16 | 0.4 (9) | O8—Cl2—O3—O2vi | −147 (2) |
C19—C18—C20—C21 | −152.4 (6) | Cl1v—O4—Cl1—O4v | 31 (6) |
C19—C18—C20—C24 | 25.0 (9) | Cl1v—O4—Cl1—O5 | 37 (7) |
C20—C18—C19—C14 | 178.9 (5) | Cl1v—O4—Cl1—O6 | 162 (8) |
C20—C21—C22—N6 | −0.2 (10) | Cl1v—O4—Cl1—O6v | −80 (8) |
C21—C20—C24—C23 | 2.6 (9) | Cl1v—O5—Cl1—O4v | 10 (3) |
C21—C22—N6—C23 | 1.6 (9) | Cl1v—O5—Cl1—O4 | −168 (3) |
C21—C22—N6—Cd1 | −170.9 (5) | Cl1v—O5—Cl1—O6v | −58 (2) |
C24—C20—C21—C22 | −1.9 (9) | Cl1v—O5—Cl1—O6 | 83 (3) |
C24—C23—N6—C22 | −0.9 (9) | Cl1v—O6—Cl1—O4v | −14.7 (15) |
C24—C23—N6—Cd1 | 172.4 (5) | Cl1v—O6—Cl1—O4 | −174 (2) |
C25—C26—C27—C28 | −170 (2) | Cl1v—O6—Cl1—O5 | −76.5 (15) |
C25—C26—C27—O7 | −2 (5) | Cl1v—O6—Cl1—O6v | 67.1 (15) |
Symmetry codes: (i) y+1, x, −z; (ii) x, y+1, z; (iii) −y+1/2, x−1/2, z−1/4; (iv) x−1/2, −y+1/2, −z+1/4; (v) y, x, −z; (vi) y, x, −z+2; (vii) x, y−1, z; (viii) y+1/2, −x+1/2, z+1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28B···O4ix | 0.96 | 2.42 | 3.34 (4) | 161 |
N5—H5A···O3x | 0.89 | 2.46 | 3.027 (12) | 122 |
N5—H5B···O4xi | 0.89 | 2.41 | 3.14 (2) | 140 |
N5—H5B···O7vii | 0.89 | 2.50 | 2.908 (17) | 109 |
Symmetry codes: (vii) x, y−1, z; (ix) y, x+1, −z; (x) y, x−1, −z+1; (xi) x+1/2, −y+1/2, −z+1/4. |