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The adsorption behaviour of the Cd
II–MOF {[Cd(
L)
2(ClO
4)
2]·H
2O (
1), where
L is 4-amino-3,5-bis[3-(pyridin-4-yl)phenyl]-1,2,4-triazole, for butan-2-one was investigated in a single-crystal-to-single-crystal (SCSC) fashion. A new host–guest system that encapsulated butan-2-one molecules, namely poly[[bis{μ
3-4-amino-3,5-bis[3-(pyridin-4-yl)phenyl]-1,2,4-triazole}cadmium(II)] bis(perchlorate) butanone sesquisolvate], {[Cd(C
24H
18N
6)
2](ClO
4)
2·1.5C
4H
8O}
n, denoted C
4H
8O@Cd-MOF (
2), was obtained
via an SCSC transformation. MOF
2 crystallizes in the tetragonal space group
P4
32
12. The specific binding sites for butan-2-one in the host were determined by single-crystal X-ray diffraction studies. N—H
O and C—H
O hydrogen-bonding interactions and C—H
π interactions between the framework, ClO
4− anions and guest molecules co-operatively bind 1.5 butan-2-one molecules within the channels. The adsorption behaviour was further evidenced by
1H NMR, IR, TGA and powder X-ray diffraction experiments, which are consistent with the single-crystal X-ray analysis. A
1H NMR experiment demonstrates that the supramolecular interactions between the framework, ClO
4− anions and guest molecules in MOF
2 lead to a high butan-2-one uptake in the channel.
Supporting information
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).
Poly[[bis{µ
3-4-amino-3,5-bis[3-(pyridin-4-yl)phenyl]-1,2,4-triazole}cadmium(II)] bis(perchlorate) butanone sesquisolvate]
top
Crystal data top
[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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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. |
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