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A new asymmetric ligand, 5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole (L5), which contains two oxadiazole rings, was synthesized and characterized. The assembly of symmetric 2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole (L1) and asymmetric L5 with AgCO2CF3 in solution yielded two novel AgI complexes, namely catena-poly[[di-μ-trifluoroacetato-disilver(I)]-bis[μ-2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole]], [Ag2(C2F3O2)2(C12H8N4O)2]n or [Ag2(μ2-O2CCF3)2(L1)2]n (1), and bis(μ3-5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole)tetra-μ3-trifluoroacetato-tetrasilver(I) dichloromethane monosolvate, [Ag4(C2F3O2)4(C22H15N5O2)2]·CH2Cl2 or [Ag2(μ3-O2CCF3)2(L5)]2·CH2Cl2 (2). Complex 1 displays a one-dimensional ring–chain motif, where dinuclear Ag2(CF3CO2)2 units alternate with Ag2(L1)2 macrocycles. This structure is different from previously reported Ag–L1 complexes with different anions. Complex 2 features a tetranuclear supramolecular macrocycle, in which each ligand adopts a tridentate coordination mode with the oxadiazole ring next to the p-tolyl ring coordinated and that next to the pyridyl ring free. Two L5 ligands are bound to two Ag1 centres through two oxadiazole N and two pyridyl N atoms to form a macrocycle. The other two oxadiazole N atoms coordinate to the two Ag2 centres of the Ag2(O2CCF3)4 dimer. Each CF3CO2− anion adopts a μ3-coordination mode, bridging the Ag1 and Ag2 centres to form a tetranuclear silver(I) complex. This study indicates that the donor ability of the bridging oxadiazole rings can be tuned by electron-withdrawing and -donating substituents. The emission properties of ligands L1 and L5 and complexes 1 and 2 were also investigated in the solid state.
Supporting information
CCDC references: 1949312; 1949311; 1949310
For all structures, 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: SHELXS97 (Sheldrick, 2008) for exp_3343, exp_3265; SUPERFLIP (Palatinus & Chapuis, 2007) for exp_3309. For all structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
catena-Poly[[di-µ-trifluoroacetato-disilver(I)]-bis[µ-2,5-\
bis(pyridin-3-yl)-1,3,4-oxadiazole]] (exp_3343)
top
Crystal data top
[Ag2(C2F3O2)2(C12H8N4O)2] | Z = 1 |
Mr = 890.23 | F(000) = 436 |
Triclinic, P1 | Dx = 2.006 Mg m−3 |
a = 7.4159 (12) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.5352 (18) Å | Cell parameters from 2345 reflections |
c = 11.158 (2) Å | θ = 9.8–70.8° |
α = 78.970 (16)° | µ = 11.55 mm−1 |
β = 82.579 (14)° | T = 293 K |
γ = 72.591 (16)° | Block, colourless |
V = 736.8 (2) Å3 | 0.16 × 0.07 × 0.05 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 2606 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 2460 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.038 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 67.1°, θmin = 4.1° |
ω scans | h = −7→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.163, Tmax = 1.000 | l = −13→11 |
4467 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.174 | w = 1/[σ2(Fo2) + (0.1341P)2 + 0.9025P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2606 reflections | Δρmax = 1.57 e Å−3 |
246 parameters | Δρmin = −1.33 e Å−3 |
26 restraints | Extinction correction: SHELXL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0077 (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) |
N4 | −0.0250 (7) | 0.8101 (6) | 0.7640 (5) | 0.0416 (11) | |
C11 | 0.0595 (14) | 0.8031 (9) | 0.9639 (7) | 0.065 (2) | |
H11 | 0.0537 | 0.8525 | 1.0292 | 0.078* | |
C9 | 0.0676 (8) | 0.6670 (6) | 0.7695 (5) | 0.0384 (12) | |
H9 | 0.0702 | 0.6204 | 0.7030 | 0.046* | |
Ag1 | 0.14795 (6) | 0.05571 (5) | 0.40773 (3) | 0.0477 (3) | |
O1 | 0.2419 (6) | 0.3549 (5) | 0.7856 (4) | 0.0384 (9) | |
N1 | 0.2907 (7) | 0.0137 (6) | 0.5811 (5) | 0.0394 (11) | |
C1 | 0.3863 (9) | −0.1263 (7) | 0.6270 (6) | 0.0436 (13) | |
H1 | 0.3935 | −0.2029 | 0.5844 | 0.052* | |
N3 | 0.3568 (11) | 0.3429 (7) | 0.9618 (6) | 0.0629 (17) | |
N2 | 0.4162 (11) | 0.1994 (6) | 0.9255 (5) | 0.0589 (16) | |
C7 | 0.2582 (9) | 0.4268 (7) | 0.8766 (5) | 0.0408 (13) | |
C6 | 0.3448 (8) | 0.2133 (7) | 0.8239 (5) | 0.0405 (12) | |
C5 | 0.2798 (8) | 0.1211 (6) | 0.6445 (5) | 0.0371 (11) | |
H5 | 0.2136 | 0.2182 | 0.6139 | 0.045* | |
C4 | 0.3625 (8) | 0.0949 (7) | 0.7537 (5) | 0.0378 (12) | |
C8 | 0.1608 (9) | 0.5847 (7) | 0.8713 (6) | 0.0409 (12) | |
C3 | 0.4586 (9) | −0.0486 (7) | 0.8003 (6) | 0.0476 (14) | |
H3 | 0.5126 | −0.0702 | 0.8748 | 0.057* | |
C10 | −0.0302 (11) | 0.8750 (8) | 0.8617 (7) | 0.0537 (16) | |
H10 | −0.0990 | 0.9746 | 0.8590 | 0.064* | |
C12 | 0.1599 (12) | 0.6544 (8) | 0.9690 (6) | 0.0550 (17) | |
H12 | 0.2255 | 0.6025 | 1.0370 | 0.066* | |
C2 | 0.4728 (9) | −0.1600 (7) | 0.7332 (6) | 0.0474 (14) | |
H2 | 0.5413 | −0.2575 | 0.7607 | 0.057* | |
C14 | −0.2676 (10) | 0.4350 (9) | 0.6354 (7) | 0.0552 (16) | |
F1 | −0.4475 (11) | 0.4851 (9) | 0.6613 (13) | 0.160 (5) | |
C13 | −0.2026 (10) | 0.2810 (9) | 0.6161 (9) | 0.065 (2) | |
F3 | −0.2298 (19) | 0.5245 (10) | 0.5420 (12) | 0.186 (5) | |
F2 | −0.1809 (19) | 0.4675 (15) | 0.7096 (14) | 0.201 (6) | |
O2 | −0.250 (2) | 0.1776 (14) | 0.6816 (13) | 0.084 (5) | 0.54 (2) |
O3 | −0.1179 (14) | 0.2702 (13) | 0.5087 (8) | 0.058 (4) | 0.54 (2) |
O3' | −0.161 (3) | 0.205 (2) | 0.5347 (16) | 0.094 (6) | 0.46 (2) |
O2' | −0.187 (4) | 0.213 (3) | 0.7238 (16) | 0.142 (10) | 0.46 (2) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N4 | 0.056 (3) | 0.037 (3) | 0.034 (3) | −0.012 (2) | −0.013 (2) | −0.007 (2) |
C11 | 0.104 (6) | 0.053 (4) | 0.045 (4) | −0.015 (4) | −0.026 (4) | −0.020 (3) |
C9 | 0.052 (3) | 0.040 (3) | 0.026 (3) | −0.012 (2) | −0.012 (2) | −0.009 (2) |
Ag1 | 0.0614 (4) | 0.0467 (4) | 0.0317 (4) | −0.0055 (2) | −0.0176 (2) | −0.0050 (2) |
O1 | 0.051 (2) | 0.035 (2) | 0.030 (2) | −0.0071 (17) | −0.0160 (16) | −0.0047 (16) |
N1 | 0.043 (2) | 0.042 (3) | 0.032 (2) | −0.005 (2) | −0.0156 (19) | −0.006 (2) |
C1 | 0.051 (3) | 0.037 (3) | 0.041 (3) | −0.006 (2) | −0.014 (3) | −0.007 (3) |
N3 | 0.102 (5) | 0.046 (3) | 0.038 (3) | −0.007 (3) | −0.029 (3) | −0.010 (2) |
N2 | 0.097 (5) | 0.037 (3) | 0.041 (3) | −0.002 (3) | −0.040 (3) | −0.003 (2) |
C7 | 0.055 (3) | 0.044 (3) | 0.028 (3) | −0.014 (3) | −0.019 (2) | −0.006 (2) |
C6 | 0.046 (3) | 0.038 (3) | 0.036 (3) | −0.007 (2) | −0.012 (2) | −0.004 (2) |
C5 | 0.044 (3) | 0.032 (3) | 0.032 (3) | −0.004 (2) | −0.012 (2) | −0.002 (2) |
C4 | 0.041 (3) | 0.046 (3) | 0.027 (3) | −0.012 (2) | −0.007 (2) | −0.005 (2) |
C8 | 0.053 (3) | 0.040 (3) | 0.031 (3) | −0.014 (3) | −0.013 (2) | −0.004 (2) |
C3 | 0.053 (3) | 0.048 (4) | 0.038 (3) | −0.003 (3) | −0.021 (3) | −0.005 (3) |
C10 | 0.073 (4) | 0.043 (4) | 0.047 (4) | −0.010 (3) | −0.013 (3) | −0.016 (3) |
C12 | 0.089 (5) | 0.044 (4) | 0.034 (3) | −0.012 (3) | −0.031 (3) | −0.005 (3) |
C2 | 0.052 (3) | 0.034 (3) | 0.049 (4) | 0.004 (2) | −0.017 (3) | −0.006 (3) |
C14 | 0.056 (4) | 0.061 (4) | 0.055 (4) | −0.023 (3) | 0.000 (3) | −0.018 (3) |
F1 | 0.088 (4) | 0.073 (4) | 0.306 (15) | −0.009 (3) | 0.049 (7) | −0.069 (6) |
C13 | 0.048 (4) | 0.049 (4) | 0.096 (6) | −0.011 (3) | −0.006 (4) | −0.014 (4) |
F3 | 0.238 (13) | 0.091 (6) | 0.185 (11) | −0.044 (7) | 0.060 (9) | 0.029 (6) |
F2 | 0.211 (11) | 0.184 (10) | 0.260 (14) | −0.045 (9) | −0.113 (11) | −0.120 (10) |
O2 | 0.084 (5) | 0.081 (5) | 0.085 (5) | −0.025 (2) | −0.005 (2) | −0.013 (2) |
O3 | 0.061 (4) | 0.057 (4) | 0.056 (4) | −0.012 (2) | −0.0047 (19) | −0.013 (2) |
O3' | 0.095 (6) | 0.093 (6) | 0.095 (6) | −0.027 (3) | −0.010 (2) | −0.016 (2) |
O2' | 0.142 (10) | 0.137 (10) | 0.145 (10) | −0.038 (5) | −0.009 (4) | −0.020 (4) |
Geometric parameters (Å, º) top
N4—C9 | 1.325 (8) | N2—C6 | 1.280 (8) |
N4—Ag1i | 2.226 (5) | C7—C8 | 1.455 (9) |
N4—C10 | 1.344 (9) | C6—C4 | 1.460 (8) |
C11—H11 | 0.9300 | C5—H5 | 0.9300 |
C11—C10 | 1.356 (11) | C5—C4 | 1.381 (8) |
C11—C12 | 1.384 (11) | C4—C3 | 1.375 (9) |
C9—H9 | 0.9300 | C8—C12 | 1.379 (9) |
C9—C8 | 1.386 (9) | C3—H3 | 0.9300 |
Ag1—N4i | 2.226 (5) | C3—C2 | 1.385 (10) |
Ag1—Ag1ii | 3.0943 (10) | C10—H10 | 0.9300 |
Ag1—N1 | 2.236 (5) | C12—H12 | 0.9300 |
Ag1—O2ii | 2.482 (14) | C2—H2 | 0.9300 |
Ag1—O3 | 2.690 (9) | C14—F1 | 1.290 (10) |
Ag1—O3' | 2.696 (15) | C14—C13 | 1.451 (11) |
Ag1—O3'ii | 2.42 (2) | C14—F3 | 1.273 (11) |
O1—C7 | 1.366 (7) | C14—F2 | 1.245 (11) |
O1—C6 | 1.354 (7) | C13—O2 | 1.223 (13) |
N1—C1 | 1.347 (10) | C13—O3 | 1.286 (12) |
N1—C5 | 1.330 (8) | C13—O3' | 1.221 (14) |
C1—H1 | 0.9300 | C13—O2' | 1.254 (15) |
C1—C2 | 1.359 (10) | O2—Ag1ii | 2.482 (14) |
N3—N2 | 1.427 (9) | O3'—Ag1ii | 2.42 (2) |
N3—C7 | 1.272 (9) | | |
| | | |
C9—N4—Ag1i | 120.9 (4) | N2—C6—C4 | 126.5 (6) |
C9—N4—C10 | 118.2 (6) | N1—C5—H5 | 118.5 |
C10—N4—Ag1i | 120.6 (5) | N1—C5—C4 | 122.9 (5) |
C10—C11—H11 | 120.8 | C4—C5—H5 | 118.5 |
C10—C11—C12 | 118.5 (6) | C5—C4—C6 | 122.3 (5) |
C12—C11—H11 | 120.8 | C3—C4—C6 | 118.8 (5) |
N4—C9—H9 | 119.0 | C3—C4—C5 | 118.9 (5) |
N4—C9—C8 | 122.0 (5) | C9—C8—C7 | 121.2 (5) |
C8—C9—H9 | 119.0 | C12—C8—C9 | 119.0 (6) |
N4i—Ag1—Ag1ii | 112.71 (14) | C12—C8—C7 | 119.8 (6) |
N4i—Ag1—N1 | 155.8 (2) | C4—C3—H3 | 120.9 |
N4i—Ag1—O2ii | 92.4 (4) | C4—C3—C2 | 118.1 (6) |
N4i—Ag1—O3 | 82.1 (3) | C2—C3—H3 | 120.9 |
N4i—Ag1—O3' | 88.5 (4) | N4—C10—C11 | 123.5 (7) |
N4i—Ag1—O3'ii | 121.5 (4) | N4—C10—H10 | 118.3 |
N1—Ag1—Ag1ii | 80.06 (13) | C11—C10—H10 | 118.3 |
N1—Ag1—O2ii | 108.1 (4) | C11—C12—H12 | 120.6 |
N1—Ag1—O3 | 85.3 (3) | C8—C12—C11 | 118.8 (6) |
N1—Ag1—O3' | 85.2 (4) | C8—C12—H12 | 120.6 |
N1—Ag1—O3'ii | 82.7 (4) | C1—C2—C3 | 119.8 (6) |
O2ii—Ag1—Ag1ii | 92.4 (3) | C1—C2—H2 | 120.1 |
O2ii—Ag1—O3 | 152.0 (4) | C3—C2—H2 | 120.1 |
O2ii—Ag1—O3' | 137.1 (5) | F1—C14—C13 | 115.2 (7) |
O3—Ag1—Ag1ii | 65.2 (3) | F3—C14—F1 | 105.0 (10) |
O3—Ag1—O3' | 16.5 (4) | F3—C14—C13 | 112.6 (8) |
O3'ii—Ag1—Ag1ii | 57.0 (4) | F2—C14—F1 | 109.2 (10) |
O3'—Ag1—Ag1ii | 48.8 (5) | F2—C14—C13 | 115.4 (9) |
O3'ii—Ag1—O2ii | 40.3 (4) | F2—C14—F3 | 97.7 (11) |
O3'ii—Ag1—O3 | 122.1 (3) | O2—C13—C14 | 125.3 (10) |
O3'ii—Ag1—O3' | 105.8 (4) | O2—C13—O3 | 122.5 (11) |
C6—O1—C7 | 102.2 (5) | O2—C13—O2' | 41.3 (14) |
C1—N1—Ag1 | 119.5 (5) | O3—C13—C14 | 111.0 (8) |
C5—N1—Ag1 | 122.7 (4) | O3'—C13—C14 | 141.6 (14) |
C5—N1—C1 | 117.7 (6) | O3'—C13—O2 | 87.4 (13) |
N1—C1—H1 | 118.8 | O3'—C13—O3 | 35.9 (9) |
N1—C1—C2 | 122.5 (6) | O3'—C13—O2' | 116.8 (18) |
C2—C1—H1 | 118.8 | O2'—C13—C14 | 101.6 (17) |
C7—N3—N2 | 104.5 (5) | O2'—C13—O3 | 139.3 (16) |
C6—N2—N3 | 106.8 (5) | C13—O2—Ag1ii | 113.4 (10) |
O1—C7—C8 | 119.6 (5) | C13—O3—Ag1 | 135.1 (8) |
N3—C7—O1 | 114.0 (6) | Ag1ii—O3'—Ag1 | 74.2 (4) |
N3—C7—C8 | 126.4 (6) | C13—O3'—Ag1 | 139.8 (13) |
O1—C6—C4 | 121.0 (5) | C13—O3'—Ag1ii | 117.3 (14) |
N2—C6—O1 | 112.4 (5) | | |
| | | |
N4—C9—C8—C7 | 178.6 (6) | C10—C11—C12—C8 | −1.5 (13) |
N4—C9—C8—C12 | −1.1 (10) | C12—C11—C10—N4 | −0.9 (14) |
N4i—Ag1—N1—C1 | −155.7 (5) | C14—C13—O2—Ag1ii | 169.7 (7) |
N4i—Ag1—N1—C5 | 26.9 (8) | C14—C13—O3—Ag1 | 154.3 (8) |
N4i—Ag1—O3—C13 | 158.8 (11) | C14—C13—O3'—Ag1 | 99 (2) |
N4i—Ag1—O3'—Ag1ii | 122.4 (3) | C14—C13—O3'—Ag1ii | −163.0 (10) |
N4i—Ag1—O3'—C13 | −124 (2) | F1—C14—C13—O2 | −45.8 (16) |
C9—N4—C10—C11 | 2.3 (11) | F1—C14—C13—O3 | 121.6 (11) |
C9—C8—C12—C11 | 2.5 (11) | F1—C14—C13—O3' | 98 (2) |
Ag1i—N4—C9—C8 | 173.7 (4) | F1—C14—C13—O2' | −83.2 (18) |
Ag1i—N4—C10—C11 | −172.7 (7) | F3—C14—C13—O2 | −166.2 (14) |
Ag1ii—Ag1—N1—C1 | 79.9 (5) | F3—C14—C13—O3 | 1.2 (13) |
Ag1ii—Ag1—N1—C5 | −97.5 (5) | F3—C14—C13—O3' | −23 (2) |
Ag1ii—Ag1—O3—C13 | 39.2 (10) | F3—C14—C13—O2' | 156.4 (18) |
Ag1ii—Ag1—O3'—C13 | 114 (2) | F2—C14—C13—O2 | 82.9 (16) |
Ag1—N1—C1—C2 | −178.6 (5) | F2—C14—C13—O3 | −109.7 (13) |
Ag1—N1—C5—C4 | 177.8 (4) | F2—C14—C13—O3' | −134 (2) |
O1—C7—C8—C9 | −6.7 (9) | F2—C14—C13—O2' | 45.5 (19) |
O1—C7—C8—C12 | 173.1 (6) | O2ii—Ag1—N1—C1 | −9.4 (6) |
O1—C6—C4—C5 | 1.5 (9) | O2ii—Ag1—N1—C5 | 173.2 (5) |
O1—C6—C4—C3 | −176.0 (5) | O2ii—Ag1—O3—C13 | 78.7 (14) |
N1—Ag1—O3—C13 | −42.0 (11) | O2ii—Ag1—O3'—Ag1ii | 30.5 (8) |
N1—Ag1—O3'—Ag1ii | −81.0 (3) | O2ii—Ag1—O3'—C13 | 144 (2) |
N1—Ag1—O3'—C13 | 33 (2) | O2—C13—O3—Ag1 | −37.9 (17) |
N1—C1—C2—C3 | 2.2 (11) | O2—C13—O3'—Ag1ii | −12.2 (13) |
N1—C5—C4—C6 | −178.2 (5) | O2—C13—O3'—Ag1 | −110 (2) |
N1—C5—C4—C3 | −0.8 (9) | O3—Ag1—N1—C1 | 145.5 (6) |
C1—N1—C5—C4 | 0.3 (9) | O3—Ag1—N1—C5 | −31.9 (5) |
N3—N2—C6—O1 | 0.6 (9) | O3—Ag1—O3'—Ag1ii | −170.9 (17) |
N3—N2—C6—C4 | −178.1 (6) | O3—Ag1—O3'—C13 | −57.1 (19) |
N3—C7—C8—C9 | 175.7 (7) | O3—C13—O2—Ag1ii | 3.7 (15) |
N3—C7—C8—C12 | −4.5 (11) | O3—C13—O3'—Ag1ii | 156 (2) |
N2—N3—C7—O1 | 0.7 (9) | O3—C13—O3'—Ag1 | 59 (2) |
N2—N3—C7—C8 | 178.4 (7) | O3'ii—Ag1—N1—C1 | 22.3 (7) |
N2—C6—C4—C5 | 180.0 (7) | O3'—Ag1—N1—C1 | 128.9 (7) |
N2—C6—C4—C3 | 2.5 (10) | O3'ii—Ag1—N1—C5 | −155.2 (6) |
C7—O1—C6—N2 | −0.2 (7) | O3'—Ag1—N1—C5 | −48.5 (6) |
C7—O1—C6—C4 | 178.6 (5) | O3'—Ag1—O3—C13 | 46.7 (14) |
C7—N3—N2—C6 | −0.8 (9) | O3'ii—Ag1—O3—C13 | 36.4 (13) |
C7—C8—C12—C11 | −177.3 (7) | O3'ii—Ag1—O3'—Ag1ii | 0.0 |
C6—O1—C7—N3 | −0.4 (8) | O3'ii—Ag1—O3'—C13 | 114 (2) |
C6—O1—C7—C8 | −178.3 (5) | O3'—C13—O2—Ag1ii | 11.5 (12) |
C6—C4—C3—C2 | 179.4 (6) | O3'—C13—O3—Ag1 | −51.3 (18) |
C5—N1—C1—C2 | −1.0 (10) | O2'—C13—O2—Ag1ii | −126 (3) |
C5—C4—C3—C2 | 1.9 (9) | O2'—C13—O3—Ag1 | 13 (3) |
C4—C3—C2—C1 | −2.6 (10) | O2'—C13—O3'—Ag1ii | 18 (2) |
C10—N4—C9—C8 | −1.2 (9) | O2'—C13—O3'—Ag1 | −80 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y, −z+1. |
5-{3-[5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole (exp_3265)
top
Crystal data top
C22H15N5O2 | F(000) = 792 |
Mr = 381.39 | Dx = 1.400 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 7.7222 (3) Å | Cell parameters from 2321 reflections |
b = 11.5401 (5) Å | θ = 8.5–70.3° |
c = 20.4160 (8) Å | µ = 0.77 mm−1 |
β = 95.965 (4)° | T = 296 K |
V = 1809.51 (13) Å3 | Needle, clear light colourless |
Z = 4 | 0.29 × 0.06 × 0.04 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 3207 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 2447 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.056 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 67.1°, θmin = 4.4° |
ω scans | h = −5→9 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −13→13 |
Tmin = 0.178, Tmax = 1.000 | l = −24→24 |
6339 measured reflections | |
Refinement top
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)] = 0.082 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.239 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1486P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3 |
3207 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
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 | |
O1 | 1.0869 (2) | 0.41554 (16) | 0.21033 (9) | 0.0500 (5) | |
O2 | 0.5872 (2) | 0.47643 (16) | −0.10943 (8) | 0.0494 (5) | |
C8 | 0.9274 (3) | 0.4315 (2) | 0.10155 (13) | 0.0468 (6) | |
C4 | 1.2278 (3) | 0.4503 (2) | 0.31995 (13) | 0.0479 (7) | |
N4 | 0.6380 (3) | 0.6356 (2) | −0.05112 (12) | 0.0606 (7) | |
N2 | 1.1123 (4) | 0.5980 (2) | 0.23992 (13) | 0.0661 (8) | |
C16 | 0.4228 (3) | 0.5498 (2) | −0.20800 (12) | 0.0454 (6) | |
C7 | 1.0108 (3) | 0.4844 (2) | 0.16136 (13) | 0.0461 (6) | |
N5 | 0.5393 (3) | 0.6645 (2) | −0.11088 (12) | 0.0612 (7) | |
C13 | 0.8382 (3) | 0.5005 (2) | 0.05366 (13) | 0.0477 (7) | |
H13 | 0.8327 | 0.5802 | 0.0599 | 0.057* | |
C15 | 0.5139 (3) | 0.5690 (2) | −0.14316 (14) | 0.0473 (6) | |
N3 | 1.0241 (3) | 0.5930 (2) | 0.17581 (12) | 0.0634 (7) | |
C6 | 1.1432 (3) | 0.4931 (2) | 0.25772 (13) | 0.0468 (6) | |
C9 | 0.9359 (4) | 0.3132 (3) | 0.09219 (14) | 0.0625 (8) | |
H9 | 0.9941 | 0.2663 | 0.1244 | 0.075* | |
C14 | 0.6617 (3) | 0.5253 (2) | −0.05257 (12) | 0.0452 (6) | |
C11 | 0.7680 (4) | 0.3331 (3) | −0.01308 (14) | 0.0632 (8) | |
H11 | 0.7153 | 0.2997 | −0.0516 | 0.076* | |
C17 | 0.3409 (4) | 0.6415 (3) | −0.24271 (14) | 0.0562 (7) | |
H17 | 0.3414 | 0.7148 | −0.2238 | 0.067* | |
C20 | 0.3358 (4) | 0.4254 (3) | −0.30020 (15) | 0.0617 (8) | |
H20 | 0.3346 | 0.3522 | −0.3192 | 0.074* | |
C21 | 0.4172 (4) | 0.4413 (3) | −0.23717 (15) | 0.0571 (7) | |
H21 | 0.4686 | 0.3785 | −0.2142 | 0.069* | |
C12 | 0.7572 (3) | 0.4515 (3) | −0.00327 (13) | 0.0482 (6) | |
C10 | 0.8573 (5) | 0.2651 (3) | 0.03455 (15) | 0.0727 (10) | |
H10 | 0.8647 | 0.1856 | 0.0279 | 0.087* | |
N1 | 1.3639 (4) | 0.4951 (3) | 0.42801 (13) | 0.0761 (8) | |
C3 | 1.2416 (4) | 0.3341 (3) | 0.33341 (15) | 0.0654 (8) | |
H3 | 1.1992 | 0.2797 | 0.3022 | 0.079* | |
C5 | 1.2931 (4) | 0.5274 (3) | 0.36864 (14) | 0.0612 (8) | |
H5 | 1.2869 | 0.6062 | 0.3592 | 0.073* | |
C2 | 1.3195 (5) | 0.2992 (3) | 0.39419 (16) | 0.0756 (10) | |
H2 | 1.3337 | 0.2208 | 0.4039 | 0.091* | |
C18 | 0.2584 (4) | 0.6241 (3) | −0.30552 (14) | 0.0587 (8) | |
H18 | 0.2033 | 0.6862 | −0.3280 | 0.070* | |
C19 | 0.2561 (4) | 0.5171 (3) | −0.33547 (14) | 0.0560 (7) | |
C22 | 0.1721 (4) | 0.5007 (4) | −0.40454 (15) | 0.0768 (10) | |
H22A | 0.0554 | 0.5303 | −0.4079 | 0.115* | |
H22B | 0.1696 | 0.4197 | −0.4153 | 0.115* | |
H22C | 0.2378 | 0.5417 | −0.4346 | 0.115* | |
C1 | 1.3749 (5) | 0.3802 (3) | 0.43925 (17) | 0.0746 (10) | |
H1 | 1.4234 | 0.3552 | 0.4804 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0458 (11) | 0.0516 (11) | 0.0487 (11) | −0.0032 (8) | −0.0131 (8) | −0.0007 (8) |
O2 | 0.0465 (11) | 0.0522 (10) | 0.0465 (10) | 0.0010 (8) | −0.0086 (8) | 0.0027 (8) |
C8 | 0.0320 (13) | 0.0602 (16) | 0.0460 (14) | −0.0039 (11) | −0.0069 (10) | 0.0008 (11) |
C4 | 0.0374 (14) | 0.0551 (15) | 0.0483 (15) | −0.0049 (11) | −0.0100 (11) | −0.0011 (12) |
N4 | 0.0604 (16) | 0.0575 (15) | 0.0583 (14) | −0.0019 (12) | −0.0199 (11) | −0.0018 (11) |
N2 | 0.0695 (18) | 0.0539 (14) | 0.0669 (16) | −0.0041 (12) | −0.0314 (13) | −0.0008 (12) |
C16 | 0.0378 (14) | 0.0484 (14) | 0.0487 (15) | 0.0001 (10) | −0.0024 (11) | 0.0046 (11) |
C7 | 0.0272 (13) | 0.0573 (16) | 0.0508 (15) | −0.0009 (10) | −0.0099 (10) | 0.0066 (11) |
N5 | 0.0655 (17) | 0.0534 (14) | 0.0594 (14) | 0.0027 (11) | −0.0186 (11) | −0.0007 (11) |
C13 | 0.0344 (14) | 0.0543 (15) | 0.0522 (15) | −0.0030 (11) | −0.0064 (11) | −0.0002 (12) |
C15 | 0.0367 (14) | 0.0529 (15) | 0.0512 (15) | 0.0015 (11) | −0.0008 (11) | 0.0064 (12) |
N3 | 0.0606 (16) | 0.0549 (14) | 0.0670 (16) | 0.0014 (11) | −0.0293 (12) | 0.0011 (11) |
C6 | 0.0369 (14) | 0.0495 (14) | 0.0513 (15) | −0.0064 (11) | −0.0078 (11) | −0.0016 (11) |
C9 | 0.067 (2) | 0.0573 (17) | 0.0569 (17) | 0.0034 (14) | −0.0218 (13) | 0.0016 (14) |
C14 | 0.0322 (13) | 0.0570 (15) | 0.0442 (14) | −0.0048 (11) | −0.0069 (10) | −0.0013 (11) |
C11 | 0.073 (2) | 0.0619 (18) | 0.0500 (16) | 0.0010 (15) | −0.0173 (13) | −0.0052 (13) |
C17 | 0.0586 (18) | 0.0513 (15) | 0.0558 (16) | 0.0051 (13) | −0.0080 (12) | 0.0039 (12) |
C20 | 0.065 (2) | 0.0594 (18) | 0.0571 (18) | 0.0002 (14) | −0.0100 (14) | −0.0062 (14) |
C21 | 0.0590 (18) | 0.0531 (16) | 0.0559 (16) | 0.0057 (13) | −0.0098 (13) | 0.0033 (13) |
C12 | 0.0360 (14) | 0.0613 (15) | 0.0452 (14) | −0.0019 (11) | −0.0055 (10) | 0.0032 (12) |
C10 | 0.093 (3) | 0.0547 (17) | 0.0630 (18) | 0.0045 (16) | −0.0260 (16) | −0.0039 (15) |
N1 | 0.080 (2) | 0.089 (2) | 0.0531 (16) | −0.0069 (15) | −0.0221 (13) | −0.0027 (14) |
C3 | 0.074 (2) | 0.0548 (17) | 0.0620 (18) | −0.0089 (14) | −0.0172 (14) | 0.0004 (14) |
C5 | 0.067 (2) | 0.0620 (17) | 0.0509 (16) | −0.0055 (15) | −0.0130 (13) | −0.0041 (13) |
C2 | 0.089 (3) | 0.066 (2) | 0.067 (2) | 0.0029 (18) | −0.0154 (17) | 0.0167 (16) |
C18 | 0.0521 (17) | 0.0611 (17) | 0.0594 (17) | 0.0058 (13) | −0.0114 (13) | 0.0113 (13) |
C19 | 0.0395 (15) | 0.0754 (19) | 0.0504 (16) | −0.0045 (13) | −0.0088 (12) | 0.0029 (14) |
C22 | 0.067 (2) | 0.104 (3) | 0.0545 (19) | −0.0105 (18) | −0.0179 (15) | 0.0014 (18) |
C1 | 0.073 (2) | 0.090 (2) | 0.0568 (18) | 0.0030 (19) | −0.0132 (15) | 0.0115 (18) |
Geometric parameters (Å, º) top
O1—C7 | 1.362 (3) | C11—H11 | 0.9300 |
O1—C6 | 1.356 (3) | C11—C12 | 1.385 (4) |
O2—C15 | 1.362 (3) | C11—C10 | 1.377 (4) |
O2—C14 | 1.363 (3) | C17—H17 | 0.9300 |
C8—C7 | 1.454 (3) | C17—C18 | 1.386 (4) |
C8—C13 | 1.387 (4) | C20—H20 | 0.9300 |
C8—C9 | 1.381 (4) | C20—C21 | 1.384 (4) |
C4—C6 | 1.453 (3) | C20—C19 | 1.387 (4) |
C4—C3 | 1.371 (4) | C21—H21 | 0.9300 |
C4—C5 | 1.389 (4) | C10—H10 | 0.9300 |
N4—N5 | 1.410 (3) | N1—C5 | 1.330 (4) |
N4—C14 | 1.287 (3) | N1—C1 | 1.347 (4) |
N2—N3 | 1.412 (3) | C3—H3 | 0.9300 |
N2—C6 | 1.280 (4) | C3—C2 | 1.382 (4) |
C16—C15 | 1.450 (4) | C5—H5 | 0.9300 |
C16—C17 | 1.389 (4) | C2—H2 | 0.9300 |
C16—C21 | 1.385 (4) | C2—C1 | 1.349 (5) |
C7—N3 | 1.289 (4) | C18—H18 | 0.9300 |
N5—C15 | 1.288 (4) | C18—C19 | 1.378 (4) |
C13—H13 | 0.9300 | C19—C22 | 1.501 (4) |
C13—C12 | 1.382 (4) | C22—H22A | 0.9600 |
C9—H9 | 0.9300 | C22—H22B | 0.9600 |
C9—C10 | 1.383 (4) | C22—H22C | 0.9600 |
C14—C12 | 1.458 (4) | C1—H1 | 0.9300 |
| | | |
C6—O1—C7 | 102.7 (2) | C18—C17—H17 | 119.9 |
C15—O2—C14 | 102.9 (2) | C21—C20—H20 | 119.5 |
C13—C8—C7 | 119.7 (3) | C21—C20—C19 | 121.1 (3) |
C9—C8—C7 | 120.5 (2) | C19—C20—H20 | 119.5 |
C9—C8—C13 | 119.8 (2) | C16—C21—H21 | 119.7 |
C3—C4—C6 | 121.7 (2) | C20—C21—C16 | 120.7 (3) |
C3—C4—C5 | 117.9 (3) | C20—C21—H21 | 119.7 |
C5—C4—C6 | 120.3 (3) | C13—C12—C14 | 119.6 (3) |
C14—N4—N5 | 106.2 (2) | C13—C12—C11 | 119.7 (3) |
C6—N2—N3 | 106.4 (2) | C11—C12—C14 | 120.6 (2) |
C17—C16—C15 | 120.1 (3) | C9—C10—H10 | 119.5 |
C21—C16—C15 | 121.4 (2) | C11—C10—C9 | 121.0 (3) |
C21—C16—C17 | 118.5 (3) | C11—C10—H10 | 119.5 |
O1—C7—C8 | 119.4 (2) | C5—N1—C1 | 116.3 (3) |
N3—C7—O1 | 112.4 (2) | C4—C3—H3 | 120.6 |
N3—C7—C8 | 128.2 (3) | C4—C3—C2 | 118.9 (3) |
C15—N5—N4 | 106.3 (2) | C2—C3—H3 | 120.6 |
C8—C13—H13 | 119.8 | C4—C5—H5 | 118.1 |
C12—C13—C8 | 120.4 (3) | N1—C5—C4 | 123.9 (3) |
C12—C13—H13 | 119.8 | N1—C5—H5 | 118.1 |
O2—C15—C16 | 118.6 (2) | C3—C2—H2 | 120.4 |
N5—C15—O2 | 112.3 (3) | C1—C2—C3 | 119.2 (3) |
N5—C15—C16 | 129.2 (3) | C1—C2—H2 | 120.4 |
C7—N3—N2 | 105.7 (2) | C17—C18—H18 | 119.2 |
O1—C6—C4 | 118.8 (2) | C19—C18—C17 | 121.6 (3) |
N2—C6—O1 | 112.7 (2) | C19—C18—H18 | 119.2 |
N2—C6—C4 | 128.6 (3) | C20—C19—C22 | 121.1 (3) |
C8—C9—H9 | 120.3 | C18—C19—C20 | 117.9 (3) |
C8—C9—C10 | 119.4 (3) | C18—C19—C22 | 120.9 (3) |
C10—C9—H9 | 120.3 | C19—C22—H22A | 109.5 |
O2—C14—C12 | 119.0 (2) | C19—C22—H22B | 109.5 |
N4—C14—O2 | 112.3 (2) | C19—C22—H22C | 109.5 |
N4—C14—C12 | 128.6 (2) | H22A—C22—H22B | 109.5 |
C12—C11—H11 | 120.2 | H22A—C22—H22C | 109.5 |
C10—C11—H11 | 120.2 | H22B—C22—H22C | 109.5 |
C10—C11—C12 | 119.6 (3) | N1—C1—C2 | 123.8 (3) |
C16—C17—H17 | 119.9 | N1—C1—H1 | 118.1 |
C18—C17—C16 | 120.2 (3) | C2—C1—H1 | 118.1 |
| | | |
O1—C7—N3—N2 | −1.4 (3) | C6—C4—C5—N1 | 176.4 (3) |
O2—C14—C12—C13 | 177.9 (2) | C6—N2—N3—C7 | 0.0 (3) |
O2—C14—C12—C11 | −1.9 (4) | C9—C8—C7—O1 | −4.7 (4) |
C8—C7—N3—N2 | 178.5 (2) | C9—C8—C7—N3 | 175.3 (3) |
C8—C13—C12—C14 | 179.0 (2) | C9—C8—C13—C12 | 0.2 (4) |
C8—C13—C12—C11 | −1.1 (4) | C14—O2—C15—C16 | 179.2 (2) |
C8—C9—C10—C11 | −1.2 (5) | C14—O2—C15—N5 | −0.2 (3) |
C4—C3—C2—C1 | 2.1 (5) | C14—N4—N5—C15 | −0.6 (3) |
N4—N5—C15—O2 | 0.5 (3) | C17—C16—C15—O2 | 177.6 (2) |
N4—N5—C15—C16 | −178.8 (2) | C17—C16—C15—N5 | −3.1 (4) |
N4—C14—C12—C13 | −0.7 (4) | C17—C16—C21—C20 | 1.7 (4) |
N4—C14—C12—C11 | 179.5 (3) | C17—C18—C19—C20 | 1.5 (4) |
C16—C17—C18—C19 | −0.6 (4) | C17—C18—C19—C22 | −177.6 (3) |
C7—O1—C6—C4 | 177.9 (2) | C21—C16—C15—O2 | −3.4 (4) |
C7—O1—C6—N2 | −2.2 (3) | C21—C16—C15—N5 | 175.9 (3) |
C7—C8—C13—C12 | −179.6 (2) | C21—C16—C17—C18 | −1.1 (4) |
C7—C8—C9—C10 | −179.3 (3) | C21—C20—C19—C18 | −0.8 (5) |
N5—N4—C14—O2 | 0.5 (3) | C21—C20—C19—C22 | 178.3 (3) |
N5—N4—C14—C12 | 179.2 (3) | C12—C11—C10—C9 | 0.2 (5) |
C13—C8—C7—O1 | 175.1 (2) | C10—C11—C12—C13 | 0.9 (4) |
C13—C8—C7—N3 | −4.9 (4) | C10—C11—C12—C14 | −179.2 (3) |
C13—C8—C9—C10 | 1.0 (4) | C3—C4—C6—O1 | −4.4 (4) |
C15—O2—C14—N4 | −0.2 (3) | C3—C4—C6—N2 | 175.7 (3) |
C15—O2—C14—C12 | −179.0 (2) | C3—C4—C5—N1 | −1.8 (5) |
C15—C16—C17—C18 | 178.0 (2) | C3—C2—C1—N1 | −2.2 (6) |
C15—C16—C21—C20 | −177.3 (2) | C5—C4—C6—O1 | 177.5 (2) |
N3—N2—C6—O1 | 1.4 (3) | C5—C4—C6—N2 | −2.4 (4) |
N3—N2—C6—C4 | −178.6 (2) | C5—C4—C3—C2 | −0.2 (5) |
C6—O1—C7—C8 | −177.8 (2) | C5—N1—C1—C2 | 0.3 (6) |
C6—O1—C7—N3 | 2.2 (3) | C19—C20—C21—C16 | −0.8 (5) |
C6—C4—C3—C2 | −178.3 (3) | C1—N1—C5—C4 | 1.8 (5) |
Bis(µ
3-5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole)tetra-µ
3-trifluoroacetato-disilver(I)
dichloromethane monosolvate (exp_3309)
top
Crystal data top
[Ag4(C2F3O2)4(C22H15N5O2)2]·CH2Cl2 | F(000) = 3384 |
Mr = 1731.26 | Dx = 1.925 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 20.3700 (6) Å | Cell parameters from 6547 reflections |
b = 15.0076 (3) Å | θ = 6.3–71.2° |
c = 19.5451 (5) Å | µ = 12.15 mm−1 |
β = 90.133 (3)° | T = 293 K |
V = 5975.0 (3) Å3 | Plate, colourless |
Z = 4 | 0.17 × 0.15 × 0.04 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 5332 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 4035 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 67.1°, θmin = 3.7° |
ω scans | h = −22→24 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −15→17 |
Tmin = 0.264, Tmax = 1.000 | l = −22→23 |
20309 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0938P)2 + 8.0456P] where P = (Fo2 + 2Fc2)/3 |
5332 reflections | (Δ/σ)max = 0.002 |
429 parameters | Δρmax = 1.02 e Å−3 |
0 restraints | Δρmin = −1.38 e Å−3 |
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) |
Ag1 | 0.31738 (3) | 0.23588 (3) | 0.31431 (3) | 0.0883 (2) | |
Ag2 | 0.28858 (3) | 0.32296 (3) | 0.46872 (3) | 0.0755 (2) | |
C1 | 0.1836 (4) | 0.4163 (4) | 0.7937 (3) | 0.0735 (17) | |
H1 | 0.1673 | 0.3718 | 0.8221 | 0.088* | |
C2 | 0.1912 (4) | 0.5005 (4) | 0.8197 (3) | 0.0717 (16) | |
H2 | 0.1819 | 0.5122 | 0.8653 | 0.086* | |
C3 | 0.2128 (3) | 0.5670 (4) | 0.7776 (3) | 0.0648 (14) | |
H3 | 0.2159 | 0.6253 | 0.7935 | 0.078* | |
C4 | 0.2300 (3) | 0.5464 (3) | 0.7109 (3) | 0.0526 (12) | |
C5 | 0.2218 (3) | 0.4601 (3) | 0.6884 (3) | 0.0595 (14) | |
H5 | 0.2328 | 0.4463 | 0.6435 | 0.071* | |
C6 | 0.2557 (3) | 0.6136 (3) | 0.6648 (3) | 0.0503 (11) | |
C7 | 0.2986 (3) | 0.6652 (3) | 0.5741 (3) | 0.0543 (12) | |
C8 | 0.3252 (3) | 0.6634 (3) | 0.5058 (3) | 0.0523 (12) | |
C9 | 0.3289 (3) | 0.5845 (3) | 0.4688 (3) | 0.0546 (12) | |
H9 | 0.3125 | 0.5319 | 0.4873 | 0.066* | |
C10 | 0.3568 (3) | 0.5845 (3) | 0.4044 (3) | 0.0531 (12) | |
C11 | 0.3813 (3) | 0.6629 (4) | 0.3766 (3) | 0.0657 (15) | |
H11 | 0.4009 | 0.6624 | 0.3337 | 0.079* | |
C12 | 0.3764 (4) | 0.7416 (4) | 0.4130 (3) | 0.0702 (16) | |
H12 | 0.3915 | 0.7945 | 0.3938 | 0.084* | |
C13 | 0.3494 (3) | 0.7422 (4) | 0.4776 (3) | 0.0650 (15) | |
H13 | 0.3472 | 0.7951 | 0.5023 | 0.078* | |
C14 | 0.3628 (3) | 0.5006 (3) | 0.3663 (3) | 0.0523 (12) | |
C15 | 0.3904 (3) | 0.4186 (3) | 0.2818 (3) | 0.0512 (11) | |
C16 | 0.4193 (3) | 0.3967 (4) | 0.2161 (3) | 0.0557 (12) | |
C17 | 0.4354 (3) | 0.3098 (4) | 0.2000 (3) | 0.0659 (15) | |
H17 | 0.4255 | 0.2641 | 0.2304 | 0.079* | |
C18 | 0.4665 (3) | 0.2903 (5) | 0.1384 (3) | 0.0730 (16) | |
H18 | 0.4771 | 0.2316 | 0.1280 | 0.088* | |
C19 | 0.4820 (3) | 0.3578 (5) | 0.0919 (3) | 0.0731 (17) | |
C20 | 0.4639 (4) | 0.4427 (5) | 0.1086 (3) | 0.086 (2) | |
H20 | 0.4721 | 0.4882 | 0.0775 | 0.103* | |
C21 | 0.4338 (4) | 0.4635 (5) | 0.1699 (3) | 0.0790 (19) | |
H21 | 0.4234 | 0.5224 | 0.1801 | 0.095* | |
C22 | 0.5161 (4) | 0.3366 (7) | 0.0265 (4) | 0.105 (3) | |
H22A | 0.4845 | 0.3173 | −0.0068 | 0.157* | |
H22B | 0.5476 | 0.2900 | 0.0343 | 0.157* | |
H22C | 0.5382 | 0.3888 | 0.0101 | 0.157* | |
C23 | 0.1002 (5) | 0.2335 (6) | 0.3442 (5) | 0.103 (3) | |
C24 | 0.1607 (4) | 0.2096 (4) | 0.3833 (4) | 0.0742 (17) | |
C25 | 0.1564 (4) | 0.3841 (5) | 0.5237 (4) | 0.0778 (18) | |
C26 | 0.0966 (6) | 0.4461 (6) | 0.5281 (6) | 0.113 (3) | |
C27 | 0.492 (2) | 0.9874 (19) | 0.2155 (17) | 0.208 (19) | 0.50 |
H27A | 0.4633 | 0.9869 | 0.1765 | 0.250* | 0.50 |
H27B | 0.5342 | 0.9641 | 0.2028 | 0.250* | 0.50 |
Cl1 | 0.4597 (6) | 0.9270 (7) | 0.2879 (7) | 0.237 (5) | 0.50 |
Cl2 | 0.5000 | 1.0900 (4) | 0.2500 | 0.248 (4) | |
F1 | 0.1098 (5) | 0.5145 (6) | 0.5652 (7) | 0.240 (5) | |
F2 | 0.0461 (4) | 0.4155 (6) | 0.5494 (8) | 0.256 (7) | |
F3 | 0.0826 (5) | 0.4838 (9) | 0.4730 (5) | 0.254 (6) | |
F4 | 0.0783 (5) | 0.3130 (6) | 0.3635 (7) | 0.243 (6) | |
F5 | 0.0513 (4) | 0.1835 (5) | 0.3474 (5) | 0.173 (3) | |
F6 | 0.1107 (5) | 0.2523 (9) | 0.2818 (4) | 0.227 (5) | |
N1 | 0.3618 (2) | 0.3676 (3) | 0.3261 (2) | 0.0531 (10) | |
N2 | 0.3449 (2) | 0.4213 (3) | 0.3818 (2) | 0.0549 (10) | |
N3 | 0.2959 (3) | 0.7306 (3) | 0.6164 (3) | 0.0643 (12) | |
N4 | 0.2681 (3) | 0.6966 (3) | 0.6769 (3) | 0.0636 (12) | |
N6 | 0.1987 (3) | 0.3956 (3) | 0.7288 (3) | 0.0693 (14) | |
O1 | 0.39189 (19) | 0.5039 (2) | 0.30364 (17) | 0.0555 (9) | |
O2 | 0.27373 (18) | 0.5888 (2) | 0.60118 (17) | 0.0529 (8) | |
O3 | 0.2097 (3) | 0.2570 (4) | 0.3737 (3) | 0.0918 (15) | |
O4 | 0.2010 (3) | 0.4150 (4) | 0.4898 (3) | 0.1042 (17) | |
O5 | 0.1528 (3) | 0.1487 (4) | 0.4251 (3) | 0.1084 (18) | |
O6 | 0.1497 (3) | 0.3123 (3) | 0.5521 (3) | 0.0916 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.1187 (5) | 0.0412 (3) | 0.1051 (4) | −0.0113 (2) | 0.0456 (3) | −0.0104 (2) |
Ag2 | 0.0806 (4) | 0.0745 (3) | 0.0715 (3) | 0.0062 (2) | 0.0202 (2) | 0.0148 (2) |
C1 | 0.105 (5) | 0.058 (3) | 0.057 (3) | 0.001 (3) | 0.017 (3) | 0.006 (3) |
C2 | 0.091 (5) | 0.073 (4) | 0.051 (3) | −0.006 (3) | 0.007 (3) | −0.007 (3) |
C3 | 0.075 (4) | 0.058 (3) | 0.062 (3) | −0.005 (3) | 0.012 (3) | −0.017 (3) |
C4 | 0.058 (3) | 0.044 (3) | 0.056 (3) | 0.002 (2) | 0.004 (2) | −0.006 (2) |
C5 | 0.084 (4) | 0.044 (3) | 0.051 (3) | −0.001 (2) | 0.008 (3) | −0.003 (2) |
C6 | 0.054 (3) | 0.048 (3) | 0.049 (3) | −0.001 (2) | 0.005 (2) | −0.011 (2) |
C7 | 0.054 (3) | 0.043 (3) | 0.066 (3) | −0.003 (2) | 0.000 (3) | −0.004 (2) |
C8 | 0.055 (3) | 0.045 (3) | 0.057 (3) | 0.000 (2) | 0.001 (2) | −0.001 (2) |
C9 | 0.062 (3) | 0.044 (3) | 0.058 (3) | −0.009 (2) | 0.004 (2) | 0.005 (2) |
C10 | 0.060 (3) | 0.046 (3) | 0.054 (3) | −0.007 (2) | 0.004 (2) | −0.001 (2) |
C11 | 0.088 (4) | 0.055 (3) | 0.055 (3) | −0.011 (3) | 0.005 (3) | 0.008 (2) |
C12 | 0.093 (5) | 0.044 (3) | 0.073 (4) | −0.018 (3) | 0.009 (3) | 0.006 (3) |
C13 | 0.076 (4) | 0.045 (3) | 0.074 (4) | −0.007 (2) | 0.000 (3) | −0.002 (2) |
C14 | 0.059 (3) | 0.050 (3) | 0.048 (3) | −0.005 (2) | 0.006 (2) | 0.003 (2) |
C15 | 0.057 (3) | 0.048 (3) | 0.049 (3) | −0.001 (2) | 0.006 (2) | 0.004 (2) |
C16 | 0.059 (3) | 0.059 (3) | 0.049 (3) | 0.001 (2) | 0.008 (2) | 0.001 (2) |
C17 | 0.070 (4) | 0.064 (3) | 0.064 (4) | 0.002 (3) | 0.012 (3) | 0.001 (3) |
C18 | 0.068 (4) | 0.086 (4) | 0.065 (4) | 0.010 (3) | 0.012 (3) | −0.015 (3) |
C19 | 0.061 (4) | 0.103 (5) | 0.055 (3) | −0.001 (3) | 0.006 (3) | −0.006 (3) |
C20 | 0.100 (5) | 0.098 (5) | 0.061 (4) | −0.001 (4) | 0.027 (4) | 0.014 (3) |
C21 | 0.103 (5) | 0.071 (4) | 0.064 (4) | −0.005 (3) | 0.030 (4) | 0.007 (3) |
C22 | 0.087 (6) | 0.154 (8) | 0.073 (5) | −0.002 (5) | 0.026 (4) | −0.019 (5) |
C23 | 0.135 (8) | 0.079 (5) | 0.093 (6) | −0.023 (5) | 0.000 (5) | 0.002 (4) |
C24 | 0.084 (5) | 0.065 (3) | 0.074 (4) | 0.004 (3) | 0.024 (4) | 0.014 (3) |
C25 | 0.083 (5) | 0.075 (4) | 0.076 (4) | 0.024 (3) | 0.009 (4) | 0.004 (3) |
C26 | 0.122 (8) | 0.086 (6) | 0.131 (8) | 0.044 (5) | 0.042 (6) | 0.021 (5) |
C27 | 0.22 (3) | 0.14 (2) | 0.26 (5) | 0.06 (2) | 0.07 (4) | −0.04 (2) |
Cl1 | 0.237 (11) | 0.199 (9) | 0.275 (13) | −0.026 (8) | −0.002 (8) | 0.069 (9) |
Cl2 | 0.256 (8) | 0.112 (4) | 0.377 (12) | 0.000 | −0.052 (8) | 0.000 |
F1 | 0.215 (9) | 0.156 (7) | 0.349 (15) | 0.080 (7) | −0.003 (9) | −0.114 (9) |
F2 | 0.125 (6) | 0.156 (7) | 0.487 (19) | 0.063 (5) | 0.135 (9) | 0.084 (9) |
F3 | 0.221 (10) | 0.333 (14) | 0.210 (9) | 0.186 (10) | 0.033 (7) | 0.097 (10) |
F4 | 0.219 (10) | 0.129 (6) | 0.380 (16) | 0.068 (6) | −0.119 (10) | −0.029 (7) |
F5 | 0.117 (5) | 0.134 (5) | 0.269 (10) | −0.029 (4) | −0.052 (6) | 0.028 (5) |
F6 | 0.200 (9) | 0.399 (16) | 0.082 (4) | −0.014 (9) | −0.016 (5) | 0.009 (7) |
N1 | 0.062 (3) | 0.044 (2) | 0.054 (2) | −0.0004 (18) | 0.014 (2) | 0.0006 (17) |
N2 | 0.065 (3) | 0.049 (2) | 0.051 (2) | −0.0036 (18) | 0.013 (2) | 0.0009 (18) |
N3 | 0.078 (3) | 0.048 (2) | 0.067 (3) | −0.008 (2) | 0.011 (3) | −0.010 (2) |
N4 | 0.080 (3) | 0.044 (2) | 0.067 (3) | −0.007 (2) | 0.016 (2) | −0.010 (2) |
N6 | 0.104 (4) | 0.040 (2) | 0.065 (3) | 0.003 (2) | 0.016 (3) | 0.004 (2) |
O1 | 0.069 (2) | 0.0487 (18) | 0.0485 (19) | −0.0105 (15) | 0.0127 (17) | 0.0020 (14) |
O2 | 0.067 (2) | 0.0395 (16) | 0.0522 (19) | −0.0040 (14) | 0.0056 (16) | −0.0080 (14) |
O3 | 0.086 (4) | 0.093 (3) | 0.096 (4) | −0.006 (3) | 0.017 (3) | 0.023 (3) |
O4 | 0.094 (4) | 0.093 (4) | 0.126 (5) | 0.011 (3) | 0.024 (3) | 0.027 (3) |
O5 | 0.124 (5) | 0.101 (4) | 0.101 (4) | −0.016 (3) | 0.009 (3) | 0.036 (3) |
O6 | 0.101 (4) | 0.085 (3) | 0.088 (3) | 0.028 (3) | 0.012 (3) | 0.020 (3) |
Geometric parameters (Å, º) top
Ag1—Ag2 | 3.3419 (7) | C15—O1 | 1.351 (6) |
Ag1—N1 | 2.186 (4) | C16—C17 | 1.382 (8) |
Ag1—N6i | 2.170 (5) | C16—C21 | 1.383 (8) |
Ag1—O3 | 2.504 (5) | C17—H17 | 0.9300 |
Ag2—Ag2i | 2.9615 (9) | C17—C18 | 1.392 (8) |
Ag2—N2 | 2.528 (4) | C18—H18 | 0.9300 |
Ag2—O4 | 2.295 (6) | C18—C19 | 1.397 (10) |
Ag2—O5i | 2.430 (6) | C19—C20 | 1.366 (10) |
Ag2—O6i | 2.423 (5) | C19—C22 | 1.490 (9) |
Ag2—O3 | 2.646 (2) | C20—H20 | 0.9300 |
C1—H1 | 0.9300 | C20—C21 | 1.384 (9) |
C1—C2 | 1.370 (9) | C21—H21 | 0.9300 |
C1—N6 | 1.343 (8) | C22—H22A | 0.9600 |
C2—H2 | 0.9300 | C22—H22B | 0.9600 |
C2—C3 | 1.367 (9) | C22—H22C | 0.9600 |
C3—H3 | 0.9300 | C23—C24 | 1.493 (13) |
C3—C4 | 1.386 (8) | C23—F4 | 1.329 (12) |
C4—C5 | 1.377 (7) | C23—F5 | 1.248 (11) |
C4—C6 | 1.450 (7) | C23—F6 | 1.269 (11) |
C5—H5 | 0.9300 | C24—O3 | 1.241 (8) |
C5—N6 | 1.335 (7) | C24—O5 | 1.235 (8) |
C6—N4 | 1.293 (6) | C25—C26 | 1.536 (10) |
C6—O2 | 1.349 (6) | C25—O4 | 1.218 (9) |
C7—C8 | 1.443 (8) | C25—O6 | 1.220 (8) |
C7—N3 | 1.284 (7) | C26—F1 | 1.285 (14) |
C7—O2 | 1.361 (6) | C26—F2 | 1.202 (12) |
C8—C9 | 1.389 (7) | C26—F3 | 1.248 (12) |
C8—C13 | 1.395 (7) | C27—C27ii | 1.39 (7) |
C9—H9 | 0.9300 | C27—H27A | 0.9596 |
C9—C10 | 1.383 (7) | C27—H27B | 0.9596 |
C10—C11 | 1.389 (7) | C27—Cl1 | 1.81 (3) |
C10—C14 | 1.468 (7) | C27—Cl1ii | 1.34 (3) |
C11—H11 | 0.9300 | C27—Cl2 | 1.69 (3) |
C11—C12 | 1.384 (8) | Cl1—C27ii | 1.34 (3) |
C12—H12 | 0.9300 | Cl1—Cl1ii | 2.21 (3) |
C12—C13 | 1.378 (9) | Cl2—C27ii | 1.69 (3) |
C13—H13 | 0.9300 | N1—N2 | 1.397 (6) |
C14—N2 | 1.281 (6) | N3—N4 | 1.407 (7) |
C14—O1 | 1.363 (6) | N6—Ag1i | 2.170 (5) |
C15—C16 | 1.451 (7) | O5—Ag2i | 2.430 (6) |
C15—N1 | 1.296 (6) | O6—Ag2i | 2.422 (5) |
| | | |
N1—Ag1—Ag2 | 67.93 (11) | C17—C18—H18 | 119.5 |
N1—Ag1—O3 | 101.49 (17) | C17—C18—C19 | 120.9 (6) |
N6i—Ag1—Ag2 | 132.79 (13) | C19—C18—H18 | 119.5 |
N6i—Ag1—N1 | 157.74 (18) | C18—C19—C22 | 120.6 (7) |
N6i—Ag1—O3 | 99.4 (2) | C20—C19—C18 | 117.4 (6) |
O3—Ag1—Ag2 | 51.41 (13) | C20—C19—C22 | 122.0 (7) |
Ag2i—Ag2—Ag1 | 100.26 (3) | C19—C20—H20 | 118.7 |
N2—Ag2—Ag1 | 62.62 (10) | C19—C20—C21 | 122.5 (7) |
N2—Ag2—Ag2i | 162.04 (10) | C21—C20—H20 | 118.7 |
O4—Ag2—Ag1 | 122.37 (17) | C16—C21—C20 | 119.9 (7) |
O4—Ag2—Ag2i | 87.57 (14) | C16—C21—H21 | 120.1 |
O4—Ag2—N2 | 97.09 (17) | C20—C21—H21 | 120.1 |
O4—Ag2—O5i | 97.0 (2) | C19—C22—H22A | 109.5 |
O4—Ag2—O6i | 159.8 (2) | C19—C22—H22B | 109.5 |
O5i—Ag2—Ag1 | 138.86 (16) | C19—C22—H22C | 109.5 |
O5i—Ag2—Ag2i | 92.11 (13) | H22A—C22—H22B | 109.5 |
O5i—Ag2—N2 | 104.44 (17) | H22A—C22—H22C | 109.5 |
O6i—Ag2—Ag1 | 55.13 (13) | H22B—C22—H22C | 109.5 |
O6i—Ag2—Ag2i | 74.07 (14) | F4—C23—C24 | 110.3 (8) |
O6i—Ag2—N2 | 98.03 (16) | F5—C23—C24 | 119.1 (8) |
O6i—Ag2—O5i | 92.1 (2) | F5—C23—F4 | 104.9 (11) |
C2—C1—H1 | 118.8 | F5—C23—F6 | 108.6 (10) |
N6—C1—H1 | 118.8 | F6—C23—C24 | 113.9 (10) |
N6—C1—C2 | 122.4 (6) | F6—C23—F4 | 97.5 (10) |
C1—C2—H2 | 120.4 | O3—C24—C23 | 116.6 (6) |
C3—C2—C1 | 119.2 (5) | O5—C24—C23 | 114.1 (7) |
C3—C2—H2 | 120.4 | O5—C24—O3 | 129.1 (8) |
C2—C3—H3 | 120.5 | O4—C25—C26 | 113.1 (7) |
C2—C3—C4 | 119.0 (5) | O4—C25—O6 | 132.0 (7) |
C4—C3—H3 | 120.5 | O6—C25—C26 | 114.9 (7) |
C3—C4—C6 | 121.4 (5) | F1—C26—C25 | 110.5 (10) |
C5—C4—C3 | 118.7 (5) | F2—C26—C25 | 117.9 (8) |
C5—C4—C6 | 119.9 (5) | F2—C26—F1 | 106.7 (11) |
C4—C5—H5 | 118.8 | F2—C26—F3 | 106.2 (13) |
N6—C5—C4 | 122.4 (5) | F3—C26—C25 | 114.0 (8) |
N6—C5—H5 | 118.8 | F3—C26—F1 | 99.9 (11) |
N4—C6—C4 | 128.9 (5) | C27ii—C27—H27A | 155.9 |
N4—C6—O2 | 112.3 (4) | C27ii—C27—H27B | 92.6 |
O2—C6—C4 | 118.7 (4) | C27ii—C27—Cl1 | 47.4 (17) |
N3—C7—C8 | 128.8 (5) | C27ii—C27—Cl2 | 65.8 (12) |
N3—C7—O2 | 112.1 (5) | H27A—C27—H27B | 109.6 |
O2—C7—C8 | 119.0 (4) | Cl1ii—C27—C27ii | 83 (3) |
C9—C8—C7 | 121.2 (5) | Cl1—C27—H27A | 113.2 |
C9—C8—C13 | 119.8 (5) | Cl1ii—C27—H27A | 113.7 |
C13—C8—C7 | 118.9 (5) | Cl1ii—C27—H27B | 23.7 |
C8—C9—H9 | 120.1 | Cl1—C27—H27B | 110.5 |
C10—C9—C8 | 119.7 (5) | Cl1ii—C27—Cl1 | 88 (2) |
C10—C9—H9 | 120.1 | Cl1ii—C27—Cl2 | 125 (3) |
C9—C10—C11 | 120.3 (5) | Cl2—C27—H27A | 112.4 |
C9—C10—C14 | 119.8 (4) | Cl2—C27—H27B | 110.5 |
C11—C10—C14 | 119.8 (5) | Cl2—C27—Cl1 | 100.4 (15) |
C10—C11—H11 | 120.1 | C27ii—Cl1—C27 | 50 (3) |
C12—C11—C10 | 119.7 (6) | C27—Cl1—Cl1ii | 37.2 (11) |
C12—C11—H11 | 120.1 | C27ii—Cl1—Cl1ii | 54.6 (16) |
C11—C12—H12 | 119.8 | C27—Cl2—C27ii | 48 (2) |
C13—C12—C11 | 120.4 (5) | C15—N1—Ag1 | 130.5 (4) |
C13—C12—H12 | 119.8 | C15—N1—N2 | 107.0 (4) |
C8—C13—H13 | 120.0 | N2—N1—Ag1 | 120.1 (3) |
C12—C13—C8 | 119.9 (5) | C14—N2—Ag2 | 146.2 (4) |
C12—C13—H13 | 120.0 | C14—N2—N1 | 106.4 (4) |
N2—C14—C10 | 130.8 (5) | N1—N2—Ag2 | 107.4 (3) |
N2—C14—O1 | 111.8 (4) | C7—N3—N4 | 106.4 (4) |
O1—C14—C10 | 117.5 (4) | C6—N4—N3 | 106.0 (4) |
N1—C15—C16 | 129.9 (5) | C1—N6—Ag1i | 122.8 (4) |
N1—C15—O1 | 111.0 (4) | C5—N6—Ag1i | 118.9 (4) |
O1—C15—C16 | 119.0 (4) | C5—N6—C1 | 118.3 (5) |
C17—C16—C15 | 120.9 (5) | C15—O1—C14 | 103.9 (4) |
C17—C16—C21 | 119.0 (5) | C6—O2—C7 | 103.2 (4) |
C21—C16—C15 | 120.1 (5) | C24—O3—Ag1 | 134.7 (5) |
C16—C17—H17 | 119.8 | C25—O4—Ag2 | 116.7 (5) |
C16—C17—C18 | 120.3 (6) | C24—O5—Ag2i | 111.7 (5) |
C18—C17—H17 | 119.8 | C25—O6—Ag2i | 127.2 (5) |
| | | |
Ag1—Ag2—N2—C14 | 166.8 (8) | Cl1ii—C27—Cl2—C27ii | −62 (3) |
Ag1—Ag2—N2—N1 | −9.9 (3) | Cl2—C27—Cl1—C27ii | −42.7 (16) |
Ag1—Ag2—O4—C25 | 108.1 (6) | Cl2—C27—Cl1—Cl1ii | −125 (3) |
Ag1—N1—N2—Ag2 | 15.6 (4) | F4—C23—C24—O3 | −64.8 (12) |
Ag1—N1—N2—C14 | −162.5 (4) | F4—C23—C24—O5 | 109.8 (10) |
Ag2—Ag1—N1—C15 | −172.1 (5) | F5—C23—C24—O3 | 173.9 (9) |
Ag2—Ag1—N1—N2 | −12.1 (3) | F5—C23—C24—O5 | −11.5 (13) |
Ag2—Ag1—O3—C24 | −133.6 (7) | F6—C23—C24—O3 | 43.6 (12) |
Ag2i—Ag2—N2—C14 | 148.1 (6) | F6—C23—C24—O5 | −141.7 (10) |
Ag2i—Ag2—N2—N1 | −28.6 (6) | N1—Ag1—Ag2—Ag2i | −179.31 (13) |
Ag2i—Ag2—O4—C25 | 7.5 (6) | N1—Ag1—Ag2—N2 | 6.46 (18) |
C1—C2—C3—C4 | −3.8 (10) | N1—Ag1—Ag2—O4 | 87.0 (2) |
C2—C1—N6—Ag1i | −177.1 (5) | N1—Ag1—Ag2—O5i | −74.0 (2) |
C2—C1—N6—C5 | −0.2 (11) | N1—Ag1—Ag2—O6i | −117.1 (2) |
C2—C3—C4—C5 | 3.0 (9) | N1—Ag1—O3—C24 | 177.2 (7) |
C2—C3—C4—C6 | −177.5 (6) | N1—C15—C16—C17 | −17.9 (10) |
C3—C4—C5—N6 | −0.8 (9) | N1—C15—C16—C21 | 165.1 (6) |
C3—C4—C6—N4 | 2.4 (9) | N1—C15—O1—C14 | 1.2 (6) |
C3—C4—C6—O2 | 177.7 (5) | N2—Ag2—O4—C25 | 170.1 (6) |
C4—C5—N6—Ag1i | 176.4 (5) | N2—C14—O1—C15 | −0.1 (6) |
C4—C5—N6—C1 | −0.6 (10) | N3—C7—C8—C9 | 174.8 (6) |
C4—C6—N4—N3 | 176.4 (5) | N3—C7—C8—C13 | −3.3 (9) |
C4—C6—O2—C7 | −176.4 (5) | N3—C7—O2—C6 | −0.3 (6) |
C5—C4—C6—N4 | −178.2 (6) | N4—C6—O2—C7 | −0.3 (6) |
C5—C4—C6—O2 | −2.8 (8) | N6i—Ag1—Ag2—Ag2i | −9.1 (2) |
C6—C4—C5—N6 | 179.7 (6) | N6i—Ag1—Ag2—N2 | 176.7 (2) |
C7—C8—C9—C10 | −177.6 (5) | N6i—Ag1—Ag2—O4 | −102.7 (3) |
C7—C8—C13—C12 | 178.4 (6) | N6i—Ag1—Ag2—O5i | 96.2 (3) |
C7—N3—N4—C6 | −1.0 (6) | N6i—Ag1—Ag2—O6i | 53.2 (3) |
C8—C7—N3—N4 | −177.4 (6) | N6i—Ag1—N1—C15 | 27.1 (8) |
C8—C7—O2—C6 | 178.1 (5) | N6i—Ag1—N1—N2 | −172.9 (5) |
C8—C9—C10—C11 | 0.0 (9) | N6i—Ag1—O3—C24 | 4.9 (7) |
C8—C9—C10—C14 | 177.9 (5) | N6—C1—C2—C3 | 2.4 (11) |
C9—C8—C13—C12 | 0.3 (9) | O1—C14—N2—Ag2 | −177.6 (5) |
C9—C10—C11—C12 | −1.3 (10) | O1—C14—N2—N1 | −1.0 (6) |
C9—C10—C14—N2 | 1.2 (9) | O1—C15—C16—C17 | 161.9 (5) |
C9—C10—C14—O1 | −178.7 (5) | O1—C15—C16—C21 | −15.1 (8) |
C10—C11—C12—C13 | 2.1 (11) | O1—C15—N1—Ag1 | 160.1 (3) |
C10—C14—N2—Ag2 | 2.5 (12) | O1—C15—N1—N2 | −1.9 (6) |
C10—C14—N2—N1 | 179.1 (6) | O2—C6—N4—N3 | 0.8 (6) |
C10—C14—O1—C15 | 179.8 (5) | O2—C7—C8—C9 | −3.3 (8) |
C11—C10—C14—N2 | 179.0 (6) | O2—C7—C8—C13 | 178.6 (5) |
C11—C10—C14—O1 | −0.9 (8) | O2—C7—N3—N4 | 0.8 (6) |
C11—C12—C13—C8 | −1.6 (10) | O3—Ag1—Ag2—Ag2i | 53.94 (15) |
C13—C8—C9—C10 | 0.5 (9) | O3—Ag1—Ag2—N2 | −120.29 (19) |
C14—C10—C11—C12 | −179.1 (6) | O3—Ag1—Ag2—O4 | −39.7 (2) |
C15—C16—C17—C18 | −176.4 (6) | O3—Ag1—Ag2—O5i | 159.3 (2) |
C15—C16—C21—C20 | 177.3 (7) | O3—Ag1—Ag2—O6i | 116.2 (2) |
C15—N1—N2—Ag2 | 179.8 (3) | O3—Ag1—N1—C15 | −132.3 (5) |
C15—N1—N2—C14 | 1.7 (6) | O3—Ag1—N1—N2 | 27.6 (4) |
C16—C15—N1—Ag1 | −20.1 (9) | O3—C24—O5—Ag2i | 34.0 (10) |
C16—C15—N1—N2 | 177.9 (5) | O4—Ag2—N2—C14 | 43.9 (7) |
C16—C15—O1—C14 | −178.6 (5) | O4—Ag2—N2—N1 | −132.8 (3) |
C16—C17—C18—C19 | 0.1 (10) | O4—C25—C26—F1 | −70.3 (12) |
C17—C16—C21—C20 | 0.3 (11) | O4—C25—C26—F2 | 166.6 (13) |
C17—C18—C19—C20 | −1.7 (10) | O4—C25—C26—F3 | 41.2 (15) |
C17—C18—C19—C22 | 179.1 (7) | O4—C25—O6—Ag2i | −17.5 (14) |
C18—C19—C20—C21 | 2.6 (12) | O5i—Ag2—N2—C14 | −55.3 (7) |
C19—C20—C21—C16 | −1.9 (12) | O5i—Ag2—N2—N1 | 128.1 (3) |
C21—C16—C17—C18 | 0.6 (10) | O5i—Ag2—O4—C25 | −84.3 (6) |
C22—C19—C20—C21 | −178.1 (8) | O5—C24—O3—Ag1 | 77.9 (11) |
C23—C24—O3—Ag1 | −108.5 (7) | O6i—Ag2—N2—C14 | −149.6 (7) |
C23—C24—O5—Ag2i | −139.8 (6) | O6i—Ag2—N2—N1 | 33.8 (4) |
C26—C25—O4—Ag2 | −173.2 (6) | O6i—Ag2—O4—C25 | 31.9 (10) |
C26—C25—O6—Ag2i | 159.1 (6) | O6—C25—C26—F1 | 112.5 (11) |
C27ii—C27—Cl1—Cl1ii | −82 (4) | O6—C25—C26—F2 | −10.6 (17) |
Cl1ii—C27—Cl1—C27ii | 82 (4) | O6—C25—C26—F3 | −136.0 (12) |
Cl1—C27—Cl2—C27ii | 33.2 (19) | O6—C25—O4—Ag2 | 3.4 (13) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1, y, −z+1/2. |
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