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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 [Ag22-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 [Ag23-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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619011744/yf3187sup1.cif
Contains datablocks global, exp_3265, exp_3309, exp_3343

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011744/yf3187exp_3343sup2.hkl
Contains datablock exp_3343

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011744/yf3187exp_3265sup3.hkl
Contains datablock exp_3265

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619011744/yf3187exp_3309sup4.hkl
Contains datablock exp_3309

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619011744/yf3187sup5.pdf
Additional figure

CCDC references: 1949312; 1949311; 1949310

Computing details top

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 = 890.23F(000) = 436
Triclinic, P1Dx = 2.006 Mg m3
a = 7.4159 (12) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.5352 (18) ÅCell parameters from 2345 reflections
c = 11.158 (2) Åθ = 9.8–70.8°
α = 78.970 (16)°µ = 11.55 mm1
β = 82.579 (14)°T = 293 K
γ = 72.591 (16)°Block, colourless
V = 736.8 (2) Å30.16 × 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 Source2460 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.038
Detector resolution: 16.0793 pixels mm-1θmax = 67.1°, θmin = 4.1°
ω scansh = 78
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.163, Tmax = 1.000l = 1311
4467 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H 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 reflectionsΔρmax = 1.57 e Å3
246 parametersΔρmin = 1.33 e Å3
26 restraintsExtinction correction: SHELXL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/UeqOcc. (<1)
N40.0250 (7)0.8101 (6)0.7640 (5)0.0416 (11)
C110.0595 (14)0.8031 (9)0.9639 (7)0.065 (2)
H110.05370.85251.02920.078*
C90.0676 (8)0.6670 (6)0.7695 (5)0.0384 (12)
H90.07020.62040.70300.046*
Ag10.14795 (6)0.05571 (5)0.40773 (3)0.0477 (3)
O10.2419 (6)0.3549 (5)0.7856 (4)0.0384 (9)
N10.2907 (7)0.0137 (6)0.5811 (5)0.0394 (11)
C10.3863 (9)0.1263 (7)0.6270 (6)0.0436 (13)
H10.39350.20290.58440.052*
N30.3568 (11)0.3429 (7)0.9618 (6)0.0629 (17)
N20.4162 (11)0.1994 (6)0.9255 (5)0.0589 (16)
C70.2582 (9)0.4268 (7)0.8766 (5)0.0408 (13)
C60.3448 (8)0.2133 (7)0.8239 (5)0.0405 (12)
C50.2798 (8)0.1211 (6)0.6445 (5)0.0371 (11)
H50.21360.21820.61390.045*
C40.3625 (8)0.0949 (7)0.7537 (5)0.0378 (12)
C80.1608 (9)0.5847 (7)0.8713 (6)0.0409 (12)
C30.4586 (9)0.0486 (7)0.8003 (6)0.0476 (14)
H30.51260.07020.87480.057*
C100.0302 (11)0.8750 (8)0.8617 (7)0.0537 (16)
H100.09900.97460.85900.064*
C120.1599 (12)0.6544 (8)0.9690 (6)0.0550 (17)
H120.22550.60251.03700.066*
C20.4728 (9)0.1600 (7)0.7332 (6)0.0474 (14)
H20.54130.25750.76070.057*
C140.2676 (10)0.4350 (9)0.6354 (7)0.0552 (16)
F10.4475 (11)0.4851 (9)0.6613 (13)0.160 (5)
C130.2026 (10)0.2810 (9)0.6161 (9)0.065 (2)
F30.2298 (19)0.5245 (10)0.5420 (12)0.186 (5)
F20.1809 (19)0.4675 (15)0.7096 (14)0.201 (6)
O20.250 (2)0.1776 (14)0.6816 (13)0.084 (5)0.54 (2)
O30.1179 (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
U11U22U33U12U13U23
N40.056 (3)0.037 (3)0.034 (3)0.012 (2)0.013 (2)0.007 (2)
C110.104 (6)0.053 (4)0.045 (4)0.015 (4)0.026 (4)0.020 (3)
C90.052 (3)0.040 (3)0.026 (3)0.012 (2)0.012 (2)0.009 (2)
Ag10.0614 (4)0.0467 (4)0.0317 (4)0.0055 (2)0.0176 (2)0.0050 (2)
O10.051 (2)0.035 (2)0.030 (2)0.0071 (17)0.0160 (16)0.0047 (16)
N10.043 (2)0.042 (3)0.032 (2)0.005 (2)0.0156 (19)0.006 (2)
C10.051 (3)0.037 (3)0.041 (3)0.006 (2)0.014 (3)0.007 (3)
N30.102 (5)0.046 (3)0.038 (3)0.007 (3)0.029 (3)0.010 (2)
N20.097 (5)0.037 (3)0.041 (3)0.002 (3)0.040 (3)0.003 (2)
C70.055 (3)0.044 (3)0.028 (3)0.014 (3)0.019 (2)0.006 (2)
C60.046 (3)0.038 (3)0.036 (3)0.007 (2)0.012 (2)0.004 (2)
C50.044 (3)0.032 (3)0.032 (3)0.004 (2)0.012 (2)0.002 (2)
C40.041 (3)0.046 (3)0.027 (3)0.012 (2)0.007 (2)0.005 (2)
C80.053 (3)0.040 (3)0.031 (3)0.014 (3)0.013 (2)0.004 (2)
C30.053 (3)0.048 (4)0.038 (3)0.003 (3)0.021 (3)0.005 (3)
C100.073 (4)0.043 (4)0.047 (4)0.010 (3)0.013 (3)0.016 (3)
C120.089 (5)0.044 (4)0.034 (3)0.012 (3)0.031 (3)0.005 (3)
C20.052 (3)0.034 (3)0.049 (4)0.004 (2)0.017 (3)0.006 (3)
C140.056 (4)0.061 (4)0.055 (4)0.023 (3)0.000 (3)0.018 (3)
F10.088 (4)0.073 (4)0.306 (15)0.009 (3)0.049 (7)0.069 (6)
C130.048 (4)0.049 (4)0.096 (6)0.011 (3)0.006 (4)0.014 (4)
F30.238 (13)0.091 (6)0.185 (11)0.044 (7)0.060 (9)0.029 (6)
F20.211 (11)0.184 (10)0.260 (14)0.045 (9)0.113 (11)0.120 (10)
O20.084 (5)0.081 (5)0.085 (5)0.025 (2)0.005 (2)0.013 (2)
O30.061 (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—C91.325 (8)N2—C61.280 (8)
N4—Ag1i2.226 (5)C7—C81.455 (9)
N4—C101.344 (9)C6—C41.460 (8)
C11—H110.9300C5—H50.9300
C11—C101.356 (11)C5—C41.381 (8)
C11—C121.384 (11)C4—C31.375 (9)
C9—H90.9300C8—C121.379 (9)
C9—C81.386 (9)C3—H30.9300
Ag1—N4i2.226 (5)C3—C21.385 (10)
Ag1—Ag1ii3.0943 (10)C10—H100.9300
Ag1—N12.236 (5)C12—H120.9300
Ag1—O2ii2.482 (14)C2—H20.9300
Ag1—O32.690 (9)C14—F11.290 (10)
Ag1—O3'2.696 (15)C14—C131.451 (11)
Ag1—O3'ii2.42 (2)C14—F31.273 (11)
O1—C71.366 (7)C14—F21.245 (11)
O1—C61.354 (7)C13—O21.223 (13)
N1—C11.347 (10)C13—O31.286 (12)
N1—C51.330 (8)C13—O3'1.221 (14)
C1—H10.9300C13—O2'1.254 (15)
C1—C21.359 (10)O2—Ag1ii2.482 (14)
N3—N21.427 (9)O3'—Ag1ii2.42 (2)
N3—C71.272 (9)
C9—N4—Ag1i120.9 (4)N2—C6—C4126.5 (6)
C9—N4—C10118.2 (6)N1—C5—H5118.5
C10—N4—Ag1i120.6 (5)N1—C5—C4122.9 (5)
C10—C11—H11120.8C4—C5—H5118.5
C10—C11—C12118.5 (6)C5—C4—C6122.3 (5)
C12—C11—H11120.8C3—C4—C6118.8 (5)
N4—C9—H9119.0C3—C4—C5118.9 (5)
N4—C9—C8122.0 (5)C9—C8—C7121.2 (5)
C8—C9—H9119.0C12—C8—C9119.0 (6)
N4i—Ag1—Ag1ii112.71 (14)C12—C8—C7119.8 (6)
N4i—Ag1—N1155.8 (2)C4—C3—H3120.9
N4i—Ag1—O2ii92.4 (4)C4—C3—C2118.1 (6)
N4i—Ag1—O382.1 (3)C2—C3—H3120.9
N4i—Ag1—O3'88.5 (4)N4—C10—C11123.5 (7)
N4i—Ag1—O3'ii121.5 (4)N4—C10—H10118.3
N1—Ag1—Ag1ii80.06 (13)C11—C10—H10118.3
N1—Ag1—O2ii108.1 (4)C11—C12—H12120.6
N1—Ag1—O385.3 (3)C8—C12—C11118.8 (6)
N1—Ag1—O3'85.2 (4)C8—C12—H12120.6
N1—Ag1—O3'ii82.7 (4)C1—C2—C3119.8 (6)
O2ii—Ag1—Ag1ii92.4 (3)C1—C2—H2120.1
O2ii—Ag1—O3152.0 (4)C3—C2—H2120.1
O2ii—Ag1—O3'137.1 (5)F1—C14—C13115.2 (7)
O3—Ag1—Ag1ii65.2 (3)F3—C14—F1105.0 (10)
O3—Ag1—O3'16.5 (4)F3—C14—C13112.6 (8)
O3'ii—Ag1—Ag1ii57.0 (4)F2—C14—F1109.2 (10)
O3'—Ag1—Ag1ii48.8 (5)F2—C14—C13115.4 (9)
O3'ii—Ag1—O2ii40.3 (4)F2—C14—F397.7 (11)
O3'ii—Ag1—O3122.1 (3)O2—C13—C14125.3 (10)
O3'ii—Ag1—O3'105.8 (4)O2—C13—O3122.5 (11)
C6—O1—C7102.2 (5)O2—C13—O2'41.3 (14)
C1—N1—Ag1119.5 (5)O3—C13—C14111.0 (8)
C5—N1—Ag1122.7 (4)O3'—C13—C14141.6 (14)
C5—N1—C1117.7 (6)O3'—C13—O287.4 (13)
N1—C1—H1118.8O3'—C13—O335.9 (9)
N1—C1—C2122.5 (6)O3'—C13—O2'116.8 (18)
C2—C1—H1118.8O2'—C13—C14101.6 (17)
C7—N3—N2104.5 (5)O2'—C13—O3139.3 (16)
C6—N2—N3106.8 (5)C13—O2—Ag1ii113.4 (10)
O1—C7—C8119.6 (5)C13—O3—Ag1135.1 (8)
N3—C7—O1114.0 (6)Ag1ii—O3'—Ag174.2 (4)
N3—C7—C8126.4 (6)C13—O3'—Ag1139.8 (13)
O1—C6—C4121.0 (5)C13—O3'—Ag1ii117.3 (14)
N2—C6—O1112.4 (5)
N4—C9—C8—C7178.6 (6)C10—C11—C12—C81.5 (13)
N4—C9—C8—C121.1 (10)C12—C11—C10—N40.9 (14)
N4i—Ag1—N1—C1155.7 (5)C14—C13—O2—Ag1ii169.7 (7)
N4i—Ag1—N1—C526.9 (8)C14—C13—O3—Ag1154.3 (8)
N4i—Ag1—O3—C13158.8 (11)C14—C13—O3'—Ag199 (2)
N4i—Ag1—O3'—Ag1ii122.4 (3)C14—C13—O3'—Ag1ii163.0 (10)
N4i—Ag1—O3'—C13124 (2)F1—C14—C13—O245.8 (16)
C9—N4—C10—C112.3 (11)F1—C14—C13—O3121.6 (11)
C9—C8—C12—C112.5 (11)F1—C14—C13—O3'98 (2)
Ag1i—N4—C9—C8173.7 (4)F1—C14—C13—O2'83.2 (18)
Ag1i—N4—C10—C11172.7 (7)F3—C14—C13—O2166.2 (14)
Ag1ii—Ag1—N1—C179.9 (5)F3—C14—C13—O31.2 (13)
Ag1ii—Ag1—N1—C597.5 (5)F3—C14—C13—O3'23 (2)
Ag1ii—Ag1—O3—C1339.2 (10)F3—C14—C13—O2'156.4 (18)
Ag1ii—Ag1—O3'—C13114 (2)F2—C14—C13—O282.9 (16)
Ag1—N1—C1—C2178.6 (5)F2—C14—C13—O3109.7 (13)
Ag1—N1—C5—C4177.8 (4)F2—C14—C13—O3'134 (2)
O1—C7—C8—C96.7 (9)F2—C14—C13—O2'45.5 (19)
O1—C7—C8—C12173.1 (6)O2ii—Ag1—N1—C19.4 (6)
O1—C6—C4—C51.5 (9)O2ii—Ag1—N1—C5173.2 (5)
O1—C6—C4—C3176.0 (5)O2ii—Ag1—O3—C1378.7 (14)
N1—Ag1—O3—C1342.0 (11)O2ii—Ag1—O3'—Ag1ii30.5 (8)
N1—Ag1—O3'—Ag1ii81.0 (3)O2ii—Ag1—O3'—C13144 (2)
N1—Ag1—O3'—C1333 (2)O2—C13—O3—Ag137.9 (17)
N1—C1—C2—C32.2 (11)O2—C13—O3'—Ag1ii12.2 (13)
N1—C5—C4—C6178.2 (5)O2—C13—O3'—Ag1110 (2)
N1—C5—C4—C30.8 (9)O3—Ag1—N1—C1145.5 (6)
C1—N1—C5—C40.3 (9)O3—Ag1—N1—C531.9 (5)
N3—N2—C6—O10.6 (9)O3—Ag1—O3'—Ag1ii170.9 (17)
N3—N2—C6—C4178.1 (6)O3—Ag1—O3'—C1357.1 (19)
N3—C7—C8—C9175.7 (7)O3—C13—O2—Ag1ii3.7 (15)
N3—C7—C8—C124.5 (11)O3—C13—O3'—Ag1ii156 (2)
N2—N3—C7—O10.7 (9)O3—C13—O3'—Ag159 (2)
N2—N3—C7—C8178.4 (7)O3'ii—Ag1—N1—C122.3 (7)
N2—C6—C4—C5180.0 (7)O3'—Ag1—N1—C1128.9 (7)
N2—C6—C4—C32.5 (10)O3'ii—Ag1—N1—C5155.2 (6)
C7—O1—C6—N20.2 (7)O3'—Ag1—N1—C548.5 (6)
C7—O1—C6—C4178.6 (5)O3'—Ag1—O3—C1346.7 (14)
C7—N3—N2—C60.8 (9)O3'ii—Ag1—O3—C1336.4 (13)
C7—C8—C12—C11177.3 (7)O3'ii—Ag1—O3'—Ag1ii0.0
C6—O1—C7—N30.4 (8)O3'ii—Ag1—O3'—C13114 (2)
C6—O1—C7—C8178.3 (5)O3'—C13—O2—Ag1ii11.5 (12)
C6—C4—C3—C2179.4 (6)O3'—C13—O3—Ag151.3 (18)
C5—N1—C1—C21.0 (10)O2'—C13—O2—Ag1ii126 (3)
C5—C4—C3—C21.9 (9)O2'—C13—O3—Ag113 (3)
C4—C3—C2—C12.6 (10)O2'—C13—O3'—Ag1ii18 (2)
C10—N4—C9—C81.2 (9)O2'—C13—O3'—Ag180 (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
C22H15N5O2F(000) = 792
Mr = 381.39Dx = 1.400 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 7.7222 (3) ÅCell parameters from 2321 reflections
b = 11.5401 (5) Åθ = 8.5–70.3°
c = 20.4160 (8) ŵ = 0.77 mm1
β = 95.965 (4)°T = 296 K
V = 1809.51 (13) Å3Needle, clear light colourless
Z = 40.29 × 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 Source2447 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.056
Detector resolution: 16.0793 pixels mm-1θmax = 67.1°, θmin = 4.4°
ω scansh = 59
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1313
Tmin = 0.178, Tmax = 1.000l = 2424
6339 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239H 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 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
O11.0869 (2)0.41554 (16)0.21033 (9)0.0500 (5)
O20.5872 (2)0.47643 (16)0.10943 (8)0.0494 (5)
C80.9274 (3)0.4315 (2)0.10155 (13)0.0468 (6)
C41.2278 (3)0.4503 (2)0.31995 (13)0.0479 (7)
N40.6380 (3)0.6356 (2)0.05112 (12)0.0606 (7)
N21.1123 (4)0.5980 (2)0.23992 (13)0.0661 (8)
C160.4228 (3)0.5498 (2)0.20800 (12)0.0454 (6)
C71.0108 (3)0.4844 (2)0.16136 (13)0.0461 (6)
N50.5393 (3)0.6645 (2)0.11088 (12)0.0612 (7)
C130.8382 (3)0.5005 (2)0.05366 (13)0.0477 (7)
H130.83270.58020.05990.057*
C150.5139 (3)0.5690 (2)0.14316 (14)0.0473 (6)
N31.0241 (3)0.5930 (2)0.17581 (12)0.0634 (7)
C61.1432 (3)0.4931 (2)0.25772 (13)0.0468 (6)
C90.9359 (4)0.3132 (3)0.09219 (14)0.0625 (8)
H90.99410.26630.12440.075*
C140.6617 (3)0.5253 (2)0.05257 (12)0.0452 (6)
C110.7680 (4)0.3331 (3)0.01308 (14)0.0632 (8)
H110.71530.29970.05160.076*
C170.3409 (4)0.6415 (3)0.24271 (14)0.0562 (7)
H170.34140.71480.22380.067*
C200.3358 (4)0.4254 (3)0.30020 (15)0.0617 (8)
H200.33460.35220.31920.074*
C210.4172 (4)0.4413 (3)0.23717 (15)0.0571 (7)
H210.46860.37850.21420.069*
C120.7572 (3)0.4515 (3)0.00327 (13)0.0482 (6)
C100.8573 (5)0.2651 (3)0.03455 (15)0.0727 (10)
H100.86470.18560.02790.087*
N11.3639 (4)0.4951 (3)0.42801 (13)0.0761 (8)
C31.2416 (4)0.3341 (3)0.33341 (15)0.0654 (8)
H31.19920.27970.30220.079*
C51.2931 (4)0.5274 (3)0.36864 (14)0.0612 (8)
H51.28690.60620.35920.073*
C21.3195 (5)0.2992 (3)0.39419 (16)0.0756 (10)
H21.33370.22080.40390.091*
C180.2584 (4)0.6241 (3)0.30552 (14)0.0587 (8)
H180.20330.68620.32800.070*
C190.2561 (4)0.5171 (3)0.33547 (14)0.0560 (7)
C220.1721 (4)0.5007 (4)0.40454 (15)0.0768 (10)
H22A0.05540.53030.40790.115*
H22B0.16960.41970.41530.115*
H22C0.23780.54170.43460.115*
C11.3749 (5)0.3802 (3)0.43925 (17)0.0746 (10)
H11.42340.35520.48040.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0458 (11)0.0516 (11)0.0487 (11)0.0032 (8)0.0131 (8)0.0007 (8)
O20.0465 (11)0.0522 (10)0.0465 (10)0.0010 (8)0.0086 (8)0.0027 (8)
C80.0320 (13)0.0602 (16)0.0460 (14)0.0039 (11)0.0069 (10)0.0008 (11)
C40.0374 (14)0.0551 (15)0.0483 (15)0.0049 (11)0.0100 (11)0.0011 (12)
N40.0604 (16)0.0575 (15)0.0583 (14)0.0019 (12)0.0199 (11)0.0018 (11)
N20.0695 (18)0.0539 (14)0.0669 (16)0.0041 (12)0.0314 (13)0.0008 (12)
C160.0378 (14)0.0484 (14)0.0487 (15)0.0001 (10)0.0024 (11)0.0046 (11)
C70.0272 (13)0.0573 (16)0.0508 (15)0.0009 (10)0.0099 (10)0.0066 (11)
N50.0655 (17)0.0534 (14)0.0594 (14)0.0027 (11)0.0186 (11)0.0007 (11)
C130.0344 (14)0.0543 (15)0.0522 (15)0.0030 (11)0.0064 (11)0.0002 (12)
C150.0367 (14)0.0529 (15)0.0512 (15)0.0015 (11)0.0008 (11)0.0064 (12)
N30.0606 (16)0.0549 (14)0.0670 (16)0.0014 (11)0.0293 (12)0.0011 (11)
C60.0369 (14)0.0495 (14)0.0513 (15)0.0064 (11)0.0078 (11)0.0016 (11)
C90.067 (2)0.0573 (17)0.0569 (17)0.0034 (14)0.0218 (13)0.0016 (14)
C140.0322 (13)0.0570 (15)0.0442 (14)0.0048 (11)0.0069 (10)0.0013 (11)
C110.073 (2)0.0619 (18)0.0500 (16)0.0010 (15)0.0173 (13)0.0052 (13)
C170.0586 (18)0.0513 (15)0.0558 (16)0.0051 (13)0.0080 (12)0.0039 (12)
C200.065 (2)0.0594 (18)0.0571 (18)0.0002 (14)0.0100 (14)0.0062 (14)
C210.0590 (18)0.0531 (16)0.0559 (16)0.0057 (13)0.0098 (13)0.0033 (13)
C120.0360 (14)0.0613 (15)0.0452 (14)0.0019 (11)0.0055 (10)0.0032 (12)
C100.093 (3)0.0547 (17)0.0630 (18)0.0045 (16)0.0260 (16)0.0039 (15)
N10.080 (2)0.089 (2)0.0531 (16)0.0069 (15)0.0221 (13)0.0027 (14)
C30.074 (2)0.0548 (17)0.0620 (18)0.0089 (14)0.0172 (14)0.0004 (14)
C50.067 (2)0.0620 (17)0.0509 (16)0.0055 (15)0.0130 (13)0.0041 (13)
C20.089 (3)0.066 (2)0.067 (2)0.0029 (18)0.0154 (17)0.0167 (16)
C180.0521 (17)0.0611 (17)0.0594 (17)0.0058 (13)0.0114 (13)0.0113 (13)
C190.0395 (15)0.0754 (19)0.0504 (16)0.0045 (13)0.0088 (12)0.0029 (14)
C220.067 (2)0.104 (3)0.0545 (19)0.0105 (18)0.0179 (15)0.0014 (18)
C10.073 (2)0.090 (2)0.0568 (18)0.0030 (19)0.0132 (15)0.0115 (18)
Geometric parameters (Å, º) top
O1—C71.362 (3)C11—H110.9300
O1—C61.356 (3)C11—C121.385 (4)
O2—C151.362 (3)C11—C101.377 (4)
O2—C141.363 (3)C17—H170.9300
C8—C71.454 (3)C17—C181.386 (4)
C8—C131.387 (4)C20—H200.9300
C8—C91.381 (4)C20—C211.384 (4)
C4—C61.453 (3)C20—C191.387 (4)
C4—C31.371 (4)C21—H210.9300
C4—C51.389 (4)C10—H100.9300
N4—N51.410 (3)N1—C51.330 (4)
N4—C141.287 (3)N1—C11.347 (4)
N2—N31.412 (3)C3—H30.9300
N2—C61.280 (4)C3—C21.382 (4)
C16—C151.450 (4)C5—H50.9300
C16—C171.389 (4)C2—H20.9300
C16—C211.385 (4)C2—C11.349 (5)
C7—N31.289 (4)C18—H180.9300
N5—C151.288 (4)C18—C191.378 (4)
C13—H130.9300C19—C221.501 (4)
C13—C121.382 (4)C22—H22A0.9600
C9—H90.9300C22—H22B0.9600
C9—C101.383 (4)C22—H22C0.9600
C14—C121.458 (4)C1—H10.9300
C6—O1—C7102.7 (2)C18—C17—H17119.9
C15—O2—C14102.9 (2)C21—C20—H20119.5
C13—C8—C7119.7 (3)C21—C20—C19121.1 (3)
C9—C8—C7120.5 (2)C19—C20—H20119.5
C9—C8—C13119.8 (2)C16—C21—H21119.7
C3—C4—C6121.7 (2)C20—C21—C16120.7 (3)
C3—C4—C5117.9 (3)C20—C21—H21119.7
C5—C4—C6120.3 (3)C13—C12—C14119.6 (3)
C14—N4—N5106.2 (2)C13—C12—C11119.7 (3)
C6—N2—N3106.4 (2)C11—C12—C14120.6 (2)
C17—C16—C15120.1 (3)C9—C10—H10119.5
C21—C16—C15121.4 (2)C11—C10—C9121.0 (3)
C21—C16—C17118.5 (3)C11—C10—H10119.5
O1—C7—C8119.4 (2)C5—N1—C1116.3 (3)
N3—C7—O1112.4 (2)C4—C3—H3120.6
N3—C7—C8128.2 (3)C4—C3—C2118.9 (3)
C15—N5—N4106.3 (2)C2—C3—H3120.6
C8—C13—H13119.8C4—C5—H5118.1
C12—C13—C8120.4 (3)N1—C5—C4123.9 (3)
C12—C13—H13119.8N1—C5—H5118.1
O2—C15—C16118.6 (2)C3—C2—H2120.4
N5—C15—O2112.3 (3)C1—C2—C3119.2 (3)
N5—C15—C16129.2 (3)C1—C2—H2120.4
C7—N3—N2105.7 (2)C17—C18—H18119.2
O1—C6—C4118.8 (2)C19—C18—C17121.6 (3)
N2—C6—O1112.7 (2)C19—C18—H18119.2
N2—C6—C4128.6 (3)C20—C19—C22121.1 (3)
C8—C9—H9120.3C18—C19—C20117.9 (3)
C8—C9—C10119.4 (3)C18—C19—C22120.9 (3)
C10—C9—H9120.3C19—C22—H22A109.5
O2—C14—C12119.0 (2)C19—C22—H22B109.5
N4—C14—O2112.3 (2)C19—C22—H22C109.5
N4—C14—C12128.6 (2)H22A—C22—H22B109.5
C12—C11—H11120.2H22A—C22—H22C109.5
C10—C11—H11120.2H22B—C22—H22C109.5
C10—C11—C12119.6 (3)N1—C1—C2123.8 (3)
C16—C17—H17119.9N1—C1—H1118.1
C18—C17—C16120.2 (3)C2—C1—H1118.1
O1—C7—N3—N21.4 (3)C6—C4—C5—N1176.4 (3)
O2—C14—C12—C13177.9 (2)C6—N2—N3—C70.0 (3)
O2—C14—C12—C111.9 (4)C9—C8—C7—O14.7 (4)
C8—C7—N3—N2178.5 (2)C9—C8—C7—N3175.3 (3)
C8—C13—C12—C14179.0 (2)C9—C8—C13—C120.2 (4)
C8—C13—C12—C111.1 (4)C14—O2—C15—C16179.2 (2)
C8—C9—C10—C111.2 (5)C14—O2—C15—N50.2 (3)
C4—C3—C2—C12.1 (5)C14—N4—N5—C150.6 (3)
N4—N5—C15—O20.5 (3)C17—C16—C15—O2177.6 (2)
N4—N5—C15—C16178.8 (2)C17—C16—C15—N53.1 (4)
N4—C14—C12—C130.7 (4)C17—C16—C21—C201.7 (4)
N4—C14—C12—C11179.5 (3)C17—C18—C19—C201.5 (4)
C16—C17—C18—C190.6 (4)C17—C18—C19—C22177.6 (3)
C7—O1—C6—C4177.9 (2)C21—C16—C15—O23.4 (4)
C7—O1—C6—N22.2 (3)C21—C16—C15—N5175.9 (3)
C7—C8—C13—C12179.6 (2)C21—C16—C17—C181.1 (4)
C7—C8—C9—C10179.3 (3)C21—C20—C19—C180.8 (5)
N5—N4—C14—O20.5 (3)C21—C20—C19—C22178.3 (3)
N5—N4—C14—C12179.2 (3)C12—C11—C10—C90.2 (5)
C13—C8—C7—O1175.1 (2)C10—C11—C12—C130.9 (4)
C13—C8—C7—N34.9 (4)C10—C11—C12—C14179.2 (3)
C13—C8—C9—C101.0 (4)C3—C4—C6—O14.4 (4)
C15—O2—C14—N40.2 (3)C3—C4—C6—N2175.7 (3)
C15—O2—C14—C12179.0 (2)C3—C4—C5—N11.8 (5)
C15—C16—C17—C18178.0 (2)C3—C2—C1—N12.2 (6)
C15—C16—C21—C20177.3 (2)C5—C4—C6—O1177.5 (2)
N3—N2—C6—O11.4 (3)C5—C4—C6—N22.4 (4)
N3—N2—C6—C4178.6 (2)C5—C4—C3—C20.2 (5)
C6—O1—C7—C8177.8 (2)C5—N1—C1—C20.3 (6)
C6—O1—C7—N32.2 (3)C19—C20—C21—C160.8 (5)
C6—C4—C3—C2178.3 (3)C1—N1—C5—C41.8 (5)
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-disilver(I) dichloromethane monosolvate (exp_3309) top
Crystal data top
[Ag4(C2F3O2)4(C22H15N5O2)2]·CH2Cl2F(000) = 3384
Mr = 1731.26Dx = 1.925 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 20.3700 (6) ÅCell parameters from 6547 reflections
b = 15.0076 (3) Åθ = 6.3–71.2°
c = 19.5451 (5) ŵ = 12.15 mm1
β = 90.133 (3)°T = 293 K
V = 5975.0 (3) Å3Plate, colourless
Z = 40.17 × 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 Source4035 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.034
Detector resolution: 16.0793 pixels mm-1θmax = 67.1°, θmin = 3.7°
ω scansh = 2224
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1517
Tmin = 0.264, Tmax = 1.000l = 2223
20309 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H 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 parametersΔρmax = 1.02 e Å3
0 restraintsΔρmin = 1.38 e Å3
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
xyzUiso*/UeqOcc. (<1)
Ag10.31738 (3)0.23588 (3)0.31431 (3)0.0883 (2)
Ag20.28858 (3)0.32296 (3)0.46872 (3)0.0755 (2)
C10.1836 (4)0.4163 (4)0.7937 (3)0.0735 (17)
H10.16730.37180.82210.088*
C20.1912 (4)0.5005 (4)0.8197 (3)0.0717 (16)
H20.18190.51220.86530.086*
C30.2128 (3)0.5670 (4)0.7776 (3)0.0648 (14)
H30.21590.62530.79350.078*
C40.2300 (3)0.5464 (3)0.7109 (3)0.0526 (12)
C50.2218 (3)0.4601 (3)0.6884 (3)0.0595 (14)
H50.23280.44630.64350.071*
C60.2557 (3)0.6136 (3)0.6648 (3)0.0503 (11)
C70.2986 (3)0.6652 (3)0.5741 (3)0.0543 (12)
C80.3252 (3)0.6634 (3)0.5058 (3)0.0523 (12)
C90.3289 (3)0.5845 (3)0.4688 (3)0.0546 (12)
H90.31250.53190.48730.066*
C100.3568 (3)0.5845 (3)0.4044 (3)0.0531 (12)
C110.3813 (3)0.6629 (4)0.3766 (3)0.0657 (15)
H110.40090.66240.33370.079*
C120.3764 (4)0.7416 (4)0.4130 (3)0.0702 (16)
H120.39150.79450.39380.084*
C130.3494 (3)0.7422 (4)0.4776 (3)0.0650 (15)
H130.34720.79510.50230.078*
C140.3628 (3)0.5006 (3)0.3663 (3)0.0523 (12)
C150.3904 (3)0.4186 (3)0.2818 (3)0.0512 (11)
C160.4193 (3)0.3967 (4)0.2161 (3)0.0557 (12)
C170.4354 (3)0.3098 (4)0.2000 (3)0.0659 (15)
H170.42550.26410.23040.079*
C180.4665 (3)0.2903 (5)0.1384 (3)0.0730 (16)
H180.47710.23160.12800.088*
C190.4820 (3)0.3578 (5)0.0919 (3)0.0731 (17)
C200.4639 (4)0.4427 (5)0.1086 (3)0.086 (2)
H200.47210.48820.07750.103*
C210.4338 (4)0.4635 (5)0.1699 (3)0.0790 (19)
H210.42340.52240.18010.095*
C220.5161 (4)0.3366 (7)0.0265 (4)0.105 (3)
H22A0.48450.31730.00680.157*
H22B0.54760.29000.03430.157*
H22C0.53820.38880.01010.157*
C230.1002 (5)0.2335 (6)0.3442 (5)0.103 (3)
C240.1607 (4)0.2096 (4)0.3833 (4)0.0742 (17)
C250.1564 (4)0.3841 (5)0.5237 (4)0.0778 (18)
C260.0966 (6)0.4461 (6)0.5281 (6)0.113 (3)
C270.492 (2)0.9874 (19)0.2155 (17)0.208 (19)0.50
H27A0.46330.98690.17650.250*0.50
H27B0.53420.96410.20280.250*0.50
Cl10.4597 (6)0.9270 (7)0.2879 (7)0.237 (5)0.50
Cl20.50001.0900 (4)0.25000.248 (4)
F10.1098 (5)0.5145 (6)0.5652 (7)0.240 (5)
F20.0461 (4)0.4155 (6)0.5494 (8)0.256 (7)
F30.0826 (5)0.4838 (9)0.4730 (5)0.254 (6)
F40.0783 (5)0.3130 (6)0.3635 (7)0.243 (6)
F50.0513 (4)0.1835 (5)0.3474 (5)0.173 (3)
F60.1107 (5)0.2523 (9)0.2818 (4)0.227 (5)
N10.3618 (2)0.3676 (3)0.3261 (2)0.0531 (10)
N20.3449 (2)0.4213 (3)0.3818 (2)0.0549 (10)
N30.2959 (3)0.7306 (3)0.6164 (3)0.0643 (12)
N40.2681 (3)0.6966 (3)0.6769 (3)0.0636 (12)
N60.1987 (3)0.3956 (3)0.7288 (3)0.0693 (14)
O10.39189 (19)0.5039 (2)0.30364 (17)0.0555 (9)
O20.27373 (18)0.5888 (2)0.60118 (17)0.0529 (8)
O30.2097 (3)0.2570 (4)0.3737 (3)0.0918 (15)
O40.2010 (3)0.4150 (4)0.4898 (3)0.1042 (17)
O50.1528 (3)0.1487 (4)0.4251 (3)0.1084 (18)
O60.1497 (3)0.3123 (3)0.5521 (3)0.0916 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.1187 (5)0.0412 (3)0.1051 (4)0.0113 (2)0.0456 (3)0.0104 (2)
Ag20.0806 (4)0.0745 (3)0.0715 (3)0.0062 (2)0.0202 (2)0.0148 (2)
C10.105 (5)0.058 (3)0.057 (3)0.001 (3)0.017 (3)0.006 (3)
C20.091 (5)0.073 (4)0.051 (3)0.006 (3)0.007 (3)0.007 (3)
C30.075 (4)0.058 (3)0.062 (3)0.005 (3)0.012 (3)0.017 (3)
C40.058 (3)0.044 (3)0.056 (3)0.002 (2)0.004 (2)0.006 (2)
C50.084 (4)0.044 (3)0.051 (3)0.001 (2)0.008 (3)0.003 (2)
C60.054 (3)0.048 (3)0.049 (3)0.001 (2)0.005 (2)0.011 (2)
C70.054 (3)0.043 (3)0.066 (3)0.003 (2)0.000 (3)0.004 (2)
C80.055 (3)0.045 (3)0.057 (3)0.000 (2)0.001 (2)0.001 (2)
C90.062 (3)0.044 (3)0.058 (3)0.009 (2)0.004 (2)0.005 (2)
C100.060 (3)0.046 (3)0.054 (3)0.007 (2)0.004 (2)0.001 (2)
C110.088 (4)0.055 (3)0.055 (3)0.011 (3)0.005 (3)0.008 (2)
C120.093 (5)0.044 (3)0.073 (4)0.018 (3)0.009 (3)0.006 (3)
C130.076 (4)0.045 (3)0.074 (4)0.007 (2)0.000 (3)0.002 (2)
C140.059 (3)0.050 (3)0.048 (3)0.005 (2)0.006 (2)0.003 (2)
C150.057 (3)0.048 (3)0.049 (3)0.001 (2)0.006 (2)0.004 (2)
C160.059 (3)0.059 (3)0.049 (3)0.001 (2)0.008 (2)0.001 (2)
C170.070 (4)0.064 (3)0.064 (4)0.002 (3)0.012 (3)0.001 (3)
C180.068 (4)0.086 (4)0.065 (4)0.010 (3)0.012 (3)0.015 (3)
C190.061 (4)0.103 (5)0.055 (3)0.001 (3)0.006 (3)0.006 (3)
C200.100 (5)0.098 (5)0.061 (4)0.001 (4)0.027 (4)0.014 (3)
C210.103 (5)0.071 (4)0.064 (4)0.005 (3)0.030 (4)0.007 (3)
C220.087 (6)0.154 (8)0.073 (5)0.002 (5)0.026 (4)0.019 (5)
C230.135 (8)0.079 (5)0.093 (6)0.023 (5)0.000 (5)0.002 (4)
C240.084 (5)0.065 (3)0.074 (4)0.004 (3)0.024 (4)0.014 (3)
C250.083 (5)0.075 (4)0.076 (4)0.024 (3)0.009 (4)0.004 (3)
C260.122 (8)0.086 (6)0.131 (8)0.044 (5)0.042 (6)0.021 (5)
C270.22 (3)0.14 (2)0.26 (5)0.06 (2)0.07 (4)0.04 (2)
Cl10.237 (11)0.199 (9)0.275 (13)0.026 (8)0.002 (8)0.069 (9)
Cl20.256 (8)0.112 (4)0.377 (12)0.0000.052 (8)0.000
F10.215 (9)0.156 (7)0.349 (15)0.080 (7)0.003 (9)0.114 (9)
F20.125 (6)0.156 (7)0.487 (19)0.063 (5)0.135 (9)0.084 (9)
F30.221 (10)0.333 (14)0.210 (9)0.186 (10)0.033 (7)0.097 (10)
F40.219 (10)0.129 (6)0.380 (16)0.068 (6)0.119 (10)0.029 (7)
F50.117 (5)0.134 (5)0.269 (10)0.029 (4)0.052 (6)0.028 (5)
F60.200 (9)0.399 (16)0.082 (4)0.014 (9)0.016 (5)0.009 (7)
N10.062 (3)0.044 (2)0.054 (2)0.0004 (18)0.014 (2)0.0006 (17)
N20.065 (3)0.049 (2)0.051 (2)0.0036 (18)0.013 (2)0.0009 (18)
N30.078 (3)0.048 (2)0.067 (3)0.008 (2)0.011 (3)0.010 (2)
N40.080 (3)0.044 (2)0.067 (3)0.007 (2)0.016 (2)0.010 (2)
N60.104 (4)0.040 (2)0.065 (3)0.003 (2)0.016 (3)0.004 (2)
O10.069 (2)0.0487 (18)0.0485 (19)0.0105 (15)0.0127 (17)0.0020 (14)
O20.067 (2)0.0395 (16)0.0522 (19)0.0040 (14)0.0056 (16)0.0080 (14)
O30.086 (4)0.093 (3)0.096 (4)0.006 (3)0.017 (3)0.023 (3)
O40.094 (4)0.093 (4)0.126 (5)0.011 (3)0.024 (3)0.027 (3)
O50.124 (5)0.101 (4)0.101 (4)0.016 (3)0.009 (3)0.036 (3)
O60.101 (4)0.085 (3)0.088 (3)0.028 (3)0.012 (3)0.020 (3)
Geometric parameters (Å, º) top
Ag1—Ag23.3419 (7)C15—O11.351 (6)
Ag1—N12.186 (4)C16—C171.382 (8)
Ag1—N6i2.170 (5)C16—C211.383 (8)
Ag1—O32.504 (5)C17—H170.9300
Ag2—Ag2i2.9615 (9)C17—C181.392 (8)
Ag2—N22.528 (4)C18—H180.9300
Ag2—O42.295 (6)C18—C191.397 (10)
Ag2—O5i2.430 (6)C19—C201.366 (10)
Ag2—O6i2.423 (5)C19—C221.490 (9)
Ag2—O32.646 (2)C20—H200.9300
C1—H10.9300C20—C211.384 (9)
C1—C21.370 (9)C21—H210.9300
C1—N61.343 (8)C22—H22A0.9600
C2—H20.9300C22—H22B0.9600
C2—C31.367 (9)C22—H22C0.9600
C3—H30.9300C23—C241.493 (13)
C3—C41.386 (8)C23—F41.329 (12)
C4—C51.377 (7)C23—F51.248 (11)
C4—C61.450 (7)C23—F61.269 (11)
C5—H50.9300C24—O31.241 (8)
C5—N61.335 (7)C24—O51.235 (8)
C6—N41.293 (6)C25—C261.536 (10)
C6—O21.349 (6)C25—O41.218 (9)
C7—C81.443 (8)C25—O61.220 (8)
C7—N31.284 (7)C26—F11.285 (14)
C7—O21.361 (6)C26—F21.202 (12)
C8—C91.389 (7)C26—F31.248 (12)
C8—C131.395 (7)C27—C27ii1.39 (7)
C9—H90.9300C27—H27A0.9596
C9—C101.383 (7)C27—H27B0.9596
C10—C111.389 (7)C27—Cl11.81 (3)
C10—C141.468 (7)C27—Cl1ii1.34 (3)
C11—H110.9300C27—Cl21.69 (3)
C11—C121.384 (8)Cl1—C27ii1.34 (3)
C12—H120.9300Cl1—Cl1ii2.21 (3)
C12—C131.378 (9)Cl2—C27ii1.69 (3)
C13—H130.9300N1—N21.397 (6)
C14—N21.281 (6)N3—N41.407 (7)
C14—O11.363 (6)N6—Ag1i2.170 (5)
C15—C161.451 (7)O5—Ag2i2.430 (6)
C15—N11.296 (6)O6—Ag2i2.422 (5)
N1—Ag1—Ag267.93 (11)C17—C18—H18119.5
N1—Ag1—O3101.49 (17)C17—C18—C19120.9 (6)
N6i—Ag1—Ag2132.79 (13)C19—C18—H18119.5
N6i—Ag1—N1157.74 (18)C18—C19—C22120.6 (7)
N6i—Ag1—O399.4 (2)C20—C19—C18117.4 (6)
O3—Ag1—Ag251.41 (13)C20—C19—C22122.0 (7)
Ag2i—Ag2—Ag1100.26 (3)C19—C20—H20118.7
N2—Ag2—Ag162.62 (10)C19—C20—C21122.5 (7)
N2—Ag2—Ag2i162.04 (10)C21—C20—H20118.7
O4—Ag2—Ag1122.37 (17)C16—C21—C20119.9 (7)
O4—Ag2—Ag2i87.57 (14)C16—C21—H21120.1
O4—Ag2—N297.09 (17)C20—C21—H21120.1
O4—Ag2—O5i97.0 (2)C19—C22—H22A109.5
O4—Ag2—O6i159.8 (2)C19—C22—H22B109.5
O5i—Ag2—Ag1138.86 (16)C19—C22—H22C109.5
O5i—Ag2—Ag2i92.11 (13)H22A—C22—H22B109.5
O5i—Ag2—N2104.44 (17)H22A—C22—H22C109.5
O6i—Ag2—Ag155.13 (13)H22B—C22—H22C109.5
O6i—Ag2—Ag2i74.07 (14)F4—C23—C24110.3 (8)
O6i—Ag2—N298.03 (16)F5—C23—C24119.1 (8)
O6i—Ag2—O5i92.1 (2)F5—C23—F4104.9 (11)
C2—C1—H1118.8F5—C23—F6108.6 (10)
N6—C1—H1118.8F6—C23—C24113.9 (10)
N6—C1—C2122.4 (6)F6—C23—F497.5 (10)
C1—C2—H2120.4O3—C24—C23116.6 (6)
C3—C2—C1119.2 (5)O5—C24—C23114.1 (7)
C3—C2—H2120.4O5—C24—O3129.1 (8)
C2—C3—H3120.5O4—C25—C26113.1 (7)
C2—C3—C4119.0 (5)O4—C25—O6132.0 (7)
C4—C3—H3120.5O6—C25—C26114.9 (7)
C3—C4—C6121.4 (5)F1—C26—C25110.5 (10)
C5—C4—C3118.7 (5)F2—C26—C25117.9 (8)
C5—C4—C6119.9 (5)F2—C26—F1106.7 (11)
C4—C5—H5118.8F2—C26—F3106.2 (13)
N6—C5—C4122.4 (5)F3—C26—C25114.0 (8)
N6—C5—H5118.8F3—C26—F199.9 (11)
N4—C6—C4128.9 (5)C27ii—C27—H27A155.9
N4—C6—O2112.3 (4)C27ii—C27—H27B92.6
O2—C6—C4118.7 (4)C27ii—C27—Cl147.4 (17)
N3—C7—C8128.8 (5)C27ii—C27—Cl265.8 (12)
N3—C7—O2112.1 (5)H27A—C27—H27B109.6
O2—C7—C8119.0 (4)Cl1ii—C27—C27ii83 (3)
C9—C8—C7121.2 (5)Cl1—C27—H27A113.2
C9—C8—C13119.8 (5)Cl1ii—C27—H27A113.7
C13—C8—C7118.9 (5)Cl1ii—C27—H27B23.7
C8—C9—H9120.1Cl1—C27—H27B110.5
C10—C9—C8119.7 (5)Cl1ii—C27—Cl188 (2)
C10—C9—H9120.1Cl1ii—C27—Cl2125 (3)
C9—C10—C11120.3 (5)Cl2—C27—H27A112.4
C9—C10—C14119.8 (4)Cl2—C27—H27B110.5
C11—C10—C14119.8 (5)Cl2—C27—Cl1100.4 (15)
C10—C11—H11120.1C27ii—Cl1—C2750 (3)
C12—C11—C10119.7 (6)C27—Cl1—Cl1ii37.2 (11)
C12—C11—H11120.1C27ii—Cl1—Cl1ii54.6 (16)
C11—C12—H12119.8C27—Cl2—C27ii48 (2)
C13—C12—C11120.4 (5)C15—N1—Ag1130.5 (4)
C13—C12—H12119.8C15—N1—N2107.0 (4)
C8—C13—H13120.0N2—N1—Ag1120.1 (3)
C12—C13—C8119.9 (5)C14—N2—Ag2146.2 (4)
C12—C13—H13120.0C14—N2—N1106.4 (4)
N2—C14—C10130.8 (5)N1—N2—Ag2107.4 (3)
N2—C14—O1111.8 (4)C7—N3—N4106.4 (4)
O1—C14—C10117.5 (4)C6—N4—N3106.0 (4)
N1—C15—C16129.9 (5)C1—N6—Ag1i122.8 (4)
N1—C15—O1111.0 (4)C5—N6—Ag1i118.9 (4)
O1—C15—C16119.0 (4)C5—N6—C1118.3 (5)
C17—C16—C15120.9 (5)C15—O1—C14103.9 (4)
C17—C16—C21119.0 (5)C6—O2—C7103.2 (4)
C21—C16—C15120.1 (5)C24—O3—Ag1134.7 (5)
C16—C17—H17119.8C25—O4—Ag2116.7 (5)
C16—C17—C18120.3 (6)C24—O5—Ag2i111.7 (5)
C18—C17—H17119.8C25—O6—Ag2i127.2 (5)
Ag1—Ag2—N2—C14166.8 (8)Cl1ii—C27—Cl2—C27ii62 (3)
Ag1—Ag2—N2—N19.9 (3)Cl2—C27—Cl1—C27ii42.7 (16)
Ag1—Ag2—O4—C25108.1 (6)Cl2—C27—Cl1—Cl1ii125 (3)
Ag1—N1—N2—Ag215.6 (4)F4—C23—C24—O364.8 (12)
Ag1—N1—N2—C14162.5 (4)F4—C23—C24—O5109.8 (10)
Ag2—Ag1—N1—C15172.1 (5)F5—C23—C24—O3173.9 (9)
Ag2—Ag1—N1—N212.1 (3)F5—C23—C24—O511.5 (13)
Ag2—Ag1—O3—C24133.6 (7)F6—C23—C24—O343.6 (12)
Ag2i—Ag2—N2—C14148.1 (6)F6—C23—C24—O5141.7 (10)
Ag2i—Ag2—N2—N128.6 (6)N1—Ag1—Ag2—Ag2i179.31 (13)
Ag2i—Ag2—O4—C257.5 (6)N1—Ag1—Ag2—N26.46 (18)
C1—C2—C3—C43.8 (10)N1—Ag1—Ag2—O487.0 (2)
C2—C1—N6—Ag1i177.1 (5)N1—Ag1—Ag2—O5i74.0 (2)
C2—C1—N6—C50.2 (11)N1—Ag1—Ag2—O6i117.1 (2)
C2—C3—C4—C53.0 (9)N1—Ag1—O3—C24177.2 (7)
C2—C3—C4—C6177.5 (6)N1—C15—C16—C1717.9 (10)
C3—C4—C5—N60.8 (9)N1—C15—C16—C21165.1 (6)
C3—C4—C6—N42.4 (9)N1—C15—O1—C141.2 (6)
C3—C4—C6—O2177.7 (5)N2—Ag2—O4—C25170.1 (6)
C4—C5—N6—Ag1i176.4 (5)N2—C14—O1—C150.1 (6)
C4—C5—N6—C10.6 (10)N3—C7—C8—C9174.8 (6)
C4—C6—N4—N3176.4 (5)N3—C7—C8—C133.3 (9)
C4—C6—O2—C7176.4 (5)N3—C7—O2—C60.3 (6)
C5—C4—C6—N4178.2 (6)N4—C6—O2—C70.3 (6)
C5—C4—C6—O22.8 (8)N6i—Ag1—Ag2—Ag2i9.1 (2)
C6—C4—C5—N6179.7 (6)N6i—Ag1—Ag2—N2176.7 (2)
C7—C8—C9—C10177.6 (5)N6i—Ag1—Ag2—O4102.7 (3)
C7—C8—C13—C12178.4 (6)N6i—Ag1—Ag2—O5i96.2 (3)
C7—N3—N4—C61.0 (6)N6i—Ag1—Ag2—O6i53.2 (3)
C8—C7—N3—N4177.4 (6)N6i—Ag1—N1—C1527.1 (8)
C8—C7—O2—C6178.1 (5)N6i—Ag1—N1—N2172.9 (5)
C8—C9—C10—C110.0 (9)N6i—Ag1—O3—C244.9 (7)
C8—C9—C10—C14177.9 (5)N6—C1—C2—C32.4 (11)
C9—C8—C13—C120.3 (9)O1—C14—N2—Ag2177.6 (5)
C9—C10—C11—C121.3 (10)O1—C14—N2—N11.0 (6)
C9—C10—C14—N21.2 (9)O1—C15—C16—C17161.9 (5)
C9—C10—C14—O1178.7 (5)O1—C15—C16—C2115.1 (8)
C10—C11—C12—C132.1 (11)O1—C15—N1—Ag1160.1 (3)
C10—C14—N2—Ag22.5 (12)O1—C15—N1—N21.9 (6)
C10—C14—N2—N1179.1 (6)O2—C6—N4—N30.8 (6)
C10—C14—O1—C15179.8 (5)O2—C7—C8—C93.3 (8)
C11—C10—C14—N2179.0 (6)O2—C7—C8—C13178.6 (5)
C11—C10—C14—O10.9 (8)O2—C7—N3—N40.8 (6)
C11—C12—C13—C81.6 (10)O3—Ag1—Ag2—Ag2i53.94 (15)
C13—C8—C9—C100.5 (9)O3—Ag1—Ag2—N2120.29 (19)
C14—C10—C11—C12179.1 (6)O3—Ag1—Ag2—O439.7 (2)
C15—C16—C17—C18176.4 (6)O3—Ag1—Ag2—O5i159.3 (2)
C15—C16—C21—C20177.3 (7)O3—Ag1—Ag2—O6i116.2 (2)
C15—N1—N2—Ag2179.8 (3)O3—Ag1—N1—C15132.3 (5)
C15—N1—N2—C141.7 (6)O3—Ag1—N1—N227.6 (4)
C16—C15—N1—Ag120.1 (9)O3—C24—O5—Ag2i34.0 (10)
C16—C15—N1—N2177.9 (5)O4—Ag2—N2—C1443.9 (7)
C16—C15—O1—C14178.6 (5)O4—Ag2—N2—N1132.8 (3)
C16—C17—C18—C190.1 (10)O4—C25—C26—F170.3 (12)
C17—C16—C21—C200.3 (11)O4—C25—C26—F2166.6 (13)
C17—C18—C19—C201.7 (10)O4—C25—C26—F341.2 (15)
C17—C18—C19—C22179.1 (7)O4—C25—O6—Ag2i17.5 (14)
C18—C19—C20—C212.6 (12)O5i—Ag2—N2—C1455.3 (7)
C19—C20—C21—C161.9 (12)O5i—Ag2—N2—N1128.1 (3)
C21—C16—C17—C180.6 (10)O5i—Ag2—O4—C2584.3 (6)
C22—C19—C20—C21178.1 (8)O5—C24—O3—Ag177.9 (11)
C23—C24—O3—Ag1108.5 (7)O6i—Ag2—N2—C14149.6 (7)
C23—C24—O5—Ag2i139.8 (6)O6i—Ag2—N2—N133.8 (4)
C26—C25—O4—Ag2173.2 (6)O6i—Ag2—O4—C2531.9 (10)
C26—C25—O6—Ag2i159.1 (6)O6—C25—C26—F1112.5 (11)
C27ii—C27—Cl1—Cl1ii82 (4)O6—C25—C26—F210.6 (17)
Cl1ii—C27—Cl1—C27ii82 (4)O6—C25—C26—F3136.0 (12)
Cl1—C27—Cl2—C27ii33.2 (19)O6—C25—O4—Ag23.4 (13)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y, z+1/2.
 

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