Syntheses and characterization of dinuclear and tetra­nuclear Ag^I supra­molecular com­plexes generated from symmetric and asymmetric mol­ecular clips containing oxa­diazole rings

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 Ag^I 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.

Computing details

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)

Crystal data

[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) Å^3	0.16 × 0.07 × 0.05 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.1341P)^2 + 0.9025P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0077 (11)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

N4—C9	1.325 (8)	N2—C6	1.280 (8)
N4—Ag1^i	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—N4^i	2.226 (5)	C3—C2	1.385 (10)
Ag1—Ag1^ii	3.0943 (10)	C10—H10	0.9300
Ag1—N1	2.236 (5)	C12—H12	0.9300
Ag1—O2^ii	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—Ag1^ii	2.482 (14)
N3—N2	1.427 (9)	O3'—Ag1^ii	2.42 (2)
N3—C7	1.272 (9)
C9—N4—Ag1^i	120.9 (4)	N2—C6—C4	126.5 (6)
C9—N4—C10	118.2 (6)	N1—C5—H5	118.5
C10—N4—Ag1^i	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)
N4^i—Ag1—Ag1^ii	112.71 (14)	C12—C8—C7	119.8 (6)
N4^i—Ag1—N1	155.8 (2)	C4—C3—H3	120.9
N4^i—Ag1—O2^ii	92.4 (4)	C4—C3—C2	118.1 (6)
N4^i—Ag1—O3	82.1 (3)	C2—C3—H3	120.9
N4^i—Ag1—O3'	88.5 (4)	N4—C10—C11	123.5 (7)
N4^i—Ag1—O3'^ii	121.5 (4)	N4—C10—H10	118.3
N1—Ag1—Ag1^ii	80.06 (13)	C11—C10—H10	118.3
N1—Ag1—O2^ii	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)
O2^ii—Ag1—Ag1^ii	92.4 (3)	C1—C2—H2	120.1
O2^ii—Ag1—O3	152.0 (4)	C3—C2—H2	120.1
O2^ii—Ag1—O3'	137.1 (5)	F1—C14—C13	115.2 (7)
O3—Ag1—Ag1^ii	65.2 (3)	F3—C14—F1	105.0 (10)
O3—Ag1—O3'	16.5 (4)	F3—C14—C13	112.6 (8)
O3'^ii—Ag1—Ag1^ii	57.0 (4)	F2—C14—F1	109.2 (10)
O3'—Ag1—Ag1^ii	48.8 (5)	F2—C14—C13	115.4 (9)
O3'^ii—Ag1—O2^ii	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—Ag1^ii	113.4 (10)
O1—C7—C8	119.6 (5)	C13—O3—Ag1	135.1 (8)
N3—C7—O1	114.0 (6)	Ag1^ii—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'—Ag1^ii	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)
N4^i—Ag1—N1—C1	−155.7 (5)	C14—C13—O2—Ag1^ii	169.7 (7)
N4^i—Ag1—N1—C5	26.9 (8)	C14—C13—O3—Ag1	154.3 (8)
N4^i—Ag1—O3—C13	158.8 (11)	C14—C13—O3'—Ag1	99 (2)
N4^i—Ag1—O3'—Ag1^ii	122.4 (3)	C14—C13—O3'—Ag1^ii	−163.0 (10)
N4^i—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)
Ag1^i—N4—C9—C8	173.7 (4)	F1—C14—C13—O2'	−83.2 (18)
Ag1^i—N4—C10—C11	−172.7 (7)	F3—C14—C13—O2	−166.2 (14)
Ag1^ii—Ag1—N1—C1	79.9 (5)	F3—C14—C13—O3	1.2 (13)
Ag1^ii—Ag1—N1—C5	−97.5 (5)	F3—C14—C13—O3'	−23 (2)
Ag1^ii—Ag1—O3—C13	39.2 (10)	F3—C14—C13—O2'	156.4 (18)
Ag1^ii—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)	O2^ii—Ag1—N1—C1	−9.4 (6)
O1—C6—C4—C5	1.5 (9)	O2^ii—Ag1—N1—C5	173.2 (5)
O1—C6—C4—C3	−176.0 (5)	O2^ii—Ag1—O3—C13	78.7 (14)
N1—Ag1—O3—C13	−42.0 (11)	O2^ii—Ag1—O3'—Ag1^ii	30.5 (8)
N1—Ag1—O3'—Ag1^ii	−81.0 (3)	O2^ii—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'—Ag1^ii	−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'—Ag1^ii	−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—Ag1^ii	3.7 (15)
N3—C7—C8—C12	−4.5 (11)	O3—C13—O3'—Ag1^ii	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'—Ag1^ii	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—Ag1^ii	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—Ag1^ii	−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'—Ag1^ii	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)

Crystal data

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) Å^3	Needle, clear light colourless
Z = 4	0.29 × 0.06 × 0.04 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.239	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1486P)^2 + 0.208P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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(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)

Crystal data

[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) Å^3	Plate, colourless
Z = 4	0.17 × 0.15 × 0.04 mm

Data collection

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

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0938P)^2 + 8.0456P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Ag1—Ag2	3.3419 (7)	C15—O1	1.351 (6)
Ag1—N1	2.186 (4)	C16—C17	1.382 (8)
Ag1—N6^i	2.170 (5)	C16—C21	1.383 (8)
Ag1—O3	2.504 (5)	C17—H17	0.9300
Ag2—Ag2^i	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—O5^i	2.430 (6)	C19—C20	1.366 (10)
Ag2—O6^i	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—C27^ii	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—Cl1^ii	1.34 (3)
C11—H11	0.9300	C27—Cl2	1.69 (3)
C11—C12	1.384 (8)	Cl1—C27^ii	1.34 (3)
C12—H12	0.9300	Cl1—Cl1^ii	2.21 (3)
C12—C13	1.378 (9)	Cl2—C27^ii	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—Ag1^i	2.170 (5)
C15—C16	1.451 (7)	O5—Ag2^i	2.430 (6)
C15—N1	1.296 (6)	O6—Ag2^i	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)
N6^i—Ag1—Ag2	132.79 (13)	C19—C18—H18	119.5
N6^i—Ag1—N1	157.74 (18)	C18—C19—C22	120.6 (7)
N6^i—Ag1—O3	99.4 (2)	C20—C19—C18	117.4 (6)
O3—Ag1—Ag2	51.41 (13)	C20—C19—C22	122.0 (7)
Ag2^i—Ag2—Ag1	100.26 (3)	C19—C20—H20	118.7
N2—Ag2—Ag1	62.62 (10)	C19—C20—C21	122.5 (7)
N2—Ag2—Ag2^i	162.04 (10)	C21—C20—H20	118.7
O4—Ag2—Ag1	122.37 (17)	C16—C21—C20	119.9 (7)
O4—Ag2—Ag2^i	87.57 (14)	C16—C21—H21	120.1
O4—Ag2—N2	97.09 (17)	C20—C21—H21	120.1
O4—Ag2—O5^i	97.0 (2)	C19—C22—H22A	109.5
O4—Ag2—O6^i	159.8 (2)	C19—C22—H22B	109.5
O5^i—Ag2—Ag1	138.86 (16)	C19—C22—H22C	109.5
O5^i—Ag2—Ag2^i	92.11 (13)	H22A—C22—H22B	109.5
O5^i—Ag2—N2	104.44 (17)	H22A—C22—H22C	109.5
O6^i—Ag2—Ag1	55.13 (13)	H22B—C22—H22C	109.5
O6^i—Ag2—Ag2^i	74.07 (14)	F4—C23—C24	110.3 (8)
O6^i—Ag2—N2	98.03 (16)	F5—C23—C24	119.1 (8)
O6^i—Ag2—O5^i	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)	C27^ii—C27—H27A	155.9
N4—C6—O2	112.3 (4)	C27^ii—C27—H27B	92.6
O2—C6—C4	118.7 (4)	C27^ii—C27—Cl1	47.4 (17)
N3—C7—C8	128.8 (5)	C27^ii—C27—Cl2	65.8 (12)
N3—C7—O2	112.1 (5)	H27A—C27—H27B	109.6
O2—C7—C8	119.0 (4)	Cl1^ii—C27—C27^ii	83 (3)
C9—C8—C7	121.2 (5)	Cl1—C27—H27A	113.2
C9—C8—C13	119.8 (5)	Cl1^ii—C27—H27A	113.7
C13—C8—C7	118.9 (5)	Cl1^ii—C27—H27B	23.7
C8—C9—H9	120.1	Cl1—C27—H27B	110.5
C10—C9—C8	119.7 (5)	Cl1^ii—C27—Cl1	88 (2)
C10—C9—H9	120.1	Cl1^ii—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	C27^ii—Cl1—C27	50 (3)
C12—C11—C10	119.7 (6)	C27—Cl1—Cl1^ii	37.2 (11)
C12—C11—H11	120.1	C27^ii—Cl1—Cl1^ii	54.6 (16)
C11—C12—H12	119.8	C27—Cl2—C27^ii	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—Ag1^i	122.8 (4)
N1—C15—O1	111.0 (4)	C5—N6—Ag1^i	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—Ag2^i	111.7 (5)
C18—C17—H17	119.8	C25—O6—Ag2^i	127.2 (5)
Ag1—Ag2—N2—C14	166.8 (8)	Cl1^ii—C27—Cl2—C27^ii	−62 (3)
Ag1—Ag2—N2—N1	−9.9 (3)	Cl2—C27—Cl1—C27^ii	−42.7 (16)
Ag1—Ag2—O4—C25	108.1 (6)	Cl2—C27—Cl1—Cl1^ii	−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)
Ag2^i—Ag2—N2—C14	148.1 (6)	F6—C23—C24—O5	−141.7 (10)
Ag2^i—Ag2—N2—N1	−28.6 (6)	N1—Ag1—Ag2—Ag2^i	−179.31 (13)
Ag2^i—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—Ag1^i	−177.1 (5)	N1—Ag1—Ag2—O5^i	−74.0 (2)
C2—C1—N6—C5	−0.2 (11)	N1—Ag1—Ag2—O6^i	−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—Ag1^i	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)	N6^i—Ag1—Ag2—Ag2^i	−9.1 (2)
C6—C4—C5—N6	179.7 (6)	N6^i—Ag1—Ag2—N2	176.7 (2)
C7—C8—C9—C10	−177.6 (5)	N6^i—Ag1—Ag2—O4	−102.7 (3)
C7—C8—C13—C12	178.4 (6)	N6^i—Ag1—Ag2—O5^i	96.2 (3)
C7—N3—N4—C6	−1.0 (6)	N6^i—Ag1—Ag2—O6^i	53.2 (3)
C8—C7—N3—N4	−177.4 (6)	N6^i—Ag1—N1—C15	27.1 (8)
C8—C7—O2—C6	178.1 (5)	N6^i—Ag1—N1—N2	−172.9 (5)
C8—C9—C10—C11	0.0 (9)	N6^i—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—Ag2^i	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—O5^i	159.3 (2)
C15—C16—C21—C20	177.3 (7)	O3—Ag1—Ag2—O6^i	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—Ag2^i	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—Ag2^i	−17.5 (14)
C18—C19—C20—C21	2.6 (12)	O5^i—Ag2—N2—C14	−55.3 (7)
C19—C20—C21—C16	−1.9 (12)	O5^i—Ag2—N2—N1	128.1 (3)
C21—C16—C17—C18	0.6 (10)	O5^i—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)	O6^i—Ag2—N2—C14	−149.6 (7)
C23—C24—O5—Ag2^i	−139.8 (6)	O6^i—Ag2—N2—N1	33.8 (4)
C26—C25—O4—Ag2	−173.2 (6)	O6^i—Ag2—O4—C25	31.9 (10)
C26—C25—O6—Ag2^i	159.1 (6)	O6—C25—C26—F1	112.5 (11)
C27^ii—C27—Cl1—Cl1^ii	−82 (4)	O6—C25—C26—F2	−10.6 (17)
Cl1^ii—C27—Cl1—C27^ii	82 (4)	O6—C25—C26—F3	−136.0 (12)
Cl1—C27—Cl2—C27^ii	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.