Tetra­kis[μ-1,3-bis­(4,5-dihydro-1,3-oxazol-2-yl)benzene-κ2N:N′]tris­ilver(I) tris­(hexa­fluoridophosphate)

Yeh, C.-W.; Ho, Y.-W.; Lee, H.-T.; Wang, J.-C.; Suen, M.-C.

doi:10.1107/S1600536812034721

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page m1170

doi:10.1107/S1600536812034721

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Tetrakis[μ-1,3-bis(4,5-dihydro-1,3-oxazol-2-yl)benzene-κ²N:N′]trisilver(I) tris(hexafluoridophosphate)

Chun-Wei Yeh,^a Yuh-Wen Ho,^b Hsun-Tsing Lee,^c Ju-Chun Wang ^d and Maw-Cherng Suen ^b ^*

^aDepartment of Chemistry, Chung-Yuan Christian University, Jhongli 32023, Taiwan, ^bDepartment of Creative Fashion Design, Taoyuan Innovation Institute of Technology, Jhongli 32091, Taiwan, ^cDepartment of Materials Science and Engineering, Vanung University, Jhongli 32061, Taiwan, and ^dDepartment of Chemistry, Soochow University, Taipei, Taiwan
^*Correspondence e-mail: sun@tiit.edu.tw

(Received 16 July 2012; accepted 5 August 2012; online 11 August 2012)

In the title compound, [Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃, one Ag^I ion, lying on a twofold rotation axis, is coordinated by four N atoms from four 1,3-bis(4,5-dihydro-1,3-oxazol-2-yl)benzene (L) ligands in a distorted tetrahedral geometry and the other Ag^I ion is coordinated by two N atoms from two L ligands in a bent arrangement [N—Ag—N = 169.03 (17)°]. Two L ligands adopt a syn conformation, while the other two adopt an anti conformation. They bridge adjacent Ag^I ions, forming a trinuclear complex. One of the PF₆⁻ anions is half-occupied, with the P atom located on a twofold rotation axis. The PF₆⁻ anions link the complex molecules via Ag⋯F interactions [2.80 (2) and 2.85 (2) Å] into a polymeric chain along [100].

Related literature

For related structures incorporating the 1,4-bis(4,5-dihydro-2-oxazolyl)benzene ligand, see: Suen et al. (2011 ); Wang et al. (2008 , 2011a ,b ); Yeh et al. (2011 ).

Experimental

Crystal data

[Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃
M_r = 1623.46
Monoclinic, C 2/c
a = 22.7473 (16) Å
b = 11.4521 (19) Å
c = 24.1382 (15) Å
β = 116.014 (7)°
V = 5651.0 (11) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 298 K
0.60 × 0.40 × 0.30 mm

Data collection

Siemens P4 four-circle diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1995 ) T_min = 0.634, T_max = 0.964
5107 measured reflections
4976 independent reflections
3885 reflections with I > 2σ(I)
R_int = 0.020
3 standard reflections every 297 reflections intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.137
S = 1.01
4976 reflections
425 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.81 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N11	2.331 (4)
Ag1—N41	2.418 (5)
Ag2—N31	2.104 (5)
Ag2—N61	2.106 (4)

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812034721/hy2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034721/hy2575Isup2.hkl

checkCIF report

Comment top

Several Ag(I), Cd(II) and Cu(II) complexes containing 1,4-bis(4,5-dihydro-2-oxazolyl)benzene ligands have been reported, which show various dimensional structures (Suen et al., 2011; Wang et al., 2008, 2011a,b; Yeh et al., 2011). In the title trinuclear complex, one Ag^I ion, lying on a twofold axis, is coordinated by four N atoms from four 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (L) ligands in a distorted tetrahedral geometry and the other two are each coordinated by two N atoms from two L ligands in a bent linear arrangement (Fig. 1, Table 1). The Ag···Ag separation in the trimer is 7.473 (1) Å. The L ligands show both syn and anti conformations. The PF₆^- anions link the trinuclear cationic complexes via Ag···F interactions [2.80 (2) and 2.85 (2) Å], forming one-dimensional beaded polymeric chains along [100] (Fig. 2).

Related literature top

For related structures incorporating the 1,4-bis(4,5-dihydro-2-oxazolyl)benzene ligand, see: Suen et al. (2011); Wang et al. (2008, 2011a,b); Yeh et al. (2011).

Experimental top

An aqueous solution (5.0 ml) of AgPF₆ (3.0 mmol) was layered carefully over a methanolic solution (5.0 ml) of 1,3-bis(4,5-dihydro-2-oxazolyl)benzene (4.0 mmol) in a tube and kept it in dark. Colourless crystals were obtained after several weeks. These were washed with methanol and collected in 75.8% yield.

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); data reduction: XSCANS (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) 1-x, y, 1/2-z.]
	Fig. 2. The packing diagram of the title compound, showing the one-dimensional beaded chain formed by Ag···F interactions.

Tetrakis[µ-1,3-bis(4,5-dihydro-1,3-oxazol-2-yl)benzene- κ²N:N']trisilver(I) tris(hexafluoridophosphate) top

Crystal data top

[Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃	F(000) = 3216
M_r = 1623.46	D_x = 1.908 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 36 reflections
a = 22.7473 (16) Å	θ = 4.8–12.5°
b = 11.4521 (19) Å	µ = 1.23 mm⁻¹
c = 24.1382 (15) Å	T = 298 K
β = 116.014 (7)°	Plate, colourless
V = 5651.0 (11) Å³	0.60 × 0.40 × 0.30 mm
Z = 4

Data collection top

Siemens P4 four-circle diffractometer	3885 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = 0→26
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = 0→13
T_min = 0.634, T_max = 0.964	l = −28→25
5107 measured reflections	3 standard reflections every 297 reflections
4976 independent reflections	intensity decay: 2.0%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0628P)² + 34.3783P] where P = (F_o² + 2F_c²)/3
4976 reflections	(Δ/σ)_max < 0.001
425 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

[Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃	V = 5651.0 (11) Å³
M_r = 1623.46	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.7473 (16) Å	µ = 1.23 mm⁻¹
b = 11.4521 (19) Å	T = 298 K
c = 24.1382 (15) Å	0.60 × 0.40 × 0.30 mm
β = 116.014 (7)°

Data collection top

Siemens P4 four-circle diffractometer	3885 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	R_int = 0.020
T_min = 0.634, T_max = 0.964	3 standard reflections every 297 reflections
5107 measured reflections	intensity decay: 2.0%
4976 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0628P)² + 34.3783P] where P = (F_o² + 2F_c²)/3
4976 reflections	Δρ_max = 1.02 e Å⁻³
425 parameters	Δρ_min = −0.81 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	U_iso*/U_eq	Occ. (<1)
Ag1	0.5000	0.06276 (6)	0.2500	0.0564 (2)
Ag2	0.18074 (2)	0.04964 (5)	0.26872 (2)	0.05790 (18)
O11	0.31412 (19)	−0.1417 (4)	0.19947 (19)	0.0637 (11)
O31	0.3068 (2)	−0.0441 (4)	0.45572 (19)	0.0675 (12)
O41	0.3592 (2)	0.2537 (5)	0.08323 (18)	0.0694 (13)
O61	0.14979 (18)	0.1693 (4)	0.09064 (16)	0.0532 (9)
N11	0.4086 (2)	−0.0591 (4)	0.2133 (2)	0.0488 (11)
N31	0.2312 (2)	0.0070 (4)	0.3628 (2)	0.0507 (11)
N41	0.4514 (2)	0.1949 (5)	0.1635 (2)	0.0558 (12)
N61	0.1478 (2)	0.1039 (4)	0.1765 (2)	0.0491 (11)
C11	0.3711 (2)	−0.0898 (5)	0.2366 (3)	0.0458 (12)
C12	0.3785 (3)	−0.0977 (6)	0.1487 (3)	0.0580 (15)
H12A	0.4034	−0.1606	0.1423	0.070*
H12B	0.3753	−0.0337	0.1212	0.070*
C13	0.3111 (3)	−0.1394 (7)	0.1382 (3)	0.0712 (19)
H13A	0.2774	−0.0860	0.1116	0.085*
H13B	0.3021	−0.2166	0.1198	0.085*
C21	0.3827 (3)	−0.0752 (5)	0.3012 (3)	0.0465 (12)
C22	0.3315 (3)	−0.0577 (5)	0.3166 (2)	0.0457 (12)
H22A	0.2888	−0.0556	0.2856	0.055*
C23	0.3426 (3)	−0.0434 (5)	0.3773 (2)	0.0469 (12)
C24	0.4070 (3)	−0.0470 (6)	0.4234 (3)	0.0657 (17)
H24A	0.4155	−0.0356	0.4644	0.079*
C25	0.4578 (3)	−0.0674 (6)	0.4080 (3)	0.0710 (19)
H25A	0.5003	−0.0719	0.4390	0.085*
C26	0.4465 (3)	−0.0810 (6)	0.3481 (3)	0.0639 (17)
H26A	0.4813	−0.0942	0.3384	0.077*
C31	0.2900 (3)	−0.0254 (5)	0.3960 (2)	0.0506 (13)
C32	0.1977 (3)	0.0162 (6)	0.4034 (3)	0.0629 (16)
H32A	0.1619	−0.0390	0.3911	0.075*
H32B	0.1809	0.0944	0.4023	0.075*
C33	0.2505 (4)	−0.0123 (8)	0.4664 (3)	0.080 (2)
H33A	0.2603	0.0549	0.4936	0.096*
H33B	0.2374	−0.0768	0.4846	0.096*
C41	0.3914 (3)	0.2206 (5)	0.1427 (2)	0.0464 (12)
C42	0.4700 (3)	0.2166 (8)	0.1130 (3)	0.081 (2)
H42A	0.4845	0.1450	0.1013	0.098*
H42B	0.5049	0.2738	0.1252	0.098*
C43	0.4086 (3)	0.2623 (8)	0.0603 (3)	0.080 (2)
H43A	0.4142	0.3426	0.0508	0.096*
H43B	0.3968	0.2150	0.0237	0.096*
C51	0.3518 (2)	0.2183 (5)	0.1772 (2)	0.0429 (12)
C52	0.2861 (2)	0.1886 (5)	0.1481 (2)	0.0430 (12)
H52A	0.2663	0.1709	0.1062	0.052*
C53	0.2499 (2)	0.1855 (4)	0.1822 (2)	0.0407 (11)
C54	0.2793 (3)	0.2170 (5)	0.2441 (2)	0.0469 (13)
H54A	0.2550	0.2162	0.2667	0.056*
C55	0.3442 (3)	0.2492 (5)	0.2721 (3)	0.0516 (14)
H55A	0.3635	0.2712	0.3134	0.062*
C56	0.3809 (3)	0.2492 (5)	0.2392 (3)	0.0495 (13)
H56A	0.4249	0.2697	0.2584	0.059*
C61	0.1804 (2)	0.1498 (5)	0.1510 (2)	0.0427 (12)
C62	0.0795 (3)	0.0839 (7)	0.1278 (3)	0.0641 (18)
H62A	0.0479	0.1267	0.1368	0.077*
H62B	0.0684	0.0015	0.1238	0.077*
C63	0.0821 (3)	0.1300 (6)	0.0701 (3)	0.0555 (14)
H63A	0.0713	0.0690	0.0393	0.067*
H63B	0.0518	0.1943	0.0527	0.067*
P1	0.5000	0.4236 (2)	0.7500	0.0619 (6)
F1	0.5316 (14)	0.3242 (15)	0.7277 (12)	0.136 (9)	0.50
F2	0.4658 (10)	0.5162 (10)	0.7741 (9)	0.102 (4)	0.50
F3	0.5624 (8)	0.503 (2)	0.7726 (12)	0.172 (9)	0.50
F4	0.4740 (10)	0.490 (2)	0.6891 (7)	0.151 (6)	0.50
F5	0.5275 (10)	0.3615 (19)	0.8141 (7)	0.135 (5)	0.50
F6	0.4354 (9)	0.3566 (19)	0.7311 (13)	0.156 (8)	0.50
P2	0.12182 (9)	0.19994 (18)	0.52246 (10)	0.0733 (5)
F7	0.0734 (4)	0.1210 (9)	0.4738 (4)	0.231 (5)
F8	0.0936 (4)	0.2993 (9)	0.4800 (5)	0.241 (6)
F9	0.1540 (4)	0.1000 (7)	0.5635 (6)	0.266 (7)
F10	0.0687 (4)	0.2167 (15)	0.5419 (5)	0.290 (8)
F11	0.1701 (3)	0.2775 (6)	0.5752 (3)	0.156 (3)
F12	0.1760 (4)	0.1934 (12)	0.5037 (4)	0.248 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0330 (3)	0.0662 (4)	0.0635 (4)	0.000	0.0150 (3)	0.000
Ag2	0.0457 (3)	0.0879 (4)	0.0438 (3)	0.0038 (2)	0.0231 (2)	0.0128 (2)
O11	0.045 (2)	0.090 (3)	0.059 (2)	−0.027 (2)	0.0255 (19)	−0.016 (2)
O31	0.082 (3)	0.080 (3)	0.041 (2)	0.009 (2)	0.028 (2)	0.010 (2)
O41	0.056 (2)	0.114 (4)	0.048 (2)	0.017 (3)	0.031 (2)	0.018 (2)
O61	0.042 (2)	0.075 (3)	0.042 (2)	0.0003 (19)	0.0179 (16)	0.0088 (19)
N11	0.035 (2)	0.057 (3)	0.057 (3)	−0.008 (2)	0.023 (2)	−0.003 (2)
N31	0.054 (3)	0.059 (3)	0.042 (2)	−0.003 (2)	0.024 (2)	0.004 (2)
N41	0.039 (3)	0.080 (4)	0.056 (3)	0.005 (2)	0.029 (2)	0.011 (2)
N61	0.035 (2)	0.074 (3)	0.043 (2)	0.004 (2)	0.0216 (19)	0.007 (2)
C11	0.036 (3)	0.043 (3)	0.056 (3)	0.000 (2)	0.017 (2)	0.000 (2)
C12	0.048 (3)	0.067 (4)	0.063 (4)	−0.009 (3)	0.029 (3)	−0.009 (3)
C13	0.063 (4)	0.096 (5)	0.057 (4)	−0.026 (4)	0.029 (3)	−0.019 (4)
C21	0.039 (3)	0.046 (3)	0.053 (3)	−0.006 (2)	0.018 (2)	0.001 (2)
C22	0.040 (3)	0.045 (3)	0.044 (3)	−0.003 (2)	0.011 (2)	0.003 (2)
C23	0.043 (3)	0.046 (3)	0.045 (3)	−0.003 (2)	0.013 (2)	0.005 (2)
C24	0.066 (4)	0.074 (4)	0.041 (3)	−0.009 (3)	0.008 (3)	0.005 (3)
C25	0.045 (3)	0.087 (5)	0.059 (4)	−0.003 (3)	0.001 (3)	0.011 (3)
C26	0.037 (3)	0.075 (4)	0.069 (4)	−0.003 (3)	0.014 (3)	0.008 (3)
C31	0.065 (4)	0.047 (3)	0.038 (3)	−0.005 (3)	0.021 (3)	0.002 (2)
C32	0.076 (4)	0.064 (4)	0.064 (4)	0.001 (3)	0.045 (3)	0.005 (3)
C33	0.087 (5)	0.112 (6)	0.050 (4)	−0.007 (5)	0.039 (4)	−0.001 (4)
C41	0.047 (3)	0.051 (3)	0.046 (3)	0.000 (2)	0.024 (2)	0.001 (2)
C42	0.065 (4)	0.126 (7)	0.074 (4)	0.016 (4)	0.050 (4)	0.027 (4)
C43	0.069 (4)	0.128 (7)	0.061 (4)	0.005 (4)	0.046 (4)	0.011 (4)
C51	0.039 (3)	0.048 (3)	0.045 (3)	0.007 (2)	0.021 (2)	0.005 (2)
C52	0.042 (3)	0.050 (3)	0.041 (3)	0.006 (2)	0.021 (2)	0.004 (2)
C53	0.035 (3)	0.045 (3)	0.044 (3)	0.007 (2)	0.019 (2)	0.004 (2)
C54	0.045 (3)	0.059 (3)	0.045 (3)	0.010 (3)	0.027 (2)	0.005 (2)
C55	0.049 (3)	0.065 (4)	0.044 (3)	−0.001 (3)	0.023 (3)	−0.006 (3)
C56	0.039 (3)	0.060 (4)	0.050 (3)	0.003 (3)	0.020 (2)	0.000 (3)
C61	0.040 (3)	0.047 (3)	0.043 (3)	0.008 (2)	0.021 (2)	0.004 (2)
C62	0.035 (3)	0.109 (5)	0.047 (3)	−0.011 (3)	0.017 (2)	0.005 (3)
C63	0.041 (3)	0.071 (4)	0.049 (3)	0.004 (3)	0.015 (2)	0.006 (3)
P1	0.0493 (12)	0.0745 (16)	0.0784 (16)	0.000	0.0431 (12)	0.000
F1	0.21 (3)	0.091 (9)	0.20 (2)	0.038 (14)	0.18 (2)	0.011 (13)
F2	0.124 (13)	0.075 (6)	0.157 (12)	0.029 (8)	0.108 (11)	0.014 (8)
F3	0.071 (9)	0.21 (2)	0.23 (2)	−0.047 (10)	0.064 (13)	−0.034 (19)
F4	0.142 (13)	0.225 (18)	0.118 (11)	0.074 (14)	0.086 (11)	0.076 (12)
F5	0.157 (13)	0.161 (15)	0.105 (9)	0.074 (12)	0.074 (9)	0.066 (10)
F6	0.101 (11)	0.142 (19)	0.25 (3)	−0.054 (11)	0.101 (15)	−0.039 (16)
P2	0.0472 (9)	0.0794 (13)	0.0804 (12)	0.0067 (9)	0.0161 (9)	−0.0022 (10)
F7	0.147 (7)	0.200 (9)	0.208 (9)	−0.008 (6)	−0.048 (6)	−0.083 (7)
F8	0.140 (6)	0.246 (11)	0.283 (12)	0.054 (7)	0.043 (7)	0.168 (10)
F9	0.118 (6)	0.153 (7)	0.368 (14)	−0.043 (5)	−0.041 (7)	0.137 (8)
F10	0.091 (5)	0.61 (2)	0.194 (8)	0.005 (9)	0.086 (6)	−0.080 (12)
F11	0.110 (5)	0.137 (5)	0.166 (6)	−0.005 (4)	0.010 (4)	−0.052 (5)
F12	0.139 (6)	0.457 (18)	0.165 (7)	0.096 (9)	0.082 (6)	−0.042 (9)

Geometric parameters (Å, º) top

Ag1—N11	2.331 (4)	C32—H32A	0.9700
Ag1—N41	2.418 (5)	C32—H32B	0.9700
Ag2—N31	2.104 (5)	C33—H33A	0.9700
Ag2—N61	2.106 (4)	C33—H33B	0.9700
O11—C11	1.348 (6)	C41—C51	1.472 (7)
O11—C13	1.450 (7)	C42—C43	1.511 (10)
O31—C31	1.335 (7)	C42—H42A	0.9700
O31—C33	1.460 (8)	C42—H42B	0.9700
O41—C41	1.348 (7)	C43—H43A	0.9700
O41—C43	1.457 (7)	C43—H43B	0.9700
O61—C61	1.329 (6)	C51—C52	1.387 (7)
O61—C63	1.467 (7)	C51—C56	1.391 (7)
N11—C11	1.260 (7)	C52—C53	1.396 (7)
N11—C12	1.469 (7)	C52—H52A	0.9300
N31—C31	1.276 (8)	C53—C54	1.391 (7)
N31—C32	1.485 (7)	C53—C61	1.479 (7)
N41—C41	1.264 (7)	C54—C55	1.378 (8)
N41—C42	1.478 (7)	C54—H54A	0.9300
N61—C61	1.269 (7)	C55—C56	1.382 (7)
N61—C62	1.498 (7)	C55—H55A	0.9300
C11—C21	1.474 (8)	C56—H56A	0.9300
C12—C13	1.517 (8)	C62—C63	1.515 (8)
C12—H12A	0.9700	C62—H62A	0.9700
C12—H12B	0.9700	C62—H62B	0.9700
C13—H13A	0.9700	C63—H63A	0.9700
C13—H13B	0.9700	C63—H63B	0.9700
C21—C22	1.384 (8)	P1—F4	1.527 (12)
C21—C26	1.396 (8)	P1—F6	1.539 (16)
C22—C23	1.383 (8)	P1—F1	1.562 (13)
C22—H22A	0.9300	P1—F5	1.564 (11)
C23—C24	1.398 (8)	P1—F3	1.566 (16)
C23—C31	1.469 (8)	P1—F2	1.570 (11)
C24—C25	1.380 (10)	P2—F8	1.476 (8)
C24—H24A	0.9300	P2—F9	1.481 (7)
C25—C26	1.363 (10)	P2—F12	1.488 (8)
C25—H25A	0.9300	P2—F10	1.490 (7)
C26—H26A	0.9300	P2—F7	1.509 (7)
C32—C33	1.504 (10)	P2—F11	1.546 (6)

N11—Ag1—N11ⁱ	106.5 (2)	O61—C63—C62	104.7 (4)
N11—Ag1—N41ⁱ	134.17 (16)	O61—C63—H63A	110.8
N11ⁱ—Ag1—N41ⁱ	93.01 (17)	C62—C63—H63A	110.8
N11—Ag1—N41	93.01 (17)	O61—C63—H63B	110.8
N11ⁱ—Ag1—N41	134.17 (16)	C62—C63—H63B	110.8
N41ⁱ—Ag1—N41	102.5 (3)	H63A—C63—H63B	108.9
N31—Ag2—N61	169.03 (17)	F4ⁱⁱ—P1—F4	120 (2)
C11—O11—C13	105.7 (4)	F4ⁱⁱ—P1—F6	116.9 (11)
C31—O31—C33	107.0 (5)	F4—P1—F6	92.7 (16)
C41—O41—C43	105.9 (5)	F4ⁱⁱ—P1—F6ⁱⁱ	92.7 (16)
C61—O61—C63	106.7 (4)	F4—P1—F6ⁱⁱ	116.9 (11)
C11—N11—C12	107.2 (4)	F6—P1—F6ⁱⁱ	120.2 (18)
C11—N11—Ag1	131.5 (4)	F4ⁱⁱ—P1—F1ⁱⁱ	94.4 (10)
C12—N11—Ag1	120.5 (3)	F6ⁱⁱ—P1—F1ⁱⁱ	93.3 (12)
C31—N31—C32	107.7 (5)	F4ⁱⁱ—P1—F1	130.8 (17)
C31—N31—Ag2	132.2 (4)	F4—P1—F1	94.4 (10)
C32—N31—Ag2	120.1 (4)	F6—P1—F1	93.3 (12)
C41—N41—C42	106.4 (5)	F1ⁱⁱ—P1—F1	86.4 (13)
C41—N41—Ag1	119.6 (4)	F4ⁱⁱ—P1—F5ⁱⁱ	177.0 (16)
C42—N41—Ag1	129.0 (4)	F4—P1—F5ⁱⁱ	57.1 (9)
C61—N61—C62	107.9 (4)	F6—P1—F5ⁱⁱ	64.2 (9)
C61—N61—Ag2	128.5 (4)	F6ⁱⁱ—P1—F5ⁱⁱ	89.0 (10)
C62—N61—Ag2	123.4 (3)	F1ⁱⁱ—P1—F5ⁱⁱ	88.0 (11)
N11—C11—O11	118.0 (5)	F1—P1—F5ⁱⁱ	51.1 (9)
N11—C11—C21	126.8 (5)	F4ⁱⁱ—P1—F5	57.1 (9)
O11—C11—C21	115.2 (5)	F4—P1—F5	177.0 (17)
N11—C12—C13	103.9 (5)	F6—P1—F5	89.0 (10)
N11—C12—H12A	111.0	F6ⁱⁱ—P1—F5	64.2 (9)
C13—C12—H12A	111.0	F1ⁱⁱ—P1—F5	51.1 (9)
N11—C12—H12B	111.0	F1—P1—F5	88.0 (11)
C13—C12—H12B	111.0	F5ⁱⁱ—P1—F5	125.9 (18)
H12A—C12—H12B	109.0	F4ⁱⁱ—P1—F3	57.7 (9)
O11—C13—C12	104.0 (5)	F4—P1—F3	87.4 (11)
O11—C13—H13A	111.0	F6—P1—F3	173.3 (12)
C12—C13—H13A	111.0	F6ⁱⁱ—P1—F3	65.4 (11)
O11—C13—H13B	111.0	F1ⁱⁱ—P1—F3	141.7 (17)
C12—C13—H13B	111.0	F1—P1—F3	93.3 (12)
H13A—C13—H13B	109.0	F5ⁱⁱ—P1—F3	121.0 (10)
C22—C21—C26	119.2 (6)	F5—P1—F3	90.6 (16)
C22—C21—C11	121.3 (5)	F4ⁱⁱ—P1—F3ⁱⁱ	87.4 (11)
C26—C21—C11	119.5 (5)	F4—P1—F3ⁱⁱ	57.7 (9)
C23—C22—C21	121.1 (5)	F6—P1—F3ⁱⁱ	65.4 (11)
C23—C22—H22A	119.4	F6ⁱⁱ—P1—F3ⁱⁱ	173.3 (12)
C21—C22—H22A	119.4	F1ⁱⁱ—P1—F3ⁱⁱ	93.3 (12)
C22—C23—C24	118.8 (6)	F1—P1—F3ⁱⁱ	141.7 (17)
C22—C23—C31	123.2 (5)	F5ⁱⁱ—P1—F3ⁱⁱ	90.6 (16)
C24—C23—C31	118.0 (5)	F5—P1—F3ⁱⁱ	121.0 (10)
C25—C24—C23	119.9 (6)	F3—P1—F3ⁱⁱ	109.4 (18)
C25—C24—H24A	120.0	F4ⁱⁱ—P1—F2	49.6 (8)
C23—C24—H24A	120.0	F4—P1—F2	88.4 (9)
C26—C25—C24	121.0 (6)	F6—P1—F2	83.2 (11)
C26—C25—H25A	119.5	F6ⁱⁱ—P1—F2	142.3 (15)
C24—C25—H25A	119.5	F1ⁱⁱ—P1—F2	89.3 (8)
C25—C26—C21	119.9 (6)	F1—P1—F2	175.7 (8)
C25—C26—H26A	120.0	F5ⁱⁱ—P1—F2	128.7 (14)
C21—C26—H26A	120.0	F5—P1—F2	89.3 (8)
N31—C31—O31	116.8 (5)	F3—P1—F2	90.1 (9)
N31—C31—C23	128.2 (5)	F4ⁱⁱ—P1—F2ⁱⁱ	88.4 (9)
O31—C31—C23	115.0 (5)	F4—P1—F2ⁱⁱ	49.6 (8)
N31—C32—C33	103.9 (5)	F6—P1—F2ⁱⁱ	142.3 (15)
N31—C32—H32A	111.0	F6ⁱⁱ—P1—F2ⁱⁱ	83.2 (11)
C33—C32—H32A	111.0	F1ⁱⁱ—P1—F2ⁱⁱ	175.7 (8)
N31—C32—H32B	111.0	F1—P1—F2ⁱⁱ	89.3 (8)
C33—C32—H32B	111.0	F5ⁱⁱ—P1—F2ⁱⁱ	89.3 (8)
H32A—C32—H32B	109.0	F5—P1—F2ⁱⁱ	128.7 (14)
O31—C33—C32	104.3 (5)	F3ⁱⁱ—P1—F2ⁱⁱ	90.1 (9)
O31—C33—H33A	110.9	F2—P1—F2ⁱⁱ	95.1 (9)
C32—C33—H33A	110.9	F6ⁱⁱ—F1—F5ⁱⁱ	133 (2)
O31—C33—H33B	110.9	F6ⁱⁱ—F1—P1	69.6 (14)
C32—C33—H33B	110.9	F5ⁱⁱ—F1—P1	64.5 (9)
H33A—C33—H33B	108.9	F3ⁱⁱ—F2—F4ⁱⁱ	132.4 (16)
N41—C41—O41	118.5 (5)	F3ⁱⁱ—F2—P1	70.6 (13)
N41—C41—C51	126.3 (5)	F4ⁱⁱ—F2—P1	63.5 (8)
O41—C41—C51	115.2 (5)	F2ⁱⁱ—F3—F4ⁱⁱ	116.2 (18)
N41—C42—C43	105.0 (5)	F2ⁱⁱ—F3—P1	70.9 (11)
N41—C42—H42A	110.8	F4ⁱⁱ—F3—P1	59.8 (8)
C43—C42—H42A	110.8	F2ⁱⁱ—F3—F6ⁱⁱ	96 (2)
N41—C42—H42B	110.8	F4ⁱⁱ—F3—F6ⁱⁱ	89 (2)
C43—C42—H42B	110.8	P1—F3—F6ⁱⁱ	56.5 (9)
H42A—C42—H42B	108.8	F2ⁱⁱ—F4—F5ⁱⁱ	104.8 (12)
O41—C43—C42	103.9 (5)	F2ⁱⁱ—F4—F3ⁱⁱ	105.1 (17)
O41—C43—H43A	111.0	F5ⁱⁱ—F4—F3ⁱⁱ	97.0 (18)
C42—C43—H43A	111.0	F2ⁱⁱ—F4—P1	66.9 (8)
O41—C43—H43B	111.0	F5ⁱⁱ—F4—P1	62.7 (7)
C42—C43—H43B	111.0	F3ⁱⁱ—F4—P1	62.5 (8)
H43A—C43—H43B	109.0	F1ⁱⁱ—F5—F4ⁱⁱ	106.5 (13)
C52—C51—C56	120.5 (5)	F1ⁱⁱ—F5—P1	64.4 (8)
C52—C51—C41	120.6 (5)	F4ⁱⁱ—F5—P1	60.2 (7)
C56—C51—C41	118.9 (5)	F1ⁱⁱ—F5—F6ⁱⁱ	97.1 (15)
C51—C52—C53	119.3 (5)	F4ⁱⁱ—F5—F6ⁱⁱ	90.2 (15)
C51—C52—H52A	120.3	P1—F5—F6ⁱⁱ	57.2 (7)
C53—C52—H52A	120.3	F1ⁱⁱ—F6—P1	72.1 (15)
C54—C53—C52	119.8 (5)	F1ⁱⁱ—F6—F5ⁱⁱ	107 (2)
C54—C53—C61	121.4 (4)	P1—F6—F5ⁱⁱ	58.6 (7)
C52—C53—C61	118.8 (5)	F1ⁱⁱ—F6—F3ⁱⁱ	113 (3)
C55—C54—C53	120.3 (5)	P1—F6—F3ⁱⁱ	58.1 (8)
C55—C54—H54A	119.9	F5ⁱⁱ—F6—F3ⁱⁱ	84.0 (17)
C53—C54—H54A	119.9	F8—P2—F9	175.8 (7)
C54—C55—C56	120.3 (5)	F8—P2—F12	89.7 (6)
C54—C55—H55A	119.8	F9—P2—F12	86.1 (7)
C56—C55—H55A	119.8	F8—P2—F10	87.3 (7)
C55—C56—C51	119.7 (5)	F9—P2—F10	96.8 (8)
C55—C56—H56A	120.1	F12—P2—F10	175.4 (9)
C51—C56—H56A	120.1	F8—P2—F7	88.6 (6)
N61—C61—O61	117.7 (5)	F9—P2—F7	92.0 (6)
N61—C61—C53	126.2 (5)	F12—P2—F7	98.8 (6)
O61—C61—C53	116.1 (4)	F10—P2—F7	84.6 (6)
N61—C62—C63	103.0 (4)	F8—P2—F11	93.7 (6)
N61—C62—H62A	111.2	F9—P2—F11	85.9 (5)
C63—C62—H62A	111.2	F12—P2—F11	84.0 (5)
N61—C62—H62B	111.2	F10—P2—F11	92.8 (6)
C63—C62—H62B	111.2	F7—P2—F11	176.4 (6)
H62A—C62—H62B	109.1

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ag₃(C₁₂H₁₂N₂O₂)₄](PF₆)₃
M_r	1623.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	22.7473 (16), 11.4521 (19), 24.1382 (15)
β (°)	116.014 (7)
V (Å³)	5651.0 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.60 × 0.40 × 0.30

Data collection
Diffractometer	Siemens P4 four-circle diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1995)
T_min, T_max	0.634, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	5107, 4976, 3885
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.137, 1.01
No. of reflections	4976
No. of parameters	425
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0628P)² + 34.3783P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.81

Computer programs: XSCANS (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N11	2.331 (4)	Ag2—N31	2.104 (5)
Ag1—N41	2.418 (5)	Ag2—N61	2.106 (4)

Acknowledgements

We are grateful to the National Science Council of the Republic of China and the Taoyuan Innovation Institute of Technology for support.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
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