catena-Poly­[[silver(I)-μ-{bis­[4-(2-pyridyl­methyl­ene­amino)­phenyl] ether}] tri­fluoro­methane­sulfonate 0.4-hydrate]: a zigzag coordination polymer

The title compound, [Ag(C₂₄H₁₈N₄O)]CF₃SO₃·0.4H₂O, can be described as a zigzag polymer. The Ag atom is coordinated to the N atoms of two pyridyl­imine units resulting in a distorted tetrahedral coordination geometry. Both the Ag atom and the central O atom of the ligand are situated on mutually perpendicular crystallographic twofold axes.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.009 Å
• H-atom completeness 96%
• Disorder in solvent or counterion
• R factor = 0.042
• wR factor = 0.095
• Data-to-parameter ratio = 12.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



RINTA_01  Alert B The value of Rint is greater than 0.15
          Rint given   0.180

Author response: The Rint value of 0.18 is due to the poor quality of the crystal, which did not diffract significantly above 40\% in 2\q, and the low I/\s(I) ratio obtained. The ratio of parameters to observed data is at the lower end of the scale, ca. 5, but the s.u.s. are reasonable. This is also responsable for the GOF value which is slightly less than 0.8.

 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.740

PLAT_302  Alert C Anion/Solvent disorder .......................      46.00 Perc.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     62
                   O12 -S1  -O12 -O11  -141.00100.00   5.776   1.555   1.555   5.776

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C25 H18.8 Ag1 F3 N4 O4.4 S1
          Atom count from the _atom_site data:  C25 H18 Ag1 F3 N4 O4.4 S1

CELLZ_01
         From the CIF: _cell_formula_units_Z    4
         From the CIF: _chemical_formula_sum  C25 H18.80 Ag F3 N4 O4.40 S
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C        100.00    100.00    0.00
         H         75.20     72.00    3.20
         Ag         4.00      4.00    0.00
         F         12.00     12.00    0.00
         N         16.00     16.00    0.00
         O         17.60     17.60    0.00
         S          4.00      4.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

S1. Comment

The reaction of the ligand bis[4-(2-pyridilmethyleneamino)phenyl] ether, L1, with Ag(CF₃SO₃) yielded an ionic complex, AgL1, consisting of a one-dimensional zigzag coordination polymer, Fig. 1. Similar single-stranded silver polymers have been reported previously (Bowyer et al., 1998; Carlucci et al., 1998; Suzuki et al., 1995; Withersby et al., 1997). Using L1 and AgNO₃ very small poor crystals of a similar zigzag polymer have also been prepared (Tesouro Vallina & Stoeckli-Evans, 1999a). Using BF₄^- as counter-ion Cheng et al. (2000) have recently published the structure of a silver(I) double-stranded helix, previously postulated by Hannon et al. (1999) and Yoshida et al. (2000), for a similar ligand where the central ether linkage is replaced by a CH₂ group. In AgL1, the Ag—N_py and Ag—N_im bond distances, 2.283 (4) and 2.343 (4) Å, respectively, are similar to those observed in the above-mentioned complexes. The chelate bite angle of 72.69 (16)° is also within the expected range. The ligand is twisted about the central O atom with the two benzene rings being inclined by 51.09 (2)°. The two halves of the ligand (related by a twofold axis) are fairly planar which contrasts with the structure of the ligand itself, where one half of the ligand is much less planar than the other (Tesouro Vallina et al., 2001). The best plane through atoms N1, C1—C6, N2, C7—C12 is planar to within 0.055 (5) Å and the Ag atom is displaced from this plane by 0.227 (5) Å. In the crystal, the chains stack up the c axis with a π–π overlap of symmetry-related aromatic rings; the shortest intermolecular C.·C distance is ca 3.52 (2) Å, Fig. 2.

Despite the polymeric nature of the title compound in the solid state, positive ESI-MS (electrospray ionization mass spectroscopy) in acetonitrile indicates that the most abundant ion in solution is [Ag₂L₂]²⁺ at m/z 486, which corresponds to a binuclear complex, probably the double helix.

S2. Experimental

The synthesis of bis(4-(2-pyridilmethyleneamino)phenyl)ether, L1, has been reported elsewhere (Cheng et al., 2000; Tesouro Vallina et al., 1999b). A methanolic solution of AgCF₃SO₃ (1 equivalent, 0.1 mmol, 0.0257 g per 15 ml) was added slowly to a methanolic solution of L1 (1 equivalent, 0.1 mmol, 0.0378 g per 10 ml) under N₂ and protected from the light. The colour of the mixture changed to deep yellow and a precipitate appeared. The mixture was heated to ca 313 K with stirring for 2 h, cooled to room temperature and filtered. The yellow solid obtained was dissolved in acetonitrile and left undisturbed in the dark for ca two weeks, whereupon yellow–green crystals were formed. IR (KBr pellet, cm^-1): 3468, 3067 (C—H), 1626, 1592, 1561, 1496, 1441, 1420 (C═C, C═N), 1251 (Ph—O), 1056, 1029, 1008, 837, 775 (CF₃). Analysis for [AgL][CF₃SO₃]·2H₂O (623.41 g mol^-1), calculated: C 48.17, H 3.71, N 8.98%; found: C 48.43, H 3.36, N 8.20%. MS (ESI) m/z: 1121, [Ag₂L₂CF₃SO₃]⁺; 865, [AgL₂]⁺; 742, [Ag₂LCF₃SO₃]⁺ and 486, [Ag₂L₂]²⁺. UV/Vis (λ_max/nm, ethanol solution): 330, 390. ¹H NMR (DMSO-d⁶): 7.09 (4H, d, Ph), 7.50 (4H, d, Ph), 7.70 (2H, m, py), 8.13 (4H, dd, py), 8.78 (2H, d, py), 8.89 (2H, s, C═N).

S3. Refinement

The CF₃SO₃^- anion was disordered about a center of symmetry. The H atoms were included in calculated positions and treated as riding atoms using SHELXL default parameters. The H atoms of the partially occupied water molecule could not be located. The R_int value of 0.18 is due to the poor quality of the crystal, which did not diffract significantly above 40° in 2θ, and the low I/σ(I) ratio obtained. The ratio of parameters to observed data is at the lower end of the scale, ca 5, but the s.u.'s. are reasonable. This is also responsable for the GOF value which is slightly less than 0.8.

Computing details

Data collection: EXPOSE (Stoe & Cie, 1997); cell refinement: CELL (Stoe & Cie, 1997); data reduction: INTEGRATE (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON99 (Spek, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. View of the title compound showing the numbering scheme and displacement ellipsoids at 50% probability level. The disordered CF3SO3^- anion and partially occupied water molecule have been omitted for clarity.
	Fig. 2. Crystal packing of (I) showing the π–π interactions. The H atoms and the disordered CF3SO3^- anion and partially occupied water molecule have been omitted for clarity.

(I)

Crystal data

[Ag(C24H18N4O)]CF3SO3·0.4H2O	Dx = 1.603 Mg m^−3
Mr = 642.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pcca	Cell parameters from 5109 reflections
a = 15.3582 (15) Å	θ = 2.6–25.9°
b = 11.6957 (12) Å	µ = 0.90 mm^−1
c = 14.8253 (12) Å	T = 153 K
V = 2663.0 (4) Å^3	Block, pale yellow
Z = 4	0.25 × 0.10 × 0.05 mm
F(000) = 1288

Data collection

STOE IPDS diffractometer	1105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.180
Graphite monochromator	θmax = 25.9°, θmin = 2.6°
Detector resolution: 0.81 pixels mm^-1	h = −18→18
ϕ oscillation scans	k = −14→14
19496 measured reflections	l = −18→18
2588 independent 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = /[σ^2(Fo^2) + (0.04P)^2] where P = Fo^2 + 2Fc^2)/3
S = 0.74	(Δ/σ)max < 0.001
2588 reflections	Δρmax = 0.59 e Å^−3
212 parameters	Δρmin = −0.68 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=Fc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	0.7500	0.5000	0.64168 (3)	0.0382 (2)
N1	0.7594 (4)	0.6742 (4)	0.7105 (2)	0.0338 (11)
N2	0.8527 (3)	0.6080 (4)	0.5617 (3)	0.0287 (10)
O1	1.0000	0.4247 (5)	0.2500	0.0415 (15)
C1	0.7181 (3)	0.7080 (6)	0.7858 (4)	0.0447 (17)
H1A	0.6717	0.6624	0.8083	0.054*
C2	0.7404 (5)	0.8069 (6)	0.8319 (4)	0.0549 (17)
H2A	0.7081	0.8293	0.8836	0.066*
C3	0.8096 (5)	0.8731 (6)	0.8029 (5)	0.069 (2)
H3A	0.8273	0.9390	0.8356	0.082*
C4	0.8533 (4)	0.8399 (6)	0.7234 (5)	0.0575 (19)
H4A	0.9002	0.8838	0.7000	0.069*
C5	0.8251 (4)	0.7397 (5)	0.6799 (4)	0.0389 (15)
C6	0.8706 (3)	0.7018 (5)	0.5974 (4)	0.0392 (14)
H6A	0.9140	0.7493	0.5712	0.047*
C7	0.8942 (3)	0.5692 (6)	0.4806 (4)	0.0307 (15)
C8	0.9567 (3)	0.6326 (5)	0.4334 (3)	0.0319 (14)
H8A	0.9743	0.7055	0.4548	0.038*
C9	0.9928 (3)	0.5880 (5)	0.3548 (4)	0.0343 (13)
H9A	1.0355	0.6299	0.3223	0.041*
C10	0.9657 (3)	0.4827 (7)	0.3251 (3)	0.0339 (17)
C11	0.9037 (3)	0.4185 (5)	0.3715 (3)	0.0352 (14)
H11A	0.8853	0.3460	0.3497	0.042*
C12	0.8697 (3)	0.4636 (5)	0.4503 (4)	0.0334 (17)
H12A	0.8286	0.4203	0.4839	0.040*
S1	1.0000	1.0000	0.5000	0.0868 (8)
O11	1.0041 (8)	0.8998 (9)	0.5497 (9)	0.072 (4)	0.50
O12	1.0658 (7)	1.0826 (12)	0.5313 (10)	0.102 (4)	0.50
O13	1.0113 (9)	0.992 (3)	0.5894 (6)	0.135 (5)	0.50
C13	0.8949 (12)	1.0804 (15)	0.5496 (16)	0.092 (6)	0.50
F11	0.8997 (8)	1.0975 (12)	0.6330 (7)	0.134 (5)	0.50
F12	0.8792 (8)	1.1742 (10)	0.5092 (8)	0.122 (4)	0.50
F13	0.8285 (7)	1.0104 (14)	0.5319 (9)	0.144 (4)	0.50
O1W	1.0000	1.138 (3)	0.7500	0.165 (12)	0.40

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0413 (3)	0.0496 (4)	0.0237 (3)	−0.0154 (5)	0.000	0.000
N1	0.033 (3)	0.043 (3)	0.026 (2)	−0.008 (3)	0.001 (3)	−0.0021 (19)
N2	0.033 (2)	0.038 (3)	0.015 (2)	0.000 (2)	−0.0015 (18)	−0.001 (2)
O1	0.039 (3)	0.066 (4)	0.019 (3)	0.000	0.009 (2)	0.000
C1	0.039 (3)	0.066 (5)	0.029 (3)	−0.003 (3)	0.006 (2)	−0.002 (3)
C2	0.054 (4)	0.063 (4)	0.048 (4)	−0.006 (4)	0.019 (4)	−0.016 (3)
C3	0.077 (5)	0.058 (5)	0.071 (5)	−0.017 (4)	0.025 (4)	−0.032 (4)
C4	0.058 (4)	0.045 (4)	0.069 (5)	−0.013 (4)	0.028 (3)	−0.022 (4)
C5	0.045 (4)	0.040 (4)	0.032 (3)	0.001 (3)	0.012 (3)	−0.002 (3)
C6	0.045 (3)	0.041 (4)	0.032 (3)	−0.003 (3)	0.017 (3)	0.003 (3)
C7	0.025 (3)	0.048 (4)	0.019 (3)	−0.002 (3)	0.002 (2)	0.004 (3)
C8	0.032 (3)	0.047 (4)	0.016 (3)	−0.002 (3)	−0.006 (2)	0.006 (3)
C9	0.027 (3)	0.058 (4)	0.018 (3)	−0.006 (3)	0.004 (3)	0.004 (3)
C10	0.027 (2)	0.060 (6)	0.015 (2)	0.008 (3)	0.0011 (18)	−0.008 (4)
C11	0.028 (3)	0.052 (4)	0.026 (4)	−0.001 (3)	−0.001 (2)	0.000 (3)
C12	0.029 (3)	0.051 (5)	0.020 (3)	−0.007 (3)	0.008 (2)	−0.001 (3)
S1	0.131 (2)	0.067 (2)	0.0629 (18)	−0.025 (3)	−0.0046 (15)	0.008 (3)
O11	0.087 (8)	0.027 (6)	0.102 (10)	−0.019 (6)	0.017 (7)	0.014 (6)
O12	0.081 (9)	0.092 (10)	0.134 (12)	−0.047 (7)	0.016 (8)	−0.028 (9)
O13	0.141 (10)	0.220 (19)	0.043 (7)	0.012 (19)	−0.004 (6)	0.010 (17)
C13	0.094 (14)	0.060 (12)	0.123 (18)	−0.050 (11)	−0.019 (12)	0.033 (13)
F11	0.177 (11)	0.164 (12)	0.061 (7)	0.058 (9)	0.043 (7)	−0.006 (7)
F12	0.184 (12)	0.061 (7)	0.121 (9)	0.008 (7)	−0.056 (8)	0.031 (7)
F13	0.109 (7)	0.097 (9)	0.227 (12)	−0.012 (10)	−0.027 (7)	0.021 (13)
O1W	0.26 (3)	0.15 (3)	0.076 (16)	0.000	0.077 (19)	0.000

Geometric parameters (Å, º)

Ag1—N1	2.283 (4)	C9—C10	1.373 (9)
Ag1—N1^i	2.283 (4)	C10—C11	1.395 (8)
Ag1—N2^i	2.343 (4)	C11—C12	1.383 (7)
Ag1—N2	2.343 (4)	S1—O13^iii	1.340 (10)
N1—C1	1.344 (7)	S1—O13	1.340 (10)
N1—C5	1.345 (7)	S1—O11	1.385 (11)
N2—C6	1.249 (7)	S1—O11^iii	1.385 (11)
N2—C7	1.435 (7)	S1—O12^iii	1.473 (11)
O1—C10	1.406 (6)	S1—O12	1.473 (11)
O1—C10^ii	1.406 (6)	S1—C13^iii	2.01 (2)
C1—C2	1.386 (8)	S1—C13	2.01 (2)
C2—C3	1.383 (9)	O11—O13	1.23 (2)
C3—C4	1.410 (9)	O11—O12^iii	1.624 (17)
C4—C5	1.406 (9)	O12—O13	1.60 (2)
C5—C6	1.477 (8)	O12—O11^iii	1.624 (17)
C7—C12	1.368 (8)	C13—F11	1.25 (2)
C7—C8	1.400 (7)	C13—F12	1.273 (19)
C8—C9	1.391 (7)	C13—F13	1.333 (18)
N1—Ag1—N1^i	126.9 (2)	O13^iii—S1—O12^iii	69.2 (11)
N1—Ag1—N2^i	138.59 (17)	O13—S1—O12^iii	110.8 (11)
N1^i—Ag1—N2^i	72.69 (16)	O11—S1—O12^iii	69.2 (7)
N1—Ag1—N2	72.69 (16)	O11^iii—S1—O12^iii	110.8 (7)
N1^i—Ag1—N2	138.59 (17)	O13^iii—S1—O12	110.8 (11)
N2^i—Ag1—N2	119.2 (2)	O13—S1—O12	69.2 (11)
C1—N1—C5	117.8 (5)	O11—S1—O12	110.8 (7)
C1—N1—Ag1	127.2 (4)	O11^iii—S1—O12	69.2 (7)
C5—N1—Ag1	113.9 (4)	O12^iii—S1—O12	180.000 (2)
C6—N2—C7	122.3 (5)	O13^iii—S1—C13^iii	77.0 (9)
C6—N2—Ag1	114.1 (3)	O13—S1—C13^iii	103.0 (9)
C7—N2—Ag1	123.6 (4)	O11—S1—C13^iii	76.3 (7)
C10—O1—C10^ii	122.3 (7)	O11^iii—S1—C13^iii	103.7 (7)
N1—C1—C2	122.6 (6)	O12^iii—S1—C13^iii	97.4 (7)
C3—C2—C1	120.2 (6)	O12—S1—C13^iii	82.6 (7)
C2—C3—C4	118.1 (6)	O13^iii—S1—C13	103.0 (9)
C5—C4—C3	117.7 (6)	O13—S1—C13	77.0 (9)
N1—C5—C4	123.5 (5)	O11—S1—C13	103.7 (7)
N1—C5—C6	117.6 (5)	O11^iii—S1—C13	76.3 (7)
C4—C5—C6	118.9 (5)	O12^iii—S1—C13	82.6 (7)
N2—C6—C5	120.7 (5)	O12—S1—C13	97.4 (7)
C12—C7—C8	120.1 (5)	C13^iii—S1—C13	180.000 (3)
C12—C7—N2	116.0 (5)	O13—O11—S1	61.3 (8)
C8—C7—N2	123.8 (5)	O13—O11—O12^iii	107.7 (12)
C9—C8—C7	119.6 (6)	S1—O11—O12^iii	58.0 (6)
C10—C9—C8	119.0 (5)	S1—O12—O13	51.5 (6)
C9—C10—C11	122.1 (5)	S1—O12—O11^iii	52.9 (5)
C9—C10—O1	125.0 (5)	O13—O12—O11^iii	97.8 (8)
C11—C10—O1	112.7 (6)	O11—O13—S1	65.0 (9)
C12—C11—C10	118.0 (6)	O11—O13—O12	111.7 (11)
C7—C12—C11	121.2 (5)	S1—O13—O12	59.3 (8)
O13^iii—S1—O13	180.000 (5)	F11—C13—F12	109.7 (19)
O13^iii—S1—O11	126.3 (11)	F11—C13—F13	109.7 (17)
O13—S1—O11	53.7 (11)	F12—C13—F13	106.9 (16)
O13^iii—S1—O11^iii	53.7 (11)	F11—C13—S1	112.8 (13)
O13—S1—O11^iii	126.3 (11)	F12—C13—S1	112.5 (14)
O11—S1—O11^iii	180.0 (10)	F13—C13—S1	104.8 (14)
N1^i—Ag1—N1—C1	−38.2 (4)	O13^iii—S1—O11—O12^iii	−41.4 (12)
N2^i—Ag1—N1—C1	68.6 (5)	O13—S1—O11—O12^iii	138.6 (12)
N2—Ag1—N1—C1	−176.6 (5)	O12—S1—O11—O12^iii	180.000 (3)
N1^i—Ag1—N1—C5	129.3 (4)	C13^iii—S1—O11—O12^iii	−103.6 (8)
N2^i—Ag1—N1—C5	−123.9 (4)	C13—S1—O11—O12^iii	76.4 (8)
N2—Ag1—N1—C5	−9.1 (4)	O13^iii—S1—O12—O13	180.000 (3)
N1—Ag1—N2—C6	6.6 (4)	O11—S1—O12—O13	−34.7 (11)
N1^i—Ag1—N2—C6	−120.1 (4)	O11^iii—S1—O12—O13	145.3 (11)
N2^i—Ag1—N2—C6	143.1 (4)	C13^iii—S1—O12—O13	−106.9 (11)
N1—Ag1—N2—C7	−175.6 (4)	C13—S1—O12—O13	73.1 (11)
N1^i—Ag1—N2—C7	57.8 (4)	O13^iii—S1—O12—O11^iii	34.7 (11)
N2^i—Ag1—N2—C7	−39.0 (3)	O13—S1—O12—O11^iii	−145.3 (11)
C5—N1—C1—C2	0.2 (9)	O11—S1—O12—O11^iii	180.000 (3)
Ag1—N1—C1—C2	167.3 (5)	O12^iii—S1—O12—O11^iii	−141 (100)
N1—C1—C2—C3	−2.4 (10)	C13^iii—S1—O12—O11^iii	107.8 (8)
C1—C2—C3—C4	3.0 (11)	C13—S1—O12—O11^iii	−72.2 (8)
C2—C3—C4—C5	−1.7 (11)	O12^iii—O11—O13—S1	−36.0 (9)
C1—N1—C5—C4	1.2 (9)	S1—O11—O13—O12	−37.7 (10)
Ag1—N1—C5—C4	−167.6 (5)	O12^iii—O11—O13—O12	−73.7 (14)
C1—N1—C5—C6	179.7 (5)	O11^iii—S1—O13—O11	180.000 (8)
Ag1—N1—C5—C6	10.9 (6)	O12^iii—S1—O13—O11	41.4 (12)
C3—C4—C5—N1	−0.4 (10)	O12—S1—O13—O11	−138.6 (12)
C3—C4—C5—C6	−178.9 (6)	C13^iii—S1—O13—O11	−61.9 (10)
C7—N2—C6—C5	178.7 (5)	C13—S1—O13—O11	118.1 (10)
Ag1—N2—C6—C5	−3.3 (7)	O11—S1—O13—O12	138.6 (12)
N1—C5—C6—N2	−5.2 (8)	O11^iii—S1—O13—O12	−41.4 (12)
C4—C5—C6—N2	173.4 (6)	O12^iii—S1—O13—O12	180.000 (4)
C6—N2—C7—C12	178.5 (5)	C13^iii—S1—O13—O12	76.8 (9)
Ag1—N2—C7—C12	0.8 (6)	C13—S1—O13—O12	−103.2 (9)
C6—N2—C7—C8	−1.2 (8)	S1—O12—O13—O11	40.1 (10)
Ag1—N2—C7—C8	−178.9 (4)	O11^iii—O12—O13—O11	67.4 (16)
C12—C7—C8—C9	0.8 (8)	O11^iii—O12—O13—S1	27.3 (8)
N2—C7—C8—C9	−179.5 (5)	O13—S1—C13—F11	10.2 (17)
C7—C8—C9—C10	0.4 (7)	O11—S1—C13—F11	57.3 (14)
C8—C9—C10—C11	−0.5 (8)	O11^iii—S1—C13—F11	−122.7 (14)
C8—C9—C10—O1	−176.2 (4)	O12^iii—S1—C13—F11	123.6 (14)
C10^ii—O1—C10—C9	−30.1 (4)	O12—S1—C13—F11	−56.4 (14)
C10^ii—O1—C10—C11	153.8 (5)	O13—S1—C13—F12	135.1 (18)
C9—C10—C11—C12	−0.6 (8)	O11—S1—C13—F12	−177.9 (13)
O1—C10—C11—C12	175.6 (4)	O11^iii—S1—C13—F12	2.1 (13)
C8—C7—C12—C11	−1.9 (8)	O12^iii—S1—C13—F12	−111.6 (15)
N2—C7—C12—C11	178.3 (5)	O12—S1—C13—F12	68.4 (15)
C10—C11—C12—C7	1.8 (8)	O13^iii—S1—C13—F13	70.9 (17)
O13^iii—S1—O11—O13	180.000 (9)	O13—S1—C13—F13	−109.1 (17)
O12^iii—S1—O11—O13	−138.6 (12)	O11—S1—C13—F13	−62.1 (14)
O12—S1—O11—O13	41.4 (12)	O11^iii—S1—C13—F13	117.9 (14)
C13^iii—S1—O11—O13	117.8 (10)	O12^iii—S1—C13—F13	4.3 (13)
C13—S1—O11—O13	−62.2 (10)	O12—S1—C13—F13	−175.7 (13)

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