Poly[[bis-[μ(2)-N,N'-bis-(2-pyridyl-meth-yl)oxalamide-κN,O:N',O'][μ(2)-N,N'-bis-(2-pyridyl-meth-yl)oxalamide-κN:N']disilver(I)] bis-(trifluoro-methane-sulfonate)].

The asymmetric unit of the title salt, [Ag(C(14)H(14)N(4)O(2))(1.5)](CF(3)SO(3)), comprises a Ag(+) cation, three half-mol-ecules of N,N'-bis-(2-pyridyl-meth-yl)oxalamide (each of which is dis-posed about a centre of inversion) and a trifluoro-methane-sulfonate anion. Distinct coordination modes are found for the bridging ligands, i.e., a μ(2),κ(2)-bridging mode involving pyridine N atoms for one ligand, and a μ(2),κ(4)-bridging mode, employing both pyridine N and amide O atoms for the remaining ligands. The Ag(+) cations, which are in a distorted square-pyramidal coordination, and the ligands combine to form a two-dimensional array parallel to (101); these arrays are connected into a three-dimensional structure by trifluoro-methane-sulfonate anions via N-H⋯O, C-H⋯O, and C-F⋯O inter-actions.

Related literature

For structural diversity in the structures of silver salts, see: Kundu et al. (2010 ▶). For crystal engineering studies on isomeric N,N′-bis­(3-pyridyl­meth­yl)oxalamides, see: Poplaukhin & Tiekink (2010 ▶). For the structure of the BF4 − salt, see: Schauer et al. (1998 ▶). For additional structural analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Ag(C14H14N4O2)1.5](CF3SO3)

M = 662.38

Triclinic,

a = 8.7242 (14) Å

b = 11.1762 (17) Å

c = 14.210 (2) Å

α = 95.977 (1)°

β = 105.948 (2)°

γ = 107.017 (3)°

V = 1247.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.97 mm−1

T = 98 K

0.36 × 0.32 × 0.18 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.868, T max = 1.000

10177 measured reflections

5688 independent reflections

5438 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 1.05

5688 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −1.05 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033611/pv2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033611/pv2322Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C14H14N4O2)1.5](CF3SO3)	Z = 2
Mr = 662.38	F(000) = 666
Triclinic, P1	Dx = 1.763 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.7242 (14) Å	Cell parameters from 5470 reflections
b = 11.1762 (17) Å	θ = 2.7–40.5°
c = 14.210 (2) Å	µ = 0.97 mm−1
α = 95.977 (1)°	T = 98 K
β = 105.948 (2)°	Plate, colourless
γ = 107.017 (3)°	0.36 × 0.32 × 0.18 mm
V = 1247.9 (3) Å3

Rigaku AFC12K/SATURN724 diffractometer	5688 independent reflections
Radiation source: fine-focus sealed tube	5438 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.868, Tmax = 1.000	k = −14→14
10177 measured reflections	l = −18→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0295P)2 + 1.3977P] where P = (Fo2 + 2Fc2)/3
5688 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −1.05 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ag	0.18992 (2)	0.789941 (17)	0.198313 (13)	0.01680 (6)
S1	0.83484 (8)	0.26442 (7)	0.26813 (5)	0.02348 (14)
F1	0.6446 (3)	0.3310 (3)	0.36252 (17)	0.0586 (6)
F2	0.8906 (4)	0.4736 (2)	0.39309 (18)	0.0663 (7)
F3	0.8647 (3)	0.3038 (2)	0.45763 (14)	0.0527 (6)
O1	−0.1034 (2)	0.56970 (17)	0.06781 (14)	0.0230 (4)
O2	0.4189 (2)	0.89384 (17)	0.38477 (13)	0.0210 (4)
O3	0.5809 (2)	0.65495 (16)	0.47965 (13)	0.0180 (3)
O4	0.7817 (3)	0.3298 (2)	0.18909 (16)	0.0330 (5)
O5	0.7255 (2)	0.1362 (2)	0.25641 (17)	0.0346 (5)
O6	1.0141 (2)	0.28246 (18)	0.29925 (16)	0.0284 (4)
N1	0.2257 (3)	0.8994 (2)	0.06692 (15)	0.0171 (4)
N2	0.0110 (3)	0.63965 (19)	−0.05116 (15)	0.0183 (4)
H2N	0.0695	0.6247	−0.0898	0.022*
N3	0.0373 (3)	0.8513 (2)	0.28181 (15)	0.0178 (4)
N4	0.3734 (3)	1.07931 (19)	0.42923 (15)	0.0162 (4)
H4N	0.4058	1.1475	0.4765	0.019*
N5	0.3388 (2)	0.65910 (18)	0.18415 (15)	0.0148 (4)
N6	0.3291 (3)	0.49849 (19)	0.39599 (15)	0.0166 (4)
H6N	0.2627	0.4214	0.3942	0.020*
C1	0.3585 (3)	1.0079 (2)	0.09336 (19)	0.0203 (5)
H1	0.4419	1.0246	0.1568	0.024*
C2	0.3804 (3)	1.0972 (2)	0.0328 (2)	0.0229 (5)
H2	0.4757	1.1735	0.0545	0.028*
C3	0.2598 (4)	1.0721 (3)	−0.0599 (2)	0.0257 (6)
H3	0.2707	1.1308	−0.1035	0.031*
C4	0.1235 (3)	0.9603 (2)	−0.08807 (19)	0.0219 (5)
H4	0.0394	0.9414	−0.1516	0.026*
C5	0.1091 (3)	0.8756 (2)	−0.02376 (18)	0.0177 (5)
C6	−0.0395 (3)	0.7529 (2)	−0.0529 (2)	0.0210 (5)
H6A	−0.1056	0.7548	−0.0066	0.025*
H6B	−0.1140	0.7473	−0.1210	0.025*
C7	−0.0292 (3)	0.5578 (2)	0.00759 (18)	0.0168 (5)
C8	−0.1050 (3)	0.7645 (3)	0.2844 (2)	0.0240 (5)
H8	−0.1325	0.6781	0.2532	0.029*
C9	−0.2128 (3)	0.7952 (3)	0.3302 (2)	0.0292 (6)
H9	−0.3111	0.7310	0.3314	0.035*
C10	−0.1752 (3)	0.9210 (3)	0.3744 (2)	0.0286 (6)
H10	−0.2494	0.9452	0.4042	0.034*
C11	−0.0268 (3)	1.0114 (3)	0.37424 (19)	0.0224 (5)
H11	0.0028	1.0983	0.4049	0.027*
C12	0.0774 (3)	0.9732 (2)	0.32879 (17)	0.0159 (4)
C13	0.2458 (3)	1.0686 (2)	0.33435 (17)	0.0173 (5)
H13A	0.2820	1.0402	0.2783	0.021*
H13B	0.2335	1.1531	0.3286	0.021*
C14	0.4416 (3)	0.9886 (2)	0.44598 (17)	0.0155 (4)
C15	0.4180 (3)	0.6709 (2)	0.11494 (17)	0.0180 (5)
H15	0.4053	0.7318	0.0741	0.022*
C16	0.5166 (3)	0.5990 (2)	0.10053 (18)	0.0203 (5)
H16	0.5752	0.6132	0.0532	0.024*
C17	0.5288 (3)	0.5057 (3)	0.15634 (19)	0.0237 (5)
H17	0.5921	0.4522	0.1462	0.028*
C18	0.4466 (3)	0.4921 (2)	0.22738 (19)	0.0207 (5)
H18	0.4524	0.4284	0.2663	0.025*
C19	0.3555 (3)	0.5721 (2)	0.24127 (17)	0.0147 (4)
C20	0.2721 (3)	0.5694 (2)	0.32159 (17)	0.0167 (5)
H20A	0.2964	0.6582	0.3552	0.020*
H20B	0.1480	0.5304	0.2900	0.020*
C21	0.4798 (3)	0.5475 (2)	0.46690 (17)	0.0152 (4)
C22	0.8089 (5)	0.3483 (3)	0.3762 (2)	0.0387 (7)

	U11	U22	U33	U12	U13	U23
Ag	0.01925 (10)	0.01673 (10)	0.01533 (10)	0.00778 (7)	0.00530 (7)	0.00263 (7)
S1	0.0203 (3)	0.0251 (3)	0.0249 (3)	0.0084 (3)	0.0054 (3)	0.0072 (3)
F1	0.0680 (15)	0.0967 (19)	0.0516 (13)	0.0604 (15)	0.0387 (12)	0.0368 (13)
F2	0.108 (2)	0.0355 (12)	0.0527 (14)	0.0256 (13)	0.0241 (14)	−0.0027 (10)
F3	0.0741 (15)	0.0691 (15)	0.0260 (9)	0.0405 (13)	0.0131 (10)	0.0164 (10)
O1	0.0281 (9)	0.0181 (9)	0.0243 (9)	0.0069 (7)	0.0121 (8)	0.0028 (7)
O2	0.0221 (9)	0.0180 (9)	0.0183 (8)	0.0072 (7)	0.0015 (7)	−0.0030 (7)
O3	0.0194 (8)	0.0137 (8)	0.0183 (8)	0.0030 (7)	0.0046 (7)	0.0043 (7)
O4	0.0376 (11)	0.0423 (12)	0.0318 (11)	0.0238 (10)	0.0157 (9)	0.0182 (10)
O5	0.0208 (9)	0.0291 (11)	0.0438 (12)	0.0022 (8)	0.0010 (9)	0.0082 (10)
O6	0.0176 (9)	0.0223 (10)	0.0402 (11)	0.0034 (7)	0.0049 (8)	0.0058 (9)
N1	0.0180 (10)	0.0182 (10)	0.0151 (9)	0.0065 (8)	0.0046 (8)	0.0040 (8)
N2	0.0201 (10)	0.0135 (9)	0.0195 (10)	0.0045 (8)	0.0050 (8)	0.0033 (8)
N3	0.0151 (9)	0.0199 (10)	0.0169 (10)	0.0047 (8)	0.0042 (8)	0.0032 (8)
N4	0.0167 (9)	0.0143 (9)	0.0140 (9)	0.0046 (8)	0.0014 (8)	−0.0005 (8)
N5	0.0152 (9)	0.0131 (9)	0.0156 (9)	0.0043 (7)	0.0047 (8)	0.0022 (7)
N6	0.0174 (9)	0.0128 (9)	0.0171 (9)	0.0024 (8)	0.0032 (8)	0.0064 (8)
C1	0.0179 (11)	0.0223 (12)	0.0186 (11)	0.0054 (10)	0.0054 (10)	0.0008 (10)
C2	0.0238 (13)	0.0166 (12)	0.0259 (13)	0.0015 (10)	0.0108 (11)	0.0017 (10)
C3	0.0358 (15)	0.0180 (12)	0.0259 (13)	0.0079 (11)	0.0132 (12)	0.0100 (10)
C4	0.0273 (13)	0.0203 (12)	0.0176 (12)	0.0095 (10)	0.0040 (10)	0.0058 (10)
C5	0.0193 (11)	0.0152 (11)	0.0183 (11)	0.0063 (9)	0.0053 (9)	0.0025 (9)
C6	0.0193 (12)	0.0157 (12)	0.0244 (12)	0.0062 (10)	0.0014 (10)	0.0039 (10)
C7	0.0148 (10)	0.0133 (11)	0.0160 (11)	0.0020 (9)	−0.0005 (9)	−0.0006 (9)
C8	0.0180 (12)	0.0254 (13)	0.0216 (12)	0.0010 (10)	0.0031 (10)	0.0031 (10)
C9	0.0160 (12)	0.0426 (17)	0.0222 (13)	0.0006 (11)	0.0061 (10)	0.0052 (12)
C10	0.0214 (13)	0.0506 (18)	0.0181 (12)	0.0169 (13)	0.0080 (11)	0.0062 (12)
C11	0.0231 (12)	0.0309 (14)	0.0174 (11)	0.0156 (11)	0.0059 (10)	0.0050 (10)
C12	0.0168 (11)	0.0197 (12)	0.0108 (10)	0.0079 (9)	0.0015 (9)	0.0038 (9)
C13	0.0194 (11)	0.0176 (11)	0.0156 (11)	0.0078 (9)	0.0043 (9)	0.0054 (9)
C14	0.0127 (10)	0.0153 (11)	0.0166 (11)	0.0025 (8)	0.0048 (9)	0.0013 (9)
C15	0.0203 (11)	0.0176 (11)	0.0131 (10)	0.0041 (9)	0.0034 (9)	0.0025 (9)
C16	0.0195 (11)	0.0222 (12)	0.0162 (11)	0.0056 (10)	0.0053 (9)	−0.0027 (9)
C17	0.0256 (13)	0.0245 (13)	0.0201 (12)	0.0127 (11)	0.0039 (10)	−0.0025 (10)
C18	0.0249 (12)	0.0183 (12)	0.0191 (12)	0.0119 (10)	0.0027 (10)	0.0035 (10)
C19	0.0129 (10)	0.0132 (10)	0.0133 (10)	0.0020 (8)	0.0000 (8)	0.0010 (8)
C20	0.0176 (11)	0.0164 (11)	0.0153 (11)	0.0061 (9)	0.0031 (9)	0.0052 (9)
C21	0.0190 (11)	0.0151 (11)	0.0135 (10)	0.0071 (9)	0.0065 (9)	0.0038 (9)
C22	0.0490 (19)	0.0446 (19)	0.0307 (16)	0.0252 (16)	0.0144 (15)	0.0101 (14)

Ag—N1	2.378 (2)	C2—H2	0.9500
Ag—N3	2.210 (2)	C3—C4	1.378 (4)
Ag—N5	2.250 (2)	C3—H3	0.9500
Ag—O1	2.9665 (19)	C4—C5	1.386 (3)
Ag—O2	2.7299 (17)	C4—H4	0.9500
S1—O5	1.433 (2)	C5—C6	1.510 (3)
S1—O4	1.447 (2)	C6—H6A	0.9900
S1—O6	1.4487 (19)	C6—H6B	0.9900
S1—C22	1.818 (3)	C7—C7i	1.537 (5)
F1—C22	1.344 (4)	C8—C9	1.381 (4)
F2—C22	1.333 (4)	C8—H8	0.9500
F3—C22	1.333 (4)	C9—C10	1.382 (4)
O1—C7	1.225 (3)	C9—H9	0.9500
O2—C14	1.228 (3)	C10—C11	1.391 (4)
O3—C21	1.225 (3)	C10—H10	0.9500
N1—C1	1.341 (3)	C11—C12	1.385 (3)
N1—C5	1.347 (3)	C11—H11	0.9500
N2—C7	1.337 (3)	C12—C13	1.518 (3)
N2—C6	1.457 (3)	C13—H13A	0.9900
N2—H2N	0.8800	C13—H13B	0.9900
N3—C8	1.346 (3)	C14—C14ii	1.538 (5)
N3—C12	1.352 (3)	C15—C16	1.376 (4)
N4—C14	1.329 (3)	C15—H15	0.9500
N4—C13	1.461 (3)	C16—C17	1.386 (4)
N4—H4N	0.8800	C16—H16	0.9500
N5—C19	1.344 (3)	C17—C18	1.387 (4)
N5—C15	1.345 (3)	C17—H17	0.9500
N6—C21	1.334 (3)	C18—C19	1.392 (3)
N6—C20	1.452 (3)	C18—H18	0.9500
N6—H6N	0.8800	C19—C20	1.511 (3)
C1—C2	1.390 (4)	C20—H20A	0.9900
C1—H1	0.9500	C20—H20B	0.9900
C2—C3	1.382 (4)	C21—C21iii	1.543 (4)
N3—Ag—N5	145.64 (8)	O1—C7—N2	125.9 (2)
N3—Ag—N1	114.52 (7)	O1—C7—C7i	121.7 (3)
N5—Ag—N1	99.84 (7)	N2—C7—C7i	112.3 (3)
N3—Ag—O2	77.39 (7)	N3—C8—C9	123.0 (3)
N5—Ag—O2	86.55 (6)	N3—C8—H8	118.5
N1—Ag—O2	117.91 (6)	C9—C8—H8	118.5
N3—Ag—O1	92.93 (6)	C8—C9—C10	118.9 (3)
N5—Ag—O1	84.19 (6)	C8—C9—H9	120.5
N1—Ag—O1	94.90 (6)	C10—C9—H9	120.5
O2—Ag—O1	146.99 (5)	C9—C10—C11	118.8 (2)
O5—S1—O4	115.07 (13)	C9—C10—H10	120.6
O5—S1—O6	115.22 (12)	C11—C10—H10	120.6
O4—S1—O6	114.01 (13)	C12—C11—C10	119.1 (3)
O5—S1—C22	102.86 (16)	C12—C11—H11	120.4
O4—S1—C22	104.09 (14)	C10—C11—H11	120.4
O6—S1—C22	103.39 (15)	N3—C12—C11	122.2 (2)
C7—O1—Ag	91.70 (14)	N3—C12—C13	118.0 (2)
C14—O2—Ag	131.58 (16)	C11—C12—C13	119.8 (2)
C1—N1—C5	117.9 (2)	N4—C13—C12	109.80 (19)
C1—N1—Ag	115.41 (16)	N4—C13—H13A	109.7
C5—N1—Ag	125.33 (16)	C12—C13—H13A	109.7
C7—N2—C6	121.8 (2)	N4—C13—H13B	109.7
C7—N2—H2N	119.1	C12—C13—H13B	109.7
C6—N2—H2N	119.1	H13A—C13—H13B	108.2
C8—N3—C12	117.9 (2)	O2—C14—N4	126.2 (2)
C8—N3—Ag	118.87 (18)	O2—C14—C14ii	120.5 (3)
C12—N3—Ag	123.19 (16)	N4—C14—C14ii	113.3 (3)
C14—N4—C13	121.6 (2)	N5—C15—C16	123.1 (2)
C14—N4—H4N	119.2	N5—C15—H15	118.5
C13—N4—H4N	119.2	C16—C15—H15	118.5
C19—N5—C15	118.4 (2)	C15—C16—C17	118.8 (2)
C19—N5—Ag	124.21 (15)	C15—C16—H16	120.6
C15—N5—Ag	117.34 (16)	C17—C16—H16	120.6
C21—N6—C20	121.6 (2)	C16—C17—C18	118.5 (2)
C21—N6—H6N	119.2	C16—C17—H17	120.7
C20—N6—H6N	119.2	C18—C17—H17	120.7
N1—C1—C2	123.4 (2)	C17—C18—C19	119.6 (2)
N1—C1—H1	118.3	C17—C18—H18	120.2
C2—C1—H1	118.3	C19—C18—H18	120.2
C3—C2—C1	118.2 (2)	N5—C19—C18	121.4 (2)
C3—C2—H2	120.9	N5—C19—C20	115.7 (2)
C1—C2—H2	120.9	C18—C19—C20	122.9 (2)
C4—C3—C2	118.8 (2)	N6—C20—C19	113.0 (2)
C4—C3—H3	120.6	N6—C20—H20A	109.0
C2—C3—H3	120.6	C19—C20—H20A	109.0
C3—C4—C5	120.0 (2)	N6—C20—H20B	109.0
C3—C4—H4	120.0	C19—C20—H20B	109.0
C5—C4—H4	120.0	H20A—C20—H20B	107.8
N1—C5—C4	121.7 (2)	O3—C21—N6	125.6 (2)
N1—C5—C6	117.5 (2)	O3—C21—C21iii	121.4 (3)
C4—C5—C6	120.9 (2)	N6—C21—C21iii	113.0 (2)
N2—C6—C5	113.0 (2)	F3—C22—F2	109.1 (3)
N2—C6—H6A	109.0	F3—C22—F1	106.6 (3)
C5—C6—H6A	109.0	F2—C22—F1	107.8 (3)
N2—C6—H6B	109.0	F3—C22—S1	111.0 (2)
C5—C6—H6B	109.0	F2—C22—S1	111.4 (2)
H6A—C6—H6B	107.8	F1—C22—S1	110.8 (2)
N3—Ag—O1—C7	163.63 (15)	Ag—O1—C7—C7i	111.3 (3)
N5—Ag—O1—C7	−50.71 (15)	C6—N2—C7—O1	−3.3 (4)
N1—Ag—O1—C7	48.71 (15)	C6—N2—C7—C7i	176.9 (2)
O2—Ag—O1—C7	−125.18 (15)	C12—N3—C8—C9	1.8 (4)
N3—Ag—O2—C14	−39.2 (2)	Ag—N3—C8—C9	−176.6 (2)
N5—Ag—O2—C14	171.4 (2)	N3—C8—C9—C10	1.0 (4)
N1—Ag—O2—C14	72.1 (2)	C8—C9—C10—C11	−2.4 (4)
O1—Ag—O2—C14	−114.8 (2)	C9—C10—C11—C12	0.9 (4)
N3—Ag—N1—C1	87.98 (19)	C8—N3—C12—C11	−3.3 (3)
N5—Ag—N1—C1	−91.61 (18)	Ag—N3—C12—C11	175.01 (18)
O2—Ag—N1—C1	−0.3 (2)	C8—N3—C12—C13	174.4 (2)
O1—Ag—N1—C1	−176.54 (17)	Ag—N3—C12—C13	−7.3 (3)
N3—Ag—N1—C5	−78.4 (2)	C10—C11—C12—N3	2.0 (4)
N5—Ag—N1—C5	102.0 (2)	C10—C11—C12—C13	−175.7 (2)
O2—Ag—N1—C5	−166.73 (18)	C14—N4—C13—C12	74.8 (3)
O1—Ag—N1—C5	17.0 (2)	N3—C12—C13—N4	−95.2 (2)
N5—Ag—N3—C8	−60.0 (2)	C11—C12—C13—N4	82.5 (3)
N1—Ag—N3—C8	120.70 (19)	Ag—O2—C14—N4	−11.8 (4)
O2—Ag—N3—C8	−124.1 (2)	Ag—O2—C14—C14ii	168.21 (18)
O1—Ag—N3—C8	23.97 (19)	C13—N4—C14—O2	6.2 (4)
N5—Ag—N3—C12	121.69 (19)	C13—N4—C14—C14ii	−173.8 (2)
N1—Ag—N3—C12	−57.6 (2)	C19—N5—C15—C16	−0.6 (3)
O2—Ag—N3—C12	57.57 (18)	Ag—N5—C15—C16	178.29 (18)
O1—Ag—N3—C12	−154.33 (18)	N5—C15—C16—C17	3.2 (4)
N3—Ag—N5—C19	2.5 (3)	C15—C16—C17—C18	−2.6 (4)
N1—Ag—N5—C19	−178.21 (18)	C16—C17—C18—C19	−0.4 (4)
O2—Ag—N5—C19	64.05 (18)	C15—N5—C19—C18	−2.5 (3)
O1—Ag—N5—C19	−84.22 (18)	Ag—N5—C19—C18	178.64 (17)
N3—Ag—N5—C15	−176.41 (15)	C15—N5—C19—C20	176.4 (2)
N1—Ag—N5—C15	2.93 (18)	Ag—N5—C19—C20	−2.4 (3)
O2—Ag—N5—C15	−114.81 (17)	C17—C18—C19—N5	3.0 (4)
O1—Ag—N5—C15	96.91 (17)	C17—C18—C19—C20	−175.8 (2)
C5—N1—C1—C2	0.9 (4)	C21—N6—C20—C19	76.1 (3)
Ag—N1—C1—C2	−166.6 (2)	N5—C19—C20—N6	−165.2 (2)
N1—C1—C2—C3	−0.7 (4)	C18—C19—C20—N6	13.7 (3)
C1—C2—C3—C4	0.2 (4)	C20—N6—C21—O3	2.8 (4)
C2—C3—C4—C5	0.1 (4)	C20—N6—C21—C21iii	−175.8 (2)
C1—N1—C5—C4	−0.6 (4)	O5—S1—C22—F3	64.0 (3)
Ag—N1—C5—C4	165.49 (18)	O4—S1—C22—F3	−175.7 (2)
C1—N1—C5—C6	179.8 (2)	O6—S1—C22—F3	−56.3 (3)
Ag—N1—C5—C6	−14.1 (3)	O5—S1—C22—F2	−174.2 (2)
C3—C4—C5—N1	0.2 (4)	O4—S1—C22—F2	−53.9 (3)
C3—C4—C5—C6	179.8 (2)	O6—S1—C22—F2	65.5 (3)
C7—N2—C6—C5	120.3 (2)	O5—S1—C22—F1	−54.3 (3)
N1—C5—C6—N2	−58.2 (3)	O4—S1—C22—F1	66.1 (3)
C4—C5—C6—N2	122.2 (3)	O6—S1—C22—F1	−174.5 (2)
Ag—O1—C7—N2	−68.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4iv	0.88	2.17	2.992 (4)	156
N4—H4n···O3ii	0.88	2.19	2.980 (3)	149
N6—H6n···O6v	0.88	2.22	2.936 (3)	139
C1—H1···O5vi	0.95	2.36	3.197 (3)	146
C17—H17···O4	0.95	2.43	3.334 (4)	158
C18—H18···F1	0.95	2.45	3.261 (4)	144
N2—H2n···O1i	0.88	2.32	2.697 (3)	106
N4—H4n···O2ii	0.88	2.32	2.692 (3)	105
N6—H6n···O3iii	0.88	2.34	2.709 (3)	106

Table 1

Selected bond lengths (Å)

Ag—N1	2.378 (2)
Ag—N3	2.210 (2)
Ag—N5	2.250 (2)
Ag—O1	2.9665 (19)
Ag—O2	2.7299 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O4i	0.88	2.17	2.992 (4)	156
N4—H4n⋯O3ii	0.88	2.19	2.980 (3)	149
N6—H6n⋯O6iii	0.88	2.22	2.936 (3)	139
C1—H1⋯O5iv	0.95	2.36	3.197 (3)	146
C17—H17⋯O4	0.95	2.43	3.334 (4)	158
C18—H18⋯F1	0.95	2.45	3.261 (4)	144
N2—H2n⋯O1v	0.88	2.32	2.697 (3)	106
N4—H4n⋯O2ii	0.88	2.32	2.692 (3)	105
N6—H6n⋯O3vi	0.88	2.34	2.709 (3)	106

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .