Bis(μ-pyridine-1-carbaldehyde azine-κ2N,N′:κN′′)disilver(I) bis­(p-toluene­sulfonate)

Broker, G.A.; Tiekink, E.R.T.

doi:10.1107/S1600536807040809

Bis(μ-pyridine-1-carbaldehyde azine-κ²N,N′:κN′′)disilver(I) bis(p-toluenesulfonate)

The title compound, [Ag₂(C₁₂H₁₀N₄)₂](p-CH₃C₆H₄SO₃)₂, features a centrosymmetric dication and T-shaped AgN₃ coordination geometry, as each ligand is tridentate, forming a bond to one Ag atom and chelating the other. The p-toluenesulfonate anion accepts a weak Ag

O contact [2.5023 (14) Å], as well as forming C—H

O interactions. The crystal structure comprises layers, stabilized by C—H

O contacts and connected by C—H

π interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040809/hb2512sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040809/hb2512Isup2.hkl Contains datablock I

CCDC reference: 660165

checkCIF report

Key indicators

Single-crystal X-ray study
T = 98 K
Mean (C-C) = 0.003 Å
R factor = 0.020
wR factor = 0.052
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.940
            Tmax scaled      0.940 Tmin scaled      0.672

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, [Ag₂(C₁₂H₁₀N₄)₂](p-CH₃C₆H₄SO₃)₂ or [Ag(2—PA)]₂[(p-tol)SO₃]₂ (I), was investigated as a part of an on-going study of the structural chemistry of Ag salts of isomeric n-pyridinealdazine molecules, n = 2, 3 and 4 (Broker & Tiekink, 2007). The centrosymmetric dication adopts a ring structure as the two Ag atoms are bridged by two tridentate 2-PA molecules, each forming a single bond to one Ag atom and a chelating interaction to the other (Fig. 1 & Table 1). Within the chelate, the Ag–N_azo bond distance is significantly shorter than the Ag–N_pyridine bond; the coordination geometry around each Ag atom is T-shaped. The [(p-tol)SO₃]^- anion forms a close contact with Ag, i.e. Ag···O2 = 2.5023 (14) Å.

The dinuclear cation in (I) has three precedents in the literature, namely in the [CF₃SO₃]^- (Hamblin et al., 2002), [NO₃]^- (Kennedy et al., 2005) and [CH₃SO₃]^- (Broker & Tiekink, 2007) salts for which similar ring structures have been reported. By contrast, in the [BF₄]^- salt, characterized as an acetonitrile solvate, a polymeric structure is observed instead due to a rotation of one of the pyridine rings (Guo et al., 2002); in this case, the 2-PA ligand is tetradentate forming two chelate rings.

The global crystal packing in (I) is based on the stacking of layers along the c-direction as illustrated in Fig. 2. Thus, the tosylate-O1 and O3 atoms connect dinuclear cations into layers in the ab-plane via C—H···O interactions (Table 2); the O2 atom accepts an intramolecular C—H···O contact exclusively. The primary interactions between layers appear to be of the type C—H···π, i.e. C17—H···Cg(N4, C8—C12) = 2.69 Å, with an angle at H17 of 133° for symmetry operation (1 - x, 1 - y, 1 - z).

Related literature top

For related dinuclear structures, see: Hamblin et al. (2002); Kennedy et al. (2005); Broker & Tiekink (2007). For a a polymeric analogue, see: Guo et al. (2002).

Experimental top

[Ag(p-tol)SO₃] (Aldrich, 0.05 g, 0.18 mmol) was dissolved in CH₃CN (20 ml) and layered on top of a CH₂Cl₂ solution (20 ml) containing (0.04 g, 0.18 mmol) of 2-pyridinealdazine (Aldrich). After three days, yellow prisms of (I) were observed at the interface between the two layers; m.p. 493–495 K.

Structure description top

For related dinuclear structures, see: Hamblin et al. (2002); Kennedy et al. (2005); Broker & Tiekink (2007). For a a polymeric analogue, see: Guo et al. (2002).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 70% probability level (arbitrary spheres for the H atoms). Primed atoms are generated by the symmetry operation (-x, 1 - y, 2 - z).
	Fig. 2. View of the crystal packing in (I) down the a axis highlighting the layer arrangement. The C–H···O interactions are shown as orange-dashed lines. Colour code: orange (silver), yellow (sulfur), red (oxygen), blue (nitrogen), grey (carbon) and green (hydrogen).

Bis(µ-pyridine-1-carbaldehyde azine-κ²N,N':κN'')disilver(I) bis(p-toluenesulfonate) top

Crystal data top

[Ag₂(C₁₂H₁₀N₄)₂](C₇H₇SO₃)₂	Z = 1
M_r = 978.61	F(000) = 492
Triclinic, P1	D_x = 1.771 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 7.9619 (17) Å	Cell parameters from 2621 reflections
b = 9.4382 (11) Å	θ = 2.6–30.2°
c = 13.468 (3) Å	µ = 1.24 mm⁻¹
α = 78.12 (3)°	T = 98 K
β = 76.75 (3)°	Prism, yellow
γ = 70.13 (3)°	0.35 × 0.10 × 0.05 mm
V = 917.4 (3) Å³

Data collection top

Rigaku/MSC AFC12κ/SATURN724 diffractometer	3776 independent reflections
Radiation source: fine-focus sealed tube	3713 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 26.5°, θ_min = 2.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.715, T_max = 1.000	k = −11→11
10013 measured reflections	l = −15→16

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0249P)² + 0.8243P] where P = (F_o² + 2F_c²)/3
3776 reflections	(Δ/σ)_max = 0.005
254 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Ag₂(C₁₂H₁₀N₄)₂](C₇H₇SO₃)₂	γ = 70.13 (3)°
M_r = 978.61	V = 917.4 (3) Å³
Triclinic, P1	Z = 1
a = 7.9619 (17) Å	Mo Kα radiation
b = 9.4382 (11) Å	µ = 1.24 mm⁻¹
c = 13.468 (3) Å	T = 98 K
α = 78.12 (3)°	0.35 × 0.10 × 0.05 mm
β = 76.75 (3)°

Data collection top

Rigaku/MSC AFC12κ/SATURN724 diffractometer	3776 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3713 reflections with I > 2σ(I)
T_min = 0.715, T_max = 1.000	R_int = 0.018
10013 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.07	Δρ_max = 0.46 e Å⁻³
3776 reflections	Δρ_min = −0.42 e Å⁻³
254 parameters

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
Ag	0.270539 (16)	0.533834 (14)	0.880628 (10)	0.01623 (5)
S1	0.11139 (5)	0.33155 (5)	0.76383 (3)	0.01453 (9)
O1	0.00032 (19)	0.46865 (17)	0.71172 (12)	0.0307 (3)
O2	0.12104 (17)	0.34521 (16)	0.86852 (10)	0.0209 (3)
O3	0.06566 (18)	0.19598 (16)	0.76129 (11)	0.0228 (3)
N1	−0.45024 (19)	0.65008 (17)	1.01938 (11)	0.0142 (3)
N2	−0.12641 (19)	0.81213 (17)	0.85496 (12)	0.0161 (3)
N3	0.06292 (19)	0.75793 (17)	0.82718 (11)	0.0143 (3)
N4	0.4262 (2)	0.67661 (17)	0.74678 (11)	0.0152 (3)
C1	−0.6304 (2)	0.6843 (2)	1.05199 (14)	0.0161 (3)
H1	−0.6753	0.6118	1.1009	0.019*
C2	−0.7532 (2)	0.8191 (2)	1.01822 (14)	0.0186 (4)
H2	−0.8793	0.8389	1.0440	0.022*
C3	−0.6897 (2)	0.9254 (2)	0.94594 (14)	0.0187 (4)
H3	−0.7708	1.0198	0.9218	0.022*
C4	−0.5054 (2)	0.8904 (2)	0.91000 (14)	0.0167 (3)
H4	−0.4581	0.9597	0.8593	0.020*
C5	−0.3897 (2)	0.75296 (19)	0.94858 (13)	0.0134 (3)
C6	−0.1924 (2)	0.7123 (2)	0.91352 (13)	0.0139 (3)
H6	−0.1156	0.6136	0.9341	0.017*
C7	0.1246 (2)	0.8529 (2)	0.75909 (14)	0.0153 (3)
H7	0.0433	0.9466	0.7340	0.018*
C8	0.3194 (2)	0.8182 (2)	0.71959 (13)	0.0139 (3)
C9	0.6040 (2)	0.6460 (2)	0.71350 (14)	0.0166 (3)
H9	0.6807	0.5462	0.7316	0.020*
C10	0.6828 (2)	0.7538 (2)	0.65329 (14)	0.0182 (4)
H10	0.8106	0.7283	0.6322	0.022*
C11	0.5717 (2)	0.8983 (2)	0.62486 (14)	0.0179 (4)
H11	0.6218	0.9737	0.5837	0.021*
C12	0.3859 (2)	0.9314 (2)	0.65742 (14)	0.0166 (3)
H12	0.3060	1.0291	0.6377	0.020*
C13	0.3356 (2)	0.30503 (19)	0.69408 (13)	0.0138 (3)
C14	0.4828 (2)	0.2515 (2)	0.74534 (14)	0.0154 (3)
H14	0.4638	0.2270	0.8182	0.018*
C15	0.6573 (2)	0.2336 (2)	0.69066 (15)	0.0183 (4)
H15	0.7570	0.1982	0.7264	0.022*
C16	0.6874 (2)	0.2671 (2)	0.58368 (15)	0.0179 (4)
C17	0.5387 (3)	0.3178 (2)	0.53321 (14)	0.0193 (4)
H17	0.5576	0.3392	0.4602	0.023*
C18	0.3635 (2)	0.3377 (2)	0.58741 (14)	0.0167 (3)
H18	0.2636	0.3733	0.5518	0.020*
C19	0.8762 (3)	0.2497 (3)	0.52383 (17)	0.0287 (5)
H19A	0.9352	0.1436	0.5120	0.043*
H19B	0.9463	0.2783	0.5631	0.043*
H19C	0.8698	0.3158	0.4575	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag	0.01410 (8)	0.01331 (8)	0.01916 (8)	−0.00401 (5)	−0.00385 (5)	0.00307 (5)
S1	0.00972 (19)	0.0146 (2)	0.0176 (2)	−0.00285 (16)	−0.00073 (15)	−0.00194 (16)
O1	0.0153 (7)	0.0281 (8)	0.0343 (8)	0.0036 (6)	−0.0024 (6)	0.0073 (6)
O2	0.0184 (6)	0.0280 (7)	0.0188 (7)	−0.0117 (6)	0.0031 (5)	−0.0083 (5)
O3	0.0160 (6)	0.0270 (7)	0.0301 (7)	−0.0125 (6)	0.0026 (5)	−0.0111 (6)
N1	0.0123 (7)	0.0148 (7)	0.0153 (7)	−0.0042 (6)	−0.0028 (5)	−0.0009 (6)
N2	0.0095 (7)	0.0172 (7)	0.0188 (8)	−0.0025 (6)	−0.0006 (6)	−0.0011 (6)
N3	0.0096 (7)	0.0149 (7)	0.0166 (7)	−0.0026 (6)	−0.0010 (5)	−0.0019 (6)
N4	0.0133 (7)	0.0148 (7)	0.0160 (7)	−0.0043 (6)	−0.0016 (6)	−0.0001 (6)
C1	0.0143 (8)	0.0201 (9)	0.0146 (8)	−0.0078 (7)	−0.0014 (6)	−0.0006 (7)
C2	0.0118 (8)	0.0246 (10)	0.0184 (9)	−0.0048 (7)	−0.0016 (7)	−0.0032 (7)
C3	0.0146 (8)	0.0173 (9)	0.0204 (9)	−0.0008 (7)	−0.0040 (7)	−0.0008 (7)
C4	0.0158 (8)	0.0164 (9)	0.0163 (8)	−0.0047 (7)	−0.0024 (7)	0.0007 (7)
C5	0.0128 (8)	0.0151 (8)	0.0127 (8)	−0.0042 (6)	−0.0024 (6)	−0.0026 (6)
C6	0.0131 (8)	0.0137 (8)	0.0135 (8)	−0.0025 (6)	−0.0033 (6)	−0.0007 (6)
C7	0.0132 (8)	0.0127 (8)	0.0181 (8)	−0.0027 (6)	−0.0022 (6)	−0.0007 (7)
C8	0.0127 (8)	0.0136 (8)	0.0152 (8)	−0.0041 (6)	−0.0024 (6)	−0.0016 (6)
C9	0.0125 (8)	0.0181 (9)	0.0166 (8)	−0.0029 (7)	−0.0019 (6)	−0.0002 (7)
C10	0.0128 (8)	0.0248 (10)	0.0162 (8)	−0.0070 (7)	−0.0005 (7)	−0.0012 (7)
C11	0.0182 (9)	0.0190 (9)	0.0173 (9)	−0.0101 (7)	0.0005 (7)	−0.0009 (7)
C12	0.0171 (8)	0.0147 (8)	0.0160 (8)	−0.0046 (7)	−0.0010 (7)	−0.0002 (7)
C13	0.0118 (8)	0.0115 (8)	0.0179 (8)	−0.0043 (6)	−0.0013 (6)	−0.0016 (6)
C14	0.0155 (8)	0.0143 (8)	0.0157 (8)	−0.0036 (7)	−0.0022 (7)	−0.0031 (6)
C15	0.0133 (8)	0.0180 (9)	0.0247 (9)	−0.0036 (7)	−0.0047 (7)	−0.0059 (7)
C16	0.0146 (8)	0.0142 (8)	0.0244 (9)	−0.0056 (7)	0.0021 (7)	−0.0057 (7)
C17	0.0221 (9)	0.0190 (9)	0.0161 (9)	−0.0084 (7)	0.0006 (7)	−0.0016 (7)
C18	0.0169 (8)	0.0151 (8)	0.0181 (9)	−0.0052 (7)	−0.0042 (7)	−0.0006 (7)
C19	0.0155 (9)	0.0343 (12)	0.0331 (11)	−0.0091 (8)	0.0065 (8)	−0.0070 (9)

Geometric parameters (Å, º) top

Ag—N1ⁱ	2.2596 (17)	C6—H6	0.9500
Ag—N3	2.2948 (17)	C7—C8	1.464 (2)
Ag—N4	2.3900 (17)	C7—H7	0.9500
Ag—O2	2.5023 (14)	C8—C12	1.391 (2)
S1—O1	1.4428 (15)	C9—C10	1.396 (3)
S1—O3	1.4530 (14)	C9—H9	0.9500
S1—O2	1.4636 (14)	C10—C11	1.382 (3)
S1—C13	1.7768 (18)	C10—H10	0.9500
N1—C1	1.345 (2)	C11—C12	1.387 (3)
N1—C5	1.346 (2)	C11—H11	0.9500
N1—Agⁱ	2.2596 (17)	C12—H12	0.9500
N2—C6	1.275 (2)	C13—C18	1.388 (3)
N2—N3	1.404 (2)	C13—C14	1.389 (2)
N3—C7	1.280 (2)	C14—C15	1.387 (3)
N4—C9	1.332 (2)	C14—H14	0.9500
N4—C8	1.346 (2)	C15—C16	1.392 (3)
C1—C2	1.379 (3)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.394 (3)
C2—C3	1.388 (3)	C16—C19	1.506 (3)
C2—H2	0.9500	C17—C18	1.387 (3)
C3—C4	1.381 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.389 (3)	C19—H19A	0.9800
C4—H4	0.9500	C19—H19B	0.9800
C5—C6	1.470 (2)	C19—H19C	0.9800

N1ⁱ—Ag—N3	161.06 (6)	N3—C7—H7	119.8
N1ⁱ—Ag—N4	114.74 (6)	C8—C7—H7	119.8
N3—Ag—N4	71.65 (6)	N4—C8—C12	123.14 (16)
N1ⁱ—Ag—O2	88.50 (5)	N4—C8—C7	117.51 (15)
N3—Ag—O2	100.89 (5)	C12—C8—C7	119.34 (16)
N4—Ag—O2	129.62 (5)	N4—C9—C10	123.02 (17)
O1—S1—O3	113.74 (9)	N4—C9—H9	118.5
O1—S1—O2	113.34 (10)	C10—C9—H9	118.5
O3—S1—O2	111.55 (9)	C11—C10—C9	118.79 (16)
O1—S1—C13	105.70 (9)	C11—C10—H10	120.6
O3—S1—C13	106.41 (8)	C9—C10—H10	120.6
O2—S1—C13	105.28 (8)	C10—C11—C12	118.95 (17)
S1—O2—Ag	115.18 (8)	C10—C11—H11	120.5
C1—N1—C5	117.32 (15)	C12—C11—H11	120.5
C1—N1—Agⁱ	117.09 (12)	C11—C12—C8	118.39 (17)
C5—N1—Agⁱ	122.77 (11)	C11—C12—H12	120.8
C6—N2—N3	112.67 (15)	C8—C12—H12	120.8
C7—N3—N2	111.79 (15)	C18—C13—C14	119.87 (16)
C7—N3—Ag	116.87 (12)	C18—C13—S1	119.54 (14)
N2—N3—Ag	131.33 (11)	C14—C13—S1	120.59 (14)
C9—N4—C8	117.66 (15)	C15—C14—C13	120.36 (17)
C9—N4—Ag	128.25 (12)	C15—C14—H14	119.8
C8—N4—Ag	112.49 (11)	C13—C14—H14	119.8
N1—C1—C2	123.45 (17)	C14—C15—C16	120.44 (17)
N1—C1—H1	118.3	C14—C15—H15	119.8
C2—C1—H1	118.3	C16—C15—H15	119.8
C1—C2—C3	118.92 (17)	C15—C16—C17	118.51 (17)
C1—C2—H2	120.5	C15—C16—C19	120.79 (18)
C3—C2—H2	120.5	C17—C16—C19	120.70 (18)
C4—C3—C2	118.26 (17)	C18—C17—C16	121.39 (17)
C4—C3—H3	120.9	C18—C17—H17	119.3
C2—C3—H3	120.9	C16—C17—H17	119.3
C3—C4—C5	119.54 (17)	C17—C18—C13	119.41 (17)
C3—C4—H4	120.2	C17—C18—H18	120.3
C5—C4—H4	120.2	C13—C18—H18	120.3
N1—C5—C4	122.48 (16)	C16—C19—H19A	109.5
N1—C5—C6	116.29 (15)	C16—C19—H19B	109.5
C4—C5—C6	121.23 (16)	H19A—C19—H19B	109.5
N2—C6—C5	118.72 (16)	C16—C19—H19C	109.5
N2—C6—H6	120.6	H19A—C19—H19C	109.5
C5—C6—H6	120.6	H19B—C19—H19C	109.5
N3—C7—C8	120.49 (16)

O1—S1—O2—Ag	−64.41 (10)	C4—C5—C6—N2	7.4 (3)
O3—S1—O2—Ag	165.65 (7)	N2—N3—C7—C8	179.92 (15)
C13—S1—O2—Ag	50.64 (10)	Ag—N3—C7—C8	−0.9 (2)
N1ⁱ—Ag—O2—S1	−128.37 (9)	C9—N4—C8—C12	1.2 (3)
N3—Ag—O2—S1	68.20 (9)	Ag—N4—C8—C12	168.05 (14)
N4—Ag—O2—S1	−6.91 (11)	C9—N4—C8—C7	−178.06 (16)
C6—N2—N3—C7	172.35 (16)	Ag—N4—C8—C7	−11.25 (19)
C6—N2—N3—Ag	−6.7 (2)	N3—C7—C8—N4	8.7 (3)
N1ⁱ—Ag—N3—C7	109.39 (19)	N3—C7—C8—C12	−170.59 (17)
N4—Ag—N3—C7	−3.67 (13)	C8—N4—C9—C10	0.6 (3)
O2—Ag—N3—C7	−132.02 (13)	Ag—N4—C9—C10	−163.79 (14)
N1ⁱ—Ag—N3—N2	−71.6 (2)	N4—C9—C10—C11	−1.4 (3)
N4—Ag—N3—N2	175.35 (16)	C9—C10—C11—C12	0.3 (3)
O2—Ag—N3—N2	47.01 (15)	C10—C11—C12—C8	1.5 (3)
N1ⁱ—Ag—N4—C9	12.19 (17)	N4—C8—C12—C11	−2.3 (3)
N3—Ag—N4—C9	172.99 (16)	C7—C8—C12—C11	176.99 (16)
O2—Ag—N4—C9	−97.93 (16)	O1—S1—C13—C18	−38.59 (17)
N1ⁱ—Ag—N4—C8	−152.90 (11)	O3—S1—C13—C18	82.66 (16)
N3—Ag—N4—C8	7.90 (11)	O2—S1—C13—C18	−158.82 (14)
O2—Ag—N4—C8	96.97 (13)	O1—S1—C13—C14	141.67 (15)
C5—N1—C1—C2	−1.3 (3)	O3—S1—C13—C14	−97.07 (16)
Agⁱ—N1—C1—C2	160.20 (14)	O2—S1—C13—C14	21.44 (17)
N1—C1—C2—C3	0.7 (3)	C18—C13—C14—C15	1.4 (3)
C1—C2—C3—C4	0.8 (3)	S1—C13—C14—C15	−178.83 (14)
C2—C3—C4—C5	−1.6 (3)	C13—C14—C15—C16	−0.9 (3)
C1—N1—C5—C4	0.5 (3)	C14—C15—C16—C17	−0.4 (3)
Agⁱ—N1—C5—C4	−159.94 (13)	C14—C15—C16—C19	179.30 (18)
C1—N1—C5—C6	−179.49 (15)	C15—C16—C17—C18	1.2 (3)
Agⁱ—N1—C5—C6	20.1 (2)	C19—C16—C17—C18	−178.54 (18)
C3—C4—C5—N1	1.0 (3)	C16—C17—C18—C13	−0.6 (3)
C3—C4—C5—C6	−179.05 (17)	C14—C13—C18—C17	−0.7 (3)
N3—N2—C6—C5	−179.77 (14)	S1—C13—C18—C17	179.58 (14)
N1—C5—C6—N2	−172.63 (16)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱⁱ	0.95	2.36	3.025 (2)	126
C10—H10···O1ⁱⁱ	0.95	2.56	3.109 (2)	117
C14—H14···O2	0.95	2.56	2.918 (2)	103
C7—H7···O3ⁱⁱⁱ	0.95	2.53	3.116 (2)	120
C12—H12···O3ⁱⁱⁱ	0.95	2.55	3.189 (2)	125
C15—H15···O3ⁱⁱ	0.95	2.60	3.478 (2)	154

Symmetry codes: (ii) x+1, y, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₂H₁₀N₄)₂](C₇H₇SO₃)₂
M_r	978.61
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	7.9619 (17), 9.4382 (11), 13.468 (3)
α, β, γ (°)	78.12 (3), 76.75 (3), 70.13 (3)
V (Å³)	917.4 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.35 × 0.10 × 0.05

Data collection
Diffractometer	Rigaku/MSC AFC12κ/SATURN724
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.715, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10013, 3776, 3713
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.052, 1.07
No. of reflections	3776
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.42

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006).

Selected geometric parameters (Å, º) top

Ag—N1ⁱ	2.2596 (17)	Ag—N4	2.3900 (17)
Ag—N3	2.2948 (17)

N1ⁱ—Ag—N3	161.06 (6)	N3—Ag—N4	71.65 (6)
N1ⁱ—Ag—N4	114.74 (6)