Bis[5-(pyridin-2-yl)pyrazine-2-carbo­nitrile-κ2N4,N5]silver(I) perchlorate

Zhang, F.; Wang, Z.-W.; Yang, Y.-L.

doi:10.1107/S1600536811046708

Bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ²N⁴,N⁵]silver(I) perchlorate

In the mononuclear title complex, [Ag(C₁₀H₆N₄)₂]ClO₄, the Ag^I ion is surrounded by two 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands, forming a considerably distorted square-planar N₄-coordination geometry, with two short and two long Ag—N distances. Each perchlorate anion links two mononuclear coordination units through C—H

O(perchlorate) hydrogen bonding, forming an infinite tape structure along [110]. Intermolecular π–π stacking interactions between adjacent pyridine and pyrazine rings [centroid–centroid distances of 3.777 (3) and 3.879 (2) Å] further assemble the tape motifs into a three-dimensional supramolecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811046708/ez2265sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811046708/ez2265Isup2.hkl Contains datablock I

CCDC reference: 858168

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.034
wR factor = 0.092
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          1

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.979
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        Ag1
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A   ..  O2      ..       2.71 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         20
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         90

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT194_ALERT_1_G Missing _cell_measurement_reflns_used datum ....          ?
PLAT195_ALERT_1_G Missing _cell_measurement_theta_max   datum ....          ?
PLAT196_ALERT_1_G Missing _cell_measurement_theta_min   datum ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C7     -   C10    ...       1.45 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C17    -   C20    ...       1.45 Ang.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         12
            N5  -AG1 -N1  -C5    151.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N5  -AG1 -N1  -C1    -26.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         39
            N1  -AG1 -N5  -C15    28.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         40
            N1  -AG1 -N5  -C11  -159.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         55
            N3  -C7  -C10 -N4    -14.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         56
            C6  -C7  -C10 -N4    165.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         57
            N7  -C17 -C20 -N8    -11.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         58
            C16 -C17 -C20 -N8    167.00  4.00   1.555   1.555   1.555   1.555
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         10

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  19 ALERT level G = General information/check it is not something unexpected

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

Comment top

Cyano, carboxylate, pyridyl and triazole groups have been widely employed as organic linkers to bond with metal ions to construct subtile metal organic frameworks (MOFs) (Wang et al. 2009; Manriquez et al. 1991). Many 2,2'-bipyridine derivatives together with their various metal complexes have also been synthesized and well characterized (Berghian et al. 2005; Mathieu et al. 2001).

Herein, we present the structure of a new complex [Ag(C₁₀H₆N₄)₂]ClO₄ derived from 5-(2-pyridyl)pyrazine-2-carbonitrile, a similar ligand to the 2,2'-bipyridine featuring a 2-cyanopyrazinyl group bonding to the 2-pyridyl carbon atom (Scheme 1). As shown in Fig. 1, the two ligands around the central Ag^I ion are in an anti-relationship and almost in the same plane, thus the Ag^I ion is surrounded by two 2-pyridyl N atoms and two 2-pyrazinyl N atoms. The Ag1—N1(pyridyl) and Ag1—N5(pyridyl) bonds are 2.184 (2) and 2.193 (2) Å, respectively. Meanwhile, the longer Ag1—N6(pyrazinyl) and Ag1—N2(pyrazinyl) distances are 2.684 (2) Å and 2.739 (3) Å, respectively. The Ag—N bond lengths are similar to those (2.196 (2)–2.685 (2) Å) in the isomorphous mononuclear structure of [Ag(C₁₀H₆N₄)₂]BF₄ reported by us recently (Wang et al., 2010). Also, the longer Ag—N(pyrazinyl) distance is comparable to that in [Ag(dafone)₂]NO₃.H₂O (dafone = 4,5-diazafluoren-9-one) (Biju & Rajasekharan, 2008). If the weak Ag···N contact is included, a planar N4-square coordination geometry is formed. The perchlorate anions function as linkages to link neighboring [Ag(C₁₀H₆N₄)₂]⁺ moieties arranged along the [110] direction into an infinite tape structure through C—H···O interactions (Table 1, Fig. 2). The tapes are stacked along the [110] direction and interconnect via π–π interactions. The Cg1(pyridyl)···Cg1ⁱ(pyridyl) and Cg2(pyridyl)···Cg2ⁱⁱ(pyridyl) distances are 3.777 (3) and 3.879 (2) Å, respectively, while that of Cg3(pyrazinyl)···Cg3ⁱⁱⁱ(pyrazinyl) is 3.626 (2) Å (symmetry codes: I –x + 1, –y + 1, –z + 1; ii –x + 1, –y + 2, –z + 2; iii –x + 1, –y + 2, –z + 1. Cg1, Cg2, Cg3 represent the N1-C1-C2-C3-C4-C5, N5-C11-C12-C13-C14-C15 and N2-C6-C7-N3-C8-C9 rings, respectively). A three-dimensional supramolecular framework is formed (Fig. 3).

Related literature top

For coordination complexes with cyano, carboxylate, pyridyl and triazole groups, see: Wang et al. (2009); Manriquez et al. (1991). For these involving 2,2'-bipyridine derivatives, see: Berghian et al. (2005); Mathieu et al. (2001). For comparable structures, see: Biju & Rajasekharan (2008); Wang et al. (2010).

Experimental top

The ligand 5-(2-pyridyl)-2-cyanopyrazine was obtained commercially. To a clear solution of 3 ml methanol containing the ligand (18.2 mg, 0.1 mmol), AgClO₄ (22 mg, 0.1mmol) was added with stirring at room temperature. 1 ml acetonitrile was subsequently added dropwise to make the solution clear. After filtration the clear solution was kept in air for one week at room temperature to yield colorless rod-like crystals (19.0 mg, 66% yeild).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The atom-numbering scheme of the title [Ag(C10H6N4)2]ClO4. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The perchlorate linkages between the [Ag(C₁₀H₆N₄)₂]⁺ moieties arranged along the [110] direction. The red-dashed lines indicate the C—H···O(perchlorate) Hydrogen-bonding interactions, while the purple balls represent the Ag^I ions. Symmetry codes: i –x + 2, –y + 2, –z + 1; ii –x + 1, –y + 1, –z + 1.
	Fig. 3. View down the c axis of the three-dimensional supramolecular structure of the title complex. All non-covalent interactions are omitted for clarity.

Bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile- κ²N⁴,N⁵]silver(I) perchlorate top

Crystal data top

[Ag(C₁₀H₆N₄)₂]ClO₄	Z = 2
M_r = 571.70	F(000) = 568
Triclinic, P1	D_x = 1.821 Mg m⁻³
a = 7.8804 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3152 (14) Å	Cell parameters from 233 reflections
c = 12.3317 (14) Å	θ = 1.7–28.2°
α = 104.015 (2)°	µ = 1.14 mm⁻¹
β = 92.015 (2)°	T = 293 K
γ = 101.171 (2)°	Rod, colorless
V = 1042.8 (2) Å³	0.30 × 0.20 × 0.12 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5075 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.577, T_max = 0.755	k = −15→10
7304 measured reflections	l = −16→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0409P)² + 0.4461P] where P = (F_o² + 2F_c²)/3
5075 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.54 e Å⁻³
10 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Ag(C₁₀H₆N₄)₂]ClO₄	γ = 101.171 (2)°
M_r = 571.70	V = 1042.8 (2) Å³
Triclinic, P1	Z = 2
a = 7.8804 (10) Å	Mo Kα radiation
b = 11.3152 (14) Å	µ = 1.14 mm⁻¹
c = 12.3317 (14) Å	T = 293 K
α = 104.015 (2)°	0.30 × 0.20 × 0.12 mm
β = 92.015 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5075 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3882 reflections with I > 2σ(I)
T_min = 0.577, T_max = 0.755	R_int = 0.021
7304 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	10 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.54 e Å⁻³
5075 reflections	Δρ_min = −0.31 e Å⁻³
307 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.50428 (3)	0.75075 (2)	0.705977 (16)	0.05505 (10)
C1	0.3777 (3)	0.6399 (2)	0.45026 (19)	0.0332 (5)
C2	0.2969 (4)	0.5507 (3)	0.3561 (2)	0.0460 (6)
H2A	0.3090	0.5652	0.2854	0.055*
C3	0.1978 (4)	0.4399 (3)	0.3670 (3)	0.0519 (7)
H3A	0.1420	0.3794	0.3042	0.062*
C4	0.1834 (4)	0.4209 (3)	0.4728 (3)	0.0519 (7)
H4A	0.1166	0.3478	0.4832	0.062*
C5	0.2700 (4)	0.5124 (3)	0.5623 (2)	0.0490 (7)
H5A	0.2616	0.4985	0.6334	0.059*
N1	0.3662 (3)	0.6209 (2)	0.55367 (17)	0.0380 (5)
C6	0.7085 (3)	0.9257 (2)	0.5006 (2)	0.0392 (6)
H6A	0.8006	0.9708	0.5527	0.047*
C7	0.6760 (3)	0.9659 (2)	0.4053 (2)	0.0369 (5)
N3	0.5409 (3)	0.9082 (2)	0.32982 (17)	0.0391 (5)
C9	0.4813 (3)	0.7606 (2)	0.43988 (19)	0.0323 (5)
N2	0.6093 (3)	0.8232 (2)	0.51831 (16)	0.0371 (5)
C8	0.4446 (3)	0.8066 (2)	0.3479 (2)	0.0367 (5)
H8A	0.3490	0.7641	0.2977	0.044*
C11	0.6248 (3)	0.8669 (2)	0.96211 (18)	0.0329 (5)
C12	0.7024 (4)	0.9591 (3)	1.0561 (2)	0.0411 (6)
H12A	0.6862	0.9473	1.1274	0.049*
C13	0.8034 (4)	1.0681 (3)	1.0438 (2)	0.0451 (6)
H13A	0.8560	1.1306	1.1063	0.054*
C14	0.8250 (4)	1.0828 (3)	0.9377 (2)	0.0500 (7)
H14A	0.8927	1.1552	0.9266	0.060*
C15	0.7445 (4)	0.9883 (3)	0.8481 (2)	0.0519 (7)
H15A	0.7598	0.9990	0.7764	0.062*
N5	0.6457 (3)	0.8821 (2)	0.85757 (17)	0.0410 (5)
C16	0.2892 (4)	0.5835 (2)	0.9077 (2)	0.0435 (6)
H16A	0.2074	0.5338	0.8504	0.052*
C17	0.2979 (3)	0.5534 (2)	1.0099 (2)	0.0372 (5)
C18	0.5251 (3)	0.7139 (3)	1.0743 (2)	0.0400 (6)
H18A	0.6126	0.7593	1.1296	0.048*
C19	0.5123 (3)	0.7507 (2)	0.97452 (18)	0.0322 (5)
N6	0.3962 (3)	0.6827 (2)	0.89007 (17)	0.0408 (5)
N7	0.4176 (3)	0.6168 (2)	1.09313 (17)	0.0418 (5)
C10	0.7861 (4)	1.0716 (3)	0.3789 (2)	0.0464 (6)
N4	0.8670 (4)	1.1518 (3)	0.3512 (2)	0.0716 (8)
C20	0.1815 (4)	0.4486 (3)	1.0339 (2)	0.0443 (6)
N8	0.0976 (4)	0.3679 (3)	1.0585 (2)	0.0603 (7)
Cl1	0.94869 (8)	0.75080 (6)	0.28153 (5)	0.03921 (15)
O3	1.0442 (3)	0.6770 (2)	0.20672 (19)	0.0635 (6)
O4	0.7780 (3)	0.6817 (2)	0.28566 (19)	0.0590 (5)
O1	1.0367 (3)	0.7906 (3)	0.39031 (19)	0.0854 (9)
O2	0.9306 (4)	0.8567 (2)	0.2423 (3)	0.0870 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.07966 (19)	0.05148 (15)	0.02647 (11)	0.00307 (12)	−0.00799 (10)	0.00575 (9)
C1	0.0370 (12)	0.0342 (12)	0.0289 (11)	0.0064 (10)	0.0016 (9)	0.0099 (10)
C2	0.0593 (17)	0.0446 (15)	0.0304 (12)	0.0041 (13)	−0.0068 (11)	0.0091 (11)
C3	0.0600 (18)	0.0374 (15)	0.0489 (16)	−0.0027 (13)	−0.0132 (13)	0.0056 (12)
C4	0.0540 (17)	0.0401 (15)	0.0598 (18)	−0.0018 (13)	−0.0004 (14)	0.0193 (14)
C5	0.0591 (17)	0.0481 (16)	0.0400 (14)	0.0006 (14)	0.0055 (13)	0.0193 (13)
N1	0.0451 (12)	0.0390 (12)	0.0289 (10)	0.0022 (9)	0.0030 (9)	0.0117 (9)
C6	0.0460 (14)	0.0367 (13)	0.0292 (12)	−0.0005 (11)	−0.0004 (10)	0.0050 (10)
C7	0.0488 (14)	0.0298 (12)	0.0313 (12)	0.0067 (11)	0.0096 (10)	0.0066 (10)
N3	0.0446 (12)	0.0408 (12)	0.0325 (10)	0.0070 (10)	0.0033 (9)	0.0121 (9)
C9	0.0372 (12)	0.0334 (12)	0.0262 (11)	0.0077 (10)	0.0068 (9)	0.0065 (9)
N2	0.0467 (12)	0.0356 (11)	0.0253 (9)	0.0030 (9)	0.0006 (8)	0.0059 (8)
C8	0.0366 (13)	0.0405 (14)	0.0332 (12)	0.0054 (11)	0.0011 (10)	0.0120 (10)
C11	0.0368 (12)	0.0357 (12)	0.0254 (11)	0.0056 (10)	0.0014 (9)	0.0082 (9)
C12	0.0528 (15)	0.0419 (14)	0.0263 (11)	0.0048 (12)	−0.0005 (10)	0.0088 (10)
C13	0.0519 (16)	0.0398 (14)	0.0368 (13)	0.0011 (12)	−0.0043 (11)	0.0046 (11)
C14	0.0541 (16)	0.0428 (15)	0.0477 (16)	−0.0068 (13)	0.0048 (13)	0.0148 (13)
C15	0.0649 (18)	0.0529 (17)	0.0338 (14)	−0.0052 (14)	0.0080 (13)	0.0169 (13)
N5	0.0500 (12)	0.0434 (12)	0.0256 (10)	−0.0018 (10)	0.0025 (9)	0.0105 (9)
C16	0.0543 (16)	0.0384 (14)	0.0308 (12)	−0.0020 (12)	−0.0032 (11)	0.0057 (11)
C17	0.0410 (13)	0.0353 (13)	0.0347 (12)	0.0074 (11)	0.0080 (10)	0.0078 (10)
C18	0.0428 (14)	0.0448 (15)	0.0299 (12)	−0.0008 (11)	−0.0004 (10)	0.0133 (11)
C19	0.0373 (12)	0.0346 (12)	0.0239 (10)	0.0075 (10)	0.0030 (9)	0.0059 (9)
N6	0.0534 (13)	0.0370 (12)	0.0271 (10)	−0.0004 (10)	−0.0008 (9)	0.0070 (9)
N7	0.0473 (12)	0.0455 (13)	0.0320 (11)	0.0027 (10)	0.0029 (9)	0.0140 (10)
C10	0.0627 (17)	0.0367 (14)	0.0330 (13)	−0.0002 (13)	0.0008 (12)	0.0051 (11)
N4	0.104 (2)	0.0470 (16)	0.0509 (16)	−0.0174 (16)	0.0052 (15)	0.0140 (13)
C20	0.0489 (15)	0.0419 (15)	0.0389 (14)	0.0029 (12)	0.0045 (12)	0.0092 (12)
N8	0.0701 (17)	0.0492 (15)	0.0560 (16)	−0.0049 (13)	0.0054 (13)	0.0166 (13)
Cl1	0.0416 (3)	0.0371 (3)	0.0345 (3)	0.0008 (3)	0.0034 (2)	0.0066 (2)
O3	0.0616 (13)	0.0711 (15)	0.0531 (13)	0.0254 (12)	0.0021 (10)	−0.0022 (11)
O4	0.0473 (11)	0.0565 (13)	0.0687 (14)	−0.0064 (10)	0.0009 (10)	0.0215 (11)
O1	0.0658 (15)	0.121 (2)	0.0418 (12)	−0.0060 (15)	−0.0094 (11)	−0.0089 (14)
O2	0.0997 (19)	0.0640 (16)	0.126 (2)	0.0313 (14)	0.0595 (18)	0.0591 (17)

Geometric parameters (Å, º) top

Ag1—N1	2.184 (2)	C11—C12	1.387 (3)
Ag1—N5	2.193 (2)	C11—C19	1.481 (3)
Ag1—N6	2.683 (2)	C12—C13	1.378 (4)
Ag1—N2	2.739 (2)	C12—H12A	0.9300
C1—N1	1.347 (3)	C13—C14	1.371 (4)
C1—C2	1.379 (4)	C13—H13A	0.9300
C1—C9	1.486 (3)	C14—C15	1.372 (4)
C2—C3	1.382 (4)	C14—H14A	0.9300
C2—H2A	0.9300	C15—N5	1.333 (3)
C3—C4	1.378 (4)	C15—H15A	0.9300
C3—H3A	0.9300	C16—N6	1.335 (3)
C4—C5	1.369 (4)	C16—C17	1.386 (3)
C4—H4A	0.9300	C16—H16A	0.9300
C5—N1	1.342 (3)	C17—N7	1.331 (3)
C5—H5A	0.9300	C17—C20	1.450 (4)
C6—N2	1.337 (3)	C18—N7	1.325 (3)
C6—C7	1.392 (3)	C18—C19	1.397 (3)
C6—H6A	0.9300	C18—H18A	0.9300
C7—N3	1.339 (3)	C19—N6	1.336 (3)
C7—C10	1.447 (4)	C10—N4	1.135 (4)
N3—C8	1.321 (3)	C20—N8	1.131 (4)
C9—N2	1.333 (3)	Cl1—O1	1.416 (2)
C9—C8	1.401 (3)	Cl1—O2	1.426 (2)
C8—H8A	0.9300	Cl1—O3	1.426 (2)
C11—N5	1.353 (3)	Cl1—O4	1.428 (2)

N1—Ag1—N5	179.23 (7)	C13—C12—H12A	120.0
N1—C1—C2	121.7 (2)	C11—C12—H12A	120.0
N1—C1—C9	117.9 (2)	C14—C13—C12	118.7 (3)
C2—C1—C9	120.4 (2)	C14—C13—H13A	120.7
C1—C2—C3	119.9 (2)	C12—C13—H13A	120.7
C1—C2—H2A	120.1	C13—C14—C15	118.6 (3)
C3—C2—H2A	120.1	C13—C14—H14A	120.7
C4—C3—C2	118.7 (3)	C15—C14—H14A	120.7
C4—C3—H3A	120.7	N5—C15—C14	124.0 (2)
C2—C3—H3A	120.7	N5—C15—H15A	118.0
C5—C4—C3	118.3 (3)	C14—C15—H15A	118.0
C5—C4—H4A	120.9	C15—N5—C11	117.7 (2)
C3—C4—H4A	120.9	C15—N5—Ag1	118.68 (17)
N1—C5—C4	124.0 (3)	C11—N5—Ag1	123.31 (17)
N1—C5—H5A	118.0	N6—C16—C17	121.1 (2)
C4—C5—H5A	118.0	N6—C16—H16A	119.5
C5—N1—C1	117.5 (2)	C17—C16—H16A	119.5
C5—N1—Ag1	118.25 (17)	N7—C17—C16	122.4 (2)
C1—N1—Ag1	124.21 (17)	N7—C17—C20	114.5 (2)
N2—C6—C7	121.0 (2)	C16—C17—C20	123.0 (2)
N2—C6—H6A	119.5	N7—C18—C19	122.6 (2)
C7—C6—H6A	119.5	N7—C18—H18A	118.7
N3—C7—C6	122.3 (2)	C19—C18—H18A	118.7
N3—C7—C10	114.7 (2)	N6—C19—C18	120.4 (2)
C6—C7—C10	123.0 (2)	N6—C19—C11	119.3 (2)
C8—N3—C7	116.1 (2)	C18—C19—C11	120.3 (2)
N2—C9—C8	120.9 (2)	C16—N6—C19	117.3 (2)
N2—C9—C1	119.2 (2)	C18—N7—C17	116.1 (2)
C8—C9—C1	119.9 (2)	N4—C10—C7	175.5 (3)
C9—N2—C6	117.1 (2)	N8—C20—C17	175.7 (3)
N3—C8—C9	122.4 (2)	O1—Cl1—O2	109.5 (2)
N3—C8—H8A	118.8	O1—Cl1—O3	109.86 (16)
C9—C8—H8A	118.8	O2—Cl1—O3	109.58 (15)
N5—C11—C12	121.1 (2)	O1—Cl1—O4	109.76 (14)
N5—C11—C19	118.5 (2)	O2—Cl1—O4	107.38 (15)
C12—C11—C19	120.4 (2)	O3—Cl1—O4	110.68 (14)
C13—C12—C11	120.0 (2)

N1—C1—C2—C3	1.5 (4)	C11—C12—C13—C14	0.0 (4)
C9—C1—C2—C3	−178.6 (3)	C12—C13—C14—C15	0.2 (5)
C1—C2—C3—C4	−0.5 (5)	C13—C14—C15—N5	0.0 (5)
C2—C3—C4—C5	−0.8 (5)	C14—C15—N5—C11	−0.4 (5)
C3—C4—C5—N1	1.2 (5)	C14—C15—N5—Ag1	173.3 (2)
C4—C5—N1—C1	−0.2 (4)	C12—C11—N5—C15	0.6 (4)
C4—C5—N1—Ag1	−177.0 (2)	C19—C11—N5—C15	178.6 (2)
C2—C1—N1—C5	−1.2 (4)	C12—C11—N5—Ag1	−172.76 (19)
C9—C1—N1—C5	178.9 (2)	C19—C11—N5—Ag1	5.3 (3)
C2—C1—N1—Ag1	175.5 (2)	N1—Ag1—N5—C15	28 (6)
C9—C1—N1—Ag1	−4.4 (3)	N1—Ag1—N5—C11	−159 (6)
N5—Ag1—N1—C5	151 (6)	N6—C16—C17—N7	−3.6 (4)
N5—Ag1—N1—C1	−26 (6)	N6—C16—C17—C20	178.4 (3)
N2—C6—C7—N3	3.0 (4)	N7—C18—C19—N6	−4.7 (4)
N2—C6—C7—C10	−176.0 (2)	N7—C18—C19—C11	174.1 (2)
C6—C7—N3—C8	−3.3 (4)	N5—C11—C19—N6	−19.7 (3)
C10—C7—N3—C8	175.8 (2)	C12—C11—C19—N6	158.4 (2)
N1—C1—C9—N2	26.0 (3)	N5—C11—C19—C18	161.5 (2)
C2—C1—C9—N2	−153.9 (2)	C12—C11—C19—C18	−20.5 (4)
N1—C1—C9—C8	−154.5 (2)	C17—C16—N6—C19	0.5 (4)
C2—C1—C9—C8	25.6 (4)	C18—C19—N6—C16	3.4 (4)
C8—C9—N2—C6	−5.1 (3)	C11—C19—N6—C16	−175.4 (2)
C1—C9—N2—C6	174.4 (2)	C19—C18—N7—C17	1.6 (4)
C7—C6—N2—C9	1.4 (4)	C16—C17—N7—C18	2.4 (4)
C7—N3—C8—C9	−0.5 (4)	C20—C17—N7—C18	−179.4 (2)
N2—C9—C8—N3	4.9 (4)	N3—C7—C10—N4	−14 (4)
C1—C9—C8—N3	−174.6 (2)	C6—C7—C10—N4	165 (4)
N5—C11—C12—C13	−0.4 (4)	N7—C17—C20—N8	−11 (4)
C19—C11—C12—C13	−178.4 (2)	C16—C17—C20—N8	167 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.93	2.71	3.203 (2)	114
C14—H14A···O2ⁱ	0.93	2.54	3.103 (2)	119
C5—H5A···O4ⁱⁱ	0.93	2.45	3.193 (3)	137

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₆N₄)₂]ClO₄
M_r	571.70
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8804 (10), 11.3152 (14), 12.3317 (14)
α, β, γ (°)	104.015 (2), 92.015 (2), 101.171 (2)
V (Å³)	1042.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.30 × 0.20 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.577, 0.755
No. of measured, independent and observed [I > 2σ(I)] reflections	7304, 5075, 3882
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.03
No. of reflections	5075
No. of parameters	307
No. of restraints	10
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.31

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ag1—N1	2.184 (2)	Ag1—N6	2.683 (2)
Ag1—N5	2.193 (2)	Ag1—N2	2.739 (2)