(1H-Benzimidazole-5-carb­oxy­lic acid-κN3)(1H-benzimidazole-6-carb­oxy­lic acid-κN3)silver(I) perchlorate

Ma, L.; Huang, Y.-H.; Xu, J.-F.; Deng, H.

doi:10.1107/S1600536811010427

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m494-m495

doi:10.1107/S1600536811010427

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(1H-Benzimidazole-5-carboxylic acid-κN³)(1H-benzimidazole-6-carboxylic acid-κN³)silver(I) perchlorate

Li Ma,^a Yu-Hua Huang,^a Jian-Feng Xu ^a and Hong Deng ^a ^*

^aSchool of Chemistry and Environment, South China Nomal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: dh@scnu.edu.cn

(Received 8 March 2011; accepted 20 March 2011; online 26 March 2011)

The reaction of 1H-benzimidazole-5-carboxylic acid with silver nitrate in the presence of perchloric acid under hydrothermal conditions yielded the title complex, [Ag(C₈H₆N₂O₂)₂]ClO₄, which comprises of an [Ag(C₈H₆N₂O₂)₂] mononuclear cation and a perchlorate anion. The Ag^I ion is coordinated by two N atoms from two different neutral 1H-benzimidazole-5-carboxylic acid ligands with an N—Ag—N bond angle of 163.21 (14)°, forming an [Ag(C₈H₆N₂O₂)₂] mononuclear cation. Although both ligands in the mononuclear cation are monodentate with one N atom coordinated to the metal ion, they are different: one is N³ coordinated to the Ag ^I ion and the N¹ atom protonated, the other with the N¹ coordinated to the Ag ^I ion and the N³ atom protonated (and thus formally a 1H-benzimidazole-6-carboxylic acid rather than a 1H-benzimidazole-5-carboxylic acid ligand). The planes of the two planar ligands are roughly perpendicular, making a dihedral angle of 84.97 (2)°. The packing of the ions is stablized by extensive O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, and by remote Ag⋯O interactions [3.002 (3), 3.581 (5) and 3.674 (5) Å].

Related literature

For related structures, see: Guo, Cao et al. (2007 ); Guo, Li et al. (2007 ); Liu et al. (2005 ); Peng, Ma et al. (2010 ); Peng, Qiu et al. (2010 ). For graph-set motifs of hydrogen bonds, see: Bernstein et al. (1995 ); Eppel & Bernstein (2008 ); Grell et al. (1999 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

[Ag(C₈H₆N₂O₂)₂]ClO₄
M_r = 531.62
Triclinic, $[P \overline 1]$
a = 4.933 (2) Å
b = 13.330 (5) Å
c = 14.498 (6) Å
α = 78.566 (5)°
β = 89.111 (5)°
γ = 82.554 (5)°
V = 926.5 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 296 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.746, T_max = 0.774
4604 measured reflections
3247 independent reflections
2630 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.103
S = 1.04
3247 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.82	1.82	2.634 (5)	173
N2—H2⋯O5ⁱⁱ	0.86	2.15	2.983 (6)	163
O3—H3⋯O4ⁱⁱⁱ	0.82	1.80	2.608 (6)	168
N4—H4A⋯O6^iv	0.86	2.14	2.935 (6)	153
C14—H14⋯O1^v	0.93	2.60	3.491 (6)	162
C15—H15⋯O2^vi	0.93	2.51	3.398 (5)	161
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+3, -y+2, -z+1; (iv) -x+1, -y+2, -z+1; (v) -x+1, -y+1, -z+1; (vi) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010427/zl2355sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010427/zl2355Isup2.hkl

checkCIF report

Comment top

In recent years, N-heterocyclic carboxylic acids as organic ligands attracted significant attention not only due to their versatile coordination modes but also because of their ability to facilitate the formation of high-dimensional coordination compounds. 1H-benzimidazole-5-carboxylic acid is such an organic ligand, with four donor atoms (two N and two O atoms) and variable coordination modes. As a potential multidentate ligand, 1H-benzimidazole-5-carboxylic acid is an excellent candidate for the construction of three-dimensional architectures. Up to this date, reported compounds based on this ligand are still quite rare, but have recently started to attract some interest (Guo, Cao et al. (2007); Guo, Li et al. (2007); Liu et al. (2005); Peng, Ma et al. (2010); Peng, Qiu et al. (2010).). According to these precedents in the literature and experience, the nature of the final metal coordination framework is still hard to predict. To gain more insight into this system we thus chose 1H-benzimidazole-5-carboxylic acid and silver nitrate in a 1:1 ratio in the presence of perchloric acid under hydrothermal conditions to construct a new framework. Herein, we report an Ag coordination complex salt based on this ligand, namely [Ag(C₈H₆N₂O₂)₂].ClO₄, with a three-dimensional supramolecular network created by O—H···O, N—H···O, and C—H···O hydrogen bonds, and by Ag···O interactions [3.002 (3), 3.581 (5) and 3.674 (5) Å].

As shown in Figure 1, the title compound contains an Ag^I ion, two silver coordinated different neutral 1H-benzimidazole-5-carboxylic acid ligands and a perchlorate anion. The Ag^I ion is coordinated by two N atoms from two different 1H-benzimidazole-5-carboxylic acid ligands with Ag—N bond lengths of 2.106 (4) Å, and an N—Ag—N bond angle 163.23 °. Although both of the two ligands in the mononuclear cation are monodentate ligands with one nitrogen atom coordinated to the metal ion, they are different: one with the N³ coordinated to the Ag ^I ion and the N¹ atom protonated, the other with the N¹ coordinated to the Ag ^I ion and the N³ atom protonated (and thus formally a 1H-benzimidazole -6-carboxylic acid rather than a 1H-benzimidazole-5-carboxylic acid ligand), thus forming a mononuclear [Ag(C₈H₆N₂O₂)₂] cation.

Adjacent [Ag(C₈H₆N₂O₂)₂] mononuclear cations are linked to each other through O—H···O hydrogen bonds with the R²₂8 graph set motif typical for carboxylic acids (Bernstein et al. (1995); Eppel & Bernstein (2008); Grell et al. (1999)) to form a ribbon-like chain of [Ag(C₈H₆N₂O₂)₂] units that stretch along the (1 1 0) direction of the structure (Figure 2). Adjacent chains are further linked to each other by weak C—H···O hydrogen bonds leading to the formation of layers of [Ag(C₈H₆N₂O₂)₂] cations. The perchlorate anions are bonded to these layers through strong N—H···O hydrogen bonds originating from the imidazole rings, and through short O···Ag interactions (Figure 3). The O6···Ag, O7···Ag, O8···Ag, distances are 3.002 (3), 3.581 (5), 3.674 (5) Å, respectively, which is shorter than the sum of the van der Waals radii for silver and oxygen atoms (3.91 Å) (Bondi (1964)).

Related literature top

For related structures, see: Guo, Cao et al. (2007); Guo, Li et al. (2007); Liu et al. (2005); Peng, Ma et al. (2010); Peng, Qiu et al. (2010). For graph-set motifs of hydrogen bonds, see: Bernstein et al. (1995); Eppel & Bernstein (2008); Grell et al. (1999). For van der Waals radii, see: Bondi (1964).

Experimental top

An aqueous mixture (10 ml) of 1H-benzimidazole-5-carboxylic acid (0.05 g 0.3 mmol), silver nitrate (0.05 g 0.3 mmol) and perchloric acid (pH=2) was placed in a 23 ml Teflon-lined stainless-steel autoclave, heated to 443 K for 3 days, then cooled to room temperature at 5 K/h. Yellow prism-shaped single crystals were collected (yield 0.06 g, 0.1 mmol, 75% based on 1H-benzimidazole-5-carboxylic acid).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids.
	Fig. 2. One of the ribbon like [Ag(C₈H₆N₂O₂)₂] chains linked by O—H···O hydrogen bonds along the (1 1 0) direction.
	Fig. 3. A packing view of title compound along the a axis, showing the O—H···O, O—H···N and C—H···O hydrogen bonds and the Ag···O interactions.

(1H-Benzimidazole-5-carboxylic acid-κN³)(1H- benzimidazole-6-carboxylic acid-κN³)silver(I) perchlorate top

Crystal data top

[Ag(C₈H₆N₂O₂)₂]ClO₄	Z = 2
M_r = 531.62	F(000) = 528.0
Triclinic, P1	D_x = 1.906 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.933 (2) Å	Cell parameters from 3317 reflections
b = 13.330 (5) Å	θ = 1.6–25.2°
c = 14.498 (6) Å	µ = 1.29 mm⁻¹
α = 78.566 (5)°	T = 296 K
β = 89.111 (5)°	Prism, yellow
γ = 82.554 (5)°	0.26 × 0.24 × 0.22 mm
V = 926.5 (6) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3247 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 25.2°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.746, T_max = 0.774	k = −15→13
4604 measured reflections	l = −16→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0581P)² + 0.3563P] where P = (F_o² + 2F_c²)/3
3247 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[Ag(C₈H₆N₂O₂)₂]ClO₄	γ = 82.554 (5)°
M_r = 531.62	V = 926.5 (6) Å³
Triclinic, P1	Z = 2
a = 4.933 (2) Å	Mo Kα radiation
b = 13.330 (5) Å	µ = 1.29 mm⁻¹
c = 14.498 (6) Å	T = 296 K
α = 78.566 (5)°	0.26 × 0.24 × 0.22 mm
β = 89.111 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	3247 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2630 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.774	R_int = 0.017
4604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	Δρ_max = 0.62 e Å⁻³
3247 reflections	Δρ_min = −0.70 e Å⁻³
273 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
Ag1	0.44123 (8)	0.70811 (3)	0.15898 (2)	0.04721 (15)
C1	0.6189 (10)	0.4842 (4)	0.1256 (3)	0.0466 (11)
H1	0.7430	0.5057	0.0793	0.056*
C2	0.3124 (8)	0.4843 (3)	0.2325 (3)	0.0346 (9)
C3	0.3830 (9)	0.3825 (3)	0.2238 (3)	0.0408 (10)
C4	0.2654 (10)	0.3021 (4)	0.2792 (3)	0.0509 (12)
H4	0.3152	0.2338	0.2738	0.061*
C5	0.0729 (10)	0.3286 (3)	0.3421 (3)	0.0471 (11)
H5	−0.0092	0.2766	0.3804	0.057*
C6	−0.0052 (9)	0.4309 (3)	0.3509 (3)	0.0396 (10)
C7	0.1163 (9)	0.5103 (3)	0.2959 (3)	0.0391 (10)
H7	0.0675	0.5786	0.3016	0.047*
C8	−0.2186 (10)	0.4595 (3)	0.4175 (3)	0.0446 (11)
C9	0.4393 (10)	0.9464 (4)	0.1285 (3)	0.0456 (11)
H9	0.3170	0.9604	0.0780	0.055*
C10	0.6828 (9)	0.8675 (3)	0.2492 (3)	0.0371 (10)
C11	0.7374 (9)	0.9692 (3)	0.2309 (3)	0.0381 (10)
C12	0.9185 (9)	1.0038 (3)	0.2866 (3)	0.0421 (10)
H12	0.9543	1.0719	0.2747	0.050*
C13	1.0426 (9)	0.9313 (3)	0.3608 (3)	0.0390 (10)
C14	0.9860 (10)	0.8291 (4)	0.3798 (3)	0.0482 (11)
H14	1.0709	0.7827	0.4308	0.058*
C15	0.8066 (10)	0.7964 (3)	0.3241 (3)	0.0460 (11)
H15	0.7694	0.7284	0.3364	0.055*
C16	1.2386 (10)	0.9636 (4)	0.4219 (3)	0.0457 (11)
Cl1	0.9204 (2)	0.77011 (9)	0.97296 (8)	0.0448 (3)
N1	0.4642 (7)	0.5474 (3)	0.1693 (2)	0.0408 (9)
N2	0.5791 (8)	0.3854 (3)	0.1548 (3)	0.0493 (10)
H2	0.6610	0.3333	0.1343	0.059*
N3	0.4956 (8)	0.8550 (3)	0.1829 (2)	0.0415 (9)
N4	0.5779 (8)	1.0176 (3)	0.1536 (3)	0.0470 (9)
H4A	0.5686	1.0815	0.1264	0.056*
O1	−0.3280 (8)	0.3835 (2)	0.4671 (3)	0.0581 (9)
H1A	−0.4557	0.4062	0.4972	0.087*
O2	−0.2846 (7)	0.5503 (2)	0.4241 (2)	0.0608 (10)
O3	1.3333 (8)	0.8956 (3)	0.4925 (3)	0.0672 (10)
H3	1.4522	0.9178	0.5187	0.101*
O4	1.3026 (8)	1.0534 (3)	0.4028 (2)	0.0630 (10)
O5	1.0476 (7)	0.7959 (3)	0.8839 (2)	0.0603 (9)
O6	0.6290 (6)	0.7811 (3)	0.9620 (2)	0.0577 (9)
O7	1.0171 (10)	0.6657 (4)	1.0117 (4)	0.1079 (18)
O8	0.9910 (9)	0.8361 (5)	1.0309 (4)	0.117 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0531 (3)	0.0393 (2)	0.0526 (2)	−0.01424 (16)	0.00379 (16)	−0.01219 (16)
C1	0.042 (3)	0.052 (3)	0.049 (3)	−0.009 (2)	0.008 (2)	−0.013 (2)
C2	0.031 (2)	0.035 (2)	0.038 (2)	−0.0045 (17)	−0.0032 (17)	−0.0080 (18)
C3	0.043 (3)	0.039 (2)	0.043 (2)	−0.005 (2)	0.0001 (19)	−0.014 (2)
C4	0.060 (3)	0.033 (2)	0.060 (3)	−0.004 (2)	0.006 (2)	−0.013 (2)
C5	0.056 (3)	0.035 (2)	0.050 (3)	−0.013 (2)	0.006 (2)	−0.005 (2)
C6	0.039 (3)	0.038 (2)	0.040 (2)	−0.0033 (19)	−0.0002 (19)	−0.0044 (19)
C7	0.041 (3)	0.031 (2)	0.046 (2)	−0.0022 (19)	0.0006 (19)	−0.0109 (19)
C8	0.047 (3)	0.038 (3)	0.047 (3)	−0.008 (2)	0.005 (2)	−0.002 (2)
C9	0.048 (3)	0.048 (3)	0.042 (2)	−0.006 (2)	−0.003 (2)	−0.013 (2)
C10	0.038 (3)	0.037 (2)	0.037 (2)	−0.0034 (19)	0.0048 (18)	−0.0102 (18)
C11	0.041 (3)	0.035 (2)	0.038 (2)	−0.0028 (19)	−0.0024 (19)	−0.0081 (18)
C12	0.047 (3)	0.034 (2)	0.045 (3)	−0.005 (2)	−0.003 (2)	−0.007 (2)
C13	0.035 (2)	0.041 (2)	0.040 (2)	−0.0063 (19)	0.0032 (18)	−0.0078 (19)
C14	0.057 (3)	0.043 (3)	0.040 (3)	−0.001 (2)	−0.004 (2)	−0.001 (2)
C15	0.057 (3)	0.032 (2)	0.049 (3)	−0.008 (2)	−0.001 (2)	−0.006 (2)
C16	0.048 (3)	0.051 (3)	0.038 (2)	−0.002 (2)	0.000 (2)	−0.010 (2)
Cl1	0.0334 (6)	0.0542 (7)	0.0455 (6)	−0.0021 (5)	−0.0026 (5)	−0.0084 (5)
N1	0.041 (2)	0.038 (2)	0.044 (2)	−0.0047 (17)	0.0058 (16)	−0.0087 (17)
N2	0.055 (3)	0.040 (2)	0.056 (2)	−0.0027 (18)	0.0131 (19)	−0.0196 (18)
N3	0.046 (2)	0.037 (2)	0.043 (2)	−0.0096 (17)	0.0016 (16)	−0.0109 (17)
N4	0.058 (3)	0.033 (2)	0.047 (2)	−0.0052 (18)	−0.0090 (18)	−0.0014 (17)
O1	0.059 (2)	0.0433 (19)	0.068 (2)	−0.0067 (16)	0.0241 (17)	−0.0017 (16)
O2	0.071 (3)	0.0371 (19)	0.071 (2)	−0.0037 (17)	0.0301 (19)	−0.0084 (16)
O3	0.079 (3)	0.066 (2)	0.054 (2)	−0.016 (2)	−0.0255 (19)	−0.0008 (19)
O4	0.072 (3)	0.054 (2)	0.064 (2)	−0.0176 (19)	−0.0196 (18)	−0.0074 (18)
O5	0.060 (2)	0.067 (2)	0.052 (2)	−0.0115 (19)	0.0080 (16)	−0.0069 (17)
O6	0.0317 (18)	0.064 (2)	0.075 (2)	−0.0046 (16)	−0.0046 (15)	−0.0080 (18)
O7	0.077 (3)	0.087 (3)	0.125 (4)	0.011 (3)	0.004 (3)	0.051 (3)
O8	0.060 (3)	0.199 (6)	0.128 (4)	−0.023 (3)	0.010 (3)	−0.120 (4)

Geometric parameters (Å, º) top

Ag1—N1	2.106 (4)	C10—C15	1.383 (6)
Ag1—N3	2.106 (4)	C10—C11	1.390 (6)
C1—N1	1.313 (6)	C10—N3	1.391 (5)
C1—N2	1.340 (6)	C11—N4	1.379 (5)
C1—H1	0.9300	C11—C12	1.393 (6)
C2—C7	1.383 (6)	C12—C13	1.386 (6)
C2—C3	1.387 (6)	C12—H12	0.9300
C2—N1	1.394 (5)	C13—C14	1.399 (6)
C3—N2	1.379 (6)	C13—C16	1.480 (6)
C3—C4	1.392 (6)	C14—C15	1.373 (6)
C4—C5	1.368 (7)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.399 (6)	C16—O4	1.255 (6)
C5—H5	0.9300	C16—O3	1.275 (5)
C6—C7	1.390 (6)	Cl1—O8	1.408 (4)
C6—C8	1.482 (6)	Cl1—O7	1.416 (4)
C7—H7	0.9300	Cl1—O5	1.426 (4)
C8—O2	1.234 (5)	Cl1—O6	1.434 (3)
C8—O1	1.294 (5)	N2—H2	0.8600
C9—N3	1.312 (6)	N4—H4A	0.8600
C9—N4	1.348 (6)	O1—H1A	0.8200
C9—H9	0.9300	O3—H3	0.8200

N1—Ag1—N3	163.21 (14)	C13—C12—H12	121.7
N1—C1—N2	112.9 (4)	C11—C12—H12	121.7
N1—C1—H1	123.6	C12—C13—C14	121.9 (4)
N2—C1—H1	123.6	C12—C13—C16	118.8 (4)
C7—C2—C3	121.0 (4)	C14—C13—C16	119.3 (4)
C7—C2—N1	129.7 (4)	C15—C14—C13	120.8 (4)
C3—C2—N1	109.3 (4)	C15—C14—H14	119.6
N2—C3—C2	105.3 (4)	C13—C14—H14	119.6
N2—C3—C4	132.8 (4)	C14—C15—C10	118.1 (4)
C2—C3—C4	122.0 (4)	C14—C15—H15	121.0
C5—C4—C3	116.6 (4)	C10—C15—H15	121.0
C5—C4—H4	121.7	O4—C16—O3	123.8 (4)
C3—C4—H4	121.7	O4—C16—C13	120.1 (4)
C4—C5—C6	122.4 (4)	O3—C16—C13	116.1 (4)
C4—C5—H5	118.8	O8—Cl1—O7	111.1 (4)
C6—C5—H5	118.8	O8—Cl1—O5	108.7 (3)
C7—C6—C5	120.4 (4)	O7—Cl1—O5	107.5 (3)
C7—C6—C8	117.4 (4)	O8—Cl1—O6	109.9 (2)
C5—C6—C8	122.3 (4)	O7—Cl1—O6	109.1 (3)
C2—C7—C6	117.7 (4)	O5—Cl1—O6	110.6 (2)
C2—C7—H7	121.2	C1—N1—C2	105.0 (4)
C6—C7—H7	121.2	C1—N1—Ag1	131.1 (3)
O2—C8—O1	123.2 (4)	C2—N1—Ag1	123.9 (3)
O2—C8—C6	121.2 (4)	C1—N2—C3	107.5 (4)
O1—C8—C6	115.6 (4)	C1—N2—H2	126.2
N3—C9—N4	112.7 (4)	C3—N2—H2	126.2
N3—C9—H9	123.7	C9—N3—C10	105.3 (4)
N4—C9—H9	123.7	C9—N3—Ag1	130.1 (3)
C15—C10—C11	121.0 (4)	C10—N3—Ag1	121.7 (3)
C15—C10—N3	129.7 (4)	C9—N4—C11	107.4 (4)
C11—C10—N3	109.2 (4)	C9—N4—H4A	126.3
N4—C11—C10	105.4 (4)	C11—N4—H4A	126.3
N4—C11—C12	133.0 (4)	C8—O1—H1A	109.5
C10—C11—C12	121.7 (4)	C16—O3—H3	109.5
C13—C12—C11	116.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.82	2.634 (5)	173
N2—H2···O5ⁱⁱ	0.86	2.15	2.983 (6)	163
O3—H3···O4ⁱⁱⁱ	0.82	1.80	2.608 (6)	168
N4—H4A···O6^iv	0.86	2.14	2.935 (6)	153
C14—H14···O3	0.93	2.41	2.729 (6)	100
C14—H14···O1^v	0.93	2.60	3.491 (6)	162
C15—H15···O2^vi	0.93	2.51	3.398 (5)	161

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

Experimental details

Crystal data
Chemical formula	[Ag(C₈H₆N₂O₂)₂]ClO₄
M_r	531.62
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	4.933 (2), 13.330 (5), 14.498 (6)
α, β, γ (°)	78.566 (5), 89.111 (5), 82.554 (5)
V (Å³)	926.5 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.746, 0.774
No. of measured, independent and observed [I > 2σ(I)] reflections	4604, 3247, 2630
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.103, 1.04
No. of reflections	3247
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.70

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.82	2.634 (5)	173
N2—H2···O5ⁱⁱ	0.86	2.15	2.983 (6)	163
O3—H3···O4ⁱⁱⁱ	0.82	1.80	2.608 (6)	168
N4—H4A···O6^iv	0.86	2.14	2.935 (6)	153
C14—H14···O3	0.93	2.41	2.729 (6)	100
C14—H14···O1^v	0.93	2.60	3.491 (6)	162
C15—H15···O2^vi	0.93	2.51	3.398 (5)	161

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

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

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