Bis(2-phenyl-1H-imidazole-κN3)silver(I) nitrate

Han, S.; Li, W.-C.; Xia, D.-C.

doi:10.1107/S1600536809051459

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m3

doi:10.1107/S1600536809051459

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Bis(2-phenyl-1H-imidazole-κN³)silver(I) nitrate

Shuang Han,^a Wan-Cheng Li ^b and Dao-Cheng Xia ^a ^*

^aCollege of Chemistry, Yuncheng University, Yuncheng 044000, People's Republic of China, and ^bState Key Laboratory of Integrated Optoelectronics, Jilin University, Changchun 130021, People's Republic of China
^*Correspondence e-mail: hanshuang1957@yahoo.com.cn

(Received 22 November 2009; accepted 29 November 2009; online 4 December 2009)

The asymmetric unit of the title compound, [Ag(C₉H₈N₂)₂]NO₃, contains one complete [Ag(C₉H₈N₂)₂]⁺ cation and two half-cations (with the other halves generated through inversion) and two NO₃⁻ anions. Each Ag^I ion shows a linear AgN₂ coordination. The ions are linked by N—H⋯O hydrogen bonds.

Related literature

For general background to 2-phenylimidazole, see: Liu et al. (2008 ); Yang et al. (2008 ).

Experimental

Crystal data

[Ag(C₉H₈N₂)₂]NO₃
M_r = 458.23
Triclinic, $[P \overline 1]$
a = 9.209 (5) Å
b = 9.274 (5) Å
c = 23.137 (5) Å
α = 88.307 (5)°
β = 80.976 (5)°
γ = 72.369 (5)°
V = 1859.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 293 K
0.31 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.62, T_max = 0.86
14127 measured reflections
8475 independent reflections
4372 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 0.80
8475 reflections
490 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6ⁱ	0.86	2.03	2.893 (3)	178
N3—H3⋯O5ⁱⁱ	0.86	1.95	2.812 (3)	178
N6—H6⋯O2ⁱⁱⁱ	0.86	1.99	2.846 (3)	173
N7—H7⋯O1^iv	0.86	1.95	2.812 (3)	177
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+1.

Data collection: CrysAlis (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis; data reduction: CrysAlis; 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 global, I. DOI: 10.1107/S1600536809051459/ci2975sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051459/ci2975Isup2.hkl

checkCIF report

Comment top

2-Phenylimidazole, as an important N-containing ligand with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Liu et al., 2008; Yang et al., 2008). We report here the synthesis and structure of the title compound, namely, [Ag(C₉H₈N₂)₂]^.2NO₃ (I)

The asymmetric unit contains one complete and two halves of centrosymmetric [Ag(C₉H₈N₂)₂]⁺ cations and two NO₃^- anions. Atoms Ag1 and Ag3 lie on inversion centres. Each Ag^I ion in the title salt shows a linear coordination. The N—Ag—N angle is exactly 180° (by virtue of the inversion symmetry) for two cations lying across inversion centres and 175.94 (11)° for the cation on general position.

In the crystal structure, the ionic units are linked through N—H···O hydrogen bonds (Table 1)

Related literature top

For general background to 2-Phenylimidazole, see: Liu et al. (2008); Yang et al. (2008).

Experimental top

Silver nitrate (0.5 mmol, 0.085 g) and 2-phenylimidazole (0.5 mmol, 0.041 g) in water (20 mmol) was heated at 435 K for 2 d. Then the mixture was slowly cooled to room temperature to obtain colourless single crystals of the title compound (yield: 39%).

Computing details top

Data collection: CrysAlis (Oxford Diffraction, 2006); cell refinement: CrysAlis (Oxford Diffraction, 2006); data reduction: CrysAlis (Oxford Diffraction, 2006); 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 molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x, -y, 2 - z; (ii) 1 - x, 1 - y, 1 -z]

Bis(2-phenyl-1H-imidazole-κN³)silver(I) nitrate top

Crystal data top

[Ag(C₉H₈N₂)₂]NO₃	Z = 4
M_r = 458.23	F(000) = 920
Triclinic, P1	D_x = 1.637 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.209 (5) Å	Cell parameters from 8475 reflections
b = 9.274 (5) Å	θ = 3.0–29.1°
c = 23.137 (5) Å	µ = 1.11 mm⁻¹
α = 88.307 (5)°	T = 293 K
β = 80.976 (5)°	Block, colourless
γ = 72.369 (5)°	0.31 × 0.28 × 0.22 mm
V = 1859.5 (15) Å³

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	8475 independent reflections
Radiation source: fine-focus sealed tube	4372 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.0 pixels mm^-1	θ_max = 29.1°, θ_min = 1.8°
ω scan	h = −10→11
Absorption correction: multi-scan (CrysAlis; Oxford Diffraction, 2006)	k = −9→11
T_min = 0.62, T_max = 0.86	l = −23→28
14127 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 0.80	w = 1/[σ²(F_o²) + (0.04P)²] where P = (F_o² + 2F_c²)/3
8475 reflections	(Δ/σ)_max = 0.002
490 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ag(C₉H₈N₂)₂]NO₃	γ = 72.369 (5)°
M_r = 458.23	V = 1859.5 (15) Å³
Triclinic, P1	Z = 4
a = 9.209 (5) Å	Mo Kα radiation
b = 9.274 (5) Å	µ = 1.11 mm⁻¹
c = 23.137 (5) Å	T = 293 K
α = 88.307 (5)°	0.31 × 0.28 × 0.22 mm
β = 80.976 (5)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	8475 independent reflections
Absorption correction: multi-scan (CrysAlis; Oxford Diffraction, 2006)	4372 reflections with I > 2σ(I)
T_min = 0.62, T_max = 0.86	R_int = 0.029
14127 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 0.80	Δρ_max = 0.28 e Å⁻³
8475 reflections	Δρ_min = −0.43 e Å⁻³
490 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
C1	0.2039 (4)	0.7556 (4)	0.48467 (13)	0.0638 (9)
H1	0.2611	0.8103	0.4622	0.077*
C2	0.0492 (4)	0.7985 (3)	0.49731 (12)	0.0594 (8)
H2A	−0.0197	0.8856	0.4853	0.071*
C3	0.1453 (3)	0.5807 (3)	0.53886 (11)	0.0468 (7)
C4	0.1492 (3)	0.4477 (3)	0.57426 (12)	0.0519 (7)
C5	0.2697 (4)	0.3145 (4)	0.56355 (15)	0.0728 (10)
H5	0.3513	0.3085	0.5335	0.087*
C6	0.2676 (6)	0.1892 (4)	0.5984 (2)	0.1029 (15)
H6A	0.3488	0.1000	0.5917	0.123*
C7	0.1483 (7)	0.1965 (5)	0.6419 (2)	0.1033 (16)
H7A	0.1477	0.1117	0.6643	0.124*
C8	0.0300 (5)	0.3259 (5)	0.65292 (16)	0.0858 (12)
H8	−0.0514	0.3298	0.6828	0.103*
C9	0.0301 (4)	0.4525 (4)	0.61976 (13)	0.0642 (9)
H9	−0.0504	0.5417	0.6281	0.077*
C10	0.5291 (4)	0.3440 (4)	0.68802 (15)	0.0770 (10)
H10	0.5854	0.2473	0.6976	0.092*
C11	0.5840 (4)	0.4361 (4)	0.65051 (14)	0.0703 (9)
H11	0.6833	0.4156	0.6297	0.084*
C12	0.3411 (3)	0.5502 (4)	0.68619 (11)	0.0531 (8)
C13	0.1928 (3)	0.6666 (4)	0.69513 (12)	0.0535 (8)
C14	0.0864 (4)	0.6708 (4)	0.74507 (13)	0.0675 (9)
H14	0.1112	0.5999	0.7741	0.081*
C15	−0.0549 (4)	0.7784 (5)	0.75202 (16)	0.0831 (11)
H15	−0.1255	0.7793	0.7856	0.100*
C16	−0.0939 (4)	0.8843 (5)	0.71036 (19)	0.0888 (11)
H16	−0.1902	0.9570	0.7156	0.107*
C17	0.0100 (4)	0.8830 (4)	0.66062 (16)	0.0768 (10)
H17	−0.0162	0.9550	0.6321	0.092*
C18	0.1526 (4)	0.7756 (4)	0.65282 (13)	0.0629 (8)
H18	0.2225	0.7756	0.6191	0.076*
C19	−0.0449 (4)	0.2333 (4)	0.83247 (15)	0.0759 (10)
H19	−0.1031	0.3343	0.8314	0.091*
C20	−0.0945 (4)	0.1228 (4)	0.86113 (13)	0.0665 (9)
H20	−0.1908	0.1336	0.8832	0.080*
C21	0.1440 (3)	0.0264 (4)	0.81694 (11)	0.0513 (7)
C22	0.2921 (3)	−0.0865 (4)	0.79868 (11)	0.0513 (7)
C23	0.3918 (4)	−0.0679 (4)	0.74913 (12)	0.0705 (9)
H23	0.3614	0.0170	0.7263	0.085*
C24	0.5334 (4)	−0.1714 (5)	0.73331 (16)	0.0876 (12)
H24	0.5984	−0.1561	0.7003	0.105*
C25	0.5795 (4)	−0.2975 (5)	0.76602 (19)	0.0915 (12)
H25	0.6758	−0.3679	0.7552	0.110*
C26	0.4839 (4)	−0.3200 (4)	0.81467 (17)	0.0835 (11)
H26	0.5155	−0.4061	0.8368	0.100*
C27	0.3413 (4)	−0.2161 (4)	0.83117 (14)	0.0657 (9)
H27	0.2772	−0.2327	0.8643	0.079*
C28	0.3155 (4)	0.3721 (4)	0.88477 (16)	0.0765 (10)
H28	0.3069	0.4670	0.8689	0.092*
C29	0.4421 (4)	0.2525 (4)	0.86556 (14)	0.0686 (9)
H29	0.5199	0.2668	0.8372	0.082*
C30	0.4548 (3)	0.1094 (3)	0.88841 (12)	0.0566 (8)
H30	0.5404	0.0278	0.8751	0.068*
C31	0.3391 (3)	0.0887 (3)	0.93131 (11)	0.0431 (7)
C32	0.2134 (3)	0.2126 (3)	0.94971 (12)	0.0564 (8)
H32	0.1349	0.2003	0.9782	0.068*
C33	0.2016 (4)	0.3536 (4)	0.92696 (15)	0.0708 (9)
H33	0.1166	0.4358	0.9402	0.085*
C34	0.3518 (3)	−0.0615 (3)	0.95527 (11)	0.0417 (6)
C35	0.4571 (3)	−0.2971 (3)	0.97852 (14)	0.0644 (9)
H35	0.5294	−0.3899	0.9831	0.077*
C36	0.3034 (3)	−0.2594 (3)	0.99545 (13)	0.0617 (8)
H36	0.2506	−0.3234	1.0139	0.074*
O1	0.2835 (2)	0.3113 (3)	0.41706 (10)	0.0778 (7)
O2	0.5143 (3)	0.1699 (3)	0.41170 (11)	0.0944 (8)
O3	0.3276 (3)	0.0750 (3)	0.43228 (14)	0.1103 (10)
O4	0.1720 (3)	0.3963 (3)	1.08721 (12)	0.0926 (8)
O5	0.2200 (2)	0.1559 (2)	1.09430 (9)	0.0675 (6)
O6	−0.0137 (2)	0.2969 (3)	1.10375 (11)	0.0854 (8)
Ag1	0.0000	0.0000	1.0000	0.05936 (11)
Ag2	0.23738 (3)	0.30005 (3)	0.759780 (12)	0.08314 (12)
Ag3	0.5000	0.5000	0.5000	0.07317 (13)
N1	0.1033 (3)	0.1731 (3)	0.80549 (10)	0.0642 (7)
N2	0.0241 (3)	−0.0054 (3)	0.85106 (10)	0.0574 (7)
H2	0.0239	−0.0931	0.8641	0.069*
N3	0.4853 (2)	−0.1724 (2)	0.95343 (9)	0.0512 (6)
H3	0.5747	−0.1656	0.9387	0.061*
N4	0.2370 (2)	−0.1122 (3)	0.98131 (10)	0.0518 (6)
N5	0.3783 (3)	0.4142 (3)	0.70973 (11)	0.0650 (7)
N6	0.4661 (3)	0.5638 (3)	0.64922 (10)	0.0579 (7)
H6	0.4693	0.6415	0.6284	0.069*
N7	0.0144 (3)	0.6876 (3)	0.53138 (10)	0.0513 (6)
H7	−0.0771	0.6863	0.5458	0.062*
N8	0.2649 (2)	0.6190 (3)	0.50983 (10)	0.0574 (6)
N9	0.3743 (3)	0.1830 (3)	0.42040 (11)	0.0659 (7)
N10	0.1257 (3)	0.2861 (3)	1.09532 (10)	0.0595 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.058 (2)	0.064 (2)	0.069 (2)	−0.0259 (18)	0.0022 (16)	0.0091 (17)
C2	0.059 (2)	0.045 (2)	0.074 (2)	−0.0155 (16)	−0.0115 (15)	0.0133 (16)
C3	0.0399 (17)	0.0372 (18)	0.0618 (17)	−0.0096 (14)	−0.0072 (13)	−0.0040 (14)
C4	0.0543 (19)	0.040 (2)	0.0655 (18)	−0.0133 (16)	−0.0252 (15)	0.0029 (15)
C5	0.071 (2)	0.052 (2)	0.093 (2)	−0.004 (2)	−0.0319 (18)	−0.0003 (19)
C6	0.116 (4)	0.042 (3)	0.156 (4)	−0.002 (2)	−0.082 (3)	0.006 (3)
C7	0.134 (4)	0.079 (4)	0.135 (4)	−0.059 (3)	−0.091 (3)	0.049 (3)
C8	0.094 (3)	0.088 (3)	0.099 (3)	−0.050 (3)	−0.047 (2)	0.043 (2)
C9	0.058 (2)	0.057 (2)	0.085 (2)	−0.0246 (17)	−0.0236 (17)	0.0221 (17)
C10	0.071 (2)	0.058 (2)	0.097 (3)	−0.016 (2)	−0.011 (2)	0.019 (2)
C11	0.056 (2)	0.064 (3)	0.088 (2)	−0.021 (2)	0.0027 (17)	0.0080 (19)
C12	0.059 (2)	0.058 (2)	0.0521 (17)	−0.0357 (17)	−0.0021 (14)	0.0015 (15)
C13	0.056 (2)	0.059 (2)	0.0558 (18)	−0.0344 (17)	−0.0035 (14)	−0.0080 (15)
C14	0.064 (2)	0.081 (3)	0.065 (2)	−0.035 (2)	−0.0042 (16)	−0.0037 (17)
C15	0.060 (2)	0.107 (3)	0.083 (3)	−0.034 (2)	0.0069 (19)	−0.016 (2)
C16	0.055 (2)	0.086 (3)	0.123 (3)	−0.018 (2)	−0.010 (2)	−0.016 (3)
C17	0.069 (3)	0.072 (3)	0.094 (3)	−0.025 (2)	−0.020 (2)	0.008 (2)
C18	0.068 (2)	0.064 (2)	0.064 (2)	−0.0339 (19)	−0.0061 (16)	0.0019 (17)
C19	0.066 (2)	0.055 (2)	0.101 (3)	−0.0134 (19)	−0.0087 (19)	0.0177 (19)
C20	0.050 (2)	0.062 (2)	0.083 (2)	−0.0173 (18)	0.0016 (16)	0.0118 (18)
C21	0.057 (2)	0.059 (2)	0.0456 (16)	−0.0307 (17)	−0.0069 (13)	0.0079 (14)
C22	0.0530 (19)	0.058 (2)	0.0516 (17)	−0.0299 (17)	−0.0055 (14)	−0.0022 (15)
C23	0.066 (2)	0.095 (3)	0.0609 (19)	−0.044 (2)	−0.0032 (16)	0.0005 (18)
C24	0.065 (3)	0.125 (4)	0.078 (2)	−0.046 (3)	0.0149 (19)	−0.022 (2)
C25	0.056 (2)	0.107 (4)	0.110 (3)	−0.027 (2)	0.005 (2)	−0.035 (3)
C26	0.063 (3)	0.069 (3)	0.120 (3)	−0.022 (2)	−0.010 (2)	−0.009 (2)
C27	0.056 (2)	0.063 (2)	0.081 (2)	−0.0279 (18)	−0.0015 (17)	−0.0055 (19)
C28	0.076 (3)	0.047 (2)	0.109 (3)	−0.017 (2)	−0.031 (2)	0.032 (2)
C29	0.059 (2)	0.071 (3)	0.082 (2)	−0.030 (2)	−0.0148 (17)	0.0322 (19)
C30	0.0407 (17)	0.049 (2)	0.077 (2)	−0.0118 (14)	−0.0063 (14)	0.0159 (16)
C31	0.0390 (16)	0.0395 (18)	0.0511 (15)	−0.0099 (14)	−0.0129 (12)	0.0071 (13)
C32	0.0510 (19)	0.045 (2)	0.0669 (19)	−0.0067 (16)	−0.0083 (14)	0.0102 (15)
C33	0.065 (2)	0.041 (2)	0.100 (3)	−0.0046 (17)	−0.0170 (19)	0.0077 (18)
C34	0.0305 (15)	0.0371 (18)	0.0542 (16)	−0.0063 (13)	−0.0048 (12)	0.0033 (13)
C35	0.0461 (19)	0.0358 (19)	0.103 (2)	−0.0060 (14)	−0.0025 (16)	0.0210 (17)
C36	0.0428 (18)	0.046 (2)	0.091 (2)	−0.0145 (15)	0.0043 (15)	0.0176 (17)
O1	0.0471 (13)	0.0577 (16)	0.1129 (17)	−0.0039 (12)	0.0063 (12)	0.0224 (13)
O2	0.0428 (14)	0.0719 (18)	0.153 (2)	−0.0084 (12)	0.0064 (13)	0.0407 (15)
O3	0.0750 (18)	0.0600 (18)	0.187 (3)	−0.0273 (14)	0.0146 (17)	0.0236 (17)
O4	0.0644 (16)	0.0526 (16)	0.157 (2)	−0.0223 (13)	0.0026 (15)	0.0102 (15)
O5	0.0415 (12)	0.0481 (15)	0.0978 (15)	−0.0010 (11)	0.0055 (10)	0.0192 (12)
O6	0.0352 (13)	0.0696 (17)	0.137 (2)	−0.0074 (11)	0.0056 (12)	0.0374 (14)
Ag1	0.03255 (18)	0.0589 (2)	0.0786 (2)	−0.00828 (15)	0.00271 (14)	0.00923 (17)
Ag2	0.0825 (2)	0.0775 (2)	0.1007 (2)	−0.04617 (16)	−0.00935 (15)	0.03293 (16)
Ag3	0.0386 (2)	0.0909 (3)	0.0795 (2)	−0.00848 (19)	0.00153 (16)	−0.0079 (2)
N1	0.0682 (18)	0.059 (2)	0.0698 (16)	−0.0283 (15)	−0.0077 (13)	0.0195 (14)
N2	0.0552 (16)	0.0504 (18)	0.0674 (15)	−0.0230 (14)	0.0002 (12)	0.0116 (13)
N3	0.0310 (13)	0.0396 (15)	0.0779 (16)	−0.0079 (11)	−0.0003 (11)	0.0112 (12)
N4	0.0344 (13)	0.0409 (16)	0.0744 (15)	−0.0085 (11)	0.0008 (11)	0.0086 (12)
N5	0.0680 (19)	0.0603 (19)	0.0721 (17)	−0.0312 (15)	−0.0063 (13)	0.0172 (14)
N6	0.0583 (16)	0.0553 (18)	0.0618 (15)	−0.0250 (15)	0.0004 (12)	0.0073 (12)
N7	0.0363 (13)	0.0416 (15)	0.0731 (15)	−0.0106 (12)	−0.0039 (11)	0.0087 (12)
N8	0.0415 (14)	0.0541 (18)	0.0722 (16)	−0.0119 (12)	−0.0005 (12)	−0.0007 (13)
N9	0.0483 (17)	0.060 (2)	0.0818 (18)	−0.0153 (16)	0.0076 (13)	0.0171 (15)
N10	0.0461 (17)	0.053 (2)	0.0703 (16)	−0.0096 (15)	0.0040 (12)	0.0136 (13)

Geometric parameters (Å, º) top

C1—C2	1.344 (4)	C22—C27	1.392 (4)
C1—N8	1.374 (4)	C22—C23	1.393 (4)
C1—H1	0.93	C23—C24	1.367 (5)
C2—N7	1.362 (3)	C23—H23	0.93
C2—H2A	0.93	C24—C25	1.367 (5)
C3—N8	1.335 (3)	C24—H24	0.93
C3—N7	1.340 (3)	C25—C26	1.368 (5)
C3—C4	1.455 (4)	C25—H25	0.93
C4—C5	1.386 (4)	C26—C27	1.377 (4)
C4—C9	1.387 (4)	C26—H26	0.93
C5—C6	1.398 (5)	C27—H27	0.93
C5—H5	0.93	C28—C33	1.363 (4)
C6—C7	1.355 (6)	C28—C29	1.368 (4)
C6—H6A	0.93	C28—H28	0.93
C7—C8	1.353 (6)	C29—C30	1.393 (4)
C7—H7A	0.93	C29—H29	0.93
C8—C9	1.384 (4)	C30—C31	1.392 (3)
C8—H8	0.93	C30—H30	0.93
C9—H9	0.93	C31—C32	1.382 (4)
C10—C11	1.349 (4)	C31—C34	1.462 (4)
C10—N5	1.363 (4)	C32—C33	1.375 (4)
C10—H10	0.93	C32—H32	0.93
C11—N6	1.346 (4)	C33—H33	0.93
C11—H11	0.93	C34—N4	1.337 (3)
C12—N5	1.326 (4)	C34—N3	1.339 (3)
C12—N6	1.359 (3)	C35—C36	1.347 (4)
C12—C13	1.451 (4)	C35—N3	1.355 (3)
C13—C14	1.386 (4)	C35—H35	0.93
C13—C18	1.395 (4)	C36—N4	1.369 (4)
C14—C15	1.368 (5)	C36—H36	0.93
C14—H14	0.93	O1—N9	1.238 (3)
C15—C16	1.365 (5)	O2—N9	1.241 (3)
C15—H15	0.93	O3—N9	1.214 (3)
C16—C17	1.374 (5)	O4—N10	1.220 (3)
C16—H16	0.93	O5—N10	1.254 (3)
C17—C18	1.376 (4)	O6—N10	1.241 (3)
C17—H17	0.93	Ag1—N4ⁱ	2.095 (2)
C18—H18	0.93	Ag1—N4	2.095 (2)
C19—C20	1.359 (4)	Ag2—N1	2.104 (2)
C19—N1	1.362 (4)	Ag2—N5	2.106 (2)
C19—H19	0.93	Ag3—N8ⁱⁱ	2.090 (2)
C20—N2	1.346 (4)	Ag3—N8	2.090 (2)
C20—H20	0.93	N2—H2	0.86
C21—N1	1.328 (4)	N3—H3	0.86
C21—N2	1.356 (3)	N6—H6	0.86
C21—C22	1.455 (4)	N7—H7	0.86

C2—C1—N8	109.9 (3)	C23—C24—H24	120.0
C2—C1—H1	125.1	C24—C25—C26	120.0 (4)
N8—C1—H1	125.1	C24—C25—H25	120.0
C1—C2—N7	105.6 (3)	C26—C25—H25	120.0
C1—C2—H2A	127.2	C25—C26—C27	120.5 (4)
N7—C2—H2A	127.2	C25—C26—H26	119.8
N8—C3—N7	109.0 (2)	C27—C26—H26	119.8
N8—C3—C4	127.6 (3)	C26—C27—C22	120.6 (3)
N7—C3—C4	123.4 (2)	C26—C27—H27	119.7
C5—C4—C9	118.6 (3)	C22—C27—H27	119.7
C5—C4—C3	121.5 (3)	C33—C28—C29	120.7 (3)
C9—C4—C3	119.9 (3)	C33—C28—H28	119.6
C4—C5—C6	119.4 (4)	C29—C28—H28	119.6
C4—C5—H5	120.3	C28—C29—C30	120.0 (3)
C6—C5—H5	120.3	C28—C29—H29	120.0
C7—C6—C5	120.7 (4)	C30—C29—H29	120.0
C7—C6—H6A	119.7	C31—C30—C29	119.8 (3)
C5—C6—H6A	119.7	C31—C30—H30	120.1
C8—C7—C6	120.6 (4)	C29—C30—H30	120.1
C8—C7—H7A	119.7	C32—C31—C30	118.3 (3)
C6—C7—H7A	119.7	C32—C31—C34	121.7 (2)
C7—C8—C9	120.1 (4)	C30—C31—C34	120.0 (2)
C7—C8—H8	120.0	C33—C32—C31	121.6 (3)
C9—C8—H8	120.0	C33—C32—H32	119.2
C8—C9—C4	120.7 (3)	C31—C32—H32	119.2
C8—C9—H9	119.7	C28—C33—C32	119.5 (3)
C4—C9—H9	119.7	C28—C33—H33	120.2
C11—C10—N5	109.6 (3)	C32—C33—H33	120.2
C11—C10—H10	125.2	N4—C34—N3	109.0 (2)
N5—C10—H10	125.2	N4—C34—C31	127.2 (2)
N6—C11—C10	106.1 (3)	N3—C34—C31	123.8 (2)
N6—C11—H11	127.0	C36—C35—N3	106.1 (2)
C10—C11—H11	127.0	C36—C35—H35	126.9
N5—C12—N6	108.5 (3)	N3—C35—H35	126.9
N5—C12—C13	127.8 (3)	C35—C36—N4	109.4 (2)
N6—C12—C13	123.7 (3)	C35—C36—H36	125.3
C14—C13—C18	118.3 (3)	N4—C36—H36	125.3
C14—C13—C12	121.2 (3)	N4ⁱ—Ag1—N4	180
C18—C13—C12	120.5 (3)	N1—Ag2—N5	175.94 (11)
C15—C14—C13	120.5 (3)	N8ⁱⁱ—Ag3—N8	180
C15—C14—H14	119.8	C21—N1—C19	106.7 (2)
C13—C14—H14	119.8	C21—N1—Ag2	128.9 (2)
C16—C15—C14	121.0 (3)	C19—N1—Ag2	124.3 (2)
C16—C15—H15	119.5	C20—N2—C21	108.8 (3)
C14—C15—H15	119.5	C20—N2—H2	125.6
C15—C16—C17	119.6 (4)	C21—N2—H2	125.6
C15—C16—H16	120.2	C34—N3—C35	109.1 (2)
C17—C16—H16	120.2	C34—N3—H3	125.4
C16—C17—C18	120.2 (3)	C35—N3—H3	125.4
C16—C17—H17	119.9	C34—N4—C36	106.4 (2)
C18—C17—H17	119.9	C34—N4—Ag1	129.74 (18)
C17—C18—C13	120.4 (3)	C36—N4—Ag1	123.83 (18)
C17—C18—H18	119.8	C12—N5—C10	106.9 (2)
C13—C18—H18	119.8	C12—N5—Ag2	130.1 (2)
C20—C19—N1	109.5 (3)	C10—N5—Ag2	122.3 (2)
C20—C19—H19	125.3	C11—N6—C12	108.9 (3)
N1—C19—H19	125.3	C11—N6—H6	125.5
N2—C20—C19	106.0 (3)	C12—N6—H6	125.5
N2—C20—H20	127.0	C3—N7—C2	109.3 (2)
C19—C20—H20	127.0	C3—N7—H7	125.4
N1—C21—N2	109.0 (3)	C2—N7—H7	125.4
N1—C21—C22	127.8 (3)	C3—N8—C1	106.2 (2)
N2—C21—C22	123.2 (3)	C3—N8—Ag3	129.2 (2)
C27—C22—C23	117.4 (3)	C1—N8—Ag3	124.61 (19)
C27—C22—C21	120.9 (3)	O3—N9—O1	121.0 (3)
C23—C22—C21	121.6 (3)	O3—N9—O2	121.6 (3)
C24—C23—C22	121.5 (3)	O1—N9—O2	117.4 (3)
C24—C23—H23	119.2	O4—N10—O6	122.3 (3)
C22—C23—H23	119.2	O4—N10—O5	120.1 (3)
C25—C24—C23	120.0 (3)	O6—N10—O5	117.6 (3)
C25—C24—H24	120.0

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6ⁱ	0.86	2.03	2.893 (3)	178
N3—H3···O5ⁱⁱⁱ	0.86	1.95	2.812 (3)	178
N6—H6···O2ⁱⁱ	0.86	1.99	2.846 (3)	173
N7—H7···O1^iv	0.86	1.95	2.812 (3)	177

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

Experimental details

Crystal data
Chemical formula	[Ag(C₉H₈N₂)₂]NO₃
M_r	458.23
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.209 (5), 9.274 (5), 23.137 (5)
α, β, γ (°)	88.307 (5), 80.976 (5), 72.369 (5)
V (Å³)	1859.5 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.31 × 0.28 × 0.22

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis; Oxford Diffraction, 2006)
T_min, T_max	0.62, 0.86
No. of measured, independent and observed [I > 2σ(I)] reflections	14127, 8475, 4372
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.079, 0.80
No. of reflections	8475
No. of parameters	490
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.43

Computer programs: CrysAlis (Oxford Diffraction, 2006), 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
N2—H2···O6ⁱ	0.86	2.03	2.893 (3)	178
N3—H3···O5ⁱⁱ	0.86	1.95	2.812 (3)	178
N6—H6···O2ⁱⁱⁱ	0.86	1.99	2.846 (3)	173
N7—H7···O1^iv	0.86	1.95	2.812 (3)	177

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

Acknowledgements

The authors thank Yuncheng University and Jilin University for support.

References

Liu, Y.-Y., Ma, J.-F., Yang, J., Ma, J.-C. & Ping, G.-J. (2008). CrystEngComm, 10, 565–572. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2006). CrysAlis. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, J., Ma, J.-F., Batten, S. R. & Su, Z.-M. (2008). Chem. Commun. pp. 2233–2235. Web of Science CSD CrossRef Google Scholar