Bis{1-[(1H-benzimidazol-1-yl)methyl-κN3]-1H-1,2,3,4-tetra­zole}silver(I) nitrate

Yang, H.; Wang, X.; Ding, Y.; Meng, X.

doi:10.1107/S1600536810006653

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m340

doi:10.1107/S1600536810006653

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Bis{1-[(1H-benzimidazol-1-yl)methyl-κN³]-1H-1,2,3,4-tetrazole}silver(I) nitrate

Huai-xia Yang,^a Xia Wang,^a Ya-nan Ding ^b and Xiang-ru Meng ^b ^*

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: mxr@zzu.edu.cn

(Received 20 February 2010; accepted 21 February 2010; online 27 February 2010)

In the title salt, [Ag(C₉H₈N₆)₂]NO₃, the central Ag^I atom is linearly coordinated by the N atoms [171.97 (8)°] from two 1-[(benzimidazol-1-yl)methyl]-1H-1,2,3,4-tetrazole ligands. The benzimidazole rings in adjacent molecules are parallel with an average interplanar distance of 3.461 Å; adjacent molecules are linked through N—H⋯O hydrogen bonds into a linear chain along the b-axis direction.

Related literature

For similar compounds, see: Bronisz (2004 ); Meng et al. (2009 , 2004 ); Huang et al. (2006 ).

Experimental

Crystal data

[Ag(C₉H₈N₆)₂]NO₃
M_r = 570.31
Monoclinic, P 2₁ /n
a = 11.125 (2) Å
b = 9.3276 (19) Å
c = 20.189 (4) Å
β = 94.80 (3)°
V = 2087.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ) T_min = 0.807, T_max = 0.846
25286 measured reflections
4974 independent reflections
4605 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.03
4974 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8C⋯O3	0.86	2.32	3.105 (5)	153
N8—H8C⋯O2	0.86	2.40	3.176 (4)	151
N2—H2B⋯O1ⁱ	0.86	2.06	2.881 (4)	159
Symmetry code: (i) x+1, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2006); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006653/ng2735sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006653/ng2735Isup2.hkl

checkCIF report

Comment top

In coordination and metallosupramolecular chemistry, there are many symmetrical tetrazole and benzimidazole ligands, which have been widely used as the classical ligands (Bronisz 2004; Meng et al. 2004). However, studies on unsymmetrical ligands concerning tetrazole and benzimidazole are rather insufficient (Meng et al. 2009; Huang et al. 2006). We are engaged in the synthesis of unsymmetrical N-heterocyclic ligands and synthesized compound 1-((benzimidazole-1-yl)methyl)-1-H-1,2,3,4-tetrazole. In this work, we selected this compound as ligand and generate a new complex [Ag(C₉H₈N₆)₂](NO₃), (I), which is reported here. In complex (I) each Ag^I ion is two-coordinated by two N atom from two benzimidazole units and the nitrate anion does not coordinate to Ag^I ion (Fig. 1). Benzimidazole rings between the adjacent molecules are stacked in a face-to-face orientation with the distance of 3.461 Å. [Ag(C₉H₈N₆)₂](NO₃) units are linked through these π–π interactions and various kinds of hydrogen bonds such as N—H···O, C—H···O, and C—H···N hydrogen bonds resulting in a three-dimensional packing structure in solid state as shown in Fig. 2.

Related literature top

For similar compounds, see: Bronisz (2004); Meng et al. (2009, 2004); Huang et al. (2006)

For related literature, see: Meng et al. (2004).

Experimental top

The ligand 1-((benzimidazole-1-yl)methyl)-1H-1,2,3,4-tetrazole (0.1 mmol, 0.020 g) in methanol (6 ml) was added dropwise to a solution of AgNO₃ (0.05 mmol, 0.008 g) in H₂O (3 ml). The resulting solution was allowed to stand at room temperature in the dark. After four weeks good quality colorless crystals were obtained from the filtrate and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXL97 (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. View of the title complex, showing the labeling of the 30% probability ellipsolids.

Bis{1-[(1H-benzimidazol-1-yl)methyl-κN³]-1H-1,2,3,4-tetrazole}silver(I) nitrate top

Crystal data top

[Ag(C₉H₈N₆)₂]NO₃	F(000) = 1144
M_r = 570.31	D_x = 1.815 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.125 (2) Å	Cell parameters from 6007 reflections
b = 9.3276 (19) Å	θ = 2.0–27.9°
c = 20.189 (4) Å	µ = 1.02 mm⁻¹
β = 94.80 (3)°	T = 293 K
V = 2087.6 (7) Å³	Prism, colorless
Z = 4	0.22 × 0.18 × 0.17 mm

Data collection top

Rigaku Saturn diffractometer	4974 independent reflections
Radiation source: fine-focus sealed tube	4605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.9°, θ_min = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −12→12
T_min = 0.807, T_max = 0.846	l = −25→26
25286 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.056P)² + 1.4891P] where P = (F_o² + 2F_c²)/3
4974 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ag(C₉H₈N₆)₂]NO₃	V = 2087.6 (7) Å³
M_r = 570.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.125 (2) Å	µ = 1.02 mm⁻¹
b = 9.3276 (19) Å	T = 293 K
c = 20.189 (4) Å	0.22 × 0.18 × 0.17 mm
β = 94.80 (3)°

Data collection top

Rigaku Saturn diffractometer	4974 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	4605 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.846	R_int = 0.033
25286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.58 e Å⁻³
4974 reflections	Δρ_min = −0.46 e Å⁻³
316 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 > 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	0.43599 (2)	0.61837 (3)	0.079718 (11)	0.04196 (10)
N1	0.59520 (18)	0.7426 (2)	0.08358 (11)	0.0287 (4)
N2	0.7519 (2)	0.8683 (2)	0.12658 (12)	0.0321 (5)
H2B	0.8090	0.8972	0.1548	0.039*
N3	0.7700 (2)	0.6972 (2)	0.24677 (11)	0.0300 (5)
N4	0.7703 (2)	0.8136 (3)	0.28571 (13)	0.0447 (6)
N5	0.8649 (3)	0.8034 (3)	0.32741 (13)	0.0505 (7)
N6	0.9263 (2)	0.6814 (3)	0.31659 (13)	0.0452 (6)
N7	0.2869 (2)	0.4769 (2)	0.06530 (11)	0.0320 (5)
N8	0.1619 (2)	0.2970 (2)	0.07878 (11)	0.0330 (5)
H8C	0.1284	0.2262	0.0973	0.040*
N9	0.2313 (2)	0.3251 (2)	0.22291 (11)	0.0302 (5)
N10	0.1337 (2)	0.4074 (3)	0.22742 (12)	0.0360 (5)
N11	0.0800 (2)	0.3607 (3)	0.27719 (13)	0.0415 (6)
N12	0.1414 (3)	0.2475 (3)	0.30616 (13)	0.0452 (6)
N13	0.0308 (2)	0.0190 (3)	0.17241 (12)	0.0433 (6)
C1	0.6263 (2)	0.8422 (3)	0.03637 (13)	0.0294 (5)
C2	0.5768 (3)	0.8669 (3)	−0.02817 (14)	0.0350 (6)
H2A	0.5120	0.8133	−0.0467	0.042*
C3	0.6278 (3)	0.9742 (3)	−0.06341 (14)	0.0414 (7)
H3A	0.5972	0.9924	−0.1069	0.050*
C4	0.7241 (3)	1.0564 (4)	−0.03570 (16)	0.0449 (7)
H4A	0.7550	1.1291	−0.0609	0.054*
C5	0.7746 (3)	1.0324 (3)	0.02809 (16)	0.0428 (7)
H5A	0.8390	1.0867	0.0466	0.051*
C6	0.7239 (2)	0.9228 (3)	0.06337 (13)	0.0306 (5)
C7	0.6732 (2)	0.7616 (3)	0.13568 (13)	0.0286 (5)
C8	0.6710 (3)	0.6705 (3)	0.19633 (14)	0.0362 (6)
H8A	0.5954	0.6864	0.2158	0.043*
H8B	0.6734	0.5705	0.1832	0.043*
C9	0.8655 (3)	0.6184 (3)	0.26680 (15)	0.0373 (6)
H9A	0.8859	0.5315	0.2482	0.045*
C10	0.2093 (2)	0.4638 (3)	0.00770 (13)	0.0302 (5)
C11	0.2002 (3)	0.5461 (3)	−0.04975 (14)	0.0393 (6)
H11A	0.2533	0.6211	−0.0556	0.047*
C12	0.1095 (3)	0.5122 (4)	−0.09771 (15)	0.0445 (7)
H12A	0.0993	0.5677	−0.1360	0.053*
C13	0.0325 (3)	0.3965 (4)	−0.09021 (16)	0.0482 (8)
H13A	−0.0260	0.3748	−0.1243	0.058*
C14	0.0409 (3)	0.3135 (4)	−0.03344 (15)	0.0409 (7)
H14A	−0.0109	0.2367	−0.0284	0.049*
C15	0.1305 (2)	0.3501 (3)	0.01585 (14)	0.0309 (5)
C16	0.2541 (2)	0.3759 (3)	0.10575 (14)	0.0311 (6)
C17	0.3165 (3)	0.3487 (4)	0.17282 (14)	0.0386 (6)
H17A	0.3679	0.2651	0.1707	0.046*
H17B	0.3674	0.4301	0.1858	0.046*
C18	0.2339 (3)	0.2295 (3)	0.27144 (15)	0.0413 (7)
H18A	0.2930	0.1598	0.2796	0.050*
O1	−0.0183 (3)	−0.0797 (3)	0.19941 (14)	0.0774 (10)
O2	0.1406 (3)	0.0210 (4)	0.16912 (17)	0.0827 (9)
O3	−0.0271 (4)	0.1221 (4)	0.1498 (2)	0.1045 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03417 (14)	0.04656 (16)	0.04425 (16)	−0.01549 (9)	−0.00206 (10)	0.00349 (10)
N1	0.0227 (10)	0.0308 (11)	0.0324 (11)	−0.0037 (8)	0.0008 (8)	0.0011 (9)
N2	0.0289 (11)	0.0329 (11)	0.0336 (12)	−0.0057 (9)	−0.0038 (9)	0.0027 (9)
N3	0.0313 (11)	0.0287 (11)	0.0296 (11)	0.0018 (9)	−0.0009 (9)	0.0013 (9)
N4	0.0503 (16)	0.0381 (13)	0.0455 (15)	0.0081 (12)	0.0027 (12)	−0.0096 (11)
N5	0.0604 (18)	0.0486 (16)	0.0410 (15)	−0.0031 (13)	−0.0035 (13)	−0.0090 (12)
N6	0.0443 (15)	0.0448 (14)	0.0438 (15)	−0.0016 (12)	−0.0119 (11)	0.0039 (12)
N7	0.0299 (11)	0.0349 (12)	0.0313 (12)	−0.0058 (9)	0.0034 (9)	−0.0035 (9)
N8	0.0311 (11)	0.0342 (12)	0.0337 (12)	−0.0066 (9)	0.0027 (9)	0.0043 (9)
N9	0.0305 (11)	0.0312 (11)	0.0286 (11)	0.0035 (9)	0.0022 (9)	0.0027 (9)
N10	0.0312 (12)	0.0371 (12)	0.0397 (13)	0.0050 (9)	0.0022 (10)	0.0052 (10)
N11	0.0413 (14)	0.0438 (14)	0.0401 (14)	0.0019 (11)	0.0078 (11)	−0.0003 (11)
N12	0.0519 (16)	0.0451 (15)	0.0398 (14)	0.0022 (12)	0.0106 (12)	0.0096 (11)
N13	0.0479 (16)	0.0464 (15)	0.0344 (13)	−0.0141 (12)	−0.0037 (11)	0.0009 (11)
C1	0.0243 (12)	0.0310 (12)	0.0334 (14)	0.0011 (10)	0.0053 (10)	−0.0006 (10)
C2	0.0333 (14)	0.0418 (15)	0.0295 (14)	0.0011 (11)	−0.0003 (11)	−0.0023 (11)
C3	0.0475 (17)	0.0470 (17)	0.0297 (14)	0.0088 (14)	0.0039 (12)	0.0040 (12)
C4	0.0507 (19)	0.0415 (16)	0.0437 (17)	−0.0041 (14)	0.0108 (14)	0.0093 (14)
C5	0.0428 (17)	0.0389 (15)	0.0462 (17)	−0.0119 (13)	0.0007 (13)	0.0035 (13)
C6	0.0296 (13)	0.0317 (13)	0.0305 (13)	−0.0008 (10)	0.0023 (10)	0.0009 (11)
C7	0.0226 (11)	0.0294 (12)	0.0336 (13)	−0.0001 (9)	0.0010 (10)	0.0002 (10)
C8	0.0310 (14)	0.0381 (14)	0.0384 (15)	−0.0054 (11)	−0.0034 (11)	0.0081 (12)
C9	0.0366 (15)	0.0328 (14)	0.0413 (16)	0.0049 (11)	−0.0046 (12)	−0.0004 (11)
C10	0.0268 (12)	0.0335 (13)	0.0310 (13)	−0.0006 (10)	0.0058 (10)	−0.0049 (11)
C11	0.0459 (17)	0.0396 (15)	0.0342 (15)	0.0011 (13)	0.0129 (12)	0.0037 (12)
C12	0.0477 (18)	0.0555 (19)	0.0308 (15)	0.0114 (15)	0.0052 (13)	0.0029 (13)
C13	0.0405 (17)	0.069 (2)	0.0337 (16)	0.0098 (15)	−0.0039 (13)	−0.0109 (15)
C14	0.0309 (14)	0.0471 (17)	0.0442 (17)	−0.0037 (12)	0.0003 (12)	−0.0071 (14)
C15	0.0266 (13)	0.0347 (13)	0.0315 (14)	−0.0007 (10)	0.0044 (10)	−0.0033 (11)
C16	0.0266 (13)	0.0361 (14)	0.0310 (14)	−0.0037 (10)	0.0049 (10)	−0.0023 (11)
C17	0.0296 (14)	0.0495 (17)	0.0365 (15)	−0.0010 (12)	0.0016 (11)	0.0034 (13)
C18	0.0450 (17)	0.0364 (15)	0.0422 (17)	0.0068 (12)	0.0012 (13)	0.0095 (13)
O1	0.0706 (18)	0.092 (2)	0.0654 (17)	−0.0480 (17)	−0.0162 (14)	0.0345 (16)
O2	0.0586 (18)	0.090 (2)	0.103 (2)	−0.0185 (16)	0.0260 (17)	−0.0062 (19)
O3	0.112 (3)	0.073 (2)	0.120 (3)	0.0034 (19)	−0.046 (3)	0.024 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.112 (2)	C1—C6	1.393 (4)
Ag1—N7	2.121 (2)	C2—C3	1.377 (4)
N1—C7	1.318 (3)	C2—H2A	0.9300
N1—C1	1.395 (3)	C3—C4	1.396 (5)
N2—C7	1.348 (3)	C3—H3A	0.9300
N2—C6	1.385 (4)	C4—C5	1.379 (4)
N2—H2B	0.8600	C4—H4A	0.9300
N3—C9	1.327 (4)	C5—C6	1.392 (4)
N3—N4	1.340 (3)	C5—H5A	0.9300
N3—C8	1.457 (3)	C7—C8	1.492 (4)
N4—N5	1.295 (4)	C8—H8A	0.9700
N5—N6	1.354 (4)	C8—H8B	0.9700
N6—C9	1.304 (4)	C9—H9A	0.9300
N7—C16	1.318 (3)	C10—C11	1.387 (4)
N7—C10	1.394 (3)	C10—C15	1.395 (4)
N8—C16	1.340 (3)	C11—C12	1.375 (4)
N8—C15	1.381 (3)	C11—H11A	0.9300
N8—H8C	0.8600	C12—C13	1.394 (5)
N9—C18	1.323 (3)	C12—H12A	0.9300
N9—N10	1.339 (3)	C13—C14	1.380 (5)
N9—C17	1.459 (4)	C13—H13A	0.9300
N10—N11	1.287 (4)	C14—C15	1.391 (4)
N11—N12	1.363 (4)	C14—H14A	0.9300
N12—C18	1.304 (4)	C16—C17	1.491 (4)
N13—O1	1.222 (3)	C17—H17A	0.9700
N13—O3	1.224 (4)	C17—H17B	0.9700
N13—O2	1.229 (4)	C18—H18A	0.9300
C1—C2	1.391 (4)

N1—Ag1—N7	171.97 (8)	N2—C6—C1	105.7 (2)
C7—N1—C1	105.7 (2)	C5—C6—C1	122.1 (3)
C7—N1—Ag1	126.67 (18)	N1—C7—N2	112.5 (2)
C1—N1—Ag1	126.51 (17)	N1—C7—C8	121.5 (2)
C7—N2—C6	107.3 (2)	N2—C7—C8	126.0 (2)
C7—N2—H2B	126.3	N3—C8—C7	114.4 (2)
C6—N2—H2B	126.3	N3—C8—H8A	108.7
C9—N3—N4	107.9 (2)	C7—C8—H8A	108.7
C9—N3—C8	131.1 (2)	N3—C8—H8B	108.7
N4—N3—C8	120.9 (2)	C7—C8—H8B	108.7
N5—N4—N3	106.5 (2)	H8A—C8—H8B	107.6
N4—N5—N6	110.5 (2)	N6—C9—N3	109.6 (3)
C9—N6—N5	105.5 (2)	N6—C9—H9A	125.2
C16—N7—C10	105.7 (2)	N3—C9—H9A	125.2
C16—N7—Ag1	127.84 (19)	C11—C10—N7	130.2 (3)
C10—N7—Ag1	126.27 (18)	C11—C10—C15	121.1 (3)
C16—N8—C15	107.6 (2)	N7—C10—C15	108.6 (2)
C16—N8—H8C	126.2	C12—C11—C10	117.4 (3)
C15—N8—H8C	126.2	C12—C11—H11A	121.3
C18—N9—N10	107.7 (2)	C10—C11—H11A	121.3
C18—N9—C17	129.7 (2)	C11—C12—C13	121.5 (3)
N10—N9—C17	122.5 (2)	C11—C12—H12A	119.2
N11—N10—N9	106.9 (2)	C13—C12—H12A	119.2
N10—N11—N12	110.4 (2)	C14—C13—C12	121.7 (3)
C18—N12—N11	105.0 (2)	C14—C13—H13A	119.2
O1—N13—O3	121.2 (4)	C12—C13—H13A	119.2
O1—N13—O2	121.2 (3)	C13—C14—C15	116.8 (3)
O3—N13—O2	117.5 (3)	C13—C14—H14A	121.6
C2—C1—C6	120.8 (3)	C15—C14—H14A	121.6
C2—C1—N1	130.5 (2)	N8—C15—C14	133.0 (3)
C6—C1—N1	108.8 (2)	N8—C15—C10	105.5 (2)
C3—C2—C1	117.2 (3)	C14—C15—C10	121.5 (3)
C3—C2—H2A	121.4	N7—C16—N8	112.5 (2)
C1—C2—H2A	121.4	N7—C16—C17	123.6 (2)
C2—C3—C4	121.8 (3)	N8—C16—C17	123.9 (2)
C2—C3—H3A	119.1	N9—C17—C16	112.0 (2)
C4—C3—H3A	119.1	N9—C17—H17A	109.2
C5—C4—C3	121.6 (3)	C16—C17—H17A	109.2
C5—C4—H4A	119.2	N9—C17—H17B	109.2
C3—C4—H4A	119.2	C16—C17—H17B	109.2
C4—C5—C6	116.5 (3)	H17A—C17—H17B	107.9
C4—C5—H5A	121.7	N12—C18—N9	110.0 (3)
C6—C5—H5A	121.7	N12—C18—H18A	125.0
N2—C6—C5	132.2 (3)	N9—C18—H18A	125.0

N7—Ag1—N1—C7	−120.6 (6)	N4—N3—C8—C7	75.8 (3)
N7—Ag1—N1—C1	73.0 (7)	N1—C7—C8—N3	174.7 (2)
C9—N3—N4—N5	0.5 (3)	N2—C7—C8—N3	−4.5 (4)
C8—N3—N4—N5	176.4 (3)	N5—N6—C9—N3	0.2 (4)
N3—N4—N5—N6	−0.4 (4)	N4—N3—C9—N6	−0.4 (3)
N4—N5—N6—C9	0.1 (4)	C8—N3—C9—N6	−175.8 (3)
N1—Ag1—N7—C16	109.2 (6)	C16—N7—C10—C11	177.1 (3)
N1—Ag1—N7—C10	−64.6 (7)	Ag1—N7—C10—C11	−8.1 (4)
C18—N9—N10—N11	−0.3 (3)	C16—N7—C10—C15	−0.5 (3)
C17—N9—N10—N11	−178.4 (2)	Ag1—N7—C10—C15	174.33 (18)
N9—N10—N11—N12	0.1 (3)	N7—C10—C11—C12	−176.5 (3)
N10—N11—N12—C18	0.2 (4)	C15—C10—C11—C12	0.9 (4)
C7—N1—C1—C2	178.0 (3)	C10—C11—C12—C13	−2.4 (5)
Ag1—N1—C1—C2	−13.3 (4)	C11—C12—C13—C14	2.2 (5)
C7—N1—C1—C6	−1.4 (3)	C12—C13—C14—C15	−0.4 (5)
Ag1—N1—C1—C6	167.28 (18)	C16—N8—C15—C14	−178.1 (3)
C6—C1—C2—C3	−0.4 (4)	C16—N8—C15—C10	0.0 (3)
N1—C1—C2—C3	−179.8 (3)	C13—C14—C15—N8	176.8 (3)
C1—C2—C3—C4	−0.8 (4)	C13—C14—C15—C10	−1.1 (4)
C2—C3—C4—C5	1.2 (5)	C11—C10—C15—N8	−177.5 (2)
C3—C4—C5—C6	−0.4 (5)	N7—C10—C15—N8	0.3 (3)
C7—N2—C6—C5	180.0 (3)	C11—C10—C15—C14	0.9 (4)
C7—N2—C6—C1	−0.4 (3)	N7—C10—C15—C14	178.7 (3)
C4—C5—C6—N2	178.7 (3)	C10—N7—C16—N8	0.6 (3)
C4—C5—C6—C1	−0.8 (5)	Ag1—N7—C16—N8	−174.18 (18)
C2—C1—C6—N2	−178.4 (2)	C10—N7—C16—C17	178.0 (2)
N1—C1—C6—N2	1.1 (3)	Ag1—N7—C16—C17	3.3 (4)
C2—C1—C6—C5	1.3 (4)	C15—N8—C16—N7	−0.4 (3)
N1—C1—C6—C5	−179.3 (3)	C15—N8—C16—C17	−177.8 (3)
C1—N1—C7—N2	1.1 (3)	C18—N9—C17—C16	137.7 (3)
Ag1—N1—C7—N2	−167.49 (17)	N10—N9—C17—C16	−44.6 (4)
C1—N1—C7—C8	−178.2 (2)	N7—C16—C17—N9	136.4 (3)
Ag1—N1—C7—C8	13.2 (4)	N8—C16—C17—N9	−46.5 (4)
C6—N2—C7—N1	−0.5 (3)	N11—N12—C18—N9	−0.4 (4)
C6—N2—C7—C8	178.8 (3)	N10—N9—C18—N12	0.4 (3)
C9—N3—C8—C7	−109.3 (3)	C17—N9—C18—N12	178.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8C···O3	0.86	2.32	3.105 (5)	153
N8—H8C···O2	0.86	2.40	3.176 (4)	151
N2—H2B···O1ⁱ	0.86	2.06	2.881 (4)	159
C5—H5A···O3ⁱ	0.93	2.48	3.271 (5)	143
C8—H8A···N11ⁱⁱ	0.97	2.55	3.388 (4)	144
C8—H8B···N4ⁱⁱⁱ	0.97	2.54	3.406 (4)	148
C8—H8B···N5ⁱⁱⁱ	0.97	2.53	3.476 (4)	164
C17—H17A···N6ⁱⁱⁱ	0.97	2.41	3.250 (4)	145
C18—H18A···N10^iv	0.93	2.50	3.346 (4)	151

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

Experimental details

Crystal data
Chemical formula	[Ag(C₉H₈N₆)₂]NO₃
M_r	570.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.125 (2), 9.3276 (19), 20.189 (4)
β (°)	94.80 (3)
V (Å³)	2087.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.22 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2006)
T_min, T_max	0.807, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	25286, 4974, 4605
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.03
No. of reflections	4974
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.46

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8C···O3	0.86	2.32	3.105 (5)	153
N8—H8C···O2	0.86	2.40	3.176 (4)	151
N2—H2B···O1ⁱ	0.86	2.06	2.881 (4)	159

Symmetry code: (i) x+1, y+1, z.

Acknowledgements

The study was supported by the Science and Technology Department of Henan Province (082102330003). The authors also thank Professor Hou Hong-Wei of Zhengzhou University for his help.

References

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