Bis(2-amino­pyridine-κN1)silver(I) nitrate

Fun, H.-K.; John, J.; Jebas, S.R.; Balasubramanian, T.

doi:10.1107/S1600536808031292

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1359

doi:10.1107/S1600536808031292

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Bis(2-aminopyridine-κN¹)silver(I) nitrate

Hoong-Kun Fun,^a ^* Jain John,^b Samuel Robinson Jebas ^a ‡ and T. Balasubramanian ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 September 2008; accepted 26 September 2008; online 4 October 2008)

The asymmetric unit of the title compound, [Ag(C₅H₆N₂)₂]NO₃, consists of one and a half each of both cations and anions, the other halves being generated by crystallographic inversion centres. One of the Ag^I atoms lies on an inversion center and one of the nitrate ions is disordered across an inversion center. Each Ag^I atom is bicoordinated in a linear geometry by two N atoms from two 2-aminopyridine ligands. In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to (001) by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background, see: Kristiansson (2000 ); Windholz (1976 ). For related structures, see: Deng et al. (2004 ); Yang et al.(2004 ). For bond-length data, see: Allen et al.(1987 ); Jebas et al. (2007 ).

Experimental

Crystal data

[Ag(C₅H₆N₂)₂]NO₃
M_r = 358.12
Monoclinic, C 2/c
a = 43.3371 (10) Å
b = 5.8517 (1) Å
c = 15.1632 (3) Å
β = 100.502 (1)°
V = 3780.91 (13) Å³
Z = 12
Mo Kα radiation
μ = 1.61 mm⁻¹
T = 100.0 (1) K
0.71 × 0.31 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.394, T_max = 0.782
42747 measured reflections
9821 independent reflections
8093 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.075
S = 1.06
9821 reflections
293 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.91 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H1N6⋯O2ⁱ	0.83 (3)	2.22 (3)	3.016 (2)	160 (3)
N4—H1N4⋯O3ⁱⁱ	0.82 (3)	2.11 (3)	2.879 (2)	157 (3)
N6—H2N6⋯O3ⁱⁱⁱ	0.89 (3)	1.99 (3)	2.873 (2)	169 (2)
N4—H2N4⋯O1^iv	0.82 (3)	2.12 (3)	2.934 (3)	173 (3)
N2—H1N2⋯O4^v	0.83 (4)	2.32 (4)	3.102 (3)	159 (3)
N2—H1N2⋯O5^v	0.83 (4)	2.55 (4)	3.282 (4)	148 (3)
N2—H2N2⋯O5^vi	0.84 (1)	1.95 (1)	2.767 (4)	161 (3)
N2—H2N2⋯O4	0.85 (4)	2.49 (2)	3.210 (4)	144 (3)
C1—H1A⋯O3ⁱⁱ	0.93	2.41	3.183 (2)	140
C6—H6A⋯O5^vi	0.93	2.43	3.250 (4)	147
C13—H13A⋯O1^iv	0.93	2.52	3.406 (2)	159
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y+1, z; (vi) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031292/ci2682sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031292/ci2682Isup2.hkl

checkCIF report

Comment top

2-Aminopyridine is used in the manufacture of pharmaceuticals, especially antihistaminic drugs (Windholz, 1976). The silver(I) ion exhibits a large flexibility in its coordination with nitrogen-containing aromatic ligands, with coordination numbers ranging from two to eight (Kristiansson, 2000). As a part of our investigation on the binding modes of 2-aminopyridine with the metals, we report here the crystal structure of the title compound.

The asymmetric unit of the title compound consists of one and a half of both [Ag(C₅H₆N₂)₂]⁺ cation and nitrate anion. The other halves of the cation and anion are generated by crystallographic inversion centres. The Ag2 atom lies on an inversion center. Each Ag^I atom is bicoordinated in a linear geometry by two N atoms from two 2-aminopyridine ligands, with an N—Ag—N angle of 175.97 (6)° or 180°. Similar coordination is observed in bis(2-aminopyridine-κN¹)silver(I) hexafluoroarsenate (Yang et al., 2004) and bis(2-aminopyridine-κN¹)silver(I) perchlorate (Deng et al., 2004). The bond lengths in 2-aminopyridine ligands are found to have normal values (Jebas et al., 2007; Allen et al., 1987).

In the crystal structure, the cations and anions are linked by N—H···O and C—H···O hydrogen bonds (Table 1), generating a two-dimensional network parallel to the (001) [Fig.2].

Related literature top

For general background, see: Kristiansson (2000); Windholz (1976). For related structures, see: Deng et al. (2004); Yang et al.(2004). For bond-length data, see: Allen et al.(1987); Jebas et al. (2007).

Experimental top

2-Aminopyridine in water and silver nitrate in ammonia solution in a molar ratio of 1:1 were mixed with each other and refluxed at 343 K for 6 h. Yellow crystals were obtained after a month on slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Both components of the disordered nitrate ion are shown.
	Fig. 2. Part of the crystal packing of the title compound, viewed along the c axis. Dashed lines indicate hydrogen bonding.

Bis(2-aminopyridine-κN¹)silver(I) nitrate top

Crystal data top

[Ag(C₅H₆N₂)₂]NO₃	F(000) = 2136
M_r = 358.12	D_x = 1.887 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9946 reflections
a = 43.3371 (10) Å	θ = 2.7–38.4°
b = 5.8517 (1) Å	µ = 1.61 mm⁻¹
c = 15.1632 (3) Å	T = 100 K
β = 100.502 (1)°	Block, yellow
V = 3780.91 (13) Å³	0.71 × 0.31 × 0.16 mm
Z = 12

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9821 independent reflections
Radiation source: fine-focus sealed tube	8093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 37.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −74→74
T_min = 0.394, T_max = 0.783	k = −9→9
42747 measured reflections	l = −25→25

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0208P)² + 7.8111P] where P = (F_o² + 2F_c²)/3
9821 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.91 e Å⁻³
3 restraints	Δρ_min = −1.23 e Å⁻³

Crystal data top

[Ag(C₅H₆N₂)₂]NO₃	V = 3780.91 (13) Å³
M_r = 358.12	Z = 12
Monoclinic, C2/c	Mo Kα radiation
a = 43.3371 (10) Å	µ = 1.61 mm⁻¹
b = 5.8517 (1) Å	T = 100 K
c = 15.1632 (3) Å	0.71 × 0.31 × 0.16 mm
β = 100.502 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	9821 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	8093 reflections with I > 2σ(I)
T_min = 0.394, T_max = 0.783	R_int = 0.032
42747 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	3 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.91 e Å⁻³
9821 reflections	Δρ_min = −1.23 e Å⁻³
293 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
Ag1	0.167632 (4)	0.28414 (2)	0.419586 (9)	0.03102 (4)
Ag2	0.0000	0.5000	0.0000	0.02259 (4)
N1	0.15484 (3)	0.5267 (2)	0.51229 (9)	0.0210 (2)
N2	0.20046 (5)	0.7366 (4)	0.52126 (17)	0.0409 (5)
N3	0.17820 (3)	0.0248 (2)	0.32997 (10)	0.0224 (2)
N4	0.12990 (4)	−0.1493 (3)	0.32282 (14)	0.0315 (3)
N5	0.02529 (3)	0.2267 (2)	0.06994 (9)	0.0186 (2)
N6	0.04353 (4)	0.1195 (3)	−0.05863 (9)	0.0219 (2)
C1	0.12630 (4)	0.5008 (3)	0.53532 (12)	0.0266 (3)
H1A	0.1152	0.3676	0.5177	0.032*
C2	0.11291 (5)	0.6585 (4)	0.58280 (13)	0.0342 (4)
H2A	0.0933	0.6330	0.5978	0.041*
C3	0.12946 (5)	0.8586 (4)	0.60815 (14)	0.0378 (5)
H3A	0.1207	0.9715	0.6392	0.045*
C4	0.15844 (5)	0.8889 (3)	0.58741 (14)	0.0337 (4)
H4A	0.1697	1.0220	0.6045	0.040*
C5	0.17137 (4)	0.7160 (3)	0.53960 (12)	0.0245 (3)
C6	0.20720 (4)	0.0221 (3)	0.30857 (14)	0.0289 (3)
H6A	0.2203	0.1463	0.3256	0.035*
C7	0.21823 (5)	−0.1526 (4)	0.26346 (16)	0.0358 (4)
H7A	0.2382	−0.1466	0.2494	0.043*
C8	0.19870 (5)	−0.3410 (4)	0.23897 (14)	0.0309 (4)
H8A	0.2057	−0.4638	0.2089	0.037*
C9	0.16925 (4)	−0.3435 (3)	0.25950 (12)	0.0247 (3)
H9A	0.1561	−0.4683	0.2440	0.030*
C10	0.15902 (4)	−0.1544 (3)	0.30455 (11)	0.0213 (3)
C11	0.02265 (4)	0.1836 (3)	0.15608 (11)	0.0243 (3)
H11A	0.0125	0.2908	0.1859	0.029*
C12	0.03415 (4)	−0.0094 (3)	0.20150 (11)	0.0257 (3)
H12A	0.0321	−0.0321	0.2608	0.031*
C13	0.04910 (4)	−0.1712 (3)	0.15613 (12)	0.0241 (3)
H13A	0.0569	−0.3054	0.1848	0.029*
C14	0.05227 (4)	−0.1310 (3)	0.06904 (11)	0.0211 (3)
H14A	0.0621	−0.2379	0.0381	0.025*
C15	0.04047 (3)	0.0740 (3)	0.02689 (10)	0.0168 (2)
N7	0.42167 (4)	0.8502 (3)	0.16126 (10)	0.0247 (3)
O1	0.40629 (4)	0.9276 (3)	0.21680 (11)	0.0424 (4)
O2	0.44689 (4)	0.9364 (3)	0.15093 (11)	0.0398 (4)
O3	0.41119 (3)	0.6776 (2)	0.11617 (9)	0.0267 (2)
N8	0.25139 (8)	0.2036 (5)	0.5180 (2)	0.0269 (6)	0.50
O4	0.22809 (7)	0.2267 (5)	0.52820 (18)	0.0835 (9)
O5	0.26419 (7)	0.0502 (5)	0.5660 (2)	0.0338 (6)	0.50
H1N6	0.0430 (6)	0.253 (5)	−0.0764 (19)	0.034 (7)*
H1N4	0.1229 (7)	−0.034 (6)	0.343 (2)	0.045 (8)*
H2N6	0.0566 (6)	0.034 (4)	−0.0839 (17)	0.028 (6)*
H2N4	0.1184 (7)	−0.260 (5)	0.310 (2)	0.042 (8)*
H1N2	0.2107 (8)	0.854 (6)	0.536 (2)	0.061 (10)*
H2N2	0.2088 (7)	0.625 (4)	0.499 (2)	0.049 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.05014 (9)	0.01987 (6)	0.02380 (6)	0.00820 (6)	0.00876 (6)	−0.00160 (5)
Ag2	0.02482 (7)	0.02088 (8)	0.02184 (7)	0.00686 (6)	0.00365 (6)	−0.00096 (6)
N1	0.0244 (6)	0.0182 (6)	0.0196 (5)	0.0011 (5)	0.0020 (5)	−0.0018 (4)
N2	0.0327 (9)	0.0262 (8)	0.0647 (14)	−0.0056 (7)	0.0116 (9)	0.0090 (9)
N3	0.0251 (6)	0.0194 (6)	0.0220 (6)	0.0003 (5)	0.0024 (5)	−0.0025 (5)
N4	0.0265 (7)	0.0261 (7)	0.0442 (10)	−0.0002 (6)	0.0124 (7)	0.0056 (7)
N5	0.0197 (5)	0.0196 (6)	0.0166 (5)	0.0014 (5)	0.0037 (4)	−0.0017 (4)
N6	0.0282 (6)	0.0204 (6)	0.0183 (5)	0.0042 (5)	0.0081 (5)	0.0010 (5)
C1	0.0225 (7)	0.0304 (8)	0.0248 (7)	0.0002 (7)	−0.0009 (6)	−0.0001 (6)
C2	0.0263 (8)	0.0494 (12)	0.0262 (8)	0.0118 (8)	0.0030 (6)	0.0016 (8)
C3	0.0428 (11)	0.0406 (11)	0.0260 (8)	0.0212 (9)	−0.0039 (8)	−0.0110 (8)
C4	0.0417 (10)	0.0204 (8)	0.0329 (9)	0.0063 (7)	−0.0095 (8)	−0.0080 (7)
C5	0.0275 (7)	0.0171 (6)	0.0268 (7)	0.0005 (6)	−0.0005 (6)	0.0011 (6)
C6	0.0232 (7)	0.0269 (8)	0.0353 (9)	−0.0029 (6)	0.0019 (6)	−0.0072 (7)
C7	0.0227 (8)	0.0390 (11)	0.0457 (11)	0.0027 (8)	0.0058 (7)	−0.0105 (9)
C8	0.0331 (9)	0.0270 (8)	0.0310 (9)	0.0073 (7)	0.0016 (7)	−0.0077 (7)
C9	0.0299 (8)	0.0179 (6)	0.0236 (7)	0.0009 (6)	−0.0025 (6)	−0.0004 (6)
C10	0.0238 (7)	0.0186 (6)	0.0205 (6)	0.0012 (6)	0.0015 (5)	0.0028 (5)
C11	0.0243 (7)	0.0312 (8)	0.0178 (6)	0.0029 (6)	0.0052 (5)	−0.0023 (6)
C12	0.0255 (7)	0.0350 (9)	0.0161 (6)	−0.0027 (7)	0.0023 (5)	0.0034 (6)
C13	0.0223 (7)	0.0257 (8)	0.0227 (7)	−0.0014 (6)	−0.0002 (5)	0.0064 (6)
C14	0.0226 (6)	0.0185 (6)	0.0224 (7)	0.0012 (5)	0.0044 (5)	0.0015 (5)
C15	0.0170 (5)	0.0169 (6)	0.0164 (5)	−0.0009 (5)	0.0024 (4)	−0.0017 (5)
N7	0.0315 (7)	0.0195 (6)	0.0218 (6)	0.0061 (5)	0.0011 (5)	0.0018 (5)
O1	0.0510 (9)	0.0404 (8)	0.0358 (8)	0.0172 (8)	0.0082 (7)	−0.0138 (7)
O2	0.0404 (8)	0.0332 (8)	0.0431 (8)	−0.0102 (7)	0.0008 (6)	0.0149 (7)
O3	0.0302 (6)	0.0249 (6)	0.0254 (6)	0.0021 (5)	0.0061 (5)	−0.0067 (5)
N8	0.0210 (12)	0.0245 (17)	0.0309 (17)	0.0005 (12)	−0.0069 (12)	−0.0071 (11)
O4	0.106 (2)	0.0855 (18)	0.0630 (15)	−0.0602 (17)	0.0273 (14)	−0.0217 (13)
O5	0.0347 (14)	0.0324 (14)	0.0329 (14)	0.0093 (12)	0.0026 (11)	0.0020 (12)

Geometric parameters (Å, º) top

Ag1—N1	2.1406 (14)	C4—H4A	0.93
Ag1—N3	2.1413 (14)	C6—C7	1.364 (3)
Ag2—N5ⁱ	2.1115 (14)	C6—H6A	0.93
Ag2—N5	2.1115 (14)	C7—C8	1.398 (3)
N1—C5	1.343 (2)	C7—H7A	0.93
N1—C1	1.354 (2)	C8—C9	1.368 (3)
N2—C5	1.345 (3)	C8—H8A	0.93
N2—H1N2	0.83 (4)	C9—C10	1.414 (2)
N2—H2N2	0.85 (4)	C9—H9A	0.93
N3—C10	1.350 (2)	C11—C12	1.369 (3)
N3—C6	1.354 (2)	C11—H11A	0.93
N4—C10	1.341 (2)	C12—C13	1.397 (3)
N4—H1N4	0.82 (3)	C12—H12A	0.93
N4—H2N4	0.82 (3)	C13—C14	1.373 (2)
N5—C15	1.3473 (19)	C13—H13A	0.93
N5—C11	1.355 (2)	C14—C15	1.411 (2)
N6—C15	1.354 (2)	C14—H14A	0.93
N6—H1N6	0.83 (3)	N7—O2	1.239 (2)
N6—H2N6	0.89 (3)	N7—O1	1.250 (2)
C1—C2	1.363 (3)	N7—O3	1.257 (2)
C1—H1A	0.93	N8—N8ⁱⁱ	0.764 (6)
C2—C3	1.390 (4)	N8—O4	1.058 (4)
C2—H2A	0.93	N8—O5	1.223 (4)
C3—C4	1.361 (3)	N8—O4ⁱⁱ	1.294 (5)
C3—H3A	0.93	O4—N8ⁱⁱ	1.294 (5)
C4—C5	1.418 (3)

N1—Ag1—N3	175.97 (6)	N3—C6—C7	123.67 (17)
N5ⁱ—Ag2—N5	180.00 (10)	N3—C6—H6A	118.2
C5—N1—C1	118.27 (15)	C7—C6—H6A	118.2
C5—N1—Ag1	124.21 (12)	C6—C7—C8	118.27 (18)
C1—N1—Ag1	116.97 (12)	C6—C7—H7A	120.9
C5—N2—H1N2	120 (2)	C8—C7—H7A	120.9
C5—N2—H2N2	120 (2)	C9—C8—C7	119.52 (17)
H1N2—N2—H2N2	120 (3)	C9—C8—H8A	120.2
C10—N3—C6	118.18 (15)	C7—C8—H8A	120.2
C10—N3—Ag1	122.67 (11)	C8—C9—C10	119.31 (17)
C6—N3—Ag1	118.41 (12)	C8—C9—H9A	120.3
C10—N4—H1N4	121 (2)	C10—C9—H9A	120.3
C10—N4—H2N4	119 (2)	N4—C10—N3	118.52 (16)
H1N4—N4—H2N4	119 (3)	N4—C10—C9	120.47 (17)
C15—N5—C11	118.54 (14)	N3—C10—C9	121.01 (16)
C15—N5—Ag2	120.92 (10)	N5—C11—C12	123.47 (16)
C11—N5—Ag2	119.85 (11)	N5—C11—H11A	118.3
C15—N6—H1N6	119.7 (19)	C12—C11—H11A	118.3
C15—N6—H2N6	118.9 (16)	C11—C12—C13	118.07 (15)
H1N6—N6—H2N6	112 (2)	C11—C12—H12A	121.0
N1—C1—C2	123.88 (19)	C13—C12—H12A	121.0
N1—C1—H1A	118.1	C14—C13—C12	119.62 (16)
C2—C1—H1A	118.1	C14—C13—H13A	120.2
C1—C2—C3	117.93 (19)	C12—C13—H13A	120.2
C1—C2—H2A	121.0	C13—C14—C15	119.34 (15)
C3—C2—H2A	121.0	C13—C14—H14A	120.3
C4—C3—C2	119.80 (18)	C15—C14—H14A	120.3
C4—C3—H3A	120.1	N5—C15—N6	118.38 (14)
C2—C3—H3A	120.1	N5—C15—C14	120.90 (14)
C3—C4—C5	119.50 (19)	N6—C15—C14	120.71 (14)
C3—C4—H4A	120.2	O2—N7—O1	121.89 (18)
C5—C4—H4A	120.2	O2—N7—O3	119.84 (16)
N1—C5—N2	118.52 (18)	O1—N7—O3	118.26 (17)
N1—C5—C4	120.53 (17)	O4—N8—O5	110.4 (4)
N2—C5—C4	120.94 (19)

C5—N1—C1—C2	1.7 (3)	C6—N3—C10—C9	2.1 (2)
Ag1—N1—C1—C2	−170.08 (15)	Ag1—N3—C10—C9	−167.90 (12)
N1—C1—C2—C3	0.7 (3)	C8—C9—C10—N4	177.81 (18)
C1—C2—C3—C4	−1.7 (3)	C8—C9—C10—N3	−2.1 (3)
C2—C3—C4—C5	0.4 (3)	C15—N5—C11—C12	−1.1 (3)
C1—N1—C5—N2	176.31 (18)	Ag2—N5—C11—C12	169.43 (14)
Ag1—N1—C5—N2	−12.5 (2)	N5—C11—C12—C13	−0.7 (3)
C1—N1—C5—C4	−3.1 (3)	C11—C12—C13—C14	1.1 (3)
Ag1—N1—C5—C4	168.05 (13)	C12—C13—C14—C15	0.3 (2)
C3—C4—C5—N1	2.1 (3)	C11—N5—C15—N6	−178.89 (15)
C3—C4—C5—N2	−177.3 (2)	Ag2—N5—C15—N6	10.64 (19)
C10—N3—C6—C7	−0.6 (3)	C11—N5—C15—C14	2.6 (2)
Ag1—N3—C6—C7	169.84 (18)	Ag2—N5—C15—C14	−167.88 (11)
N3—C6—C7—C8	−0.9 (3)	C13—C14—C15—N5	−2.2 (2)
C6—C7—C8—C9	0.9 (3)	C13—C14—C15—N6	179.32 (15)
C7—C8—C9—C10	0.5 (3)	O5—N8—O4—N8ⁱⁱ	−177.8 (7)
C6—N3—C10—N4	−177.77 (17)	O4ⁱⁱ—N8—O4—N8ⁱⁱ	0.0
Ag1—N3—C10—N4	12.2 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H1N6···O2ⁱⁱⁱ	0.83 (3)	2.22 (3)	3.016 (2)	160 (3)
N4—H1N4···O3^iv	0.82 (3)	2.11 (3)	2.879 (2)	157 (3)
N6—H2N6···O3^v	0.89 (3)	1.99 (3)	2.873 (2)	169 (2)
N4—H2N4···O1^vi	0.82 (3)	2.12 (3)	2.934 (3)	173 (3)
N2—H1N2···O4^vii	0.83 (4)	2.32 (4)	3.102 (3)	159 (3)
N2—H1N2···O5^vii	0.83 (4)	2.55 (4)	3.282 (4)	148 (3)
N2—H2N2···O5ⁱⁱ	0.84 (1)	1.95 (1)	2.767 (4)	161 (3)
N2—H2N2···O4	0.85 (4)	2.49 (2)	3.210 (4)	144 (3)
C1—H1A···O3^iv	0.93	2.41	3.183 (2)	140
C6—H6A···O5ⁱⁱ	0.93	2.43	3.250 (4)	147
C13—H13A···O1^vi	0.93	2.52	3.406 (2)	159

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

Experimental details

Crystal data
Chemical formula	[Ag(C₅H₆N₂)₂]NO₃
M_r	358.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	43.3371 (10), 5.8517 (1), 15.1632 (3)
β (°)	100.502 (1)
V (Å³)	3780.91 (13)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.71 × 0.31 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.394, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	42747, 9821, 8093
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.857

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.075, 1.06
No. of reflections	9821
No. of parameters	293
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.91, −1.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H1N6···O2ⁱ	0.83 (3)	2.22 (3)	3.016 (2)	160 (3)
N4—H1N4···O3ⁱⁱ	0.82 (3)	2.11 (3)	2.879 (2)	157 (3)
N6—H2N6···O3ⁱⁱⁱ	0.89 (3)	1.99 (3)	2.873 (2)	169 (2)
N4—H2N4···O1^iv	0.82 (3)	2.12 (3)	2.934 (3)	173 (3)
N2—H1N2···O4^v	0.83 (4)	2.32 (4)	3.102 (3)	159 (3)
N2—H1N2···O5^v	0.83 (4)	2.55 (4)	3.282 (4)	148 (3)
N2—H2N2···O5^vi	0.84 (1)	1.95 (1)	2.767 (4)	161 (3)
N2—H2N2···O4	0.85 (4)	2.49 (2)	3.210 (4)	144 (3)
C1—H1A···O3ⁱⁱ	0.93	2.41	3.183 (2)	140
C6—H6A···O5^vi	0.93	2.43	3.250 (4)	147
C13—H13A···O1^iv	0.93	2.52	3.406 (2)	159

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

H-KF thanks the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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