Bis(2-amino-pyridine-κN)silver(I) nitrate.

The asymmetric unit of the title compound, [Ag(C(5)H(6)N(2))(2)]NO(3), 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-amino-pyridine 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 = 358.12

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.075

S = 1.06

9821 reflections

293 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.91 e Å−3

Δρmin = −1.23 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag(C5H6N2)2]NO3	F(000) = 2136
Mr = 358.12	Dx = 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

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

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(Fo2) + (0.0208P)2 + 7.8111P] where P = (Fo2 + 2Fc2)/3
9821 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.91 e Å−3
3 restraints	Δρmin = −1.23 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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)

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···O3iv	0.82 (3)	2.11 (3)	2.879 (2)	157 (3)
N6—H2N6···O3v	0.89 (3)	1.99 (3)	2.873 (2)	169 (2)
N4—H2N4···O1vi	0.82 (3)	2.12 (3)	2.934 (3)	173 (3)
N2—H1N2···O4vii	0.83 (4)	2.32 (4)	3.102 (3)	159 (3)
N2—H1N2···O5vii	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···O3iv	0.93	2.41	3.183 (2)	140
C6—H6A···O5ii	0.93	2.43	3.250 (4)	147
C13—H13A···O1vi	0.93	2.52	3.406 (2)	159

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⋯O1iv	0.82 (3)	2.12 (3)	2.934 (3)	173 (3)
N2—H1N2⋯O4v	0.83 (4)	2.32 (4)	3.102 (3)	159 (3)
N2—H1N2⋯O5v	0.83 (4)	2.55 (4)	3.282 (4)	148 (3)
N2—H2N2⋯O5vi	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⋯O5vi	0.93	2.43	3.250 (4)	147
C13—H13A⋯O1iv	0.93	2.52	3.406 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .