Poly[[[μ3-(E)-N-(pyridin-4-yl­methyl­idene)hy­droxy­laminato-κ3O:N:N′][μ2-(E)-N-(pyridin-4-yl­methyl­idene)hydroxyl­amine-κ2N:N′][(E)-N-(pyridin-4-yl­methyl­idene-κN)hydroxyl­amine]­disilver(I)] nitrate]

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812046090

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1540-m1541

doi:10.1107/S1600536812046090

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Poly[[[μ₃-(E)-N-(pyridin-4-ylmethylidene)hydroxylaminato-κ³O:N:N′][μ₂-(E)-N-(pyridin-4-ylmethylidene)hydroxylamine-κ²N:N′][(E)-N-(pyridin-4-ylmethylidene-κN)hydroxylamine]disilver(I)] nitrate]

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 November 2012; accepted 7 November 2012; online 28 November 2012)

The title coordination polymer, {[Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂]NO₃}_n, features a deprotonated N-(pyridin-4-ylmethylidene)hydroxylaminate anion and two neutral N-(pyridin-4-ylmethylidene)hydroxylamine molecules in the asymmetric unit. The anion connects three Ag^I atoms through its O and two N-donor atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The coordination geometry of the two independent metal atoms is T-shaped; the manner of bridging gives rise to a layer motif parallel to (100). In the crystal, the nitrate ion is disordered over two positions in a 1:1 ratio, and is sandwiched between adjacent layers. O—H⋯O hydrogen bonding is present between nitrate ions and layers, and also between adjacent layers.

Related literature

For mononuclear (Nitrato-κ²O,O′)bis[(E)-N-(pyridin-4-ylmethylidene-κN)hydroxyamine]silver(I), see: Gao & Ng (2012 ).

Experimental

Crystal data

[Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂]NO₃
M_r = 643.13
Monoclinic, P 2₁ /c
a = 13.1628 (18) Å
b = 10.9926 (18) Å
c = 16.315 (2) Å
β = 110.412 (4)°
V = 2212.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.82 mm⁻¹
T = 293 K
0.20 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.712, T_max = 0.811
21226 measured reflections
5047 independent reflections
3355 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.07
5047 reflections
306 parameters
26 restraints
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1	2.612 (3)
Ag1—N3	2.151 (3)
Ag1—N5	2.158 (3)
Ag2—O1ⁱ	2.546 (2)
Ag2—N1	2.161 (3)
Ag2—N2ⁱⁱ	2.183 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.84	1.81	2.642 (9)	169
O2—H2⋯O4′	0.84	2.21	2.997 (14)	156
O3—H3⋯O1ⁱⁱⁱ	0.84	1.69	2.527 (4)	174
Symmetry code: (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812046090/xu5648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046090/xu5648Isup2.hkl

checkCIF report

Comment top

The preceding report presents the crystal structure of bis(isonicotinylaldehyde oxide)(nitrato)silver (Gao & Ng, 2012). When some ammonium hydroxide was added to the reaction, the acid hydrogen of the isonicotinylaldehyde oxide is partially removed so that the product consists of a cation having two AgI atoms, one deprotonated ligand and two neutral ligands. The charge is balanced by a nitrate anion. The dinuclear cations are linked by coordination bonds into a polycation (Scheme I). The coordination polymer features a deprotonated N-(pyridin-4-ylmethylidene)hydroxylamine and two neutral N-(pyridin-4-ylmethylidene)hydroxylamine molecules. The anion connects three Ag^I atoms through its O and two N donor-atoms. One neutral ligand functions in a monodentate mode; the other functions in a bridging mode, binding though its two N atoms. The geometry of the two independent metal atoms is T-shaped (Fig. 1); the manner of bridge gives rise to a layer motif. The anion is sandwiched between adjacent layers (Fig. 2).

Related literature top

For mononuclear bis(isonicotinylaldehyde oxide)(nitrato)silver, see: Gao & Ng (2012).

Experimental top

Isonicotinaldehyde oxime was synthesized from the reaction of isonicotinaldehyde and hydroxylamine. Silver nitrate (1 mmol) dissolved in water (5 ml) was added to picolinaldehyde oxime (1 mmol) dissolved in ethanol (5 ml). Several drops of ammonium hydroxide were added. The solution was filtered and set aside, away from light, for the growth of colorless crystals.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of polymeric [Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂] NO₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the nitrate is not shown.
	Fig. 2. Layer motif.

Poly[[[µ₃-(E)-N-(pyridin-4-ylmethylidene)hydroxylaminato- κ³O:N:N'][µ₂-(E)-N-(pyridin-4- ylmethylidene)hydroxylamine-κ²N:N'][(E)-N- (pyridin-4-ylmethylidene-κN)hydroxylamine]disilver(I)] nitrate] top

Crystal data top

[Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂]NO₃	F(000) = 1264
M_r = 643.13	D_x = 1.931 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10662 reflections
a = 13.1628 (18) Å	θ = 3.1–27.5°
b = 10.9926 (18) Å	µ = 1.82 mm⁻¹
c = 16.315 (2) Å	T = 293 K
β = 110.412 (4)°	Prism, colorless
V = 2212.4 (6) Å³	0.20 × 0.12 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5047 independent reflections
Radiation source: fine-focus sealed tube	3355 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scan	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
T_min = 0.712, T_max = 0.811	k = −14→14
21226 measured reflections	l = −19→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0609P)²] where P = (F_o² + 2F_c²)/3
5047 reflections	(Δ/σ)_max = 0.001
306 parameters	Δρ_max = 0.77 e Å⁻³
26 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂]NO₃	V = 2212.4 (6) Å³
M_r = 643.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1628 (18) Å	µ = 1.82 mm⁻¹
b = 10.9926 (18) Å	T = 293 K
c = 16.315 (2) Å	0.20 × 0.12 × 0.12 mm
β = 110.412 (4)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5047 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3355 reflections with I > 2σ(I)
T_min = 0.712, T_max = 0.811	R_int = 0.047
21226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	26 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.07	Δρ_max = 0.77 e Å⁻³
5047 reflections	Δρ_min = −0.43 e Å⁻³
306 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.82406 (3)	0.44988 (5)	0.68283 (2)	0.0906 (2)
Ag2	0.45572 (3)	0.01686 (3)	0.114909 (19)	0.06273 (15)
O1	0.6234 (2)	0.4403 (3)	0.57575 (15)	0.0523 (6)
O2	1.0680 (3)	0.1718 (4)	0.3037 (2)	0.1041 (13)
H2	1.0946	0.1023	0.3041	0.156*
O3	0.6612 (3)	0.8349 (3)	1.07189 (16)	0.0633 (8)
H3	0.6532	0.9104	1.0744	0.095*
O4	1.1249 (5)	−0.0582 (8)	0.3006 (6)	0.1012 (16)	0.50
O5	1.2395 (7)	−0.1874 (9)	0.2869 (8)	0.1012 (16)	0.50
O6	1.2906 (5)	−0.0465 (7)	0.3833 (5)	0.1012 (16)	0.50
O4'	1.1788 (14)	−0.0670 (13)	0.3637 (8)	0.187 (4)	0.50
O5'	1.2614 (15)	−0.1635 (11)	0.2915 (11)	0.187 (4)	0.50
O6'	1.2181 (13)	0.0236 (10)	0.2655 (8)	0.187 (4)	0.50
N1	0.5108 (3)	0.0936 (3)	0.24501 (19)	0.0556 (8)
N2	0.6020 (2)	0.3906 (3)	0.49497 (17)	0.0460 (7)
N3	0.8829 (3)	0.3913 (4)	0.5817 (2)	0.0707 (11)
N4	1.0390 (3)	0.1859 (5)	0.3770 (2)	0.0763 (12)
N5	0.7900 (3)	0.5396 (4)	0.7881 (2)	0.0676 (10)
N6	0.6741 (3)	0.8056 (3)	0.99397 (19)	0.0522 (8)
N7	1.2216 (8)	−0.0974 (7)	0.3251 (6)	0.0797 (19)	0.50
N7'	1.2207 (7)	−0.0713 (10)	0.3065 (6)	0.0797 (19)	0.50
C1	0.5737 (3)	0.1916 (4)	0.2613 (2)	0.0578 (10)
H1	0.5978	0.2198	0.2175	0.069*
C2	0.6052 (3)	0.2537 (4)	0.3395 (2)	0.0553 (9)
H2A	0.6491	0.3223	0.3475	0.066*
C3	0.5710 (3)	0.2131 (4)	0.4062 (2)	0.0510 (9)
C4	0.5075 (4)	0.1096 (4)	0.3898 (2)	0.0589 (10)
H4	0.4840	0.0783	0.4331	0.071*
C5	0.4786 (4)	0.0526 (4)	0.3098 (3)	0.0627 (11)
H5	0.4354	−0.0166	0.3001	0.075*
C6	0.5966 (3)	0.2758 (4)	0.4903 (2)	0.0536 (9)
H6	0.6089	0.2305	0.5410	0.064*
C7	0.9441 (4)	0.2916 (5)	0.5886 (3)	0.0783 (14)
H7	0.9633	0.2467	0.6401	0.094*
C8	0.9799 (4)	0.2525 (5)	0.5230 (3)	0.0720 (13)
H8	1.0224	0.1830	0.5305	0.086*
C9	0.9516 (3)	0.3179 (4)	0.4458 (3)	0.0614 (11)
C10	0.8877 (3)	0.4200 (5)	0.4382 (3)	0.0651 (11)
H10	0.8670	0.4666	0.3874	0.078*
C11	0.8553 (4)	0.4518 (5)	0.5069 (3)	0.0701 (13)
H11	0.8114	0.5200	0.5005	0.084*
C12	0.9898 (4)	0.2858 (5)	0.3741 (3)	0.0706 (12)
H12	0.9781	0.3383	0.3270	0.085*
C13	0.7989 (4)	0.4791 (5)	0.8613 (3)	0.0721 (13)
H13	0.8249	0.3997	0.8674	0.087*
C14	0.7717 (4)	0.5284 (4)	0.9274 (3)	0.0623 (11)
H14	0.7795	0.4827	0.9772	0.075*
C15	0.7327 (3)	0.6453 (4)	0.9210 (2)	0.0528 (9)
C16	0.7235 (3)	0.7088 (4)	0.8454 (2)	0.0642 (11)
H16	0.6980	0.7885	0.8378	0.077*
C17	0.7525 (4)	0.6524 (5)	0.7817 (3)	0.0730 (13)
H17	0.7454	0.6960	0.7311	0.088*
C18	0.7078 (3)	0.6971 (4)	0.9947 (2)	0.0563 (10)
H18	0.7171	0.6489	1.0437	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0834 (3)	0.1332 (5)	0.0585 (2)	0.0248 (2)	0.0289 (2)	−0.0216 (2)
Ag2	0.0788 (3)	0.0733 (3)	0.03828 (19)	−0.01131 (17)	0.02310 (17)	−0.01213 (14)
O1	0.0644 (15)	0.0577 (17)	0.0356 (13)	−0.0003 (13)	0.0187 (12)	−0.0058 (12)
O2	0.111 (3)	0.147 (4)	0.067 (2)	0.034 (3)	0.046 (2)	−0.015 (2)
O3	0.0896 (19)	0.066 (2)	0.0418 (14)	0.0126 (17)	0.0320 (14)	0.0045 (13)
O4	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O5	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O6	0.079 (3)	0.101 (4)	0.109 (3)	0.025 (2)	0.014 (3)	−0.034 (3)
O4'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
O5'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
O6'	0.258 (10)	0.189 (9)	0.143 (6)	0.063 (7)	0.107 (7)	0.017 (6)
N1	0.069 (2)	0.062 (2)	0.0371 (16)	−0.0044 (18)	0.0200 (15)	−0.0061 (15)
N2	0.0533 (16)	0.054 (2)	0.0300 (14)	0.0030 (15)	0.0140 (13)	−0.0019 (13)
N3	0.064 (2)	0.093 (3)	0.054 (2)	0.009 (2)	0.0206 (18)	−0.014 (2)
N4	0.072 (2)	0.105 (4)	0.055 (2)	0.009 (2)	0.0257 (19)	−0.019 (2)
N5	0.071 (2)	0.086 (3)	0.047 (2)	0.012 (2)	0.0214 (18)	−0.0107 (19)
N6	0.0588 (18)	0.061 (2)	0.0401 (16)	−0.0009 (16)	0.0212 (15)	−0.0022 (15)
N7	0.098 (3)	0.102 (5)	0.050 (4)	0.016 (3)	0.039 (3)	0.003 (3)
N7'	0.098 (3)	0.102 (5)	0.050 (4)	0.016 (3)	0.039 (3)	0.003 (3)
C1	0.076 (3)	0.061 (3)	0.042 (2)	−0.006 (2)	0.027 (2)	−0.0037 (18)
C2	0.068 (2)	0.052 (2)	0.046 (2)	−0.006 (2)	0.0211 (19)	−0.0028 (18)
C3	0.065 (2)	0.049 (2)	0.0373 (17)	0.0062 (19)	0.0171 (17)	−0.0002 (16)
C4	0.082 (3)	0.058 (3)	0.042 (2)	−0.005 (2)	0.027 (2)	0.0007 (18)
C5	0.085 (3)	0.058 (3)	0.051 (2)	−0.014 (2)	0.030 (2)	−0.009 (2)
C6	0.072 (2)	0.053 (3)	0.0359 (18)	0.007 (2)	0.0188 (18)	0.0028 (17)
C7	0.083 (3)	0.098 (4)	0.053 (2)	0.020 (3)	0.023 (2)	−0.002 (3)
C8	0.068 (3)	0.088 (4)	0.059 (2)	0.015 (2)	0.022 (2)	−0.008 (3)
C9	0.048 (2)	0.081 (3)	0.055 (2)	−0.002 (2)	0.0171 (19)	−0.012 (2)
C10	0.057 (2)	0.083 (3)	0.057 (2)	0.007 (2)	0.022 (2)	−0.003 (2)
C11	0.057 (2)	0.078 (3)	0.072 (3)	0.010 (2)	0.018 (2)	−0.014 (3)
C12	0.068 (3)	0.088 (4)	0.057 (3)	0.008 (3)	0.023 (2)	−0.007 (2)
C13	0.077 (3)	0.068 (3)	0.072 (3)	0.011 (2)	0.027 (3)	−0.011 (2)
C14	0.080 (3)	0.060 (3)	0.052 (2)	0.003 (2)	0.028 (2)	0.004 (2)
C15	0.050 (2)	0.062 (3)	0.046 (2)	−0.0010 (18)	0.0171 (17)	−0.0025 (19)
C16	0.074 (3)	0.073 (3)	0.046 (2)	0.016 (2)	0.021 (2)	0.002 (2)
C17	0.085 (3)	0.092 (4)	0.043 (2)	0.015 (3)	0.023 (2)	0.002 (2)
C18	0.069 (2)	0.061 (3)	0.042 (2)	0.002 (2)	0.0229 (19)	0.0016 (18)

Geometric parameters (Å, º) top

Ag1—O1	2.612 (3)	C1—H1	0.9300
Ag1—N3	2.151 (3)	C2—C3	1.389 (5)
Ag1—N5	2.158 (3)	C2—H2A	0.9300
Ag2—O1ⁱ	2.546 (2)	C3—C4	1.382 (6)
Ag2—N1	2.161 (3)	C3—C6	1.466 (5)
Ag2—N2ⁱⁱ	2.183 (3)	C4—C5	1.377 (5)
O1—N2	1.362 (3)	C4—H4	0.9300
O1—Ag2ⁱⁱⁱ	2.546 (2)	C5—H5	0.9300
O2—N4	1.387 (4)	C6—H6	0.9300
O2—H2	0.8400	C7—C8	1.381 (6)
O3—N6	1.378 (4)	C7—H7	0.9300
O3—H3	0.8400	C8—C9	1.383 (6)
O4—N7	1.270 (9)	C8—H8	0.9300
O5—N7	1.234 (6)	C9—C10	1.381 (6)
O6—N7	1.199 (11)	C9—C12	1.469 (6)
O4'—N7'	1.239 (7)	C10—C11	1.377 (6)
O5'—N7'	1.211 (8)	C10—H10	0.9300
O6'—N7'	1.234 (8)	C11—H11	0.9300
N1—C1	1.327 (5)	C12—H12	0.9300
N1—C5	1.346 (5)	C13—C14	1.362 (6)
N2—C6	1.264 (5)	C13—H13	0.9300
N2—Ag2^iv	2.183 (3)	C14—C15	1.374 (6)
N3—C11	1.324 (6)	C14—H14	0.9300
N3—C7	1.342 (6)	C15—C16	1.386 (5)
N4—C12	1.267 (6)	C15—C18	1.467 (5)
N5—C17	1.325 (6)	C16—C17	1.374 (6)
N5—C13	1.337 (6)	C16—H16	0.9300
N6—C18	1.271 (5)	C17—H17	0.9300
C1—C2	1.378 (5)	C18—H18	0.9300

N3—Ag1—N5	167.71 (16)	N1—C5—C4	122.3 (4)
N3—Ag1—O1	91.45 (11)	N1—C5—H5	118.9
N5—Ag1—O1	96.21 (12)	C4—C5—H5	118.9
N1—Ag2—N2ⁱⁱ	162.98 (12)	N2—C6—C3	121.0 (3)
N1—Ag2—O1ⁱ	98.67 (10)	N2—C6—H6	119.5
N2ⁱⁱ—Ag2—O1ⁱ	89.75 (9)	C3—C6—H6	119.5
N2—O1—Ag2ⁱⁱⁱ	114.36 (19)	N3—C7—C8	123.1 (5)
N2—O1—Ag1	118.84 (18)	N3—C7—H7	118.5
Ag2ⁱⁱⁱ—O1—Ag1	125.99 (9)	C8—C7—H7	118.5
N4—O2—H2	109.5	C7—C8—C9	119.2 (5)
N6—O3—H3	109.5	C7—C8—H8	120.4
C1—N1—C5	117.4 (3)	C9—C8—H8	120.4
C1—N1—Ag2	119.0 (2)	C10—C9—C8	117.8 (4)
C5—N1—Ag2	123.4 (3)	C10—C9—C12	119.4 (4)
C6—N2—O1	116.5 (3)	C8—C9—C12	122.8 (4)
C6—N2—Ag2^iv	126.0 (3)	C11—C10—C9	119.0 (4)
O1—N2—Ag2^iv	115.8 (2)	C11—C10—H10	120.5
C11—N3—C7	116.9 (4)	C9—C10—H10	120.5
C11—N3—Ag1	120.0 (3)	N3—C11—C10	124.0 (4)
C7—N3—Ag1	123.1 (3)	N3—C11—H11	118.0
C12—N4—O2	110.8 (4)	C10—C11—H11	118.0
C17—N5—C13	116.7 (4)	N4—C12—C9	119.4 (5)
C17—N5—Ag1	122.7 (3)	N4—C12—H12	120.3
C13—N5—Ag1	120.4 (3)	C9—C12—H12	120.3
C18—N6—O3	111.4 (3)	N5—C13—C14	123.0 (5)
O6—N7—O5	123.3 (8)	N5—C13—H13	118.5
O6—N7—O4	119.3 (7)	C14—C13—H13	118.5
O5—N7—O4	117.4 (9)	C13—C14—C15	120.4 (4)
O5'—N7'—O6'	121.9 (8)	C13—C14—H14	119.8
O5'—N7'—O4'	122.0 (9)	C15—C14—H14	119.8
O6'—N7'—O4'	116.2 (8)	C14—C15—C16	117.0 (4)
N1—C1—C2	123.6 (3)	C14—C15—C18	119.0 (4)
N1—C1—H1	118.2	C16—C15—C18	124.0 (4)
C2—C1—H1	118.2	C17—C16—C15	119.0 (4)
C1—C2—C3	119.4 (4)	C17—C16—H16	120.5
C1—C2—H2A	120.3	C15—C16—H16	120.5
C3—C2—H2A	120.3	N5—C17—C16	123.9 (4)
C4—C3—C2	117.0 (3)	N5—C17—H17	118.1
C4—C3—C6	119.6 (3)	C16—C17—H17	118.1
C2—C3—C6	123.4 (4)	N6—C18—C15	122.2 (4)
C5—C4—C3	120.4 (3)	N6—C18—H18	118.9
C5—C4—H4	119.8	C15—C18—H18	118.9
C3—C4—H4	119.8

N3—Ag1—O1—N2	8.3 (3)	O1—N2—C6—C3	178.3 (3)
N5—Ag1—O1—N2	178.7 (2)	Ag2^iv—N2—C6—C3	13.6 (5)
N3—Ag1—O1—Ag2ⁱⁱⁱ	177.47 (17)	C4—C3—C6—N2	−143.2 (4)
N5—Ag1—O1—Ag2ⁱⁱⁱ	−12.15 (17)	C2—C3—C6—N2	35.2 (6)
N2ⁱⁱ—Ag2—N1—C1	153.9 (4)	C11—N3—C7—C8	1.2 (8)
O1ⁱ—Ag2—N1—C1	35.0 (3)	Ag1—N3—C7—C8	178.5 (4)
N2ⁱⁱ—Ag2—N1—C5	−31.0 (6)	N3—C7—C8—C9	−0.3 (8)
O1ⁱ—Ag2—N1—C5	−149.9 (3)	C7—C8—C9—C10	−0.3 (7)
Ag2ⁱⁱⁱ—O1—N2—C6	−88.6 (3)	C7—C8—C9—C12	177.4 (5)
Ag1—O1—N2—C6	81.8 (3)	C8—C9—C10—C11	0.0 (7)
Ag2ⁱⁱⁱ—O1—N2—Ag2^iv	77.7 (2)	C12—C9—C10—C11	−177.8 (4)
Ag1—O1—N2—Ag2^iv	−111.96 (18)	C7—N3—C11—C10	−1.6 (7)
N5—Ag1—N3—C11	−73.7 (8)	Ag1—N3—C11—C10	−179.0 (4)
O1—Ag1—N3—C11	55.0 (4)	C9—C10—C11—N3	1.1 (7)
N5—Ag1—N3—C7	109.0 (8)	O2—N4—C12—C9	179.7 (4)
O1—Ag1—N3—C7	−122.3 (4)	C10—C9—C12—N4	−172.9 (4)
N3—Ag1—N5—C17	61.9 (9)	C8—C9—C12—N4	9.5 (7)
O1—Ag1—N5—C17	−66.4 (4)	C17—N5—C13—C14	−0.1 (7)
N3—Ag1—N5—C13	−122.9 (7)	Ag1—N5—C13—C14	−175.6 (4)
O1—Ag1—N5—C13	108.8 (4)	N5—C13—C14—C15	0.2 (8)
C5—N1—C1—C2	−1.4 (6)	C13—C14—C15—C16	−0.4 (7)
Ag2—N1—C1—C2	174.0 (3)	C13—C14—C15—C18	−177.8 (4)
N1—C1—C2—C3	0.4 (7)	C14—C15—C16—C17	0.5 (6)
C1—C2—C3—C4	1.0 (6)	C18—C15—C16—C17	177.8 (4)
C1—C2—C3—C6	−177.4 (4)	C13—N5—C17—C16	0.2 (7)
C2—C3—C4—C5	−1.4 (6)	Ag1—N5—C17—C16	175.6 (4)
C6—C3—C4—C5	177.1 (4)	C15—C16—C17—N5	−0.4 (8)
C1—N1—C5—C4	0.9 (7)	O3—N6—C18—C15	−177.3 (3)
Ag2—N1—C5—C4	−174.2 (3)	C14—C15—C18—N6	178.2 (4)
C3—C4—C5—N1	0.4 (7)	C16—C15—C18—N6	1.0 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.84	1.81	2.642 (9)	169
O2—H2···O4′	0.84	2.21	2.997 (14)	156
O3—H3···O1^v	0.84	1.69	2.527 (4)	174

Symmetry code: (v) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₆H₅N₂O)(C₆H₆N₂O)₂]NO₃
M_r	643.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.1628 (18), 10.9926 (18), 16.315 (2)
β (°)	110.412 (4)
V (Å³)	2212.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.82
Crystal size (mm)	0.20 × 0.12 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.712, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	21226, 5047, 3355
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.07
No. of reflections	5047
No. of parameters	306
No. of restraints	26
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.43

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—O1	2.612 (3)	Ag2—O1ⁱ	2.546 (2)
Ag1—N3	2.151 (3)	Ag2—N1	2.161 (3)
Ag1—N5	2.158 (3)	Ag2—N2ⁱⁱ	2.183 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.84	1.81	2.642 (9)	168.7
O2—H2···O4'	0.84	2.21	2.997 (14)	156.1
O3—H3···O1ⁱⁱⁱ	0.84	1.69	2.527 (4)	174.1

Symmetry code: (iii) x, −y+3/2, z+1/2.

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Gao, S. & Ng, S. W. (2012). Acta Cryst. E68, m1542. CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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