catena-Poly[ammonium [aqua-bis-(μ-2,3,5,6-tetra-oxo-4-nitro-pyridin-4-ido)argentate(I)]].

In the title compound, {(NH4)[Ag(C5HN2O6)2(H2O)]} n , the Ag(I) cation is seven-coordinated and is surrounded by four oxo O atoms of the 2,3,5,6-tetra-oxo-4-nitro-pyridin-4-ide species [Ag-O = 2.3848 (19), 2.4931 (18), 2.5361 (18) and 2.573 (2) Å], two nitro O atoms [Ag-O = 2.644 (2) and 2.661 (2) Å], and one water mol-ecule [Ag-O = 2.3133 (19) Å]. The pyridin-4-ide mono-anions act as polydentate bridging ligands and form a three-dimensional network that is stabilized through O-H⋯O and N-H⋯O hydrogen bonds involving the coordinating water mol-ecule and the imide function as donator groups. The ammonium cations are located in the cavities of the framework and are also involved in hydrogen bonding to O atoms of the ligand.

Related literature

For reviews of 1,2-dicarbonyl compounds, see: Aldoshin (2008 ▶); Ohba & Okawa (2000 ▶). The synthesis and crystal structures of ammonium and sodium 2,3,5,6-tetra­oxo-4-nitro­pyridinates have been reported previously (Palkina et al., 2000 ▶; Kuzmina et al., 2004 ▶). The structure of the organic anion in its hexa­aqua metal salts is described by Kovalchukova et al. (2003 ▶ and 2013 ▶). For references to related structures of metal complexes with cyclic polyoxo compounds, see: Coronado et al. (2007 ▶); Kitagawa & Kawata (2002 ▶).

Experimental

Crystal data

(NH4)[Ag(C5HN2O6)2(H2O)]

M = 514.08

Monoclinic,

a = 8.784 (2) Å

b = 18.551 (4) Å

c = 9.195 (2) Å

β = 90.70 (3)°

V = 1498.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.44 mm−1

T = 293 K

0.35 × 0.31 × 0.08 mm

Data collection

Enraf Nonius CAD-4 diffractometer

Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983 ▶) T min = 0.406, T max = 0.798

2952 measured reflections

2768 independent reflections

2094 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.066

S = 1.09

2768 reflections

283 parameters

11 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4-PC; data reduction: CAD-4-PC; 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: CIFTAB97 and SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813020631/pj2004sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020631/pj2004Isup2.hkl

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

(NH4)[Ag(C5HN2O6)2(H2O)]	F(000) = 1016
Mr = 514.08	Dx = 2.279 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.784 (2) Å	θ = 9.3–11.8°
b = 18.551 (4) Å	µ = 1.44 mm−1
c = 9.195 (2) Å	T = 293 K
β = 90.70 (3)°	Plate, dark yellow
V = 1498.2 (5) Å3	0.35 × 0.31 × 0.08 mm
Z = 4

Enraf Nonius CAD-4 diffractometer	2094 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
β-filter monochromator	θmax = 25.5°, θmin = 2.2°
ω/2θ scans	h = 0→10
Absorption correction: part of the refinement model (ΔF) Walker & Stuart (1983)	k = 0→22
Tmin = 0.406, Tmax = 0.798	l = −11→11
2952 measured reflections	3 standard reflections every 60 min
2768 independent reflections	intensity decay: none

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)] = 0.021	Hydrogen site location: difference Fourier map
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.0506P] where P = (Fo2 + 2Fc2)/3
2768 reflections	(Δ/σ)max = 0.001
283 parameters	Δρmax = 0.42 e Å−3
11 restraints	Δρmin = −0.58 e Å−3

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
Ag1	0.68914 (2)	0.518350 (10)	0.16959 (2)	0.03092 (9)
O1	0.6981 (2)	0.43383 (10)	−0.0151 (2)	0.0367 (4)
O2	0.49428 (18)	0.55092 (10)	0.3355 (2)	0.0337 (4)
O3	0.2721 (2)	0.64390 (10)	0.3252 (3)	0.0437 (5)
O5	−0.0852 (2)	0.46912 (11)	0.3204 (2)	0.0430 (5)
O6	0.1206 (2)	0.36677 (10)	0.3468 (2)	0.0380 (4)
O71	0.4081 (2)	0.33294 (10)	0.3308 (2)	0.0374 (4)
O72	0.5781 (2)	0.41601 (11)	0.3380 (3)	0.0434 (5)
O8	0.59699 (19)	0.87943 (10)	0.5161 (2)	0.0346 (4)
O9	0.40503 (19)	0.77524 (10)	0.4454 (2)	0.0371 (4)
O11	0.7861 (2)	0.62851 (10)	0.3053 (2)	0.0335 (4)
O12	0.99467 (19)	0.72206 (10)	0.3830 (2)	0.0361 (4)
O131	1.0495 (2)	0.83839 (10)	0.5427 (3)	0.0440 (5)
O132	0.8913 (2)	0.92310 (9)	0.4915 (2)	0.0337 (4)
N2	1.1853 (2)	0.79954 (14)	0.1619 (3)	0.0356 (5)
N4	0.0902 (2)	0.55773 (12)	0.3224 (2)	0.0277 (4)
H4	0.0200	0.5900	0.3174	0.033*
N7	0.4426 (2)	0.39746 (11)	0.3354 (2)	0.0255 (4)
N10	0.5921 (2)	0.70207 (10)	0.3659 (2)	0.0234 (4)
H10	0.5263	0.6718	0.3324	0.028*
N13	0.9224 (2)	0.85893 (11)	0.5015 (2)	0.0250 (4)
C1	0.3262 (2)	0.45034 (14)	0.3364 (2)	0.0232 (5)
C2	0.3668 (3)	0.52426 (12)	0.3337 (2)	0.0230 (4)
C3	0.2389 (3)	0.58051 (13)	0.3276 (3)	0.0267 (5)
C5	0.0468 (3)	0.48715 (13)	0.3246 (3)	0.0264 (5)
C6	0.1700 (3)	0.42790 (13)	0.3368 (2)	0.0243 (5)
C7	0.8114 (2)	0.80583 (12)	0.4653 (2)	0.0219 (4)
C8	0.6544 (2)	0.82305 (12)	0.4741 (2)	0.0212 (4)
C9	0.5389 (3)	0.76440 (13)	0.4277 (2)	0.0236 (5)
C11	0.7427 (3)	0.68490 (12)	0.3543 (2)	0.0222 (4)
C12	0.8630 (3)	0.74009 (12)	0.4048 (2)	0.0222 (4)
H11	0.768 (3)	0.4067 (17)	−0.019 (5)	0.074 (6)*
H12	0.624 (3)	0.4089 (17)	−0.015 (5)	0.074 (6)*
H21	1.109 (3)	0.8260 (14)	0.166 (4)	0.074 (6)*
H22	1.263 (3)	0.8246 (14)	0.176 (4)	0.074 (6)*
H23	1.182 (4)	0.7675 (14)	0.225 (3)	0.074 (6)*
H24	1.190 (4)	0.7813 (16)	0.080 (2)	0.074 (6)*

	U11	U22	U33	U12	U13	U23
Ag1	0.03248 (13)	0.03008 (13)	0.03023 (13)	−0.00021 (7)	0.00124 (8)	−0.00114 (8)
O1	0.0281 (9)	0.0371 (10)	0.0449 (11)	−0.0023 (8)	0.0016 (8)	−0.0077 (8)
O2	0.0202 (8)	0.0337 (9)	0.0471 (11)	−0.0027 (7)	0.0010 (7)	−0.0058 (8)
O3	0.0299 (9)	0.0264 (9)	0.0747 (15)	0.0000 (8)	−0.0052 (9)	−0.0102 (9)
O5	0.0197 (9)	0.0485 (11)	0.0607 (13)	−0.0068 (8)	−0.0051 (8)	0.0142 (10)
O6	0.0330 (9)	0.0325 (10)	0.0485 (11)	−0.0067 (7)	−0.0014 (8)	0.0053 (8)
O71	0.0462 (11)	0.0284 (9)	0.0374 (10)	0.0044 (8)	−0.0032 (8)	0.0019 (8)
O72	0.0233 (9)	0.0408 (10)	0.0662 (14)	0.0076 (8)	0.0017 (9)	0.0079 (10)
O8	0.0241 (8)	0.0340 (9)	0.0455 (11)	0.0061 (7)	−0.0065 (8)	−0.0150 (8)
O9	0.0189 (9)	0.0374 (10)	0.0551 (12)	−0.0008 (7)	0.0040 (8)	−0.0096 (9)
O11	0.0280 (9)	0.0327 (10)	0.0398 (10)	0.0029 (7)	−0.0013 (7)	−0.0140 (8)
O12	0.0204 (9)	0.0394 (10)	0.0484 (11)	0.0035 (7)	0.0034 (8)	−0.0105 (8)
O131	0.0251 (9)	0.0359 (10)	0.0707 (14)	−0.0020 (8)	−0.0166 (9)	−0.0045 (9)
O132	0.0338 (9)	0.0223 (9)	0.0451 (11)	−0.0026 (7)	0.0010 (8)	−0.0044 (7)
N2	0.0285 (11)	0.0406 (13)	0.0376 (13)	−0.0039 (9)	−0.0015 (9)	−0.0011 (10)
N4	0.0200 (9)	0.0316 (10)	0.0313 (11)	0.0040 (8)	−0.0017 (8)	0.0003 (9)
N7	0.0291 (10)	0.0305 (11)	0.0168 (9)	0.0042 (8)	−0.0014 (7)	0.0022 (8)
N10	0.0193 (9)	0.0257 (10)	0.0253 (10)	−0.0024 (7)	−0.0025 (7)	−0.0033 (8)
N13	0.0232 (9)	0.0284 (10)	0.0234 (10)	−0.0014 (8)	−0.0005 (7)	−0.0030 (8)
C1	0.0214 (11)	0.0304 (12)	0.0178 (11)	0.0023 (9)	−0.0015 (8)	−0.0002 (9)
C2	0.0195 (10)	0.0311 (12)	0.0183 (10)	−0.0002 (9)	0.0004 (8)	−0.0034 (9)
C3	0.0244 (11)	0.0291 (13)	0.0266 (12)	−0.0007 (10)	−0.0020 (9)	−0.0059 (9)
C5	0.0234 (11)	0.0356 (13)	0.0202 (11)	−0.0018 (10)	−0.0018 (8)	0.0029 (10)
C6	0.0245 (11)	0.0300 (12)	0.0184 (11)	−0.0022 (9)	−0.0013 (9)	0.0011 (9)
C7	0.0211 (11)	0.0239 (10)	0.0204 (11)	−0.0023 (9)	−0.0028 (8)	0.0001 (9)
C8	0.0197 (10)	0.0250 (11)	0.0187 (10)	0.0006 (8)	−0.0022 (8)	−0.0022 (9)
C9	0.0221 (11)	0.0269 (11)	0.0218 (11)	−0.0003 (9)	−0.0013 (9)	−0.0024 (9)
C11	0.0250 (11)	0.0257 (11)	0.0157 (10)	0.0020 (9)	−0.0015 (8)	−0.0002 (9)
C12	0.0202 (11)	0.0257 (11)	0.0207 (10)	0.0020 (9)	0.0001 (8)	0.0005 (9)

Ag1—O1	2.3133 (19)	O132—N13	1.225 (3)
Ag1—O2	2.3848 (19)	O132—Ag1iv	2.661 (2)
Ag1—O8i	2.4931 (18)	N2—H21	0.832 (19)
Ag1—O11	2.5361 (18)	N2—H22	0.83 (2)
Ag1—O5ii	2.573 (2)	N2—H23	0.830 (19)
Ag1—O72	2.644 (2)	N2—H24	0.827 (19)
Ag1—O132i	2.661 (2)	N4—C5	1.364 (3)
O1—H11	0.80 (3)	N4—C3	1.373 (3)
O1—H12	0.80 (3)	N4—H4	0.8600
O2—C2	1.224 (3)	N7—C1	1.417 (3)
O3—C3	1.212 (3)	N10—C11	1.366 (3)
O5—C5	1.206 (3)	N10—C9	1.373 (3)
O5—Ag1iii	2.573 (2)	N10—H10	0.8600
O6—C6	1.218 (3)	N13—C7	1.423 (3)
O71—N7	1.235 (3)	C1—C2	1.417 (3)
O72—N7	1.239 (3)	C1—C6	1.434 (3)
O8—C8	1.225 (3)	C2—C3	1.534 (3)
O8—Ag1iv	2.4931 (18)	C5—C6	1.546 (3)
O9—C9	1.206 (3)	C7—C12	1.417 (3)
O11—C11	1.203 (3)	C7—C8	1.419 (3)
O12—C12	1.223 (3)	C8—C9	1.544 (3)
O131—N13	1.235 (3)	C11—C12	1.539 (3)
O1—Ag1—O2	132.26 (6)	C5—N4—H4	117.9
O1—Ag1—O2	132.26 (6)	C3—N4—H4	117.9
O2—Ag1—O2	0.00 (5)	O71—N7—O72	120.3 (2)
O1—Ag1—O8i	96.52 (7)	O71—N7—C1	119.6 (2)
O2—Ag1—O8i	86.50 (7)	O72—N7—C1	120.0 (2)
O2—Ag1—O8i	86.50 (7)	C11—N10—C9	124.3 (2)
O1—Ag1—O11	153.27 (7)	C11—N10—H10	117.8
O2—Ag1—O11	73.76 (6)	C9—N10—H10	117.8
O2—Ag1—O11	73.76 (6)	O132—N13—O131	121.6 (2)
O8i—Ag1—O11	76.73 (7)	O132—N13—C7	120.24 (19)
O1—Ag1—O5ii	97.02 (7)	O131—N13—C7	118.21 (19)
O2—Ag1—O5ii	107.42 (7)	N7—C1—C2	119.23 (19)
O2—Ag1—O5ii	107.42 (7)	N7—C1—C6	119.3 (2)
O8i—Ag1—O5ii	144.87 (6)	C2—C1—C6	121.5 (2)
O11—Ag1—O5ii	76.64 (7)	O2—C2—O2	0.00 (16)
O1—Ag1—O72	87.67 (7)	O2—C2—C1	128.4 (2)
O2—Ag1—O72	62.25 (7)	O2—C2—C1	128.4 (2)
O2—Ag1—O72	62.25 (7)	O2—C2—C3	113.3 (2)
O8i—Ag1—O72	139.31 (6)	O2—C2—C3	113.3 (2)
O11—Ag1—O72	114.48 (7)	C1—C2—C3	118.3 (2)
O5ii—Ag1—O72	73.55 (6)	O3—C3—O3	0.0 (2)
O1—Ag1—O132i	78.24 (6)	O3—C3—N4	121.8 (2)
O2—Ag1—O132i	141.23 (6)	O3—C3—N4	121.8 (2)
O2—Ag1—O132i	141.23 (6)	O3—C3—C2	119.0 (2)
O8i—Ag1—O132i	63.63 (6)	O3—C3—C2	119.0 (2)
O11—Ag1—O132i	75.60 (6)	N4—C3—C2	119.2 (2)
O5ii—Ag1—O132i	87.76 (6)	O5—C5—N4	122.3 (2)
O72—Ag1—O132i	155.09 (5)	O5—C5—C6	118.5 (2)
Ag1—O1—H11	120 (3)	N4—C5—C6	119.2 (2)
Ag1—O1—H12	111 (3)	O6—C6—C1	127.8 (2)
H11—O1—H12	105.3 (9)	O6—C6—C5	114.7 (2)
O2—O2—C2	0 (10)	C1—C6—C5	117.6 (2)
O2—O2—Ag1	0 (6)	C12—C7—C8	122.1 (2)
C2—O2—Ag1	123.54 (16)	C12—C7—N13	117.8 (2)
O3—O3—C3	0 (10)	C8—C7—N13	119.65 (19)
C5—O5—Ag1iii	130.73 (17)	O8—C8—C7	127.9 (2)
N7—O72—Ag1	123.30 (16)	O8—C8—C9	114.66 (19)
C8—O8—Ag1iv	134.07 (15)	C7—C8—C9	117.45 (19)
C11—O11—Ag1	141.17 (16)	O9—C9—N10	122.3 (2)
N13—O132—Ag1iv	120.06 (15)	O9—C9—C8	118.9 (2)
H21—N2—H22	108.8 (9)	N10—C9—C8	118.83 (19)
H21—N2—H23	111 (3)	O11—C11—N10	122.9 (2)
H22—N2—H23	109.0 (9)	O11—C11—C12	118.2 (2)
H21—N2—H24	109.7 (9)	N10—C11—C12	118.9 (2)
H22—N2—H24	108 (3)	O12—C12—C7	127.4 (2)
H23—N2—H24	110.0 (9)	O12—C12—C11	114.6 (2)
C5—N4—C3	124.1 (2)	C7—C12—C11	118.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O11iii	0.86	2.18	2.979 (3)	155
N10—H10···O2	0.86	2.26	2.945 (3)	137
N10—H10···O3	0.86	2.29	3.030 (3)	144
O1—H11···O131v	0.80 (3)	2.06 (3)	2.851 (3)	177 (5)
O1—H12···O8vi	0.80 (3)	2.02 (3)	2.781 (2)	160 (3)
N2—H21···O6vii	0.83 (2)	2.16 (2)	2.962 (3)	163 (3)
N2—H22···O72viii	0.83 (2)	2.20 (2)	2.998 (3)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O11i	0.86	2.18	2.979 (3)	155
N10—H10⋯O2	0.86	2.26	2.945 (3)	137
N10—H10⋯O3	0.86	2.29	3.030 (3)	144
O1—H11⋯O131ii	0.80 (3)	2.06 (3)	2.851 (3)	177 (5)
O1—H12⋯O8iii	0.80 (3)	2.02 (3)	2.781 (2)	160 (3)
N2—H21⋯O6iv	0.83 (2)	2.16 (2)	2.962 (3)	163 (3)
N2—H22⋯O72v	0.83 (2)	2.20 (2)	2.998 (3)	160 (3)

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