(μ-5-Carb-oxy-1H-imidazole-4-carboxyl-ato-κN,O:N,O)bis-[amminesilver(I)].

In the title compound, [Ag(2)(C(5)H(2)N(2)O(4))(NH(3))(2)], each of the two Ag(I) atoms is coordinated by two N atoms from an ammonia mol-ecule and a 5-carb-oxy-1H-imidazole-4-carboxyl-ate ligand in an almost linear geometry, and by one carboxyl-ate O atom with a weak inter-action. The Ag atoms are assembled into a linear tetra-mer through Ag⋯Ag inter-actions. Each Ag tetra-mer is linked by four 5-carb-oxy-1H-imidazole-4-carboxyl-ate ligands, forming a puckered chain. The complex involves a strong intra-molecular O-H⋯O hydrogen bond.

Related literature

For general background to coordination polymers, see: Ferey (2008 ▶); Ma et al. (2009 ▶); Moulton & Zaworotko (2001 ▶); Tranchemontagne et al. (2009 ▶). For related structures with the 4,5-imidazole­dicarboxylic acid ligand, see: Caudle et al. (1997 ▶); Fang & Zhang (2006 ▶); Han et al. (2005 ▶); Zhong et al. (2006 ▶).

Experimental

Crystal data

[Ag2(C5H2N2O4)(NH3)2]

M = 403.89

Monoclinic,

a = 18.3800 (12) Å

b = 8.3243 (5) Å

c = 13.6696 (8) Å

β = 113.160 (1)°

V = 1922.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 4.07 mm−1

T = 190 K

0.35 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.330, T max = 0.686

5211 measured reflections

1911 independent reflections

1721 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.044

S = 1.05

1911 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045747/hy2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045747/hy2243Isup2.hkl

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

[Ag2(C5H2N2O4)(NH3)2]	F(000) = 1536
Mr = 403.89	Dx = 2.790 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1780 reflections
a = 18.3800 (12) Å	θ = 2.4–26.1°
b = 8.3243 (5) Å	µ = 4.07 mm−1
c = 13.6696 (8) Å	T = 190 K
β = 113.160 (1)°	Block, brown
V = 1922.9 (2) Å3	0.35 × 0.25 × 0.10 mm
Z = 8

Bruker SMART APEX CCD diffractometer	1911 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −22→18
Tmin = 0.330, Tmax = 0.686	k = −10→9
5211 measured reflections	l = −16→16

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.044	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.02P)2 + 2.4121P] where P = (Fo2 + 2Fc2)/3
1911 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

	x	y	z	Uiso*/Ueq
Ag2	0.206133 (14)	0.79951 (3)	0.660249 (17)	0.03620 (8)
O1	0.17397 (15)	0.5366 (3)	0.54751 (18)	0.0476 (6)
N2	0.15598 (14)	0.8616 (3)	0.49573 (18)	0.0306 (5)
Ag1	0.060181 (14)	1.13414 (3)	0.201582 (18)	0.03346 (8)
C1	0.11079 (17)	0.8155 (3)	0.3218 (2)	0.0269 (6)
C2	0.08372 (18)	0.7496 (4)	0.2126 (2)	0.0322 (7)
C3	0.13893 (16)	0.7428 (4)	0.4199 (2)	0.0275 (6)
C4	0.15067 (17)	0.5712 (4)	0.4527 (2)	0.0323 (7)
C5	0.13741 (19)	0.9977 (4)	0.4412 (2)	0.0332 (7)
N1	0.11022 (14)	0.9785 (3)	0.33560 (18)	0.0302 (5)
N3	0.25466 (19)	0.7478 (4)	0.8265 (2)	0.0366 (6)
N4	0.0094 (2)	1.3080 (4)	0.0800 (2)	0.0368 (6)
O2	0.13419 (14)	0.4656 (3)	0.37827 (19)	0.0436 (6)
O3	0.08142 (16)	0.5948 (3)	0.20328 (18)	0.0480 (6)
O4	0.06587 (15)	0.8395 (3)	0.13591 (16)	0.0441 (6)
H1	0.1399 (19)	1.094 (4)	0.467 (3)	0.040 (9)*
H2	0.112 (4)	0.523 (9)	0.291 (6)	0.17 (3)*
H3	0.275 (2)	0.836 (5)	0.869 (3)	0.062 (12)*
H4	0.300 (2)	0.686 (5)	0.843 (3)	0.058 (12)*
H5	0.218 (2)	0.696 (4)	0.844 (3)	0.042 (10)*
H6	0.041 (2)	1.385 (5)	0.078 (3)	0.060 (13)*
H7	−0.034 (3)	1.348 (5)	0.083 (3)	0.060 (13)*
H8	−0.004 (3)	1.271 (6)	0.024 (4)	0.073 (16)*

	U11	U22	U33	U12	U13	U23
Ag2	0.03743 (15)	0.04560 (16)	0.02245 (12)	0.00084 (10)	0.00842 (10)	0.00281 (10)
O1	0.0657 (16)	0.0373 (12)	0.0384 (13)	0.0061 (11)	0.0189 (12)	0.0123 (10)
N2	0.0315 (13)	0.0331 (13)	0.0236 (12)	0.0025 (10)	0.0072 (11)	−0.0013 (10)
Ag1	0.03572 (14)	0.03391 (14)	0.02914 (13)	0.00315 (10)	0.01104 (10)	0.00742 (9)
C1	0.0292 (15)	0.0262 (14)	0.0257 (14)	−0.0018 (11)	0.0112 (12)	−0.0028 (11)
C2	0.0312 (16)	0.0350 (16)	0.0281 (15)	−0.0025 (13)	0.0091 (13)	−0.0058 (13)
C3	0.0238 (14)	0.0324 (15)	0.0271 (14)	0.0005 (11)	0.0110 (12)	0.0006 (12)
C4	0.0318 (16)	0.0319 (16)	0.0357 (16)	0.0040 (12)	0.0159 (13)	0.0032 (13)
C5	0.0407 (18)	0.0283 (16)	0.0256 (14)	0.0030 (13)	0.0076 (13)	−0.0036 (12)
N1	0.0348 (14)	0.0288 (12)	0.0236 (11)	0.0020 (10)	0.0078 (11)	0.0023 (10)
N3	0.0409 (17)	0.0394 (16)	0.0255 (13)	−0.0030 (13)	0.0087 (13)	−0.0003 (12)
N4	0.0449 (18)	0.0308 (15)	0.0293 (15)	0.0008 (13)	0.0089 (14)	0.0015 (12)
O2	0.0585 (15)	0.0284 (11)	0.0447 (13)	0.0004 (10)	0.0212 (12)	−0.0026 (10)
O3	0.0710 (17)	0.0340 (12)	0.0370 (12)	−0.0047 (12)	0.0189 (12)	−0.0112 (10)
O4	0.0606 (15)	0.0428 (13)	0.0230 (11)	0.0044 (11)	0.0100 (11)	−0.0014 (10)

Ag1—N1	2.134 (2)	C2—O4	1.223 (4)
Ag1—N4	2.123 (3)	C2—O3	1.294 (4)
Ag1—O4	2.628 (2)	C3—C4	1.487 (4)
Ag2—N2	2.132 (2)	C4—O2	1.287 (4)
Ag2—N3	2.133 (3)	C5—N1	1.338 (4)
Ag2—O1	2.607 (2)	C5—H1	0.87 (4)
Ag1—Ag1i	2.9916 (5)	N3—H3	0.92 (4)
Ag1—Ag2ii	3.0021 (4)	N3—H4	0.93 (4)
O1—C4	1.228 (4)	N3—H5	0.90 (4)
N2—C5	1.325 (4)	N4—H6	0.87 (4)
N2—C3	1.377 (4)	N4—H7	0.87 (4)
C1—N1	1.371 (4)	N4—H8	0.77 (5)
C1—C3	1.373 (4)	O2—H2	1.19 (8)
C1—C2	1.481 (4)	O3—H2	1.26 (8)
N2—Ag2—N3	177.40 (11)	C1—C3—C4	132.2 (3)
N2—Ag2—O1	71.12 (8)	N2—C3—C4	120.0 (2)
N3—Ag2—O1	111.27 (10)	O1—C4—O2	123.4 (3)
N2—Ag2—Ag1iii	96.10 (7)	O1—C4—C3	119.5 (3)
N3—Ag2—Ag1iii	82.35 (9)	O2—C4—C3	117.1 (3)
O1—Ag2—Ag1iii	104.71 (6)	N2—C5—N1	114.1 (3)
C4—O1—Ag2	109.3 (2)	N2—C5—H1	127 (2)
C5—N2—C3	105.0 (2)	N1—C5—H1	119 (2)
C5—N2—Ag2	135.2 (2)	C5—N1—C1	104.3 (2)
C3—N2—Ag2	119.74 (19)	C5—N1—Ag1	134.8 (2)
N4—Ag1—N1	173.75 (11)	C1—N1—Ag1	120.49 (18)
N4—Ag1—O4	115.67 (10)	Ag2—N3—H3	114 (3)
N1—Ag1—O4	70.43 (8)	Ag2—N3—H4	109 (2)
N4—Ag1—Ag1i	99.91 (10)	H3—N3—H4	101 (3)
N1—Ag1—Ag1i	76.36 (7)	Ag2—N3—H5	109 (2)
O4—Ag1—Ag1i	106.67 (5)	H3—N3—H5	112 (3)
N4—Ag1—Ag2ii	82.99 (10)	H4—N3—H5	111 (3)
N1—Ag1—Ag2ii	99.09 (7)	Ag1—N4—H6	115 (3)
O4—Ag1—Ag2ii	87.07 (6)	Ag1—N4—H7	111 (3)
Ag1i—Ag1—Ag2ii	162.610 (12)	H6—N4—H7	111 (4)
N1—C1—C3	108.8 (2)	Ag1—N4—H8	112 (4)
N1—C1—C2	119.1 (2)	H6—N4—H8	103 (4)
C3—C1—C2	132.0 (3)	H7—N4—H8	104 (4)
O4—C2—O3	122.5 (3)	C4—O2—H2	113 (3)
O4—C2—C1	120.6 (3)	C2—O3—H2	113 (3)
O3—C2—C1	116.9 (3)	C2—O4—Ag1	108.15 (19)
C1—C3—N2	107.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	1.19 (8)	1.26 (8)	2.448 (3)	172 (6)

Table 1

Selected bond lengths (Å)

Ag1—N1	2.134 (2)
Ag1—N4	2.123 (3)
Ag1—O4	2.628 (2)
Ag2—N2	2.132 (2)
Ag2—N3	2.133 (3)
Ag2—O1	2.607 (2)
Ag1⋯Ag1i	2.9916 (5)
Ag1⋯Ag2ii	3.0021 (4)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	1.19 (8)	1.26 (8)	2.448 (3)	172 (6)