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Acta Cryst. (2009). E65, m1523    [ doi:10.1107/S1600536809045747 ]

([mu]-5-Carboxy-1H-imidazole-4-carboxylato-[kappa]4N1,O5:N3,O4)bis[amminesilver(I)]

R.-S. Zhou and J.-F. Song

Abstract top

In the title compound, [Ag2(C5H2N2O4)(NH3)2], each of the two AgI atoms is coordinated by two N atoms from an ammonia molecule and a 5-carboxy-1H-imidazole-4-carboxylate ligand in an almost linear geometry, and by one carboxylate O atom with a weak interaction. The Ag atoms are assembled into a linear tetramer through Ag...Ag interactions. Each Ag tetramer is linked by four 5-carboxy-1H-imidazole-4-carboxylate ligands, forming a puckered chain. The complex involves a strong intramolecular O-H...O hydrogen bond.

Comment top

Coordination polymers are rapidly increasing because of their intriguing structures and wide potential applications as functional materials (Ferey, 2008; Ma et al., 2009; Moulton & Zaworotko, 2001; Tranchemontagne et al., 2009). Complexes with 4,5-imidazoledicarboxylic acid ligand have been recently reported (Caudle et al., 1997; Fang & Zhang, 2006; Zhong et al., 2006). The title compound is a new AgI complex built with 4,5-imidazoledicarboxylic acid ligand.

The asymmetric unit consists of two crystallographically independent AgI atoms, one partly deprotonated 4,5-imidazoledicarboxylate ligand and two ammonia molecules (Fig. 1). Each AgI atom is bonded to an ammonia molecule and one N atom and one O atom from the 4,5-imidazoledicarboxylate ligand in a chelating coordination mode. The Ag—N distances range from 2.123 (3) to 2.134 (2) Å (Table 1), and the N—Ag—N bond angles range from 173.75 (11) to 177.4 (11)°. It is worth to note that the bond distances of Ag—O [2.628 (2) and 2.607 (2) Å] are much longer than that observed in the reported silver carboxylate complexes (Han et al., 2005), indicating weak interaction between the AgI atom and the carboxylate O atom. Ag1 and Ag2 are assembled into an Ag2···Ag1···Ag1···Ag2 linear tetramer through the Ag···Ag interactions (Fig. 2) [Ag1···Ag1i = 2.9916 (5) and Ag1···Ag2ii = 3.0021 (4) Å; symmetry codes: (i) -x, y, 1/2 - z; (ii) x, 2 - y, -1/2 + z]. Moreover, there exists a strong hydrogen bond (O2—H2···O3) in the complex molecule (Table 2).

Related literature top

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 top

A solution of 4,5-imidazoledicarboxylic acid (6.5 mg, 0.05 mmol) in 2 ml water containing triethylamine (14 µl, 1 mmol) was directly mixed with a solution of AgNO3 in 2 ml of 25% aqueous ammonia. The resulting yellow solution was allowed to slowly crystalize at room temperature in dark. After one week, brown single crystals were collected by filtration, washed with small amounts of water and dried in air.

Refinement top

H atoms were located in a difference Fourier map and refined isotropically.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The one-dimensional puckered chain assembled by Ag tetramers and 4,5-imidazoledicarboxylate ligands. Dashed lines denote Ag···Ag interactions.
(µ-5-Carboxy-1H-imidazole-4-carboxylato- κ4N1,O5:N3,O4)bis[amminesilver(I)] top
Crystal data top
[Ag2(C5H2N2O4)(NH3)2]F(000) = 1536
Mr = 403.89Dx = 2.790 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1780 reflections
a = 18.3800 (12) Åθ = 2.4–26.1°
b = 8.3243 (5) ŵ = 4.07 mm−1
c = 13.6696 (8) ÅT = 190 K
β = 113.160 (1)°Block, brown
V = 1922.9 (2) Å30.35 × 0.25 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer		1911 independent reflections
Radiation source: fine-focus sealed tube1721 reflections with I > 2σ(I)
graphiteRint = 0.019
φ and ω scansθmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −22→18
Tmin = 0.330, Tmax = 0.686k = −10→9
5211 measured reflectionsl = −16→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.018Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.044H 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 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.50 e Å−3
Crystal data top
[Ag2(C5H2N2O4)(NH3)2]V = 1922.9 (2) Å3
Mr = 403.89Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.3800 (12) ŵ = 4.07 mm−1
b = 8.3243 (5) ÅT = 190 K
c = 13.6696 (8) Å0.35 × 0.25 × 0.10 mm
β = 113.160 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		1911 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1721 reflections with I > 2σ(I)
Tmin = 0.330, Tmax = 0.686Rint = 0.019
5211 measured reflectionsθmax = 26.1°
Refinement top
R[F2 > 2σ(F2)] = 0.018H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.044Δρmax = 0.45 e Å−3
S = 1.05Δρmin = −0.50 e Å−3
1911 reflectionsAbsolute structure: ?
168 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag20.206133 (14)0.79951 (3)0.660249 (17)0.03620 (8)
O10.17397 (15)0.5366 (3)0.54751 (18)0.0476 (6)
N20.15598 (14)0.8616 (3)0.49573 (18)0.0306 (5)
Ag10.060181 (14)1.13414 (3)0.201582 (18)0.03346 (8)
C10.11079 (17)0.8155 (3)0.3218 (2)0.0269 (6)
C20.08372 (18)0.7496 (4)0.2126 (2)0.0322 (7)
C30.13893 (16)0.7428 (4)0.4199 (2)0.0275 (6)
C40.15067 (17)0.5712 (4)0.4527 (2)0.0323 (7)
C50.13741 (19)0.9977 (4)0.4412 (2)0.0332 (7)
N10.11022 (14)0.9785 (3)0.33560 (18)0.0302 (5)
N30.25466 (19)0.7478 (4)0.8265 (2)0.0366 (6)
N40.0094 (2)1.3080 (4)0.0800 (2)0.0368 (6)
O20.13419 (14)0.4656 (3)0.37827 (19)0.0436 (6)
O30.08142 (16)0.5948 (3)0.20328 (18)0.0480 (6)
O40.06587 (15)0.8395 (3)0.13591 (16)0.0441 (6)
H10.1399 (19)1.094 (4)0.467 (3)0.040 (9)*
H20.112 (4)0.523 (9)0.291 (6)0.17 (3)*
H30.275 (2)0.836 (5)0.869 (3)0.062 (12)*
H40.300 (2)0.686 (5)0.843 (3)0.058 (12)*
H50.218 (2)0.696 (4)0.844 (3)0.042 (10)*
H60.041 (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)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag20.03743 (15)0.04560 (16)0.02245 (12)0.00084 (10)0.00842 (10)0.00281 (10)
O10.0657 (16)0.0373 (12)0.0384 (13)0.0061 (11)0.0189 (12)0.0123 (10)
N20.0315 (13)0.0331 (13)0.0236 (12)0.0025 (10)0.0072 (11)−0.0013 (10)
Ag10.03572 (14)0.03391 (14)0.02914 (13)0.00315 (10)0.01104 (10)0.00742 (9)
C10.0292 (15)0.0262 (14)0.0257 (14)−0.0018 (11)0.0112 (12)−0.0028 (11)
C20.0312 (16)0.0350 (16)0.0281 (15)−0.0025 (13)0.0091 (13)−0.0058 (13)
C30.0238 (14)0.0324 (15)0.0271 (14)0.0005 (11)0.0110 (12)0.0006 (12)
C40.0318 (16)0.0319 (16)0.0357 (16)0.0040 (12)0.0159 (13)0.0032 (13)
C50.0407 (18)0.0283 (16)0.0256 (14)0.0030 (13)0.0076 (13)−0.0036 (12)
N10.0348 (14)0.0288 (12)0.0236 (11)0.0020 (10)0.0078 (11)0.0023 (10)
N30.0409 (17)0.0394 (16)0.0255 (13)−0.0030 (13)0.0087 (13)−0.0003 (12)
N40.0449 (18)0.0308 (15)0.0293 (15)0.0008 (13)0.0089 (14)0.0015 (12)
O20.0585 (15)0.0284 (11)0.0447 (13)0.0004 (10)0.0212 (12)−0.0026 (10)
O30.0710 (17)0.0340 (12)0.0370 (12)−0.0047 (12)0.0189 (12)−0.0112 (10)
O40.0606 (15)0.0428 (13)0.0230 (11)0.0044 (11)0.0100 (11)−0.0014 (10)
Geometric parameters (Å, °) top
Ag1—N12.134 (2)C2—O41.223 (4)
Ag1—N42.123 (3)C2—O31.294 (4)
Ag1—O42.628 (2)C3—C41.487 (4)
Ag2—N22.132 (2)C4—O21.287 (4)
Ag2—N32.133 (3)C5—N11.338 (4)
Ag2—O12.607 (2)C5—H10.87 (4)
Ag1—Ag1i2.9916 (5)N3—H30.92 (4)
Ag1—Ag2ii3.0021 (4)N3—H40.93 (4)
O1—C41.228 (4)N3—H50.90 (4)
N2—C51.325 (4)N4—H60.87 (4)
N2—C31.377 (4)N4—H70.87 (4)
C1—N11.371 (4)N4—H80.77 (5)
C1—C31.373 (4)O2—H21.19 (8)
C1—C21.481 (4)O3—H21.26 (8)
N2—Ag2—N3177.40 (11)C1—C3—C4132.2 (3)
N2—Ag2—O171.12 (8)N2—C3—C4120.0 (2)
N3—Ag2—O1111.27 (10)O1—C4—O2123.4 (3)
N2—Ag2—Ag1iii96.10 (7)O1—C4—C3119.5 (3)
N3—Ag2—Ag1iii82.35 (9)O2—C4—C3117.1 (3)
O1—Ag2—Ag1iii104.71 (6)N2—C5—N1114.1 (3)
C4—O1—Ag2109.3 (2)N2—C5—H1127 (2)
C5—N2—C3105.0 (2)N1—C5—H1119 (2)
C5—N2—Ag2135.2 (2)C5—N1—C1104.3 (2)
C3—N2—Ag2119.74 (19)C5—N1—Ag1134.8 (2)
N4—Ag1—N1173.75 (11)C1—N1—Ag1120.49 (18)
N4—Ag1—O4115.67 (10)Ag2—N3—H3114 (3)
N1—Ag1—O470.43 (8)Ag2—N3—H4109 (2)
N4—Ag1—Ag1i99.91 (10)H3—N3—H4101 (3)
N1—Ag1—Ag1i76.36 (7)Ag2—N3—H5109 (2)
O4—Ag1—Ag1i106.67 (5)H3—N3—H5112 (3)
N4—Ag1—Ag2ii82.99 (10)H4—N3—H5111 (3)
N1—Ag1—Ag2ii99.09 (7)Ag1—N4—H6115 (3)
O4—Ag1—Ag2ii87.07 (6)Ag1—N4—H7111 (3)
Ag1i—Ag1—Ag2ii162.610 (12)H6—N4—H7111 (4)
N1—C1—C3108.8 (2)Ag1—N4—H8112 (4)
N1—C1—C2119.1 (2)H6—N4—H8103 (4)
C3—C1—C2132.0 (3)H7—N4—H8104 (4)
O4—C2—O3122.5 (3)C4—O2—H2113 (3)
O4—C2—C1120.6 (3)C2—O3—H2113 (3)
O3—C2—C1116.9 (3)C2—O4—Ag1108.15 (19)
C1—C3—N2107.8 (2)
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+2, z−1/2; (iii) x, −y+2, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O31.19 (8)1.26 (8)2.448 (3)172 (6)
Table 1
Selected geometric parameters (Å) top
Ag1—N12.134 (2)Ag2—N32.133 (3)
Ag1—N42.123 (3)Ag2—O12.607 (2)
Ag1—O42.628 (2)Ag1—Ag1i2.9916 (5)
Ag2—N22.132 (2)Ag1—Ag2ii3.0021 (4)
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+2, z−1/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O31.19 (8)1.26 (8)2.448 (3)172 (6)
references
References top

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