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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1523.
Published online 2009 November 7. doi:  10.1107/S1600536809045747
PMCID: PMC2972141

(μ-5-Carb­oxy-1H-imidazole-4-carboxyl­ato-κ4 N 1,O 5:N 3,O 4)bis­[amminesilver(I)]

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1523-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C5H2N2O4)(NH3)2]
  • M r = 403.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1523-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported by the Doctoral Foundation of North University of China.

supplementary crystallographic information

Comment

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).

Experimental

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

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

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The one-dimensional puckered chain assembled by Ag tetramers and 4,5-imidazoledicarboxylate ligands. Dashed lines denote Ag···Ag interactions.

Crystal data

[Ag2(C5H2N2O4)(NH3)2]F(000) = 1536
Mr = 403.89Dx = 2.790 Mg m3
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 mm1
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

Bruker SMART APEX CCD diffractometer1911 independent reflections
Radiation source: fine-focus sealed tube1721 reflections with I > 2σ(I)
graphiteRint = 0.019
[var phi] 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

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 = 1.05w = 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 Å3
0 restraintsΔρmin = −0.50 e Å3

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

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O31.19 (8)1.26 (8)2.448 (3)172 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2243).

References

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