metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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(μ-5-Carb­­oxy-1H-imidazole-4-carboxyl­ato-κ4N1,O5:N3,O4)bis­­[amminesilver(I)]

aDepartment of Chemistry, North University of China, Taiyuan Shanxi 030051, People's Republic of China
*Correspondence e-mail: jfsong0129@gmail.com

(Received 11 October 2009; accepted 31 October 2009; online 7 November 2009)

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[Ferey, G. (2008). Chem. Soc. Rev. 37, 191-241.]); Ma et al. (2009[Ma, L. Q., Abney, C. & Lin, W. B. (2009). Chem. Soc. Rev. 38, 1248-1256.]); Moulton & Zaworotko (2001[Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629-1658.]); Tranchemontagne et al. (2009[Tranchemontagne, D. J., Mendoza-Cortes, J. L., O'Keeffe, M. & Yaghi, O. M. (2009). Chem. Soc. Rev. 38, 1257-1283.]). For related structures with the 4,5-imidazole­dicarboxylic acid ligand, see: Caudle et al. (1997[Caudle, M. T., Kampf, J. W., Kirk, M. L., Rasmussen, P. G. & Pecoraro, V. L. (1997). J. Am. Chem. Soc. 119, 9297-9298.]); Fang & Zhang (2006[Fang, R.-Q. & Zhang, X.-M. (2006). Inorg. Chem. 45, 4801-4810.]); Han et al. (2005[Han, J.-L., Shen, Y.-Z., Li, C.-X., Li, Y.-Z. & Pan, Y. (2005). Inorg. Chim. Acta, 358, 4417-4422.]); Zhong et al. (2006[Zhong, R.-Q., Zou, R.-Q. & Xu, Q. (2006). Acta Cryst. E62, m2789-m2790.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag2(C5H2N2O4)(NH3)2]

  • Mr = 403.89

  • Monoclinic, C 2/c

  • 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.330, Tmax = 0.686

  • 5211 measured reflections

  • 1911 independent reflections

  • 1721 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.018

  • wR(F2) = 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

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) [-x, y, -z+{\script{1\over 2}}]; (ii) [x, -y+2, z-{\script{1\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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 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 top
Bruker SMART APEX CCD
diffractometer
1911 independent reflections
Radiation source: fine-focus sealed tube1721 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ϕ and ω scansθmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 2218
Tmin = 0.330, Tmax = 0.686k = 109
5211 measured reflectionsl = 1616
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 Å3
0 restraintsΔρmin = 0.50 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0180 restraints
wR(F2) = 0.044H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.45 e Å3
1911 reflectionsΔρmin = 0.50 e Å3
168 parameters
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)*
H70.034 (3)1.348 (5)0.083 (3)0.060 (13)*
H80.004 (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, º) 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, z1/2; (iii) x, y+2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O31.19 (8)1.26 (8)2.448 (3)172 (6)

Experimental details

Crystal data
Chemical formula[Ag2(C5H2N2O4)(NH3)2]
Mr403.89
Crystal system, space groupMonoclinic, C2/c
Temperature (K)190
a, b, c (Å)18.3800 (12), 8.3243 (5), 13.6696 (8)
β (°) 113.160 (1)
V3)1922.9 (2)
Z8
Radiation typeMo Kα
µ (mm1)4.07
Crystal size (mm)0.35 × 0.25 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.330, 0.686
No. of measured, independent and
observed [I > 2σ(I)] reflections
5211, 1911, 1721
Rint0.019
(sin θ/λ)max1)0.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.018, 0.044, 1.05
No. of reflections1911
No. of parameters168
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.50

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (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, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O31.19 (8)1.26 (8)2.448 (3)172 (6)
 

Acknowledgements

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

References

First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCaudle, M. T., Kampf, J. W., Kirk, M. L., Rasmussen, P. G. & Pecoraro, V. L. (1997). J. Am. Chem. Soc. 119, 9297–9298.  CSD CrossRef CAS Web of Science Google Scholar
First citationFang, R.-Q. & Zhang, X.-M. (2006). Inorg. Chem. 45, 4801–4810.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationFerey, G. (2008). Chem. Soc. Rev. 37, 191–241.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHan, J.-L., Shen, Y.-Z., Li, C.-X., Li, Y.-Z. & Pan, Y. (2005). Inorg. Chim. Acta, 358, 4417–4422.  Web of Science CSD CrossRef CAS Google Scholar
First citationMa, L. Q., Abney, C. & Lin, W. B. (2009). Chem. Soc. Rev. 38, 1248–1256.  Web of Science CrossRef PubMed CAS Google Scholar
First citationMoulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629–1658.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTranchemontagne, D. J., Mendoza-Cortes, J. L., O'Keeffe, M. & Yaghi, O. M. (2009). Chem. Soc. Rev. 38, 1257–1283.  Web of Science CrossRef PubMed CAS Google Scholar
First citationZhong, R.-Q., Zou, R.-Q. & Xu, Q. (2006). Acta Cryst. E62, m2789–m2790.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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