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

Zhou, R.-S.; Song, J.-F.

doi:10.1107/S1600536809045747

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1523

doi:10.1107/S1600536809045747

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

Rui-Sha Zhou ^a and Jiang-Feng Song ^a ^*

^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 Ag^I 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 ); 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_r = 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 ) 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[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
Δρ_max = 0.45 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
O2—H2⋯O3	1.19 (8)	1.26 (8)	2.448 (3)	172 (6)

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).

Supporting information

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

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

checkCIF report

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 Ag^I complex built with 4,5-imidazoledicarboxylic acid ligand.

The asymmetric unit consists of two crystallographically independent Ag^I atoms, one partly deprotonated 4,5-imidazoledicarboxylate ligand and two ammonia molecules (Fig. 1). Each Ag^I 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 Ag^I 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.

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

	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.

(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
M_r = 403.89	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.02P)² + 2.4121P] where P = (F_o² + 2F_c²)/3
1911 reflections	(Δ/σ)_max = 0.001
168 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Ag₂(C₅H₂N₂O₄)(NH₃)₂]	V = 1922.9 (2) Å³
M_r = 403.89	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.3800 (12) Å	µ = 4.07 mm⁻¹
b = 8.3243 (5) Å	T = 190 K
c = 13.6696 (8) Å	0.35 × 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)
T_min = 0.330, T_max = 0.686	R_int = 0.019
5211 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.044	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.45 e Å⁻³
1911 reflections	Δρ_min = −0.50 e Å⁻³
168 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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, º) top

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)

Experimental details

Crystal data
Chemical formula	[Ag₂(C₅H₂N₂O₄)(NH₃)₂]
M_r	403.89
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	190
a, b, c (Å)	18.3800 (12), 8.3243 (5), 13.6696 (8)
β (°)	113.160 (1)
V (Å³)	1922.9 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.07
Crystal size (mm)	0.35 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.330, 0.686
No. of measured, independent and observed [I > 2σ(I)] reflections	5211, 1911, 1721
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.044, 1.05
No. of reflections	1911
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—N1	2.134 (2)	Ag2—N3	2.133 (3)
Ag1—N4	2.123 (3)	Ag2—O1	2.607 (2)
Ag1—O4	2.628 (2)	Ag1—Ag1ⁱ	2.9916 (5)
Ag2—N2	2.132 (2)	Ag1—Ag2ⁱⁱ	3.0021 (4)

Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y+2, z−1/2.

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

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

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