Bis[bis(1H-imidazole-κN 3)silver(I)] naphthalene-1,5-disulfonate

Ping Liu; Dong-Sheng Deng

doi:10.1107/S1600536808006855

. 2008 Mar 14;64(Pt 4):m556. doi: 10.1107/S1600536808006855

Bis[bis(1H-imidazole-κN ³)silver(I)] naphthalene-1,5-disulfonate

Ping Liu ^a, Dong-Sheng Deng ^b,^*

PMCID: PMC2961055 PMID: 21202012

Abstract

The title compound, [Ag(C₃H₄N₂)₂]₂(C₁₀H₆O₆S₂), exists in the form of isolated cations and anions with electrostatic interaction between them. The Ag atom is two-coordinated by the N atoms of two crystallographically independent imidazole molecules. The naphthalene-1,5-disulfonate anion is located on a crystallographic center of symmetry. The cations and anions are connected through intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Côté & Shimizu (2003 ▶, 2004 ▶); Cai (2004 ▶); Cai et al. (2001 ▶); Chen et al. (2001 ▶, 2002 ▶); Dalrymple & Shimizu (2002 ▶); Lian et al. (2007 ▶); Liu et al. (2006 ▶); Reddy et al. (2003 ▶); Shimizu et al. (1999 ▶); Zhou et al. (2004 ▶).

Experimental

Crystal data

[Ag(C₃H₄N₂)₂]₂(C₁₀H₆O₆S₂)
M _r = 774.36
Triclinic,
a = 8.6491 (11) Å
b = 9.0196 (12) Å
c = 10.2620 (13) Å
α = 65.286 (2)°
β = 76.311 (2)°
γ = 66.791 (2)°
V = 665.89 (15) Å³
Z = 1
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 293 (2) K
0.50 × 0.30 × 0.13 mm

Data collection

Bruker Smart 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.487, T _max = 0.811
4267 measured reflections
2962 independent reflections
2417 reflections with I > 2σ(I)
R _int = 0.010

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.063
S = 0.93
2962 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006855/rk2068sup1.cif

e-64-0m556-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006855/rk2068Isup2.hkl

e-64-0m556-Isup2.hkl^{(145.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O2ⁱ	0.86	1.96	2.786 (3)	161
N2—H2A⋯O3ⁱⁱ	0.86	2.37	2.998 (3)	130
N2—H2A⋯O3ⁱⁱⁱ	0.86	2.32	3.082 (3)	149

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the Henan Institute of Science and Technology for financial support and we thank Professor Ji-Wen Cai for his guidance.

supplementary crystallographic information

Comment

In the part of our recent investigations into the development of mixed inorganic–organic hybrid materials, we synthesized the silver sulfonate compound, which can be possess a potential wide chemical opportunity.

Sulfonate compounds have received much attention due to their potential application in chemical absorption and separation (Cai et al., 2004; Zhou et al., 2004; Liu et al., 2006). However, the weak coordination nature of SO₃–group makes its coordination mode very flexible and sensitive to the chemical environment (Côté et al., 2003). Likewise, Ag⁺ ion is a notoriously pliant with respect to its coordination sphere. Thus, in silver sulfonates, various coordination modes are observed with coordination number ranging from two to nine (Côté et al., 2004; Dalrymple et al., 2002; Reddy et al., 2003; Shimizu et al., 1999). On the other hand, the coordination behavior of arene–sulfonates with transition metals can be peculiar in the presence of amino ligands (Chen et al., 2001; Cai et al., 2001; Chen et al., 2002).

The structure of the title compound, (I), is depicted in Fig. 1. There is one crystallographically independent Ag centre, coordinated by two nitrogen atoms from two different imidazole ligands with Ag—N1 = 2.1088 (19)Å and Ag—N2 = 2.109 (2) Å, respectively. The lesser contact distance Ag···O1 = 2.8185 (19)Å is longer than the reported Ag···O distance (Lian et al., 2007).

Cations and anions are connected through intermolecular N—H···O hydrogen bonds to form a linear tapes (N4—H4A···O2ⁱⁱ): N4···O2ⁱⁱ = 2.786 (3) Å, H4A···O2ⁱⁱ = 1.96Å and angle N4—H4A···O2ⁱⁱ = 160.7°, which run along the a–axis. The linear tapes are arranged in parallel fashion and further linked via hydrogen bonding between the coordinated imidazole molecules and the sulfonate oxygen atoms, thus leading to neutral extended two–dimensional sheets (N2—H2A···O3ⁱⁱⁱ): N2···O3ⁱⁱⁱ = 2.998 (3) Å, angle N2—H2A···O3ⁱⁱⁱ = 129.8° and (N2—H2A···O3^iv): N2···O3^iv = 3.082 (3) Å, angle N2—H2A···O3^iv = 148.6° as shown on Fig. 2 (symmetry codes: (ii) 1 + x, y, z); (iii) x - 2, y + 1, z; (iv) -x, 2 - y, 2 - z).

Experimental

Disodium 1,5–naphthalene–disulfonate (0.33 g, 1 mmol) and imidazole (0.27 g, 4 mmol) were added to an aqueous solution of AgNO₃ (0.32 g, 2 mmol) (10 ml). The result solution was stirred at 343 K for four hours in a water bath. After filtration, a clear solution was set aside to crystallize.