Bis[μ-1,2-bis­(1H-imidazol-1-ylmethyl)benzene-κ2 N 3:N 3′]disilver(I) bis­(4-amino-2,5-dichloro­benzene­sulfonate) tetra­hydrate

Hai-Yan Liu; Yun-Chao Chi; Guang-Hui Wang

doi:10.1107/S1600536808023052

. 2008 Jul 26;64(Pt 8):m1071. doi: 10.1107/S1600536808023052

Bis[μ-1,2-bis(1H-imidazol-1-ylmethyl)benzene-κ² N ³:N ^3′]disilver(I) bis(4-amino-2,5-dichlorobenzenesulfonate) tetrahydrate

Hai-Yan Liu ^a,^*, Yun-Chao Chi ^a, Guang-Hui Wang ^a

PMCID: PMC2961981 PMID: 21203051

Abstract

The asymmetric unit of the title compound, [Ag₂(C₁₄H₁₄N₄)₂](C₆H₄Cl₂NO₃S)₂·4H₂O, contains one-half of each of two independent dicationic units, two 4-amino-2,5-dichlorobenzenesulfonate anions and four water molecules. Each centrosymmetric dicationic unit has a dinuclear structure in which two Ag^I atoms are bridged by two 1,2-bis(1H-imidazol-1-ylmethyl)benzene ligands in a slightly distorted linear coordination geometry. The 4-amino-2,5-dichlorobenzenesulfonate anion does not coordinate with the Ag^I center, acting only as a counteranion. In the crystal structure, intermolecular O—H⋯O and N—H⋯O hydrogen bonds form a three-dimensional network.

Related literature

For related literature, see: Aakeröy & Beatty (1998 ▶); Cote & Shimizu (2004 ▶); Feazell et al. (2006 ▶); Li et al. (2006 ▶); Liu et al. (2007 ▶); Ma et al. (2005 ▶).

Experimental

Crystal data

[Ag₂(C₁₄H₁₄N₄)₂](C₆H₄Cl₂NO₃S)₂·4H₂O
M _r = 1246.51
Triclinic,
a = 11.732 (6) Å
b = 14.598 (6) Å
c = 15.718 (6) Å
α = 79.068 (12)°
β = 72.843 (19)°
γ = 70.991 (17)°
V = 2418.8 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 293 (2) K
0.35 × 0.25 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.716, T _max = 0.753
19762 measured reflections
10576 independent reflections
6897 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.152
S = 0.96
10576 reflections
649 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023052/ci2638sup1.cif

e-64-m1071-sup1.cif^{(34.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023052/ci2638Isup2.hkl

e-64-m1071-Isup2.hkl^{(506.7KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

N2—Ag2	2.092 (3)
N3—Ag2	2.090 (4)
N8—Ag1	2.103 (3)
N9—Ag1	2.100 (3)

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N9—Ag1—N8	175.91 (13)
N3—Ag2—N2	178.95 (15)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2A⋯O6	0.81 (6)	2.15 (7)	2.868 (5)	148 (7)
O3W—H3A⋯O2	0.82 (7)	2.00 (7)	2.819 (6)	172 (9)
O1W—H1A⋯O4ⁱ	0.80 (6)	1.99 (6)	2.762 (5)	165 (7)
N6—H6B⋯O2ⁱⁱ	0.80 (3)	2.19 (4)	2.928 (5)	154 (6)
N5—H5B⋯O5ⁱⁱⁱ	0.81 (6)	2.28 (6)	2.913 (5)	136 (5)

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

Acknowledgments

The authors thank the Science Foundation of Suihua University (grant No. K071001) for supporting this work.

supplementary crystallographic information

Comment

Ag^I complexes have shown versatility of their coordination geometry (Aakeröy & Beatty, 1998; Ma et al., 2005). Some silver(I) sulfonate compounds, modified by secondary nitrogen-based ligands, have been reported (Cote & Shimizu, 2004; Liu et al., 2007). Herein, we present a new silver-sulfonate complex, namely [Ag₂(IBI)₂]L₂.4H₂O, where IBI is 1,2-bis ((1H-imidazol-1-yl)methyl)benzene and L is 4-amino-2,5-dichlorobenzenesulfonic acid.

Selected bond distances and angles are listed in Table 1. The asymmetric unit of the title compound contains one-half each of two independent dicationic units, two 4-amino-2,5-dichlorobenzenesulfonate anions and four water molecules. Each Ag^I ion is two-coordinated by two N atoms from two IBI ligands, showing a slightly distorted linear geometry. The Ag—N bond distances are within the normal range observed in N-containing Ag^I complexes (Li et al., 2006; Feazell et al., 2006). The L anion does not coordinate with silver ion but acts as a counteranion.

N—H···O and O—H···O hydrogen bonds between water molecules and L ligands result in the formation of a three-dimensional supramolecular structure (Table 2).

Experimental

An aqueous solution (10 ml) of 4-amino-2,5-dichlorobenzenesulfonic acid (1 mmol) was added to solid Ag₂CO₃ (0.5 mmol) and stirred for several minutes until no further CO₂ was given off. 1-(3-(1H-Imidazol-1-yl)methyl)benzyl)-1H-imidazole (1 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Single crystals of the title compound were obtained by slow evaporation of the solution for 6 d at room temperature.