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

Yan Yang; Guohui Yuan

doi:10.1107/S1600536811018691

. 2011 May 25;67(Pt 6):m802. doi: 10.1107/S1600536811018691

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

Yan Yang ^a,^*, Guohui Yuan ^b

PMCID: PMC3120420 PMID: 21754678

Abstract

In the title compound, [Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O, the dinuclear dication has crystallographically imposed inversion symmetry. Each Ag^I ion is bicoordinated in a slightly distorted linear coordination geometry by the N atoms of two ligands, resulting in the formation of a 22-membered metallamacrocycle. In the dication, π–π interactions are observed between the imidazole rings, with centroid–centroid distances of 3.528 (3) Å and dihedral angles of 9.92 (9)°. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds and π–π interactions involving the benzene rings of adjacent dications, with centroid–centroid distances of 3.651 (2) Å.

Related literature

For the synthesis and structures of related compounds, see: Tan et al. (2004 ▶); Liu et al. (2007 ▶); Liu, Ma et al. (2008 ▶); Liu, Chi & Wang (2008 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

[Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O
M _r = 1194.74
Triclinic,
a = 9.6644 (5) Å
b = 11.3769 (12) Å
c = 11.8255 (5) Å
α = 109.376 (8)°
β = 95.783 (3)°
γ = 94.442 (4)°
V = 1211.79 (15) Å³
Z = 1
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 K
0.15 × 0.12 × 0.11 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.35, T _max = 0.59
8572 measured reflections
4904 independent reflections
3384 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.069
S = 0.89
4904 reflections
346 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018691/rz2589sup1.cif

e-67-0m802-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018691/rz2589Isup2.hkl

e-67-0m802-Isup2.hkl^{(235.3KB, 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
O2—H2A⋯O3ⁱ	0.82	1.69	2.496 (2)	166
O1W—HW11⋯O4	0.87 (2)	1.96 (2)	2.814 (3)	166 (3)
O1W—HW12⋯O2Wⁱⁱ	0.83 (2)	2.12 (2)	2.902 (3)	158 (3)
O2W—HW21⋯O1	0.84 (2)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22⋯O3ⁱ	0.88 (2)	2.13 (3)	2.841 (3)	138 (3)

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

Acknowledgments

The authors thank Tonghua Normal University for financial support.

supplementary crystallographic information

Comment

The design and synthesis of silver(I) complexes have attracted intense interests of chemists (Liu, Chi & Wang, 2008; Tan et al., 2004) because of the versatility of their coordination geometry (Sun et al., 2009). So far, some complexes, modified by secondary nitrogen-based ligands, have been reported (Liu et al., 2007). In this work, the combination of 1,2-bis(1H-imidazol-1-ylmethyl)benzene (1,2-bix) with naphthalene-1,4-dicarboxylic acid (1,4-H₂ndc) and silver(I) ions resulted in the title compound, whose synthesis and structure are reported herein.

The contents of the asymmetric unit of the title compound is shown in Fig. 1. The complex, which has crystallographically imposed inversion symmetry, shows a binuclear structure, where each of silver(I) atom has a slightly distorted linear geometry and is coordinated by the N atoms from two 1,2-bix ligands. The Ag-N bond distances are within the normal range and are comparable to those observed in related N-containing compounds (Liu, Ma et al., 2008). Notably, the 1,4-Hndc anion does not coordinate to the metal and acts as a counter-anion. In the dication, π-π interactions are observed between the imidazole rings (N1/N2/C1–C3 and N3/N4/C12–C14), with centroid-centroid distance of 3.528 (3) Å and dihedral angles of 9.92 (9)°. The crystal structure is stabilized by a three-dimensional network of intermolecular O—H···O hydrogen bonds (Table 1) and π-π interactions involving the benzene rings of adjacent dications, with centroid-to-centroid distances Cg1···Cg1ⁱ = 3.651 (2) Å [Cg1 is the centroid of the C5–C10 ring; symmetry code: (i) 1-x, -y, 1-z].

Experimental

A mixture of AgNO₃^.2H₂O (0.5 mmol), naphthalene-1,4-dicarboxylic acid (0.5 mmol), 1,2-bis(1H-imidazol-1-ylmethyl)benzene (0.5 mmol) in H₂O (12 ml) was adjusted to pH = 5-6 by addition of aqueous NaOH solution, and heated at 145°C for 2 days. After the mixture was slowly cooled to room temperature, crystals of the title compound suitable for X-ray analysis were obtained (yield 33%).