Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands

Qiaozhen Sun; Feng Zheng; Xiaodan Sun; Wei Wang

doi:10.1107/S1600536809004760

. 2009 Feb 18;65(Pt 3):m283–m284. doi: 10.1107/S1600536809004760

Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands

Qiaozhen Sun ^a,^*, Feng Zheng ^a, Xiaodan Sun ^a, Wei Wang ^a

PMCID: PMC2968493 PMID: 21582069

Abstract

The new ligand 1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol (L) and the title silver(I) complex, namely bis[μ-1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol]bis{[1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol]silver(I)} dinitrate monohydrate, [Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O, were synthesized. Each silver center in the dimeric complex (related by an inversion centre) is coordinated by two bridging L ligands and one additional L ligand in a monodentate fashion, exhibiting a distorted trigonal-planar coordination. The discrete dimers are further linked through O—H⋯O hydrogen bonds and weak π–π stacking interactions [the shortest atom–atom separation is ca 3.46 Å between the parallel stacking pairs]. Intramolecular O—H⋯N hydrogen bonds are also present.

Related literature

For the structures of other triazole Schiff base compounds, see: Beckmann & Brooker (2003 ▶); Drabent et al. (2003 ▶, 2004 ▶); Garcia et al. (1997 ▶); Klingele & Brooker (2003 ▶); Liu et al. (2003 ▶, 2006 ▶); Wang et al. (2006 ▶); Yi et al. (2004 ▶); Zhai et al. (2006 ▶). For related literature, see: Han et al. (2004 ▶).

Experimental

Crystal data

[Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O
M _r = 1310.78
Triclinic,
a = 9.8594 (15) Å
b = 10.7081 (15) Å
c = 12.8567 (19) Å
α = 82.391 (2)°
β = 81.155 (2)°
γ = 77.626 (2)°
V = 1303.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.826, T _max = 0.887
6610 measured reflections
4536 independent reflections
3137 reflections with I > 2σ(I)
R _int = 0.118

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.133
S = 1.00
4536 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004760/wk2097sup1.cif

e-65-0m283-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004760/wk2097Isup2.hkl

e-65-0m283-Isup2.hkl^{(222.2KB, 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
O1—H1A⋯N1	0.82	1.83	2.548 (4)	145
O2—H2B⋯N5	0.82	1.87	2.588 (5)	145
O1W—H1WA⋯O3ⁱ	0.85	1.85	2.594 (15)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the financial support from the Innovation Program for College Students of Central South University (grant No. 081053308).

supplementary crystallographic information

Comment

1,2,4-triazoles and their derivatives are interesting bridging ligands. 1,2,4-triazoles can coordinate with metals by bridging two adjacent nitrogen atoms (N1 and N2) or via the 4-positioned one (N4). It is also a readily available and inexpensive resource. In the past two decades, a variety of coordination compounds containing 1,2,4-triazoles, N4 substituted 1,2,4-triazoles and their derivatives as ligands coordinated to metal ions have been reported (Beckmann & Brooker, 2003; Garcia et al., 1997; Klingele & Brooker, 2003; Liu et al., 2006; Liu et al., 2003; Yi et al., 2004; Zhai et al., 2006). Relatively few structurally characterized compounds based on 4-amido-1,2,4-triazoles Schiff base ligands have been reported (Drabent et al., 2004 and 2003; Wang et al., 2006). Here we describe the synthesis of the Ag(I) metal complex with a Schiff-base containing triazole ligand.

The molecular structure of complex 1 is shown in Figure 1. It consists of a discrete binuclear complex of Ag(I) bridged by two N1,N2-coordinated triazole ligands and an additional triazole ligand is bound to the Ag(I) ion in a monodentate fashion. This coordination mode results in a trigonal planar coordination environment (the sum of the angles around Ag metal atom is equal to 360 °). The Ag—Ag distance is equal to 3.81 Å, which is over the summed van der Waals radii of two Ag(I) atoms (3.44 Å) (Han et al., 2004). The Ag—N bond distances are in the range of 2.18–2.33 Å. The six-membered Ag-[N—N]₂-Ag rings remain almost planar (the mean plane deviation is 0.06 Å) from planarity, which is similar withdinuclear Cu(I) complex (Drabent et al., 2004). The Ag—N—N—Ag dihedral angle is 15.1 °.

In this complex all the ligands L are coordinated in almost planar E configuration and the resulting binuclear units can be described as X-shaped dimers. Sheets formed through C-H···O hydrogen bonds are further aggregated into three-dimensions by weak π-π stacking interactions between the naphthyl rings of the neighbouring dimers in different sheets and the shortest atom···atom separation is ca 3.46 Å between the parallel stacking pairs. The anions and water molecules interact with one another through O—H···N, O—H···O hydrogen bonds.

Experimental

Preparation of complex 1: The ligand L (0.1 mmol, 0.024 g) and AgNO₃ (0.1 mmol, 0.017 g) were mixed in acetonitrile and stirred at room temperature for one hour, the yellow solution was filtered and evaporated at room temperature. A few days later orange block crystals were obtained.

Preparation of the ligand L: An ethanolic solution (20 ml) of 2-hydroxy-1-napthaldehyde (1.72 g, 10 mmol) was added to a warm ethanolic solution (10 ml) of 4-amino- 1,2,4-triazole (0.84 g, 10 mmol) and the resulting solution was refluxed for four hours. The reaction mixture was then cooled to room temperature. Upon standing overnight the resultant yellow solid was filtered off, washed with diethyl ether and dried under vacuum. Yield: 90%. ¹H NMR (500 MHz, DMSO, 298 K): 9.66 (s, 1H), 9.34 (s, 2H), 8.84–8.86 (d, 1H), 8.05–8.07 (d, 1H), 7.90–7.92 (d, 1H), 7.61–7.64 (t, 1H), 7.43–7.46 (t, 1H), 7.28–7.30 (d, 1H).