Bis(1,10-phenanthroline-5,6-dione-κ2 N,N′)silver(I) 2-hy­droxy-3,5-dinitro­benzoate

Shen-Tang Wang; Guang-Bo Che; Chun-Bo Liu; Xing Wang; Ling Liu

doi:10.1107/S1600536811053785

. 2011 Dec 21;68(Pt 1):m76. doi: 10.1107/S1600536811053785

Bis(1,10-phenanthroline-5,6-dione-κ² N,N′)silver(I) 2-hydroxy-3,5-dinitrobenzoate

Shen-Tang Wang ^a, Guang-Bo Che ^a, Chun-Bo Liu ^a,^*, Xing Wang ^a, Ling Liu ^a

PMCID: PMC3254338 PMID: 22259371

Abstract

In the cation of the title salt, [Ag(C₁₂H₆N₂O₂)₂](C₇H₃N₂O₇), the Ag^I atom is coordinated in a distorted tetrahedral geometry by four N atoms from two 1,10-phenanthroline-5,6-dione ligands, while the 3,5-dinitrosalicylate anion has only a short contact [2.847 (6) Å] between one of its O atoms and the Ag^I atom. The dihedral angle between the two 1,10-phenanthroline-5,6-dione ligands is 58.4 (1)°. There is an intramolecular O—H⋯O hydrogen bond in the 3,5-dinitrosalicylate anion.

Related literature

For general background to the structures and potential applications of supramolecular architectures with 1,10-phenantroline-5,6-dione and 3,5-dinitrosalicylic acid, see: Hiort et al. (1993 ▶); Song et al. (2007 ▶); Che et al. (2008 ▶); Onuegbu et al. (2009 ▶). For the synthesis of the 1,10-phenantroline-5,6-dione ligand, see: Dickeson & Sumers (1970 ▶).

Experimental

Crystal data

[Ag(C₁₂H₆N₂O₂)₂](C₇H₃N₂O₇)
M _r = 755.36
Monoclinic,
a = 11.757 (2) Å
b = 18.297 (4) Å
c = 13.223 (3) Å
β = 103.91 (3)°
V = 2761.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 174 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.780, T _max = 0.910
12726 measured reflections
5059 independent reflections
3914 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.163
S = 1.11
5013 reflections
442 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.72 e Å⁻³

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: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053785/vn2025sup1.cif

e-68-00m76-sup1.cif^{(32.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053785/vn2025Isup2.hkl

e-68-00m76-Isup2.hkl^{(240.6KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ag1—N1	2.400 (6)
Ag1—N2	2.351 (6)
Ag1—N3	2.337 (6)
Ag1—N4	2.377 (6)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O8	0.82	1.71	2.457 (9)	151

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Acknowledgments

The authors thank Jiangsu University for supporting this work.

supplementary crystallographic information

Comment

The design and construction of supramolecular architectures have received considerable attention in recent years, mostly motivated by their intriguing structural features and potential applications in molecular adsorption, molecular sensing, magnetism, catalysis and non-linear optics (Che et al., 2008). Metal complexes with 1,10-phenantroline-5,6-dione (L) and 3,5-dinitrosalicylic acid as important ligands for the construction of metal-organic supramolecular architectures have been increasingly studied over recent years (Hiort et al., 1993; Onuegbu et al., 2009; Song et al., 2007). We report herein on the crystal structure of the title compound (Fig. 1). The molecular structure of the title compound, is made up of one [AgL₂]⁺ cation and one 3,5-dinitrosalicylate anion. The Ag^I atom is surrounded by four N atoms from two 1,10-phenanthroline-5,6-dione ligands, while the 3,5-dinitrosalicylate ligand is uncoordinated. In the compound the dihedral angle between the phendione ligand A (C1-C12, N1, N2, O1 and O2) and B (C13-C24, N3, N4, O3, and O4) is 58.4 (1)°. The dihedral angle between B and 3,5-dinitrosalicylate ligand C (C25-C31, N5, N6, O5-O11) is 56.1 (2)°. The dihedral angle between A and C is 2.4 (9)°, suggesting that the planes of rings A and C are almost parallel. In addition, in the 3,5-dinitrosalicylate ligand, there is one intramolecular O–H···O hydrogen bond (Fig. 2).

Experimental

The L ligand was synthesized according to the literature method (Dickeson & Sumers, 1970). The title compound was synthesized under hydrothermal conditions. A mixture of L (0.042 g, 0.2 mmol), 3,5-dinitrosalicylic acid (0.046 g, 0.2 mmol), AgNO₃ (0.034 g, 0.2 mmol) and water (10 mL) was placed in a 25 mL Teflon-lined autoclave and heated for 3 days at 433 K under autogenous pressure. Upon cooling and opening the bomb, yellow block-shaped crystals were obtained, then washed with water and dried in air.