Dichlorido[methyl 2-(quinolin-8-yl­oxy-κ2 N,O)acetate-κO]mercury(II)

Yu-Hong Wang; Xue-Hua Zhu; Rui-Feng Song

doi:10.1107/S1600536812026591

. 2012 Jun 20;68(Pt 7):m951. doi: 10.1107/S1600536812026591

Dichlorido[methyl 2-(quinolin-8-yloxy-κ² N,O)acetate-κO]mercury(II)

Yu-Hong Wang ^a,^*, Xue-Hua Zhu ^a, Rui-Feng Song ^a

PMCID: PMC3393207 PMID: 22807775

Abstract

In the neutral title complex, [HgCl₂(C₁₂H₁₁NO₃)], the Hg^II ion is pentacoordinated by two Cl atoms, one N atom and two weakly coordinating O atoms from the methyl 2-(quinolin-8-yloxy)acetate ligand. The coordination around the Hg^II ion may be described as highly distorted trigonal–bipyramidal. Centrosymmetric dimers are formed by an additional weak Hg⋯Cl interaction, leading to a distorted octahedral coordination geometry around the Hg^II ion.

Related literature

For the use of quinolin-8-yloxy acetic acid and its derivatives as ligands in transition metal complexes, see: Cheng et al. (2007 ▶); Song et al. (2004 ▶); Wang et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

[HgCl₂(C₁₂H₁₁NO₃)]
M _r = 488.71
Triclinic,
a = 7.2644 (4) Å
b = 9.7607 (2) Å
c = 10.8411 (6) Å
α = 71.317 (7)°
β = 75.453 (7)°
γ = 69.816 (8)°
V = 674.87 (5) Å³
Z = 2
Mo Kα radiation
μ = 11.80 mm⁻¹
T = 223 K
0.50 × 0.25 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.067, T _max = 0.385
5090 measured reflections
2432 independent reflections
2330 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.142
S = 1.07
2432 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 3.58 e Å⁻³
Δρ_min = −2.39 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812026591/im2385sup1.cif

e-68-0m951-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026591/im2385Isup2.hkl

e-68-0m951-Isup2.hkl^{(119.5KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Hg1—Cl1	2.340 (2)
Hg1—Cl2	2.350 (2)
Hg1—N1	2.463 (6)
Hg1—O1	2.746 (6)
Hg1—O3	2.876 (6)
Hg1—Cl1ⁱ	3.204 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was supported by the Science and Technology Foundation of the Ministry of Development of China (2010-K6–8).

supplementary crystallographic information

Comment

Quinolin-8-yloxy acetic acid and it's derivatives are well known ligands in transition metal coordination compounds (Cheng et al., 2007; Song et al., 2004; Wang et al., 2005; Wang et al., 2008). Some metal complexes with such ligands are being prepared because of their intriguing structural diversity and potential uses as functional materials (Cheng et al., 2007; Song et al., 2004; Wang et al., 2005; Wang et al., 2008). So, we prepared the title Hg^II complex with methyl-2-(quinoline-8-yloxy)-acetate ligand, (I).

In the title compound, the Hg^II atom is five-coordinated by two Cl atoms, one N atom and two O atoms from methyl-2-(quinoline-8-yloxy)-acetate ligand, forming a highly distorted trigonal bipyramidal geometry (Fig. 1). Hg—Cl bond lengths are 2.340 (2) and 2.350 (2) Å, and Hg—N bond lengths are 2.463 (6) Å. The weak coordinative Hg—O bond lengths are 2.746 (6) Å and 2.876 (6) Å. Angles around Hg are in a range of 56.55 (16)–153.41 (8)° (Table 1). If these are considered to be chemically signifcant interactions, two monoclear Hg complexes are formed into the centrosymmetric dimers by weak Hg—Cl interactions (Fig. 1). So, the coordination around Hg atom can act as a distrorted octahedral geometry.

The molecular packing is controlled by these dimers and intermolecular π-π interactions; the quinoline rings are separated by 3.527 (1) and 3.813 (1) Å (Fig. 2).

Experimental

Quinolin-8-yloxy acetic acid (0.0203 g, 0.1 mmol), HgCl₂ (0.0272 g, 0.1 mmol), methanol (3 ml) and triethylamine (0.0101 g, 0.1 mmol) were placed in a thick Pyrex tube and heated to 130 C° for 5 days. After cooling at a rate of 5 C°/h to ambient temperature, yellow prismatic crystals were collected, washed with anhydrous ethanol, and dried at room temperature. The yield is 51% based on quinolin-8-yloxy acetic acid. Analysis found: C, 29.91; H, 2.30; N, 2.87%; calculated for C₁₂H₁₁Cl₂HgNO₃: C, 29.49; H, 2.27; N, 2.87%.