cis-Aqua­bis(2,4-dichloro-6-formyl­phenolato-κ2 O,O′)(N,N-dimethyl­formamide-κO)nickel(II)

Fa-Yun Chen; Shu-Hua Zhang; Chen-Min Ge

doi:10.1107/S1600536808022939

. 2008 Jul 26;64(Pt 8):m1068. doi: 10.1107/S1600536808022939

cis-Aquabis(2,4-dichloro-6-formylphenolato-κ² O,O′)(N,N-dimethylformamide-κO)nickel(II)

Fa-Yun Chen ^a, Shu-Hua Zhang ^b,^*, Chen-Min Ge ^b

PMCID: PMC2961979 PMID: 21203049

Abstract

In the title compound, [Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)], the Ni^II ion is coordinated by four O atoms from two bidentate 2,4-dichloro-6-formylphenolate ligands, one O atom from a water ligand and one O atom from a dimethylformamide ligand in a slightly distorted octahedral environment. In the crystal structure, centrosymmetric dimers are formed though O—H⋯O and O—H⋯Cl hydrogen bonds; π–π stacking interactions, with a centroid–centroid distance of 3.796 (2) Å, are also found.

Related literature

For related literature, see: Cohen et al. (1964 ▶); Desiraju (1989 ▶); Mathews & Manohar (1991 ▶); Zaman et al. (2004 ▶); Zhang et al. (2007 ▶); Zordan et al. (2005 ▶).

Experimental

Crystal data

[Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)]
M _r = 529.81
Monoclinic,
a = 10.404 (2) Å
b = 9.6130 (19) Å
c = 22.161 (4) Å
β = 92.44 (3)°
V = 2214.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 293 (2) K
0.48 × 0.40 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.555, T _max = 0.642
10765 measured reflections
3969 independent reflections
3010 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.111
S = 1.07
3969 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022939/lh2644sup1.cif

e-64-m1068-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022939/lh2644Isup2.hkl

e-64-m1068-Isup2.hkl^{(194.6KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni1—O3	2.041 (2)
Ni1—O1	2.041 (2)
Ni1—O2	2.061 (3)
Ni1—O4	2.070 (3)
Ni1—O5	2.148 (3)
Ni1—O6	2.150 (3)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1ⁱ	0.82	1.91	2.714 (3)	168
O6—H6B⋯O3ⁱ	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B⋯Cl3ⁱ	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the Natural Science Foundation of Guangxi Province, China (grant No. 0832085).

supplementary crystallographic information

Comment

Halogens have a ubiquitous presence in both inorganic and organic chemistry. Schiff bases of chloro substituents on aromatic groups have aroused increasing interest in recent years because these halogenated compounds are an attractive target for use in supramolecular chemistry and crystal engineering wherein the halogen atoms are directly involved in forming intermolecular interactions (Cohen et al., 1964; Zordan et al., 2005; Desiraju, 1989; Zaman et al., 2004; Zhang et al., 2007). The title compound, (I), contains the dichloride ligand 3,5-Dichloro-2-hydroxy-benzaldehyde, with two Cl atoms accessible at the periphery of each ligand.

In the molecular structure of (I), the Ni^II ion is coordinated by four O atoms from two bidentate 3,5-Dichloro-2-hydroxy-benzaldehyde ligands, one O atom from a H₂O ligand and one O atom from a N,N'-dimethylformamide ligand forming a slightly distorted octahedral geometry (Fig. 1). In the crystal structure O—H···O and O—H···Cl hydrogen bonds (see Table 2) result in the formation of a centrosymmetric dimer (Fig. 2). Within the dimer, there are π–π stacking interactions between the C1–C6 and C8–C13(-x, 2-y, 1-z) rings with centroid···centroid distance of 3.796 (2) Å and interplanar distance of 3.59 Å giving an offset angle of 3.5°. In the crystal structure, dimers are further linked through weak intermolecular C—H···O hydrogen bonds (Fig. 3) (C5—H5A···O4ⁱⁱ, 3.454 Å, symmetry code: (ii) 1 + x, 2 - y, 1 + z).

Experimental

A ethanol solution (30 ml) containing 3,5-Dichloro-2-hydroxy-benzaldehyde (0.191 g, 1 mmol) was dropwise added to an aqueous solution containing amino-methanesulfonic acid (0.111 g, 1 mmol) and sodium hydroxide (0.040 g, 1 mmol) with stirred during 10 min. After stirring for 1 h, an aqueous solution of Nickel chloride (0.237 g, 1 mmol) was added to the resulting solution and stirred for 2 h. The green solid compound was separated out and dissolved by N,N-Dimethylformamide, then the green solution was filtrated. After 10 days, green crystals were produced from the filtrate (yield: 65.3%, based on Ni).