{2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}copper(II)

Wen-Kui Dong; Jian-Chao Wu; Jian Yao; Shang-Sheng Gong; Jun-Feng Tong

doi:10.1107/S1600536809023010

. 2009 Jun 20;65(Pt 7):m802. doi: 10.1107/S1600536809023010

{2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphtholato}copper(II)

Wen-Kui Dong ^a,^*, Jian-Chao Wu ^a, Jian Yao ^a, Shang-Sheng Gong ^a, Jun-Feng Tong ^a

PMCID: PMC2969428 PMID: 21582727

Abstract

The title complex, [Cu(C₂₆H₂₂N₂O₄)], is isostructural with its Ni analogue. All intramolecular distances and angles are very similar for the two structures, whereas the packing of the molecules, including C—H⋯O and C—H⋯π interactions, are slightly different.

Related literature

For transition metal complexes with multidentate salen-type ligands, see: Akine et al. (2005 ▶); Dong et al. (2009a ▶,b ▶); Katsuki (1995 ▶); Ray et al. (2003 ▶); Sun et al. (2008 ▶). For the isostructural Ni complex, see: Dong et al. (2009c ▶).

Experimental

Crystal data

[Cu(C₂₆H₂₂N₂O₄)]
M _r = 490.00
Monoclinic,
a = 13.0288 (17) Å
b = 7.8934 (12) Å
c = 21.292 (2) Å
β = 103.217 (2)°
V = 2131.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 298 K
0.41 × 0.17 × 0.07 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.670, T _max = 0.929
10698 measured reflections
3753 independent reflections
2278 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.108
S = 1.03
3753 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809023010/at2815sup1.cif

e-65-0m802-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023010/at2815Isup2.hkl

e-65-0m802-Isup2.hkl^{(184KB, 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
C16—H16A⋯O3ⁱ	0.96	2.64	3.375 (5)	134
C23—H23⋯O2ⁱⁱ	0.93	2.43	3.261 (5)	149
C4—H4C⋯Cg8ⁱ	0.96	2.68	3.564 (6)	153

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Symmetry codes: (i) Inline graphic ; (ii) . Cg8 is the centroid of the C21–C26 ring.

Acknowledgments

The authors acknowledge finanical support from the ‘Jing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University.

supplementary crystallographic information

Comment

Transition metal complexes with multidentate salen-type ligands are very interesting in modern coordination chemistry because they have mono-, di- or tri-nuclear metal complexes with important stereochemistry (Katsuki et al., 1995; Akine et al., 2005; Dong et al., 2009b). Metal derivatives of salen-type compounds have been investigated extensively, and copper(II) complexes play a major role in both synthetic and structural research (Ray et al., 2003; Dong et al., 2009a).

In this paper, a new mononuclear copper(II) complex with salen-type bisoxime chelating ligand, 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol, has been synthesized (Sun et al., 2008). The X-ray crystallography of the title complex (Fig. 1) reveals the complex crystallizes in the monoclinic system, with P2₁/c space group. There is a crystallographic twofold screw axis (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z). The dihedral angle between the coordination plane of O3—Cu1—N1 and that of O4—Cu1—N2 is 26.53°, indicating slight distortion toward tetrahedral geometry from the square planar structure [Cu1—O3: 1.876 (3) Å; Cu1—O4: 1.895 (3) Å; Cu1—N1: 1.976 (3) Å; Cu1—N2: 1.947 (3) Å]), with a mean deviation of 0.016 Å from the N₂O₂ plane. The crystal structure is further stabilized by intermolecular C16—H16A···O3, C23—H23···O2 hydrogen bonds and C4—H4C···π interactions (Table 1), which link neighbouring molecules into extended chains along the c axis.

Experimental

A solution of Cu(II) acetate monohydrate (1.7 mg, 0.0085 mmol) in ethanol (5 ml) was added dropwise to a solution of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol (3.4 mg, 0.0079 mmol) in dichloromethane (5 ml). The colour of the mixing solution turns to brown, immediately, and was allowed to stand at room temperature for about one week, the solvent was partially evaporated and obtained dark-brown needle-like single crystals suitable for X-ray crystallographic analysis.