Bis{2-meth­oxy-6-[(3-methoxy­prop­yl)imino­meth­yl]phenolato-κ2 N,O 1}copper(II)

Amitabha Datta; Jui-Hsien Huang; Hon Man Lee

doi:10.1107/S1600536808035289

. 2008 Nov 8;64(Pt 12):m1497. doi: 10.1107/S1600536808035289

Bis{2-methoxy-6-[(3-methoxypropyl)iminomethyl]phenolato-κ² N,O ¹}copper(II)

Amitabha Datta ^a, Jui-Hsien Huang ^a, Hon Man Lee ^a,^*

PMCID: PMC2959917 PMID: 21581118

Abstract

The title complex, [Cu(C₁₂H₁₆NO₃)₂], adopts a distorted square-planar coordination geometry with the Cu^II ion situated on a crystallographic inversion center. The two Schiff base ligands are coordinated in a trans fashion. In the crystal structure, non-classical intermolecular C—H⋯O hydrogen bonds involving the ether O atoms link the Schiff base molecules into a two-dimensional network parallel to (101).

Related literature

For similar copper(II) structures with Schiff base ligands: see: Akitsu & Einaga (2004 ▶); Bluhm et al. (2003 ▶); Castiñeiras et al. (1990 ▶); Costamagna et al. (1998 ▶); King et al. (1973 ▶); Lacroix et al. (2004 ▶); Zhang et al. (2001 ▶).

Experimental

Crystal data

[Cu(C₁₂H₁₆NO₃)₂]
M _r = 508.06
Monoclinic,
a = 11.2189 (9) Å
b = 10.7004 (8) Å
c = 9.5002 (7) Å
β = 96.912 (1)°
V = 1132.18 (15) Å³
Z = 2
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 100 (2) K
0.50 × 0.50 × 0.40 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.614, T _max = 0.668
6343 measured reflections
2298 independent reflections
2065 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.079
S = 1.09
2298 reflections
153 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); 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 I, global. DOI: 10.1107/S1600536808035289/lh2719sup1.cif

e-64-m1497-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035289/lh2719Isup2.hkl

e-64-m1497-Isup2.hkl^{(113KB, 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
C8—H8B⋯O3ⁱ	0.98	2.58	3.476 (2)	151
C9—H9A⋯O1ⁱⁱ	0.99	2.31	2.782 (2)	108
C9—H9B⋯O3	0.99	2.55	2.918 (2)	102

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We are grateful to the National Science Council of Taiwan for financial support.

supplementary crystallographic information

Comment

The Schiff base (E)-2-methoxy-6-[(3-methoxypropyl)iminomethyl]phenol reacts with copper(II) nitrate in methanol to form the title complex. In situ deprotonation of the phenolic hydrogen occurred leading to formation of the O/N-bidentate ligand. The title complex consists of two bidentate ligands coordinating in a trans fashion. It adopts a square-planar coordination geometry with the Cu atom located on a crystallographic inversion center. Schiff base Cu(II) complexes similar to the title complex have been reported in the literature (Akitsu & Einaga, 2004; Bluhm et al., 2003; Castiñeiras et al., 1990; Costamagna et al., 1998; King et al., 1973; Lacroix et al., 2004; Zhang et al., 2001).

Both intramolecular and intermolecular non-classical H-bonds of the type C-H···O exist (Table 1). The intermolecular H-bonds link the complex into a two-dimensional network.

Experimental

Synthesis of (E)-2-methoxy-6-((3-methoxypropylimino)methyl)phenol: The compound was synthesized by the condensation reaction between O-vaniline and NH₂(CH₂)₃OMe in methanol. After complete removal of the solvent, the resulting yellow liquid was used without purification.

Synthesis of the title complex: A methanolic solution of Cu(NO₃)₂ (1 mmol, 188 mg) and (E)-2-methoxy-6-((3-methoxypropylimino)methyl)phenol (2 mmol, 446 mg) was stirred for 30 min. The solution was then kept for 7 days to yield crystals suitable for X-ray diffraction study.