Bis(acetato-κO)bis­[2-(pyridin-2-yl)ethanol-κ2 N,O]copper(II)

Katja Lapanje; Ivan Leban; Nina Lah

doi:10.1107/S1600536812015747

. 2012 Apr 18;68(Pt 5):m599. doi: 10.1107/S1600536812015747

Bis(acetato-κO)bis[2-(pyridin-2-yl)ethanol-κ² N,O]copper(II)

Katja Lapanje ^a, Ivan Leban ^a, Nina Lah ^a,^*

PMCID: PMC3344340 PMID: 22590106

Abstract

The title compound, [Cu(CH₃COO)₂(C₇H₉NO)₂], is a monomeric complex with an octahedral geometry. The Cu^II atom is located on an inversion center and is coordinated by acetate and 2-(pyridin-2-yl)ethanol ligands. The acetate group is coordinated in a monodentate manner, while the 2-(pyridin-2-yl)ethanol is coordinated as a bidentate ligand involving the endocyclic N atom and the hydroxy O atom of the ligand side chain. An intramolecular hydrogen bond is observed between the hydroxy O atom and the non-coordinated acetate O atom. No classical intermolecular hydrogen-bond contacts were observed. However, the crystal packing is effected by C—H⋯O interactions, which link the mononuclear entities into layers parallel to the bc plane.

Related literature

For related structures, see: Pothiraja et al. (2011 ▶); Yilmaz et al. (2003 ▶). For copper halogenido complexes with 2-(pyridin-2-yl)ethanol, see: Hamamci et al. (2004 ▶); Lah & Leban (2010 ▶). For copper complexes with acetate and 2-(pyridin-2-yl)ethanol in its deprotonated form, see, for example: Mobin et al. (2010 ▶).

Experimental

Crystal data

[Cu(C₂H₃O₂)₂(C₇H₉NO)₂]
M _r = 427.93
Monoclinic,
a = 8.3521 (3) Å
b = 7.7547 (2) Å
c = 15.1953 (5) Å
β = 104.447 (3)°
V = 953.05 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.18 mm⁻¹
T = 150 K
0.2 × 0.18 × 0.15 mm

Data collection

Agilent SuperNova Dual/Cu at zero/Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.792, T _max = 1.0
5287 measured reflections
2178 independent reflections
1867 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.072
S = 1.05
2178 reflections
126 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015747/bq2349sup1.cif

e-68-0m599-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015747/bq2349Isup2.hkl

e-68-0m599-Isup2.hkl^{(104.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O1	1.9816 (12)
Cu1—N11	2.0324 (14)
Cu1—O3A	2.4218 (13)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O3Aⁱ	0.93	2.46	3.105 (2)	127
C13—H13⋯O1ⁱⁱ	0.93	2.51	3.424 (2)	168
C14—H14⋯O2ⁱⁱⁱ	0.93	2.53	3.050 (2)	115
O3A—H3A⋯O2	0.82	1.79	2.595 (2)	169

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

Acknowledgments

The work was supported by the Slovenian Ministry of Education, Science, Culture and Sport through grant No. P1–0175. EN-FIST Centre of Excellence, Dunajska 156, 1000 Ljubljana, Slovenia is acknowledged for the use of the Supernova diffractometer.

supplementary crystallographic information

Comment

Simple pyridine alcohol ligands are commercially available substances which are of particular interest in coordination chemistry since they possess two functional groups, both capable to coordinate to metal centers. They can react as neutral ligands with a preserved alcohol function or as anionic (alkoxo) ligands with the OH group being deprotonated. The literature reports on some Cu^II species incorporating 2-(pyridin-2-yl)ethanol (2-pyEtOH) as a neutral ligand to copper atoms (i.e. Pothiraja et al., 2011; Yilmaz et al., 2003; Hamamci et al., 2004; Lah & Leban, 2010) and a series of Cu^II acetato compounds with 2-pyEtOH in its deprotonated form (Mobin et al., 2010). We report here the synthesis and crystal structure of new mononuclear Cu^II complex with 2-pyEtOH coordinated as a neutral ligand in a chelating manner using both functional groups. Cu atom is located on the inversion center and possesses a distorted octahedral environment with two O-atoms belonging to two acetato ligands, two O-atoms of the 2-pyEtOH side chains and two pyridine N atoms of the 2-pyEtOH ligands (Figure 1). An intramolecular hydrogen bond is observed between the hydroxy oxygen as a donor and the noncoordinated acetato oxygen as an acceptor. No classical intermolecular hydrogen-bond contacts were observed. However, crystal packing is effected by intermolecular C—H···O interactions involving aromatic C—H as donors and oxygen atoms of both ligands as acceptors. Thus, mononuclear units are linked into two-dimensional layers parallel to bc plane. See Table 2 for details.

Experimental

0,20 g of copper acetate hydrate was dissolved in 10,0 ml of methanol. 0,10 g of malonic acid and 0,10 ml of 2-(pyridin-2-yl)ethanol was added during intense stirring. The resulting blue solution was left at ambient condition to slowly evaporate the solvent. Within few days light blue crystals of the title compound appeared.