(2-Hy­droxy­acetato-κO 1)bis­(1,10-phenan­throline-κ2 N,N′)copper(II) nitrate

Ya-Jie Kong; Zhuang-Dong Yuan

doi:10.1107/S1600536811013110

. 2011 Apr 13;67(Pt 5):m592. doi: 10.1107/S1600536811013110

(2-Hydroxyacetato-κO ¹)bis(1,10-phenanthroline-κ² N,N′)copper(II) nitrate

Ya-Jie Kong ^a,^*, Zhuang-Dong Yuan ^a

PMCID: PMC3089357 PMID: 21754313

Abstract

In the title compound, [Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃, the Cu^II atom is coordinated by two phenanthroline (phen) ligands and one carboxyl-O atom of a hydroxyacetate anion in a distorted square-pyramidal geometry. The hydroxy group of the hydroxyacetate ligand links with the counter NO₃ ⁻ anion via a pair of bifurcated O—H⋯O hydrogen bonds. The centroid–centroid distance of 3.5676 (14) Å between benzene rings of parallel phen ligands of adjacent molecules suggests the existence of π–π stacking. Weak intermolecular C—H⋯O hydrogen bonding is also present in the crystal structure.

Related literature

For related structures, see: Carballo et al. (2001 ▶).

Experimental

Crystal data

[Cu(C₂H₃O₃)(C₁₂H₈N₂)₂]NO₃
M _r = 561.00
Monoclinic,
a = 21.718 (4) Å
b = 14.347 (3) Å
c = 16.311 (3) Å
β = 117.045 (3)°
V = 4526.5 (16) Å³
Z = 8
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 293 K
0.50 × 0.40 × 0.40 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.599, T _max = 0.664
17009 measured reflections
4425 independent reflections
4047 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.101
S = 1.06
4425 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 global, I. DOI: 10.1107/S1600536811013110/xu5175sup1.cif

e-67-0m592-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013110/xu5175Isup2.hkl

e-67-0m592-Isup2.hkl^{(216.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O4	1.9511 (15)
Cu1—N1	2.0109 (16)
Cu1—N2	2.2298 (16)
Cu1—N3	2.0037 (16)
Cu1—N4	2.0449 (15)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1	0.82	2.15	2.963 (3)	168
O6—H6A⋯O3	0.82	2.49	3.135 (4)	137
C7—H7A⋯O3ⁱ	0.93	2.42	3.351 (3)	176
C16—H16A⋯O1ⁱⁱ	0.93	2.53	3.383 (4)	152
C18—H18A⋯O3ⁱⁱⁱ	0.93	2.53	3.456 (4)	172
C26—H26A⋯O6^iv	0.97	2.44	3.297 (3)	147

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

Acknowledgments

This work was supported by the Science Foundation of Jining University, China.

supplementary crystallographic information

Comment

The molecules [Cu(C₁₂H₈N₂)₂(C₂H₃O₃)] in three different solvents or anions(2-hydroxyacetate anion, 2-hydroxyacetic acid and acetonitrile solvent) have been reported (Carballo et al., 2001).

Crystals [Cu(C₁₂H₈N₂)₂(C₂H₃O₃)]NO₃ (I) were obtained by crystallized from ethanol-water solution. The molecular structure of (I) is shown in Fig. 1. In the title compound the Cu^II atom is coordinated by two phenanthroline (phen) ligands and one carboxyl-O atom of a hydroxyacetate anion in a distorted square-pyramidal geometry (Table 1). The hydroxy group of the hydroxyacetate ligand links with the counter NO₃^- anion via a pair of bifurcated O—H···O hydrogen bonds (Table 2). The centroid-to-centroid distance of 3.5676 (14) Å between benzene rings of parallel phen ligands of adjacent molecules suggests the existence of π-π stacking. Weak intermolecular C—H···O hydrogen bonding is also present in the crystal structure.

Experimental

Copper nitrate (0.093 g, 0.5 mmol) was added to a mixed solution of hydroxyacetic acid (0.076 g, 1 mmol) in distilled water (10 ml) and 1,10-phenanthroline (0.090 g, 0.5 mmol) in ethanol (5 ml). The pH value of the mixture was adjusted to 7 with ammonia. The resulting solution was stirred for 1 h, and then filtered off. The filtrate was left to evaporate showly at room temperature. After a long time, blue block crystals were obtained.