Aqua­(2-oxido-2,2-diphenyl­acetato-κ2 O 1,O 2)(1,10-phenanthroline-κ2 N,N′)copper(II)

Xiao-Xia Yang; Fu-Yong Zhang; Shi-Hai Xu

doi:10.1107/S1600536809053483

. 2009 Dec 16;66(Pt 1):m69. doi: 10.1107/S1600536809053483

Aqua(2-oxido-2,2-diphenylacetato-κ² O ¹,O ²)(1,10-phenanthroline-κ² N,N′)copper(II)

Xiao-Xia Yang ^a, Fu-Yong Zhang ^a, Shi-Hai Xu ^a,^*

PMCID: PMC2980168 PMID: 21579963

Abstract

In the title mononuclear complex, [Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)], the Cu^II atom is five-coordinated by two N atoms from a 1,10-phenanthroline (phen) ligand, two O atoms from a benzilate ligand and one O atom from a water molecule in a distorted square-pyramidal geometry. The crystal structure is stabilized via intermolecular O—H⋯O and C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π stacking interactions between the pyridine and benzene rings of neighboring phen ligands [centroid–centroid distances = 3.684 (2), 3.564 (2) and 3.380 (1) Å].

Related literature

For related structures of benzilate compounds, see: Mora et al. (2003 ▶); Rojas et al. (2003 ▶).

Experimental

Crystal data

[Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)]
M _r = 487.98
Triclinic,
a = 7.4473 (15) Å
b = 9.757 (2) Å
c = 15.319 (3) Å
α = 102.99 (3)°
β = 98.39 (3)°
γ = 96.70 (3)°
V = 1060.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.07 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.740, T _max = 0.807
8229 measured reflections
3802 independent reflections
2607 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.229
S = 1.09
3802 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −1.54 e Å⁻³

Data collection: CrystalStructure (Rigaku/MSC, 2002 ▶); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053483/hy2263sup1.cif

e-66-00m69-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053483/hy2263Isup2.hkl

e-66-00m69-Isup2.hkl^{(186.4KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O2	1.949 (4)
Cu1—O3	1.853 (4)
Cu1—N1	2.014 (4)
Cu1—N2	2.019 (5)
Cu1—O1W	2.476 (5)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2ⁱ	0.82	2.07	2.883 (6)	171
O1W—H2W⋯O1ⁱⁱ	0.83	2.13	2.954 (4)	175
C17—H17⋯O1ⁱⁱⁱ	0.93	2.41	3.312 (8)	162
C21—H21⋯Cg1ⁱ	0.93	2.46	3.267 (8)	146

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C9–C14 ring.

Acknowledgments

The authors kindly acknowledge the 863 Program of China (2006 A A09Z408) and the National Natural Science Foundation of China (20772048) for supporting this work.

supplementary crystallographic information

Comment

In the structural investigations of benzilate complexes, it has been found that the benzilic acid functions as a multidentate ligand with versatile binding and coordination modes (Mora et al., 2003; Rojas et al., 2003). In this paper, we report the structure of the title compound, a copper(II) complex obtained by the reaction of benzilic acid, 1,10-phenanthroline (phen) and copper chloride in an alkaline aqueous solution.

As depicted in Fig. 1, the Cu^II atom exists in a square-pyramidal environment, defined by two O atoms from one benzilate ligand, two N atoms from one phen ligand and one water molecule. The crystal structure is stabilized via intermolecular O—H···O and C—H···O hydrogen bonds, C—H···π interactions (Table 1) and π–π stacking interactions between the pyridine and benzene rings of neighboring phen ligands (Fig. 2), with the centroid–centroid distances of Cg2···Cg3ⁱ = 3.684 (2), Cg3···Cg4ⁱ = 3.564 (2) and Cg4···Cg4ⁱⁱ = 3.380 (1) Å [Cg2, Cg3 and Cg4 are the centroids of the N1, C15, C16, C17, C23, C25 ring, the N2, C20, C21, C22, C24, C26 ring and the C18, C19, C23, C24, C25, C26 ring, respectively. Symmetry codes: (i) -x, -y, -z; (ii) -1-x, -y, -z].

Experimental

A mixture of copper chloride (0.134 g, 1 mmol), benzilic acid (0.228 g, 1 mmol), phen (0.18 g, 1 mmol), NaOH (0.06 g, 1.5 mmol), EtOH (6 ml) and H₂O (6 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 358 K for 8 h and then cooled to room temperature at a rate of 10 K h^-1. The blue crystals obtained were washed with water and dried in air.