Aqua­bis(dichloro­acetato-κO)(1,10-phenanthroline-κ2 N,N′)copper(II)

Yaru Liu; Jianzhong Ning; Junshan Sun; Chuan Zhang

doi:10.1107/S1600536808042578

. 2008 Dec 20;65(Pt 1):m113. doi: 10.1107/S1600536808042578

Aquabis(dichloroacetato-κO)(1,10-phenanthroline-κ² N,N′)copper(II)

Yaru Liu ^a, Jianzhong Ning ^b, Junshan Sun ^c,^*, Chuan Zhang ^c

PMCID: PMC2968015 PMID: 21581478

Abstract

In the title complex, [Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)], the Cu^II ion has a distorted square-pyramidal coordination geometry. The equatorial positions are occupied by two N atoms from a 1,10-phenanthroline ligand [Cu—N = 1.994 (3) and 2.027 (3) Å] and two O atoms from dichloroacetate ligands and a water molecule [Cu—O = 1.971 (2) and 1.939 (2) Å]. One O atom from another dichloroacetate ligand occupies the apical positon [Cu—O = 2.152 (3) Å]. Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing also exhibits weak intermolecular C—H⋯O hydrogen bonds, π–π interactions [centroid–centroid distance = 3.734 (2) Å] and short intermolecular Cl⋯Cl contacts [3.306 (2) and 3.278 (2) Å].

Related literature

For applications of dichloroacetic acid derivatives, see: Múdra et al. (2003 ▶); Lin et al. (2001 ▶); Zhu & Xiao (2006 ▶).

Experimental

Crystal data

[Cu(C₂HCl₂O₂)₂(C₁₂H₈N₂)(H₂O)]
M _r = 517.62
Triclinic,
a = 8.2701 (8) Å
b = 10.8883 (11) Å
c = 12.0125 (12) Å
α = 67.4390 (10)°
β = 77.585 (2)°
γ = 73.776 (2)°
V = 952.02 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 273 (2) K
0.32 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.606, T _max = 0.711
5043 measured reflections
3346 independent reflections
2539 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.106
S = 1.01
3346 reflections
261 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.51 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 I, global. DOI: 10.1107/S1600536808042578/cv2493sup1.cif

e-65-0m113-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042578/cv2493Isup2.hkl

e-65-0m113-Isup2.hkl^{(164.1KB, 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—H16⋯O2ⁱ	0.98	2.24	3.118 (5)	149
O5—H5B⋯O2ⁱⁱ	0.85 (2)	1.81 (2)	2.654 (3)	174 (3)
O5—H5A⋯O4	0.85 (2)	1.86 (2)	2.673 (4)	159 (3)

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

Acknowledgments

The authors thank the Postgraduate Foundation of Taishan University for financial support (grant No. Y07–2–15).

supplementary crystallographic information

Comment

Dichloroacetic acid and its derivatives are biologically active compounds which have been widely studied because of their fascinating topologies and potential applications as functional materials (Múdra et al., 2003; Lin et al., 2001; Zhu et al., 2006;). In our study of this field, we selected 1,10-phenanthroline as the co-ligand to continue our exploration to the Cu complexes with the dichloroacetic acid ligand. Herein we report the structure of the title complex (I).

In (I) (Fig. 1), the Cu ion has a distorted square-pyramidal coordination. Two N atoms from 1,10-phenanthroline ligand and two oxygen atoms from a dichloroacetic acid ligand form a basal plane, and an aqua atom occupy the axial apical position. Intermolecular O—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds, π–π interactions and short intermolecular Cl···Cl contacts (Table 1).

Experimental

A mixture of Cu(CH3COO)2*3H2O(204 mg, 1 mmol) and 1,10-phenanthroline (185 mg, 1 mmol) in methanol(30 ml) was placed in a Teflon-lined stainless steel Parr bomb that was heated at 403 K for 48 h. The bomb was then cooled down to the room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum, and the solid residue was recrystallized from diethyl ether; blue crystals suitable for X-Ray diffraction study were obtained. Yield, 0.760 g, 83%. m.p. 573 K. Analysis, calculated for C₁₆H₁₂Cl₄CuN₂O₅: C 46.73, H 2.94, N 6.81; found: C 46.95, H 2.56, N 7.07%. The elemental analyses were performed with a Perkine Elemer PE2400II instrument.