Diaqua­bis­[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ato]copper(II) bis[4-(4-carboxyphenoxy)benzoate]

Dian-Zhen Sun; Guang-Ju Zhang; Hai-Yan Chen; Jiang-Hong He; Shi-Wei Yan

doi:10.1107/S1600536811006672

. 2011 Feb 26;67(Pt 3):m388. doi: 10.1107/S1600536811006672

Diaquabis[8-ethyl-5-oxo-2-(piperazin-4-ium-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]copper(II) bis[4-(4-carboxyphenoxy)benzoate]

Dian-Zhen Sun ^a,^*, Guang-Ju Zhang ^a, Hai-Yan Chen ^a, Jiang-Hong He ^a, Shi-Wei Yan ^a

PMCID: PMC3052055 PMID: 21522306

Abstract

In the title compound, [Cu(C₁₄H₁₇N₅O₃)₂(H₂O)₂](C₁₄H₉O₅)₂, the Cu²⁺ atom, located on an inversion centre, exhibits a distorted octahedral geometry, coordinated by four O atoms from two pipemidic acid ligands in equatorial positions and two water molecules in axial positions. The pipemidic acid ligand acts a bidentate ligand and the single deprotonated 4,4′-oxydibenzoic acid acts as an anion. Classical N—H⋯O and O—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For general background to the use of quinolones in the treatment of infections, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

[Cu(C₁₄H₁₇N₅O₃)₂(H₂O)₂](C₁₄H₉O₅)₂
M _r = 1220.66
Triclinic,
a = 8.611 (8) Å
b = 12.555 (12) Å
c = 13.436 (12) Å
α = 76.222 (10)°
β = 73.299 (10)°
γ = 81.015 (10)°
V = 1345 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 295 K
0.47 × 0.41 × 0.33 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.801, T _max = 0.854
11977 measured reflections
5790 independent reflections
4801 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.140
S = 1.04
5790 reflections
397 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006672/rk2260sup1.cif

e-67-0m388-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006672/rk2260Isup2.hkl

e-67-0m388-Isup2.hkl^{(283.4KB, 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
OW1—HW1A⋯O4ⁱ	0.85 (1)	2.08 (1)	2.921 (3)	169 (2)
OW1—HW1B⋯O7ⁱⁱ	0.85 (1)	2.08 (3)	2.892 (3)	161 (2)
O6—H6A⋯O5ⁱⁱⁱ	0.81 (3)	1.81 (3)	2.582 (3)	160 (3)
N1—H1A⋯O1ⁱⁱ	0.90	1.91	2.783 (3)	162
N1—H1B⋯O4^iv	0.90	1.73	2.604 (3)	164

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

Acknowledgments

This work was supported by the Science and Technology Foundation of Southwest University (SWUB2007035).

supplementary crystallographic information

Comment

Pipemidic acid (Hppa, C₁₄H₁₇N₅O₃, 8-ethyl-5,8-dihydro-5- oxo-2-(1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). H₂oba (4,4'-oxybisbenzoic acid) acts a anion in this complex. The metal complexes of the Hppa and H₂oba have not been reported till; the title copper(II) complex, I, is presented here (Fig. 1).

The Cu atom exhibits an approximate square environment with atoms O2, O3, O2ⁱ, O3ⁱ (see Fig. 1 for symmetry code) of two Hppa ligands (two O, O-bidentate). The Cu—O bond distances arising from the two carbonyl oxygen atoms O3 are longer (1.9605 (19)Å) than those arising from the carboxylate oxygen atoms O2 (1.932 (2)Å). The bond angles O2—Cu1—O3ⁱ and O2—Cu1—O3 open up slightly from 88.51 (9)° to 91.49 (9)°. The Cu^II atom at each short edge of the rectangle are bridged by an water molecule, which also interacts weakly (Cu1···OW1 = 2.642 (10)Å) with the central metal, resulting in a distortion octahedral geometry. Classical N—H···O and O—H···O hydrogen bonds are present in the crystal structure (Table 1).

Experimental

A mixture of CuI (0.095 g, 0.5 mmol), Hppa (0.089 g, 0.25 mmol), H₂oba (0.0645 g, 0.25 mmol) and water (8 ml) was stirred for 30 min in air. The mixture was then transferred to a 18 ml teflon-lined hydrothermal bomb. The bomb was kept at 393 K for 120 h under autogenous pressure. Upon cooling, blue block of I were obtained from the reaction mixture.