{2-[(5-Bromo-2-oxidobenzyl­idene)amino-κ2 N,O]-3-methyl­penta­noato-κO}(1,10-phenanthroline-κ2 N,N′)copper(II) dihydrate

Zheng Liu; Yong-Liao Wang; Yuan Wang

doi:10.1107/S1600536808009495

. 2008 May 3;64(Pt 6):m760. doi: 10.1107/S1600536808009495

{2-[(5-Bromo-2-oxidobenzylidene)amino-κ² N,O]-3-methylpentanoato-κO}(1,10-phenanthroline-κ² N,N′)copper(II) dihydrate

Zheng Liu ^a, Yong-Liao Wang ^a, Yuan Wang ^a,^*

PMCID: PMC2961405 PMID: 21202453

Abstract

In the title compound, [Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O, the Cu^II atom is pentacoordinated in a square-pyramidal geometry. The crystal packing is stabilized by O—H⋯O hydrogen bonds.

Related literature

For related literature, see: Feng et al. (2007 ▶); Li et al. (2006 ▶); Royles & Sherrington (2000 ▶); Jiang et al. (2003 ▶); Kettmann et al. (1993 ▶); Zhang (2006 ▶); Zhang et al. (2003 ▶).

Experimental

Crystal data

[Cu(C₁₃H₁₄BrNO₃)(C₁₂H₈N₂)]·2H₂O
M _r = 591.94
Monoclinic,
a = 10.6184 (18) Å
b = 6.0520 (16) Å
c = 19.777 (3) Å
β = 93.481 (2)°
V = 1268.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 298 (2) K
0.65 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.296, T _max = 0.846
6692 measured reflections
4255 independent reflections
2269 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.074
S = 0.96
4255 reflections
318 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 1785 Friedel pairs
Flack parameter: 0.054 (14)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009495/bt2691sup1.cif

e-64-0m760-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009495/bt2691Isup2.hkl

e-64-0m760-Isup2.hkl^{(208.5KB, 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
O5—H28⋯O1	0.85	2.06	2.904 (8)	174
O5—H29⋯O4	0.85	1.87	2.708 (10)	168
O4—H26⋯O5ⁱ	0.85	2.06	2.853 (8)	156
O4—H27⋯O2ⁱⁱ	0.85	2.02	2.746 (7)	143

Open in a new tab

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

Acknowledgments

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, China.

supplementary crystallographic information

Comment

Schiff base complexes play an important role in antibacterial and catalytic performance, and have attracted widespread interest by researchers (Jiang et al., 2003; Kettmann et al., 1993; Zhang, 2006). Meanwhile, Schiff base complexes containing isoleucine have been studied because they are of great significance in the biological and medical field (Royles et al., 2000; Feng et al., 2007; Li et al., 2006).

The central Cu^II atom is penta-coordinated (Fig.1). The quadratic planar is composed by O1, N2, O3and N1. The Schiff base forms two chelating rings(O1—C1—C2—N1—Cu1 and N1—C7—C8—C9—O3- Cu1) to the Cu^IIatom, with a diheral angle of 19.6 (4)° which is in the range observed for many copper Schiff base complexes. The N3 atom occupies the axial position with a N—Cu length of 2.229 (6) Å, comparing with the equatorial Cu—N bond lengths [Cu1—N1 1.924 (6)Å and N2—Cu1 1.975 (6)Å]. The crystal packing is stabilized by O—H···O hydrogen bonds (Fig. 2).

Experimental

5-Bromo-2-hydroxy-benzaldehyde(0.5 mmol, 100.5 mg) was dissolved in hot ethanol(5 ml), then a mixture of D,L-isoleucine (0.5 mmol, 65.6 mg) and sodium hydroxide (1.0 mmol, 40 mg) was added. After stirring for 1 h, the copper dinitrate trihydrate(0.5 mmol, 120.8 mg) was added and refluxed for another 2 h. At last, an ethanol solution of Phen(0.5 mmol, 99.1 mg) was dropped gradually into to the reaction mixture and refluxed for further 3 h (Zhang et al., 2003; Zhang et al., 2006). The obtained green solution was filtered and held at room temperature for ten days, whereupon green crystals suitable for X-ray diffraction were obtained (yield: 45.2%, based on Cu).