Bis{4-bromo-2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}nickel(II) monohydrate

Chen-Yi Wang; Jing-Fen Li; Ping Wang; Cai-Jun Yuan

doi:10.1107/S1600536811031771

. 2011 Aug 11;67(Pt 9):m1227–m1228. doi: 10.1107/S1600536811031771

Bis{4-bromo-2-[(2-hydroxyethyl)iminomethyl]phenolato}nickel(II) monohydrate

Chen-Yi Wang ^a,^*, Jing-Fen Li ^a, Ping Wang ^b, Cai-Jun Yuan ^a

PMCID: PMC3200792 PMID: 22058854

Abstract

The title mononuclear nickel complex, [Ni(C₉H₉BrNO₂)₂]·H₂O, was obtained by the reaction of 5-bromosalicylaldehyde, 2-aminoethanol and nickel nitrate in methanol. The Ni^II atom is six-coordinated by two phenolate O, two imine N and two hydroxy O atoms from two crystallographically different Schiff base ligands, forming an octahedral geometry. In the crystal, molecules are linked by intermolecular O—H⋯O and O—H⋯Br hydrogen bonds, forming a three-dimensional network.

Related literature

For urease inhibitors, see: Wang (2009 ▶); Wang & Ye (2011 ▶). For related nickel(II) complexes, see: Arıcı et al. (2005 ▶); Liu et al. (2006 ▶); Li & Wang (2007 ▶); Ali et al. (2006 ▶).

Experimental

Crystal data

[Ni(C₉H₉BrNO₂)₂]·H₂O
M _r = 562.89
Orthorhombic,
a = 9.835 (3) Å
b = 12.851 (2) Å
c = 16.226 (3) Å
V = 2050.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 4.87 mm⁻¹
T = 298 K
0.21 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.428, T _max = 0.442
13318 measured reflections
4474 independent reflections
2310 reflections with I > 2σ(I)
R _int = 0.099

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.128
S = 1.02
4474 reflections
259 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.95 e Å⁻³
Absolute structure: Flack (1983 ▶), 1930 Friedel pairs
Flack parameter: 0.013 (19)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811031771/ci5196sup1.cif

e-67-m1227-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031771/ci5196Isup2.hkl

e-67-m1227-Isup2.hkl^{(219.2KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni1—N1	1.976 (7)
Ni1—N2	1.981 (7)
Ni1—O1	2.008 (6)
Ni1—O3	2.014 (6)
Ni1—O2	2.132 (5)
Ni1—O4	2.160 (6)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O1	0.85 (1)	2.22 (7)	2.898 (8)	136 (8)
O5—H5A⋯Br2ⁱ	0.85 (1)	2.92 (5)	3.666 (9)	146 (8)
O4—H4A⋯Br1ⁱⁱ	0.93	2.90	3.532 (6)	126
O4—H4A⋯O5ⁱ	0.93	2.16	2.841 (9)	130
O2—H2A⋯O3ⁱⁱⁱ	0.93	1.97	2.694 (7)	133

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

Acknowledgments

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Natural Science Foundation of Zhejiang Province (No. Y407318) and the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060).

supplementary crystallographic information

Comment

As part of our investigations into novel urease inhibitors (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear nickel(II) complex, Fig. 1. The compound contains a mononuclear nickel(II) complex molecule and a water molecule of crystallization. The Ni atom in the complex is six-coordinated by two phenolate O, two imine N, and two hydroxy O atoms from two Schiff base ligands, forming an octahedral geometry. The trans angles at the Ni atom are in the range 173.1 (3)–174.0 (2)°; the other angles are close to 90°, ranging from 80.4 (3) to 94.8 (2)°, indicating a slightly distorted octahedral coordination. The Ni—O and Ni—N bond lengths (Table 1) are typical and are comparable to those observed in other similar nickel(II) complexes (Arıcı et al., 2005; Liu et al., 2006; Li & Wang, 2007; Ali et al., 2006).

In the crystal structure of the compound, molecules are linked through intermolecular O—H···O and O—H···Br hydrogen bonds (Table 2), to form a three-dimensional network (Fig. 2).

Experimental

5-Bromosalicylaldehyde (1.0 mmol, 0.201 g), 2-aminoethanol (1.0 mmol, 0.061 g), and nickel nitrate hexahydrate (0.5 mmol, 0.146 g) were dissolved in MeOH (30 ml). The mixture was stirred at room temperature for 10 min to give a clear green solution. After keeping the solution in air for a week, green block-shaped crystals were formed at the bottom of the vessel.