One-dimensional chain copper(II) and nickel(II) coordination polymers with N-salicylideneglycine schiff base ligand

Article abstract of DOI:10.1080/15533174.2012.680127

[Cu(Sal-Gly)(Im)(H₂O)] (1) and [Ni(Sal-Gly)(H₂O) ₂] (2) (Sal- Gly = N-salicylideneglycinate) was synthesized and structurally characterized. 1 and 2 are one-dimensional chain coordination polymers. In 1, Cu(II) ion has a five-coordinated square-pyramidal geometry and is surrounded by two O and one N atoms from a tetradentate Sal-Gly dianion and one N atom from imidazole ligand and one O from adjacent Sal-Gly ligand. In 2, Ni(II) adopts six-coordinated distorted octahedral geometry and is surrounded by two O and one N atoms from a tetradentate Sal-Gly dianion, two O from two aqua ligands, and one O from adjacent Sal-Gly ligand.

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One-Dimensional Chain Copper(II) and Nickel(II)
Coordination Polymers With N-Salicylideneglycine
Schiff Base Ligand
Shao-Ming Shi a , Yun-Qiong Gu a , Zhen-Feng Chen a , Yan-Cheng Liu a & Hong Liang a
a Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources
(Ministry of Education of China), School of Chemistry and Chemical Engineering, Guangxi
Normal University, Guilin, P. R. China
Accepted author version posted online: 06 Jul 2012.Published online: 01 Oct 2012.
To cite this article: Shao-Ming Shi , Yun-Qiong Gu , Zhen-Feng Chen , Yan-Cheng Liu & Hong Liang (2012): One-Dimensional
Chain Copper(II) and Nickel(II) Coordination Polymers With N-Salicylideneglycine Schiff Base Ligand, Synthesis and Reactivity
in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42:9, 1262-1266
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 42:1262–1266, 2012
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2012.680127
One-Dimensional Chain Copper(II) and Nickel(II)
Coordination Polymers With N-Salicylideneglycine Schiff
Base Ligand
Shao-Ming Shi, Yun-Qiong Gu, Zhen-Feng Chen, Yan-Cheng Liu,
and Hong Liang
Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources
(Ministry of Education of China), School of Chemistry and Chemical Engineering,
Guangxi Normal University, Guilin, P. R. China
acid Schiff base complexes have been investigated for their
important biological properties including antibacterial activ-
ity,[12−13] scavenging effect on O2,[14−16] and anticancer ac-
tivity.[12] These results stimulated our research interest on the
N-salicylideneglycinato-metal complexes. Although a series
of N-salicylideneglycinato-metal complexes have been syn-
thesized and characterized, such as nickel(II), copper(II), and
zinc(II),[17−24] as well as oxovanadium(V) complexes,[25,26] the
polymeric structures assembled by N-salicylideneglycine Schiff
base and metal salts are rarely reported. Herein, we report the
synthesis, crystal structure one-dimensional zigzag chain co-
ordination polymers: [Cu(Sal-Gly)(Im)(H2O)] (1) and [Ni(Sal-
Gly)(H2O)2] (2) (Sal-Gly = N-salicylideneglycinate), which
may enrich the supramolecular chemistry of Schiff base.
[Cu(Sal-Gly)(Im)(H2O)] (1) and [Ni(Sal-Gly)(H2O)2] (2) (Sal-
Gly = N-salicylideneglycinate) was synthesized and structurally
characterized. 1 and 2 are one-dimensional chain coordination
polymers. In 1, Cu(II) ion has a five-coordinated square-pyramidal
geometry and is surrounded by two O and one N atoms from a
tetradentate Sal-Gly dianion and one N atom from imidazole lig-
and and one O from adjacent Sal-Gly ligand. In 2, Ni(II) adopts
six-coordinated distorted octahedral geometry and is surrounded
by two O and one N atoms from a tetradentate Sal-Gly dianion,
two O from two aqua ligands, and one O from adjacent Sal-Gly
ligand.
Keywords amino acid Schiff base, copper(II), crystal structure,
nickel(II)
INTRODUCTION
EXPERIMENTAL
The Schiff base transition metal complexes of amino acid
have been the subject of considerable research because these
complexes exhibit potential anticarcinogenic, antivirus, an-
tibacterial, and antipyretic activities.[1–3] Recently, several re-
views have focused on the supramolecular chemistry of Schiff
base ligands.[4–9] Taking advantage of Schiff base to construct
supramolecular structures have been attracted many chemists’
interest. N-salicylideneglycinato-metal complexes are consid-
ered as the valuable nonenzymatic models of the action of Vi-
tamin B6 enzyme.[10,11] In addition, a large number of amino
Materials
All chemicals were purchased from commercial sources and
used without further purification. N-salicylideneglycine Schiff
base were prepared by literature method.[27]
Physical Measurements
C, H, and N data were obtained using Perkin-Elmer 2400II
CHNS/O elemental analyzer (Waltham, MA, USA). Infrared
spectra were measured on a Nicolet FT-IR spectrophotome-
ter (Madison, WI, USA) with KBr pellets in the range
4000–400 cm−1. X-ray single crystal structural analyses were
performed on a Bruker CCD area detector diffractometer (Ger-
many) with graphite-monochromatized Mokα radiation.
Received 15 August 2011; accepted 24 December 2011.
This work was supported by the National Basic Research Program
of China (Nos. 2009CB526503 and 2010CB534911), the National Nat-
ural Science Foundation of China (No. 20861002), and the Natural
Science Foundation of Guangxi Province (Nos. 0991012Z, 0991003,
2010GXNSFF013001).
Address correspondence to Zhen-Feng Chen, Key Laboratory for
the Chemistry and Molecular Engineering of Medicinal Resources
(Ministry of Education of China), School of Chemistry and Chem-
ical Engineering, Guangxi Normal University, Guilin 541004, P. R.
China. E-mail: chenzfgxnu@yahoo.com
Synthesis of [Cu(Sal-Gly)(Im)] (1)
To a solution of Cu(CH3COO)2·H2O (0.200 g, 1 mmol) in
95% ethanol (20 mL) was added to N-salicylideneglycine Schiff
base(Sal-Gly) (0.179 g, 1 mmol) and imidazole (Im) (0.068 g,
1 mmol) in 95% ethanol (20 mL). The mixture was stirred at
60–70◦C for 5 h. The precipitates was collected by filtration,
washed successively with water and ethanol, and dried in air.
1262

SCHIFF BASE SUPRAMOLECULAR CHEMISTRY
1263
TABLE 1
Crystallographic data and refinement details for 1 and 2
1
2
Formula
Formula weight
Crystal system
Space group
a (Å)
C12H11CuN3O3
308.78
monoclinic
P2(1)/c
11.057(4)
11.509(5)
9.676(4)
103.141(4)
1199.1(8)
4
C18H22N2Ni2O10
543.80
monoclinic
P2(1)/c
15.369(2)
7.4345(11)
9.1435(13)
106.532(3)
1001.6(3)
2
b (Å)
c (Å)
β (◦)
V (Å3)
Z
Dc (g/cm3))
1.710
1.828
1.803
1.942
µ (mm−1
)
Crystal size (mm3) 0.31 × 0.27 × 0.15 0.28 × 0.24 × 0.22
F(000)
628
560
R1 [I > 2σ(I)
wR2 (all data)
0.0334
0.0908
0.0291
0.0836
FIG. 1. ORTEP view of 1 with 30% thermal ellipsoids showing the atom-
labeling around copper(II). Symmetry transformations used to generate equiv-
alent atoms, A: x, 1.5 − y, 0.5 + z (color figure available online).
Then, a portion of precipitate was dissolved in aqueous ethanol
(H2O:CH3CH2OH = 1:2, 30 mL), and it was maintained at
ambient temperature for slow evaporation. After seven days, a
dark-green block crystals of 1 suitable for X-ray diffraction anal-
ysis were isolated in 30% yield. Anal. Calcd. for C12H11CuN3O3
(%): C, 46.68; H, 3.59; N, 13.61. Found (%): C, 46.52; H, 3.60;
N, 13.70. Main IR (KBr, cm−1): 3025(w), 1642(s), 1576(s),
1453(ms), 1383(ms), 760(w), 657(w), 533(w).
X-Ray Studies
The crystals of 1 and 2 were selected and mounted on a glass
fiber in air. The diffraction data were collected on a Bruker CCD
diffractometer (Germany) equipped with graphite monochro-
ꢁ
mated Mo-Kα radiation (λ = 0.71073Å, 50 kV, 150 mA) using
the ꢀ-ω scan mode at room temperature. Raw frame data were
integrated with the SAINT program (University of Go¨ttingen,
Go¨ttingen, Germany).[28] The structures were solved by direct
methods using SHELXS-97 and refined by full-matrix least
squares using SHELXL-97 (Bruker AXS Inc., Madison, WI,
USA).[29] An empirical absorption correction was applied with
SADABS (University of Go¨ttingen, Go¨ttingen, Germany).[30]
All non-hydrogen atoms were refined anisotropically and hydro-
gen atoms were located in the calculated positions and refined by
a riding mode, with a common thermal parameter. The drawings
were made with XP and Diamond, and all calculations were per-
formed on a PC computer with SHELXTL (Bruker AXS Inc.,
Synthesis of [Ni(Sal-Gly)(H2O)2] (2)
This complex was prepared in a similar process as for 1.
Ni(CH3COO)2·4H2O was used to replace Cu(CH3COO)2·H2O,
but without imidazole. A bright green block crystals of 2 suitable
for X-ray diffraction analysis was obtained in 40% yield. Anal.
Calcd. for C18H22N2Ni2O10 (%): C, 39.76; H, 4.08; N, 5.15.
Found (%): C, 39.61; H, 4.12; N, 5.06. Main IR (KBr, cm−1):
3369(m), 1657(s), 1599(s), 1476(ms), 1297(ms), 1195.1(m),
748(m), 523(w).
TABLE 2
ꢁ
Selected bond length (Å) and angles (◦) for 1
Cu(1)−O(1)
1.989 (2)
1.918 (2)
2.5260 (7)
83.39 (9)
171.50 (9)
97.75 (9)
Cu(1)−N (1)
1.927 (2)
1.958 (2)
Cu(1)−O(2)
Cu(1)−N(2)
Cu(1)−O(2A)
O(1)−Cu(1)−N(1)
O(1)−Cu(1)−O(3)
O(3)−Cu(1)−N(1)
O(1)−Cu(1)−N(2)
N(1)−Cu(1)−N(2)
O(3)−Cu(1)−N(2)
92.47 (9)
172.69 (10)
90.53 (9)
Symmetry transformations used to generate equivalent atoms, A: x, 1.5 − y, 0.5 + z.

1264
S.-M. SHI ET AL.
FIG. 2. One-dimensional zigzag chain with polyhedron geometry around copper(II) centers. For clarity, H atoms were omitted (color figure available online).
Madison, WI, USA).[29] The crystal data, data collection and
refinement details are summarized in Table 1.
(Cu(1)−O(1) 1.989(2), Cu(1)−O(2) 1.918(2), Cu(1)−N(1)
ꢁ
1.9313(18), and Cu(1)−N(2) 1.9619(18) Å ), which are
well comparable with those found for the Cu(II) complexes
derived from salicyladehyde and amino acid—(imidazole)
RESULTS AND DISCUSSION
(N-salicylidene-beta-alaninato)copper(II),[35] [Cu(Sal-Ser)(2-
amino pyridine)][36]—while a weakly coordinated O(2A) from
Synthesis and Characterization of the Complexes
an adjacent complex unit is located on the apical site with
Reactions of Sal-Gly with Cu(II) (at presence of imidazole)
and Ni(II) salts gave complexes 1 and 2. The IR spectra provided
valuable information regarding the nature of functional groups
present in the ligands and their metal complexes. The strong
peaks at 1612 cm−1 attributed to C N stretching vibration band
of Sal-Gly ligand are shifted to low frequency in complexes
1 and 2 (1576 and 1599 cm−1), which indicate that the nitro-
gen of the imine group is coordinated to the metal ions.[31–33]
The broad bands in the range 3050–3075 cm−1 ascribed to in-
tramolecular H-bonded –OH groups of Sal-Gly ligand,[34] which
are not present in complexes 1 and 2, indicating that the oxygen
of the –OH groups are coordinated to the metal ions.[31] The
characteristic stretching vibrations of free carboxyl group (Sal-
Gly) at 1730 cm−1 are split into two peaks: 1647 [υas(COO−)]
and 1453 cm−1 [υs(COO−)] for 1 with ꢁυ = 194 cm−1; 1657
and 1476 cm−1 for 2 with ꢁυ = 181 cm−1. The splitting of
υas(COO−) and υs(COO−) indicates that the oxygen of car-
boxylate of Sal-Gly is coordinated to the metal ion.
ꢁ
Cu−O(2A) distance of 2.5260(7) Å. In addition, The Cu(1)−O
bond length to phenolic oxygen O(1) of the tridentate Schiff base
is significantly shorter than the bonding to carboxylic oxygen
O(2), which indicates different bond strengths.[35] By means of
the bidentate bridge COO− of Sal-Gly, the adjacent copper(II)
atoms are linked, resulting in a one-dimensional zigzag chain
(Figure 2). It should be pointed out that the hydrogen bond
between the imidazole and O(2) also attributable to the zigzag
conformation.
Structural of [Cu(Sal-Gly)(Im)] (1)
The molecular structure of [Cu(Sal-Gly)(Im)] (1) with
the atom-numbering scheme is illustrated in Figure 1 and
selected bond distances and angles are listed in Table 2.
As shown in Figure 1, the central metal atom Cu1 coor-
dinates by three oxygens and one N from two tetraden-
tate Schiff base (Sal-Gly) and one nitrogen from imida-
zole, thus forms a square-pyramidal geometry, which is sim-
ilar to (imidazole)(N-salicylidene-beta-alaninato)copper(II),[35]
[Cu(Sal-Ser)(2-amino pyridine)] (Sal-Ser = N-salicylidene-L-
serinate).[36] The N(1), O(1), O(3), N(2) composes of the bot-
tom plane of the square-pyramid with common bond distances
FIG. 3. ORTEP view of 2 with 30% thermal ellipsoids showing the atom-
labeling around nickel(II). Symmetry transformations used to generate equiva-
lent atoms, A: x, 0.5 − y, −0.5 + z (color figure available online).

SCHIFF BASE SUPRAMOLECULAR CHEMISTRY
1265
TABLE 3
ꢁ
Selected bond length (Å) and angles (◦) for 2
Ni(1)−N(1)
1.994 (2)
2.1294 (19)
2.1030 (19)
89.13 (9)
80.22 (9)
91.92 (9)
96.26 (8)
98.63 (8)
83.70 (7)
85.21 (7)
Ni(1)−O(1W)
2.027 (2)
2.0209 (19)
2.1384 (19)
168.57 (7)
92.81 (9)
85.81 (8)
84.87 (8)
92.76 (8)
100.18 (8)
164.27 (8)
Ni(1)−O(3A)
Ni(1)−O(1)
Ni(1)−O(2)
Ni(1)−O(W)
N(1)−Ni(1)−O(1)
N(1)−Ni(1)−O(2)
N(1)−Ni(1)−O(1W)
N(1)−Ni(1)−O(2W)
O(1W)−Ni(1)−O(2)
O(2)−Ni(1)−O(3)
O(2)−Ni(1)−O(2W)
O(1)−Ni(1)−O(2)
N(1)−Ni(1)−O(3)
O(1W)−Ni(1)−O(3)
O(1W)−Ni(1)−O(2W)
O(1)−Ni(1)−O(3)
O(1)−Ni(1)−O(2W)
O(3)−Ni(1)−O(2W)
Symmetry transformations used to generate equivalent atoms, A: x, 0.5 – y, –0.5 + z.
TABLE 4
Hydrogen bonds for 2
D−H
H···A
D···A
∠(DHA)(◦)
O(1W)−H(1WA)···O(3)#3
O(1W)−H(1WB)···O(2W)#4
O(2W)−H(2WB)···O(2)#3
O(2W)−H(2WA)···O(1)#5
0.84
0.84
0.83
0.84
1.96
1.98
1.96
1.85
2.773 (3)
2.815 (3)
1.783 (3)
2.679 (3)
163.7
176.7
170.0
169.5
Symmetry transformations used to generate equivalent atoms, #3: −x + 1, −y, −z + 1; #4: −x + 1, y + 1/2, −z + 1/2; #5: x, −y − 1/2,
z + 1/2.
FIG. 4. One-dimensional zigzag chain with polyhedron geometry around nickel(II) centers. For clarity, H atoms were omitted (color figure available online).
C3H4N2 = pyrazole).[16] In addition, three dimensional net-
Structural of [Ni(Sal-Gly)(H2O)2] (2)
The molecular strcutrue of [Ni(Sal-Gly)(H2O)] (2) with the work is generated via hydrogen bonding involving aqua and
atom-numbering scheme is shown in Figure 3 and selected bond carboxylic group (hydrogen bonds are listed in Table 4).
distances and angles are listed in Table 3. The metal center Ni(II)
adopts six-coordinated distorted octahedral geometry and is sur-
rounded by one N and two O atoms from the same Sal-Gly
ligand, two aqua ligands, and to one O from another Sal-Gly
SUPPLEMENTARY MATERIALS
Crystallographic data for the crystal structures of 1 and 2
ligand. Similar to complex 1, the Sal-Gly ligand is tetraden- reported in this article have been deposited with the Cambridge
tate. A one-dimensional zigzagic chain (Figure 4) is formed Crystallographic Data Center (CCDC No. 835882, 835883), re-
through the bidentate bridge COO− of Sal-Gly to link the ad- spectively. These materials can be obtained free of charge via
jacent copper(II) atoms. The bond distances and angles are in www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC,
normal range, which are compared to those Sal-Gly nickel(II) 12 Union Road, Cambridge CB2 1EZ, UK; Fax: t44 1223
complex (C9H7NO3)Ni(C3H4N2)3·H2O (C9H7NO3 = Sal-Gly, 336033; Email: deposit@ccdc.cam.ac.uk).

1266
S.-M. SHI ET AL.
complexes with tridentate Schiff base dianions. II. EPR study on N-
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