Synthesis, crystal structures, and antibacterial activity of two isostructural trinuclear zinc(II) complexes with 2-[(3-Dimethylaminopropylimino) methyl]-6-ethoxyphenol

Article abstract of DOI:10.1080/15533174.2010.522654

Two isostructural azido-bridged trinuclear zinc(II) complexes with the Schiff base 2-[(3-dimethylaminopropylimino)methyl]-6-ethoxyphenol were synthesized and structurally characterized by elemental analysis (C, H, N), FT-IR spectra, and single crystal X-r

Full text of DOI:10.1080/15533174.2010.522654

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 40:888–892, 2010
Copyright © Taylor & Francis Group, LLC
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2010.522654
Synthesis, Crystal Structures, and Antibacterial Activity of
Two Isostructural Trinuclear Zinc(II) Complexes with
2-[(3-Dimethylaminopropylimino)methyl]-6-ethoxyphenol
Junsong Zhang, Fanda Pan, Heng Cheng, and Wenjie Du
School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou,
P. R. China
base against the bacteria Staphylococcus aureus, Bacillus an-
thracis, Pseudomonas aeruginosa, and Streptococcus agalac-
tiae was investigated.
Two isostructural azido-bridged trinuclear zinc(II) complexes
with the Schiff base 2-[(3-dimethylaminopropylimino)methyl]-6-
ethoxyphenol were synthesized and structurally characterized by
elemental analysis (C, H, N), FT-IR spectra, and single crystal X-
ray diffraction. Both complexes possess crystallographic two-fold
rotation axis symmetry. The central Zn atom in each complex is
six-coordinated in an octahedral geometry, while the terminal Zn
atoms in each complex are five-coordinated in distorted square
pyramidal geometries. The antibacterial activity of the complexes
and the Schiff base against the bacteria Staphylococcus aureus,
Bacillus anthracis, Pseudomonas aeruginosa, and Streptococcus
agalactiae was investigated.
EXPERIMENTAL
Materials and Measurements
3-Ethoxysalicylaldehyde and N, N-dimethylpropane-1,3-
diamine were purchased from Aldrich. Other chemicals were
commercially available and were used without further purifi-
cation. Elemental analyses (C, H, N) were carried out using
Elemental CHN Analyzer Vario El III. FT-IR spectra were
recorded using KBr discs on a Nicolet AVATAR 360 spec-
trophotometer. The 1H NMR spectrum was recorded on a Varian
INOVA300 (300 MHz) pulse Fourier-transform NMR spectrom-
eter in CDCl3.
Keywords antibacterial, crystal structure, Schiff base, synthesis, zinc
INTRODUCTION
Schiff base compounds are readily synthesized from the con-
densation reaction between aldehydes with primary amines,
which have been widely investigated for their biological activ-
ities, such as antibacterial, antifungal, and antitumor.[1–5] The
imine N atom and some other donor atoms of the Schiff base
compounds easily coordinate to metal atoms, forming versa-
tile complexes.[6−8] A number of studies show that the an-
tibacterial activities of the metal complexes were increased
when compared with the corresponding Schiff bases.[9,10]
It was also reported that salicylaldehyde derivatives with
halide atoms in the aromatic rings showed good antibac-
terial activities.[11] In the present work, two isostructural
halide-coordinated zinc complexes, [Zn{ZnClL(µ1,1-N3)}]2
(1) and [Zn{ZnBrL(µ1,1-N3)}]2 (2), where L is the depro-
tonated form of 2-[(3-dimethylaminopropylimino)methyl]-6-
ethoxyphenol (HL), were synthesized and structurally character-
ized. The antibacterial activity of the complexes and the Schiff
Synthesis of the Schiff Base HL
A methanol solution (20 mL) of 3-ethoxysalicylaldehyde (1
mmol, 166 mg) was added to a methanol solution (20 mL) of
N, N-dimethylpropane-1,3-diamine (1 mmol, 102 mg) to give
yellow solution. The solution was evaporated to give yellow
micro-crystals which were washed with methanol and dried in
air. Yield: 87%. Anal. calcd. for C14H22N2O2: C, 67.2; H, 8.9;
N, 11.2%. Found: C, 66.8; H, 8.9; N, 11.0%. IR data (cm−1):
3423 w, 2931 m, 2851 w, 1645 s, 1520 m, 1483 m, 1459 m,
1398 w, 1339 w, 1290 m, 1218 s, 1165 m, 1116 m, 1030 w, 965
w, 835 m, 692 w, 650 w, 616 w, 466 w. 1H NMR (CDCl3, 300
MHz): 1.31 (t, 3H), 1.73 (m, 2H), 2.29 (s, 6H), 2.37 (t, 2H),
3.54 (t, 2H), 3.95 (q, 2H), 6.62–7.03 (m, 3H), 8.12 (s, 1H).
Synthesis of the Complex (1)
To the methanol solution (10 mL) of HL (0.1 mmol, 25.0
mg) and NaN3 (0.1 mmol, 6.5 mg) was added a methanol so-
lution (10 mL) of ZnCl2 (0.1 mmol, 13.7 mg) with stirring and
the mixture was stirred under refluxed for 30 min. The clear
colorless solution was left at room temperature to give colorless
block-shaped single crystals. Yield: 37 % with respect to ZnCl2.
Analysis calcd. for C28H42Cl2N10O4Zn3: C, 39.6; H, 5.0; N,
Received 20 December 2009; accepted 3 August 2010.
Address correspondence to Junsong Zhang, School of Food and
Biological Engineering, Zhengzhou University of Light Industry,
Zhengzhou 450002, P. R. China. E-mail: junsong zhang@126.com.
888

TWO ISOSTRUCTURAL TRINUCLEAR ZINC(II) COMPLEXES
889
TABLE 2
N
N
◦
˚
Selected bond lengths (A) and angles ( ) for complexes (1) and
(2)
OH
(1)
OEt
Bond lengths
Zn1-O1
Zn1-N3
Zn2-N1
Zn2-N3
2.350 (2)
2.066 (3)
2.096 (3)
2.180 (3)
Zn1-O2
Zn2-O2
Zn2-N2
Zn2-Cl1
2.013 (2)
2.080 (2)
2.114 (3)
SCH. 1. The Schiff base HL.
16.5 %. Found: C, 39.1; H, 5.3; N, 16.8 %. IR data (cm−1):
2930 w, 2853 w, 2038 vs, 1628 s, 1532 m, 1445 w, 1286 m,
1223 m, 1181 m, 1169 w, 1123 m, 1027 w, 977 w, 823 w, 745
m, 640 w, 577 w.
2.2708 (11)
Bond angles
O2A-Zn1-O2
O2-Zn1-N3
O2A-Zn1-O1
N3-Zn1-O1
O1-Zn1-O1A
O2-Zn2-N2
O2-Zn2-N3
N2-Zn2-N3
N1-Zn2-Cl1
N3-Zn2-Cl1
175.3 (1)
78.2 (1)
110.7 (1)
145.4 (1)
80.6 (1)
118.6 (1)
74.2 (1)
93.4 (1)
99.6 (1)
99.0 (1)
O2A-Zn1-N3
N3-Zn1-N3A
O2-Zn1-O1
N3A-Zn1-O1
O2-Zn2-N1
N1-Zn2-N2
N1-Zn2-N3
O2-Zn2-Cl1
N2-Zn2-Cl1
99.1 (1)
111.3 (2)
73.1 (1)
92.1 (1)
84.6 (1)
91.8 (1)
158.1 (1)
133.0 (1)
108.1 (1)
Synthesis of the Complex (2)
The preparation of complex (2) was similar to that described
for complex (1), which was obtained from HL, NaN3 and
ZnBr2. Yield: 43 % with respect to ZnBr2. Analysis calcd. for
C28H42Br2N10O4Zn3: C, 35.8; H, 4.5; N, 14.9 %. Found: C,
35.5; H, 4.9; N, 14.4 %. IR data (cm−1): 2930 w, 2853 w, 2039
vs, 1628 s, 1532 m, 1445 w, 1285 m, 1222 m, 1181 m, 1168 w,
1123 m, 1026 w, 973 w, 825 w, 741 m, 640 w, 573 w.
(2)
Bond lengths
2.0159 (18)
2.059 (2)
2.096 (2)
2.174 (2)
TABLE 1
Crystal data and structural refinement details for complexes (1)
and (2)
Zn1-O1
Zn1-N3
Zn2-N1
Zn2-N3A
Zn1-O2
Zn2-O1
Zn2-N2
Zn2-Br1
2.347 (2)
2.0752 (19)
2.111 (3)
Complex
(1)
(2)
2.4053 (6)
Bond angles
Chemical formula C28H42Cl2N10O4Zn3 C28H42Br2N10O4Zn3
O1A-Zn1-O1
O1-Zn1-N3
O1A-Zn1-O2
N3-Zn1-O2
O2-Zn1-O2A
O1-Zn2-N2
O1-Zn2-N3A
N2-Zn2-N3A
N1-Zn2-Br1
N3A-Zn2-Br1
175.6 (1)
99.3 (1)
110.5 (1)
92.5 (1)
79.9 (1)
117.0 (1)
74.4 (1)
94.3 (1)
99.1 (1)
98.6 (1)
O1A-Zn1-N3
N3-Zn1-N3A
N3-Zn1-O2A
O1-Zn1-O2
O1-Zn2-N1
N1-Zn2-N2
N1-Zn2-N3A
O1-Zn2-Br1
N2-Zn2-Br1
78.2 (1)
111.3 (2)
145.3 (1)
73.1 (1)
84.5 (1)
91.4 (1)
158.4 (1)
133.7 (1)
109.1 (1)
Formula weight
Color and habit
T (K)
849.73
colorless, block
298(2)
Mo Kα (0.71073)
Monoclinic
C2/c
938.65
colorless, block
298(2)
Mo Kα (0.71073)
Monoclinic
C2/c
˚
Radiation (λ, A)
Crystal system
Space group
˚
a(A)
23.061(4)
10.568(2)
17.306(3)
120.967(2)
3616.3(12)
4
23.117(4)
10.5868(16)
17.271(3)
121.111(2)
3618.9(9)
4
˚
b(A)
˚
c(A)
β (o)
V (A )
3
˚
Z
Crystal Structure Determination
–3
dcalcd (g cm
µ (mm
F(000)
)
1.561
2.169
1744
1.723
4.228
1888
Crystals with dimensions 0.27 × 0.25 × 0.25 mm3 for (1)
and 0.18 × 0.17 × 0.17 mm3 for (2) were mounted and data
were collected at 298(2) K on a Bruker SMART 1000 CCD
–1
)
No. of unique data
No. of restraints
No. of parameters
GOF on F2
3742
0
216
1.030
0.0377
0.0858
3906
0
216
1.034
0.0331
0.0766
˚
area-detector with Mo Kα radiation (λ = 0.71073 A). A total
of 14159 reflections were collected in the range 2.06◦ < θ <
26.50o (–28 ≤ h ≤ 28, –13 ≤ k ≤ 13, –21 ≤ l ≤ 21). A
total of 14632 reflections were collected in the range 2.06◦ <
θ < 27.00◦ (–29 ≤ h ≤ 29, –13 ≤ k ≤ 13, –21 ≤ l ≤ 22).
Empirical absorption corrections were applied using the SAD-
ABS program.[12] Both structures were solved by direct meth-
ods and refined by a full matrix least-squares technique based
on F2 using the SHELXL 97 program.[13] All non-hydrogen
atoms were refined anisotropically. All hydrogen atoms were
R1a [I ≥ 2σ(I)]
R1a (all data)
wRb2 [I ≥ 2σ(I)]
wRb2 (all data)
ꢀ
0.0535
0.0931
0.0463
0.0816
ꢀ
ꢀ
b
aR1
=
||Fo|
–
|Fc||/ |Fo|,
wR2
=
[
w(Fo2
–
ꢀ
Fc2)2/ w(Fo2)2]1/2
.

890
J. ZHANG ET AL.
refined as riding atoms. Selected crystallographic data and struc-
ture determination parameters for complexes (1) and (2) are
given in Table 1. Selected bond lengths and angles for (1) and
(2) are listed in Table 2. X-ray crystallographic data for the
complexes have been deposited with the Cambridge Crystal-
lographic Data Centre (The Director, CCDC, 12 Union Road,
Cambridge, CB2 1 EZ, UK; e-mail: deposit@ccdc.cam.ac.uk;
http://www.ccdc.cam.ac.uk; fax: +44-(0)1223-336033) and are
available free of charge on request, quoting the deposition num-
ber CCDC 752998 for (1) and 752999 for (2)).
Antibacterial Test
The two complexes and the Schiff base were determined
against the bacteria Staphylococcus aureus, Bacillus anthracis,
Pseudomonas aeruginosa, and Streptococcus agalactiae. Mi-
croorganisms were cultured on Mu¨ller–Hinton agar medium.
The gentamicin was used as a reference. After drilling wells on
medium using a 6 mm cork borer, 100 µL of solution from dif-
ferent compound were poured into each well. The plates were
incubated at 37◦C overnight. The diameter of the inhibition zone
was measured to the nearest. Each test was carried out in tripli-
cate, and the average was calculated for inhibition zone diame-
ters. A blank containing only methanol showed no inhibition in
a preliminary test. The macro-dilution broth susceptibility assay
was used for the evaluation of minimal inhibitory concentration
(MIC). By including 1 mL Mu¨ller-Hinton broth in each test,
FIG. 1. Molecular structure of (1) at 30% probability displacement.
methanol (Scheme 2). The Schiff base and the two complexes
were stable at room temperature in air. The molar conductivities
at 10–3 mol L–1 concentration for the complexes in acetonitrile
were in the expecting range for non-electrolytes.[14]
Structure Description of the Complexes
The molecular structures of the isostructural azido-bridged
trinuclear zinc(II) complexes (1) and (2) are shown in Figures
1 and 2, respectively. Both complexes possess crystallographic
two-fold rotation axis symmetry. The azide ligands adopt end-
–1
and then adding 1 mL extract with concentration 100 mg mL
in the first tube, we made a serial dilution of this extract from
first tube to last tube. Bacterial suspension prepared to match
the turbidity of 0.5 Mcfarland turbidity standards. Matching this
turbidity provides a bacterial inoculum concentration of 1.5 ×
108 cfu mL–1. Then 1 mL of bacterial suspension was added to
each test tube. After incubation at 37◦C for 24 h, the last tube
was determined as the MIC without turbidity.
˚
on coordination mode. The Zn· · ·Zn distances are 3.276(2) A in
˚
(1) and 3.268(2) A in (2).
The central Zn atom in each complex is six-coordinated by
two phenolic O and two ether O atoms from two Schiff base lig-
ands, and by two terminal N atoms from two bridging azide
groups, forming an octahedral coordination. The coordinate
bond lengths and angles about the central Zn atoms in both
complexes are comparable to each other. The octahedral coor-
dinations in the complexes are distorted, as evidenced by the
RESULTS AND DISCUSSION
The Schiff base HL was synthesized by the condensation bond angles. The three trans angles subtended at Zn1 are in the
of 3-ethoxysalicylaldehyde with N, N-dimethylpropane-1,3- range 145.4(1)–175.3(1)◦ in (1) and 145.2(1)–175.6(1)◦ in (2),
diamine in a methanol solution with good yield and high purity. and the other angles subtended at Zn1 are in the range 73.1(1)–
The two zinc complexes were synthesized by the reaction of 111.3(2)◦ in (1) and 73.1(1)–111.3(2)◦ in (2), all of which are
equimolar quantities of the Schiff base, NaN3 and zinc halide in much deviated from the values for an ideal octahedral geometry.
O
O
N
Zn
N
MeOH
Reflux
O
O
ZnX2
+
NaN3
+
N
OH
N
Zn
Zn
N3
N3
X
OEt
X
N
N
SCH. 2. The synthesis procedure of the complexes [X = Cl for (1) and Br for (2)].

TWO ISOSTRUCTURAL TRINUCLEAR ZINC(II) COMPLEXES
891
TABLE 3
Zone of growth inhibition of the test compounds against the bacteria
Zone of growth inhibition (mm)
Compound
Staphylococcus aureus
Bacillus anthracis
Pseudomonas aeruginosa
Streptococcus agalactiae
HL
(1)
(2)
gentamicin
9
13
27
22
35
19
32
25
17
11
17
15
15
20
17
30
117.0(1)◦ for (2), which are deviate from the values for an ideal
square pyramidal geometry.
In both complexes, the coordinate bond lengths are compa-
rable to the corresponding values observed in other Schiff base
zinc complexes.[16−18]
IR Spectra
Compared with the IR spectrum of the Schiff base ligand,
–1
it was shown that the ν(C=N) absorption band at 1645 cm
–1
are shifted to lower frequencies by 17 cm in the complexes,
indicating that the Schiff base ligand is coordinated to the Zn
atoms through the imine N atom. The absence of the OH bands
of the free Schiff base ligands in the complexes indicates that
the phenol groups have been deprotonated and coordinated to
–1
the Zn atoms. The strong absorption bands at 1218 cm in
the Schiff base ligand assigned to the phenolic C–O linkage,
which is shifted towards lower wave numbers of 1181 cm
FIG. 2. Molecular structure of (2) at 30% probability displacement.
–1
for the complexes, confirming the involvement of OH groups
in coordination. The strong absorption bands indicative of the
The terminal Zn atom in each complex is five-coordinate in
a square pyramidal geometry, with the basal plane defined by
one phenolic O and one imine N atoms of a Schiff base ligand,
one terminal N atom of an azide group, and a halide atom (Cl
for (1) and Br for (2)), and with the apical position occupied by
one amine N atom of a Schiff base ligand. The square-pyramidal
azide groups are at 2038 cm for (1) and 2039 cm–1 for (2).
–1
Antibacterial Activity
The antibacterial activity of the Schiff base, the two com-
geometry is distorted, with the τ value of 0.418 for (1) and 0.412 plexes, and the reference gentamicin against the bacteria Staphy-
for (2).[15] The Zn-O and Zn-N bonds in the square pyramidal lococcus aureus, Bacillus anthracis, Pseudomonas aeruginosa,
coordinations in both complexes are comparable to each other. and Streptococcus agalactiae as zone of growth inhibition is
The Zn-Cl bonds in (1) are much shorter than the Zn-Br bonds summarized in Table 3. The MIC values are listed in Table 4.
in (2). The bond angles among the apical and the basal donor
The antibacterial activities of the two complexes are stronger
atoms are in the range 91.8(1)–118.6(1)◦ for (1) and 91.4(1)– than those of the Schiff base HL. It is notable that the antibacte-
TABLE 4
MIC values of the test compounds against the bacteria
–1
MIC (mg mL
)
Compound
Staphylococcus aureus
Bacillus anthracis
Pseudomonas aeruginosa
Streptococcus agalactiae
HL
(1)
(2)
gentamicin
13.0
5.5
7.0
3.5
11.5
3.5
5.0
3.0
9.0
5.5
4.0
7.0
12.0
7.5
11.0
20.0

892
J. ZHANG ET AL.
rial activity of the chloride-coordinated complex (1) is stronger
than that of the bromide-coordinated complex (2), and even
comparable with the gentamicin.
7. Zhang, C.-X., Cui, C.-X., Lu, M., Yu, L., and Zhan, Y.-X. In situ synthesis,
characterization and crystal structure of a novel cobalt(III) complex with
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A new tetradentate N2O2-type Schiff base ligand. Synthesis, extractive
properties towards transition metal ions and X-ray crystal structure of its
nickel complex. Transition Met. Chem., 2007, 32, 374–378.
9. Bagihalli, G.B., Avaji, P.G., Patil, S.A., and Badami, P.S. Synthesis, spectral
characterization, in vitro antibacterial, antifungal and cytotoxic activities of
Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur. J.
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CONCLUSION
Two isostructural azido-bridged trinuclear zinc(II) com-
plexes with the Schiff base 2-[(3-dimethylaminopropylimino)-
methyl]-6-ethoxyphenol has been synthesized and structurally
characterized. The Schiff base coordinates to the Zn atoms
through the phenolic O, imine N and amine N atoms. Both
complexes show stronger antibacterial activity than that of the
free Schiff base, and the antibacterial activity of the chloride-
10. Sun, Y.-X. Synthesis, crystal structures and antibacterial activities of two
Schiff base copper(II) complexes. Synth. React. Inorg. Met.-Org. Nano-Met.
Chem., 2006, 36, 621–625.
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