Synthesis, crystal structure, and properties of two novel complexes based on zaltoprofen ligand

Article abstract of DOI:10.1080/15533174.2012.762383

Two novel metal-organic coordination complexes [Cd(Zalto profen)2(H2O)3](H2O) (1), [Zn(Zaltoprofen)(H2O)]n (2) (where zaltoprofen = 5-(1-carboxyethyl)-2-(phenylthio)phenylacetic acid) have been synthesized under normal conditions and hydrothermal conditions, respectively. And characterized by single crystal X-ray diffraction, elemental analysis, spectral method (IR), powder X-ray diffraction (XRD), and fluorescent properties. Compound 1 crystallizes in the monoclinic Cc space group while compound 2 in the monoclinic system with space group P21 /c. [Cd(Zaltoprofen)2(H2O)3](H2O) (1) features 0-D structural, the hydrogen-bonds play a vital role in determining the crystal packing and construction of the extended 3-D supramolecular network. [Zn(Zaltoprofen)(H2O)]n (2) displays a 2D net with alternately arranged left- and right-handed helical chains. The O-H···O hydrogen bonding play an important role in stabilizing the structure. Supplemental materials are available for this article. Go to the publisher's online edition of Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry to view the supplemental file.

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Synthesis, Crystal Structure, and Properties of Two
Novel Complexes Based on Zaltoprofen Ligand
Jin-Niu Tang a , Xia Yin b , Xian-Hong Yin a , Wen-Jia Xu a , Gang-Hong Pan a & Zhong-Jing
Huang a
a College of Chemistry and Chemical Engineering, Guangxi University for Nationalities ,
Nanning , P. R. China
b Middle School of Dongkou Hunan , Dongkou , P. R. China
Accepted author version posted online: 10 Oct 2013.Published online: 21 Nov 2013.
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To cite this article: Jin-Niu Tang , Xia Yin , Xian-Hong Yin , Wen-Jia Xu , Gang-Hong Pan & Zhong-Jing Huang (2014) Synthesis,
Crystal Structure, and Properties of Two Novel Complexes Based on Zaltoprofen Ligand, Synthesis and Reactivity in Inorganic,
Metal-Organic, and Nano-Metal Chemistry, 44:4, 582-589, DOI: 10.1080/15533174.2012.762383
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ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2012.762383
Synthesis, Crystal Structure, and Properties of Two Novel
Complexes Based on Zaltoprofen Ligand
Jin-Niu Tang,1 Xia Yin,2 Xian-Hong Yin,1 Wen-Jia Xu,1 Gang-Hong Pan,1
and Zhong-Jing Huang1
1College of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning,
P. R. China
2Middle School of Dongkou Hunan, Dongkou, P. R. China
asymmetric catalysis and nonlinear optics.[5–12] Metal–organic
Two novel metal-organic coordination complexes [Cd(Zalto
profen)2(H2O)3](H2O) (1), [Zn(Zaltoprofen)(H2O)]n (2) (where
zaltoprofen = 5-(1-carboxyethyl)-2-(phenylthio)phenylacetic acid)
have been synthesized under normal conditions and hydrother-
mal conditions, respectively. And characterized by single crystal
X-ray diffraction, elemental analysis, spectral method (IR), pow-
der X-ray diffraction (XRD), and fluorescent properties. Com-
pound 1 crystallizes in the monoclinic Cc space group while
compound 2 in the monoclinic system with space group P21/c.
[Cd(Zaltoprofen)2(H2O)3](H2O) (1) features 0-D structural, the
hydrogen-bonds play a vital role in determining the crystal pack-
ing and construction of the extended 3-D supramolecular network.
[Zn(Zaltoprofen)(H2O)]n (2) displays a 2D net with alternately ar-
ranged left- and right-handed helical chains. The O–H···O hydro-
gen bonding play an important role in stabilizing the structure.
helical structures containing single-, double-, and multistranded
helices[13–21] have been constructed; the chemistry of coordina-
tion polymers with helical structures has been reviewed.[22,23]
Hydrogen-bonding plays an important role in the fabrication of
the supramolecular architectures.
In this respect, the influence of ligand spacers of flexible
bridging ligands on framework formation of their coordina-
tion polymers has widely been documented.[24–28] Zaltoprofen
is one of non-steroidal anti-inflammatory drugs that exhibit fa-
vorable anti-inflammatory, analgesic, and antipyretic properties.
Most anti-inflammatory drugs are carboxylic acids in which car-
boxylate is available for metal–ligand interaction. Much work
has focused on interactions of transition metal ions with non-
steroidal anti-inflammatory drugs such as ibuprofen, fenopro-
fen.[29,30] But to our knowledge, using Zaltoprofen to construct
metal–organic frameworks has not been reported. As a multi-
functional ligand, Zaltoprofen has attracted our attention on the
basis of the following considerations. The multicarboxylates
are capable of functioning as hydrogen bond donors and/or ac-
ceptors. The carboxyl is always deprotonated to compensate
the charge of the metal ions, and it may allow for diversity in
the coordination mode. The flexible Zaltoprofen building blocks
considered as V-shaped dicarboxylate may generate helical
chains.
As a continuation of our research, we report synthesis,
crystal structure, elemental analyses, IR spectrum, powder
XRD, and fluorescent properties of two novel complexes
[Cd(Zaltoprofen)2(H2O)3](H2O) (1), [Zn(Zaltoprofen)(H2O)]n
(2), which are constructed and stabilized the framework
via Hydrogen-bonding. Photoluminescence properties of com-
plexes in DMF/EtOH have also been investigated below in de-
tail.
Supplemental materials are available for this article. Go to the
publisher’s online edition of Synthesis and Reactivity in Inorganic,
Metal-Organic, and Nano-Metal Chemistry to view the supplemen-
tal file.
Keywords Cd(II) complex, single-crystal structure, zaltoprofen,
Zn(II) complex
INTRODUCTION
In recent years, the low-dimensional coordination polymers
have received much attention owing to their intriguing struc-
tural features and potential as functional materials different
from those of 3-D coordination polymers.[1–4] A particularly
interesting and challenging area is the synthesis of helical co-
ordination polymers and exploration of their potential utility in
Received 6 December 2012; accepted 20 December 2012.
The authors thank The authors thank the National Natural Science
Foundation of China (20761002), PR China and the Natural Science
Foundation of Guangxi (053020), P. R. China
Address correspondence to Zhong-Jing Huang, College of Chem-
istry and Chemical Engineering, Guangxi University for Nationalities,
Nanning 530006, P. R., China. E-mail: 382645034@qq.com
EXPERIMENTAL
All chemicals were commercial materials of analytical grade
and used without purification. Elemental analysis for C, H, and
N was carried out on a Perkin-Elmer 2400 II elemental analyzer.
582

ZALTOPROFEN COMPLEX HAS NOT BEEN REPORTED
583
TABLE 1
Experimental data for complex 1 and 2
1
2
Empirical formula
Formula weight
C34H38CdO12S2
815.16
C17H16ZnO5S
397.73
Temperature
296(2) K
296(2) K
Wavelength
Crystal system, space group
0.71073 Å
Monoclinic, Cc
38.520(2)
11.423(3)
8.145(3)
90.703(1)
3583.8(2)
4
0.71073 Å
Monoclinic, P21/c
18.492(2)
5.436(1)
19.104(3)
120.688(1)
1651.3(5)
4
a (Å)
b (Å)
c (Å)
β (◦)
Volume (Å3)
Z
Dcalcd. (Mg·m−3
)
1.511
0.787
1672
1.600
1.637
816
Absorption coefficient (mm−1
F(000)
)
Crystal size
0.23 × 0.22 × 0.20
1.06–25.00
8971
0.38 × 0.35 × 0.33
2.13–25.00
8436
θ range for data collection (◦)
Reflections collected
Unique reflections
4598 [R(int) = 0.0421]
2910 [R(int) = 0.0284]
Completeness to θ = 25.00
Absorption correction
Max. and min. transmission
Data / restraints / parameters
Goodness-of-fit on F2
R indices [I > 2σ(I)]
R indices (all data)
99.6%
99.9%
Semiempirical
0.854 and 0.834
4598 / 39 / 390
1.093
R1 = 0.0905, wR2 = 0.2465
R1 = 0.0974, wR2 = 0.2533
3.118 and 1.636
Semiempirical
0.583 and 0.542
2910 / 7 / 218
1.029
R1 = 0.0343, wR2 = 0.0868
R1 = 0.0430, wR2 = 0.0945
0.748 and −0.475
Largest diff. peak and hole (e.Å−3
)
The FT-IR spectrum was obtained on a PE Spectrum One 1187 (w), 1072 (w), 1023 (w), 944 (w), 906 (w), 831 (w), 808
FT-IR Spectrometer Fourier transform infrared spectroscopy in (w), 739 (m), 689 (m), 623 (w), 540 (w), 490 (w), 471 (w).
the 4000-400 cm−1 regions, using KBr pellets. Powder X-ray
diffraction patterns were obtained using a pinhole camera
(Anton Paar) operating with a point focused Ni-filtered Cu Kα
radiation in the 2θ range from 5◦ to 50◦ with a scan rate of
Synthesis of [Zn(Zaltoprofen)(H2O)]n (2)
0.08◦ per second.
The reagents of ZnCl2·6H2O (0.2975 g, 1 mmol), Zaltoprofen
(0.1582 g, 0.5 mmol) 20 mL mixed solvent of CH3CH2OH /H2O
(volume ratio 1:3) were sealed in a 30 mL Teflon-lined stainless
reactor, an aqueous solution of sodium hydroxide was added
dropwise with stirring to adjust the pH value of the solution
being 6 and the mixture was stirred for 0.5 h, then kept under
autogenous pressure at 160◦C for 24 h. The resulting reaction
mixture was slowly cooled to room temperature at a rate of
5◦C per hour. The colorless block crystals suitable for X- ray
diffraction were isolated directly, Yield: 58%, based on Zn.
Anal. Calcd. for C17H16ZnO5S (%): C, 51.33; H, 4.05. Found:
C, 51.48; H, 4.27. IR data (KBr pellets, cm-1): 3432 (s), 2977
(w), 1615 (vs), 1565 (vs), 1425 (w), 1383 (s), 1284 (w), 1254
(w), 1065 (w), 1023 (w), 904 (w), 837 (w), 802 (m), 736 (m),
689 (m), 651 (w), 469 (w).
Synthesis of [Cd(Zaltoprofen)2(H2O)3](H2O) (1)
CdSO4·8/3H2O (0.2565 g, 0.1 mmol), Zaltoprofen (0.1582 g,
0.5 mmol) were dissolved in the mixture of 10 mL CH3CH2OH
and 10 mL H2O. Then an aqueous solution of sodium hydroxide
was added dropwise with stirring to adjust the pH value of the
solution being 6. The mixture was kept stirring for 6 h at 74◦C
and then filtered. The filtrate was kept at room temperature and
a few days later X-ray quality colorless block-shaped single
crystals were obtained. The colorless block crystals suitable for
X-ray diffraction were isolated directly, Yield: 74%, based on
Cd. Anal. Calcd. for C34H38CdO12S2 (%): C,50.09; H, 4.70.
Found: C, 50.27; H, 4.86. IR data (KBr pellets, cm−1): 3417 (s),
2981 (w), 1665 (vs), 1542 (vs), 1476 (m), 1396 (m), 1302 (m),

584
J.-N. TANG ET AL.
TABLE 2
Empirical absorption corrections were applied using the SAD-
The selected bond lengths (Å) and angles (◦)
ABS program.[31] The complexes were solved by Patterson
method and direct method, respectively. And refined by full-
matrix least squares on F2 using the SHELXTL program.[32] All
non-hydrogen atoms were refined anisotronically. A summary
of the crystallographic data and structure refinement is shown
in Table 1, selected bond lengths and angles of the complexes
are listed in Table 2.
Complex 1
2.262(1)
2.18(2)
2.352(1)
2.520(1) O(11)-Cd(1)-O(7)
Cd(1)-O(5)
Cd(1)-O(11)
Cd(1)-O(10)
Cd(1)-O(7)
Cd(1)-O(1)
Cd(1)-O(2)
2.225(2)
2.346(1)
2.442(1)
98.5(7)
132.8(5)
89.8(5)
168.4(7)
92.4(5)
90.5(7)
84.3(5)
78.2(4)
53.3(5)
139.8(5)
152.1(3)
Cd(1)-O(6)
O(11)-Cd(1)-O(5)
O(11)-Cd(1)-O(1)
O(5)-Cd(1)-O(1)
O(7)-Cd(1)-O(10)
O(1)-Cd(1)-O(10)
O(7)-Cd(1)-O(2)
O(1)-Cd(1)-O(2)
O(11)-Cd(1)-O(6)
O(5)-Cd(1)-O(6)
O(10)-Cd(1)-O(6)
83.8(7)
86.1(6)
O(7)-Cd(1)-O(5)
O(7)-Cd(1)-O(1)
137.3(5) O(11)-Cd(1)-O(10)
92.1(5) O(5)-Cd(1)-O(10)
89.3(5) O(11)-Cd(1)-O(2)
RESULTS AND DISCUSSION
142.4(5)
O(5)-Cd(1)-O(2)
54.3(4) O(10)-Cd(1)-O(2)
Description of the Structure
111.8(7)
81.9(5)
78.3(5)
O(7)-Cd(1)-O(6)
O(1)-Cd(1)-O(6)
O(2)-Cd(1)-O(6)
Complex 1 crystallizes in the monoclinic space group of
Cc. In complex 1 the asymmetric unit contains one Cd(II)
ions, four water molecules, and two half deprotonated Zal-
toprofen– ligands. The Cd(II) center is seven-coordinated by
four oxygen atoms (O1, O2, O6, O7) of the carboxylate from
two Zaltoprofen– ligands and one oxygen atoms (O5) from one
water molecule composing the equatorial plane, and two oxy-
gens atoms (O10, O11) from two water molecules at the axial
sites (Figure 1). The Cd-O bond distances vary from 2.18(2) to
2.520(1) Å. One carboxylate group adopts a μ1-η1:η1 chelating
coordination mode to connect one Cd(II) atom while the other
carboxylate group is not coordinated. There are hydrogen bonds
among all the oxygen atom (O3, O4, O8, O9) of the nondeproto-
nated carboxyl group, the oxygen atoms (O1, O2, O6, O7) of the
Complex 2
Zn(1)-O(1)
Zn(1)-O(5)
O(1)-Zn(1)-O(4)#1
O(4)#1-Zn(1)-O(5)
1.947(2)
1.971(2)
95.87(9)
Zn(1)-O(4)#1
Zn(1)-O(3)#2
O(1)-Zn(1)-O(5)
1.957(2)
1.982(2)
125.97(9)
111.89(9) O(1)-Zn(1)-O(3)#2 102.82(9)
O(4)#1-Zn(1)-O(3)#2 115.24(9) O(5)-Zn(1)-O(3)#2 105.25(9)
Symmetry transformations used to generate equivalent atoms: for
complex 1: #1 −x, −y, −z + 1; for complex 2: #1 −x, −y + 1, −z
#2 x, −y + 3/2, z − 1/2.
Crystal Structure Determination
Single crystal of the complex was mounted on glass fibers and coordinated carboxyl group, the oxygen atoms (O5, O10, O11)
measured on a Bruker SMART CCD area detector at 298 K us- of the coordinated water molecule and the oxygen atom (O12)
ing graphite monochromated Mo Ka radiation (λ = 0.71073 Å). of the uncoordinated water molecule, determining the crystal
FIG. 1. The coordination environment of Cd(II) ion of complex 1, All the hydrogen atoms are omitted for clarity. (color figure available online).

ZALTOPROFEN COMPLEX HAS NOT BEEN REPORTED
585
FIG. 2. The 3D framework of complex 1 via H-bonding. The unnecessary hydrogen atoms are omitted for clarity. (color figure available online).
FIG. 3. The coordination environment of Zn(II) ion of complex 2, All the hydrogen atoms are omitted for clarity. (color figure available online).

586
J.-N. TANG ET AL.
TABLE 3
Hydrogen-bonding geometries (Å) for 1 and 2
Symmetry
D–H. . .A
codes
D-H
H. . .A
D. . .A
D–H. . .A
Complex 1
O9-H9A. . .O6
O4-H4A. . .O2
O12-H12B. . .O10
O12-H12A. . .O7
O11-H11B a. . .O1
O11-H11A a. . .O12
O10-H10D. . .O8
O10-H10C. . .O3
O5-H5B. . .O3
O5-H5A. . .O8
Complex 2
x, −y + 2, z − 1/2
x, −y + 2, z − 1/2
0.82
0.82
0.85
0.85
0.85
0.85
0.85
0.85
0.85
0.85
1.772
1.805
2.27
2.56
2.12
2.03
1.97
1.99
2.06
2.18
2.588
2.619
173.01
171.49
139.9
157.9
132.9
138.4
168.2
167.0
124.5
121.5
2.97(2)
3.36(2)
2.77(2)
2.72(2)
2.80(1)
2.82(1)
2.64(1)
2.72(1)
x, −y + 1, z + 1/2
x, y, z + 1
x, −y + 2, z + 1/2
x, −y + 2, z + 1/2
x, y, z + 1
x, y, z + 1
O5-H5C. . .O2
O5-H5B. . .O1
−x, −y + 2, −z
x, y + 1, z
0.85
0.85
1.82
1.95
2.663(3)
2.786(3)
169.5
169.9
FIG. 4. View of the 2D Zn(II)/Zaltoprofen2− net constructed by alternately left- and right-handed helical chains of complex 2. Unnecessary atoms are omitted
for clarity. (color figure available online).

ZALTOPROFEN COMPLEX HAS NOT BEEN REPORTED
587
FIG. 5. View of the O–H···O hydrogen bonds in 2. All unnecessary hydrogens are omitted for clarity. (color figure available online).
the coordinated carboxyl group at 1542 cm−1. The correspond-
ing bands of the monodentate coordinated carboxylate groups at
1615 cm−1 as well as the bidentate coordinated carboxyl group
at 1565 cm−1 for complex 2. The shift to the lower position
suggests that the relevant oxygen of the ligand coordinates to
metal.
packing and construction of the extended 3-D supramolecular
network (Figure 2 and Table 3).
The single-crystal X-ray diffraction analysis reveals that
polymer 2 crystallizes in the monoclinic system, space group
P21/c. The asymmetric unit consists of one Zn(II) ion, one water
molecule and one completely deprotonated Zaltoprofen2− lig-
and. As showed in Figure 3, the coordination environment
around the Zn(II) center is best portrayed as a distorted [ZnO4]
tetrahedron geometry, ligated by three oxygen donors (O1, O3A,
O4B) belonging to three Zaltoprofen2− ligands and one oxygen
donor (O5) from one water molecule. The bond lengths of Zn-
O are between 1.947(2) and 1.982(2) Å. In 2, two carboxylate
groups of the V-shape ligand Zaltoprofen2− adopt different co-
ordination modes: one carboxylate group adopts μ1-η1:η0 mode
and the other adopts μ2-η1: η1-bridging mode. The Zaltopro-
fen2− ligand acts as a μ3-bridge linking Zn(II) ions to produce
a 2D net with alternately arranged left- and right-handed heli-
cal chains (Figure 4). The O–H···O hydrogen bonding play an
important role in stabilizing 2D layer (Figure 5 and Table 3).
XRD Patterns
Simulated and experimental powder X-ray diffraction
(PXRD) patterns of complexes 1 and 2 are shown in Figure S1.
All the peaks in the recorded curves approximately match those
in the simulated curves generated from single-crystal diffraction
data, which confirms the phase purity of the as-prepared prod-
ucts. The difference in reflection intensity between the simulated
and experimental patterns is due to a certain degree of preferred
orientation of the powder samples during data collection.
Fluorescence Properties
Inorganic-organic hybrid coordination polymers, especially
those with d10 metal centers, have been investigated for photo-
luminescent properties. Previous studies have shown that coor-
IR Spectra
Dried samples of complex was characterized by IR spec- dination polymers containing cadmium(II) and zinc(II) exhibit
troscopy. In the IR spectra of two complexes, the strong and photoluminescent properties.[33–38] The fluorescence properties
broad absorption bands at about 3500-3230 cm−1 are attributed of the complexes were studied in DMF/EtOH (1/1) at room tem-
to the symmetric O–H stretching modes. The IR spectrum of perature (298 K) (Figure 6). The complexes 1 and 2, upon excita-
free ligand shows strong bands of the carboxylate groups at tion at the wavelengths where their two MLCT absorption max-
1697 cm−1, which can be assigned as the ν(C O) antisymmet- ima are observed, exhibit broad luminescent maxima at 738 nm
ric stretching vibrations. In complex 1, the corresponding bands (λex = 371 nm) for 1 and at 683 nm (λex = 344 nm) for 2 in
of the nondeprotonated carboxylate groups at 1665 cm−1 while DMF/EtOH at room temperature, which remain unchanged with

588
J.-N. TANG ET AL.
FIG. 6. Emission spectra of complex 1 (black) and 2 (red) in DMF/EtOH (1/1) recorded at room temperature. (color figure available online).
the energy of excitation wavelengths. For excitation wavelength SUPPLEMENTARY MATERIALS
between 320 and 480 nm, There is no obvious emission observed
for free Zaltoprofen. Therefore, the fluorescent emissions in the
coordination polymers may be proposed to originate from the
coordination of Zaltoprofen anion to the metal atoms. The spec-
troscopic behavior of the complexes containing Zaltoprofen as a
ligand is discussed in various spectroscopic transitions including
ligand-centered and metal-ligand charge transfer.
Further information about the crystallographic analysis
is deposited in the “Cambridge Crystallographic Data Cen-
ter” with registration number CCDC 907643 for 1 and
907642 for 2. These data can be obtained free of charge via
www.ccdc.cam.ac.uk/data request/cif, by e-mailing data de-
posit@ccdc.cam.ac.uk, or by contacting The Cambridge Crys-
tallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK; fax +44(0)1223-336-033.
CONCLUSION
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fluorescence properties. The complex 1 is an 0–D structure
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and right-handed helical chains. The successful preparation
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coordination polymers constructed by Zaltoprofen with more
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