Syntheses, crystal structures, and characterization of two Mn(II) coordination polymers with bis(4-(1H-imidazol-1-yl)phenyl) methanone ligands

Article abstract of DOI:10.1515/znb-2016-0050

Two Mn(II) complexes, {[Mn(BIPMO)₂Cl₂]·2(H₂O)}_n (1) and {[Mn(BIPMO)₂(SCN)₂]·2(CH₃OH)}_n (2) (BIPMO = bis(4-(1H-imidazol-1-yl)phenyl)methanone) with V-shaped BIPMO ligands, were synthesized and characterized by IR spectroscopy and elemental analyses along with their single-crystal X-ray diffraction analyses. The Mn(II) ions in 1 and 2 are both six-coordinated to four nitrogen atoms of four BIPMO ligands and two anions (Cl^- for 1, and SCN^- for 2) to form a distorted octahedral geometry.

Full text of DOI:10.1515/znb-2016-0050

Z. Naturforsch. 2016; 71(8)b: 869–874
Gao-Feng Wanga,*, Xiao Zhanga,*, Shu-Wen Sun, Hong Sun, Xia Yang, Hui Li, Chen-Zhong Yao,
Shu-Gang Sun, Yu-Peng Tang and Li-Xin Meng
Syntheses, crystal structures, and
characterization of two Mn(II) coordination
polymers with bis(4-(1H-imidazol-1-yl)phenyl)
methanone ligands
DOI 10.1515/znb-2016-0050
is still the appropriate choice of well-designed organic
ligands as bridges or terminal groups (building blocks)
with metal ions or metal clusters as nodes. Among various
organic ligands, N-donor ligands are often selected as
multifunctional organic linkers because of their unique
ability to coordinate metal ions, allowing for various
structural topologies, and also because of their ability to
act as hydrogen bond acceptors to assemble supramolecu-
lar structures [9, 10].
Many bi-, tri-, and multidentate N-donor ligands
have been reported, but the chemistry is still underdevel-
oped [11–13]. In this paper, we report the syntheses and
characterization of two coordination polymers with the
Received February 21, 2016; accepted April 7, 2016
Abstract: Two Mn(II) complexes, {[Mn(BIPMO)2Cl2] ·
2(H2O)}n (1) and {[Mn(BIPMO)2(SCN)2] · 2(CH3OH)}n (2)
(BIPMO ꢀ=ꢀ bis(4-(1H-imidazol-1-yl)phenyl)methanone)
with V-shaped BIPMO ligands, were synthesized and
characterized by IR spectroscopy and elemental analyses
along with their single-crystal X-ray diffraction analyses.
The Mn(II) ions in 1 and 2 are both six-coordinated to four
nitrogen atoms of four BIPMO ligands and two anions
(Cl− for 1, and SCN− for 2) to form a distorted octahedral
geometry.
Keywords: benzophenone; bidentate ligand; coordination novel V-shaped ligand bis(4-(1H-imidazol-1-yl)phenyl)
polymer; imidazole; N-donor ligands.
methanone (BIPMO), {[Mn(BIPMO)2Cl2] · 2(H2O)}n (1) and
{[Mn(BIPMO)2(SCN)2] · 2(CH3OH)}n (2) (Scheme 1).
1 Introduction
2 Results and discussion
Coordination polymers with various intriguing structural
motifs have been actively studied due to their potential
applications as chemical sensors, and in gas storage,
separation, luminescence, and catalysis [1–8]. An effec-
tive and facile method for the design of these complexes
2.1 Preparation and characterization of the
complexes
Complexes 1 and 2 were prepared as colorless crystalline
products via the combination of BIPMO with the metal
ion (MnCl2 for 1; MnCl2 and NH4SCN for 2). The complexes
are stable in common solvents such as benzene, hexane,
ethanol, and dichloromethane.
The structures of 1 and 2 were characterized by infra-
red (IR) spectroscopy, elemental analyses, single-crystal
X-ray diffraction, and thermogravimetry.
The IR spectra of 1 and 2 were consistent with their
formulation. Weak IR bands centered at ca. 3100 cm−1
can be assigned to ν(C–H) of the ligands. A large group
of bands in the region 1610–1430 cm−1 are characteristic
of ν(Cꢀ=ꢀN) and ν(Cꢀ=ꢀC) stretches of aromatic groups and
reveal the presence of ligands BIPMO.
a
Gao-Feng Wang and Xiao Zhang: These authors contributed equally
to this work.
*Corresponding authors: Gao-Feng Wang, Department of Applied
Chemistry, Yuncheng University, Yuncheng, 044000, P. R. China,
e-mail: wgf1979@126.com; and Xiao Zhang, MIIT Key Laboratory
of Critical Materials Technology for New Energy Conversion and
Storage, School of Chemistry and Chemical Engineering, Harbin
Institute of Technology, Harbin, 150080, P. R. China,
e-mail: zhangx@hit.edu.cn
Shu-Wen Sun, Hong Sun, Xia Yang, Hui Li, Chen-Zhong Yao,
Yu-Peng Tang and Li-Xin Meng: Department of Applied Chemistry,
Yuncheng University, Yuncheng, 044000, P. R. China
Shu-Gang Sun: Department of Technology and Service, Xichang
Satellite Launch Center, Xichang, 615000, P. R. China
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ꢀꢀꢀꢁ
870ꢀ
ꢀG.-F. Wang et al.: Synthesis of two Mn(II) coordination polymers
O
a Mn–N distance of 2.254(2) Å. The apical positions of the
octahedral geometry are occupied by two Cl anions with
a distance of 2.5943(8) Å. These parameters are similar to
those observed in other Mn(II) complexes [14–16]. Each
BIPMO ligand binds to two Mn(II) ions through the ter-
minal N atoms of the imidazole rings, resulting in closed
rings. The ring structure looks like a rhombus window of
approximate dimensions of 11.20 ꢀ×ꢀ 16.47 Å, and the dis-
tance between the two Mn(II) ions is 16.469(3) Å. These
subunits are linked by sharing the Mn(II) atoms with
adjacent subunits, together with the coordination of two
N
N
N
N
Scheme 1:ꢀMolecular formula of the ligand bis(4-(1H-imidazol-1-yl)
phenyl)methanone (BIPMO).
2.2 Molecular structures of 1 and 2
The crystal structure data are summarized in Table 1. Cl anions, to form the resultant infinite chain. The chain
Selected bond lengths and angles for 1 and 2 are listed in structure of 1 is further stabilized by C2–H2···Cl1 (C2···Cl1,
Table 2. The results of the single-crystal X-ray diffraction 3.146(3) Å; C2–H2···Cl1, 123°, symmetry codes: –x, –y, 1
analysis indicate that the structures of complexes 1 and – z) hydrogen bonds. It should be noted that each chain
2 are similar. Accordingly, the structure of 1 is described in compound 1 interacts with two neighboring chains via
representatively here in detail. Complex 1 crystallizes in weak C1–H1···O1 contacts (C1···O1, 3.275(3) Å; C1–H1···O1,
the monoclinic space group C2/m with Z ꢀ=ꢀ 2. The asym- 113°, symmetry codes: 1/2 – x, 1/2 – y, –z) along the crys-
metric unit contains one Mn(II) ion, two BIPMO ligands, tallographic b axis to form a 2D layer. The layer is stabi-
two Cl anions, and two uncoordinating water molecules. lized by C–H···π interactions between C3–H3 and the Cg1
As shown in Fig. 1, the basal plane around the Mn(II) ion is ring (C3···Cg1 ꢀ=ꢀ 3.648(3) Å, symmetry code: 1 – x, y, 1 – z)
formed by four nitrogen atoms of four BIPMO ligands with along the c axis to form a three-dimensional network (Cg1
Table 1:ꢀSummary of crystallographic data for complexes {[Mn(BIPMO)2Cl2] · 2(H2O)}n (1), and {[Mn(BIPMO)2(SCN)2] · 2(CH3OH)}n (2)
C38H28Cl2MnN8O2 (1) and C42H36MnN10O4S2 (2).
Compound
ꢁ
1
ꢁ
2
Empirical formula
Formula weight
T, K
ꢂ
ꢂ
ꢂ
C38H28Cl2MnN8O2 · 2H2Oꢂ
C40H28MnN10O2S2 · 2CH3OH
790.56
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
863.87
293(2)
293(2)
̅
Triclinic, P1
Crystal system; space group ꢂ
Monoclinic; C2/m
10.9985(5)
21.2104(6)
8.6611(4)
90
a, Å
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
9.5993(5)
9.6403(5)
11.3742(6)
85.235(5)
84.720(4)
82.353(4)
1036.11(10)
1
b, Å
c, Å
α, deg
β, deg
γ, deg
V, Å−3
Z
113.267(5)
90
1856.17(13)
2
D
calc., g cm−3
1.41
1.38
μ, mm−1
0.6
0.5
F (000), e
θ range, deg
814
447
3.20–25.49
–7, 13
2.92–25.35
–9, 11
h
min, hmax
min, kmax
min, lmax
k
l
–25, 24
–10, 10
–11, 11
–13, 13
Data/restraints/parameters ꢂ
Reflections collected/uniqueꢂ
1783/3/128
3700/1783
0.0248
3795/0/271
8099/3795
0.0280
Rint
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
Goodness-of-fit on F2
R1/wR2 [I ꢀ>ꢀ 2 σ(I)]
R1/wR2 (all data)
Largest peak/hole, e Å−3
1.035
1.055
0.0500/0.1452
0.0596/0.1523
0.94/–0.40
0.0509/0.1308
0.0687/0.1461
0.33/–0.46
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G.-F. Wang et al.: Synthesis of two Mn(II) coordination polymersꢃ
ꢃ871
Table 2:ꢀSelected bond lengths (Å) and bond angles (deg) for complexes 1 and 2.a
1
ꢁ
2
Mn(1)–N(1)
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
2.254(2)ꢂ
2.5943(8)ꢂ
2.5943(8)ꢂ
1.217(4)ꢂ
111.37(19)ꢂ
119.72(14)ꢂ
120.6(3)ꢂ
90.71(10)ꢂ
89.29(10)ꢂ
180ꢂ
Mn(1)–N(5)
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
2.236(3)
2.266(2)
2.270(2)
1.209(3)
180
91.51(9)
88.49(9)
91.51(9)
180
88.52(10)
91.48(10)
88.39(8)
91.61(8)
91.48(10)
88.52(10)
91.61(8)
88.39(8)
180
Mn(1)–Cl(1)
Mn(1)–N(1)#1
Mn(1)–Cl(1)#2
Mn(1)–N(4)#2
O(1)–C(10)
O(1)–C(10)
N(1)–C(1)–N(2)
N(5)–Mn(1)–N(5)#1
N(5)–Mn(1)–N(1)#1
N(5)–Mn(1)–N(1)
O(1)–C(10)–C(7)
C(7)–C(10)–C(7)#1
N(1)#2–Mn(1)–N(1)#3
N(1)#2–Mn(1)–N(1)#4
N(1)#3–Mn(1)–N(1)#4
N(1)#2–Mn(1)–N(1)
N(1)#3–Mn(1)–N(1)
N(1)#4–Mn(1)–N(1)
N(1)#2–Mn(1)–Cl(1)#2
N(1)#3–Mn(1)–Cl(1)#2
N(1)–Mn(1)–Cl(1)#2
N(1)–Mn(1)–Cl(1)
N(5)#1–Mn(1)–N(1) ꢂ
N(1)#1–Mn(1)–N(1) ꢂ
N(5)–Mn(1)–N(4)#2
N(5)#1–Mn(1)–N(4)#2
N(1)#1–Mn(1)–N(4)#2
N(1)–Mn(1)–N(4)#2
N(5)–Mn(1)–N(4)#3
N(5)#1–Mn(1)–N(4)#3
N(1)#1–Mn(1)–N(4)#3
N(1)–Mn(1)–N(4)#3
N(4)#2–Mn(1)–N(4)#3
C(1)–N(1)–Mn(1)
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
180ꢂ
89.30(10)ꢂ
90.70(10)ꢂ
87.33(5)ꢂ
92.67(5)ꢂ
92.67(5)ꢂ
87.33(5)ꢂ
180ꢂ
105.6(2)ꢂ
132.52(15)ꢂ
121.64(17)ꢂ
Cl(1)#2–Mn(1)–Cl(1) ꢂ
C(1)–N(1)–C(2)
C(1)–N(1)–Mn(1)
C(2)–N(1)–Mn(1)
ꢂ
ꢂ
ꢂ
128.6(2)
122.19(18)
127.0(2)
C(2)–N(1)–Mn(1)
C(17)–N(4)–Mn(1)#4
aFor 1: symmetry operations: #1 x, –y, z; #2 –x, –y, –z + 1; #3 –x, y, –z + 1; #4 –x + 1, y, –z; for 2: symmetry operations: #1 –x + 2, –y, –z + 1; #2 x + 1,
y – 1, z – 1; #3 –x + 1, –y + 1, –z + 2; #4 x – 1, y + 1, z + 1.
with Mn(II) in a distorted octahedral geometry (Figs. 3
and 4).
2.3 Thermal stability
Thermogravimetric analyses (TGA) were carried out for
complexes 1 and 2 in order to characterize the compounds
more fully in terms of thermal stability (Fig. 5). For complex
1, the weight loss corresponding to the release of free water
molecules is observed from 35 to 130°C (observed 5.0%, cal-
culated 4.55%). Then no significant weight loss is observed
Fig. 1:ꢀCoordination environments of complex 1. The hydrogen
until the decomposition of the frameworks occurs at 297°C.
atoms are omitted for clarity. Symmetry codes: #1 x, –y, z; #2 –x, –y,
For complex 2, the weight loss from 50 to 131°C is consist-
ent with the loss of two free methanol molecules (observed
7.2%, calculated 7.42%). The decomposition of the frame-
–z + 1; #3 –x, y, –z + 1; #4 –x + 1, y, –z.
is the ring comprising the atoms C4–C9 for both 1 and 2) works occurs from 315 to 606°C.
(Table 3, Fig. 2).
Compound 2 crystallizes in the triclinic space group,
̅
P1 with Z ꢀ=ꢀ 1. As shown in Fig. 3, the BIPMO ligands, such 3 Conclusions
as 1, connect the Mn(II) ions to generate similar rings of
approximate dimensions of 9.73 ꢀ×ꢀ 16.97 Å. The distance In this paper, we have reported the syntheses, crystal
between the two Mn(II) ions across the ring is longer structures, and characterization of two new Mn(II)
than that of 1, due to the rotation of an imidazole ring coordination polymers with the novel ligand BIPMO.
(Scheme 2). The N atoms coordinated with each Mn(II) The distances between the adjacent Mn(II) ions in the
ion come from four BIPMO ligands and two SCN− anions, chains are different due to the rotation of an imidazole
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872ꢀ ꢀG.-F. Wang et al.: Synthesis of two Mn(II) coordination polymers
Table 3:ꢀIntra- and intermolecular interactions for 1 and 2 (Å, deg).a
Complexꢁ
D–H···A
ꢁ
d(D–H)ꢁ
d(H···A)ꢁ
d(D···A)ꢁ
∠DHAꢁ
Symmetry operations
ꢂ
C1–H1···O1
C2–H2···Cl1
C3–H3···Cg1
C2–H2···O1
C2–H2···O1
C3–H3···O1
C5–H5···S1
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.93ꢂ
0.82ꢂ
0.96ꢂ
2.80ꢂ
2.81ꢂ
2.80ꢂ
2.83ꢂ
2.92ꢂ
2.69ꢂ
3.01ꢂ
3.36ꢂ
2.92ꢂ
2.77ꢂ
2.77ꢂ
2.99ꢂ
2.58ꢂ
2.90ꢂ
3.275(3)ꢂ
3.416(3)ꢂ
3.648(3)ꢂ
3.134(8)ꢂ
3.357(8)ꢂ
3.057(8)ꢂ
3.695(8)ꢂ
3.873(7)ꢂ
3.430(8)ꢂ
3.666(8)ꢂ
3.418(7)ꢂ
3.812(8)ꢂ
3.376(8)ꢂ
3.827(8)ꢂ
113ꢂ
123ꢂ
153ꢂ
100ꢂ
110ꢂ
104ꢂ
132ꢂ
117ꢂ
116ꢂ
161ꢂ
127ꢂ
149ꢂ
163ꢂ
161ꢂ
1/2 – x, 1/2 – y, –z
–x, –y, 1–z
1 – x, y, 1 – z
1 + x, y, z
1 – x, 1 – y, 1 – z
1 + x, y, z
1
2
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
ꢂ
x, 1 + y, z
x, 1 + y, z
C6–H6···S1
C13–H13···O2
C15–H15···O2
C17–H17···O2
C18–H18···O2
O2–H2A···S1
1 – x, 1 – y, 2 – z
x – 1, y – 2, z
1 – x, 1 – y, 2 – z
x – 1, y + 1, z
x, y, z
C21–H21A···Cg1ꢂ
x, y, z
aCg1 is the ring comprising the atoms C4–C9 for both 1 and 2.
Fig. 3:ꢀCoordination environments of complex 2. The hydrogen
atoms are omitted for clarity. Symmetry codes: #1 –x + 2, –y, –z + 1;
#2 x + 1, y – 1, z – 1; #3 –x + 1, –y + 1, –z + 2; #4 x – 1, y + 1, z + 1.
Fig. 2:ꢀA view of the chain in complex 1.
NETZSCH STA 449F3 unit at a heating rate of 10°C min−1
under a nitrogen–oxygen (80:20) atmosphere.
ring. Hydrogen bonds and weak C–H···π interactions in
the crystals link the chains to form 3D supramolecular
structures.
4.2 Synthesis of bis(4-(1H-imidazol-1-yl)
phenyl)methanone
A mixture of imidazole (3.40 g, 50 mmol), anhydrous
potassium carbonate (6.90 g, 100 mmol), 4,4′-difluorodi-
phenylmethanone (5.45 g, 25 mmol), hexadecyltrimethyl-
ammonium bromide (50 mg), and dimethyl sulphoxide
(30.0 mL) was stirred for a period of 24 h at 80°C and, after
4 Experimental section
4.1 Materials and measurements
All solvents, MnCl2·4H2O, and NH4SCN were purchased cooling to room temperature, was poured into crushed ice
from Aladdin Industrial Corporation (Shanghai, China). (100 mL). Pale yellow precipitates obtained were filtered,
Elemental analyses were performed on an Elementar Vario washed with distilled water, and dried in air. Yield: 95.6%.
ELIII elemental analyzer. The IR spectra were recorded on – Anal. for C19H14N4O: calcd. C 72.60, H 4.49, N 17.82; found
a Bruker Vector 22 spectrophotometer with KBr pellets C 72.47, H 4.38, N 17.74%. – 1H NMR (500 MHz, CDCl3) δ 8.00
in the 4000–400 cm−1 region. TGA were carried out on a (s, 1H, imidazole-H), 7.99–7.57 (m, 4H, Ar-H), 7.41 (s, 1H,
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O
O
N
N
N
N
N
N
N
N
Mn
Mn
Mn
Scheme 2:ꢀLigand coordination modes in complexes 1 (left) and 2(right).
Mn
Fig. 4:ꢀA view of the chain in complex 2.
imidazole-H), 7.29 (s, 1H, imidazole-H). – IR (KBr, cm−1): methanol (10 mL) was layered over the buffer layer. Color-
3124, 1639, 1599, 1573, 1519, 1481, 1421, 1369, 1325, 1301, less block crystals were obtained after a week. Yield: 65%
1261, 1180, 1148, 1109, 1055, 956, 926, 899, 860, 831, 766, (based on BIPMO). – Anal. for C38H32Cl2MnN8O4: calcd. C
746, 662, 622, 519, 473.
57.73, H 4.08, N, 14.17; found: C 57.51, H 3.91, N 14.04%. – IR
(cm−1): 3124, 3083, 1659, 1603, 1556, 1520, 1488, 1470, 1421,
1321, 1306, 1265, 1238, 1176, 1119, 1057, 958, 928, 856, 768,
739, 719, 673, 654, 620, 523, 469.
4.3 Synthesis of {[Mn(BIPMO)2Cl2] ·
2(H2O)}n (1)
4.4 Synthesis of {[Mn(BIPMO)2(SCN)2] ·
2(CH3OH)}n (2)
Complex 1 was prepared by a layering method. A buffer
solution (5 mL) of methanol was carefully layered over
a methanol solution (5 mL) of MnCl2·4H2O (19.8 mg, 0.1
mmol). Then a solution of BIPMO (62.8 mg, 0.2 mmol) in
A buffer solution (5 mL) of methanol was carefully layered
over a methanol solution (5 mL) of MnCl2·4H2O (19.8 mg, 0.1
mmol) and NH4SCN (15.2 mg, 0.2 mmol). Then a solution
of BIPMO (62.8 mg, 0.2 mmol) in methanol (10 mL) was
layered over the buffer layer. Colorless block crystals were
obtained after 1 week. Yield: 68% (based on BIPMO). –
Anal. for C42H36MnN10O4S2: calcd. C 58.39, H 4.20, N 16.21;
found: C 58.16, H 4.08, N 16.04%. – IR (cm−1): 3141, 2073,
1657, 1637, 1606, 1522, 1490, 1402, 1304, 1284, 1256, 1188,
1119, 1061, 959, 928, 853, 819, 766, 737, 652, 516, 475.
100
80
60
40
20
0
1
2
4.5 X-ray crystallography
0
100 200 300 400 500 600 700 800
Temperature / °C
All measurements were made on an Agilent Technology
SuperNova Eos Dual system with a (MoKα, λ ꢀ=ꢀ 0.71073 Å)
Fig. 5:ꢀTGA curves for complexes 1 and 2.
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[3] J.-R. Li, R. J. Kuppler, H.-C. Zhou, Chem. Soc. Rev. 2009,
38, 1477.
[4] M. D. Allendorf, C. A. Bauer, R. K. Bhakta, R. J. T. Houk, Chem.
Soc. Rev. 2009, 38, 1330.
[5] M. P. Suh, Y. E. Cheon, E. Y. Lee, Coord. Chem. Rev. 2008, 252,
1007.
[6] Z. Hu, B. J. Deibert, J. Li, Chem. Soc. Rev. 2014, 43, 5815.
[7] J. S. Seo, D.Whang, H. Lee, S. I. Jun, J. Oh, Y. J. Jeon, K. Kim,
Nature 2000, 404, 982.
[8] A. Dhakshinamoorthy, H. Garcia, Chem. Soc. Rev. 2014, 43,
5750.
[9] D. Singh, J. B. Baruah, Cryst. Growth Des. 2012, 12, 3169.
[10] B.-C. Tzeng, A. Chao, T. Selvam, T.-Y. Chang, CrystEngComm
2013, 15, 5337.
[11] G.-F. Wang, Q.-J. Gong, H. Sun, C.-Z. Yao, Crystallogr. Rep. 2013,
58, 1113.
micro focus source and focusing multilayer mirror optics.
The data were collected at a temperature of 293 K and
processed using CrysAlis Pro [17]. Absorption correc-
tions were applied using the SADABS program [18]. The
structures were solved by Direct Methods [19] with the
Shelxtl (version 6.10) program [19, 20] and refined by
full matrix least-squares techniques on F2 with Shelxtl
[19, 20]. All non-hydrogen atoms were refined anisotropi-
cally. The ligand hydrogen atoms were localized in their
calculated positions and refined using a riding model. The
water hydrogen atoms were located in difference maps and
refined with d(O–H) ꢀ=ꢀ 0.85(2) Å and d(H···H) ꢀ=ꢀ 1.35(2) Å
distances as restraints.
CCDC 1439673 and 1439674 contain the supplemen-
tary crystallographic data for this paper. These data
can be obtained free of charge from The Cambridge
Crystallographic Data Centre via www.ccdc.cam.ac.uk/
data_request/cif.
[12] R. A. Agarwal, A. Aijaz, M. Ahmad, E. C. Sañudo, Q. Xu, P. K.
Bharadwaj, Cryst. Growth Des. 2012, 12, 2999.
[13] L. Luo, P. Wang, G.-C. Xu, Q. Liu, K. Chen, Y. Lu, Y. Zhao, W.-Y.
Sun, Cryst. Growth Des. 2012, 12, 2634.
[14] H.-F. Zhu, W. Zhao, T. Okamura, J. Fan, W.-Y. Sun, N. Ueyama,
New J. Chem. 2004, 28, 1010.
[15] X.-L. Mu, Acta Crystallogr. 2011, E67, m166.
[16] L. Ballester, I. Baxter, P. C. M. Duncan, D. M. L. Goodgame, D. A.
Grachvogel, D. J. Williams, Polyhedron 1998, 17, 3613.
[17] CrysAlis Pro Software System (version 1.171.35.19), Intelligent
Data Collection and Processing Software for Small Molecule
and Protein Crystallography, Agilent Technologies Ltd., Yarn-
ton, Oxfordshire (U.K.) 2011.
Acknowledgments: We are grateful for financial support
from Young Teacher Starting-up Research of Yuncheng
University (No. YQ-2015007 to G-FW) and the National
Natural Science Foundation of China (No. 51108122 to XZ
and 21576230 to C-ZY).
[18] G. M. Sheldrick, Sadabs, Program for Empirical Absorption
Correction of Area Detector Data, University of Göttingen, Göt-
tingen (Germany) 1996.
References
[1] Y. He, W. Zhou, G. Qian, B. Chen, Chem. Soc. Rev. 2014, 43, 5657.
[2] S. Ma, D. Sun, J. M. Simmons, C. D. Collier, D. Yuan, H.-C. Zhou,
J. Am. Chem. Soc. 2008, 130, 1012.
[19] G. M. Sheldrick, Shelxtl (version 6.1), Software Reference
Manual, Bruker Analytical X-ray Instruments Inc., Madison, WI
(USA) 2000.
[20] G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.
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