Synthesis, crystal structure, weak interactions, spectra and magnetic behavior of a new ion-pair complex containing bis(maleonitriledithiolato) nickel(III) monoanion and substituted isoquinolinium cation

Article abstract of DOI:10.1080/15533170903129729

A new ion-pair complex, [BrClBzIQl][Ni(mnt)2](1) ([BrClBzIQl]+ = 1-(2' -chloro-4' -bromobenzyl)isoquinolinium, and mnt2- = maleonitriledithiolate) has been prepared and characterized by elemental analyses, IR, MS spectra, single crystal X-ray diffraction

Full text of DOI:10.1080/15533170903129729

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Synthesis, Crystal Structure, Weak
Interactions, Spectra and Magnetic Behavior
of a New Ion-pair Complex Containing
Bis(maleonitriledithiolato)nickel(III) Monoanion and
Substituted Isoquinolinium Cation
Xiao-Mei Zhuang a , Yu-Wen Liang b , Hong-Rong Zuo b , Qian Huang b , Lin-Liang Yu b ,
Le-Min Yang b & Chun-Lin Ni b
a Zhongshan Polytechnic , Zhongshan, Guangdong, P. R. China
b Department of Applied Chemistry, Centre of Inorganic Functional Materials , South
China Agricultural University , Guangzhou, P. R. China
Published online: 11 Aug 2009.
To cite this article: Xiao-Mei Zhuang , Yu-Wen Liang , Hong-Rong Zuo , Qian Huang , Lin-Liang Yu , Le-Min Yang & Chun-
Lin Ni (2009) Synthesis, Crystal Structure, Weak Interactions, Spectra and Magnetic Behavior of a New Ion-pair Complex
Containing Bis(maleonitriledithiolato)nickel(III) Monoanion and Substituted Isoquinolinium Cation, Synthesis and Reactivity
in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 39:7, 388-393
To link to this article: http://dx.doi.org/10.1080/15533170903129729
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 39:388–393, 2009
Copyright © Taylor & Francis Group, LLC
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533170903129729
Synthesis, Crystal Structure, Weak Interactions, Spectra and
Magnetic Behavior of a New Ion-pair Complex Containing
Bis(maleonitriledithiolato)nickel(III) Monoanion and
Substituted Isoquinolinium Cation
Xiao-Mei Zhuang,1 Yu-Wen Liang,2 Hong-Rong Zuo,2 Qian Huang,2
Lin-Liang Yu,2 Le-Min Yang,2 and Chun-Lin Ni2
1Zhongshan Polytechnic, Zhongshan, Guangdong, P. R. China
2Department of Applied Chemistry, Centre of Inorganic Functional Materials, South China Agricultural
University, Guangzhou, P. R. China
(M Ni(III), Pd(III) or Pt(III) ion) anion as a building
block for self-assembly is its ability to form 1D, 2D or 3D
molecular materials with unusual magnetic properties. In
recent years, we have developed a new class of ion-pair
complex, [RBzPy][Ni(mnt)2] (RBzPy+ = benzylpyridinium
derivative) and found that the significant structural feature
of these molecular solids is that the [Ni(mnt)2]− anions and
[RBzPy]+ cations stack into well-segregated columns in
the solid state, and [Ni(mnt)2]− anions may form ideal 1D
A
new
ion-pair
complex,
[BrClBzIQl][Ni(mnt)2](1)
([BrClBzIQl]+ = 1-(2ꢀ -chloro-4ꢀ -bromobenzyl)isoquinolinium,
and mnt2− = maleonitriledithiolate) has been prepared and
characterized by elemental analyses, IR, MS spectra, single crystal
X-ray diffraction and magnetic susceptibility. The crystals are
˚
˚
˚
monoclinic space group, Cc, a = 9.249(3) A, b = 18.312(5) A, c =
◦
3
˚
32.062(9) A, β = 90.92(1) , V = 5430(3) A , Z = 4. The Ni(III)
. . .
˚
ions of 1 form a dimer with Ni Ni distance being 4.332 A through
. . .
. . .
. . .
. . .
short Ni S and S S interactions. The weak anion-cation π
stacking interactions, C H N hydrogen bonds and short Ni
π
N
. . .
. . .
magnetic chains of s = 1/2 through intermolecular Ni S,
[6−8]
interactions further generate a 3D network structure. Magnetic
susceptibility measurement in the temperature range 2–300 K
shows that 1 exhibits antiferromagnetic behavior with g = 2.02,
. . .
. . .
. . .
S
S, Ni Ni or π π interactions.
These molecular
solids exhibit versatile magnetic properties such as ferro-
magnetic ordering, magnetic transition from ferromagnetic
to diamagnetic coupling, meta-magnetism, spin gap and
spin-Peierls-like transitions.[6−8] The structure of isoquinoline
is similar to pyridine, while its electronic conjugating system
is larger than that of the latter. Therefore, we have introduced
substituted benzylisoquinolinium into the system containing
[Ni(mnt)2]− anion and obtained several ion-pair complexes, as
exemplified by [BzIQl][Ni(mnt)2],[9] [ClBzIQl][Ni(mnt)2],[9]
J = −373.3 cm−1
.
Keywords crystal structure, magnetic property, maleonitriledithio-
late, nickel, substituted isoquinolinium, weak interactions
INTRODUCTION
The coordination chemistry of maleonitriledithiolate (mnt)
has been extensively developed for several decades,[1] mostly
in view of the significance of the corresponding complexes
in well-established areas of materials and supramolecular
chemistry.[2−5] One of the advantages of using [M(mnt)2]−
[OFBzIQl][Ni(mnt)2],[10]
[BrFBzIQl][Ni(mnt)2][11]
and
[NO2BzIQl][Ni(mnt)2],[12] which exhibit versatile magnetic
properties. In order to widen the research in this aspect, in
this work, a new ion-pair complex, [BrClBzIQl][Ni(mnt)2](1),
has been prepared and characterized by elemental analyses,
IR, MS spectra, single crystal X-ray diffraction and magnetic
susceptibility.
Received 15 March 2009; accepted 26 April 2009.
The authors thank the Science and Technology Project
(No.2008B080703005) from Guangdong Science and Technology De-
partment and the President’s Science Foundation of South China Agri-
cultural University (No.2008X015) for financial support of this work.
Address correspondence to Prof. Chun-Lin Ni, Dept. of Applied
Chemistry, College of Science, Centre of Inorganic Functional Mate-
rials, South China Agricultural University, Guangzhou, 510642, P. R.
China. E-mail: ctgunicl@163.com
EXPERIMENTAL
Materials and Physical Measurements
The starting materials, 1-(2ꢀ -chloro-4ꢀ -bromobenzyl)-iso-
quinolinium ([BrClBzIQl]Br) and disodium maleonitriledithi-
olate (Na2mnt) were synthesized following the literature
388

BEHAVIOR OF A NEW ION-PAIR COMPLEX
389
TABLE 1
Crystallographic data and structure refinement parameters of 1
TABLE 2
◦
˚
Selected bond distances (A) and angles ( ) of 1
˚
Empirical formula
Formula weight
Crystal system
Space group
C50H27Br2Cl2N11Ni2S8
1386.45
Monoclinic
Cc
9.249(3)
18.312(5)
32.062(9)
90
90.92(1)
90
5430(3)
4
1.696
2.620
2768
Bond
Distances (A)
Bond
Angles (◦)
Ni(1)−S(1)
Ni(1)−S(2)
Ni(1)−S(3)
Ni(1)−S(4)
Ni(2)−S(5)
Ni(2)−S(6)
Ni(2)−S(7)
Ni(2)−S(8)
S(1)−C(2)
S(2)−C(3)
S(3)−C(6)
S(4)−C(7)
S(5)−C(10)
S(6)−C(11)
S(7)−C(14)
S(8)−C(15)
2.139(2)
2.128(2)
2.128(2)
2.136(2)
2.132(2)
2.132(2)
2.135(2)
2.137(2)
1.699(7)
1.733(7)
1.695(8)
1.701(9)
1.709(8)
1.718(8)
1.685(8)
1.691(7)
S(1)−Ni(1)−S(2)
S(1)−Ni(1)−S(4)
S(2)−Ni(1)−S(3)
S(3)−Ni(1)−S(4)
S(5)−Ni(2)−S(6)
S(5)−Ni(2)−S(8)
S(6)−Ni(2)−S(7)
S(7)−Ni(2)−S(8)
92.81(8)
87.33(8)
87.28(8)
92.63(9)
92.64(9)
86.63(8)
88.07(8)
92.66(8)
˚
a (A)
˚
b (A)
˚
c (A)
α (◦)
β (◦)
γ (◦)
V (A )
Z
Ni(1)−S(1)−C(2) 102.6(3)
Ni(1)−S(2)−C(3) 102.8(3)
Ni(1)−S(3)−C(6) 103.4(3)
Ni(1)−S(4)−C(7) 103.5(3)
Ni(2)−S(5)−C(10) 102.9(3)
Ni(2)−S(6)−C(11) 103.2(3)
Ni(2)−S(7)−C(14) 102.8(3)
Ni(2)−S(8)−C(15) 103.4(3)
3
˚
Dcalc (g/cm3)
µ (mm−1
F (000)
)
Diffractometer
Bruker SMART APEX CCD
0.71073
291 (2)
˚
Wavelength (A)
Temperature (K)
θ Range for data
collection (◦)
2.22 – 25.00
Index ranges
−10 ≤ h ≤ 10, −16 ≤ k ≤ 21,
−37 ≤ l ≤ 38
Synthesis of the Title Complex
[BrClBzIQl]2[Ni(mnt)2] (1.0 g, 1.0 mmol) was solved in 50
cm3 MeCN, then a MeCN solution (10 cm3) of I2 (0.150 g,
0.59 mmol) was slowly added, the mixture was stirred for 12
h at room temperature, and then 60 cm3 CH3OH was added.
After the mixture was allowed to stand overnight, 0.58 g dark-
red crystals produced were filtered off, washed with CH3OH
and Et2O and dried in a vacuum. Yield: 83.7%. Anal. calc. for
C50H27Br2Cl2N11Ni2S8: C, 43.31; H, 1.96; N, 11.11. Found: C,
43.37; H, 2.02; N, 11.05%. IR (cm−1): 3094s, 2983w, 2935w,
2207s, 1641s, 1609s, 1587s, 1561s, 1541s, 1470s, 1436s, 1397s,
1160s, 868w, 819s, 761s, 502s. Single crystals suitable for X-
ray structure analyses were obtained by evaporating solution of
1 in mixed solution of MeCN and i-PrOH (1:2 v/v) at room
temperature.
Reflection collected
Unique reflections
Refinement method
Max. and min. transition
Data / restrains /
parameters
13215
8499 (Rint = 0.054)
Full-matrix least-squares on F2
0.661 and 0.481
8499 / 6471 /677
Final R indices [I > 2σ
(I)]
R1 = 0.0495, wR2 = 0.1064
R indices (all data)
R1 = 0.0686, wR2 = 0.1104
Goodness of fit on F2
1.031
Largest diff. peak and hole 0.588 and −0.374
–3
˚
(e A
)
procedures.[13,14] Other solvents and reagents were purchased
commercially and used without further purification. A simi-
lar method for preparing [BzIQl]2[Ni(mnt)2] was utilized to
X-ray Crystallography
Diffraction intensities for the title ion-pair complex were col-
prepare [BrClBzIQl]2[Ni(mnt)2].[9] Elemental analysis was run lected at 291(2) K using a Bruker SMART APEXII CCD area-
˚
on a Model 240C Perkin-Elmer C H N instrument. IR spec- detector with MoKα radiation (λ = 0.71073 A). The collected
trum was recorded on an IF66V FT-IR (400–4000 cm−1 region) data were reduced using the SAINT program,[15] and multi-
spectrophotometer in KBr pellet. The electrospray mass spec- scan absorption correction was performed using the SADABS
trum [ESI-MS] was determined on a Finnigan LCQ mass spec- program.[16] The structure was solved by direct method and
trograph, sample concentration ca.1.0 mmol dm−3. Magnetic refined against F2 by full-matrix least-squares method using
susceptibility data on crushed polycrystalline sample of 1 were the SHELXTL program.[17] All non-hydrogen atoms were re-
collected over the temperature range of 2–300 K using a Quan- fined with anisotropic thermal parameters. All H atoms were
tum Design MPMS-5S superconducting quantum interference positioned geometrically, and constrained to ride on their parent
device (SQUID) magnetometer, and the experimental data were atoms with Hiso(H) = 1.2 Ueq (C). The crystallographic data for
corrected for diamagnetism of the constituent atoms estimated the complex are summarized in Table 1. Selected bond lengths
from Pascal’s constants.
and angles of the complex are listed in Table 2. Crystallographic

390
X.-M. ZHUANG ET AL.
FIG. 1. ORTEP plot (30% probability ellipsoids) showing the molecule structure of 1.
data for the complex has been deposited with the Cambridge [BrClBzIQl][Ni(mnt)2](1), was prepared by I2 oxidation of the
Crystallographic Data Centre (CCDC 723804).
Ni(II) complex, and well-shaped black-red single crystals suit-
able for X-ray structure analyses were obtained by evaporating
solution of the complex in mixtures of MeCN and i-PrOH.
Elemental analysis, IR and EI-MS spectra are consistent with
formulation of the title ion-pair complex. Bands at 3094, 2983
and 2935 cm−1 are due to the stretching vibration frequencies
of C-H in the aromatic rings and the methylene. The complex
RESULTS AND DISCUSSION
Synthesis, Infrared Spectrum and Electrospray Mass
Spectrum
The Ni(II) complex of the title complex was simply syn- 1 shows one strong band at 2207 cm−1, which is C≡N stretch-
thesized by the direct reaction of Na2mnt, NiCl2· 6H2O and ing band.[18] Bands at 1641, 1609, 1587, and 1560 cm−1 are
[BrClBzIQl]Br in a methanol solution. The title complex, attributable to ν (C N) and ν (C C) stretching vibration
. . .
. . .
. . .
. . .
. . .
FIG. 2. Short anion-anion Ni S and S S interactions, and anion-anion π π stacking interactions, C-H N hydrogen bonds and short Ni N interactions.

BEHAVIOR OF A NEW ION-PAIR COMPLEX
391
FIG. 3. The overlapping patterns of two neighboring [Ni(mnt)2]− anions.
by the phenyl and isoquinoline rings is 77.0◦. For [BrClBzIQl]+
cation containing N(10) atom, the deviations of Br and Cl atoms
bands for the phenyl and isoquinoline rings. The ν (C C) band
of mnt2− is at 1436 cm−1 [18] Bands at 761 and 502 cm−1 are
.
˚
˚
attributable to the C-Cl and C-Br stretching vibration bands,
respectively. The negative-ion and positive-ion ESI-MS spectra
in a MeCN solution show that the mass spectrum dominated by
the 339.9 peak, which is due to [Ni(mnt)2]− , and peak at 334.1
is assigned to [BrClBzIQl]+ cation.
from the phenyl ring plane are 0.058 A for Br(1) and 0.028 A
for Cl(1). The dihedral angles that phenyl ring and isoquinoline
plane make with the N(10)−C(42)−C(43) reference plane are
11.2◦ and 71.6◦, and the dihedral angle between the phenyl
and isoquinoline rings is 76.7◦. As shown in Figure 2, two
[Ni(mnt)2]− anions form a dimer with Ni(1) Ni(2) distance
. . .
. . . . . .
˚
being 4.332 A through intermolecular short Ni S and S
. . . . . . . . .
S
Description of the Crystal Structure
interactions, and the Ni(1) S(8), Ni(2) S(2), S(1) S(8)
. . .
˚
Compound 1 crystallizes in a monoclinic lattice, and the
unit cell contains two [BrClBzIQl]+ cations, two [Ni(mnt)2]−
anions and one acetonitrile molecule (Figure 1). The mononu-
clear nickel(III) coordinated by is four S atoms exhibits the
approximate planar square geometry. The Ni−S band distances
and the S-Ni-S bond angles (Table 2) within the five-membered
rings are agreement well with those found in the solids based
on [Ni(mnt)2]− anion comprised of other substituted ben-
zylisoquinolinium derivatives.[9−12] For [BrClBzIQl]+ cation
containing N(9) atom, the deviations of Br and Cl atoms from
and S(2) S(7) distances are 3.720, 3.732, 3.558 and 3.556 A,
respectively. The overlap mode of the adjacent anions is shown
in Figure 3. It is noting that three weak interactions between
the [Ni(mnt)2]− anions and [BrClBzIQl]+ cations are observed
. . .
. . .
Figure 2: (1) short Ni N interactions with Ni(1) N(10A) and
. . .
. . .
˚
Ni(2) N(9) distances being 3.526 and 3.528 A, respectively;
˚
(2) π π stacking interaction with a distance of 3.510 A
between the isoquinoline ring and the Ni(1)S(3)S(4)C(6)C(7)
−
˚
plane of [Ni(mnt)2] anion, and 3.501 A between the isoquino-
line ring and the Ni(2)S(5)S(6)C(10)C(11) plane of [Ni(mnt)2]−
anion (the dihedral angle between the two rings is 1.9◦); (3) six
˚
˚
the phenyl ring plane are 0.009 A for Br(2) and −0.025 A for
Cl(2). Both the phenyl and isoquinoline rings are twisted to the
N(9)−C(26)−C(27) reference plane, and the dihedral angles
that phenyl ring and isoquinoline plane make with the reference
plane are 7.9◦ and 73.8◦, respectively. The dihedral angle defined
. . .
C-H N hydrogen bonds and the responding bond parameters
listed in Table 3. The effect of the combination of weak inter-
actions in the crystal further generates a 3D network structure
(Figure 4).
TABLE 3
Weak hydrogen bonds for 1 (A and )
◦
˚
. . .
D-H
. . .
. . .
A
d(D-H) d(H A) d (D A) <(DHA)
. . .
C(25)-H(25) N(1)#1
0.930
0.970
0.970
0.930
0.970
0.960
2.570
2.410
2.580
2.600
2.580
2.520
3.408(13)
3.358(11)
3.292(11)
3.421(11)
3.281(12)
3.226(19)
149.0
167.0
131.0
147.0
130.0
130.0
. . .
C(26)-H(26A) N(2)#2
. . .
C(26)-H(26B) N(1)#1
. . .
C(41)-H(41) N(7)#1
. . .
C(42)-H(42A) N(7)#1
. . .
C(50)-H(50C) N(5)#2
Symmetry transformations used to generate equivalent atoms: #1 = x – 1/2,
y+ 1/2, z; #2 = x − 1, y, z.

392
X.-M. ZHUANG ET AL.
FIG. 4. The packing diagram of 1 as viewed along a axis.
Magnetic Property
dinuclear model approximation (the Hamiltonian being H =
2JSASB ) (Equation 1):[19]
The temperature dependence of the magnetic susceptibility
for 1 is measured under an applied field of 2000 Oe in tempera-
ture range 2–300 K. The plot of χmT versus T for 1 is shown in
χm = (2Nβ2g2/kT )(1 − ρ)/(3 + exp(−2J/kT ))
Figure 5. At 300 K, the χmT values of 1 is 0.080 emu K mol−1
,
+ (Nβ2g2/2kT )ρ
[1]
which is markedly less than the calculated spin-only value of
0.375 emu K mol−1 for a system comprised of non-interacting
g = 2, S = 1/2 spin site indicating that a significant antiferro-
magnetic coupling contribution is involved. When the system
cools down, the value of χmT decreases quickly to 4.21 × 10−3
emu K mol−1 at 150 K, and slowly drops to zero at 2 K. The
magnetic susceptibility data of 1 can be analysed using simple
where N, g, k, β and ρ have their usual meanings, and J is
the exchange coupling parameter describing the magnetic in-
teraction between any two neighbouring S = 1/2 spins. The
best-fit parameters obtained by least-squares fit are: g = 2.02,
J = −373.3 cm−1, ρ = 2.0 × 10−3 and R = 2.9 × 10−6(R
is defined as ꢀ(χmT−calcd − χmTobsd)2/ꢀ(χmTobsd)2). The low
ρ value suggests that the paramagnetic impurities have little
effect on the magnetic measurement for 1. The model provides
an excellent fit (see the solid lines in Figure 5), as indicated by
the low value of R.
CONCLUSION
In
the
presented
new
ion-pair
complex,
[BrClBzIQl][Ni(mnt)2](1) ([BrClBzIQl]+ = 1-(2ꢀ-chloro-4ꢀ
-bromobenzyl)isoquinolinium, and mnt2− = maleonitriledithi-
. . .
olate), the Ni(III) ions form a dimer with Ni Ni distance
. . .
. . .
˚
being 4.332 A through short Ni S and S S interactions.
. . .
The weak anion-cation π
. . .
π stacking interactions, C-
. . .
H
N hydrogen bonds and short Ni N interactions further
generate a 3D network structure. Magnetic susceptibility
measurements in the temperature range 2–300 K show that
FIG. 5. Plots of χ mT versus T for 1. The solid line is reproduced from the
theoretic calculations and detailed fitting procedure described in the text.

BEHAVIOR OF A NEW ION-PAIR COMPLEX
393
1 exhibits antiferromagnetic behavior with g = 2.02, J =
containing one-dimensional Ni(III) chain. Chem. Phys. Lett. 2004, 396,
353–358.
9. Ni, C.L., Tian, Z.F., Ni, Z.P., Dang, D.B., Li, Y.Z., Song, Y., and Meng, Q.J.
Syntheses, crystal structures, and magnetic properties of Ni(mnt)2-based
molecular solids containing substituted isoquinolinium. Inorg. Chim. Acta
2006, 359, 3927–3933.
−373.3 cm−1
.
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