A novel cyano-bridged heteronuclear complex exhibiting C-H?Ni close interaction: [Cd(C4H7N)2Ni(μ-CN) 4]n

Article abstract of DOI:10.1016/j.molstruc.2011.02.046

The cyano-bridged heteronuclear polymeric complex, [Cd(pyr) ₂Ni(μ-CN)₄]_n, 1 (pyr = 3-pyrroline or 2,5-dihydropyrrole), has been synthesized and characterized by FT-IR, Raman spectroscopy, thermal and elemental analyses. The crystal structure of 1 has been determined by X-ray single crystal diffraction. The complex crystallizes in orthorhombic system and space group Pmna. In 1, Ni(II) ion is coordinated by four cyano ligands, and the Cd(II) ion is coordinated by four bridging cyanide ligands and two trans pyr ligands. The coordination environment of the Cd(II) ion described as distorted octahedral geometry, whereas around the Ni(II) centre has square planar geometry. The crystallographic analysis reveals that the weak intermolecular C-H?Ni interaction was found to be hydrogen bonding interaction, resulting in a 3D framework. Vibration assignments were given for all the observed bands and the spectral feature also supported to the structure of polymeric complex. The decomposition reaction take places in the temperature range 30-700 °C in the static air atmosphere.

Full text of DOI:10.1016/j.molstruc.2011.02.046

Journal of Molecular Structure 994 (2011) 39–43
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: www.elsevier.com/locate/molstruc
A novel cyano-bridged heteronuclear complex exhibiting C–HꢀꢀꢀNi close
interaction: [Cd(C H N) Ni(l-CN) ]
4
7
2
4 n
a,
⇑
b
c
d
_
Güne ßs Süheyla Kürkçüo g˘ lu , Okan Zafer Ye sß ilel , Ilkay Çaylı , Orhan Büyükgüngör
a
Eski ßs ehir Osmangazi University, Faculty of Arts and Sciences, Department of Physics, TR-26480 Eski ßs ehir, Turkey
Eski ßs ehir Osmangazi University, Faculty of Arts and Sciences, Department of Chemistry, TR-26480 Eski ßs ehir, Turkey
Eski ßs ehir Osmangazi University, Graduate School of Science, TR-26480 Eski ßs ehir, Turkey
Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, TR-55139 Samsun, Turkey
b
c
d
a r t i c l e i n f o
a b s t r a c t
Article history:
The cyano-bridged heteronuclear polymeric complex, [Cd(pyr) Ni(
l
-CN) ] , 1 (pyr = 3-pyrroline or 2,5-
2
4 n
Received 29 December 2010
Received in revised form 22 February 2011
Accepted 22 February 2011
Available online 26 February 2011
dihydropyrrole), has been synthesized and characterized by FT-IR, Raman spectroscopy, thermal and ele-
mental analyses. The crystal structure of 1 has been determined by X-ray single crystal diffraction. The
complex crystallizes in orthorhombic system and space group Pmna. In 1, Ni(II) ion is coordinated by four
cyano ligands, and the Cd(II) ion is coordinated by four bridging cyanide ligands and two trans pyr
ligands. The coordination environment of the Cd(II) ion described as distorted octahedral geometry,
whereas around the Ni(II) centre has square planar geometry. The crystallographic analysis reveals that
the weak intermolecular C–HꢀꢀꢀNi interaction was found to be hydrogen bonding interaction, resulting in
a 3D framework. Vibration assignments were given for all the observed bands and the spectral feature
also supported to the structure of polymeric complex. The decomposition reaction take places in the tem-
perature range 30–700 °C in the static air atmosphere.
Keywords:
Cyano-bridged complex
Tetracyanonickelate(II) complex
C–HꢀꢀꢀNi interaction
FT-IR and Raman spectra
Crystal structure analysis
3
-Pyrroline,2,5-dihydropyrrole
Ó 2011 Elsevier B.V. All rights reserved.
1
. Introduction
The field of transition metal cyanide chemistry has a remark-
using N-donor ligands 2-methylpyrazine [13], triethylenetetra-
mine [14,15], 2-aminomethylpyridine [16]. The Hofmann-type
4 n
host framework is formed from infinite {M–Ni(CN) } layers with
able history that spans almost three centuries, dating back to the
earlier 18th century. The wide availability of cyano complexes to-
gether with their diverse bonding and structural chemistry has led
to their widespread applications in the field of material chemistry
four planar coordination around Ni atom [17].
Non-covalent interactions are very important in biological
structure, supramolecular chemistry and molecular recognition.
When a C–H bond of transition metal ligands is oriented towards
the metal ion, indicating some weak interaction between the metal
and the H atom, this has been considered as an intramolecular
hydrogen bonding. The most interesting feature of this structure
is the C–HꢀꢀꢀNi hydrogen bonding interaction. These weak interac-
tions have facilitated the formation of the coordination bond
between Cd(II) and the N donor of the pyr ligands. These intermo-
lecular interactions give three-dimensional framework.
[
1]. Functional polymeric cyano complexes can be prepared with
two or more dentate ligands. These types of materials are packed
to form crystal structures due to bridging groups and intermolecu-
lar interactions [2]. Tetracyanonickelate complexes [3,4] have
2ꢁ
nitrogens in the square [Ni(CN)
4
]
anion to form additional coor-
dination bonds enhancing dimensionality of the structure [4,5].
The ability of the tetracyanonickelate anion to form oligo- and
polynuclear compounds was mainly exploited in connection with
their ability to form Hofmann-type and analogous clathrates [6].
Tetracyanonickelates exhibiting especially low-dimensional struc-
tures for magnetic applications attract the interest of chemists and
As faras weknow, novibrationaland structural studieshavebeen
reported for the transition metal(II)-cyano complexes with pyr li-
gand. Here we report the results of our study on synthesis, chemical,
spectral and structural characterization of one novel cyano-bridged
physicists [7–9].
heteronuclear polymeric complex, [Cd(pyr)
. Experimental
.1. Materials and instrumentation
Cd(II) chloride (CdCl ), potassium cyanide (KCN) and 3-pyrroline
2 4 n
Ni(l-CN) ] (1).
0
The Hofmann-type compounds [ML
2
M (CN)
4
]
n
, which were first
prepared by Hofmann in 1897 [10] and extensively studied by
Iwamoto and others, show 2D structures with variety of small mol-
ecules intercalated between the layers [11,12]. Based on this struc-
ture, metal(II) tetracyanonickelate complexes have been developed
2
2
2
⇑
Corresponding author. Tel.: +90 222 2393750; fax: +90 222 2393578.
E-mail address: gkurkcuo@ogu.edu.tr (G.S. Kürkçüo g˘ lu).
were purchased from commercial sources and used without further
purification. The carbon, hydrogen and nitrogen content were
0
022-2860/$ - see front matter Ó 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.molstruc.2011.02.046

4
0
G.S. Kürkçüo g˘ lu et al. / Journal of Molecular Structure 994 (2011) 39–43
analysed with a LECO CHNS-932 analyzer. The FT-IR spectrum was
with stirring for 12 h at 60 °C. The reaction mixture was cooled
to room temperature. The colorless crystals formed were filtered
and washed with 10 mL of water and acetone and dried in air.
The product obtained was left overnight in the open air. The yellow
color plates like crystals formed on the top of solution were fil-
tered. The C, H, N analysis for the sample was carried out and
the results were found to fit well with the proposed formulae.
ꢁ1
recorded in the range 4000–400 cm on a Perkin–Elmer 100 FT-IR
spectrometer, using the KBr pellet technique. The Raman spectrum
ꢁ1
was recorded in the range of 4000–250 cm on a Bruker Senterra
Dispersive Raman instrument using laser excitation of 785 nm. Per-
kin–Elmer Diamond TG/DTA thermal analyzer was used to record
simultaneous TG, DTG and DTA curves in the static air atmosphere
ꢁ1
at a heating rate of 10 K min in the temperature range 30–700 °C
The result is as follows (% found, % calculated): Cd(C
C(34.54/34.87), N(20.14/20.33), H(3.43/3.41).
4 7 2 4
H N) Ni(CN) :
using platinum crucibles.
2
2
.2. Synthesis
2.3. X-ray crystallography
4
.2.1. Cd[Ni(CN) ]
A mixture of a solution of NiCl
20 mL) and a solution of KCN (1.30 g, 20 mmol) in water (20 mL)
was added dropwise with stirring at 50 °C to a solution of CdCl
0.92 g, 5 mmol) in water (20 mL). The mixture was refluxed with
stirring for 2 h at 50 °C in a temperature-controlled bath and then
the solution was cooled to room temperature.
2
ꢀ6H
2
O (1.18 g, 5 mmol) in water
Diffraction experiments were carried out at 296 K on a Stoe
(
IPDS diffractometer. The structures were solved by direct methods
and refined using the programs SHELXS97 and SHELXL97 [18]. All
non-hydrogen atoms were refined anisotropically by full-matrix
least-squares methods [18]. The hydrogen atoms were placed in
geometrically idealized positions and refined as riding atoms. The
following procedures were implemented in our analysis: data col-
lection: X-Area, cell refinement: X-Area, data reduction: X-RED
[19]; program(s) used for molecular graphics were as follows: OR-
TEP-3 for Windows [20]; software used to prepare material for
publication: WinGX [21].
2
(
2
.2.2. [Cd(pyr)
A solution of 3-pyrroline (0.346 g, 5 mmol) in ethanol (10 mL)
was added dropwise upon stirring to a solution of Cd[Ni(CN)
1.371 g, 5 mmol) in water (30 mL). The solutions were refluxed
2 4 n
Ni(l-CN) ]
4
]
(
Fig. 1. The FT-IR (a) and Raman (b) spectra of 1.

G.S. Kürkçüo g˘ lu et al. / Journal of Molecular Structure 994 (2011) 39–43
41
Table 2
3
. Results and discussion
The vibrational wavenumbers (cmꢁ1) of the [Ni(CN)
]
2ꢁ
unit in 1.
4
3.1. Vibrational spectra
Assignmentb
Na
2
[Ni(CN)
4
] [24]
Cd–Ni–Pya [25]
1
A
1g
,
,
m
(CN)
(2149) vs
(2141) vs
2132 vs
2087 sh
543 w
(2172) vs
(2160) s
2154 s
2111 w
543 w
–
(2164) vs
–
2146 vs
2109 vw
545 w
–
The FT-IR and Raman spectra of 1 are given in Fig. 1a and b,
B
1g
m
(CN)
E
u
,
m
(CN)
respectively. Up to now, there has been no extensive vibrational
study of pyr, although the microwave and infrared spectra on pyr
and its N-deuterated species have been reported [22]. Therefore
the spectral features due to the pyr in 1 were evaluated through
the measured infrared frequencies of the free molecule. Addition-
ally, normal mode frequencies and assignments of pyr (in gas
phase) have been calculated at the B3LYP/6-311G(d, p) level by
using the package Gaussian 03 [23]. The tentative assignments
and the wavenumbers of the vibrational bands of the 3-pyrroline
observed in the FT-IR and Raman spectra of 1 are presented in
Table 1, together with the wavenumbers for the calculated data
of the pyr. In the FT-IR and Raman spectra of 1, the absorption band
1
3
m( CN)
E
u
,
m
,
(NiC)
p
A
2u
(NiCN)
448 w
Eu, d(NiCN)
421 s
425 s
423 vs
The bands observed in the Raman spectra are given in parentheses.
a
Cd–Ni–Py: [Cd(py)
2
Ni(CN)
Abbreviations used: s, strong; m, medium; w, weak; sh, shoulder; v, very. The
symbols and refer to valence, in-plane and out-of-plane vibrations,
4
].
b
m
,
d
p
respectively.
Table 3
ꢁ1
at 3291 cm is assigned to the NH stretching frequency which is
lower than the corresponding value for the pyr molecule
Crystal data and structure refinement parameters for complex 1.
1
ꢁ
1
(
3440 cm ) and characteristic of bonded Cd–NH group. This
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
a (Å)
12 6
C H14CdN Ni
413.40
293 (2)
0.71073 MoK
Orthorhombic
downward frequency shift can be explained as being due to weak-
ening of the N–H bonds for electron draining from the N atom on
account of its coordination to the Cd atom. A metal-dependent
frequency shift is also observed for the NH wagging mode; e.g.,
a
ꢁ1
Pmna
the band at about 878 cm can be assigned to the NH bending
vibration derived from the similar degenerate mode in 1. The NH
wagging mode shifts to higher frequency in complex form
7.824 (2)
6.922 (1)
14.407 (2)
780.2 (2)
b (Å)
c (Å)
ꢁ1
3
(
892 cm ). These shifts can be explained as the coupling of the
V (Å )
Z
internal mode of the pyr with MꢁN vibrations.
1
Absorption coefficient (mm )
2.57
1.760
2.83–27.50
2907
In the spectra of 1 the dominant feature is represented by
3
Dcalc (Mg m )
strong and sharp well identifiable bands due to the
ing vibrations. The (C„N) vibrations are the most important
absorption bands for the complexes since the (C„N) vibrational
m(CN) stretch-
Theta range for data collection (ꢀ )
Measured reflections
Independent reflections
Absorption correction
m
m
947
Integration Stoe X-RED
peaks in the FT-IR and Raman spectra are used to elucidate the
Stoe and Cie [19]
bridging formation in the polymeric complexes [2]. The vibrational
Full-matrix least-squares on F2
Refinement method
Final R indices [I > 2
Final R indices (all data)
2
ꢁ
wavenumbers of the [Ni(CN)
4
]
group for 1 are given in Table 2. In
r
(I)]
Rint = 0.047
2ꢁ
order to assign the bands attributable to the [Ni(CN)
4
]
ion in the
R1 = 0.034
2
wR = 0.089
Goodness-of-fit on F2
1.16
0.56
Table 1
0
D
D
q
q
max (e ÅA ꢁ3)
min (e ÅA ꢁ3)
The vibrational wavenumbers (cmꢁ1) and assignments of pyr in 1.
0
ꢁ0.65
Assignment [22]
pyr
1
Calculated
Experimental
FT-IR
Raman
m
m
m
m
m
m
(NH)
(CH)
(CH)
(CH)
(CH)
(C@C)
3447
3098
3075
2931
2879
1616
1461
1454
1407
1320
1306
1273
1198
1154
1081
1065
1021
981
3440 m
–
3291 w
3289 m
3049 w
2959 m
2931 m
2878 s
1604 w
1475 w
–
1414 w
–
–
1292 w
–
–
1100 w
–
–
971 w
962 w
–
890 vw
780 vw
–
3049 vw
2957 vw
2931 vw
2878 vw
1633 w
1478 wv
1462 w
1413 w
1331 w
–
spectra, we refer to the work of McCullough et al. who presented
vibrational data for the salt Na [Ni(CN) ] in the solid state [24]
] [25] for comparison. The assigned wavenum-
3070 m
2947 m
2836 s
1615 m
1473 m
1456 vw
1412 m
1327 m
1311 vw
1283 vw
1180 m
1153 vw
1084 s
1064 vw
1031 s
965 m
2
4
and [Cd(py)
2
Ni(CN)
4
2
ꢁ
bers of the [Ni(CN)
those for isolated [Ni(CN)
is observed at 2146 cm in the FT-IR spectrum of 1 whereas the
4
]
units of 1 appear to be much higher than
d(CH
d(CH
d(CH
d(CH
d(CH)
d(CH
d(CH
2
2
2
2
)
)
)
)
2ꢁ
4
]
ion. The CN stretching mode, m(CN),
ꢁ
1
2ꢁ
IR active
m
(CN) mode (E
u
) of free [Ni(CN)
4
]
group is observed at
ꢁ
1
2132 cm in the FT-IR spectrum of solid Na
2
[Ni(CN)
4
]. The up-
)
)
–
ꢁ1
ꢁ
2ꢁ
2
ward shift of 14 cm on going from CN to NiðCNÞ was explained
4
2
1191 w
1166 w
1079 m
1056 m
1028 vw
968 s
956 m
918 w
892 s
as the mechanical coupling of the Ni–C(CN) stretching mode with
m
(CN)
d(CH)
(CAC)
the
m(CN) [25]. Such frequency shifts have been observed for the
m
other cyano-bridged complexes [2,13–17,26,27] and are attributed
2
ꢁ
d(CH
d(CH
d(CH
2
2
2
)
)
)
to the mechanical coupling of the internal modes of [Ni(CN)
4
]
with the M–NC vibrations. It follows that the N-termini of the
931
921
878
779
736
692
652
928 w
906 s
2
ꢁ
[
Ni(CN)
4
]
group are bound to a Cd atom in the complex
c(CH)
d(NH)
866 vw
789 vw
725 vw
663 vs
662 vs
investigated.
c
c
c
s
ring
790 vw
734 m
674 s
ring(CH)
(NH)
(CH)
675 w
650 vw
3.2. Crystal structure
649 w
⁄
Abbreviations used:
m
, stretching; d, deformation; w, wagging; t, twisting; r,
The molecular structure of 1 with the atom labelling is shown in
Fig. 2. Experimental data are listed in Table 3. The selected bond
rocking; s, strong; m, medium; w, weak; sh, shoulder; v, very.

4
2
G.S. Kürkçüo g˘ lu et al. / Journal of Molecular Structure 994 (2011) 39–43
Table 4
Selected geometric parameters (Å, °) for complex 1.
Bond Bond angles
distances
C5–Ni1
ii
1.869 (3) C5 –Ni1–
91.6 (2) N1–Cd1–
98.0 (1)
83.3 (1)
159.7 (2)
93.6 (1)
86.4 (1)
vi
C5
N2
N1–Cd1
N2–Cd1
2.300 (5) C5iii–Ni1–
88.4 (2) N1–Cd1–
v
C5
N2
v
2.374 (3) N1–Cd1–
82.0 (1) N1 –Cd1–
N2
N1
i
N1–Cd1–
96.8 (1) N2 –Cd1–
N2i
N2
N2 –Cd1–
v
N2
Symmetry codes: (i) ꢁx + 1, y, z; (ii) ꢁx, y, z; (iii) x, ꢁy + 2, ꢁz + 1; (iv) ꢁx, ꢁy + 2,
ꢁ
z + 1; (v) x, ꢁy + 1, ꢁz + 1; (vi) ꢁx + 1, ꢁy + 1, ꢁz + 1.
i
ii
networks. The intralayer Cdꢀ ꢀ ꢀCd (i: ꢁ1 + x, y, z) and Cdꢀ ꢀ ꢀCd (ii:
ꢁ
1 + x, 1 + y, z) distances are 7.824 and 10.446 Å, whereas the
iii
shortest interlayer Cdꢀ ꢀ ꢀCd (iii: 1/2 ꢁ x, 1 ꢁ y, ꢁ1/2 + z) distance
is 8.197 Å. The Cd1–N2 = C5 bond angle (153.75°) is found to be
slightly bent.
Fig. 2. Molecular structure of 1 with atom-labelling scheme [symmetry codes: (i)
ꢁ
1 + x, y, z; (ii) ꢁ1 + x, 1 + y, z; (iii) x, 1 ꢁ y, 1 ꢁ z; (iv) 1 ꢁ x, y, z; (v) 1 ꢁ x, 1 ꢁ y,
1
ꢁ z; (vi) x, 2 ꢁ y, 1 ꢁ z].
The most interesting structural features of complex is the pres-
ence of obvious C–HꢀꢀꢀM interaction between the Ni(II) center and
H3 atom of pyr ligand. The crystal packing of complex is stabilized
through interlayer weak C–HꢀꢀꢀNi hydrogen bonding interaction,
resulting in a 3D framework (Fig. 3). The NiꢀꢀꢀH distance of
2.760 Å, NiꢀꢀꢀC distance of 3.505 Å and C–HꢀꢀꢀNi angle of 137.79°
are similar to those values for reported Ni(II) complexes [28–30].
This interactions should be well described as being of a weak inter-
molecular C–HꢀꢀꢀNi hydrogen bonding. To the best of our knowl-
edge, this manner has not been reported so far although there
are many complexes of tetracyanonickelate(II) [13–17]. This inter-
layer interaction gives three-dimensional framework.
lengths and angles are given in Table 4. Single X-ray crystal analy-
sis reveals that the complex 1 crystallizes in the orthorhombic
space group Pmna, which is a two-dimensional coordination poly-
mer. Each nickel(II) ion is coordinated by four cyano ligands, form-
ing a square planar geometry. The Ni1–C5 bond distance of 1.869
(
3) Å is also similar to those found in reported tetracyanonicke-
late(II) complexes [13–18]. In 1, the Cd(II) ion is also coordinated
by four bridging cyanide ligands and two trans pyr ligands, forming
distorted octahedral geometry (Fig. 2). The structure consists of
corrugated and cyano-bridged heteropolynuclear two-dimensional
Fig. 3. Unit cell structure in 1.

G.S. Kürkçüo g˘ lu et al. / Journal of Molecular Structure 994 (2011) 39–43
43
3.3. Thermal analysis
References
[
[
[
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has similar structure with linkage between the square planar
_
[
[
[
[
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Ni(CN)
4
]
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This work was supported by the Research Fund of Eski sß ehir
Osmangazi University. Project No. 201019024. Raman spectra were
recorded at Anadolu University, Department of Physics. The
authors thank Prof. Dr. Mustafa Sß enyel for support during the Ra-
man spectra.
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