Syntheses, spectral, thermal and structural characterization of 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline and its novel nickel(II) complex

Article abstract of DOI:10.1002/zaac.200600343

The 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline (HL) and its Ni^II complex have been prepared and characterized by spectral method (FT-IR, NMR (¹³C and ¹H), UV-vis.), elemental analysis, magnetic susceptibility and thermal analysis (TG, DTA) techniques. The crystal structures of HL and Ni^II complex were also determined by the single crystal X-ray diffraction. The HL and Ni^II complex crystallizes in the monoclinic and triclinic, space groups P2₁/c and P1, respectively. The complex was occurred by the elimination of 1 mole of 2-aminobenzylamine from the 2 moles of the HL after the ring opening reaction by the Ni^II attack. Crystallographic study reveal that Ni ^II atom has a square planer geometry being coordinated by four nitrogen atoms of HL. Two thermal processes of the HL and Ni^II complex can occur in TG and DTA curves.

Full text of DOI:10.1002/zaac.200600343

DOI: 10.1002/zaac.200600343
Syntheses, Spectral, Thermal and Structural Characterization of 2-Phenyl-2-(1-
hydroxyiminoethyl)-1,2,3,4-tetrahydroquinazoline and Its Novel Nickel(II) Complex
a
b
c
d,
e
˙
Alper Tolga Colak , Murat Tas , Gazi Irez , Okan Zafer Yesilel * and Orhan Büyükgüngör
¸
¸
¸
a Kütahya / Turkey, Dumlupinar University, Faculty of Arts and Sciences, Department of Chemistry
b Giresun / Turkey, Giresun University, Faculty of Arts and Sciences, Department of Chemistry
c Bursa / Turkey, Uludag˘ University, Faculty of Arts and Sciences, Department of Chemistry
d Eskis¸ehir / Turkey, Eskis¸ehir Osmangazi University, Faculty of Arts and Sciences, Department of Chemistry
e Samsun / Turkey, Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics
Received November 3rd, 2006, revised November 30th, 2006.
Abstract. The 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydro-
quinazoline (HL) and its NiII complex have been prepared and
characterized by spectral method (FT-IR, NMR (13C and 1H), UV-
vis.), elemental analysis, magnetic susceptibility and thermal analy-
sis (TG, DTA) techniques. The crystal structures of HL and NiII
complex were also determined by the single crystal X-ray diffrac-
tion. The HL and NiII complex crystallizes in the monoclinic and
the 2 moles of the HL after the ring opening reaction by the NiII
attack. Crystallographic study reveal that NiII atom has a square
planer geometry being coordinated by four nitrogen atoms of HL.
Two thermal processes of the HL and NiII complex can occur in
TG and DTA curves.
¯
triclinic, space groups P21/c and P1, respectively. The complex was
Keywords: 1,2,3,4-Tetrahydroquinazoline; Quinazoline; Dioxime;
occurred by the elimination of 1 mole of 2-aminobenzylamine from
Imine-oxime
1 Introduction
benzene or xylene with azeotropic water removal, in re-
fluxing ethanol/acetic acid mixtures and by reaction in
alkali media or by the condensation of 2-aminobenzyl-
amine with aromatic aldehydes in ionic liquids followed by
extraction into diethyl ether [13Ϫ15]. The 1,2,3,4-tetra-
hydroquinazolines may also be prepared by the simple
method of slurring the reagents together in water at
ambient temperature in a similar manner in the synthesis
of aromatic Schiff bases by the Tanaka’s method [13Ϫ16].
In this work, a 2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-
tetrahydroquinazoline and its NiII complex were synthe-
sized and characterized by spectral (FT-IR, NMR (13C and
1H), UV-vis.) and thermal method. Structures determi-
nations were performed by the X-ray single crystal analyses.
2-phenyl-2-(1-hydroxyiminoethyl)-1,2,3,4-tetrahydro-
quinazoline as a ligand which contains an oxime parts
was synthesized from 2-aminobenzylamine and 1-phenyl-
1,2-propanedione-2-oxime (Scheme 1) . Oximes as ligands
have played a significant role in the development of tran-
sition metal chemistry. This development has been docu-
mented in a number of review articles and we refer the read-
ers to some of these excellent treatises [1Ϫ8]. An early treat-
ise by Chakravorty [1] is a comprehensive review on the
structural chemistry of simple oximes, vic-dioximes, quin-
onemonoximes, and carbonyl-, imine-, pyridine-, azo-,
hydroxy- and amidoximes. Oxime derivatives are very im-
portant compounds because of their biological activity,
such as insecticidal, miticidal, nematocidal activities, anti-
dote activities for organophosphor poison. Some oxime
complexes have anti cancerogenic activities [9Ϫ11]. 1,2,3,4-
Tetrahydroquinazolines which are heterocyclic compounds,
are of interest as dihydrofolate reductase inhibitors, anti-
tubercular and antibacterial agents [13]. 1,2,3,4-Tetrahydro-
quinazolines can be prepared by the condensation of 1,3-
diamines and substituted aldehydes or ketones in refluxing
2 Results and Discussion
2.1 Characterization of HL
The NMR measurements were made in DMSO-d6 and
TMS was used as internal standard. The proton spectrum
was measured from freshly synthesized compound. The
spectrum was repeated in one day period during one week,
but no change showing the tautomeric forms, was detected.
Chemical shift assignments were based, in addition to form
normal proton and carbon measurements, on DEPT experi-
1
`
* Dr. Okan Zafer Yes¸ılel
ments. In the H NMR spectrum of the ligand, a singlet
Eskis¸ehir Osmangazi University,
Faculty of Arts and Sciences,
Department of Chemistry
Eskis¸ehir / TURKEY
peak for the OH proton of oxime group is observed at
8.57 ppm. The NϪH proton adjacent to the CH2 groups in
the heterocyclic ring resonates at 2.19 ppm and the other
one resonate at 4.94 ppm. The CH2 group of the hetero-
EϪmail: yesilel@ogu.edu.tr
504
 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2007, 633, 504Ϫ508

A Nickel(II) Complex
cyclic ring of the ligand resonates at 3.82 ppm. The CH3
protons adjacent to the oxime group resonate at 1.81 ppm.
The aromatic CϪH protons resonate at 6.62Ϫ7.56 ppm.
In the IR spectra of the ligand, bands at 3386, 3320,
3305, 3040Ϫ3005, 2900Ϫ2840, 1632, 1350Ϫ1315, and
960 cmϪ1 belong to N1ϪH, N3ϪH, OϪH, CϪHarom.
,
CϪHaliph., CϭN, ϪCϪNϪ and NϪO vibrations, respec-
tively. The NMR and IR spectrum of HL is synthesized
which contains the oxime part, was in good agreement of
with the known oximes [17Ϫ20] and 1,2,3,4-tetra-
hydroquinazolines [14, 15] and suitable for the synthesized
1,2,3,4-tetrahydroquinazoline ligand.
The crystallographic data of the compound are summar-
ized in Table 1 and selected bond lengths and angles and
hydrogen bond geometries are listed in Table 2. The molec-
ular structure and inter molecular hydrogen bonds of HL
are shown in Figure 1 and 2, respectively.
The intermolecular hydrogen bonds found at x, y, zϪ1
for N1ϪH1···O20 and C9ϪH9···O20 and at 1Ϫx, Ϫy, 1Ϫz
for the O20ϪH20···N19 and O20ϪH20···N1. The intermo-
lecular hydrogen bonds are at x, y, zϪ1, bonded molecules
to each other to form molecular sheets through the axis.
The intermolecular hydrogen bonds at 1Ϫx, Ϫy, 1Ϫz, are
found between the molecular sheets that were formed by the
N1ϪH1···O20 and C9ϪH9···O20 intermolecular hydrogen
bonds. So, the hydrogen bonds formed the two dimensional
polymeric structure of the synthesized HL in solid state.
Fig. 2 The intermolecular interactions of the HL ligand with
unit cell.
tion, by the template effect of the NiII, the ligand HL was
treated with the different equivalent amount of NiII. But,
it was found that at each time, the products were red and
diamagnetic and had the same IR and UV-Vis. spectra,
indicated that was a complex of only one tautomer of HL.
In the IR spectrum of the complex, there are no peaks for
NϪH and OϪH belongs to the ligand since complex form
upon deprotonation of NϪH and OϪH hydrogen atoms.
The CϭN vibration of the ligand shifted to 1610 cmϪ1 indi-
cated that the both oxime and imine nitrogen atoms bonded
to the Ni2ϩ ion. The NϪO vibration of the ligand shifted
to higher frequency for the nickel(II) complex indicating
that the oxime oxygen non-coordinated to the nickel atom.
These results may be suitable with complex of the diimine
tautomer of the synthesized ligand. But, as unexpected, the
complex has a band at 1380 cmϪ1 for the ϪCϪNϪ vi-
bration indicating that the nitrogen atom bonded to the
nickel atom. These results indicating that the ligand in the
complex is non of the known tautomer of the 1,2,3,4-tetra-
hydroquinazolines and the IR results do not give any ad-
dition knowledge to estimate structure of the complex.
The X-ray single crystal structural studies showed the li-
gand in the complex has whole different structure from the
known tautomer of the 1,2,3,4-tetrahydroquinazolines. The
X-ray single crystal structure analysis of the complex
showed may be formed by the elimination 1 mole of
2.2 Characterization of the NiII complex
To prepare the complexes of the tautomeric forms of the
ligand HL that was only one form in both solid and solu-
2-aminobenzylamine from
2
moles of 1,2,3,4-tetra-
hydroquinazoline and the ethanol which is presence of the
reaction media as solvent, acted as reactant (Scheme 2).
The crystallographic data of the complex were summarized
in Table 1 and selected bond lengths, angles and hydrogen
bond geometries are given Table 3. Tough the ligand
in the complex is like the diimine tautomers of 1,2,3,4-tetra-
hydroquinazolines [13Ϫ15], it had completely different
bond properties. Fist of all, the ligand in the complex has
an ethoxy part bonded to carbon atom of the ketone in the
Fig. 1 ORTEPϪIII diagram with 30 % probability ellipsoids of HL
Z. Anorg. Allg. Chem. 2007, 504Ϫ508
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505

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A. T. C¸ olak, M. Tas¸, G. Irez, O. Z. Yes¸ilel, O. Büyükgüngör
benzylamine type tautomer parts of the diimine tautomer
act as hydrogen bond donors via their H14 and H15 atoms
to O20Ј and N19 atoms, respectively. In addition to this
intra and inter actions, weak CϪH···π inter action was
found between the H14 atom of the C14 carbon and centre
of gravity (Cg) of the C5ϪC10 ring (phenyl ring of
2-aminobenzylamine) at 1Ϫx, 1Ϫy, 1Ϫz. The hydrogen
bonds and CϪH···π inter action of the complex were shown
in Figure 4.
[13, 15]. In this part, N1ϪC2 and N1ϪC10 bond lengths
˚
are 1.475(4) and 1.371(4) A, respectively, indicate these
bonds are single as unlike diimine tautomers of 1,2,3,4-
tetrahydroquinazolines. In addition to the difference, the
double bond which was between the N atom and the carbon
atom of the ketone in the aniline type tautomer parts of the
diimine tautomers of 1,2,3,4-tetrahydroquinazolines
[13Ϫ15], was found between carbon and N atoms of the
benzylamine part of the ligand in the complex. The C2ϪN1
and N3ϪC4 and N3ϪC2Ј bond lengths indicated the
double bond is in N3ϪC4, are 1.475(4) and 1.298(4) and
2.3 Thermal Analyses
The HL ligand exhibits three decomposition stages. The li-
gand melts at 106.3 °C and then in the temperature range
of 115Ϫ342 °C, HL ligand involves the consecutive de-
compositions by giving exothermic effects (DTA ϭ 158 and
224 °C). The third stage is related to the burning of the
remain organic residue, in the temperature range of
343Ϫ557 °C (DTA ϭ 521 °C).
˚
1.477(4) A, respectively. Like glyoximes, in the complex the
OϪH···O hydrogen bond bridge occurres to stabilize the
square-planar geometry in around of NiII atom (Fig. 3)
[18Ϫ21]. Also, at 2Ϫx, 1Ϫy, 1Ϫz to bond complex mol-
ecules to each other, the C14 and C15 atoms of the complex
Fig. 3 An ORTEPϪIII drawing of complex with displacement ellipsoids shown at the 30 % probability.
Fig. 4 The intra- and intermolecular interactions of the Nickel(II) complex with unit cell.
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 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Z. Anorg. Allg. Chem. 2007, 504Ϫ508

A Nickel(II) Complex
II
Table 1 Crystallographic data of the HL and NiII complex
Table 3 Structural parameters /A, ° for Ni complex
˚
NiII Complex
Bond lengths /A
Bond angles /°
˚
HL
Formula
C16H17N3O
267.33
monoclinic
P21/c
10.745(5)
20.324(5)
6.687(5)
90
107.545(5)
90
1392.4(13)
4
C27H28N4O3Ni
515.24
N1ϪC2
N1ϪC10
N3ϪC4
N3ϪC2Ј
C4ϪH4
C17ϪN19
C17ЈϪN19Ј
C2ϪO1
N19ϪO20
N19ЈϪO20Ј
NiϪN1
NiϪN3
NiϪN19
NiϪN19Ј
1.475(4)
1.371(4)
1.298(4)
1.477(4)
0.930(4)
1.272(4)
1.281(4)
1.431(4)
1.357(3)
1.359(3)
1.858(3)
1.834(2)
1.859(3)
1.881(3)
N1ϪC10ϪC5
C10ϪC5ϪC4
C5ϪC4ϪN3
C4ϪN3ϪNi
N1ϪC2ϪC17
N3ϪC2ЈϪC17Ј
C17ϪN19ϪNi
C17ЈϪN19ЈϪNi 119.4(2)
N3ϪNiϪN1
N1ϪNiϪN19
N3ϪNiϪN19Ј
N19ϪNiϪN19Ј
N1ϪNiϪN19Ј
N3ϪNiϪN19Ј
120.4(3)
123.7(3)
126.1(3)
126.0(2)
107.2(2)
107.0(3)
117.9(2)
Formula Weight
Crystal System
Space group
triclinic
¯
P1
˚
a /A
10.502(2)
11.050(3)
11.603(2)
79.25(2)
72.81(1)
80.58(2)
1255.3(5)
2
˚
b /A
˚
c /A
α /°
β /°
γ /°
95.9(1)
84.9(1)
83.0(1)
96.2(1)
178.8(1)
178.0(1)
3
˚
V (A )
Z
Densitiy ρcalc /(g/cm3)
µ(MoϪKα) /mmϪ1
F(000)
1.275
0.082
568
1.363
0.808
540
˚
Crystal Size /mm
0.10ϫ0.49ϫ0.58 0.18ϫ0.34ϫ0.41
HydrogenϪbonding /A
DϪH···A
˚
Data Collection
D···A /A
Temperature /K
Radiation /A
293
˚
MoϪKα 0.71073
O20ϪH20···O20Ј
C14ϪH14···O20Ј i
C15ϪH15···N19i
C14ЈϪH14Ј···Cgii
2.412(4)
3.464(7)
3.732(6)
3.774(6)
Theta range /°
Indis range
2.0 < θ < 27.0
hϭ Ϫ13 Ǟ 13,
kϭ Ϫ25 Ǟ 25,
lϭ Ϫ8 Ǟ 7
2.4 < θ < 26.0
h ϭ Ϫ12 Ǟ 12,
k ϭ Ϫ13 Ǟ 13,
l ϭ Ϫ14 Ǟ 14
Tot., Uniq. Data, Rint
Observed data [I > 2σ(I)]
14993, 3052, 0.077 18099, 4933, 0.080
i: 2Ϫx, 1Ϫy, 1Ϫz, ii: 1Ϫx, 1Ϫy, 1Ϫz.
2016
3810
Refinement
Nref, Npar
complex, leading finally to give NiO. The final decompo-
sition products was identified by IR spectroscopy. The over-
all weight loss agrees well with the proposed structure.
3052, 195
4933, 322
0.0493, 0.1199
R1, wR2 w ϭ 1/[σ2(Fo2)ϩ(0.0814P)2] 0.0481, 0.1405
where P ϭ (Fo2ϩ2Fc2)/3
Goodness of fit
1.01
1.05
3 Experimental Section
˚
Table 2 Structural parameters /A, ° for HL
3.1 Materials and measurements
˚
Bond lengths /A
Bond angles /°
C10ϪN1ϪC2
N1ϪC2ϪN3
C2ϪN3ϪC4
N3ϪC4ϪC5
N1ϪC2ϪC11
N3ϪC2ϪC11
C11ϪC2ϪC17
C2ϪC17ϪN19
All chemicals used were analytical reagent. Elemental analyses for
C, H, and N were carried out at the TÜBITAK Marmara Research
˙
N1ϪC2
N1ϪC10
N3ϪC4
1.468(2)
1.383(2)
1.461(3)
1.465(2)
0.78(2)
121.3(2)
111.6(1)
111.2(1)
113.3(2)
108.0(1)
112.0(1)
107.7(1)
117.5(1)
Centre. Magnetic susceptibility measurements at room tempera-
tures were performed using a Sherwood Scientific MK1 model
Gouy magnetic balance. UV-vis. spectrum was obtained in the
methanol solutions (10Ϫ3 mol/L) of the complex with a Unicam
UV2 spectrometer in the range of 900Ϫ190 nm. The 1HϪNMR
and 13C-NMR spectra were recorded on a Varian Mercury Plus
400 MHz FTϪNMR spectrometer, utilizing deuterated dimethyl-
sulphoxide as a solvent and TMS was used as an internal standard.
FTϪIR spectra were recorded in the 4000Ϫ400 cmϪ1 region with
a Mattson 1000 FTϪIR spectrometer using KBr pellets. Thermal
analysis curves (TG and DTA) were recorded simultaneously in a
static air atmosphere with a Shimadzu DTA 50 thermal analyzer.
The heating rate was 10 °C minϪ1. The crystal data were collected
using ωϪ2θ scan techniques on Stoe IPDSϪ2 diffractometer with
N3ϪC2
N1ϪH1
N3ϪH3
C2ϪC17
C17ϪN19
N19ϪO20
O20ϪH20
0.93(2)
1.538(2)
1.268(2)
1.417(2)
0.96(3)
C17ϪN19ϪO20 112.2(1)
N19ϪO20ϪH20 102(2)
˚
HydrogenϪbonding /A
DϪH···A
˚
D···A /A
N1ϪH1···O20i
C9ϪH9···O20i
O20ϪH20···N19ii
O20ϪH20···N1ii
3.314(3)
3.510(3)
2.822(2)
3.630(2)
˚
a graphite-filtered MoϪKͰ radiation (λ ϭ 0.71073 A). Software
program(s) used, for data collection and cell refinement: XϪAREA
[22]; for data reduction: XϪRED32 [22]; to solve structure:
SHELXS86 [23]; to refinement structure: SHELXL97 [24]; for
molecular graphics: ORTEPIII [25]; to prepare material for publi-
cation: WinGX [26].
i: x, y, zϪ1, ii: 1Ϫx, Ϫy, 1Ϫz
The NiII complex has a high thermal stability. The first
decomposition stage begins at 230 °C. In the temperature
range of 231Ϫ245 °C, the first stage of the complex is re-
lated to release of the ethanol group of HL ligand (found ϭ
9.64, calcd. ϭ 8.75), by giving exothermic contribution in
the DTA curve (DTA ϭ 241 °C). The following two exo-
thermic stages involve successive decomposition of HL. In
the last stage, remain organic part is abruptly burnt in the
3.2 Synthesis of HL
The compound can be alternatively named as 1-(2-phenyl-1,2,3,4-
tetrahydro quinazolin-2-yl)ethanone oxime. A solution of 2-amino-
benzylamine (10 mmol, 1.25 g) in EtOH (30 ml) was added drop
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507

˙
A. T. C¸ olak, M. Tas¸, G. Irez, O. Z. Yes¸ilel, O. Büyükgüngör
wise to a solution of 1-phenyl-1,2-propanedione-2-oxime (10 mmol,
1.64 g) in ethanol at Ϫ5 °C. After 1 hour, glacial acetic acid (1.5 ml)
was added drop wise to the mixture. The solutions were cooled to
Ϫ15 °C in a temperature-controlled bath and stirred for 4 h. The
solutions were kept 12 h and then the crystalline products were
collected by filtration, dried on air (Scheme 1). The precipitated
product was filtered, washed with water and then recrystallized
from ethanol. Yield 84 % (beige needless crystals); mp 106.3 °C;
Analytical data: C16H17N3O (267.33 gmolϪ1); C 71.85 (calc. 71.89);
H 6.41 (6.38); N 15.75 (15.72) %.
1H NMR (DMSO-d6) δ ϭ 1.81 (s, 3H, ϪCH3), 2.19 (s, 1H, ϪN3H), 3.82 (m,
2H, ϪCH2), 4.94 (s, 1H, ϪN1H), 8.57 (s, 1H, ϪOH), 6.62 (d, 1H, J ϭ 8 Hz,
H-9), 6.66 (t, 1H, J ϭ 7.3 Hz, H-7), 6.85 (d, 1H, J ϭ 7.3 Hz, H-6), 7.04 (t,
1H, J ϭ 7.3 Hz, H-8), 7.30 (d, 2H, J ϭ 10 Hz, H-12), 7.31 (t, 1H, J ϭ 7.3 Hz,
H-14), 7.56 (t, 2H, J ϭ 8 Hz, H-13). 13C NMR ([D6]DMSO) δ ϭ 10.38 (C-
18), 42.91 (C-4), 74.35 (C-2), 115.47 (C-9), 118.15 (C-7), 121.39 (C-5), 122.57
(C-14), 126.17 (C-8), 126.80 (C-12), 127.87 (C-16), 128.21 (C-13), 128.55 (C-
15), 128.89 (C-6), 141.96 (C-11), 142.03 (C-10), 158.78 (C-17); IR (KBr):
ν(N1-H) 3386 s, ν(N3-H) 3320 s, ν(OH) 3305 s, ν( CϪHarom.) 3040Ϫ3005 w,
3.4 Supplementary Data
Crystallographic data (excluding structure factors) have been
deposited with the Cambridge Crystallographic Data Centre as the
supplementary publication No. CCDC 616665, 616666. Copies
of the data can be obtained, free of charge, on application to
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: ϩ44-1223-
336033 or e-mail: deposit@ccdc.cam.ac.uk).
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) 2900Ϫ2840 w, ν(CϭN) 1632 s, ν(CϪNϪ) 1350Ϫ1315 m,
ν(NϪO) 960 m cmϪ1
.
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Scheme 1 Synthesis of HL
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3.3 Synthesis of the NiII complex
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A solution of HL (10 mmol, 2.67 g,) in ethanole (20 ml) was added
drop wise with stirring at 60 °C to a solution of NiCl2·6H2O
(5 mmol, 1.188 g) in ethanol (20 mL). The mixture was stirred for
4 h at 60 °C and then slowly cooled to room temperature (Scheme
2). The crystals formed were filtered and washed with 10 mL of
cold ethanol and dried on air. The complex named as 1-ethoxy-1-
{2- [(2-hydroxyimino-1-phenyl-propylimino)methyl-phenylamino}-
1-phenyl-propan-2-oneoximatonickel(II). Yield 71 % (red crystals);
d.p. 231 °C; Analytical data: C27H28N4O3Ni (515.24 gmolϪ1); C
62.91 (calc. 62.94); H 5.53 (5.48); N 10.91 (10.87) %.
´ ´
[14] A. Göblöys, L. Lazar, F. Fülöp, Tetrahedron 2002, 58, 1011.
[15] J. Sinkkonen, K. N. Zelenin, A. K. A. Potapov, I. V. Lagoda,
V. V. Alekseyev, K. Pihlaja, Tetrahedron 2003, 59, 1939.
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[17] M. Tas¸, H. Batı, J. Chem. Res. 2006, 87.
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Met. Org. Chem. 2003, 33, 625.
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¸
2001, 31, 541.
IR(KBr): ν(C-Harom.) 3100Ϫ3050 w, ν(C-Haliph.) 2877 w, ν(CϭN) 1610 s,
ν(C-N) 1380, ν(N-O) 1008 m, ν(Ni-N) 474 cmϪ1; UV/VIS: λmax (lg ε):
452 nm (1342); µeff: diamagnetic;
[20] H. Batı, M. Tas, M. Macit, Synth. React. Inorg. Met. Org.
¸
Chem. 1998, 28, 1371.
˘
[21] H. Batı, A. Zülfikaroglu, M. Tas¸, N. C¸ alıs¸kan, S. Soylu, O.
Andac, O. Büyükgüngör, Acta Crystallogr. 2004, E60, m1334.
[22] Stoe&Cie, X-Area (Version 1.18) and X-Red32 (Version 1.04).
Stoe&Cie, Darmstadt, Germany, 2002.
[23] G. M. Sheldrick, SHELXS86, University of Göttingen,
Germany, 1986.
[24] G. M. Sheldrick, SHELXL97, University of Göttingen,
Germany, 1997.
[25] L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
[26] L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
Scheme 2 Synthesis of the Nickel(II) complex
508
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