Synthesis, structure, and solution study of a mercury(II) complex with the ligand [1-(2-Methoxyphenyl)-3-(4-chlorophenyl)]triazene

Article abstract of DOI:10.1002/zaac.201100557

The title ligand, [1-(2-methoxyphenyl)-3-(4-chlorophenyl)]triazene, HL (1), was prepared. In a reaction with Hg(NO₃)₂ it forms the complex [Hg(C₂₆H₂₂Cl₂N₆O ₂)], [HgL₂] (2). Both compounds were characterized by means of X-ray crystallography, CHN analysis, FT-IR, ¹H NMR, and ¹³C NMR spectroscopy. In the structure of compound 1, two independent fragments are present in the unit cell. They exhibit trans arrangement about the -N=N- double bond. The dihedral angles between two benzene rings in both fragments are 4.36 and 18.79 A, respectively. Non-classic C-H...N hydrogen bonding and C-H...π interactions form a layer structure along the crystallographic ab plane [110]. In compound 2, the Hg^II atom is hexacoordinated by two tridentate [1-(2-methoxyphenyl)-3-(4-chlorophenyl)] triazenide ligands through a N₂O₂ set. In addition, in the structure of 2, monomeric complexes are connected to each other by C-H...π stacking interactions, resulting in a 2D architecture. These C-H...π edge-to-face interactions are present with H...π distances of 3.156 and 3.027 A. The results of studies of the stoichiometry and formation of complex 2 in methanol solution were found to support its solid state stoichiometry. Copyright

Full text of DOI:10.1002/zaac.201100557

ARTICLE
DOI: 10.1002/zaac.201100557
Synthesis, Structure, and Solution Study of a Mercury(II) Complex with the
Ligand [1-(2-Methoxyphenyl)-3-(4-chlorophenyl)]triazene
Mohammad Kazem Rofouei,[a] Zahra Ghalami,[a] Jafar Attar Gharamaleki,*[a]
Vanik Ghoulipour,[a] Giuseppe Bruno,[b] and Hadi Amiri Rudbari[b]
Keywords: Mercury; Triazene; X-ray diffraction; Solution study; C–H···π interaction
Abstract. The title ligand, [1-(2-methoxyphenyl)-3-(4-chlorophen-
C–H···π interactions form a layer structure along the crystallographic
yl)]triazene, HL (1), was prepared. In a reaction with Hg(NO3)2 it ab plane [110]. In compound 2, the HgII atom is hexacoordinated by
forms the complex [Hg(C26H22Cl2N6O2)], [HgL2] (2). Both com-
two tridentate [1-(2-methoxyphenyl)-3-(4-chlorophenyl)]triazenide li-
pounds were characterized by means of X-ray crystallography, CHN
gands through a N2O2 set. In addition, in the structure of 2, monomeric
analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy. In the structure complexes are connected to each other by C–H···π stacking interac-
of compound 1, two independent fragments are present in the unit cell.
tions, resulting in a 2D architecture. These C–H···π edge-to-face inter-
They exhibit trans arrangement about the –N=N– double bond. The actions are present with H···π distances of 3.156 and 3.027 Å. The
dihedral angles between two benzene rings in both fragments are 4.36 results of studies of the stoichiometry and formation of complex 2 in
and 18.79 Å, respectively. Non-classic C–H···N hydrogen bonding and methanol solution were found to support its solid state stoichiometry.
tio,[18] nature of the ligands,[19] solvents,[20] and/or counter-
anions,[21] or even the reaction temperature and pH value.[22,23]
1 Introduction
Triazene compounds having
a
diazoamino group
We have previously reported the synthesis of 1,3-bis(2-
methoxyphenyl)]triazene,[24] [1,3-bis(2-ethoxyphenyl)]triaz-
ene,[25] and [1,3-bis(2-cyanophenyl)]triazene[26] molecules that
can act as ligands. Additionally, we have published the HgII
complexes with [1,3-bis(2-methoxyphenyl)]triazene by using
HgCl2,[27] HgBr2,[28] Hg(CH3COO)2, and Hg(SCN)2 salts as
starting materials.[29] Moreover, AgI and CdII complexes with
this ligand are known.[30,31] Just recently, a HgII complex with
[1,3-bis(2-ethoxyphenyl)]triazene as ligand has been reported,
in which HgCl2 has been used as starting salt.[32] From recent
structural studies, it was argued that counter-anions play an
important role in determining the solid state lattices of these
compounds. Moreover, we are performing the synthesis and
spectroscopic study of some new asymmetric ligands and their
complexes with transition metal ions in our laboratory. In con-
tinuation with our previous work, we herein report the synthe-
sis, characterization, and molecular structure of a new asym-
metric triazene [1-(2-methoxyphenyl)-3-(4-chlorophenyl)]tria-
zene, HL (1), and its HgII complex [Hg(C26H22Cl2N6O2)],
[HgL2], (2) in methanol as solvent.
(–N=NNH–) commonly adopt a trans configuration in the
ground state.[1] Transition-metal complexes containing 1,3-di-
aryltriazenide ligands have been extensively studied because
of the versatility of their coordination, which yield a variety
of coordination compounds with large structural diversity.[2,3]
Triazenes and anionic triazenide ligands show different types
of coordination in metal complexes like monodentately,
(N1,N3)-chelating towards one metal atom or (N1,N3)-bridg-
ing over two metal atoms,[4] showing a remarkable ability to
support the stereochemical requisites of a wide variety of metal
transition complexes.[5,6] In these compounds secondary bonds
or interactions such as hydrogen bonds and metal π-aryl inter-
actions can play important roles in the structural stability.[7–11]
In this regard, organic ligands play an important role in ad-
justing the architectures of the resulting metal complexes, so
proper selection of ligands is the key issue in the construction
of supramolecular networks.[12–14] However, the crystal engi-
neering with desired topologies and specific properties still re-
mains a difficult challenge since a variety of factors influence
the self-assembly processes such as coordination arrangement
and oxidation state of the metal ions,[15–17] metal-to-ligand ra-
2 Experimental Section
* Dr. J. Attar Gharamaleki
Fax: +98-2188820993
E-Mail: attar_jafar@yahoo.com
[a] Faculty of Chemistry
Tarbiat Moallem University
Tehran, Iran
2.1 Materials and Physical Techniques
All chemicals were of analytical grade and were used as commercially
obtained without further purification. IR spectra were recorded with a
Perkin-Elmer RXI spectrometer using KBr disks. Elemental analysis
was carried out with a Perkin-Elmer 2400(II) CHNS/O analyzer. Melt-
ing points were measured with a Barnstead Electrothermal 9200 appa-
[b] Dipartimento di Chimica Inorganica
Universita di Messina
Messina, Italy
798
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Mercury(II) Complex with [1-(2-Methoxyphenyl)-3-(4-chlorophenyl)]triazene
ratus. UV/Vis spectra were recorded with a Perkin-Elmer Lambda 25 methanol (20 mL) was added. After stirring for 30 min, a yellow pre-
spectrophotometer, using two matched 10 mm quartz cells. Crystallo-
graphic measurements were made at 296 K with a Bruker APEX II
cipitate was formed. It was filtered off, washed with methanol and
dried in vacuo. The solid was dissolved in DMF (20 mL). The orange-
CCD area detector diffractometer. The intensity data were collected colored crystals of the complex suitable for X-ray analysis was ob-
within the range 2.2–27.5 using graphite monochromated Mo-Kα radia-
tion (λ = 0.71073 Å). The structure has been solved by direct methods
and refined by full-matrix least-squares techniques on F2 using
SHELXTL.[33] The molecular structure plots were prepared using OR-
tained by slow evaporation of the solvent in a week. M.p. 216–218 °C.
Elemental analysis for C26H22HgCl2N6O4 (713.15): calcd. C 47.15; H
3.92; N 11.77; found: C 47.13; H 3.69; N 11.72%. FT-IR (KBr): ν˜ =
the N–H band is suppressed; 1020 [s, m (O–C)], 1287 cm–1 [s,
TEP[34] and mercury.[35] Refinement of F2 was made against all reflec- (NNN)], a mean value with respect to the N–N absorptions in the free
tions. The weighted R-factor wR and goodness of fit S are based on ligand (average bond order) cm–1. H NMR (300 MHz, [D6]DMSO):
1
F2, conventional R-factors R are based on F, with F set to zero for δ = 3.72 (3 H, CH3), 6.95–7.67 (16 H, aromatic) ppm.
negative F2. The threshold expression of F2 Ͼ 2σ(F2) is used only
Crystallographic data (excluding structure factors) for the structures in
this paper have been deposited with the Cambridge Crystallographic
Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies
for calculating R-factors(gt), etc. and is not relevant to the choice of
reflections for refinement. R factors based on F2 are statistically about
twice as large as those based on F, and R factors based on all data are
of the data can be obtained free of charge on quoting the depository
even larger.
numbers CCDC-812066 and CCDC-856173 (Fax: +44-1223-336-033;
E-Mail: deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk).
2.2 Synthesis of [1-(2-Methoxyphenyl)-3-(4-chlorophenyl)]triazene
(1)
3 Results and Discussion
The reaction pathway is shown in Scheme 1. p-Chloroaniline (6.36 g,
0.05 mol) and HCl (4.68 g, 0.13 mol, d = 1.18 g·ml–1) were put in a
1000 mL flask in an ice bath. To the obtained solution, a solution of
sodium nitrite (4.14 g in 25 mL H2O) was added dropwise. Afterwards,
3.1 Structure Descriptions
Crystal data and experimental conditions for compounds 1
and 2 are given in Table 1. Selected bond lengths and angles
a diluted solution of o-anizidine (6.15 g, 0.05 mol) in methanol are listed in Table 2. The molecular structure of compound 1
(10 mL) was added to the above mixture. The pH of the solution was
adjusted at about 7–8 by addition of a solution of sodium acetate
(14.76 g, 0.18 mol) in H2O (14.76 g). The solution was stirred for
about 1 h, yielding a brown precipitate. It was filtered off and dried in
vacuo. After dissolving in n-hexane and recrystallization, brown crys-
tals of the title ligand were obtained. M.p. 68 °C. Elemental analysis
for C13H12ClN3O: calcd. C 59.80, H 4.59, N 16.01%; found C 59.65,
is shown in Figure 1, thermal ellipsoids are drawn at 50%
probability level. The title compound crystallizes in space
group P21/n with six molecules per unit cell. The unit cell
parameters are: a = 20.5443(4) Å, b = 6.00030(10) Å, c =
10.4847(10) Å, and β = 109.7980(10)°. The final R value was
0.038 based on 4708 reflections. The hydrogen bonding arran-
gements are given in Table 3. The title compound exhibits a
trans arrangement about the N2=N3 and N2A=N3A double
bonds in the solid state, and individual molecules are nearly
1
H 4.59, N 16.06%. H NMR (300 MHz, [D6]DMSO): δ = 3.82 (3 H,
CH3), 6.92–7.52 (8 H, aromatic) and 12.69 for NH group. 13C NMR
(100 MHz, DMSO): δ = 55.5 (O–CH3), 111.8–153.6 (C atoms of aro-
matic rings) ppm. FT-IR (KBr): ν˜ = 3430, 3335, 2107, 1610, 1543, planar. The dihedral angles in both fragments between two
1461, 1256, 1214, 1002, 822 cm–1.
benzene rings are 4.36° and 18.79°, respectively.
On the other hand, the C7–N1–N2–N3, C8–N3–N2–N1,
C7A–N1A–N2A–N3A, and C8A–N3A–N2A–N1A torsion
angles are 173.60(12)°, –6.3(2)°, 5.4(1)°, and 1.8 (3)°, respec-
tively. The N1–N2, N2–N3, N1A–N2A, and N2A–N3A bond
lengths are 1.3297(17) Å, 1.2592(16) Å, 1.3307(18) Å, and
1.2560(17) Å, respectively, which indicate the presence of dis-
tinct single and double bonds between nitrogen atoms and are
in good agreement with the reported data for N=N bond
lengths. In the lattice of the title ligand, the monomeric [R–
NH–N=N–R] moieties are linked to pairs through non-classical
C–H···N hydrogen bonds with C13A···N3 = 3.578(2) Å and
C13A–H8···N3 = 174.01°. Also intramolecular classical N–
H···O hydrogen bonds with N1···O1 = 2.5872(17) Å and
N1A···O1A = 2.5917(17) Å are present in the crystal structure.
The resulted dimeric units are connected with one another by
C–H···π stacking interactions, resulting in the 2D architecture.
These C–H···π stacking interactions are present between CH
Scheme 1.
groups and aromatic rings with H···π distances of 2.82 Å for
C3–H22···Cg1 (3/2–x, –1/2+y, 1/2–z), in which Cg1 is the
centroid for the C2–C7 ring (see Figure 2). The unit cell pack-
2.3 Synthesis of [HgII(C13H11ClN3O)2], HgL2 (2)
ing diagram of the title compound is presented at Figure 3.
The molecular structure of compound 2 is shown in Fig-
To a yellow solution prepared by dissolving [1-(2-methoxyphenyl)-
3-(4-chlorophenyl)]triazene (0.261 g, 1 mmol) in anhydrous methanol
(20 mL), mercury(II) nitrate (0.159 g, 2 mmol) dissolved in anhydrous ure 4. Thermal ellipsoids are drawn at 50% probability level.
Z. Anorg. Allg. Chem. 2012, 798–803
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J. Attar Gharamaleki et al.
ARTICLE
Table 1. Crystal data for compounds 1 and 2.
1
2
Empirical formula
Formula weight
Temperature
C17.33H16Cl1.33N4O1.33
348.94
296
C26H22Cl2HgN6O2
721.99
296
Wavelength
0.71073
0.71073
Crystal system
Space group
monoclinic
P21/n
monoclinic
P21/c
Unit cell dimensions
a = 20.5443(4) Å
b = 6.00030(10) Å
β = 109.7980(10)°
c = 22.1483(4) Å
2568.89(8)
a = 19.2781(16) Å
b = 10.5275(9) Å
β = 98.637(4)°
c = 13.2783(12) Å
2664.3(4)
Volume /Å3
Z
6
4
1.8
6.013
1400
Density (calculated) /Mg·m–3
Absorption coefficient (mm–1)
F(000)
1.353
0.29
1088
θ Range for data collection
Index ranges
2.8 to 27.5 deg
–27 Յ h Յ 27
–7 Յ k Յ 7
–29 Յ l Յ 29
133163/4708
2.2 to 27.2 deg
–24 Յ h Յ 24
–13 Յ k Յ 13
–16 Յ l Յ 16
85027/4951
Reflections collected/unique
[R(int) = 0.026]
multi-scan, Sheldrick, G. M. (2004)
Full-matrix least-squares on F2
4708/ 0 / 336
1.02
[R(int) = 0.035]
multi-scan, Sheldrick, G. M. (2004)
Full-matrix least-squares on F2
4951 / 0 / 337
1.07
Absorption correction
Refinement method
Data/restraints/parameters
Goodness-of-fit on F2
Final R[I Ͼ 2σ(I)]
R1 = 0.038 wR2 = 0.10
R1 = 0.05, wR2 = 0.12
0.21 and –0.2
R1 = 0.017, wR2 = 0.036
R1 = 0.025, wR2 = 0.039
0.52 and –0.58
R indices (all data)
Largest differences in peak and hole /e·A–3
Table 2. Selected bond lengths /Å and angles /° for compounds 1 and 2.
1
O1–C2
O1–C1
N1–N2
N3–N2
1.3692(17)
1.4174(19)
1.3297(17)
1.2592(16)
111.44(12)
O1A–C2A
O1A–C1A
N1A–N2A
N2A–N3A
1.3715(18)
1.4158(19)
1.3307(18)
1.2560(17)
111.53(12)
N3–N2–N1
N3A–N2A–N1A
2
Hg–N3
Hg–N6
Hg–O2
Hg–O1
N3–Hg–N6
N3–Hg–O2
N6–Hg–O2
N1–N2–N3
2.0686(19)
2.0764(19)
2.6731(18)
2.6751(18)
178.53(7)
112.07(7)
66.68(7)
N2–N1
N2–N3
N4–N5
N6–N5
N3–Hg–O1
N6–Hg–O1
O2–Hg–O1
N4–N5–N6
1.273(3)
1.322(3)
1.271(3)
1.322(3)
66.70 (6)
114.66(7)
131.31(7)
112.12(19)
111.72(19)
The title complex crystallized in space group P21/c with four reported in the literature.[36,37] In the lattice of compound 2,
molecules per unit cell. The unit cell parameters are: a = the monomeric [Hg(RNNNR)2] moieties are linked to parallel
19.2781(16) Å, b = 10.5275(9) Å, c = 13.2783(12) Å, and β = chain through C–H···π stacking interactions (Figure 5). These
98.637(4)°. The final R value was 0.017 based on 4951 reflec- C–H···π edge-to-face interactions are present between CH
tions. The HgII atom is coordinated by two symmetrically inde- group of methoxy with aromatic rings with H···π distances of
pendent triazenide ions. Each triazenide ion is coordinated to 3.156 Å and 3.027 Å for C24–H16···Cg2 (x, 1/2–y, 1/2+z) and
central atom through two nitrogen atoms [Hg1–N1
=
C26–H45C···Cg2 [Cg2 = C7–C12], respectively.
2.757(2) Å and Hg1–N3 = 2.0686(19) Å] for one ligand, and
[Hg1–N4 = 2.766(2) Å and Hg1–N6 = 2.0764(19) Å] for the
other one, and one oxygen atom [Hg1–O1 = 2.6751(18) Å, and
Hg1–O2 = 2.6731(18) Å], which are relatively weaker interac-
3.2 Solution Studies
In a typical procedure, the ligand solution (2.0 mL, 5.0ϫ
tion. Hg–O and Hg–N bonds with longer distance have been 10–5 m) in MeOH was placed in the spectrophotometer cell and
800
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Z. Anorg. Allg. Chem. 2012, 798–803

Mercury(II) Complex with [1-(2-Methoxyphenyl)-3-(4-chlorophenyl)]triazene
Figure 1. ORTEP diagram of the structural unit of the ligand 1 with
the atomic numbering scheme. Thermal ellipsoids are drawn at 50%
probability level.
Figure 3. Unit-cell packing diagram of 1 viewed down b axis.
Table 3. Hydrogen bonds and C–H···π interactions arrangement /Å,° for compounds 1 and 2a).
D–H···A
d(D–H)
d(H···A)
d(D···A)
Ͻ(D–H···A)
1
N1A–H55···O1A
N1–H56···O1
C3–H22···Cg1 #1
0.82
0.80
0.93
2.251
2.249
2.820
2.5917(17)
2.5872(17)
3.5779(17)
105.3
106.3
139
2
C24–H16···Cg2 #2
C26–H45C···Cg2 #2
0.93
0.96
3.156
3.027
4.019(3)
3.737(3)
155.3
132
a) Cg1 and Cg2 are the centers of the C2–C7 and C7–C12 rings, respectively. #1 (3/2–x, –1/2+y, 1/2–z); #2 (x, 1/2–y, 1/2+z).
Figure 2. View of supramolecular network formed by C–H···N and C–
H···π interactions in 1.
Figure 4. ORTEP diagram of the structural unit of complex 2 with
the atomic numbering scheme. Thermal ellipsoids are drawn at 50%
probability level.
the absorbance of the solution was measured. Afterwards, a
known amount of the concentrated solution of mercury(II) ni-
trate in MeOH (5.0ϫ10–3 m) was added in a stepwise manner to ligand mole ratio was achieved. The electronic absorption
using a 10 μL Hamilton syringe. The absorbance spectrum of spectra of the ligand in the presence of increasing concentra-
the solution was recorded after each addition. The mercury(II) tion of mercury(II) nitrate at room temperature is shown in
nitrate solution was continuously added until the desired metal Figure 6. The resulting absorbance (at 366 nm) against [Hg2+]/
Z. Anorg. Allg. Chem. 2012, 798–803
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801

J. Attar Gharamaleki et al.
ARTICLE
resulting spectra clearly indicated that the sharp singlet of O–
Me protons observed at δ = 3.82 ppm for ligand, shifted up-
field upon addition of Hg2+ ions to [Hg2+]/[HL] = 0.5 and
shifted down-field upon addition of Hg2+ ions to metal-to-li-
gand molar ratio of about 1.
Figure 5. C–H···π stacking interactions between two [HgL2] moieties
in 2.
[HL] mole ratio plot reveals distinct inflection points at a
metal-to-ligand molar ratio of about 0.5 and 1 emphasizing
the formation of 1:2 and 1:1 complexes. For evaluation of the
conditional formation constants, the mole ratio data obtained
by the physicochemical method employed were fitted to the
previously reported equations,[38,39] using a non-linear least-
squares curve fitting program KINFIT.[40] The conditional for-
mation constants were evaluated as log K1 = 4.78Ϯ0.003 and
log K2 = 4.85Ϯ0.001 for the formation of 1:2 and 1:1 com-
plexes, respectively. For the confirmation of the obtained re-
sults, the complex formation was also investigated by 1H NMR
spectroscopy. In this procedure, the ligand (0.5 mL, 0.005 m)
was dissolved in [D6]DMSO and its spectra was recorded.
Subsequently, a certain amount of the concentrated solution of
mercury(II) nitrate in [D6]DMSO (5.0ϫ10–2 m) was added in
1
a stepwise manner using a 10 μL Hamilton syringe. The H
NMR spectra of the solution were recorded after each addition.
The mercury(II) nitrate solution was continuously added until
the desired metal to ligand mole ratio was achieved. Figure 7
Figure 7. NMR spectra of the ligand [HL] in (C4D8O) (5.0ϫ10–3 m)
in the presence of increasing concentration of mercury(II) nitrate at
room temperature.
1
shows the changes in the H NMR spectra patterns. Distinct
chemical shifts at a metal-to-ligand molar ratio of about 0.5
and 1 confirm the formation of 1:2 and 1:1 complexes. The
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Received: December 30, 2011
Published Online: March 8, 2012
Z. Anorg. Allg. Chem. 2012, 798–803
© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.zaac.wiley-vch.de
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