Synthesis, Characterization and Molecular Structure of Iron(III) Complex with Tridentate Diazene Ligand Having O,N,S Donor Set: Coexistence of Octahedral and Tetrahedral Iron(III) Sites in the Asymmetric Unit

Article abstract of DOI:10.1007/s10870-019-00799-0

Abstract: The reaction of 2-hydroxy-1-(2′-methylthiophenylazo)naphthalene (HL) with iron(II) chloride results in the formation of a hitherto unknown complex, [Fe(L)₂][FeCl₄] (1). The azo-thioether ligand binds iron(III) center throug

Full text of DOI:10.1007/s10870-019-00799-0

Journal of Chemical Crystallography
https://doi.org/10.1007/s10870-019-00799-0
ORIGINAL PAPER
Synthesis, Characterization and Molecular Structure of Iron(III)
Complex with Tridentate Diazene Ligand Having O,N,S Donor
Set: Coexistence of Octahedral and Tetrahedral Iron(III) Sites
in the Asymmetric Unit
Purak Das1 · Achintesh Narayan Biswas2
Received: 12 November 2016 / Accepted: 18 July 2019
©
Springer Science+Business Media, LLC, part of Springer Nature 2019
Abstract
The reaction of 2-hydroxy-1-(2′-methylthiophenylazo)naphthalene (HL) with iron(II) chloride results in the formation of a
−
hitherto unknown complex, [Fe(L) ][FeCl ] (1). The azo-thioether ligand binds iron(III) center through the O ,N,S donor set
2
4
+
to form the octahedral [Fe(L) ] cation. Solid state molecular structure of (1) has been determined by single crystal X-ray dif-
2
fraction technique. Compound (1) crystallizes in the monoclinic P2 /c space group of unit cell dimensions a=10.3904(19) Å,
1
b=23.735(4) Å, c=15.815(3) Å; α=90°, β=102.248(4)°, γ=90° and Z=4. The structure was solved by direct method and
III
reꢀned to R value 0.0975 on 3796 observed reꢁections. There are one octahedral cationic unit of [Fe L ], a tetrahedral
1
2
III
anionic unit of [Fe Cl ] and 0.5(C H OH) as solvent molecules in an asymmetric unit of the crystal lattice of (1). There
4
2
5
2
are two intramolecular C–H⋯O interactions and the crystal packing is stabilized by interionic C–H⋯Cl and intermolecular
C–H⋯Cg interactions.
Graphic Abstract
Single crystal X-ray diffraction study of an iron(III) complex bearing an azo-thioether ligand, 2-hydroxy-1-(2′-
III
+
III
−
methylthiophenylazo)naphthalene (HL) is presented, crystal packing of the complex, [Fe L ] [Fe Cl ] (1) has been
2
4
found to be stabilized by interionic C–H⋯Cl and intermolecular C–H⋯Cg interactions.
Keywords Crystal structure · Iron(III) complex · Arylazo · O,N,S donor set · Ionic complex
*
Purak Das
purakdas@gmail.com
Extended author information available on the last page of the article
Vol.:(0
1
123456789)
3

Journal of Chemical Crystallography
Introduction
and characterization of an iron(III) complex bearing
2
-hydroxy-1-(2′-methylthiophenylazo)naphthalene (HL).
In biology, enzymes having iron–sulfur co-factors play
crucial roles in mediating electron transfer processes [1,
The solid-state structure of complex (1) has been char-
acterized by single crystal X-ray diꢂraction. The ligand
has been found to bind iron(III) center in a tridenate fash-
2
]. Nitrile hydratases (NHases), a class of thiolate-ligated
+
non-heme iron enzymes are known to catalyze the enan-
tioselective hydrolysis of nitriles to amides [3–7]. The
sulfur rich iron centers in the cofactor of FeMo nitoge-
nase play important role in the ꢀxation of nitrogen [8, 9].
Given their biological signiꢀcance, signiꢀcant research
eꢂort has been devoted for the development of synthetic
models [10–13]. In this regard, a class of dinitrogen com-
plexes of sulfur-ligated iron were reported by Takaoka
et al. as models of the local environment of the iron cent-
ers in the FeMo cofactor [10]. Kovacs and coworkers have
reported a rare example of metal-assisted oxygen atom
addition to an Fe(III)-thiolate complex [11]. In this case,
the thiolated ligated Fe(II) complex has been shown to
react with O-atom donors to form an oxygenated sulfenate,
which resembles a proposed intermediate formed during
catalytic turnovers in cysteinatedioxygenases (CDO) and
nitrile hydratases (NHases) [11]. Moreover, metal com-
plexes with O,N,S donor set are of much interest to the
fundamental, medicinal and applied chemistry [14–18].
Several transition metal complexes based on Schiꢂ base
or thiosemicarbazone ligands having O,N,S donor set
have been reported to possess medicinal and enzymatic
activities [19–23]. Additionally transition metal com-
plexes based on azo ligands display several interesting
properties [24–27]. In continuation of our interest in the
structure and properties of complexes bearing diazene
ligands [26, 28], we herein wish to report the synthesis
ion resulting formation of a pseudo-octahedral [Fe(L)2]
−
cation along with a [FeCl4] counter anion.
Experimental Section
Materials and Physical Measurements
2-Aminothiophenol (Merck, Germany) and 2-naphthol
(E. Merck, India) were used without further puriꢀcation.
Anhydrous ferrous chloride, methyl iodide and all other
chemicals were reagent grade commercial materials and
were used as received. C, H and N elemental analyses were
done by Heraeus Carlo Erba 1108 elemental analyzer.
Preperation of Ligand (HL)
2-Hydroxy-1-(2′-methylthiophenylazo)naphthalene (HL)
was prepared using 2-naphthol and 2-thiomethylaniline fol-
lowing reported procedure [24].
III
+
III
−
Isolation of [Fe L2] [Fe Cl4] (1)
Solid 2-hydroxy-1-(2′-methylthiophenylazo)naphthalene
(HL) (0.03 g, 0.1 mmol) in ethanol (30 ml) was taken in
a round bottomed ꢁask ꢀtted with a condenser. To it an
Scheme 1 Synthesis of the iron complex (1) of the ligand HL. (i) Conc. H SO cooled to −10 °C; (ii) NaNO ; (iii) aqueous NaOH cooled to
2
4
2
−
10 °C; (iv) X is slowly added to Y with constant stirring
1
3

Journal of Chemical Crystallography
Table 1 Crystal data collection and structure reꢀnement for (1)
suitable for X-ray diꢂraction. (Yield: 0.060 g, 0.0685 mmol,
6
3
8.5%). Anal. calc. for C H N O S Cl Fe : C, 48.79%; H,
36 32 4 3 2 4 2
Crystal data
.64%; N, 6.32%. Found: C, 50.2%; H, 3.2%; N, 6.2%.
CCDC reference number
Empirical formula
Moiety formula
CCDC-1515207
C H N O S Cl Fe
3
6
32
4
3
2
4
2
Crystallographic Study
FeC H N O S , FeCl ,
3
4
26
4
2
2
4
0
.5(C H OH)
2 5 2
A single crystal of 1 suitable for X-ray diffraction was
mounted on a Bruker SMART-APEX CCD diꢂractometer
and the diꢂraction data was collected using monochromatic
Mo Kα radiation (λ = 0.71073 Å) with the ω and φ scan
technique. The unit cell was determined using SMART [29],
the diꢂraction data were integrated with Bruker SAINT sys-
tem [29] and the data were corrected for absorption using
SADABS [29]. The structure was solved using SHELXS
Formula weight
Crystal system
Space group
Colour, habit
Size, mm
Unit cell dimensions
a=10.3904(19) Å
b=23.735(4) Å
886.27
Monoclinic
P2 /c
1
Roseate brown, rod
0.31×0.28×0.26
α=90°
β=102.248(4)°
γ=90°
3811.5(12)
4
1.544
1.193
9
7 [30] by direct method and was reꢀned by full matrix
c=15.815(3) Å
2
Volume Å3
least squares based on F using SHELXL-2018/3 [31]. All
the H atoms were included at calculated positions as riding
Z
2
3
3
atoms with C(sp )–H distances of 0.93 Å, C(sp )–H dis-
Density (calculated), mg/m
3
Absorption coeꢃcient, mm−
1
tances of 0.96 Å and O(sp )–H distances of 0.82 Å. Some
low-angle reꢁections were excluded from the reꢀnement,
as they were probably obscured by the beam stop. ORTEP-
plot and packing diagram were generated with ORTEP-3 for
Windows [32]. WinGX [32] was used to prepare the material
for publication.
F(000)
Data collection
Temperature, K
Theta range for data collection 2.754° to 24.499°
Index ranges
1808
293(2)
−12≤h≤12
−
−
27≤k≤27
18≤l≤18
Results and Discussion
Reꢁections collected
Unique reꢁections
31,891
5891
The compound 1 was synthesized following the reaction of
Observed reꢁections (>2σ(I)) 3796
2
-hydroxy-1-(2′-methylthiophenylazo)naphthalene (HL)
Rint
0.1410
24.499°, 92.9
Multi-scan (SADABS; Bruker,
000)
[
24] and anhydrous FeCl in ethanol at 60 °C (Scheme 1).
2
Completeness to θ, %
Absorption correction
Single crystals suitable for X-ray diꢂraction studies were
obtained by slow vapor diꢂusion of dichloromethane onto
a solution of complex 1 in benzene. Previously, we had
reported the synthesis and characterization of square-planar
2
Tmin =0.689, Tmax =0.708
Reꢀnement
Full-matrix least-squares on F2
5891/0/464
2+
2+
2+
Reꢀnement method
Data/restraints/parameters
Calculated weights, w
complexes [MLX] (M=Ni , Pd and Pt ) (X=Cl) bear-
ing the azo-thioether ligand (HL) [24, 28, 33]. Unlike the
group eight metal complexes, two deprotonated ligands have
been found to bind the iron(III) center to form a pseudo octa-
2
2
2
1/[σ (F )+(0.1084P) +12.6351P]
o
2
2
where P=(F +2F )/3
o
c
Goodness-of-ꢀt on F2
Final R indices [I>2σ(I)]
R indices (all data)
1.031
R =0.0975, wR =0.2007
III
+
hedral cationic species, [Fe L ] , along with a tetrahedral
2
III
−
1
2
counter anion, [Fe Cl ] .
4
III
+
III
−
R =0.1534, wR =0.2312
1
2
The iron(III) complex [Fe L ] [Fe Cl ] crystal-
2 4
−
3
Largest diꢂ. peak and hole
1.144 and −0.841 e.Å
lizes in the monoclinic P2 /c space group along with
1
0
.5(C H OH) in the asymmetric part of the unit cell.
2 5 2
Crystal data and experimental details for (1) are listed
in Table 1. Selected bond lengths and torsion angles are
presented in Table 2. The asymmetric unit consisting of
ethanolic (10 ml) solution of anhydrous FeCl (0.013 g,
2
0
.1 mmol) was added and the solution was stirred for 4 h
III
+
at 60 °C to aꢂord a roseate browncolor solution. The sol-
vent was removed under reduced pressure and the solid was
washed with cold water and then with ethanol to remove
an octahedral cation, [Fe L ] and a tetrahedral anion,
2
III
−
[Fe Cl ] , has been shown in Fig. 1 (solvent molecules
4
have been omitted for clarity). Three dimensional packing
unreacted FeCl and HL. The roseate brown solid (complex
arrangement of the ionic complex 1 has been shown in
2
III
1
) was then recrystallized from dichloromethane solution
Fig. 2. The central metal Fe exhibits a distorted octahe-
−
through slow diꢂusion into benzene to aꢂord single crystals
dral geometry on binding with two L as reꢁected from
1
3

Journal of Chemical Crystallography
Table 2 Selected bond lengths
Bond lengths (Å)
Fe(1)–O(1)
Fe(1)–O(2)
(
Å), bond angles (°) and torsion
1.870(5)
1.884(5)
1.921(6)
1.929(6)
2.290(2)
2.295(2)
N(2)–N(1)
N(4)–N(3)
Fe(2)–Cl(3)
Fe(2)–Cl(1)
Fe(2)–Cl(2)
Fe(2)–Cl(4)
1.284(9)
1.287(9)
2.160(5)
2.178(4)
2.201(4)
2.206(6)
angles (°) for (1)
Fe(1)–N(2)
Fe(1)–N(4)
Fe(1)–S(1)
Fe(1)–S(2)
Bond angles (°)
O(1)–Fe(1)–O(2)
O(1)–Fe(1)–N(2)
O(2)–Fe(1)–N(2)
O(1)–Fe(1)–N(4)
O(2)–Fe(1)–N(4)
O(2)–Fe(1)–S(1)
N(2)–Fe(1)–S(1)
N(4)–Fe(1)–S(1)
O(1)–Fe(1)–S(2)
Torsion angles (°)
N(1)–N(2)–C(11)–C(12)
N(2)–N(1)–C(1)–C(2)
91.2(2)
93.1(3)
87.6(3)
86.4(2)
91.4(3)
91.82(18)
86.9(2)
93.7(2)
92.90(18)
N(2)–Fe(1)–S(2)
N(4)–Fe(1)–S(2)
S(1)–Fe(1)–S(2)
Cl(3)–Fe(2)–Cl(1)
Cl(3)–Fe(2)–Cl(2)
Cl(1)–Fe(2)–Cl(2)
Cl(3)–Fe(2)–Cl(4)
Cl(1)–Fe(2)–Cl(4)
Cl(2)–Fe(2)–Cl(4)
94.6(2)
86.5(2)
84.06(8)
112.6(3)
102.93(18)
109.42(15)
114.0(4)
110.55(17)
106.9(2)
−170.6(7)
4.0(11)
N(3)–N(4)–C(28)–C(29)
N(4)–N(3)–C(18)–C(19)
−163.6(6)
15.0(11)
Fig. 1 The asymmetric unit
of (1), with displacement
ellipsoids drawn at the 50%
probability level. The solvent
molecules have been omitted
for clarity
the bond lengths and bond angles around the central FeIII
of the cationic unit (Table 2). The tetrahedral anionic
part of the ionic crystal of (1) is also found to be dis-
torted (Table 2) in nature. There is disorder in the solvent
ethanol molecules, two ethanol molecules are oriented in
opposite directions resulting in a ring like structure. The
from the torsion angles (Table 2). In the cationic unit of
1 Fe(1)–O(2), Fe(1)–N(4) and Fe(1)–S(2) bonds encoun-
tered greater lengths compared to Fe(1)–O(1), Fe(1)–N(2)
and Fe(1)–S(1) bonds respectively (Table 2). In the ani-
onic unit of complex 1, Fe–Cl bond lengths ranges from
2.16 to 2.21 Å and Cl–Fe–Cl bond angles ranges from
102.93° to 114.0° (Table 2) showing signiꢀcant deviation
from the regular tetrahedral geometry [34–36], clearly
ligand which is a planner molecule excluding the S–CH
3
unit loses its planarity on binding the metal ion. There is
puckering in the ligand backbone along the –N=N– bond.
The puckering is more pronounced in the ligand frame
containing the N3 and N4 nitrogen atoms as reꢁected
III
indicating a distorted tetrahedral geometry around Fe of
the anionic unit of 1. The solid state structure exhibits two
intramolecular C–H⋯O interaction (Table 3; Fig. 3). The
1
3

Journal of Chemical Crystallography
Fig. 2 The molecular arrange-
ment of (1) in the bc plane
Table 3 Hydrogen bonded geometries in (1)
Table 4 X–H···Cg interactions in (1)
Bond
D–H
H···A
D···A
D–H···A
X–H···Cg
H···Cg Hperp
γ
X–H···Cg X···Cg
iii
iv
C(34)–H(34A)···O(1)
C(17)–H(17A)···O(2)
C(32)–H(32)···Cl(1)
C(4)–H(4)···Cl(2)i
0.96
0.96
0.93
0.93
0.93
0.93
2.49
2.60
2.82
2.81
2.72
2.76
2.957(11)
2.984(12)
3.575(9)
3.464(10)
3.492(11)
3.546(14)
110
104
139
128
141
144
C(3)–H(3)···Cg(13)
C(3)–H(3)···Cg(13)
2.85
2.85
2.90
2.83
2.78
2.83 06.88 166
−2.83 06.88 166
−2.71 20.44 130
2.80 07.93 154
2.72 11.46 163
3.753(11)
3.753(11)
3.562(10)
3.690(12)
3.680(8)
iv
v
C(4)–H(4)···Cg(7)
C(6)–H(6)···Cg(8)
C(20)–
ii
C(8)–H(8)···Cl(3)
iv
ii
H(20)···Cg(10)
C(16)–H(16)···Cl(3)
C(22)–
2.78
2.94
−2.62 19.53 130
2.88 11.04 133
3.454(9)
Symmetry codes: (i) −1+x, y, −1+z; (ii) 1−x, 1/2+y, 1/2−z
vi
H(22)···Cg(5)
C(34)–
3.660(10)
vii
H(34B)···Cg(9)
(
iii)
(iv)
Symmetry codes:
1−x, −1/2+y, 1/2−z;
(vii)
x, 1/2−y, −1/2+z;
−1+x, y, z
(
v)
(vi)
−
1+x, 1/2−y, −1/2+z;
1+x, y, z;
Cg5, Cg7, Cg8, Cg9, Cg10 and Cg13 are the centroids of the C1–
C10, C11–C16, C18–C27, C22–C26, C28–C33 and O3–C36 (sym-
metry generated ring of solvent molecules) rings respectively
crystal packing is stabilized by four interionic C–H⋯Cl
interactions (Table 3; Fig. 3) and seven intermolecular
C–H···Cg interactions (Table 4; Figs. 4, 5, 6). Figure 4
shows the C–H⋯Cg interaction between the H3 hydrogen
of the naphthyl ring and the cage generated via the orien-
tation of the two disordered solvent ethanol molecules.
The asymmetric unit contains 50% of the solvent mol-
ecules and the rest 50% is generated through the sym-
metry operation. Two C–H⋯Cg interactions between the
Fig. 3 Dotted lines indicate the intramolecular C–H···O and interionic
C–H···Cl interactions in (1)
1
3

Journal of Chemical Crystallography
Fig. 4 Dotted line indicates the C–H···Cg interaction in the cationic
unit and the cage generated by disordered solvent molecules of (1)
Fig. 6 Dotted lines indicate other intermolecular C–H···Cg interac-
tions in the cationic units of (1)
anionic part of (1) and also C–H⋯Cg interactions between
the naphthyl H and the phenyl cage of (1) which results the
complete ionic crystal in (1). A space-ꢀll model of growth
Fig. 5 Dotted lines indicate the intermolecular C–H···Cg interactions
between naphthyl H and phenyl cage in the cationic units of (1)
III
+
III
−
of [Fe L ] [Fe Cl ] in one dimension has been shown
2
4
in Fig. 7 (solvent molecules have been omitted for clarity).
naphthyl H and the phenyl cage (Table 4) are shown in
Fig. 5. Other three C–H⋯Cg interactions (Table 4; Fig. 6)
per asymmetric cationic unit of (1) result in the growth of
the molecular assembly in two dimensions. Therefore two
dimensional growth of the crystal is encountered through
the C–H⋯Cg interactions between the cationic part and
also the cationic part and the solvent molecule whereas
the third dimension in the crystal packing is the contribu-
tion of the C–H⋯Cl interactions between cationic and the
Conclusion
Synthesis and solid state structure of an iron(III) complex
bearing an azo-thioether ligand are reported. The azo-
−
thioether ligand binds iron(III) center through the O ,N,S
+
donor set to form the octahedral [Fe(L) ] cation along
2
III
−
with a tetrahedral counter anion, [Fe Cl ] . The solid state
4
structure exhibits two intramolecular C–H···O interactions.
1
3

Journal of Chemical Crystallography
Fig. 7 Spaceꢀll model of growth of (1) in one dimension. The solvent molecule has been omitted for clarity
The crystal packing is stabilized by C–H···Cl interactions
between opposite ions, C–H···Cg interactions between the
cationic units and C–H···Cg interactions between the cati-
onic unit and the solvent molecules.
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Crystallographic data for structural analysis of (1) has been
deposited at the Cambridge Crystallographic Data Centre,
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obtained from the Director, CCDC, 12 Union Road, Cam-
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Acknowledgements The authors thank Dr. P. Bandyopadhyay, Depart-
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sary laboratory facilities and Professor S. Pal, School of Chemistry,
University of Hyderabad, India, for the X-ray crystallographic data
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jurisdictional claims in published maps and institutional aꢃliations.
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Journal of Chemical Crystallography
Aꢀliations
Purak Das1 · Achintesh Narayan Biswas2
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Department of Chemistry, Rishi Bankim Chandra College
Department of Chemistry, National Institute of Technology
Sikkim, South Sikkim, Ravangla, Sikkim 737139, India
for Women, Naihati, West Bengal 743165, India
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