Synthesis, Characterization, and Crystal Structures of Oxidovanadium(V) Complexes Derived from 2-Chloro-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide with Antimicrobial Activity

Article abstract of DOI:10.1134/S1070328419040109

Abstract: Two new oxodovanadium(V) complexes, [VO(L)(OEt)(MeOH)] (I) and [VO(L)(Bha)] · EtOH (II), where L is the anion of 2-chloro-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide (H₂L), Bha is the anion of 2-hydroxybenzohydroxamic acid (HBha), were prepared and characterized by IR, UV-Vis and?single crystal X-ray determination (CIF files CCDC nos. 1840661 (I) and 1840662 (II)). Complex I crystallizes as the monoclinic space group P2₁/c with unit cell dimensions a = 8.272(1), b = 21.326(2), c = 12.979(1) ?, β = 107.173(2)°, V = 2187.5(4) ?³, Z = 4, R₁ = 0.0811, wR₂ = 0.2152, GOOF = 1.048. Complex?II?crystallizes as the triclinic space group P 1 with unit cell dimensions a = 7.407(2), b = 14.195(2), c = 14.330(2) ?, α?= 117.262(2)°, β = 92.947(2)°, γ = 95.771(2)°, V = 1324.4(4) ?³, Z = 2, R₁ = 0.0919, wR₂?= 0.1539, GOOF?= 0.986. X-ray analysis indicates that the complexes are mononuclear vanadium(V) species, with the V atoms in octahedral coordination. The complexes were evaluated for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence) and antifungal (Candida albicans and Aspergillus niger) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. The two complexes have from medium to strong activities against B. subtilis, S. aureus, and E.?coli.

Full text of DOI:10.1134/S1070328419040109

ISSN 1070-3284, Russian Journal of Coordination Chemistry, 2019, Vol. 45, No. 5, pp. 378–384. © Pleiades Publishing, Ltd., 2019.
Synthesis, Characterization, and Crystal Structures
of Oxidovanadium(V) Complexes Derived from 2-Chloro-N'-(3,5-
Dichloro-2-Hydroxybenzylidene)benzohydrazide
with Antimicrobial Activity
S. M. Wua, X. Y. Qiua, *, J. C. Wangb, S. J. Liua, and L. Y. Hea
aCollege of Science & Technology, Ningbo University, Ningbo, 315212 P.R. China
bCollege of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, 250014 P.R. China
*e-mail: xiaoyang_qiu@126.com
Received May 1, 2018; revised July 26, 2018; accepted September 20, 2018
Abstract—Two new oxodovanadium(V) complexes, [VO(L)(OEt)(MeOH)] (I) and [VO(L)(Bha)] · EtOH
(II), where L is the anion of 2-chloro-N'-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide (H2L), Bha
is the anion of 2-hydroxybenzohydroxamic acid (HBha), were prepared and characterized by IR, UV-Vis
and single crystal X-ray determination (CIF files CCDC nos. 1840661 (I) and 1840662 (II)). Complex I crys-
tallizes as the monoclinic space group P21/c with unit cell dimensions a = 8.272(1), b = 21.326(2), c =
12.979(1) Å, β = 107.173(2)°, V = 2187.5(4) Å3, Z = 4, R1 = 0.0811, wR2 = 0.2152, GOOF = 1.048.
Complex II crystallizes as the triclinic space group P with unit cell dimensions a = 7.407(2), b = 14.195(2),
1
c = 14.330(2) Å, α = 117.262(2)°, β = 92.947(2)°, γ = 95.771(2)°, V = 1324.4(4) Å3, Z = 2, R1 = 0.0919, wR2 =
0.1539, GOOF = 0.986. X-ray analysis indicates that the complexes are mononuclear vanadium(V) species,
with the V atoms in octahedral coordination. The complexes were evaluated for their antibacterial (Bacillus
subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence) and antifungal (Candida albi-
cans and Aspergillus niger) activities by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bro-
mide) method. The two complexes have from medium to strong activities against B. subtilis, S. aureus, and
E. coli.
Keywords: hydrazone, vanadium complex, mononuclear complex, crystal structure, antimicrobial activity
DOI: 10.1134/S1070328419040109
INTRODUCTION
H
Hydrazones containing CH=N–NH–C(O) group
are a kind of biological active compound. The com-
pounds have attracted remarkable attention for their wide
range of biological activities, such as antibacterial [1–3],
antifungal [4, 5], and antitumor [6, 7]. It was reported
that hydrazones bearing electron-withdrawing groups
can improve their antimicrobial activities [8, 9]. Rai and
co-workers reported a series of fluoro, chloro, bromo,
and iodo-substituted compounds, and found that they
have significant antimicrobial activities [10]. Vanadium
complexes with Schiff bases and hydrazones have been
Cl
N
N
O
Cl
OH
Cl
(H2L)
EXPERIMENTAL
Materials and methods. Vanadyl acetylacetonate
reported to have interesting antibacterial activities [11– and organic materials were purchased from Sigma-
14]. As a continuation of work on the exploration of novel Aldrich and used as received. All other reagents were
complex based antimicrobial agents, in this paper, two of analytical reagent grade. Elemental analyses of C,
new oxodovanadium(V) complexes, [VO(L)(OEt)- H, and N were carried out in a Perkin-Elmer
(MeOH)] (I) and [VO(L)(Bha)] · EtOH (II), where L is automated model 2400 Series II CHNS/O analyzer.
the anion of 2-chloro-N'-(3,5-dichloro-2-hydroxyben- FT-IR spectra were obtained on a Perkin-Elmer 377
zylidene)benzohydrazide (H2L), Bha is the anion of FT-IR spectrometer with samples prepared as KBr
pellets. UV-Vis spectra were obtained on a Lambda
2-hydroxybenzohydroxamic acid (HBha), have been
presented.
1
900 spectrometer. H NMR data were recorded on a
378

SYNTHESIS, CHARACTERIZATION, AND CRYSTAL STRUCTURES
379
Bruker 300 MHz spectrometer. X-ray diffraction was ArH), 7.55–7.38 (m., 6H, ArH), 7.25 (t., 1H, ArH),
carried out on a Bruker APEX II CCD diffractometer. 6.83 (d., 1H, ArH).
Synthesis of H2L. To the methanolic solution
(30 mL) of 2-chlorobenzohydrazide (0.01 mol, 1.70 g)
was added a methanolic solution (30 mL) of 3,5-
dichlorosalicylaldehyde (0.01 mol, 1.90 g) with stir-
ring. The mixture was stirred for 30 min at room tem-
perature, and left to slowly evaporate to give crystalline
product, which were obtained by filtration. The yield
was 92%.
For C23H19N3O7Cl3V
Anal. calcd., %
Found, %
C, 45.53
C, 45.67
H, 3.16
H, 3.05
N, 6.93
N, 7.10
X-ray crystallography. X-ray diffraction was carried
out at a Bruker APEX II CCD area diffractometer
equipped with MoKα radiation (λ = 0.71073 Å). The
collected data were reduced with SAINT [15], and
multi-scan absorption correction was performed using
SADABS [16]. The structures of the complexes were
solved by direct method, and refined against F 2 by
full-matrix least-squares method using SHELXTL
[17]. All of the non-hydrogen atoms were refined
anisotropically. The methanol hydrogen in I and
amino hydrogen atom in II were located from elec-
tronic density maps and refined isotropically. The
remaining hydrogen atoms were placed in calculated
positions and constrained to ride on their parent
atoms. The crystallographic data and refinement
parameters for the compounds are listed in Table 1.
Selected bond lengths and angles are listed in Table 2.
IR data (ν, cm–1): 3455 (OH), 3323 (NH), 1657
(C=O), 1602 (C=N). UV-Vis data (MeOH; λmax
,
1
nm): 295, 332. H NMR (300 MHz; d6-DMSO; δ,
ppm): 12.52 (s., 1H, OH), 12.39 (s., 1H, NH), 8.56 (s.,
1H, CH=N), 7.69–7.60 (m., 2H, ArH), 7.55–7.37
(m., 4H, ArH).
For C14H9N2O2Cl3
Anal. calcd., %
Found, %
C, 48.94
C, 49.17
H, 2.64
H, 2.75
N, 8.15
N, 8.06
Synthesis of complex I. H2L (1.0 mmol, 0.343 g)
and vanadyl acetylacetonate (1.0 mmol, 0.265 g) were
mixed in a mixture of methanol (30 mL) and ethanol
(20 mL). The mixture was refluxed for 1 h and then
cooled to room temperature. Single crystals of the
complex, suitable for X-ray diffraction, were formed
upon slowly evaporation within a few days. The crys-
tals were isolated by filtration. The yield was 38%.
Supplementary material for structures has been
deposited with the Cambridge Crystallographic Data
Centre (CCDC nos. 1840661 (I) and 1840662 (II);
deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.
ac.uk).
Antimicrobial assay. The antibacterial activities of
the free hydrazone compound and the complexes were
tested against B. subtilis, S. aureus, E. coli, and P. f luo-
rescence using MH (Mueller–Hinton) medium. The
antifungal activities of the compounds were tested
against C. albicans and A. niger using RPMI-1640
medium. The MIC values of the tested compounds
were determined by a colorimetric method using the
dye MTT [18]. A stock solution of the compound
(150 μg mL–1) in DMSO was prepared and
graded quantities (75, 37.5, 18.8, 9.4, 4.7, 2.3, 1.2,
0.59 μg mL–1) were incorporated in specified quantity
of the corresponding sterilized liquid medium. A spec-
ified quantity of the medium containing the com-
pound was poured into micro-titration plates. Suspen-
sion of the microorganism was prepared to contain
approximately 1.0 × 105 cfu mL–1 and applied to
microtitration plates with serially diluted compounds
in DMSO to be tested and incubated at 37°C for 24
and 48 h for bacterial and fungi, respectively. Then the
MIC values were visually determined on each of the
microtitration plates, 50 μL of PBS (phosphate buff-
ered saline 0.01 mol L–1, pH 7.4) containing 2 mg of
MTT mL–1 was added to each well. Incubation was
continued at room temperature for 4–5 h. The content
of each well was removed and 100 μL of isopropanol
IR data (ν, cm–1): 3387 (OH), 1605 (C=N), 949
(V=O). UV-Vis data (CH3CN; λmax, nm): 260, 325,
1
407. H NMR (300 MHz; d6-DMSO; δ, ppm): 8.91
(s., 1H, CH=N), 7.83 (d., 1H, ArH), 7.55–7.38 (m.,
5H, ArH), 3.46 (q., 2H, OCH2CH3), 3.35 (s., 3H,
CH3OH), 1.07 (t., 3H, OCH2CH3).
For C17H16N2O5Cl3V
Anal. calcd., %
Found, %
C, 42.05
C, 42.23
H, 3.32
H, 3.43
N, 5.77
N, 5.66
Synthesis of complex II. Complex I (0.1 mmol,
48.6 mg) and 2-hydroxybenzohydroxamic acid
(0.1 mmol, 15.3 mg) were mixed in ethanol (15 mL).
The mixture was refluxed for 30 min and then cooled
to room temperature. Single crystals of the complex,
suitable for X-ray diffraction, were formed upon
slowly evaporation within a few days. The crystals were
isolated by filtration. The yield was 57%.
IR data (ν, cm–1): 3392 (OH), 3217 (NH), 1641
(C=O), 1605 (C=N), 950 (V=O). UV-Vis data
(CH3CN; λmax, nm): 255, 333, 410. 1H NMR
(300 MHz; d6-DMSO; δ, ppm): 12.17 (s., 1H, OH), containing 5% 1 mol L–1 HCl was added to extract the
8.91 (s., 1H, CH=N), 7.92 (d., 1H, ArH), 7.83 (d., 1H, dye. After 12 h of incubation at room temperature, the
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WU et al.
Table 1. Crystallographic and refinement data for the complexes I and II
Value
Complex
I
II
Formula weight
Crystal shape/color
T, K
485.61
Block/brown
298(2)
606.70
Block/brown
298(2)
Crystal dimensions, mm
Crystal system
Space group
0.18 × 0.15 × 0.15
Monoclinic
P21/c
0.21 × 0.20 × 0.17
Triclinic
P1
a, Å
b, Å
c, Å
8.272(1)
21.326(2)
12.979(1)
90
107.173(2)
90
7.407(2)
14.195(2)
14.330(2)
117.262(2)
92.947(2)
95.771(2)
1324.4(4)
α, deg
β, deg
γ, deg
V, Å3
2187.5(4)
Z
4
2
ρ
calcd, g cm–3
1.475
1.521
μ(MoKα), mm–1
0.849
0.724
F(000)
984
616
Measured reflections
Unique reflections
Observed reflections (I ≥ 2σ(I))
Min. and max. transmission
Parameters
12725
4055
2221
0.8622 and 0.8833
6802
4639
1855
0.8628 and 0.8868
257
3
341
1
Restraints
Goodness of fit on F 2
R1, wR2 (I ≥ 2σ(I))*
R1, wR2 (all data)*
1.048
0.986
0.0811, 0.2152
0.1427, 0.2603
0.0919, 0.1539
0.2233, 0.2042
2
2
2 1/2
* R = F – F /F , wR = [∑ w(
–
2)/∑ w( ) ]
.
Fo Fc
Fo
1
o
c
o
2
optical density was measured with a microplate reader
at 550 nm.
In the spectra of the free hydrazone compound and
the complexes, the weak and broad bands centered at
about 3400 cm–1 are assigned to the vibration of O–H
bonds. The weak and sharp bands located at 3323 cm–1 of
the free hydrazone compound and 3217 cm–1 of com-
plex II are assigned to the vibration of N–H bonds.
The intense bands at 1657 cm–1 of H2L and 1641 cm–1
of complex II are generated by ν(C=O) vibrations,
whereas the bands at 1602–1606 cm–1 by the ν(C=N)
ones. The non-observation of the ν(C=O) bands,
present in the spectrum of the hydrazone compounds,
indicates the enolization of the amide functionality
upon coordination to the V-center. Instead strong
bands at 1605 cm–1 for the complexes are observed,
which can be attributed to the asymmetric stretching
vibration of the conjugated CH=N–N=C–O groups,
RESULTS AND DISCUSSION
The hydrazone compound H2L was readily pre-
pared by the condensation reaction of 3,5-dichlorosa-
licylaldehyde with 2-chlorobenzohydrazide in metha-
nol. Complex I was prepared by the reaction of the
hydrazone compound with vanadyl acetylacetonate in
methanol and ethanol. Complex II was prepared
by reaction of complex I with HBha in ethanol. Com-
plex II can also be prepared by the reaction of the
hydrazone compound with vanadyl acetylacetonate
and HBha in ethanol. Elemental analyses of the com-
plexes are in accordance with the molecular structures
proposed by the X-ray analysis.
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SYNTHESIS, CHARACTERIZATION, AND CRYSTAL STRUCTURES
381
Table 2. Selected bond distances (Å) and angles (deg) for the complexes I and II
Bond
d, Å
Bond
d, Å
I
V(1)–O(1)
V(1)–O(3)
V(1)–O(5)
1.869(4)
1.575(5)
2.324(5)
V(1)–O(2)
V(1)–O(4)
V(1)–N(1)
1.954(5)
1.756(4)
2.124(5)
II
V(1)–O(1)
V(1)–O(3)
V(1)–O(6)
1.915(6)
2.244(6)
1.593(5)
V(1)–O(2)
V(1)–O(4)
V(1)–N(1)
1.967(5)
1.871(5)
2.087(6)
Angle
ω, deg
Angle
ω, deg
I
O(3)V(1)O(4)
O(4)V(1)O(1)
O(4)V(1)O(2)
O(3)V(1)N(1)
O(1)V(1)N(1)
O(3)V(1)O(5)
O(1)V(1)O(5)
N(1)V(1)O(5)
101.8(2)
100.3(2)
97.0(2)
95.3(2)
83.0(2)
174.8(2)
82.5(2)
79.7(2)
O(3)V(1)O(1)
O(3)V(1)O(2)
O(1)V(1)O(2)
O(4)V(1)N(1)
O(2)V(1)N(1)
O(4)V(1)O(5)
O(2)V(1)O(5)
98.3(3)
98.3(2)
152.9(2)
161.9(2)
74.2(2)
83.0(2)
79.1(2)
II
O(6)V(1)O(4)
O(4)V(1)O(1)
O(4)V(1)O(2)
O(6)V(1)N(1)
O(1)V(1)N(1)
O(6)V(1)O(3)
O(1)V(1)O(3)
N(1)V(1)O(3)
95.0(2)
104.7(2)
91.5(2)
100.0(2)
84.0(2)
171.2(2)
82.8(2)
88.6(2)
O(6)V(1)O(1)
O(6)V(1)O(2)
O(1)V(1)O(2)
O(4)V(1)N(1)
O(2)V(1)N(1)
O(4)V(1)O(3)
O(2)V(1)O(3)
100.0(3)
99.9(3)
153.1(2)
161.2(2)
74.8(2)
76.2(2)
80.3(2)
characteristic for the coordination of the enolate form
of the compounds. The strong ν(V=O) bands at
949 cm–1 for I and 950 cm–1 for II could be clearly
identified for both complexes [19].
Molecular structure of complex I is shown in
Fig. 1a. The coordination geometry around the vana-
dium atom can be described as a distorted octahedral
with the tridentate hydrazone ligand coordinated in a
meridional fashion, forming five- and six-membered
chelate rings with bite angles of 74.2(2)° and 83.0(2)°,
respectively, typical for this type of ligand systems
[20]. The chelating hydrazone ligand lies in a plane
with one ethanolato ligand which lies trans to the
hydrazone imino N atom. One methanol O atom trans
to the oxo group completes the distorted octahedral
coordination sphere at a rather elongated distance of
2.324(5) Å, due to the trans influence of the oxo
group. This is accompanied by a significant displace-
ment of the vanadium atom from the plane defined by
the four basal donor atoms towards the apical oxo oxy-
gen atom by 0.287(2) Å. The coordinate bond lengths
agree well with reported vanadium complexes contain-
ing this ligand type [20, 21]. In the crystal packing
structure of the complex, hydrazone molecules are
In the electronic spectra of the complexes, the low-
est energy transition bands are observed at 407 nm for
I and 410 nm for II, which are attributed to
LMCT transition as charge transfer from p-orbital
on the lone-pair of ligands’ oxygen atoms to the empty
d-orbital of the vanadium atoms. The other strong
bands in the range of 320–340 nm in the spectra of
both complexes are similar to the absorption
bands in the spectra of the corresponding hydrazone
compounds, so they are attributed to the intra-ligand
π → π* absorption peak of the ligands. The other
mainly LMCT and to some extent π → π*
bands appear at 260 nm for I and 255 nm for II, and
this is due to the oxygen donor atoms bound to vana-
dium(V) [19].
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WU et al.
(a)
C(13)
C(14)
C(12)
N(2)
C(6)
C(7)
Cl(2)
C(5)
N(1)
C(11)
C(9)
C(1)
O(3)
C(8)
O(2)
O(5)
C(17)
C(10)
C(2)
C(4)
V(1)
O(4)
C(3)
O(1)
Cl(3)
Cl(1)
C(15)
C(16)
(b)
C(13)
C(10)
C(14)
C(12)
C(11)
C(6)
N(2)
C(8)
C(7)
O(6)
C(5)
Cl(2)
C(9)
C(1)
C(2)
N(1)
O(2)
O(3)
C(4)
C(3)
Cl(3)
V(1)
O(1)
C(22)
C(20)
C(21)
C(19)
C(18)
O(4)
Cl(1)
O(7)
N(3)
C(15)
C(16)
C(23)
C(17)
O(5)
Fig. 1. A perspective view of complexes I (a) and II (b) with the atom labeling scheme. Thermal ellipsoids are drawn at the 30%
probability level.
linked by methanol molecules through intermolecular
hydrogen bonds of O–H···N (O(5)–H(5) 0.85(1),
Molecular structure of complex II is shown in
Fig. 1b. The asymmetric unit of the complex contains
H(5)···N(2)i 2.03(2), O(5)···N(2)i 2.873(7) Å, O(5)– a vanadium complex molecule and an ethanol mole-
H(5)···N(2)i 170(11)°; symmetry code for i 1 – x, 1 – y,
1 – z) to form dimers (Fig. 2a).
cule of crytallization. There is an intramolecular
hydrogen bond in the complex molecule (N(3)–H(3)
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SYNTHESIS, CHARACTERIZATION, AND CRYSTAL STRUCTURES
383
carbonyl atom of the benzohydroxamate ligand trans
to the oxo group completes the distorted octahedral
coordination sphere at a rather elongated distance of
2.244(6) Å, due to the trans influence of the oxo
group. This is accompanied by a significant displace-
ment of the vanadium atom from the plane defined by
the four basal donor atoms towards the apical oxo oxy-
gen atom by 0.287(2) Å. The coordinate bond lengths
are comparable to those of complex I, and also agree
well with reported vanadium complexes containing
the enolate form of this ligand type [20–22]. In the
crystal packing structure of the complex, the ethanol
molecules are linked to the hydrazone ligands through
intermolecular hydrogen bonds of O–H···O (O(5)–
H(5) 0.82, H(5)···O(7)i 1.85, O(5)···O(7)i 2.655(8) Å,
O(5)–H(5)···O(7)i 169(8)°; symmetry code for i 1 – x,
1 – y, 1 – z) (Fig. 2b).
(a)
z
y
0
x
(b)
The hydrazone compound H2L and the two com-
plexes were screened for antibacterial activities against
two Gram (+) bacterial strains (Bacillus subtilis and
Staphylococcus aureus) and two Gram (–) bacterial
strains (Escherichia coli and Pseudomonas fluores-
cence) by MTT method. The MIC (minimum inhibi-
tory concentration, μg mL–1) values of the com-
pounds against four bacteria are listed in Table 3. Pen-
icillin G was used as the standard drug. The hydrazone
compound shows strong activity against S. aureus,
medium activity against B. subtilis and E. coli, and
weak activity against P. f luorescence. The two com-
plexes have strong activity against B. subtilis and
S. aureus, medium activity against E. coli, while no
activity against P. f luorescence. In general, the activi-
ties of both complexes are similar except for E. coli.
The free hydrazone ligand and complexes show no
activity against two fungal strains Candida albicans
and Aspergillus niger.
x
z
0
y
Fig. 2. Hydrogen bonds linked crystal packing structure of
complex I (a) and II (b).
0.90(1), H(3)···O(5) 2.00(5), N(3)···O(5) 2.630(9) Å,
N(3)–H(3)···O(5) 125(5)°). The coordination geome-
try around the vanadium atom can be described as a
distorted octahedral with the tridentate hydrazone
ligand coordinated in a meridional fashion, forming
five- and six-membered chelate rings with bite angles
FUNDING
This work was financially supported by K.C. Wong
of 74.8(2)° and 84.0(2)°, respectively, typical for this Magna Fund in Ningbo University, Ningbo natural
type of ligand systems [20]. The chelating hydrazone science fund (project no. 201701HJ-B01019) and
ligand lies in a plane with one hydroxylato ligand Ningbo Education Research Project (project
which lies trans to the hydrazone imino N atom. One no. 2017YZD001).
Table 3. Antimicrobial activities of the compounds I and II
Minimum inhibitory concentrations, μg mL–1
Tested material
B. subtilis
S. aureus
E. coli
P. fluorescence
H2L
I
II
9.4
4.7
4.7
2.3
4.7
4.7
4.7
4.7
75
>150
>150
>150
37.5
37.5
75
Penicillin G
>150
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12. Liu, J.-L., Sun, M.-H., and Ma, J.-J., Synth. React.
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No. 5
2019