2
A. Dehno Khalaji et al. / C. R. Chimie xxx (2016) 1e6
Jana2006 program package [16] by the full-matrix least-
2
NH2
squares technique on F . The molecular structure plots
were prepared by using Diamond 4 [17]. Hydrogen atoms
were mostly discernible in difference Fourier maps and
could be refined to reasonable geometry. According to the
common practice, hydrogen atoms attached to carbons
were kept in ideal positions during the refinement. The
isotropic atomic displacement parameters of hydrogen
atoms were set to 1.2 Ueq of their hydrogen atoms. Crys-
tallographic data and details of the data collection and
structure solution and refinements are listed in Table 1.
HN
a
b
N
S
d
NO3
c
Ag
f
e
g
j
Ph P
PPh3
3
h
i
2.4. Antibacterial activity
3 2 3
Scheme 1. The chemical structure of [Ag(catsc)(PPh ) ]NO .
The antibacterial activity of the catsc ligand and its sil-
ver(I) complex [Ag(catsc)(PPh ) ]NO were investigated
3 2 3
against two standard strains of gram-positive (Staphylo-
coccus aureus ATCC-25923 and Enterococcus faecalis ATCC-
9212) and gram-negative (Escherichia coli ATCC 25922 and
Pseudomonas aeruginosa ATCC-27853) bacteria by the pure
plate method. The tests were performed by using the
methodology described in the guidelines of the ‘Comit eꢀ de
complex were prepared at 20 mg/mL in DMSO under sterile
conditions. After dilution, 10 petri plates with 10, 20, 30, 40,
(
PerkineElmer) spectrometer. Elemental analyses were
1
13
carried out using a Heraeus CHN-O-Rapid analyzer. H,
and P NMR spectra were measured on a Bruker DRX-400
AVANCE spectrometer at 400 MHz. All chemical shifts were
C
31
2
reported in
d units downfield from TMS. The TG was per-
formed on a PerkinElmer TGA/DTA lab system 1 (Technol-
ogy by SII) in an argon atmosphere, using the heating rate
2
spectra were recorded by a PerkinElmer Spectrometer
Lambda 25.
ꢀ
ꢀ
0 C/min and the temperature span 30e750 C. UVevis
(
2
.2. Preparation of [Ag(catsc)(PPh
3
)
2
]NO
3
50, 60, 70, 80, 90and100 mg/mLconcentrationofcatsc andits
4
complex were prepared. About 2 ꢂ10 bacteria suspended in
The ligand catsc (0.021, 1 mmol) was added to an ace-
tonitrilic suspension of AgNO (0.017 g, 0.1 mmol) and
PPh (0.052 g, 0.2 mmol) (molar ratio, 1:2) and stirred for
sterile distilled water were inoculated on the different petri
ꢀ
3
plates. After incubation for 24 h at 37 C, the minimum
3
inhibitory concentration (MICs
. Results and discussion
.1. Synthesis and characterization
Thiosemicarbazone ligand catsc was prepared in high
mg/mL) was determined.
0
.5 h until a yellow clear solution was obtained. The solution
ꢀ
was left at ꢁ4 C for several days and then slowly evaporates
at room temperature. The white polygon crystals were
filtered and washed twice with acetonitrile, and dried at
room temperature. Anal. Calcd for C46
6
6
3
3
H
41AgN
4 3 2
O P S: C,
1.41; H, 4.59; N, 6.23; S, 3.56%. Found: C, 61.47; H, 4.65; N,
ꢁ
1
.31; S, 3.52%. FTIR data (KBr, cm ):
(CeH aromatic) 3017,
(eC]Ne imine) 1562, { (CeN) þ
(CeC) þ
93, 1056, 1148, 1182, (C]S) 814. H NMR (DMSO-d
y
(NeH) 3143 (eNH
(CeH imine)
(PeCPh)}
2
yield using a standard method [14]. The ligand catsc was
group), 3251e3409,
y
y
2
9
d
979,
y
n
n
n
Table 1
1
y
6
,
Crystallographic and refinement data for [Ag(catsc)(PPh ) ]NO .
3
2
3
b
ppm): 11.7 (s, 1H, eNHe), 8.6 (s, 1H, eC H ¼ Ne), 8.0e8.1
Empirical formula
Formula weight
Crystal system
Space group
a/Å
C
46
H
41AgN
4
O
3
P
2
S
h
c,d
(
d, 1H, C H); 7.8 (s, 2H, eNH
2
); 7.2e7.6 (32H, PPh
3
þ C H);
899.75
Orthorhombic
P2
12.2631(4)
23.3682(6)
28.6672(9)
8215.1(4)
2
f,j
g,i
13
7.0e7.1 (d, 2H, C H); 6.8 (dd, 2H, C H). C NMR (DMSO-d
6
,
a
b
d
ppm): 175.7 (C ]S), 147.5 (C
¼
N), 124.8e140.7
1 1 1
2 2
cej
31
(
C
þ PPh
3
). P NMR (DMSO-d
6
,
d
ppm): 7.6. UVevis (
max
l ,
b/Å
nm): 272, 372.
c/Å
V/Å
3
Z
m
2
.3. X-ray crystallography
single crystal of [Ag(catsc)(PPh
/mm 1
ꢁ
5.52
T/K
293
A
3
)
2
]NO
3
of size
Crystal size/mm
0.09 ꢂ 0.07 ꢂ 0.06
0
.09 mm ꢂ 0.07 mm ꢂ 0.06 mm was selected for an X-ray
T
T
min
0.881
max
1
diffraction study. Crystallographic measurements were
done at 293 K with a four circle CCD diffractometer Gemini
of Oxford diffraction, Ltd., with mirrors-collimated Cu K
radiation (
crystals was low (as indicated by the Rint factor in Table 2
for merging symmetry equivalent reflections) the crystal
structure could be nevertheless easily solved by charge
flipping with program SUPERFLIP [15] and refined with the
Measured reflections
47,513
Independent reflections
14,424
a
Reflections with I > 3
s
(I)
10,972
0.043
0.053
2
2
l
¼ 1.54184 Å). Although the quality of the single
R[F > 3
s
(F )]
2
wR(F )
S, Rint
Parameters
Drmax
1.52, 0.084
1045
0.32, ꢁ0.28
ꢁ3
,
mineÅ
3 2 3
Please cite this article in press as: A. Dehno Khalaji, et al., Silver(I) thiosemicarbazone complex [Ag(catsc)(PPh ) ]NO : Synthesis,
characterization, crystal structure, and antibacterial study, Comptes Rendus Chimie (2016), http://dx.doi.org/10.1016/
j.crci.2016.09.001
Dehno Khalaji, Aliakbar
