Silver(I) catalyzed oxidation of thiocarboxylic acids into the corresponding disulfides and synthesis of some new Ag(I) complexes of thiophene-2-thiocarboxylate

Article abstract of DOI:10.1016/j.poly.2010.09.033

Aromatic thiocarboxylic acids in presence of a base on treatment with silver nitrate under ambient conditions were oxidized to the corresponding disulfides. The reactions were found to be catalyzed by Ag⁺ ions. The catalytic oxidation is paralleled by the Ag(SCOAr) complex formation reaction which could be considerably subsided by adjustment of the reaction conditions. Attempts to use [Ag(PPh₃)₂]⁺ or [Ag(PPh ₃)]⁺ ion as the catalyst were unsuccessful as these resulted in the formation of the corresponding thiocarboxylate complexes. The products, ArCOSSCOAr (1, 2), [Ag(SCOAr)(PPh₃)₂] (3, 4) and [Ag(SCOAr)(PPh₃)]₄ (5) (Ar = C₆H₅, C₄H₃S) were characterized by single crystal X-ray analysis. Compounds 3 and 4 are monomeric while 5 is a cyclic tetramer in the crystalline phase.

Full text of DOI:10.1016/j.poly.2010.09.033

Polyhedron 30 (2011) 93–97
Contents lists available at ScienceDirect
Polyhedron
journal homepage: www.elsevier.com/locate/poly
Silver(I) catalyzed oxidation of thiocarboxylic acids into the corresponding
disulfides and synthesis of some new Ag(I) complexes of thiophene-2-
thiocarboxylate
Suryabhan Singh , Jyotsna Chaturvedi , Subrato Bhattacharya , Heinrich Nöth b
a
a
a,
⇑
a
Department of Chemistry, Banaras Hindu University, Varanasi 221005, India
Department of Chemistry, University of Munich, Butenandtstrasse 5-13, D-81377 Munich, Germany
b
a r t i c l e i n f o
a b s t r a c t
Article history:
Aromatic thiocarboxylic acids in presence of a base on treatment with silver nitrate under ambient con-
ditions were oxidized to the corresponding disulfides. The reactions were found to be catalyzed by Ag
ions. The catalytic oxidation is paralleled by the Ag(SCOAr) complex formation reaction which could
Received 22 June 2010
Accepted 24 September 2010
Available online 7 October 2010
+
+
be considerably subsided by adjustment of the reaction conditions. Attempts to use [Ag(PPh
3
)
2
]
or
+
[
Ag(PPh
thiocarboxylate complexes. The products, ArCOSSCOAr (1, 2), [Ag(SCOAr)(PPh
COAr)(PPh )] (5) (Ar = C , C S) were characterized by single crystal X-ray analysis. Compounds 3
and 4 are monomeric while 5 is a cyclic tetramer in the crystalline phase.
Ó 2010 Elsevier Ltd. All rights reserved.
3
)] ion as the catalyst were unsuccessful as these resulted in the formation of the corresponding
Keywords:
Thioacid
Disulfide
Silver catalyzed
Catalytic oxidation
Thiocarboxylate
3 2
)
] (3, 4) and [Ag(S-
3
4
6
H
5
4 3
H
1
. Introduction
2. Experimental
Oxidation of thiols into disulfides is an important reaction in
All the solvents (LR grade) were distilled before they were used.
biological systems. Several cellular redox potentials are controlled
by oxidation of thiols to prevent oxidative damage of proteins.
During past two decades a number of reactions have been reported
by which thiols can be oxidized to disulfides. Various reagents and
oxidants have been employed for conversion of thiols to disulfides
3
AgNO (Qualigens), thiobenzoic acid and thiophene-2-carbonyl
chloride (Sigma–Aldrich) were used as received. Thiophene-2-
thiocarboxylic acid was synthesized as reported earlier [11].
Triethylamine was stored over NaOH and distilled prior to its
use. During the manipulations care was taken to protect the
reaction vessels from direct day light. Elemental analyses were
carried out by using Exeter Model CE-440 CHN analyzer. IR spectra
were recorded as KBr pellets on a VARIAN 3100 FT-IR spectro-
[
1–3]. Besides enzymatic [4] and electrochemical [5,6] methods a
number of such reactions are reported which are catalysed by var-
ious transition metals ions [7,8]. Interestingly, similar catalytic
reactions converting thiocarboxylic acids into corresponding disul-
fides are not available in literature. Though cuprous thiobenzoate
has been reported [9] to decompose on prolonged heating giving
dibenzoyldisulfide along with some other products but the oxida-
tion of thiobenzoate anion is non-catalytic in this process.
ꢀ1
1
13
photometer in the region 400–4000 cm . H and C NMR spectra
were recorded on a JEOL AL300 FT NMR Model spectrometer in
CDCl
3
solvent; the chemical shifts were measured with reference
1
to tetramethylsilane ( H).
We have reported earlier [10] that thioacetic and thiobenzoic
acids are converted to diacetyl and dibenzoyl sulfides respectively
2
.1. Catalytic oxidation of thiobenzoic acid
3
+
in presence of In . However, these reactions are stoichiometric
and give highly stable metal sulfide complexes at the end which
can not be dissociated easily to give back the free metal ions to cat-
alyze the reactions in a second cycle. We here report the oxidation
of thiobenzoic and thiophene-2-carboxylic acids into the corre-
To
a solution of thiobenzoic acid (0.552 g, 4 mmol) in
1
0 mL methanol was added a methanolic solution (10 mL) of
triethylamine (0.404 g, 4 mmol). After stirring for 30 min, 10 mL
of the reaction mixture was added drop wise to a magnetically stir-
red solution of silver nitrate (0.085 g, 0.5 mmol) in ꢁ15 ml metha-
nol. After stirring the reaction mixture for 1 h at 30 °C the
remaining portion (10 mL) of the triethylammonium thiobenzoate
solution was added into it slowly. The reaction mixture was stirred
overnight and then filtered off the black precipitate formed.
+
sponding disulfides using a Ag salt.
⇑
Corresponding author.
E-mail address: bhatt99@yahoo.com (S. Bhattacharya).
0
277-5387/$ - see front matter Ó 2010 Elsevier Ltd. All rights reserved.
doi:10.1016/j.poly.2010.09.033

9
4
S. Singh et al. / Polyhedron 30 (2011) 93–97
Table 1
Crystallographic data of compounds 1–5.
Compound
1
2
3
4
5
Empirical formula
Crystal system
Space group
a (Å)
b (Å)
c (Å)
C
14
H
10
O
2
S
2
C
10
H
6
O
2
S
4
C
43
H
35
O
1
S
1
P
2
Ag
C
43
H
35AgCl6
O
3
P
S
2 2
C
92 4 4 4 8
H72Ag O P S
monoclinic
P2 /c
12.2167(8)
12.0017(8)
8.9366(6)
monoclinic
P2 /c
7.9678(3)
6.5494(3)
23.1681(11)
triclinic
P1ꢀ
monoclinic
P2 /n
10.398(5)
25.701(5)
18.721(5)
triclinic
P1ꢀ
13.256(6)
14.1978(17)
14.201(2)
60.208(14)
71.03(2)
68.88(2)
2128.3(10)
1
1.602
1290
150
16228
9450
0.0393
1.013
1
1
1
10.229(2)
13.210(3)
14.232(3)
89.02(3)
76.63(3)
76.82(3)
1820.3(6)
2
1.404
788
293
7086
a
(°)
b (°)
(°)
107.462(1)
9098.014(4)
104.937(5)
c
3
V (Å )
1249.91(14)
4
1.458
568
1197.20(9)
4
1.589
584.0
293
4743
2612
0.0591
1.047
4834(3)
4
1.438
2112
293
30172
10987
0.1162
1.030
Z
D
calc (g/cm3)
F(0 0 0)
Temperature (K)
Collected reflections
Unique reflections
R
100
8032
3076
0.0551
1.16
6312
0.0268
1.071
Goodness-of-fit (GOF)
Solvent from the filtrate was evaporated under reduced pressure.
Extracted the residue 6–7 times with 5 mL portions of carbon
disulfide which on slow evaporation yielded a crop of pink colored
crystals of dibenzoyl disulfide (1) Yield 72%. M.p. 134 °C (Lit.
2.3. Attempted oxidation of thiobenzoic acid using AgNO
[synthesis of Ag(SCOPh)(PPh (3)]
3 3 2
(PPh )
3 2
)
To a solution of thiobenzoic acid (0.552 g, 4.0 mmol) in
10 mL methanol was added a methanolic solution (10 mL) of
triethylamine (0.404 g, 4.0 mmol). After stirring for 30 min,
1
10 2 2
34.5 °C). Anal. Calc. for C14H O S : C, 61.29; H, 3.67. Found: C,
6
1.78; H, 3.36%.
1
0 mL of the resulting solution was added dropwise to a magneti-
cally stirred suspension of bis(triphenylphosphine)silver nitrate
2
.2. Catalytic oxidation of thiophene-2-thiocarboxylic acid
(
0.347 g, 0.5 mmol) in ꢁ15 mL methanol. After stirring the reaction
mixture for 1 h the remaining portion of the triethylammonium
thiobenzoate solution was slowly added into it. The reaction mix-
ture was stirred overnight and yellow precipitate formed was fil-
tered out. Recrystallized from chloroform. Yield 98%. M.p. 220 °C
The same procedure was applied as in case of thiobenzoaic acid.
Reddish yellow crystals of 2,2’-thenoyl disulfide (2) were obtained.
Yield 69%. M.p. 120 °C. Anal. Calc. for C10H O S : C, 41.93; H, 2.11.
6 2 4
Found: C, 41.78; H, 2.09%.
(
dec). Anal. Calc. for C43
35 1 1 2
H O S P Ag: C, 67.11; H, 4.58. Found: C,
6
7.10; H, 4.58%.
2
.4. Synthesis of Ag(SCOTh)(PPh
3
2 3 2
) ꢂ2CHCl 2H O (4)
To a suspension of (PPh
3
)
2
AgNO (0.694 g, 1.00 mmol) in aceto-
3
nitrile (10.0 ml), added a solution of sodium thiophene-2-thiocarb-
oxylate (0.166 g, 1.00 mmol) in 5.0 ml of acetonitrile with stirring.
After five minutes of addition an yellow precipitate was formed.
The reaction mixture was stirred for an hour, collected the precip-
itate and dried under vacuum. The yellow powder was re-dissolved
in chloroform, layered with petroleum ether (60–80 °C) then kept
for crystallization. After two days yellow colored rod shape crystals
suitable for single crystal X-ray diffraction were obtained. Yield:
9
6 3 2 2
2%. M.p. 208–210 °C. Anal. Calc. for C43H39Cl O P S Ag: C, 49.17;
ꢀ1
Scheme 1. Catalytic cycle for the oxidation of thiobenzoic acid.
H 3.74. Found: C, 48.92; H, 3.71%. IR (KBr, cm ): 1566
m(CO),
Oδ−
O
Cδ+
Ag
S
S
-AgS
S
O
O
Scheme 2. Decomposition of silver thiobenzoate.

S. Singh et al. / Polyhedron 30 (2011) 93–97
95
3
(
days colorless block shaped crystals were obtained. Yield: 0.420
82%). M.p. 160–162 °C. Anal. Calc. for C92 Ag : C, 53.81;
H, 3.53. Found: C, 53.54; H, 3.47%. IR (KBr, cm ): 1579 (CO),
, d ppm): 6.88–
.70 (Ph and Th ring). C NMR: 127.04–148.10 (Ph and Th ring),
92.38 (COS).
H
72
O
4
P
4
S
8
4
ꢀ
1
m
1
1
7
1
186 m(Cthiophene–C), 1039 m(C–S). H NMR (CDCl
3
1
3
2.6. X-ray crystallography
Single-crystal X-ray data for 1 and 3 were collected on Bruker
SMART APEX CCD diffractometers while the same for 2, 4 and 5
were collected on a Xcalibur Eos Oxford CCD diffractometer using
graphite monochromated Mo K
a radiation (k = 0.71073 Å). The
data integration and reduction for 1, 3 and 2, 4, 5 were processed
with SAINT and CRYSALISPRO softwares, respectively [12,13]. The struc-
2
tures were solved by the direct method and then refined on F by
the full-matrix least-squares technique with the SHELXL-97 software
[
14] using the WINGX (ver 1.70.01) program package [15]. All non-
hydrogen atoms were refined anisotropically. Hydrogen atoms
were treated as riding atoms using SHELX default parameters. Other
crystallographic data are summarized in Table 1.
3
. Results and discussion
3.1. Oxidation of thiobenzoic acid
When excess thiobenzoic acid was treated with Ag(I) in pres-
ence of a base (triethylamine) dibenzoyldisulfide was obtained
along with some other products described in the succeeding para-
graph. The mechanism of this reaction (Scheme 1) is expected be
analogous to that observed in the case of transition metal catalysed
oxidation of thiols [16]. Two moles of thiobenzoate ions are oxi-
dized to give one mole of dibenzoyl disulfide. One mole of water
and half mole of dioxygen are consumed in each cycle. Oxygen
involved in the reaction was not added but was obtained from
air under ambient conditions. Bubbling oxygen gas in the reaction
vessel did not improve the yield to any noticeable extent. However,
the reaction when carried out under dry nitrogen atmosphere
using anhydrous solvents did not yield the disulfide.
Fig. 1. Molecular structures of 1 and 2.
3
183 m(Cthiophene–C), 1031 m , d ppm): 6.87–
(C–S). 1H NMR (CDCl
1
7
1
13
.65 (Ph and Th ring). C NMR 127.01–149.61 (Ph and Th ring),
95.81 (COS).
2
4 4 3 4
.5. Synthesis of [Ag (SCOTh) (PPh ) ] (5)
To a solution of PPh
added a solution of AgNO
3
(0.262 g, 1.00 mmol) in 10.0 mL methanol,
(0.170 g, 1.00 mmol) in 5.0 mL of meth-
3
anol, followed by a solution of sodium thiophene-2-thiocarboxy-
late (0.166 g, 1.00 mmol) in 5.0 ml of methanol with stirring. The
reaction mixture was stirred for 2–3 h then dried under reduced
pressure. The white residue was dissolved in toluene and filtered
to remove NaCl. The filtrate was kept for crystallization. After
It is worth mentioning here that the reaction of Ag+ ion with
stoichiometric amount of sodium thiobenzoate in aqueous med-
ium is reported to give Ag(SCOPh) complex in almost quantitative
yields [17]. In our case also the catalytic oxidation of the thioacid
is paralleled by a complex formation reaction where in a silver
Table 2
Selected bond lengths and bond angles.
Complex
(
A) Selected bond lengths
1
2
4
5
S1–S2
O1–C8
S1–S3
O1–C1
Ag1–S1
Ag1–P2
Ag1–S1
Ag2–S3
2.0246(11)
1.203(3)
2.0147(14)
1.200(4)
2.515(3)
2.462(2)
S1–C8
O2–C1
S1–C1
O2–C6
Ag1–O1
S1–C1
Ag1–S3
Ag1–P1
1.833(3)
1.212(3)
1.810(4)
1.204(4)
2.919
1.719(10)
2.5220(13)
2.4234(13)
S2–C1
C1–C2
S3–C6
C1–C2
Ag1–P1
O1–C1
Ag2–S1
Ag2–P2
1.819(3)
1.480(4)
1.799(3)
1.455(5)
2.477(2)
1.216(11)
2.5697(14)
2.4016(9)
2.5236(11)
2.5096(11)
(
B) Selected bond angles
1
S2–S1–C8
S2–C1–C2
S3–S1–C1
S1–C1–C2
S1–Ag1–P1
S1–Ag1–S3
S3–Ag2–S1
Ag1–S1–Ag2
100.17(9)
114.39(18)
100.95(12)
112.9(2)
117.47(9)
105.54(4)
93.47(4)
S1–S2–C1
O2–C1–C2
S1–S3–C6
O1–C1–C2
S1–Ag1–P2
S1–Ag1–P1
S3–Ag2–P2
Ag2–S3–Ag1
101.38(9)
124.2(2)
102.24(12)
125.2(3)
118.73(9)
126.21(4)
139.30(4)
86.48(4)
S2–C1–O2
C1–C2–C3
S1–C1–O1
121.4(2)
117.7(2)
121.9(3)
2
4
5
P1–Ag1–P2
S3–Ag1–P1
S1–Ag2–P2
123.61(8)
125.41(4)
126.72(4)
89.35(4)

9
6
S. Singh et al. / Polyhedron 30 (2011) 93–97
Fig. 2. Intermolecular interactions in 1.
complex, Ag(SCOPh) is formed. Interestingly, the complex Ag(SOCPh)
is kinetically unstable and decomposes slowly in solution giving sil-
ver sulfide and dibenzoyl sulfide (Scheme 2). Similar decomposition
has also been reported in some other cases [10].
Since the decomposition is due to the nucleophilic attack of the
thiobenzoate ion on the carbonyl carbon of the Ag(SOCPh) com-
plex, a higher concentration of the former in the reaction medium
is expected to enhance the decomposition reaction. This was in-
selected bond lengths and angles are listed in Table 2. The Ph-COS
units are as expected, almost planar, however, the two units are al-
most perpendicular to each other the CSSC torsional angles being
80.6° and 86.3° in 1 and 2, respectively. As a result the two car-
bonyl oxygens are quite away from each other. One may expect
existence of intramolecular hydrogen bonds due to the close plac-
ing of atoms, CHꢂ ꢂ ꢂO (2.570 Å in 1) and CHꢂ ꢂ ꢂS (2.632 Å in 1 and
2.786 Å in 2), however, the C–H–Y (Y = O/S) angles are too small
(varying between 97.95° and 108.98°) to allow such bonding
[18]. Intermolecular CHꢂ ꢂ ꢂO bonds are, however, present as shown
in both the cases. The molecules pack in such a way that channel
like structures are formed in the lattice. In the case of 1 a distance
of 3.8 Å between the centroids of two adjacent parallel phenyl
deed observed when a reaction of AgNO
3
and PhOCSH was carried
out in 1:10 M ratio. Ag S and (PhCO) S were obtained almost quan-
2
2
titatively and the excess thiobenzoate salt remained unreacted.
Such a situation could be avoided by introducing the thiobenzoate
salt very slowly and in batches.
In this proposed mechanism, when thiobenzoate anion is con-
+
verted into the corresponding radical in presence of Ag ion the lat-
ter is reduced to the zero valent state. Metals in zero valent state
play important role in many homogeneous catalytic processes. To
stabilize such species (atomic) without allowing them to agglom-
erate into a metal lattice (solid)
r-donor/p-acceptor ligands such
as phosphines, carbonyl and dienes) are widely used. To increase
the efficiency of the catalytic oxidation of the thiocarboxylate
and if possible, to isolate a species containing silver in zero oxida-
tion state we have carried out this reaction in presence of bis(tri-
phenylphosphine)silver(I) nitrate. Surprisingly, no catalytic
oxidation took place. Instead, the complex, [Ag(SCOR)(PPh
R = Ph or Th) were isolated in good yields. Attempts to carryout
the catalytic oxidation under lower concentration of substrate also
led to the formation of a stable complex [Ag(SCOR)(PPh )]
3 2
) ]
(
3
4
.
3.2. Crystal and molecular structures
The products of the catalytic reactions, dibenzoyl disulfide and
0
2
,2 -dithenoyl disulfide were characterized crystallographically.
The unit cells in both the cases are monoclinic with P2
1
/c space
group. Molecular structures of 1 and 2 are given in Fig. 1 and
Fig. 3. Molecular structure of 4 (hydrogen are omitted for clarity).

S. Singh et al. / Polyhedron 30 (2011) 93–97
97
O
O
S1
O
S1
O
M
M
S
S1
S
S1
S
S
M
M
Scheme 3. Possible bonding modes of thiophene-2-thiocarboxylate ligand.
is analogous to those of [Ag(SCOPh)(PPh
3
)]
4
ꢂ2CH
2
Cl
2
and [Ag(S-
COPh)(PPh )] CH reported by Vittal et al. [15], there are sig-
3
4
ꢂC
6
H
5
3
nificant differences as well.
Ag–S–Ag–S dihedral angles are 5.37° and 7.86° while S–Ag–S–Ag
are 165.81° and 131.86° respectively in 5 and [Ag(SCOPh)(PPh
CH Cl . The Ag ring in 5 is more puckered as compared to that
of [Ag(SCOPh)(PPh
chair in the former is much shorter (3.657 Å) than the latter
4.458 Å). Similarly, the Ag–S distances across the chair (3.182 Å)
are significantly shorter than those in the reported structure
3
)] ꢂ
4
2
2
2
4 4
S
0
3
)]
4
ꢂ2CH
2 2
Cl . The Ag2–Ag2 distance across the
(
(
4.519 Å). The most significant difference in the structure is the
0
arrangement of thiocarboxyl groups. The O atoms (O2 and O2 ) in
5
face away from the eight membered ring as opposed to the
observed orientation in the corresponding thiobenzoate complexes
in which the O atoms are placed above and below the ring. It may be
mentioned here that both solvent and substitution on thiocarboxy-
late groups are known to influence the solid state structures of the
eight membered rings.
Fig. 4. Molecular structure of 5 (hydrogen and phenyl ring carbon atoms are
omitted for clarity).
Acknowledgement
Financial support to S.B. and fellowships to S.S. and J.C. from the
Council of Scientific and Industrial Research, New Delhi, are grate-
fully acknowledged.
rings (as shown by the thin solid line in Fig. 2) indicates the exis-
tence of strong intermolecular p–p interactions.
Synthesis and structure of 3 have already been reported by Vit-
ꢀ
tal et al. [19]. The molecule crystallizes in a triclinic system with P1
Appendix A. Supplementary data
space group (Table 2). Though we could refine the structure much
better than that reported earlier there is no point in discussing the
structural details further.
Complex 4 crystallized in monoclinic system with space group
1
P2 /n. Molecular structure is depicted in Fig. 3 and selected bond
CCDC 705265, 780187, 780188, 780189 and 780190 contains
the supplementary crystallographic data for compounds 1, 2, 3, 5
and 4. These data can be obtained free of charge via http://
www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK; fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk.
length and bond angles are given in Table 1.
Two molecules of each water and chloroform were crystallized
with each molecule of 4 in which one chloroform molecule is dis-
ordered. The molecular structure is similar to that of 3; the silver
atom is bonded to two phosphorus atoms of triphenylphosphine
and one sulfur atom of thiophene-2-thiocarboxylate group. Though
the ligand possesses three possible donor sites and may exhibit
quite a few different bonding modes (Scheme 3) only S1, the sulfur
of the thiocarboxylate group coordinates to the metal.
The Ag–O1 distance (2.910 Å) is quite longer than the sum of
the covalent radii of the two atoms (2.13 Å) and any significant
interaction between the two atoms is unlikely. The geometry
around Ag atom is trigonal planar and it lies in the plane consti-
References
[
[
1] C.C. Silveira, S.R. Mendes, Tetrahedron Lett. 48 (2007) 7469.
2] R. Sanz, R. Aguado, M.R. Pedrosa, F.J. Arnaiz, Synthesis 7 (2002) 856.
[3] C.A.S. Regino, D.E. Richardson, Inorg. Chim. Acta 360 (2007) 3971.
[
[
[
4] M. Sridhar, S. Kumaravedivel, V.T. Bhaelrao, Synth. Commun. 28 (1998) 1499.
5] L.S. Sergio, V.L. Pardini, H. Viertler, Synth. Commun. 20 (1990) 393.
6] A. Salimi, R. Hallaj, Talanta 66 (2005) 967.
[7] R. Hekmatshoar, S. Sajadi, M.M. Heravi, F.F. Bamoharram, Molecules 12 (2007)
223.
2
[
[
8] A. Supale, G. Gokavi, React. Kinet. Catal. Lett. 93 (2008) 141.
9] A. Ferretti, Can. J. Chem. 50 (1972) 4056.
tuted by S
, P
1 1
and P
2
atoms.
[10] P. Singh, S. Bhattacharya, V.D. Gupta, H. Nöth, Chem. Ber. 129 (1996) 1093.
[11] J. Hübner, K. Taraz, H. Budzikiewicz, Phosph. Sulfur Silicon Relat. Elem. 47
Complex 5 have an eight member ring constituted by the four
silver and four sulfur atoms arranged alternately in a chair confor-
mation (Fig. 4). Selected bond lengths and bond angles are given in
Table 1. Four silver atoms and four sulfur atoms of thiocarboxylate
constitute an eight membered ring with a crystallographic inver-
sion centre at the middle. Each silver atom is bonded to one phos-
phorus atom of triphenyl phosphine and two sulfur atoms of two
thiocarboxylate ligands. Silver atom is tipped above the plane con-
stituted by P, S and S plane atoms by 0.757 Å. Though the structure
(
1990) 367.
[
12] SAINT+, 6.02 ed.; Bruker AXS, Madison, WI, 1999.
[
13] CRYSALISPRO, Oxford Diffraction Ltd., Yarnton, England, 2009.
[14] G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University
of Göttingen, Göttingen, 1997.
[
[
15] L.J. Farrugia, J. Appl. Cryst. 32 (1999) 837.
16] C.F. Cullis, D.L. Trimm, Discuss. Faraday Soc. 46 (1968) 144.
[17] V.V. Savant, J. Gopalakrishnan, C.C. Patel, Inorg. Chem. 9 (1970) 748.
[
[
18] G.R. Desiraju, Acc. Chem. Res. 29 (1996) 441.
19] T.C. Deivaraj, J.J. Vittal, J. Chem Soc., Dalton Trans. (2001) 329.