Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine carbodithioic acid: Synthesis, X-ray crystal structures, spectral properties and antimicrobial studies

Article abstract of DOI:10.1016/j.jorganchem.2005.12.004

Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine carbodithioic acid (4-MePCDTA) have been synthesized by the reaction with diorganotin dichloride in 1:1 molar ratio in anhydrous toluene. These newly synthesized complexes have been characterized b

Full text of DOI:10.1016/j.jorganchem.2005.12.004

Journal of Organometallic Chemistry 691 (2006) 1797–1802
www.elsevier.com/locate/jorganchem
Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine
carbodithioic acid: Synthesis, X-ray crystal structures,
spectral properties and antimicrobial studies
a
a,
b,
*
Saira Shahzadi , Saqib Ali *, Moazzam H. Bhatti
,
c
d
Mohammmad Fettouhi , Muhammad Athar
a
Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
Department of Chemistry, Allama Iqbal Open University, H/8, Islamabad, Pakistan
Department of Chemistry, King Fahad University of Petroleum and Minerals, 31261 Dhahran, Saudi-Arabia
b
c
d
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, PR China
Received 11 November 2005; received in revised form 1 December 2005; accepted 1 December 2005
Available online 6 January 2006
Abstract
Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine carbodithioic acid (4-MePCDTA) have been synthesized by the reaction
with diorganotin dichloride in 1:1 molar ratio in anhydrous toluene. These newly synthesized complexes have been characterized by ele-
mental, IR, multinuclear NMR (1H and 13C) and mass spectrometric studies. The crystal structures of complex 1 [Me2SnCl(4-MePCDT)]
and 3 [Ph2SnCl(4-MePCDT)] have been determined by X-ray single crystal analysis, which show trigonal bipyramid geometry. These
complexes were tested for their antimicrobial activity against six different plant and human pathogens. The screening results show that
the complexes exhibit higher antibacterial and antifungal activity than the free ligand.
ꢀ 2005 Elsevier B.V. All rights reserved.
Keywords: Chloro-organotin complexes; Dithiocarbamates; NMR; Mass; Antimicrobial study; X-ray structures
1. Introduction
Sulfur containing molecules are currently under study as
chemoprotectants in platinum-based chemotherapy. In
particular, thiocarbonyl and thiol donors have shown
promising properties for chemical use in modulating cis-
platin nephrotoxicity [5,6].
In recent years much attention have been paid to the
synthesis, characterization and biological activities of vari-
ous organotin(IV) derivatives with sulfur ligands like thi-
one or dithiocarbamate [7–9]. In addition to biological
activities the organotin derivatives are also subjected to
thermal and CVD studies [10,11]. In continuation to our
interest in synthetic and structural aspects of organotin(IV)
complexes of dithiocarbamate [12,13], we report here the
synthesis, spectral characterization, antimicrobial activity
and crystal structures of chloro-diorganotin(IV) derivatives
of 4-methyl-1-piperidine carbodithioic acid (Fig. 1).
Complexing agents with dithio functional group have
been widely used in industry as rodent repellents, vulcani-
zation additives in rubber manufacturing, additives in
lubricants and in agriculture as fungicides on almond trees,
stone fruits and vegetables [1]. Interest in complexes of
both main group and transition metals with sulfur donor
ligands arises in past because of their varied structures
and biological activity [2–4].
*
Corresponding authors. Tel.: +92512875027; fax: +92512873869
(S. Ali), Tel./fax: +92519250081 (M.H. Bhatti).
E-mail addresses: drsa54@yahoo.com (S. Ali), moazzamhussain_b@
yahoo.com (M.H. Bhatti).
0022-328X/$ - see front matter ꢀ 2005 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2005.12.004

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S. Shahzadi et al. / Journal of Organometallic Chemistry 691 (2006) 1797–1802
4H), 1.69 (m, 4H), 1.78 (m, 1H), 0.92 (d, 3H, CH3, (7.4)),
S
3
{1.77–1.30 (m, 12H), 0.89 (t, 6H), SnCH2CH2CH2CH3}.
13C NMR (DMSO-d6, ppm, nJ[119/117Sn, 13C]), 192.75
(CSS), 51.94 (C-2), 33.42 (C-3), 30.22 (C-4), 21.3 (CH3),
{22.0 [577/553], 28.84 [34], 27.57 [87], 13.62,
SnCH2CH2CH2CH3}. IR (KBr, cmÀ1), 320 m(Sn–Cl), 441
m(Sn–S), 532 m(Sn–C), 968 m(C@S), 1086 m(C–S).
2
N
C
SH
4
5
6
CH
3
Fig. 1. The structure and numbering scheme of 4-methyl-1-piperidine
carbodithioic acid.
2.2.3. Synthesis of Ph2SnCl(4-MePCDT) (3)
Crystalline complex 3 was made in the same way of com-
plex 1. It was recrystallized in chloroform–hexane. Yield:
90%, m.p. 192–193 ꢁC. Anal. Calc. for C19H22NS2ClSn:
C, 47.30; H, 4.56; N, 2.90; S, 13.27. Found: C, 47.35; H,
4.60; N, 2.88; S, 13.25%. 1H NMR (DMSO-d6, ppm),
2. Experimental
2.1. Materials and instrumentation
Analytical grade dimethyltin dichloride, dibutyltin
dichloride, diphenyltin dichloride and 4-methyl piperidine
were procured from Aldrich Chemical Company. CS2
was purchased from Riedel-de-Hae¨n. All solvents were
dried before used by the literature methods [14a]. 4-
Methyl-1-piperidine carbodithioic acid is prepared by the
literature method [14b,14c].
1
nJ(1H, H), 2.50 (m, 4H), 1.60 (m, 4H), 1.78 (m, 1H), 0.92
(d, 3H, CH3, (7.5)), {7.96–7.53 (m, 10H, SnC6H5)}. 13C
NMR (DMSO-d6, ppm,), 190.21 (CSS), 53.17 (C-2), 33.22
(C-3), 30.24 (C-4), 21.29 (CH3), {142.45, 135.15, 128.53,
129.21, SnC6H5}. IR (KBr, cmÀ1), 325 m(Sn–Cl), 450
m(Sn–S), 552 m(Sn–C), 960 m(C@S), 1065 m(C–S).
Carbon, hydrogen, nitrogen and sulfur analyses were
performed with a Perkin–Elmer 2400 Series II instrument.
IR spectra in the range 4000–250 cmÀ1 were obtained on a
Bio-Rad FTIR spectrophotometer with samples investi-
2.3. X-ray crystallography
All X-ray crystallographic data (Table 1) were collected
on a Bruker AXS Smart Apex diffractometer. Correction
for semi-empirical from equivalents was applied, and the
structure was solved by direct methods and refined by a
full-matrix least squares procedure based on F2 using the
SHELXL-97 Program System. All data were collected with
1
gated as KBr discs. The H and 13C NMR spectra were
recorded on a Bruker Advance 500 spectrometer operating
at 500 MHz. Mass spectra were recorded on MAT-112S
mass spectrometer.
˚
graphitemonochromated Mo Ka radiation (k = 0.71073 A)
at 295 K.
2.2. Syntheses
2.2.1. Synthesis of Me2SnCl(4-MePCDT) (1)
Table 1
The preparation of complex 1 was carried out at room
temperature. Me2SnCl2 (1 mmol), 4-MePCDTA (1 mmol)
and Et3N (1 mmol) were added to 100 cm3 of dry toluene
and refluxed for 4 h. The precipitated salt was removed
by filtration and the filtrate was evaporated under reduced
pressure. The product was recrystallized from chloroform–
hexane to give colorless crystals. Yield: 96%, m.p. 122–
123 ꢁC. Anal. Calc. for C9H18NS2ClSn: C, 30.16; H, 5.02;
N, 3.91; S, 17.87. Found: C, 30.20; H, 5.08; N, 3.89; S,
Crystal data and structure refinement parameters for complex (1) and (3)
Complex (1)
Complex (3)
Empirical formula
Formula weight
Crystal system
Space group
C9H18NS2ClSn
358
Triclinic
C19H22NS2ClSn
482
Monoclinic
P21/c
ꢀ
P1
Unit cell dimension
˚
a (A)
7.110 (8)
10.621 (12)
11.2185 (12)
113.377 (2)
97.562 (2)
107.290 (2)
711.86 (14)
2
13.581 (13)
9.637 (9)
17.171 (17)
90.00
112.828 (10)
90.00
2071.60 (3)
4
1.547
˚
b (A)
˚
17.89%. H NMR (DMSO-d6, ppm), J(1H, H), J[119Sn,
1H], 2.50 (m, 4H), 1.67 (m, 4H), 1.77 (m, 1H), 0.93 (d,
3H, CH3, (7.5)), {0.48 (s, 6H), SnCH3, [79.6]}. 13C NMR
(DMSO-d6, ppm), 193.9 (CSS), 51.74 (C-2), 33.3 (C-3),
30.3 (C-4), 22.7 (CH3), 14.6 (SnCH3). IR (KBr, cmÀ1),
328 m(Sn–Cl), 428 m(Sn–S), 555 m(Sn–C), 966 m(C@S),
1075 m(C–S).
1
n
1
n
c (A)
a (ꢁ)
b (ꢁ)
c (ꢁ)
3
˚
V (A )
Z
Dcalc (g cmÀ3
)
1.673
Crystal size (mm)
F(000)
0.31 · 0.24 · 0.08
356
0.33 · 0.19 · 0.17
968
Total reflections
Independent reflections
All indices (all data)
3296
2941
4977
4231
2.2.2. Synthesis of Bu2SnCl(4-MePCDT) (2)
R1 = 0.0319,
wR2 = 0.669
R1 = 0.0272,
wR2 = 0.0647
1.056
R1 = 0.0337,
wR2 = 0.0678
R1 = 0.0273,
wR2 = 0.0652
1.053
The procedure is the same as that of complex 1, and
complex 2 was recrystallized from chloroform–diethyl
ether to give crystalline product. Yield: 80%, m.p. 92–
93 ꢁC. Anal. Calc. for C15H30NS2ClSn: C, 40.72; H, 6.78;
N, 3.16; S, 14.47. Found: C, 40.76; H, 6.80; N, 3.20; S,
Final R indices [I > 2r(I)]
Goodness-of-fit
h Range for data collection (ꢁ)
Data/restrains/parameters
2.06–28.32
3296/0/130
1.63–28.26
4977/0/218
1
n
1
14.42%. H NMR (DMSO-d6, ppm), J(1H, H), 2.50 (m,

S. Shahzadi et al. / Journal of Organometallic Chemistry 691 (2006) 1797–1802
1799
3. Results and discussion
ing of free ligand in the region 2754 cmÀ1 and appearance
of Sn–S stretching in the range of 450–428 cmÀ1 and Sn–C
in the range of 555–525 cmÀ1 indicate the formation of
complexes [15]. The characteristic bands observed in the
spectra of 1–3 complexes in the region 328–320 cmÀ1 are
assigned to Sn–Cl stretching mode of vibration [15].
3.1. Synthesis
The ligand was obtained from the reaction of 4-meth-
ylpiperidine with carbon disulphide in dry methanol as
shown in the following equation:
3.3. NMR spectroscopy
S
i) Dry MeOH
ii) 4h Stirring
N
H
N
C
SH
The 1H NMR spectral data of 4-methyl-1-piperidine
carbodithioic acid shows single resonance at 1.27 ppm,
which is absent in the spectra of the complexes, indicating
the replacement of the dithiocarboxylic acid proton by a
diorganotin moiety. The nJ[119Sn, 1H] of dimethyltin deriv-
ative has a value of 79.6 Hz falling in the range for five
coordinated tin atoms [16a].
+
CS2
iii) Room temperature
CH3
CH3
The organotin derivatives 1–3 were obtained from the
reaction of R2SnCl2 with 4-MePCDTA in 1:1 molar ratio
in the presence of triethyl amine. The general chemical
reaction is given as:
In 13C NMR, the assignment of the 13C signal for –CSS
group is straightforward and is assigned in the range 193.9–
190.21 ppm for chloro-diorganotin(IV) complexes indicat-
ing the coordination of sulfur to the tin atom. R groups
attached to tin moiety give signals in the expected range.
The order of the magnitude of the coupling constant in
S
S
S
i) Toluene
R
N
C
SH
+
N
C
Sn
Cl
ii) Reflux for 4h
R2SnCl2 + Et3N
R
CH3
CH3
1
2, J[119Sn,13C], is same as reported for the analogous five
+
R = Me (1), Bu (2), Ph (3)
coordinated derivatives [16b,16c].
Et3NHCl
3.2. IR spectra
3.4. Mass spectrometry
The comparison is made between the spectra of com-
plexes and precursor. The N–H bond stretching in R2NH
(secondary amine) in the range of 3200 cmÀ1 disappeared
when it reacted with carbon disulfide, indicating the forma-
tion of the ligand. The disappearance of –SH bond stretch-
The conventional EI mass spectral data for the ligand
and compounds 1–3 are recorded and different fragmenta-
tion patterns have been proposed and are listed in Schemes
1–4 along with m/z and % intensity. In the mass spectrum
of 4-methyl-1-piperidine carbodithioic acid, molecular ion
+
+
CSS
CSSH
77 (5.5)
76 (8.6)
-C6H14N
-C6H12N
S
+
+
+
N
N
C
SH
-CS2
-CSSH
H3C
N H
CH3
CH3
H
175 (85.3)
98 (100)
99 (73.1)
-C2H4
-SH
-CH4
+
H3C
+
N
C
S
+
CH3
142 (93.0)
N
N
70 (7.4)
83 (29.9)
-CH3
+
N
55 (58.3)
Scheme 1. Fragmentation pattern for ligand (HL).

1800
S. Shahzadi et al. / Journal of Organometallic Chemistry 691 (2006) 1797–1802
S
peak is observed at m/z (%) 175 (85.3). The base peak is
observed at m/z (%) 98 (100) due to [C6H12N]+ fragment.
The other fragments at m/z (%) 142 (93.0), 76 (8.6), 83
(29.9), 99 (73.1) are observed for [C7H12NS]+, [CSS]+,
+
S
+
-SnPh2Cl
N
C
S
N
C
S SnPh2Cl
CH3
CH3
174 (n.o)
-CS2
482 (n.o)
-SnPhCl
-C7H12NS2
+
+
C6H5
77 (32.0)
+
S
Sn Ph2Cl
308 (27.5)
N
S
+
+
-Cl
N C S SnMe2
N C S SnMe2Cl
CH3
CH3
98 (100)
CH3
-Ph2
322(5.7)
-2CH2
358(n.o)
-C2H6
+
-CH2
Sn Cl
154 (47.1)
+
S
NH
84 (15.8)
+
S
+
N C S SnH2
-Cl
N C
S SnCl
CH3
+
294 (3.9)
-SSnH2
CH3
Sn
327(3.6)
-C2H4
-SSnCl
119 (5.2)
-C7H12NS 2
+
+
+
S
Sn Cl
154(7.8)
N C
NH
56 (39.6)
CH3
142 (100)
Scheme 4. Fragmentation pattern for compound (3).
-CS
[C5H9N]+ and [C6H13N]+, respectively. The fragmentation
patter is given in Scheme 1.
+
+
+
N
-CH3
-C2H4
N
N
CH3
In the mass spectral data for 1–3 most fragment ions
occur in group of peaks as a result of tin isotopes. For sim-
plicity the mass spectral fragmentation data reported here
is related to the principal isotope 120Sn [17]. The molecular
ion peak is not observed in all complexes. In general, the
complex 1 has base peak (100%) at m/z 142 due to frag-
ment [C7H12NS]+ while complexes 2 and 3 have base peak
due to the fragment [C6H12N]+ at m/z (%) 98 (100). The
other possible fragments with m/z (%) are reported in
Schemes 2–4.
55(42.9)
83(23.3)
98(47.9)
Scheme 2. Fragmentation pattern for compound (1).
S
S
+
+
-Cl
N
C S SnBu2
N
C
S SnBu2Cl
-C15 H30 NS2
CH3
+
CH3
442(n.o)
406 (8.3)
Sn Cl
155 (30.8)
-Bu2H
S
-C7H12 NS2
-C4 H9
3.5. Crystal structures
+
+
+
-C4H9
Sn Bu2Cl
269(39.2)
N
C S SnH2
Sn BuCl
212 (27.8)
Figs. 2 and 3 show the molecular structures and atomic
numbering scheme of complexes 1 and 3, respectively. The
intermolecular bond distances and angles are given in
CH3
294 (26.3)
-SnH
S
+
N
C S SH
CH3
175 (10.6)
-SH
+
S
N
C
CH3
142 (30.0)
-CS
+
+
+
N
-CH3
-C2 H4
N
N
CH3
98(100)
55(32.3)
83 (8.8)
Scheme 3. Fragmentation pattern for compound (2).
Fig. 2. ORTEP drawing of the X-ray structure of complex (1).

S. Shahzadi et al. / Journal of Organometallic Chemistry 691 (2006) 1797–1802
1801
ideal bond angle of 360ꢁ [18a]. In both complexes the one
˚
of Sn–S bond length (in 1 Sn–S(1) 2.466(7) A, in 2 Sn–
˚
S(2) 2.461(6) A) is shorter than the other (in 1 Sn–S(2)
˚
˚
2.739(9) A, in 2 Sn–S(1) 2.657(6) A) suggesting the unsym-
metrical coordination of the ligand. Further the shorter
Sn–S bond lengths are very close to the sum of the covalent
radii of tin and sulfur and the longer Sn–S distances are sig-
˚
nificantly less than the sum of van der Waals radii (4.0 A)
[18b]. The Sn–C distances (in 1 Sn–C(1) 2.109(3) A; Sn–
˚
˚
˚
C(2) 2.112(3) A, in 2 Sn–C(8) 2.129(2) A; Sn–C(14)
˚
2.137(2) A) are similar to those found in earlier reports
[12,13]. The Sn–Cl bond lengths (in
1
Sn–Cl(1)
Table 2
Selected bond lengths (A) and bond angles (ꢁ) for complex (1) and (3)
˚
Fig. 3. ORTEP drawing of the X-ray structure of complex (3).
Complex (1)
Complex (3)
˚
Bond lengths (A)
Sn(1)–C(1)
Sn(1)–C(2)
Sn(1)–S(1)
Sn(1)–Cl(1)
Sn(1)–S(2)
S(1)–C(3)
Table 2. From both figures and tables it can be seen that
the coordination geometry about tin atom is penta-coordi-
nated distorted trigonal bipyramidal with two R groups
attach to tin and S(1)/(S2) occupying equatorial positions
while Cl(1) and S(2)/S(1) occupy the apical position. In this
way, the ligand behaves as a bidentate species and chelates
the tin atom by means of sulfur atoms similar to
Ph2SnCl(PCDT) and Me2SnCl(PCDT) where PCDT =
piperidine-1-carbodithioate [12,13]. Due to being apart of
chelate the angle S(1)–Sn–S(2) is not 90ꢁ but only
68.25(2)ꢁ, so the S(2) cannot occupy exactly the corre-
sponding trans apical position of Cl(1) and the angle
between the apical groups is 154.19(3) for 1 [12,13]. For
complex 2 the S(2)–Sn–S(1) is only 69.98(18)ꢁ and the
angle Cl(1)–Sn–S(1) is 153.55(2)ꢁ for the same reason.
These values are again comparable with the analogous
Ph2SnCl(PCDT) and Me2SnCl(PCDT) where PCDT =
piperidine-1-carbodithioate. The sum of the equatorial
angles formed in complexes 1 and 3 is 358.37(10)ꢁ and
359.59(10)ꢁ, respectively, showing some distortion from
2.109(3)
2.112(3)
2.466(7)
2.485(8)
2.739(9)
1.743(3)
1.697(3)
1.317(3)
1.469(4)
1.471(3)
Sn(1)–C(8)
Sn(1)–C(14)
Sn(1)–S(2)
Sn(1)–Cl(1)
Sn(1)–S(1)
S(1)–C(1)
S(2)–C(1)
N(1)–C(1)
N(1)–C(2)
N(1)–C(7)
2.129(2)
2.137(2)
2.461(6)
2.467(6)
2.657(6)
1.720(2)
1.745(2)
1.302(3)
1.474(3)
1.481(3)
S(2)–C(3)
N(1)–C(3)
N(1)–C(9)
N(1)–C(4)
Bond angles(ꢁ)
C(1)–Sn(1)–C(2)
C(1)–Sn(1)–S(1)
C(2)–Sn(1)–S(1)
C(1)–Sn(1)–S(2)
C(2)–Sn(1)–S(2)
S(1)–Sn(1)–S(2)
Cl(1)–Sn(1)–S(2)
C(3)–S(1)–Sn(1)
N(1)–C(3)–S(2)
N(1)–C(3)–S(1)
N(1)–C(4)–C(5)
126.88(14)
112.96(9)
118.53(10)
94.76(9)
92.50(11)
68.25(2)
154.19(3)
91.23(9)
123.6(2)
119.6(2)
110.2(2)
C(8)–Sn(1)–C(14)
C(8)–Sn(1)–S(2)
C(14)–Sn(1)–S(2)
C(8)–Sn(1)–C(11)
C(14)–Sn(1)–C(11)
S(2)–Sn(1)–S(1)
Cl(1)–Sn(1)–S(1)
C(1)–S(1)–Sn(1)
N(1)–C(1)–S(1)
N(1)–C(1)–S(2)
N(1)–C(2)–C(3)
114.63(8)
122.21(6)
122.75(6)
96.76(6)
96.60(6)
69.98(18)
153.55(2)
83.94(7)
123.48(17)
120.41(17)
110.7(2)
Table 3
Antimicrobial activitya of the free ligand and their chloro-diorganotin(IV) complexes
Comp.
Fungi
T. longifusus
C. albicans
A. flavus
M. canis
F. solani
C. glaberata
HL
(1)
(2)
(3)
R
10
30
30
30
70
0
0
60
60
110.8
0
0
0
10
20
10
0
60
60
98.4
28
40
40
0
38
70
20
90
110.8
73.2
Bacteria
E. coli
B. subtilis
S. flexenari
S. aureus
P. aeruginosa
S. typhi
HL
(1)
(2)
(3)
R
12
18
26
18
35
15
20
25
18
38
15
20
25
20
32
20
22
24
20
38
20
22
20
20
29
20
20
20
18
28
a
The test done using the tube diffusion method (antifungal) and agar well diffusion method, well diameter, 6 mm; R, Standard drug; Miconazole and
Amphotericin.B (antifungal agent); Imipenum (antibacterial agent).

1802
S. Shahzadi et al. / Journal of Organometallic Chemistry 691 (2006) 1797–1802
˚
˚
2.485(8) A, in 2 Sn–Cl(1) 2.467(6) A) lie in the range of the
Acknowledgment
˚
normal covalent radii, 2.37–2.60 A [12,13,18].
Saqib Ali is thankful to Quaid-i-Azam University,
Islamabad for financial support.
3.6. Microbial assay
The free ligand 4-methyl-1-piperidine carbodithioic acid
and their chloro-diorganotin(IV) complexes were tested
against the bacterial strains Escherichia coli, Bacillus sub-
tilis, Shigella flexenari, Staphylococcus aureus, Pseudomo-
nas aeruginosa and Salmonella typhi by agar well
diffusion method [19] and the antifungal activity against
Trichophyton longifusus, Candida albicans, Aspergillus
flavus, Microsporum canis, Fusarium solani and Candida
glaberata. The results are listed in Table 3.
The antibacterial studies exhibited that the complexes 1–
3 have high activity towards all tested bacteria than the free
ligand. The antifungal studies by tube diffusion method
exhibited that the complexes 1–3 have high activity towards
all the tested fungi than the free ligand. It may be con-
cluded that metal coordination increases the activity as
compared to free ligand.
References
[1] E.I. Stiefel, K. Matsumoto, in: Transition Metal Sulfur Chemistry
ASC Symposium Series, vol. 653, American Chemical Society,
Washington, DC, 1995, p. 2.
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Chloro-diorganotin(IV) complexes of 4-methyl-1-piperi-
dine carbodithioic acid have been synthesized and charac-
terized. Detailed studies of reported complexes indicate
that their structures are trigonal bipyramidal geometry.
These complexes also checked for their antimicrobial activ-
ity against different bacteria and fungi by agar well diffu-
sion and tube diffusion methods, respectively. The
screening results show that reported compounds 1–3 exhi-
bit high antimicrobial activity as compared to free ligand
(4-methyl-1-piperidine carbodithioic acid).
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5. Supplementary material
Crystallographic data for the structural analysis have
been deposited with the Cambridge Crystallographic Data
Centre, CCDC Nos. 277901 and 277900 for complexes 1
and 3, respectively. Copies of these information may be
obtained free of charge from the Director, CCDC, 12
Union Road, Cambridge, CBZ 1EZ, UK (fax: +44 1223
336 033; email: deposit@ccdc.cam.ac.uk or www: http://
www.ccdc.cam.ac.uk).