Synthesis and characterization of organotin(IV) compounds with Schiff base of o-vanillin-2-thiophenoylhydrazone

Article abstract of DOI:10.1016/j.jorganchem.2006.03.003

Seven Schiff base adducts of organotin(IV), RSnLCl₂, which L is o-vanillin-2-thiophenoylhydrazone, and R is n-C₄H₉ (1), Me (2), Ph (3), and [R₂SnL], which L is o-vanillin-2-thiophenoylhydrazone, R is n-C₄H₉ (4), Me (5), Ph (6), PhCH₂ (7) have been synthesized. Those products were characterized by elemental analysis, IR, ¹H, ¹³C and ¹¹⁹Sn NMR spectra. The crystal and molecular structures of compounds 1, 4, and 6 have been determined by X-ray single crystal diffraction. In the crystal of compound 1 the tin atom is rendered six-coordinate in a distorted octahedral configuration by coordinating with the N atom of the Schiff base ligand, in compounds 4 and 6 the central tin atoms are five-coordinate in distorted trigonal-bipyramidal geometry and the comparison of the IR spectra reveal that disappearance of the bands assigned to carboxyl unambiguously conforms the ligand coordinate with the tin atom in enol form.

Full text of DOI:10.1016/j.jorganchem.2006.03.003

Journal of Organometallic Chemistry 691 (2006) 3103–3108
www.elsevier.com/locate/jorganchem
Note
Synthesis and characterization of organotin(IV) compounds with
Schiff base of o-vanillin-2-thiophenoylhydrazone
*
Han Dong Yin , Shao Wen Chen
Department of Chemistry, Liaocheng University, Liaocheng 252059, China
Received 17 January 2006; received in revised form 1 March 2006; accepted 2 March 2006
Available online 8 March 2006
Abstract
Seven Schiff base adducts of organotin(IV), RSnLCl2, which L is o-vanillin-2-thiophenoylhydrazone, and R is n-C4H9 (1), Me (2), Ph
(3), and [R2SnL], which L is o-vanillin-2-thiophenoylhydrazone, R is n-C4H9 (4), Me (5), Ph (6), PhCH2 (7) have been synthesized. Those
1
products were characterized by elemental analysis, IR, H, 13C and 119Sn NMR spectra. The crystal and molecular structures of com-
pounds 1, 4, and 6 have been determined by X-ray single crystal diffraction. In the crystal of compound 1 the tin atom is rendered six-
coordinate in a distorted octahedral configuration by coordinating with the N atom of the Schiff base ligand, in compounds 4 and 6 the
central tin atoms are five-coordinate in distorted trigonal-bipyramidal geometry and the comparison of the IR spectra reveal that dis-
appearance of the bands assigned to carboxyl unambiguously conforms the ligand coordinate with the tin atom in enol form.
ꢀ 2006 Elsevier B.V. All rights reserved.
Keywords: Organotin(IV); o-Vanillin-2-thiophenoylhydrazone; Crystal structures
1. Introduction
tions of compounds 1–7 are reported herein. Three of the
compounds have been studied by X-ray diffraction, and
reveal that the compounds have different structure. Further-
more, for compounds 6, 7, because of the presence of big
alkyl, the structure of compound 6 presences a monomer
and compound 4 rendered a weakly bridged dimer by the
weak interactions of Sn. . .O bond. The Schiff base ligand
function as tridentate chelates with O, N and O atoms.
Organotin(IV) complexes have been the subject of interest
for some time because of their biomedical and commercial
application [1]. In recent years, there have been more and
more reports on the synthesis, anti-tumor activities and
structural elucidations of various diorganotin derivatives
of carboxylic acid [2–5]. Increasing attention has also been
devoted to the organotin(IV) complexes with Schiff base
ligand in view of their special anti-tumour activities [6–14].
In addition to their anti-tumor activities, organotin(IV)
complexes with Schiff bases present an interesting variety
of structural possibilities [15]. We have recently reported
some diorganotin complexes of pyruvic acid isonicotinyl
hydrazone and pyruvic acid salicylhydrazone [16]. As an
extension of the studies of organotin(IV) complexes with
Schiff bases [17–19], we now synthesized seven organotin(IV)
complexes with Schiff base of o-vanillin-2-thiophenoylhyd-
razone. The details of the structure and special characteriza-
2. Experimental
2.1. Materials and instrumentation
All the solvents used in the reaction were of AR grade
and dried using standard literature procedures. The melt-
ing points were obtained with Kolfer micro melting point
apparatus and were uncorrected. IR spectra were recorded
1
on a Nicolet-460 spectrophotometer using KBr discs. H
13C and 119Sn NMR spectra were recorded on a Mercury
Plus-400 NMR spectrometer; chemical shifts were given
in ppm relative to Me4Si and Me4Sn in CDCl3 solvent. Ele-
mental analyses were performed in a PE-2400 II elemental
*
Corresponding author. Tel./fax: +866358239121.
E-mail address: handongyin@sohu.com (H.D. Yin).
0022-328X/$ - see front matter ꢀ 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2006.03.003

3104
H.D. Yin, S.W. Chen / Journal of Organometallic Chemistry 691 (2006) 3103–3108
analyzer; the chlorine analyses were performed by the oxy-
gen flask method.
2.3.2. [MeSnCl2(C13H11N2O3S)] (2)
Yield: 63%. Anal. Calc. for C14H14Cl2N2O3SSn: C,
35.03; H, 2.94; N, 5.84; Cl, 14.77. Found: C 34.92; H
1
2.2. Preparations of o-vanillin-2-thiophenoylhydrazone
2.83; N 5.85; Cl, 14.58%. H NMR (CDCl3, 400 MHz):
1.22 (s, 6 H, JSnAH = 79 Hz, SnACH3), 3.25 (s, 3H,
AOCH3), 7.15–7.32 (m, 3H, AC4H3S), 7.96 (s, 1H,
CANH), 8.51 (s, 1H, N@CH). 13C NMR (CDCl3,
400 MHz): 140.35 (CH@N), 165.68 (COAN), 56.12
(AOCH3), 148.78, 147.62, 136.98, 130.49, 128.51, 127.63,
120.37, 117.60, 116.92, 112.05 (aromatic carbons), 15.63
(SnACH3) ppm. 119Sn NMR (CDCl3): À383.9 ppm. IR
(KBr, cmÀ1): 3323 (m, NH), 1640 (s, C@N), 1457–1605
(m, Ph), 570 (m, SnAO), 539 (w, SnAC).
The Schiff base has been prepared with 2-thio-
phenoylhydrazide and o-vanillin in ethanol according to
the literature [20]. Yield: 69% (see Scheme 1).
2.3. Preparations of the compounds
Compounds 1–3 were prepared using the same proce-
dure as described for compound 1. The reaction mixture
of Schiff base (0.2753 g, 1.0 mmol), triethylamine
(1.2 mmol) were added to a solution of ethanol (30 ml),
n-butyltin trichloride, (0.2822 g, 1.0 mmol) was added,
continuing the reaction for 15 h under refluxing. Cooled
to room temperature filtered it and gradually removed by
evaporation under vacuum until solid product was
obtained. The solid was then re-crystallized from dichloro-
methane–hexane and yellow single crystal was formed by
slow evaporation at r.t.
Compounds 4–7 were prepared using the same proce-
dure as described for compound 4. The reaction was car-
ried out under nitrogen atmosphere with use of stranded
Schlenk technique. The Schiff base (0.2753 g, 1.0 mmol)
was added in the mixture of ethanol and benzene (V/V:
1/3) (30 ml) with sodium ethoxide (0.052 g, 1.0 mmol),
the mixture was stirred for 0.5 h, (C4H9)2SnCl2 (0.3038 g,
1.0 mmol) was added, stirring for 10 h under refluxing.
After cooling down to room temperature, filtered it and
evaporated to dryness, the solid was then recrystallized
from dichloromethane–hexane and yellow single crystal
was formed by slow evaporation at r.t.
2.3.3. [PhSnCl2(C13H11N2O3S)] (3)
Yield: 70%. Anal. Calc. for C19H16Cl2N2O3SSn: C,
42.10; H, 2.97; N, 5.17, Cl, 13.08. Found: C, 42.03; H,
1
2.90; N, 5.08; Cl, 12.90%. H NMR (CDCl3, 400 MHz):
2.49 (s, 3H, ACH3), 3.38 (s, 3H, AOCH3), 6.72–7.16 (m,
5H, PhAH), 7.20–7.38 (m, 3H, AC4H3S), 7.84 (s, 1H,
CANH), 8.55 (s, 1H, N@CH). 13C NMR (CDCl3,
400 MHz): 142.35 (CH@N), 173.15 (COAN), 55.97
(AOCH3), 150.78, 148.42, 140.12, 135.83, 132.41, 130.56,
125.45, 122.43, 120.37, 117.13 (aromatic carbons),
139.56,139.32, 135.97 136.43, 128.99, 128.76, 126.76
(SnAPh) ppm. 119Sn NMR (CDCl3): À365.6 ppm. IR
(KBr, cmÀ1): 3337 (m, CANH), 1633 (s, C@N), 1453–
1597 (m, Ph), 566 (m, SnAO), 533 (w, SnAC).
2.3.4. [(n-C4H9)2Sn[(C13H10N2O3S)]2 (4)
Yield: 65%, Anal. Calc. for C42H56N4O6S2Sn2: C, 49.72;
1
H, 5.56; N, 5.52; Found: C, 49.55; H, 5.43; N, 5.39%. H
NMR (CDCl3, 400 MHz): 0.91 (t, 12 H, CH3), 1.32–1.75
(m, 24H, SnCH2CH2CH2), 3.83 (s, 6H, AOCH3),
6.80–6.89 (m, 6H, PhAH), 7.20–7.38 (m, 6H, AC4H3S),
8.49 (s, 1H, N@CH). 13C NMR (CDCl3, 400 MHz):
140.36 (CH@N), 164.16 (COAN), 57.31 (AOCH3),
151.49,150.15, 137.72, 137.45, 135.89, 128.25, 122.97,
121.13, 119.52, 114.13 (aromatic carbons), 30.25, 28.76,
19.86, 15.42 (SnABu) ppm. 119Sn NMR (CDCl3): À190.6
ppm. IR (KBr, cmÀ1): 1625 (s, C@NAN@C), 1633 (s,
C@N), 1459–1610 (m, Ph), 547 (m, SnAO), 534 (w,
SnAC).
2.3.1. [n-C4H9SnCl2(C13H11N2O3S)] (1)
Yield: 78%, Anal. Calc. for C17H20Cl2N2O3SSn: C,
39.11; H, 3.86; N, 5.37; Cl, 13.58. Found: C, 39.03; H,
1
3.78; N, 5.49; Cl, 13.39%. H NMR (CDCl3, 400 MHz):
0.95 (t, 3H, ACH3), 1.34–1.79 (m, 6H, SnCH2CH2CH2A),
3.80 (s, 3H, AOCH3), 7.17–7.36 (m, 3H, AC4H3S), 6.79–
7.12 (m, 3H, PhAH), 7.80 (s, 1H, CANH), 8.60 (s, 1H,
N@CH). 13C NMR (CDCl3, 400 MHz): 142.55 (CH@N),
168.25 (COAN), 56.26 (AOCH3), 149.32, 148.42, 138.12,
131.89, 129.51, 128.25, 122.19, 119.13, 118.92, 114.13 (aro-
matic carbons), 26.93, 26.65, 20.90, 13.42 (SnABu) ppm.
119Sn NMR (CDCl3): À343.6 ppm. IR (KBr, cmÀ1): 3346
(m, NH), 1639 (s, C@N), 1450–1600 (m, Ph), 540 (m,
SnAO), 537 (w, SnAC).
2.3.5. [(CH3)2Sn(C13H10N2O3S)]2 (5)
Yield: 59%. Anal. Calc. for C30H32N4O6S2Sn2: C, 42.58;
1
H, 3.81; N, 6.62. Found: C, 42.33; H, 3.69; N, 6.50%. H
NMR (CDCl3, 400 MHz): 1.19 (s, 12 H, JSnAH = 75 Hz,
SnACH3), 7.23–7.43 (m, 6H, AC4H3S), 3.89 (s, 6H,
AOCH3), 6.77–6.86 (m, 6H, PhAH), 8.53 (s, 2H, N@CH).
13C NMR (CDCl3, 400 MHz): 142.78 (CH@N), 163.89
(COAN), 55.37 (AOCH3), 150.98, 150.07, 138.32, 137.65,
136.90, 129.25, 121.68, 121.01, 118.39, 115.36 (aromatic
carbons), 16.79 (SnACH3) ppm. 119Sn NMR (CDCl3):
À179.9 ppm. IR (KBr, cmÀ1): 1616 (s, C@NAN@C),
1639 (s, C@N), 1494–1613 (m, Ph), 563 (m, SnAO), 539
(w, SnAC).
O
N
N
S
H
HO
O
CH3
Scheme 1.

H.D. Yin, S.W. Chen / Journal of Organometallic Chemistry 691 (2006) 3103–3108
3105
2.3.6. [(C6H5)2Sn(C13H10N2O3S)(CH3OH)] (6)
Yield: 73%, Anal. Calc. for C26H24N2O4SSn: C, 53.91;
H, 4.17; N 4.83. Found: C, 53.75; H, 4.06; N, 4.90%. H
The structure was solved by a direct method and refined
by a full-matrix least-squares procedure based on F2 using
the SHELXL-97 program system [21]. All data were collected
at 298(2) K using graphite-monochromated Mo Ka
1
NMR (CDCl3, 400 MHz): 3.35 (s, 3H, AOCH3), 3.76 (s,
3H, ArOCH3), 4.13 (s, 1H, OAH), 6.89–7.06 (m, 3H,
PhAH), 7.19–7.38 (m, 3H, AC4H3S), 7.45–7.76 (m, 10H,
SnAC6H5), 8.60(s, 1H, N@CH). 13C NMR (CDCl3,
400 MHz): 146.73 (CH@N), 170.89 (COAN), 56.37
(AOCH3), 148.58, 147.27, 138.86, 137.65, 136.09, 129.75,
121.16, 120.36, 118.29, 114.36 (aromatic carbons), 136.29,
130.36, 129.89, 128.95, 126.86, 123.48 (SnAPh) ppm.
119Sn NMR (CDCl3): À168.7 ppm. IR (KBr, cmÀ1): 3386
t(OH), 1615 (s, C@NAN@C), 1631 (s, C@N), 1453–1600
(m, Ph), 566 (m, SnAO), 533 (w, SnAC).
˚
(k = 0.71073 A) radiation and the /–x scan technique.
All non-hydrogen atoms were included in the model at
their calculated positions. The positions of hydrogen atoms
were calculated, and their contributions in structure factor
calculations were included.
3. Results and discussion of X-ray crystal structures
3.1. Structure of [n-C4H9SnCl2(C13H11N2O3S)] (1)
The molecular structure is shown in Fig. 1. The crystal-
lographic data and selected bond lengths and angles are
given in Tables 1 and 2. The molecular structure in the
Fig. 1 shows that compound 1 is a monomer structure in
which the Sn(1) atom and C(1), C(2), C(3), O(1), N(1)
atoms form a six membered ring, while the Sn(1) atom
and C(9), O(3), N(1), N(2) atoms form a five membered
ring. The dihedral angle between the two rings is 3.4(2)ꢁ.
In compound 1, the tin atom is rendered a distorted octa-
hedral geometry and the equatorially positions were occu-
pied by the nitrogen atom and two oxygen atoms from the
tridentate Schiff base ligand, and one C atom from the n-
butyl. In the tridentate Schiff base ligand the CANANAC
chain can indicate by the intermediate C(1)AN(1)
2.3.7. [(C6H5CH2)2Sn(C13H10N2O3S)] (7)
Yield: 69%, Anal. Calc. for C27H24N2O3SSn: C, 56.37;
H, 4.20; N, 4.87. Found: C, 56.20; H, 4.09; N, 4.95%. H
1
NMR(CDCl3, 400 MHz): 3.25 (t, 4H, JSnAH = 88 Hz,
PhCH2Sn), 3.43 (s, 3H, AOCH3), 6.55–7.63 (m, 16H,
ArAH & AC4H3S), 8.55 (s, 1H, N@CH). 13C NMR
(CDCl3, 400 MHz): 146.78 (CH@N), 169.56 (COAN),
55.78 (AOCH3), 149.98, 148.07, 138.32, 138.09, 136.46,
129.33, 121.68, 121.01, 118.39, 115.28 (aromatic carbons),
31.63, 139.30, 133.83, 129.36, 128.76, 126.49, 124.56
(SnACH2APh) ppm. 119Sn NMR (CDCl3): À179.5 ppm.
IR (KBr, cmÀ1): 1622 (s, C@N), 1609 (s, C@NAN@C),
1453–1596 (m, Ph), 654 (m, SnAO), 547 (m, SnAC).
˚
˚
[1.285(7) A], N(1)AN(2) [1.384(6) A] and N(2)AC(9)
˚
2.4. Crystallographic measurement
[1.340(6) A]. The axially positions were occupied by two
Cl atoms, and the angle of Cl(1)ASn(1)ACl(2) is
167.95(5)ꢁ, which is deviates from the linear angle 180ꢁ.
However, the geometry around the tin atom is not as dis-
torted as reported for the other six-coordinated organotin
tetradentate ligand compounds [22]. The Sn(1)AO(1) bond
Crystallographic data and refinement details are given in
Table 1. All X-ray crystallographic data were collected on a
Bruker SMART CCD 1000 diffractometer. A criterion of
observability was used for the solution and refinement.
Table 1
Crystallographic data of compounds 1, 4 and 6
Compound
1
4
6
Empirical formula
Formula weight
Crystal system
C17H20Cl2N2O3SSn
521.99
Monoclinic
P21/C
C42H56N4O6S2Sn2
8115.26
Monoclinic
P21/C
C26H24N2O4SSn
564.21
Monoclinic
P21/C
Space group
Unit cell dimensions
˚
a (A)
9.8759(16)
18.061(3)
12.328(2)
99.897(2)
2166.3(6)
4
13.182(4)
23.643(7)
18.998(4)
130.402(13)
4059(2)
11.204(11)
11.474(11)
19.222(19)
99.621(15)
2436(4)
˚
b (A)
˚
c (A)
b (ꢁ)
Volume (A )
3
˚
Z
1
4
Calculated density (mg/m3)
F(000)
1.597
1036
1.494
2064
1.538
1136
Crystal size (mm)
Scan range h (ꢁ)
Total/unique/Rint
Goodness-of-fit on F2
Refined parameters
R1/wR2
0.48 · 0.39 · 0.23
2.00–25.01
11161/3819/0.0372
1.000
184
0.0373/0.0967
1.510
0.44 · 0.21 · 0.11
1.77–25.01
22351/7764/0.0819
1.001
505
0.0835/0.2024
1.249
0.43 · 0.39 · 0.38
2.07–25.01
12009/4255/0.0733
1.002
304
0.0494/0.1148
1.166
l (mmÀ1
max/qmin (e AÀ3
)
q
)
0.878 and À0.916
1 1.646 and À0.789
1.323 and À0.832

3106
H.D. Yin, S.W. Chen / Journal of Organometallic Chemistry 691 (2006) 3103–3108
Fig. 1. Molecular structure of compound 1.
Table 2
From the Figs. 2 and 3 it can be seen that each tin atom is
rendered five-coordinate by coordinating with the nitrogen
atom from the Schiff base ligand with a distorted trigonal
bipyramidal geometry, surrounded axially by two C atoms
from the alkyl and equatorially by one N atom, two O
atoms from the Schiff base ligand. So the Schiff base ligand
coordinated to the tin atom as a tridentate ligand.
˚
Selected bond distances (A) and angles (ꢁ) for compounds 1, 4 and 6
1
Sn(1)AO(1)
Sn(1)AN(1)
Sn(1)AO(3)
Cl(1)ASn(1)ACl(2)
2.053(3)
2.236(4)
2.181(3)
N(1)AN(2)
N(1)AC(1)
N(2)AC(9)
1.384(6)
1.285(7)
1.340(6)
167.95(5)
4
Sn(1)AO(1)
2.201(7)
155.3(5)
92.4(5)
89.6(5)
100.8(4)
103.2(4)
Sn(1)AO(1)#1
2.848(8)
71.7(4)
95.1(4)
94.2(4)
153.0(3)
81.3(3)
In compound
bond length of 2.227(10) A is shorter than those of
4
the intramolecular Sn(1)AO(1)
˚
C(18)ASn(1)AC(14)
C(18)ASn(1)AO(3)
C(14)ASn(1)AO(3)
C(18)ASn(1)AN(1)
C(14)ASn(1)AN(1)
O(3)ASn(1)AN(1)
C(18)ASn(1)AO(1)
C(14)ASn(1)AO(1)
O(3)ASn(1)AO(1)
N(1)ASn(1)AO(1)
{Ph2Sn[4-NC5H4AC(O)N2C(CH3)CO2](H2O)}2 Æ CH2Cl2 Æ
˚
H2O} [2.385(6) A] and {(PhCH2)2Sn[4-NC5H4AC(O)N2C-
˚
(CH3)CO2](H2O)}2 [2.383(3) A] [16], but is longer than the
Sn(1)AO(1) bond length of 2.067(5) A in the compound 6.
˚
6
In compound 4, the Sn(1)AO(1)#1 [#1: Àx, 2 À y, 1 À z]
Sn(1)AN(1)
C(20)ASn(1)AC(14)
C(20)ASn(1)AO(3)
2.152(6)
128.9(3)
93.2(3)
Sn(1)AO(1)
C(14)ASn(1)AO(3)
2.067(5)
94.1(3)
˚
distance of 2.848(8) A is markedly greater than the sum
of the covalent radii for SnAO, but is considerably less
than the sum of the Van der Waals radii. It is shown that
the O(1)#1 atom makes weak contacts with the Sn(1) atom.
Two molecules form a weak-bridged dimer with weak
interactions of Sn. . .O bonding. While in compound 6,
there was no intramolecular interaction between the Sn(1)
atom and O(1)#1 atom, which is due to the presence of
the big phenyl and make the compound stay as a mono-
mer. The packing of the molecules in a unit cell of com-
pound 6 can confirm this. The Sn(1)AN(1) bond length
#1: Àx, 2 À y, 1 À z.
˚
length is 2.053(3) A, and the Sn(1)AO(3) bond length is
˚
2.181(3) A, which is much less than the sum of the Van
˚
der Waals radii for Sn and O (3.68 A), indicating the signif-
icant contacts with the Sn(1) atom. The Sn(1)AN(1) dis-
tance is 2.236(4) A, which is greater than the sum of the
non-polar covalent radii 2.15 A, but is considerably less
˚
˚
˚
˚
than the sum of the Van der Waals radii (3.75 A) [23]
are 2.227(10) and 2.152(6) A in compounds 4 and 6, which
and should be considered as bonding interaction, indicat-
ing the strong tinAnitrogen interaction.
is shorter than the bond length in compound 1, indicating
the strong tin–nitrogen interaction.
The distorted trigonal bipyramidal geometry around the
tin atom is a result of the strain imposed by the tridentate
Schiff base ligand, and from the constraints imposed by the
five and six membered ring SnANANACAO and
SnANACACACAO. This is reflected in compound 4, the
angles of C(18)ASn(1)AO(3) 92.4(5)ꢁ, C(18)ASn(1)AO(1)
95.1(4)ꢁ and C(14)ASn(1)AO(1) 94.2(4)ꢁ are greater than
3.2. Structure of [(n-C4H9)2Sn[(C13H10N2O3S)]2 (4) and
[(C6H5)2Sn(C13H10N2O3S)] Æ (CH3OH) (6)
The molecular structure of compounds 4 and 6 is shown
in Figs. 2 and 3, respectively. The crystallographic data and
selected bond lengths and angles are given in Tables 1 and 2.

H.D. Yin, S.W. Chen / Journal of Organometallic Chemistry 691 (2006) 3103–3108
3107
Fig. 2. Molecular structure of compound 4.
Fig. 3. Molecular structure of compound 6.
90ꢁ. In contrast, the angles of C(14)ASn(1)AO(3) 89.6(5)ꢁ,
O(3)ASn(1)AN(1) 71.7(4)ꢁ and O(1)ASn(1)AN(1) 81.3(3)ꢁ
are less than 90ꢁ. The distorted geometry can also be seen
in the deviation from 180ꢁ of the angle C(18)ASn(1)AC(14)
155.3(5)ꢁ. While in compound 6 the angle of C(20)A
Sn(1)AC(14), C(20)ASn(1)AO(3) and C(14)ASn(1)AO(3)
are 128.9(3)ꢁ, 93.2(3)ꢁ and 94.1(3)ꢁ can also indicate the dis-
torted trigonal bipyramidal geometry. Those conclusionsare
supported by the X-ray single crystal diffraction study.
Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033;
or e-mail: deposit@ccdc.cam.ac.uk).
Acknowledgements
We acknowledged the National Natural Foundation PR
China (20271025) and the Shandong Province Science
Foundation.
References
4. Supplementary material
[1] S.J. de Mora, in: S.J. de Mora (Ed.), Tributyltin: Case Study of An
Environmental Contaminant, Cambridge University Press, London,
1996, pp. 1–20.
[2] S.W. Ng, J.M. Hook, M. Gielen, Appl. Organomet. Chem. 14 (2000) 1.
[3] Z.Q. Yang, X.Q. Song, Q.L. Xie, Chin. J. Org. Chem. 16 (1996) 111.
[4] W.G. Lu, J.X. Tao, X.Y. Li, Y.Z. Wang, Chin. J. Appl. Chem. 17
(2000) 126.
Crystallographic data for compounds 1, 4, 6 have been
deposited at the Cambridge Crystallographic Data Center
as supplementary publication numbers CCDC 293293,
291922 and 292084, respectively. Copies of available mate-
rial may be obtained on application to CCDC, 12 Union

3108
H.D. Yin, S.W. Chen / Journal of Organometallic Chemistry 691 (2006) 3103–3108
[5] H.D. Yin, C.H. Wang, Y. Wang, C.L. Ma, J.X. Shao, Chem. J.
Chin. Univ. 24 (2003) 68.
[17] H.D. Yin, M. Hong, Q.B. Wang, Indian J. Chem. 43A (2004) 2301.
[18] H.D. Yin, Q.B. Wang, Appl. Organomet. Chem. 18 (2004) 493.
[19] H.D. Yin, M. Hong, Appl. Organomet. Chem. 19 (2005) 401.
[20] Z.Y. Yang, L.F. Wang, J.G. Wu, X.Y. Li, Chin. J. Appl. Chem. 9
(1992) 508.
[6] R.S. Collinson, D.E. Ferton, Coord. Chem. Rev. 148 (1996) 19.
[7] A.K. Saxena, F. Huber, Coord. Chem. Rev. 95 (1989) 109.
[8] M. Gielen, Coord. Chem. Rev. 151 (1996) 41.
[9] A.J. Crowe, P.J. Smith, C.J. Cardin, H.E. Parge, F.E. Smith, Cancer
Lett. 24 (1984) 45.
[21] G.M. Sheldrick, SHELXS97 and SHELXL97, University of Go¨ttingen,
Germany, 1997.
[10] A.J. Crowe, P.J. Smith, J. Organomet. Chem. 244 (1982) 223.
[11] F. Huber, G. Roge, L. Carl, G. Atassi, F. Spreafico, S. Filippeschi,
R. Barbieri, A. Silvestri, E. Rivarola, G. Ruisi, F.D. Bianca, G.
Alonzo, J. Chem. Soc., Dalton Trans. (1985) 523.
[12] M. Gielen, Metal-Based Drugs 1 (1994) 213.
[13] A.J. Crowe, Drugs Future 2 (1987) 40.
[22] (a) D. Agustin, G. Rima, H. Gornitzka, J. Barrau, J. Organomet.
Chem. 592 (1999) 1 (and reference therein);
(b) M. Kutchta, J. Hahn, G. Parhin, J. Chem. Soc., Dalton Trans.
(1999) 3559;
(c) M.S. Singh, K. Tawad, A.K. Singh, Main Group Met. Chem. 22
(1999) 175;
[14] A.J. Crowe, P.J. Smith, G. Attasi, Chem-Biol. Interact. 32 (1980)
171.
[15] B.B. Tushar, S.M. Cheerfulman, W. Willem, B. Monique, et al., J.
Organomet. Chem. 690 (2005) 3080.
[16] H.D. Yin, M. Hong, Q.B. Wang, S.C. Xue, D.Q. Wang, J.
Organomet. Chem. 690 (2005) 1669.
(d) E. Sakuntala, E.N. Vasanta, Z. Naturforsch. 40b (1985) 1173;
(e) M. Hobday, T.D. Smith, J. Chem. Soc. Sect. A (1971) 1453;
(f) For an overall review of the crystallographic data for organotin
compound see: C.E. Holloway, M. Melnik, Main Group. Met.
Chem. 23 (2000) 1.
[23] A. Bondi, J. Phys. Chem. 68 (1964) 441.