Synthesis and characterization of ionic organotin compounds [R 2SnCl2(2-quin)]-(HNEt3)+ and crystal structures of [(2,4-Cl2-C6H3CH 2)2SnCl2(2-quin)]-(HNEt 3)+

Article abstract of DOI:10.1016/j.jorganchem.2004.11.003

Eight ionic organotin compounds [R₂SnCl₂(2-quin)] ^-(HNEt₃)⁺ have been synthesized by reactions of 2-quinH with R₂SnCl₂ (R = PhCH₂ 1, 2-Cl-C ₆H₄CH₂ 2, 4-Cl-C₆H ₄CH₂ 3, 2-F-C₆H₄CH₂ 4, 4-F-C₆H₄CH₂ 5, 4-CN-C₆H ₄CH₂ 6, Ph 7, 2,4-Cl₂-C₆H ₃CH₂ 8) in the presence of organic base NEt₃, and their structures have been characterized by elemental analysis, IR and multinuclear NMR (¹H, ¹³C, ¹¹⁹Sn) spectroscopies. The structure of [(2,4-Cl₂-C₆H ₃CH₂)₂SnCl₂(2-quin)] ^-(NEt₃)⁺ (8) has been determined by X-ray diffraction study. Studies show that compound 8 has a monomeric structure with the central tin atom six-coordinate in a distorted octahedral configuration and the nitrogen atoms of the 2-quin ligands are coordinating to the tin atom in all the eight compounds.

Full text of DOI:10.1016/j.jorganchem.2004.11.003

Journal of Organometallic Chemistry 690 (2005) 831–836
www.elsevier.com/locate/jorganchem
Communication
Synthesis and characterization of ionic organotin
compounds [R2SnCl2(2-quin)]À(HNEt3)+ and crystal structures
of [(2,4-Cl2-C6H3CH2)2SnCl2(2-quin)]À(HNEt3)+
*
Han Dong Yin , Qi Bao Wang, Sheng Cai Xue
Department of Chemistry, Liaocheng University, Liaocheng 252059, China
Received 2 October 2004; accepted 4 November 2004
Available online 8 December 2004
Abstract
Eight ionic organotin compounds [R2SnCl2(2-quin)]À(HNEt3)+ have been synthesized by reactions of 2-quinH with R2SnCl2
(R = PhCH2 1, 2-Cl-C6H4CH2 2, 4-Cl-C6H4CH2 3, 2-F-C6H4CH2 4, 4-F-C6H4CH2 5, 4-CN-C6H4CH2 6, Ph 7, 2,4-Cl2-C6H3CH2
8) in the presence of organic base NEt3, and their structures have been characterized by elemental analysis, IR and multinuclear
NMR (1H, 13C, 119Sn) spectroscopies. The structure of [(2,4-Cl2-C6H3CH2)2SnCl2(2-quin)]À(NEt3)+ (8) has been determined by
X-ray diffraction study. Studies show that compound 8 has a monomeric structure with the central tin atom six-coordinate in a dis-
torted octahedral configuration and the nitrogen atoms of the 2-quin ligands are coordinating to the tin atom in all the eight
compounds.
ꢀ 2004 Elsevier B.V. All rights reserved.
Keywords: Ionic organotin compound; 2-Quinaldate; Synthesis; Crystal structure
1. Introduction
organotin(IV) carboxylate. All the compounds have
been characterized by elemental analyses, IR and
NMR (1H, 13C and 119Sn) spectra, and the results of this
study are reported herein.
Organotin(IV) compounds with carboxylic acid are
widely used as biocides, fungicides and in industry as
homogeneous catalysts [1–5]. Recently, pharmaceutical
properties of organotin esters of carboxylic acid have
been investigated for their antitumour activity [6,7]. In
general, the biocidal activity of organotin complexes is
greatly influenced by the structure of the molecule and
the coordination number of the tin atoms [8–10]. Atassi
[11] assumed that water-soluble organotin compounds
are likely to be more active than compounds soluble
only in organic solvents. Therefore we synthesized eight
ionic organotin compounds [R2SnCl2(2-quin)]À(H-
NEt3)+, whose water solubility under physiological con-
ditions is expected to be improved with respect to
2. Experimental
2.1. Materials and methods
Diorganotin(IV) dichlorides were commercially avail-
able and used without further purification. The melting
points were obtained with Kolfer micro melting point
apparatus and were uncorrected. IR spectra were re-
corded on a Nicolet-460 spectrophotometer using KBr
discs and sodium chloride optics. 1H, 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.
*
Corresponding author. Tel.:/fax: +866358238121.
E-mail address: handongyin@sohu.com (H.D. Yin).
0022-328X/$ - see front matter ꢀ 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.jorganchem.2004.11.003

832
H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 831–836
Elemental analyses were performed in a PE-2400 II
elemental analyzer, and tin was estimated as SnO2.
H-7), 6.75–7.42 (8H, m, Ar–H), 2.97 (4H, d,
JSn–H = 80 Hz, SnCH2), 2.74 (6H, q, J = 7 Hz, CH2),
1.20 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
171.25 (COO), 153.08, 147.49, 132.10, 129.84, 128.55,
127.34, 126.32, 125.14, 124.77, 122.87, 122.00, 121.51,
118.92 (Ar–C), 31.73 (CH2Ar), 54.18 (NCH2), 7.47
(CH3). 119Sn NMR d À491.55. IR (KBr): mas(OCO),
2.2. Preparation of the complexes
2-Quinaldic acid (1.0 mmol) and NEt3 (1.0 mmol)
were added to a dichloromethane solution (20 ml) of
dialkyltin dichloride (1.0 mmol) and stirred for 1.5 h
at 30 ꢁC and then filtered. The filtrate was gradually re-
moved by evaporation under vacuum until solid product
was obtained. The solid was recrystallized from acetoni-
trile to give colorless crystals.
1658 cmÀ1; ms(OCO), 1355 cmÀ1; m(Sn–C), 556 cmÀ1
;
m(Sn–N), 485 cmÀ1; m(Sn–O), 453 cmÀ1
.
2.2.4. [(2-F-C6H4CH2)2SnCl2(2-quin)]À(HNEt3)+ (4)
0.49 g, yield 72%, m.p. 184–185 ꢁC. Anal. Calc. for
C30H34Cl2F2N2O2Sn: C, 52.82; H, 5.02; N, 4.11; Sn,
17.40. Found: C, 53.03; H, 5.10; N, 4.22; Sn, 17.57%.
1H NMR (CDCl3): d 11.06 (s, 1H, HNEt3), 8.83 (1H,
d, J = 7 Hz, H-3), 8.49 (1H, d, J = 8 Hz, H-4), 8.32
(1H, d, J = 8 Hz, H-9), 8.02 (1H, d, J = 6 Hz, H-6),
7.84 (1H, dd, J = 7, 4 Hz, H-8), 7.72 (1H, dd, J = 7,
4 Hz, H-7), 6.33–7.44 (8H, m, Ar–H), 2.95 (4H, d,
JSn–H = 89 Hz, SnCH2), 2.78 (6H, q, J = 7 Hz, CH2),
1.16 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
175.10 (COO), 154.22, 145.98, 137.05, 132.34, 130.37,
129.10, 127.34, 125.90, 125.18, 124.79, 123.33, 122.21,
121.43, 120.34, 113.86 (Ar–C), 33.45 (CH2Ar), 53.15
(NCH2), 7.38 (CH3). 119Sn NMR d À490.45. IR (KBr):
mas(OCO), 1661 cmÀ1; ms(OCO), 1327 cmÀ1; m(Sn–C),
2.2.1. [(PhCH2)2SnCl2(2-quin)]À(HNEt3)+ (1)
0.47 g, yield 72%, m.p. 192–194 ꢁC. Anal. Calc. for
C30H36Cl2N2O2Sn: C, 55.76; H, 5.62; N, 4.33; Sn,
18.37. Found: C, 55.57; H, 5.72; N, 4.28; Sn, 18.54%.
1H NMR (CDCl3): d 11.15 (s, 1H, HNEt3), 8.82 (1H,
d, J = 8 Hz, H-3), 8.50 (1H, d, J = 8 Hz, H-4), 8.23
(1H, d, J = 7 Hz H-9), 8.18 (1H, d, J = 8 Hz, H-6),
8.01 (1H, dd, J = 8, 5 Hz, H-8), 7.76 (1H, dd, J = 8, 4
Hz, H-7), 6.75–7.42 (10H, m, Ph-H), 2.91 (4H, d,
JSn–H = 84 Hz, SnCH2), 2.81 (6H, q, J = 7 Hz, CH2),
1.12 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
177.22 (COO), 150.63, 147.68, 136.10, 129.04, 128.47,
126.88, 125.21, 125.35, 122.73, 121.59, 117.64, 115.43,
109.12 (Ar–C), 30.58 (CH2Ar), 52.24 (NCH2), 7.53
(CH3). 119Sn NMR d À495.43. IR (KBr): mas(OCO),
545 cmÀ1; m(Sn–N), 486 cmÀ1; m(Sn–O), 462 cmÀ1
.
1655 cmÀ1; ms(OCO), 1330 cmÀ1; m(Sn–C), 575 cmÀ1
;
2.2.5. [(4-F-C6H4CH2)2SnCl2(2-quin)]À(HNEt3)+ (5)
0.50 g, yield 74%, m.p. 214–215 ꢁC. Anal. Calc. for
C30H34Cl2F2N2O2Sn: C, 52.82; H, 5.02; N, 4.11; Sn,
17.40. Found: C, 52.70; H, 4.87; N, 4.20; Sn, 17.25%.
1H NMR (CDCl3): d 11.11 (s, 1H, HNEt3), 8.77 (1H,
d, J = 8 Hz, H-3), 8.50 (1H, d, J = 7 Hz, H-4), 8.37
(1H, d, J = 7 Hz, H-9), 8.00 (1H, d, J = 6 Hz, H-6),
7.95 (1H, dd, J = 7, 4 Hz, H-8), 7.84 (1H, dd, J = 8,
4 Hz, H-7), 6.32–7.43 (8H, m, Ar–H), 2.94 (4H, d,
JSn–H = 86 Hz, SnCH2), 2.74 (6H, q, J = 7 Hz, CH2),
1.20 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
175.31 (COO), 155.89, 146.25, 132.77, 130.62, 129.61,
128.04, 126.65, 126.11, 125.27, 124.32, 123.78, 122.63,
118.10 (Ar–C), 32.89 (CH2Ar), 53.28 (NCH2), 7.47
(CH3). 119Sn NMR d À497.52. IR (KBr): mas(OCO),
m(Sn–N), 482 cmÀ1; m(Sn–O), 458 cmÀ1
.
2.2.2. {[(2-Cl-C6H4CH2)2SnCl2(2-quin)]À(HNEt3)+ (2)
0.56 g, yield 78%, m.p. 175–176 ꢁC. Anal. Calc. for
C30H34Cl4N2O2Sn: C, 50.39; H, 4.79; N, 3.92; Sn,
16.60. Found: C, 50.52; H, 4.71; N, 4.13; Sn, 16.47%.
1H NMR (CDCl3): d 11.13 (s, 1H, HNEt3), 8.85 (1H,
d, J = 8 Hz, H-3), 8.44 (1H, d, J = 7 Hz, H-4), 8.31
(1H, d, J = 8 Hz, H-9), 8.03 (1H, d, J = 6 Hz, H-6),
7.91 (1H, dd, J = 8, 5 Hz, H-8), 7.80 (1H, dd, J = 8, 5
Hz, H-7), 6.55–7.42 (8H, m, Ar–H), 3.02 (4H, d,
JSn–H = 84 Hz, SnCH2), 2.83 (6H, q, J = 7 Hz, CH2),
1.14 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
175.12 (COO), 152.70, 147.54, 136.88, 132.52, 130.54,
128.70, 127.67, 126.22, 125.53, 125.30, 124.64, 122.39,
120.61, 117.35, 115.42 (Ar–C), 31.48 (CH2Ar), 52.81
(NCH2), 7.33 (CH3). 119Sn NMR d À497.47. IR (KBr):
mas(OCO), 1668 cmÀ1 ms(OCO), 1365 cmÀ1; m(Sn–C),
1657 cmÀ1; ms(OCO), 1320 cmÀ1; m(Sn–C), 554 cmÀ1
;
m(Sn–N), 487 cmÀ1; m(Sn–O), 445 cmÀ1
.
2.2.6. [(4-CN-C6H4CH2)2SnCl2(2-quin)]À(HNEt3)+ (6)
0.47 g, yield 68%, m.p. 214–215 ꢁC. Anal. Calc. for
C32H34Cl2N4O2Sn: C, 55.20; H, 4.92; N, 8.05; Sn,
17.05. Found: C, 55.46; H, 5.05; N, 8.16; Sn, 17.13%.
1H NMR (CDCl3): d 11.04 (s, 1H, HNEt3), 8.70 (1H,
d, J = 8 Hz, H-3), 8.38 (1H, d, J = 8 Hz, H-4), 8.25
(1H, d, J = 8 Hz, H-9), 8.12 (1H, d, J = 7 Hz, H-6),
8.03 (1H, dd, J = 8, 3 Hz, H-8), 7.87 (1H, dd, J = 8,
4 Hz, H-7), 6.28–7.30 (8H, m, Ar–H), 2.93 (4H, d,
JSn–H = 88 Hz, SnCH2), 2.77 (6H, q, J = 7 Hz, CH2),
560 cmÀ1; m(Sn–N), 490 cmÀ1; m(Sn–O), 447 cmÀ1
.
2.2.3. {[(4-Cl-C6H4CH2)2SnCl2(2-quin)]À(HNEt3)+ (3)
0.46 g, yield 65%, m.p. 210–211 ꢁC. Anal. Calc. for
C30H34Cl4N2O2Sn: C, 50.39; H, 4.79; N, 3.92; Sn,
16.60. Found: C, 50.65; H, 4.80; N, 3.85; Sn, 16.72%.
1H NMR (CDCl3): d 11.10 (s, 1H, HNEt3), 8.56 (1H,
d, J = 8 Hz, H-3), 8.47 (1H, d, J = 8 Hz, H-4), 7.91
(1H, d, J = 6 Hz, H-9), 7.52–7.79 (3H, m, H-6, H-8 &

H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 831–836
833
1.23 (9H, t, J = 7 Hz, CH3). 13C NMR (CDCl3): d
R
O
171.84 (COO), 152.26, 137.40, 131.35, 130.68, 129.04,
128.57, 126.74, 126.48, 125.43, 124.65, 123.15, 122.64,
118.45 (Ar–C), 115.87 (CN), 32.67 (CH2Ar), 53.54
(NCH2), 7.42 (CH3). 119Sn NMR d À492.43. IR
(KBr): m(CN), 2215, mas(OCO), 1642 cmÀ1; ms(OCO),
O
C
Cl
Cl
+
-
6
9
Sn
4
]
[
(HNEt3)
5
N
7
8
3
COO
R
10
N
2
1
1333 cmÀ1; m(Sn–C), 544 cmÀ1; m(Sn–N), 490 cmÀ1
;
2-quin
[R2SnCl2(2-quin)]-(HNEt3)+
Scheme 1.
m(Sn–O), 459 cmÀ1
.
2.2.7. [Ph2SnCl2(2-quin)]À(HNEt3)+ (7)
0.48 g, yield 78%, m.p. 185–187 ꢁC. Anal. Calc. for
C28H30Cl2N2O2Sn: C, 54.58; H, 4.91; N, 4.55; Sn,
19.26. Found: C, 54.83; H, 5.09; N, 4.48; Sn, 19.19%.
1H NMR (CDCl3): d 11.00 (s, 1H, HNEt3), 8.84 (1H,
d, J = 7 Hz, H-3), 8.65 (1H, d, J = 8 Hz, H-4), 8.47
(1H, d, J = 7 Hz, H-9), 8.31 (1H, d, J = 6 Hz, H-6),
8.13 (1H, dd, J = 7, 4 Hz, H-8), 8.08 (1H, dd, J = 7,
4 Hz, H-7), 6.75–7.65 (10H, m, Ph–H), 2.77 (6H, q,
J = 7 Hz, CH2), 1.23 (9H, t, J = 7 Hz, CH3). 13C
NMR (CDCl3): d 172.58 (COO), 149.22, 147.47,
136.21, 131.75, 130.43, 128.76, 126.44, 125.08, 124.74,
123.58, 122.64, 121.33, 118.32 (Ar–C), 54.25 (NCH2),
7.56 (CH3). 119Sn NMR d À498.76. IR (KBr): mas(OCO),
Table 1
Crystallographic data of compound 8
Empirical formula
Formula weight
Temperature (K)
C30H32Cl6N2O2Sn
783.97
273(2)
˚
Wavelength (A)
0.71073
Monoclinic
P21/c
Crystal system
Space group
Unit cell dimensions
˚
a (A)
12.358(6)
16.765(7)
16.966(8)
110.315(6)
3297(3)
˚
b (A)
˚
c (A)
b (ꢁ)
Volume (A )
3
˚
À3
˚
q
Z
max/qmin (e A
)
0.923/À0.457
4
1.580
1654 cmÀ1; ms(OCO), 1348 cmÀ1; m(Sn–C), 491 cmÀ1
;
Calculated density (Mg/m3)
F(000)
m(Sn–N), 457 cmÀ1; m(Sn–O), 435 cmÀ1
.
1576
0.48 · 0.43 · 0.39
1.76–25.03
Crystal size (mm)
Scan range h (ꢁ)
Limiting indices h, k, l
Total/unique/Rint
Goodness-of-fit on F2
R1/wR2
2.2.8. [(2,4-Cl2-C6H3CH2)2SnCl2(2-quin)]À(HNEt3)+
(8)
À14 to 13, À19 to 19, À14 to 20
16,810/5821/0.0285
1.001
0.53 g, yield 68%, m.p. 165–166 ꢁC. Anal. Calc. for
C30H32Cl6N2O2Sn: C, 45.96; H, 4.11; N, 3.57; Sn,
15.14. Found: C, 45.91; H, 4.27; N, 3.49; Sn, 15.22%.
1H NMR (CDCl3): d 11.21 (s, 1H, HNEt3), 8.80 (1H,
d, J = 8 Hz, H-3), 8.63 (1H, d, J = 7 Hz, H-4), 8.42
(1H, d, J = 7 Hz, H-9), 8.20 (1H, d, J = 6 Hz, H-6),
8.04 (1H, dd, J = 8, 5 Hz, H-8), 7.97 (1H, dd, J = 8, 4
0.0366/0.1024
1.785
l (mmÀ1
)
the u À 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.
Hz, H-7), 6.55–7.65 (8H, m, Ph–H), 2.98 (4H, d, JSn–H
=
89 Hz, SnCH2), 2.75 (6H, q, J = 7 Hz, CH2), 1.25 (9H,
t, J = 7 Hz, CH3). 13C NMR (CDCl3): d 174.04
(COO), 152.56, 148.43, 137.02, 133.32, 132.45, 129.34,
128.74, 127.32, 125.98, 126.43, 124.76, 123.45, 120.56,
121.23, 118.80 (Ar–C), 34.49 (CH2Ar), 54.21 (NCH2),
7.58 (CH3). 119Sn NMR d À491.32. IR (KBr): mas(OCO),
3. Results and discussions
1666 cmÀ1; ms(OCO), 1339 cmÀ1; m(Sn–C), 568 cmÀ1
;
3.1. Physical properties
m(Sn–N), 488 cmÀ1; m(Sn–O), 457 cmÀ1 (see Scheme 1).
Physical data for compounds 1–8 are shown above.
All the compounds are colorless crystals. They are solu-
ble in many organic solvents as CCl4, CHCl3, C6H6,
(CH3)2CO and C2H5OH, but insoluble in hexane, petro-
leum ether and slightly soluble in water.
2.3. X-ray crystallography
Crystallographic data and refinement details are
given in Table 1. All X-ray crystallographic data were
collected on a Bruker SMART CCD 1000 diffractome-
ter. A criterion of observability was used for the solution
and refinement. The structure was solved by a direct
method and refined by a full-matrix least-squares proce-
dure based on F2 using the SHELXL-97 program system.
All data were collected at 298(2) K using graphite-
3.2. IR data
The infrared spectra of diorganotin(IV) compounds
have been recorded and some important assignments
are shown above. The Dm(mas(CO2) À ms(CO2)) value is
used to determine the nature of bonding of carboxylate
˚
monochromated Mo Ka (k = 0.71073 A) radiation and

834
H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 831–836
to tin(IV) compounds according to the previous report
[12]. It is generally believed that the difference in Dm be-
tween asymmetric (mas(CO2)) and symmetric ((ms(CO2))
absorption frequencies below 200 cmÀ1 for the bidentate
carboxylate moiety, but greater than 200 cmÀ1 for the
unidentate carboxylate moiety [13]. Study shows that
the values of Dm of the complex 1–8 are between 303
and 327 cmÀ1 and this strongly indicate that these eight
title compounds adopt unidentate carboxylate structure
[14]. Compared with the free ligand the new occurrence
of the bands in the region of 482–491 cmÀ1 for all the
eight compounds were assigned to the Sn–N vibrations,
and the bands in the region of 435–462 cmÀ1 were as-
signed to the Sn–O vibrations according to the literature
[15,16].
1
3.3. H, 13C and 119Sn NMR Spectra
The 1H NMR of compounds 1–6, and 8 show that the
chemical shifts of the protons of methylene on the ben-
zyl groups exhibit signals at the region 2.91–3.02 ppm as
doublet which are caused by tin (119Sn) hydrogen cou-
pling. And the spin–spin coupling constant JSn–H is
equal 84–90 Hz. The signals at 7.72–8.85 as mutipliplic-
ity for all the eight compounds are assigned to the pro-
tons of 2-quin ligand, which are shifting slightly to the
low field compared with the free ligand 7.68–9.02.
The 13C NMR spectral of all the compounds shows
significant downfield shifts of all carbon resonances
compared with the free ligand. The shift may be the con-
sequence of an electron density transfer from the ligand
to the acceptor.
Fig. 1. Molecular structure of compound 8.
˚
(2.0544 and 2.110 A), but a little longer than that of
the corresponding distances found in [(PhCH2)3Sn
˚
(O2CC5H4N) Æ (H2O)]n [19] (2.188(4) A). The Sn–N
˚
bond distance, 2.539(4) A, is longer than the sum of
˚
the covalent radii of Sn and N (2.15 A), but considerably
˚
shorter than the sum of the van der Waals radii (3.75 A)
and should be considered as a bonding interaction,
which is similar to other crystal structures of organotin
compounds containing the 2-pyridine and 2-quin car-
boxylate ligands. In the polymer [Me2SnCl(2-pic)]n [20]
the two unique Sn–N bond distances are 2.50(3) and
The 119Sn chemical shift values in eight compounds
are found to be in the range of À490.45 to À498.76
ppm. The appearance of chemical shift values in this re-
gion indicates six-coordination environment [17] around
the central tin atoms in these complexes.
˚
2.47(2) A, in the polymer [Me2Sn(2-pic)2]n [21] the two
˚
Sn–N bond distances are 2.507(4) and 2.477(4) A and
in {[nBu2Sn(2-pic)]2O}2 and Me2Sn(2-quin)2 [18,22] the
Sn–N bond distances are 2.550(5), 3.150(5), 2.594(3)
˚
and 2.473(4) A, respectively. The Sn–Cl bond lengths
˚
˚
3.4. X-ray studies of [(2,4-Cl2-C6H3CH2)2SnCl2-
(2-quin)2]À(HNEt3)+ (8)
are 2.5611(14) A for Sn(1)–Cl(1) and 2.4535(16) A
for Sn(1)–Cl(2) lying in the range of the normal covalent
˚
radii 2.37–2.60 A [23].
The molecular structure of compound 8 is shown in
Fig. 1. All hydrogen atoms have been omitted for the
purpose of clarity. Table 2 lists selected bond lengths
and angles for compound 8.
In the (2,4-Cl2-C6H3CH2)2SnCl2(2-quin)2]À anion,
the 2-quin ligand coordinates to the tin atom in biden-
tate fashion by one carboxyl group oxygen atom and
quinoline ring nitrogen atom, which made the angle of
oxygen atom and nitrogen atom occupy equatorial place
obviously deviating from the standard octahedron an-
gle. For example: the angles of one oxygen atom, one
nitrogen atom and two chlorine atoms around Sn(1)
atom are O(1)–Sn(1)–N(1) 69.62(11)ꢁ, N(1)–Sn(1)–
Cl(1) 108.15(9)ꢁ, Cl(2)–Sn(1)–Cl(1) 95.66(4)ꢁ, O(1)–
Sn(1)–Cl(2) 86.56(9)ꢁ. All angles deviate from 90ꢁ, but
the sum of these angles is 360.02ꢁ, which shows that
these atoms are in the same plane. Furthermore, the
bond angles 177.72(9)ꢁ for O(1)–Sn(1)–Cl(1),
170.73(19)ꢁ for C(11)–Sn(1)–C(18) and 156.17(9)ꢁ for
Compound
8
consists of [(2,4-Cl2-C6H3CH2)2-
SnCl2(2-quin)2]À anion and the (HNEt3)+ cation. The
(HNEt3)+ cation in general position balances the charge.
The tin atom is six-coordinate in a distorted octahedral
configuration in [(2,4-Cl2-C6H3CH2)2SnCl2(2-quin)2]À
anion. The central tin atom is surrounded equatorial
by one oxygen and one nitrogen atom from 2-quin li-
gand and two chlorine atoms and axially by two carbon
atoms of the tin-bound 2,4-dichlorobenzyl groups.
˚
In compound 8, the Sn–O bond length of 2.196(3) A
is a little shorter than that in {[nBu2Sn(2-pic)]2O}2 [18]

H.D. Yin et al. / Journal of Organometallic Chemistry 690 (2005) 831–836
835
Table 2
Selected bond distances (A) and angles (ꢁ) for compound 8
˚
Sn(1)–C(11)
2.169(5)
Sn(1)–C(18)
2.172(5)
Sn(1)–O(1)
Sn(1)–Cl(1)
2.196(3)
2.5611(14)
1.744(5)
1.731(6)
1.323(5)
1.484(7)
1.540(9)
1.238(5)
1.386(6)
170.73(19)
86.70(16)
96.24(16)
87.18(5)
69.62(11)
88.57(13)
177.72(9)
108.15(9)
130.4(3)
117.9(3)
123.0(4)
114.3(5)
Sn(1)–N(1)
Sn(1)–Cl(2)
2.539(4)
2.4535(16)
1.732(55)
1.728(6)
1.379(6)
1.503(7)
1.270(5)
1.516(6)
1.365(8)
90.85(15)
92.53(14)
86.56(9)
83.58(17)
156.17(9)
93.56(13)
95.66(4)
111.0(3)
123.9(3)
118.2(3)
124.6(4)
115.1(5)
Cl(3)–C(13)
Cl(5)–C(20)
Cl(4)–C(15)
Cl(6)–C(22)
N(1)–C(2)
N(2)–C(29)
N(1)–C(10)
N(2)–C(25)
N(2)–C(27)
O(2)–C(1)
C(2)–C(3)
O(1)–C(1)
C(1)–C(2)
C(3)–C(4)
C(11)–Sn(1)–C(18)
C(18)–Sn(1)–O(1)
C(18)–Sn(1)–Cl(2)
C(11)–Sn(1)–N(1)
O(1)–Sn(1)–N(1)
C(11)–Sn(1)–Cl(1)
O(1)–Sn(1)–Cl(1)
N(1)–Sn(1)–Cl(1)
C(10)–N(1)–Sn(1)
C(12)–C(11)–Sn(1)
O(2)–C(1)–O(1)
N(2)–C(29)–C(30)
C(11)–Sn(1)–O(1)
C(11)–Sn(1)–Cl(2)
O(1)–Sn(1)–Cl(2)
C(18)–Sn(1)–N(1)
Cl(2)–Sn(1)–N(1)
C(18)–Sn(1)–Cl(1)
Cl(2)–Sn(1)–Cl(1)
C(2)–N(1)–Sn(1)
C(1)–O(1)–Sn(1)
C(19)–C(18)–Sn(1)
N(1)–C(2)–C(3)
C(26)–C(25)–N(2)
ies of this information may be obtained from The Direc-
tor, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK
(fax: +44-1233-336-033; e-mail: deposit@ccdc.cam.ac.
uk).
Acknowledgements
We acknowledged the National Natural Foundation
PR China (20271025) and the Shandong Province
Science Foundation (L2003B01), and the state Key
Laboratory of Crystal Materials, Shandong University,
PR China.
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