Synthesis and characterization of a linked, π-π stacked organotin compound of 2-mercapto-6-nitrobenzothiazolyl diphenyltin chloride with 2-ethoxyl-6-nitrobenzothiazole

Article abstract of DOI:10.1139/v03-087

The new organotin compound, Ph₂Sn(Cl)[S(C₇H ₃N₂O₂S)]·[(C₇H ₃N₂O₂S)OEt], assembled by an intermolecular aromatic benzothiazole-benzothiazole π-π stacking interaction, has been synthesized by the reaction of diphenyltin dichloride with 2-mercapto-6- nitrobenzothiazole. The title compound was characterized by elemental, IR, ¹H NMR, and X-ray crystallography analyses. Single-crystal X-ray diffraction data reveals that the title compound has two different molecular components. The component Ph₂Sn(Cl)[S(C₇H ₃N₂O₂S)] has a pentacoordinate tin, which further forms an infinite one-dimensional chain by intermolecular non-bonded Cl...S interactions, resulting in an intercalation lattice that holds (C₇H₃N₂O₂S)OEt molecules. The formation of the molecule (C₇H₃N₂O ₂S)OEt as well as its intercalated mechanism has also been discussed.

Full text of DOI:10.1139/v03-087

825
Synthesis and characterization of a linked, π-π
stacked organotin compound of 2-mercapto-6-
nitrobenzothiazolyl diphenyltin chloride with 2-
ethoxyl-6-nitrobenzothiazole
Chunlin Ma, Qin Jiang, and Rufen Zhang
Abstract: The new organotin compound, Ph2Sn(Cl)[S(C7H3N2O2S)]·[(C7H3N2O2S)OEt], assembled by an intermolecular
aromatic benzothiazole–benzothiazole π-π stacking interaction, has been synthesized by the reaction of diphenyltin di-
1
chloride with 2-mercapto-6-nitrobenzothiazole. The title compound was characterized by elemental, IR, H NMR, and
X-ray crystallography analyses. Single-crystal X-ray diffraction data reveals that the title compound has two different
molecular components. The component Ph2Sn(Cl)[S(C7H3N2O2S)] has a pentacoordinate tin, which further forms an in-
finite one-dimensional chain by intermolecular non-bonded Cl···S interactions, resulting in an intercalation lattice that
holds (C7H3N2O2S)OEt molecules. The formation of the molecule (C7H3N2O2S)OEt as well as its intercalated mecha-
nism has also been discussed.
Key words: organotin, assemble, π-π stacking interaction, 2-mercapto-6-nitrobenzothiazole, non-bonded interaction,
crystal structure.
Résumé : Le nouveau composé organostannique Ph2Sn(Cl)[S(C7H3N2O2S)]·[(C7H3N2O2S)OEt], assemblé par interaction
aromatique intermoléculaire d’empilement π-π benzothiazole–benzothiazole, a été synthétise par la réaction du dichlo-
rure de diphénylétain avec le 2-mercapto-6-nitrobenzothiazole. Le composé mentionné dans le titre a été caractérisé par
1
des analyses élémentaires, IR, de RMN H et par diffraction des rayons X sur un cristal unique qui révèle qu’il est
formé de deux composantes moléculaires différentes. Le composant Ph2Sn(Cl)[S(C7H3N2O2S)] comporte un atome
d’étain pentacoordonné qui forme une chaîne infinie monodimensionnelle par le biais d’interactions intermoléculaires
non liées Cl···S qui sert de réseau d’intercalation pour retenir des molécules de (C7H3N2O2S)OEt. On discute aussi de
la formation de la molécule de (C7H3N2O2S)OEt ainsi que du mécanisme d’intercalation.
Mots clés : organostannique, assemblage, interaction d’empilement π-π, 2-mercapto-6-nitrobenzothiazole, interaction
non liée, structure cristalline.
[Traduit par la Rédaction] Ma et al. 831
Introduction
While tin is generally classified as a hard acid, many
organotin—sulfur bonded complexes are known. To date
only a few papers have been published on the X-ray struc-
tures of organotin(IV) complexes formed with thiol S and
heterocyclic N (3). To investigate these kinds of complex
structures, we used the reaction of diphenyltin dichloride
with 2-mercapto-6-nitrobenzothiazole, and we wished to gain
a one- or two-dimensional complex by the coordination of
sulfur and nitrogen atoms with tin. To our surprise, we ob-
tained an infinite one-dimensional linked compound assem-
bled by aromatic benzothiazole–benzothiazole π-π stacking
interactions. π-π stacking interaction has been extensively
studied in recent years (4–6), including that of phenyl–
phenyl (7), imidazole–imidazole (8), and so on. It has been
proved that this strong attractive interaction can stabilize the
packing of aromatic molecules in crystals (9) and play an
important part in the field of host–guest chemistry (10).
Through in-depth investigation into the intermolecular inter-
actions, new light may be thrown on supramolecular archi-
tecture of organotin complexes possessing a particular
structure and property. In this paper, we characterized the
The coordination chemistry of tin is extensive with vari-
ous geometries and coordination numbers known for both
inorganic and organometallic complexes (1). Higher coordi-
nation numbers can be generated either by inter- and (or)
intramolecular interaction, especially in complexes where tin
bonds to electronegative atoms, such as oxygen, nitrogen,
and sulfur. Studies of adducts of organotin halides continue
to provide fundamental information about both the Lewis
acid–base model and the reactivity of organotin species (2).
Received 3 January 2003. Published on the NRC Research
Press Web site at http://canjchem.nrc.ca on 10 June 2003.
C. Ma,1,2 Q. Jiang, and R. Zhang. Department of
Chemistry, Liaocheng University, Liaocheng 252059, P.R.
China.
1Present address: Department of Chemistry, Taishan
University, Taian 271021, P.R. China.
2Corresponding author (e-mail: macl@lctu.edu.cn).
Can. J. Chem. 81: 825–831 (2003)
doi: 10.1139/V03-087
© 2003 NRC Canada

826
Can. J. Chem. Vol. 81, 2003
Scheme 1.
1
title compound by elemental, IR, H NMR, and X-ray dif-
fraction analyses and give a discussion on its reactive mech-
anism and structure. The procedure is described in
Scheme 1.
X-ray structure determination
All X-ray crystallographic studies were done using a
Bruker Smart 1000 diffractometer fitted with graphite-mono-
chromated Mo Kα radiation (λ = 0.71073 Å). The ω/2θ scan
technique was employed. Corrections were applied for Lo-
rentz and polarization effects but not for absorption, satisfy-
ing I ≥ 2σ(I). Criterion of observability was used for the
solution and refinement. The structure was solved using di-
rect methods and refined by a full-matrix least squares pro-
cedure based on F2, using the SHELXL-97 program system.
All non-H atoms were included in the model at their calcu-
lated positions. All data were collected at a temperature of
298(2) K. For complex 1 and compound 3, the crystal struc-
tures and unit cells are shown in Figs. 1–4, respectively. Se-
lected bond distances and angles are listed in Table 1.
Crystal data for compound 3: formula C28H21ClN4O5S3Sn,
M = 743.81, monoclinic, space group P21/c, a = 15.041(6),
b = 16.647(6), c = 12.742(5), β = 109.973(6)°, V =
2999(2) Å3, Z = 4, Dcalcd = 1.648 g cm–3, µ = 1.195 mm–1,
F(000) = 1488, GoF = 0.886, 16 278 reflections collected
(θ = 1.44° to 26.47°), 5821 of which were used in the refine-
ment to give the final R1 = 0.0658 and wR2 = 0.1238. Resid-
ual electron density: 0.567 and –0.883 e Å–3.
Crystal data for complex 1: formula C19H13ClN2O2S2Sn,
M = 519.57, triclinic, space group P1, a = 12.961(6), b =
13.835(7), c = 16.412(8) Å, α = 69.184(8)°, β = 89.862(9)°,
γ = 62.579(8)°, V = 2395(2) Å3, Z = 4, Dcalcd = 1.441 g cm–3,
µ = 1.367 mm–1, F(000) = 1024. GoF = 0.748, 13 476
reflections collected (θ = 1.80° to 26.63°), 9316 of which
were used in the refinement to give the final R1 = 0.0591
and wR2 = 0.0828. Residual electron density: 0.605 and
–0.642 e Å–3.
Experimental
Materials and measurements
Diphenyltin dichloride and 2-mercapto-6-nitrobenzothia-
zole were commercially available, and they were used with-
out further purification. The melting points were obtained
with Kofler micro melting point apparatus and are uncor-
rected. Infrared spectra were recorded on a Nicolet-460
spectrophotometer using KBr discs and sodium chloride op-
1
tics. H NMR spectra were obtained on a JEOL-FX-90Q
NMR spectrometer; chemical shifts were given in ppm rela-
tive to Me4Si in CDCl3 solvent. Elemental analyses were
performed with a PE-2400II apparatus.
Synthesis
The reaction was carried out under nitrogen atmosphere.
The 2-mercapto-6-nitrobenzothiazole (0.212 g, 1.0 mmol)
and sodium ethoxide (0.102 g, 1.5 mmol) were added to a
solution of benzene (20 mL) in a Schlenk flask and stirred
for 0.5 h. After the diphenyltin dichloride (0.343 g,
1.0 mmol) was added to the reactor, the reaction mixture
was stirred for 12 h at 40°C and then filtrated. The filtrate
was gradually removed by vaporization under vacuum until
solid product was obtained. The solid was then recrystallized
from ether–dichloromethane. There were two colored crystal
compounds formed. One is yellow while the other is orange.
Total yield: 0.462 g.
The compound 3 (orange crystal): mp 88–90°C. IR
(KBr)(cm–1): υas(Sn-C), 275; υs(Sn-C), 229; υ(Sn-Cl), 260;
υ(Sn-S), 290; υ(Sn-N), 453; υ(C-S), 746; υ(C=N), 1637,
Results and discussion
1
1598; υs(C-O) 1065. H NMR (CDCl3, ppm): 6.81–7.86 (m,
Syntheses aspects
16H), 2.50–2.62 (q, 2h), 0.90–1.10 (t, 3H). Anal. calcd. for
C28H21ClN4O5S3Sn: C 45.20, H 2.85, N 7.53, S 12.91;
found: C 45.51, H 2.93, N 7.44, S 12.87.
It was surprising that we obtained an infinite one-
dimensional linked compound 3 assembled by aromatic
benzothiazole–benzothiazole π-π stacking interactions. To
investigate the synthetical mechanism of the reaction, we
carried out a series of further experiments (with the same ap-
proach as that for compound 3), as shown in Table 2.
According to experiments (a), (b), and (c), we can con-
clude that the possible synthetical mechanism of 3 is a three-
step process, as follows: First, the 2-mercapto-6-nitrobenzo-
The complex 1 (yellow crystal): mp 149–151°C. IR
(KBr): υs(Sn-C), 278; υs(Sn-C), 232; υ(Sn-Cl), 266; υ(Sn-S),
1
290; υ(Sn-N), 448; υ(C-S), 748; υ(C=N), 1599. H NMR
(CDCl3, ppm): 7.46–7.79 (m, 13H). Anal. calcd. for
C19H13ClN2O2S2Sn: C 43.91, H 2.52, N 5.39, S 12.32;
found: C 43.86, H 2.52, N 5.29, S 12.31.
© 2003 NRC Canada

Ma et al.
827
Fig. 1. Molecular structure of the compound 3.
Fig. 2. Molecular structure of the complex 1.
© 2003 NRC Canada

828
Can. J. Chem. Vol. 81, 2003
Fig. 3. Unit cell of the compound 3.
Fig. 4. Unit cell of the complex 1.
thiazole (B) reacts with sodium ethoxide (C) to form its
sodium salt, which then reacts with the diphenyltin
dichloride to form 1. Second, 1 continues to react with ex-
cess C to form 2. Finally, through the benzothiazole–
benzothiazole π-π stacking interaction, 1 and 2 constitute the
linked compound 3.
The formation of substitutional product 2 is owed to the
existence of 1 and excess C. Because of the interaction of
© 2003 NRC Canada

Ma et al.
829
Table 1. Selected bond distances (Å) and angles (°) for com-
pound 3 and complex 1.
replaced in Ph2SnCl2; see experiment (d). The result sug-
gested that the spatial resistance from two phenyl groups is
strong enough to prevent another ligand chelating to the cen-
tral tin atom. The conclusion coincides well with the case of
Ph2SnCl(MBT) reported in the literature (12).
Compound (3)
Complex (1)
Bond distances (Å)
Sn(1)—C(14)
Sn(1)—C(8)
Sn(1)—Cl(1)
Sn(1)—S(2)
Sn(1)—N(1)
S(2)—C(1)
2.103(13)
2.110(11)
2.384(3)
2.448(3)
2.582(7)
1.672(9)
1.302(10)
1.800(9)
1.715(11)
1.335(12)
1.502(13)
1.298(12)
1.319(13)
1.732(13)
1.756(10)
1.401(10)
3.45
Sn(1)—C(14)
Sn(1)—C(8)
Sn(1)—Cl(1)
Sn(1)—S(2)
Sn(1)—N(1)
N(1)—C(1)
S(2)—C(1)
Sn(2)—C(33)
Sn(2)—C(27)
Sn(2)—Cl(2)
Sn(2)—S(4)
Sn(2)—N(3)
N(3)—C(20)
S(4)—C(20)
Cl(2)···S(1)
Cl(2)···S(2)
Cl(2)···S(3)
Cl(2)···S(4)
2.066(10)
2.102(12)
2.367(3)
2.444(2)
2.595(7)
1.316(8)
1.730(8)
2.026(12)
2.084(11)
2.373(2)
2.446(3)
2.580(6)
1.332(10)
1.727(8)
3.415
IR data
The explicit feature in the infrared spectra of the title
compound is the absence of the band in the region 2600–
2550 cm–1, which appears in the free ligand as the υ(S-H)
vibration, thus indicating metal—ligand bond formation
through this site. In the far-infrared spectra, strong absorp-
tion at 290 cm–1 (for both compound 3 and complex 1),
which is absent in the spectrum of the ligand, is assigned to
the Sn-S stretching mode of vibration, and all the values are
consistent with that detected for a number of organotin(IV)–
sulfur derivatives (3). Medium-intensity bands at 275 and
229 cm–1 for compound 3 and 278 and 232 cm–1 for com-
plex 1 can be assigned to υas(Sn-C) and υs(Sn-C). The
υ(C=N) band, occurring at 1599 cm–1 for 1, is shifted con-
siderably towards a lower frequency with respect to that of
the free ligand, confirming the coordination of the hetero-
cyclic N to the tin. The stretching frequency is lowered due
to the displacement of electron density from the N to the Sn
atom, thus resulting in the weakening of the C=N bond, as
reported in the literature (13). Therefore, the weak- or me-
dium-intensity band at 448 cm–1 (for complex 1) can be as-
signed to Sn-N stretching vibrations, while in the title
compound 3, there occur two bands that can be attributed to
the υ(C=N). The band at 1598 cm–1 is similar to the υ(C=N)
band of complex 1, and the band at about 1637 cm–1 is near
to the υ(C=N) value of the free ligand. Together with the
band at 1065 cm–1, recognized as υs(C-O), these messages
provide evidence for the existence of the molecule
(C7H3N2O2S)OEt.
N(1)—C(1)
S(1)—C(1)
S(3)—C(22)
N(3)—C(21)
O(5)—C(27)
O(5)—C(20)
N(3)—C(20)
S(3)—C(20)
S(1)—C(3)
N(1)—C(2)
Cl(2)···S(1)
Cl(2)···S(2)
3.511
3.44
3.57
3.48
Bond angles (°)
C(14)-Sn(1)-C(8)
S(2)-Sn(1)-N(1)
124.6(4)
63.02(17) S(2)-Sn(1)-N(1)
C(14)-Sn(1)-C(8)
123.6(4)
62.90(16)
C(14)-Sn(1)-Cl(1) 101.4(3)
C(14)-Sn(1)-Cl(1) 101.4(3)
C(8)-Sn(1)- N(1)
C(14)-Sn(1)-N(1)
Cl(1)-Sn(1)-N(1)
C(14)-Sn(1)-S(2)
Cl(1)-Sn(1)-S(2)
C(8)-Sn(1)-S(2)
N(1)-C(1)-S(2)
C(8)-Sn(1)-Cl(1)
C(1)-N(1)-Sn(1)
C(1)-S(2)-Sn(1)
O(5)-C(20)-S(3)
O(5)-C(20)-N(3)
N(3)-C(20)-S(3)
90.0(3)
90.5(3)
C(8)-Sn(1)-N(1)
C(14)-Sn(1)-N(1)
90.0(3)
90.5(3)
153.97(18) Cl(1)-Sn(1)-N(1)
115.0(3) C(14)-Sn(1)-S(2)
90.95(10) Cl(1)-Sn(1)-S(2)
114.2(2)
124.0(7)
101.7(3)
87.8(5)
153.96(16)
116.1(2)
91.08(9)
113.9(3)
100.6(3)
C(8)-Sn(1)-S(2)
C(8)-Sn(1)-Cl(1)
C(33)-Sn(2)-C(27) 123.5(4)
S(4)-Sn(2)-N(3)
C(33)-Sn(2)-Cl(2) 102.2(3)
C(27)-Sn(2)-N(3)
C(33)-Sn(2)-N(3)
Cl(2)-Sn(2)-N(3)
C(33)-Sn(2)-S(4)
Cl(2)-Sn(2)-S(4)
C(27)-Sn(2)-S(4)
63.06(17)
1H NMR data
85.2(3)
1H NMR data showed that the signal of the -SH proton,
present in the spectrum of the ligand, is absent in the title
compound 3 and the complex 1, indicating the removal of
the SH proton and the formation of Sn—S bonds. The infor-
mation accords well with what the IR data revealed. As an-
ticipated, the spectrum consists of the phenyl hydrogen
resonance at 7.32–7.86 ppm for complex 1 and the phenyl
hydrogen resonance at 6.81–7.86 ppm for the mixture of 1
and 2 in compound 3. In addition, there is a resonance due
to the ethoxyl hydrogen in compound 3 at 2.50–2.62 ppm (q,
2h) and 0.90–1.10 ppm (t, 3H), which also proves the pres-
ence of the molecule (C7H3N2O2S)OEt 2.
118.6(9)
125.2(11)
116.2(8)
91.2(3)
88.3(3)
154.78(18)
113.1(3)
91.72(10)
116.6(2)
C(20)-N(3)-C(21) 110.6(9)
C(22)-S(3)-C(20) 88.3(6)
C(20)-O(5)-C(27) 115.6(10)
the S-Sn, the sulfur—carbon (Sn-S-C) bond strength in 1 be-
comes weaker and the carbon atom [C=N(S)(S)] becomes
more electropositive than those of B, respectively, which
makes the carbon—sulfur bond much easier to cleave. So,
the group EtO- can substitute for the -S-SnPh2(Cl) group
and form 2. Here, Ph2SnCl2 functions as a Lewis-acid cata-
lyst in the replacement reaction. This point of view is well
support by the results of experiments (a), (b), and (c). There
were several mechanisms of carbon—sulfur bond cleavage
put forward before (11), but the conditions of all those reac-
tions were rigid, catalysts were needed, and the reaction was
often accompanied with oxidation. Our results may provide
a new way to these kinds of reactions.
Molecular structures
For compound 3, single crystal X-ray diffraction data re-
veal that it has two different molecular components. The
component Ph2Sn(Cl)[S(C7H3N2O2S)] has a pentacoordin-
ated tin. The four primary bonds to the centered tin atom are
two to the phenyl groups and one each to sulfur and chloride
atoms. In addition, there exists interaction between tin and
nitrogen atoms. The Sn(1)—N(1) bond length (2.582(7) Å)
coincides with those of the type “SnCl2N2C2” recorded in
the Cambridge Crystallographic Database (14), ranging from
It is worthy to note that despite using a 1:2:2 molar ratio
of A:B:C, we didn’t obtain the product with two chlorides
© 2003 NRC Canada

830
Can. J. Chem. Vol. 81, 2003
Table 2. A series of further experiments.
A (mmol)
B (mmol)
C (mmol)
Solution
Temperature (°C)
Products
a
b
c
d
1.0
1.0
0.0
1.0
1.0
1.0
1.0
2.0
1.5
1.0
1.0
2.0
Benzene (20 ml)
Benzene (20 ml)
Benzene (20 ml)
Benzene (20 ml)
40
40
40
40
Complex 1 and compound 3
Complex 1
Complex 2
Complex 1
2.27 to 2.58 Å; equal to that of [2-(Me2NCH2)C6H4]SnPh2Cl
(2.52 Å) (15); and longer than that of Ph2SnCl(MBT)
(2.41 Å) (12), but much shorter than the sum of the van der
Waals radii of Sn and N, 3.74 Å (16), thus providing a 4-
membered chelate ring with a bite angle, N(1)-Sn(1)-S(2), of
63.02(17)°. If the tin–nitrogen interaction is included, the
geometry at Sn then becomes a distorted cis-trigonal
bipyramidal with Cl(1) and N(1) in axial sites (Cl(1)-Sn(1)-
N(1) = 153.97(18)°) and C(8), C(14), and S(2) occupying
the equatorial plane (C(14)-Sn(1)-C(8) = 124.6(4)°). The
sum of the angles subtended at the tin atom in the trigonal
plane is 358.3°, so the tin atom shows no significant devia-
tion from the equatorial plane. The Sn(1)—Cl(1) bond
length (2.384(3) Å) lies in the range of the covalent radii
(2.37–2.60 Å) (15). The Sn(1)—S(2) bond length
(2.448(3) Å) is well within the range — from 2.41 to 2.48 Å —
that is reported for triphenyltin heteroarenethiolates (3),
slightly shorter than that of Ph2SnCl(MBT) (2.49 Å) (12),
and almost equal to that of Ar3Sn[S(C5H4N)] (17). Finally,
the Sn—C bond lengths are approximately equal (Sn(1)—
C(8) = 2.110(11) and Sn(1)—C(14) = 2.103(13) Å) and are
similar to the average value, 2.13 Å (14).
Besides, in the represented crystalline structure, a rela-
tively close contact between the Cl atom of Ph2Sn(Cl)-
[S(C7H3N2O2S)] and the two S atoms of its adjacent mole-
cule (Cl(2)···S(1), 3.45 Å and Cl(2)···S(2), 3.45 Å) was rec-
ognized, which coincided well with that reported in
(PhCH2)2SnClS2CNC4H8O (3.49 Å) (18) but was much
shorter than the sum of the van der Waals radii (3.97 Å) for
these atoms (19). And it is the intermolecular, non-bonded
Cl···S interaction that favored the regular self-assembly of
Ph2Sn(Cl)[S(C7H3N2O2S)] and further made it an infinite 1D
chain. Intermolecular, non-bonded S···X (X = O, S, N, etc.)
interactions have been investigated for characterization of
the molecular structures of a large number of organosulfur
compounds (20). But we have seen few discussions about
the Cl···S interaction up to now. So, we can regard it as an-
other new type of close contact.
proaches that of imidazole–imidazole (3.29 Å) (6). It implies
that there exists a strong face-to-face π-π stacking interac-
tion between the two benzothiazole–benzothiazole ring
planes. In virtue of the significant interlayer interaction, the
gaps between netlike layers of Ph2Sn(Cl)[S(C7H3N2O2S)]
are filled by the molecule [C7H3N2O2S]OEt. The molar ratio
of (C7H3N2O2S)OEt:Ph2Sn(Cl)[S(C7H3N2O2S)] is 1:1, so
that the molecular formula can be written in brief as
Ph2Sn(Cl)-[S(C7H3N2O2S)]·[(C7H3N2O2S)OEt].
For the complex 1, as far as bond lengths, bond angles,
and intermolecular Cl···S non-bonded interactions are con-
cerned, its structure is very similar to that of the title com-
pound 3, and it is a one-dimensional chain, too. However,
there exits no molecule in its crystal grids and no
intermolecular π-π stacking interaction. The Cl···S distance
ranges from 3.42 Å to 3.57 Å. For detailed data see Table 1.
Acknowledgments
We thank the National Natural Foundation, P.R. China
(20271025), the Key Teachers Foundation from the State
Education Ministry of China, and the National Natural
Foundation of Shandong Province, P.R. China for financial
support of this work.
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Quite unexpectedly, the two different molecular compo-
nents Ph2Sn(Cl)[S(C7H3N2O2S)] and (C7H3N2O2S)OEt are
accommodated in parallel layers. The layers of Ph2Sn(Cl)-
[S(C7H3N2O2S)] result in an intercalation lattice that holds
(C7H3N2O2S)OEt molecules. All those atoms on the
benzothiazole ring in Ph2Sn(Cl)[S(C7H3N2O2S)] are in the
same plane, with only a negligible tilt (dihedral angle be-
tween the phenyl ring (C(2)–C(7)) and the heterocyclic ring
(C(1)–C(3),N(1),S(1)), 0.6°), while two benzothiazole–
benzothiazole ring planes, C(1)–C(7) in Ph2Sn(Cl)[S(C7H3N2O2S)]
and C(20)–C(26) in (C7H3N2O2S)OEt, are almost parallel to
each other, and the dihedral angle is 4.1°.The shortest dis-
tance of C(25) to C(1)–C(7) is 3.30 Å and the average dis-
tance is 3.42 Å, which is terribly consistent with that of a
benzene polymer in theoretical studies (3.4 Å) (21) and ap-
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