organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
disul®de compounds with the 1-phenyl-1H-tetrazole fragment.
The 5-nitropyridine fragment of (I) shows excellent agreement
with the bonding geometries of previously reported structures
(Brito, Mundaca et al., 2007). The nitro group is rotated by
about 12.3 (4)ꢀ out the plane of the pyridine ring. In the
strongly electronegative 1-phenyltetrazole system, the tetra-
zole ring is planar, with a mean deviation from the least-
ISSN 0108-2701
5-(5-Nitropyridin-2-yldithio)-
1-phenyl-1H-tetrazole
Ê
squares plane of 0.0036 (17) A. The dihedral angle between
the least-squares planes of the tetrazole and benzene rings is
55.17 (11)ꢀ. The tetrazole ring geometry is normal and in
agreement with the average values found in 69 entries with the
S substituent at C5 for 1,5-disubstituted tetrazoles with alkyl
or aryl substituents found in a search of the CSD, as are all
other geometric parameters, which fall within the expected
ranges.
The gross structure adopted by compound (I) is essentially
the same as those reported previously for the precursor
products, namely 5,50-dinitro-2,20-dithiodipyridine (Brito,
Mundaca et al., 2007) and 5,50-dithiobis(1-phenyl-1H-tetra-
a
a
b
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Ivan Brito, * Aldo Mundaca, Alejandro Cardenas and
c
Â
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Matõas Lopez-Rodrõguez
a
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Departamento de Quõmica, Facultad de Ciencias Basicas, Universidad de
b
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Antofagasta, Casilla 170, Antofagasta, Chile, Departamento de Fõsica, Facultad de
Â
Ciencias Basicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and
c
Â
Â
Â
Instituto de Bio-Organica `Antonio Gonzalez', Universidad de La Laguna, Astrofõsico
Â
Francisco Sanchez No. 2, La Laguna, Tenerife, Spain.
Correspondence e-mail: ivanbritob@yahoo.com
Received 27 July 2007
Â
zole) (Brito, Cardenas et al., 2007). The larger observed
Accepted 22 August 2007
Online 22 September 2007
differences between (I) and 5,50-dinitro-2,20-dithiodipyridine
are only in the NÐCÐS and CÐCÐS angles [109.64 (18) and
125.8 (2)ꢀ, and 120.02 (2) and 116.0 (2)ꢀ, respectively]. A
database survey of CÐSÐSÐC fragments (Allen et al., 1987)
found that SÐS bond distances are bimodally distributed: for
torsion angles in the ranges 75±105 and 0±20ꢀ, the mean SÐS
In the title disul®de, C12H8N6O2S2, all bond lengths and angles
are within normal ranges, and the molecules are linked into
centrosymmetric R22(20) dimers by simple CÐHÁ Á ÁN inter-
actions. Weak intermolecular CÐHÁ Á Áꢀ(arene) and ꢀ±ꢀ
interactions, involving the benzene CH groups and the
benzene rings, and the pyridine rings, respectively, further
stabilize and reinforce the crystal structure.
Ê
bond distances are 2.031 (15) and 2.070 (22) A, respectively.
The corresponding value in the title compound is
Ê
2.0427 (10) A, placing it in the lower quartile for Allen's ®rst
Ê
set. The N1ÐC1 bond length is 1.441 (3) A, which is almost
the same as a normal NÐC(phenyl) single bond. These facts
indicate that conjugation effects between the benzene and
tetrazole rings in (I) are negligible (Lyakhov et al., 2006). The
Comment
This paper forms part of our continuing study of the synthesis
and structural characterization of divalent sulfur compounds
(Brito et al., 2006, and references therein). We are particularly
interested in the synthesis of unsymmetrical disul®des as
¯exible ligands, and in their binding modes for the fabrication
of different coordination polymer topologies.
Ê
CÐS bond lengths differ by 0.019 A and this, coupled with the
apparent lack of SÐS double-bond character, shows that there
is probably no communication between the two ring systems
via the disul®de bridge, despite having a ꢀ donor at one end
and a ꢀ acceptor at the other. Using a bond length±bond order
È
relationship (Pauling, 1960; Burgi & Dunitz, 1987), it can be
shown that the CÐS bonds in compound (I) have partial
Ê
Ê
double-bond character of 12 (1.78 A) and 20% (1.76 A),
The molecular structure of the title compound, (I), is shown
in Fig. 1 and selected geometric parameters are given in
Table 1. Yellow crystals of (I) were obtained from the
rhodium(I) complex-catalyzed reaction of 5,50-dinitro-2,20-
dithiodipyridine with 5,5-dithiobis(1-phenyl-1H-tetrazole).
The molecule consists of a 5-nitropyridine ring and a 1-phenyl-
1H-tetrazole ring linked by a bridging disul®de group.
Figure 1
A view of (I), showing the atom-numbering scheme. Displacement
ellipsoids are drawn at the 50% probability level and H atoms are shown
as small spheres of arbitrary radii. The intramolecular hydrogen bond is
indicated by a double-dashed line.
A search of the Cambridge Structural Database (CSD,
Version 5.28 of May 2007; Allen, 2002) did not ®nd any
o606 # 2007 International Union of Crystallography
DOI: 10.1107/S010827010704142X
Acta Cryst. (2007). C63, o606±o608