organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Tables 1 and 3). The substituents are essentially coplanar with
their respective rings, giving molecules in which all the atoms
lie in two planes. The dihedral angle between the planes of the
two phenyl rings in the orthorhombic form is 83.34 (9)ꢀ, while
an average value of 84.90 (2)ꢀ is observed for the triclinic
form. The values of the S11ÐS21ÐC21ÐC22, S11ÐS21Ð
C21ÐC26, S21ÐS11ÐC11ÐC12 and S21ÐS11ÐC11ÐC16
torsion angles in the orthorhombic form [ 174.69 (14),
ISSN 0108-2701
Two polymorphs of bis(2-bromo-
phenyl) disulfide
7.46 (19),
172.68 (14) and 8.33 (18)ꢀ, respectively] are
slightly different from the corresponding mean angles in the
triclinic system [ 169.9 (2), 11.1 (2), 169.2 (2) and 13.5 (2)ꢀ,
respectively]. The orthorhombic form crystallizes with one
a
a
b
Â
J. R. Anacona, * Jofre Gomez and Daniel Lorono
Ä
a
Â
Â
Departamento de Quõmica, Universidad de Oriente, Apartado Postal 208, Cumana,
Venezuela, and bSchool of Chemistry, University of Edinburgh, West Mains Road,
Edinburgh EH9 3JJ, Scotland
Correspondence e-mail: juananacona@hotmail.com
Received 13 January 2003
Accepted 25 March 2003
Online 30 April 2003
Colourless crystals of the title compound, bis(2-bromophenyl)
disul®de, C12H8Br2S2, are obtained from the reaction of
2-bromophenylmercaptan with metallic sodium and either
zinc chloride or cadmium chloride in methanol. In the
presence of ZnII ions, the crystals are orthorhombic (space
group Pbca, with Z0 = 1); with CdII ions present, the product is
triclinic (space group P1, with Z0 = 4). Both polymorphs
exhibit signi®cant intramolecular CÐHÁ Á ÁS hydrogen bonds.
In the orthorhombic form, molecules are linked by inter-
molecular CÐHÁ Á ÁBr hydrogen bonds, while in the triclinic
form, molecules exhibit BrÁ Á ÁBr contacts.
Figure 1
The asymmetric unit of the orthorhombic form (Z0 = 1), (I). Displace-
ment ellipsoids are shown at the 50% probability level.
Comment
The electronic and structural properties of transition and main
group metal complexes coordinated by S-donor atoms have
attracted intense research interest over the past 30 years
(Kasper & Interrante, 1976; Kobayashi et al., 1982; Pullen et
al., 1998; Kie-Moon & Holm, 2001). Although some studies
have appeared describing the behaviour of the disul®de group
as a donor (Valde et al., 1983; Matsubayashi & Yokozawa,
1990; Oshio, 1993; Kobayashi et al., 1990), it has not been
subjected to such detailed study as a number of other donor
groups (Balch et al., 1968; Gray, 1966; Schrauzer & Mayweg,
1966). This neglect is in part because the disul®de group tends
to give bridged or polymeric metal complexes, which are
extremely insoluble and are accordingly dif®cult to char-
acterize or study. We report here the structures of two poly-
morphs of bis(2-bromophenyl) disul®de, isolated during
attempts to synthesize zinc(II) or cadmium(II) complexes of
the ligand. There are no signi®cant differences in the bond
lengths observed for the two polymorphs (Figs. 1 and 2, and
Figure 2
Views of (a) the molecule and (b) the unit-cell packing of the triclinic
form (Z0 = 4), (II). Displacement ellipsoids are shown at the 50%
probability level.
Acta Cryst. (2003). C59, o277±o280
DOI: 10.1107/S0108270103006851
# 2003 International Union of Crystallography o277