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Volume 70 
Part 5 
Page o529  
May 2014  

Received 24 March 2014
Accepted 2 April 2014
Online 9 April 2014

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 19.2
Details
Open access

Bis(2,3-di­chloro­phen­yl) di­sulfide

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, Mexico, and bUniversidad Politécnica de Tlaxcala, Av. Universidad Politécnica de Tlaxcala No. 1, San Pedro Xalcaltzinco Municipio de Tepeyanco, Tlaxcala, C.P. 90180, Mexico
Correspondence e-mail: ericka.santacruz@uptlax.edu.mx

The title compound, C12H6Cl4S2, features an S-S bond [2.0252 (8) Å] that bridges two 2,3-di­chloro­phenyl rings with a C-S-S-C torsion angle of 88.35 (11)°. The benzene rings are normal one to the other with a dihedral angle of 89.83 (11)°. The crystal structure features inter­molecular Cl...Cl [3.4763 (11) Å] and [pi]-[pi] stacking inter­actions [centroid-centroid distances = 3.696 (1) and 3.641 (2) Å]. Intra­molecular C-H...S inter­actions are also observed.

Related literature

For applications of di­sulfide compounds, see: Crowley (1964[Crowley, D. J. (1964). US Patent No. 3 150 186.]); Hashash et al. (2002[Hashash, A., Kirkpatrick, D. L., Lazo, J. S. & Block, L. H. (2002). J. Pharm. Sci. 91, 1686-1692.]); Gomez-Benitez et al. (2006[Gomez-Benitez, V., Baldovino-Pantaleon, O., Herrera-Alvarez, C., Toscano, R. A. & Morales-Morales, D. (2006). Tetrahedron Lett. 47, 5059-5062.]); Yu et al. (2010[Yu, C., Jin, B., Liu, Z. & Zhong, W. (2010). Can. J. Chem. 88, 485-491.]). For various methods of synthesizing disulfides, see: Xiao et al. (2009[Xiao, H., Chen, J., Liu, M., Wu, H. & Ding, J. (2009). Phosphorus Sulfur Silicon Relat. Elem. 184, 2553-2559.]); Shaabani et al. (2008[Shaabani, A., Safari, N., Shoghpour, S. & Hossein, A. R. (2008). Monatsh. Chem. 139, 613-615.]); Ogilby (2010[Ogilby, P. R. (2010). Chem. Soc. Rev. 39, 3181-3209.]). For similar compounds and their crystal structures, see: Deng et al. (2003[Deng, S.-L., Long, L.-S., Xie, S.-Y., Huang, R.-B., Zheng, L.-S. & Ng, S. W. (2003). Acta Cryst. E59, o843-o844.]); Korp & Bernal (1984[Korp, J. D. & Bernal, I. (1984). J. Mol. Struct. 118, 157-164.]); Tang et al. (2011[Tang, J.-M., Feng, Z.-Q. & Cheng, W. (2011). Acta Cryst. E67, o1197.]). For di­sulfide bonds in proteins, see: Sevier & Kaiser (2006[Sevier, C. S. & Kaiser, C. A. (2006). Antioxid. Redox Signal. 8, 797-811.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data
  • C12H6Cl4S2

  • Mr = 356.09

  • Triclinic, [P \overline 1]

  • a = 7.7149 (10) Å

  • b = 7.7326 (11) Å

  • c = 12.748 (2) Å

  • [alpha] = 91.472 (2)°

  • [beta] = 91.233 (3)°

  • [gamma] = 114.859 (2)°

  • V = 689.37 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.14 mm-1

  • T = 298 K

  • 0.37 × 0.24 × 0.14 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.678, Tmax = 0.862

  • 7044 measured reflections

  • 3130 independent reflections

  • 2594 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.03

  • 3130 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...S2 0.93 2.70 3.202 (2) 115
C12-H12...S1 0.93 2.70 3.199 (2) 115

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: BX2456 ).


Acknowledgements

This work was supported by CONACYT (grant No. CB2010-154732) and PAPIIT (grants IN201711-3 and IN213214-3). ESJ thanks PROMEP "Apoyo a perfil deseable". RRM and DMM thank Dr Ruben A. Toscano for technical assistance.

References

Bondi, A. (1964). J. Phys. Chem. 68, 441-451.  [CrossRef] [ChemPort] [Web of Science]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crowley, D. J. (1964). US Patent No. 3 150 186.
Deng, S.-L., Long, L.-S., Xie, S.-Y., Huang, R.-B., Zheng, L.-S. & Ng, S. W. (2003). Acta Cryst. E59, o843-o844.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gomez-Benitez, V., Baldovino-Pantaleon, O., Herrera-Alvarez, C., Toscano, R. A. & Morales-Morales, D. (2006). Tetrahedron Lett. 47, 5059-5062.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Hashash, A., Kirkpatrick, D. L., Lazo, J. S. & Block, L. H. (2002). J. Pharm. Sci. 91, 1686-1692.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Korp, J. D. & Bernal, I. (1984). J. Mol. Struct. 118, 157-164.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Ogilby, P. R. (2010). Chem. Soc. Rev. 39, 3181-3209.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sevier, C. S. & Kaiser, C. A. (2006). Antioxid. Redox Signal. 8, 797-811.  [CrossRef] [PubMed] [ChemPort]
Shaabani, A., Safari, N., Shoghpour, S. & Hossein, A. R. (2008). Monatsh. Chem. 139, 613-615.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tang, J.-M., Feng, Z.-Q. & Cheng, W. (2011). Acta Cryst. E67, o1197.  [CSD] [CrossRef] [IUCr Journals]
Xiao, H., Chen, J., Liu, M., Wu, H. & Ding, J. (2009). Phosphorus Sulfur Silicon Relat. Elem. 184, 2553-2559.  [CrossRef] [ChemPort]
Yu, C., Jin, B., Liu, Z. & Zhong, W. (2010). Can. J. Chem. 88, 485-491.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o529  [ doi:10.1107/S1600536814007326 ]

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