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Volume 69 
Part 7 
Pages o1078-o1079  
July 2013  

Received 5 June 2013
Accepted 5 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.008 Å
R = 0.063
wR = 0.134
Data-to-parameter ratio = 18.4
Details
Open access

2,2'-(Disulfanediyl)dianilinium dichloride dihydrate

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000, Algeria, and bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title hydrated molecular salt, C12H14N2S22+·2Cl-·2H2O, the dihedral angle between the benzene rings in the dication is 9.03 (17)° and the C-S-S-C torsion angle is 96.8 (2)°. The crystal packing can be described as alternating organic and anionic water layers lying parallel to (100), which are linked by N-H...Cl and N-H...O hydrogen bonds. O-H...Cl hydrogen bonds and aromatic [pi]-[pi] stacking interactions [centroid-centroid separation = 3.730 (3) Å] are also observed.

Related literature

For related structures and background to disulfides, see: Benmebarek et al. (2012[Benmebarek, S., Boudraa, M., Bouacida, S. & Daran, J.-C. (2012). Acta Cryst. E68, o3207.], 2013[Benmebarek, S., Boudraa, M., Bouacida, S. & Merazig, H. (2013). Acta Cryst. E69, o432.]). For related structures, see: Tang et al. (2011[Tang, J.-M., Feng, Z.-Q. & Cheng, W. (2011). Acta Cryst. E67, o1197.]); Goh et al. (2010[Goh, J. H., Fun, H.-K., Babu, M. & Kalluraya, B. (2010). Acta Cryst. E66, o292-o293.]); Song & Fan (2009[Song, M. & Fan, C. (2009). Acta Cryst. E65, o2835.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N2S22+·2Cl-·2H2O

  • Mr = 357.32

  • Orthorhombic, P n a 21

  • a = 17.826 (7) Å

  • b = 13.358 (5) Å

  • c = 7.120 (3) Å

  • V = 1695.4 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.63 mm-1

  • T = 150 K

  • 0.16 × 0.13 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 10760 measured reflections

  • 3584 independent reflections

  • 2409 reflections with I > 2[sigma](I)

  • Rint = 0.097

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.134

  • S = 1.05

  • 3584 reflections

  • 195 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1369 Friedel pairs

  • Flack parameter: -0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1Wi 0.89 1.83 2.723 (6) 178
N1-H1B...Cl2i 0.89 2.24 3.108 (4) 166
N1-H1C...Cl1i 0.89 2.25 3.103 (4) 160
N2-H2A...O2Wii 0.89 1.84 2.727 (6) 177
N2-H2B...Cl2iii 0.89 2.26 3.111 (4) 160
N2-H2C...Cl2 0.89 2.30 3.157 (4) 163
O2W-H4W...Cl2 0.86 (5) 2.36 (5) 3.157 (5) 155 (5)
O2W-H3W...Cl1iv 0.85 (5) 2.23 (5) 3.078 (4) 171 (6)
O1W-H1W...Cl1v 0.85 (5) 2.27 (5) 3.096 (5) 167 (5)
O1W-H2W...Cl1iv 0.86 (5) 2.27 (5) 3.127 (5) 176 (7)
Symmetry codes: (i) [-x+2, -y, z+{\script{1\over 2}}]; (ii) x, y, z-1; (iii) [-x+2, -y, z-{\script{1\over 2}}]; (iv) x, y, z+1; (v) [-x+2, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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 & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7089 ).


Acknowledgements

This work is supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université de Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie - Algérie) via the PNR programme for financial support.

References

Benmebarek, S., Boudraa, M., Bouacida, S. & Daran, J.-C. (2012). Acta Cryst. E68, o3207.  [CSD] [CrossRef] [IUCr Journals]
Benmebarek, S., Boudraa, M., Bouacida, S. & Merazig, H. (2013). Acta Cryst. E69, o432.  [CrossRef] [IUCr Journals]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Goh, J. H., Fun, H.-K., Babu, M. & Kalluraya, B. (2010). Acta Cryst. E66, o292-o293.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Song, M. & Fan, C. (2009). Acta Cryst. E65, o2835.  [CSD] [CrossRef] [IUCr Journals]
Tang, J.-M., Feng, Z.-Q. & Cheng, W. (2011). Acta Cryst. E67, o1197.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1078-o1079   [ doi:10.1107/S1600536813015742 ]

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