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Volume 69 
Part 12 
Pages o1753-o1754  
December 2013  

Received 2 November 2013
Accepted 2 November 2013
Online 9 November 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.074
wR = 0.254
Data-to-parameter ratio = 9.8
Details
Open access

Bis{4-[(E)-2-(1H-indol-3-yl)ethen­yl]-1-methyl­pyridinium} 4-chloro­benzene­sulfonate nitrate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title mixed salt, 2C16H15N2+·C6H4ClO3S-·NO3-, one of the cations shows whole mol­ecule disorder over two sets of sites in a 0.711 (7):0.289 (7) ratio. The 4-chorobenzenesulfon­ate anion is also disordered over two orientations in a 0.503 (6):0.497 (6) ratio. The cations are close to planar, the dihedral angles between the pyridinium and indole rings being 1.48 (3)° in the ordered cation, and 5.62 (3) and 2.45 (3)°, respectively, for the major and minor components of the disordered cation. In the crystal, the cations are stacked in an anti­parallel manner approximately along the a-axis direction and linked with the anions via N-H...O hydrogen bonds and C-H...O inter­actions, generating a three-dimensional network. Weak C-H...[pi] and [pi]-[pi] inter­actions [with centroid-centroid distances of 3.561 (2)-3.969 (7) Å] are also observed.

Related literature

For related structures, see: Chantrapromma et al. (2008[Chantrapromma, S., Kobkeatthawin, T., Chanawanno, K., Karalai, C. & Fun, H.-K. (2008). Acta Cryst. E64, o876-o877.]); Chantrapromma & Fun (2009[Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o258-o259.]). For background to non-linear optical materials, see: Dittrich et al. (2003[Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.]); Nogi et al. (2000[Nogi, K., Anwar, U., Tsuji, K., Duan, X.-M., Okada, S., Oikawa, H., Matsuda, H. & Nakanishi, H. (2000). Nonlinear Optics, 24, 35-40.]); Raimundo et al. (2002[Raimundo, J.-M., Blanchard, P., Planas, N. G., Mercier, N., Rak, I. L., Hierle, R. & Roncali, J. (2002). J. Org. Chem. 67, 205-218.]); Ruanwas et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]); Sato et al. (1999[Sato, N., Rikukawa, M., Sanui, K. & Ogata, N. (1999). Synth. Met. 101, 132-133.]).

[Scheme 1]

Experimental

Crystal data
  • 2C16H15N2+·C6H4ClO3S-·NO3-

  • Mr = 724.21

  • Triclinic, [P \overline 1]

  • a = 8.7540 (7) Å

  • b = 13.6648 (10) Å

  • c = 15.3465 (11) Å

  • [alpha] = 97.206 (1)°

  • [beta] = 91.186 (2)°

  • [gamma] = 99.924 (1)°

  • V = 1792.3 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 153 K

  • 0.55 × 0.47 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.970

  • 9106 measured reflections

  • 6217 independent reflections

  • 4480 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.254

  • S = 1.05

  • 6217 reflections

  • 636 parameters

  • 206 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg6, Cg7 and Cg9 are the centroids of the C16-C21, C32-C37, N4A/C30A-C32A/C37A and C32A-C37A rings, respectively.

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O3A 0.78 2.19 2.937 (9) 161
N4-H1N4...O4i 0.81 2.43 3.220 (11) 165
N4-H1N4...O5i 0.81 2.32 2.987 (8) 141
C3A-H3AA...O5ii 0.93 2.43 3.246 (13) 146
C8-H8A...O2Aiii 0.93 2.40 3.213 (8) 146
C10-H10A...O5iv 0.93 2.51 3.234 (6) 134
C18-H18A...O1Av 0.93 2.52 3.345 (8) 148
C22-H22A...O1Aiii 0.96 2.45 3.368 (9) 160
C22-H22C...O2Avi 0.96 2.32 3.082 (9) 136
C26-H26A...O6vii 0.93 2.53 3.440 (7) 168
C15-H15A...Cg6vii 0.93 2.71 3.550 (6) 151
C15-H15A...Cg7vii 0.93 2.94 3.844 (10) 165
C15-H15A...Cg9vii 0.93 2.83 3.656 (13) 149
C34-H34A...Cg3ii 0.93 2.78 3.602 (7) 149
C38-H38C...Cg6ii 0.96 2.95 3.714 (8) 137
C38-H38C...Cg9vii 0.96 2.83 3.627 (14) 141
C34A-H34B...Cg3ii 0.93 2.89 3.56 (2) 130
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y, -z; (iv) -x+1, -y, -z+1; (v) -x+2, -y+1, -z; (vi) x, y-1, z; (vii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7156 ).


Acknowledgements

The authors thank Prince of Songkla University for generous support and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o258-o259.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Chantrapromma, S., Kobkeatthawin, T., Chanawanno, K., Karalai, C. & Fun, H.-K. (2008). Acta Cryst. E64, o876-o877.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.  [Web of Science] [CrossRef] [ChemPort]
Nogi, K., Anwar, U., Tsuji, K., Duan, X.-M., Okada, S., Oikawa, H., Matsuda, H. & Nakanishi, H. (2000). Nonlinear Optics, 24, 35-40.  [ChemPort]
Raimundo, J.-M., Blanchard, P., Planas, N. G., Mercier, N., Rak, I. L., Hierle, R. & Roncali, J. (2002). J. Org. Chem. 67, 205-218.  [CrossRef] [PubMed] [ChemPort]
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sato, N., Rikukawa, M., Sanui, K. & Ogata, N. (1999). Synth. Met. 101, 132-133.  [Web of Science] [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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1753-o1754   [ doi:10.1107/S1600536813030080 ]

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