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Volume 69 
Part 11 
Pages o1623-o1624  
November 2013  

Received 25 September 2013
Accepted 3 October 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 13.0
Details
Open access

1-Methyl-4-[(E)-2-(3-hy­droxy-4-meth­oxy­phen­yl)ethen­yl]pyridinium 4-bromo­benzene­sulfonate monohydrate

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

In the title hydrated salt, C15H16NO2+·C6H4BrO3S-·H2O, the cation exists in an E conformation with respect to the ethenyl bond and is almost planar, with a dihedral angle of 2.62 (12)° between the planes of the pyridinium and benzene rings. The meth­oxy substituent deviates slightly from the plane of its attached benzene ring [Cmeth­yl-O-C-C torsion angle = -11.6 (6)°]. In the crystal, the cations, anion and water mol­ecules are linked together into chains along [010] by O-H...O hydrogen bonds and weak C-H...O inter­actions. There is a short Br...O contact [3.029 (2) Å]. The crystal structure also features C-H...[pi] inter­actions involving the benzene ring of the anion.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For applications of stilbene derivatives, see: Belluti et al. (2010[Belluti, F., Fontana, G., Bo, L. D., Carenini, N., Giommarelli, C. & Zunino, F. (2010). Bioorg. Med. Chem. 18, 3543-3550.]); Chanawanno et al. (2010[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.]); Frombaum et al. (2012[Frombaum, M., Le Clanche, S., Bonnefont-Rousselot, D. & Borderie, D. (2012). Biochimie, 94, 269-276.]); Hussain et al. (2009[Hussain, M., Khan, K. M., Ali, S. I., Parveen, R. & Shim, W. S. (2009). Fibers Polym.. 10, 407-412.]); Jindawong et al. (2005[Jindawong, B., Chantrapromma, S., Fun, H.-K., Yu, X.-L. & Karalai, C. (2005). Acta Cryst. E61, o1340-o1342.]); Li et al. (2013[Li, X., Lu, H., He, D., Luo, C. & Huang, J. (2013). J. Fluoresc. 23, 1039-1044.]); Ruanwas et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]). For related structures, see: Chanawanno et al. (2009[Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o1549-o1550.]); Fun et al. (2011[Fun, H. K., Chantrapromma, S. & Jansrisewangwong, P. (2011). Acta Cryst. E67, o105-o106.]); Jindawong et al. (2005[Jindawong, B., Chantrapromma, S., Fun, H.-K., Yu, X.-L. & Karalai, C. (2005). Acta Cryst. E61, o1340-o1342.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16NO2+·C6H4BrO3S-·H2O

  • Mr = 496.37

  • Triclinic, [P \overline 1]

  • a = 9.7426 (7) Å

  • b = 9.8821 (7) Å

  • c = 11.8356 (8) Å

  • [alpha] = 80.107 (1)°

  • [beta] = 73.140 (1)°

  • [gamma] = 83.297 (1)°

  • V = 1071.60 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.05 mm-1

  • T = 100 K

  • 0.54 × 0.51 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.402, Tmax = 0.728

  • 5431 measured reflections

  • 3717 independent reflections

  • 3392 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.125

  • S = 1.05

  • 3717 reflections

  • 286 parameters

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

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O1W-H1W1...O4i 0.80 (5) 2.52 (5) 3.015 (4) 122 (4)
O1W-H1W1...O5i 0.80 (5) 2.22 (5) 3.008 (4) 166 (4)
O1W-H2W1...O3 0.82 (5) 2.00 (5) 2.809 (4) 169 (5)
O4-H4A...O1Wii 0.79 (4) 1.88 (4) 2.656 (4) 168 (3)
C2-H2A...O1iii 0.93 2.49 3.216 (3) 135
C5-H5A...O4 0.93 2.40 3.241 (3) 150
C18-H18A...O1iv 0.93 2.60 3.476 (5) 158
C10-H10A...Cg1v 0.93 2.78 3.672 (4) 160
C16-H16A...Cg1vi 0.93 2.72 3.543 (3) 148
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) x-1, y, z+1; (v) -x+1, -y, -z+1; (vi) x, y, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: SJ5354 ).


Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Belluti, F., Fontana, G., Bo, L. D., Carenini, N., Giommarelli, C. & Zunino, F. (2010). Bioorg. Med. Chem. 18, 3543-3550.  [CrossRef] [ChemPort] [PubMed]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o1549-o1550.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Frombaum, M., Le Clanche, S., Bonnefont-Rousselot, D. & Borderie, D. (2012). Biochimie, 94, 269-276.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Fun, H. K., Chantrapromma, S. & Jansrisewangwong, P. (2011). Acta Cryst. E67, o105-o106.  [CrossRef] [ChemPort] [IUCr Journals]
Hussain, M., Khan, K. M., Ali, S. I., Parveen, R. & Shim, W. S. (2009). Fibers Polym.. 10, 407-412.  [CrossRef] [ChemPort]
Jindawong, B., Chantrapromma, S., Fun, H.-K., Yu, X.-L. & Karalai, C. (2005). Acta Cryst. E61, o1340-o1342.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Li, X., Lu, H., He, D., Luo, C. & Huang, J. (2013). J. Fluoresc. 23, 1039-1044.  [CrossRef] [ChemPort] [PubMed]
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.  [Web of Science] [CSD] [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, o1623-o1624   [ doi:10.1107/S1600536813027244 ]

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