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Volume 68 
Part 1 
Pages o67-o68  
January 2012  

Received 3 December 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.080
Data-to-parameter ratio = 23.4
Details
Open access

2,2'-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) diiodide: thermal-induced [2 + 2] cycloaddition reaction of a heterostilbene1

aCrystal Materials Research Unit, Department 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

The asymmetric unit of the title compound, C36H32N22+·2I-, consists of one half-molecule of the cation and one I- anion. The cation is located on an inversion centre. The dihedral angle between the pyridinium ring and the naphthalene ring system in the asymmetric unit is 19.01 (14)°. In the crystal, the cations and the anions are linked by C-H...I interactions into a layer parallel to the bc plane. Intra- and intermolecular [pi]-[pi] interactions with centroid-centroid distances of 3.533 (2)-3.807 (2) Å are also observed.

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 background to stilbene and [2 + 2] photodimerization, see: Chanawanno et al. (2010[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.]); Papaefstathiou et al. (2002[Papaefstathiou, G. S., Friscic, T. & MacGillivray, L. R. (2002). J. Supramol. Chem. 2, 227-231.]); 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.]); Yayli et al. (2004[Yayli, N., Üçüncü, O., Yasar, A., Gök, Y., Küçük, M. & Kolayli, S. (2004). Turk. J. Chem. 28, 515-521.]). For related structures, see: Fun, Chanawanno & Chantrapromma (2009[Fun, H.-K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2048-o2049.]); Fun, Surasit et al. (2009[Fun, H.-K., Surasit, C., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2346-o2347.]). 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
  • C36H32N22+·2I-

  • Mr = 746.44

  • Monoclinic, P 21 /c

  • a = 7.0061 (1) Å

  • b = 20.7920 (4) Å

  • c = 10.8956 (2) Å

  • [beta] = 106.063 (1)°

  • V = 1525.21 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.09 mm-1

  • T = 100 K

  • 0.15 × 0.13 × 0.08 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 = 0.749, Tmax = 0.854

  • 18762 measured reflections

  • 4449 independent reflections

  • 3475 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.080

  • S = 1.09

  • 4449 reflections

  • 190 parameters

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

  • [Delta][rho]max = 1.92 e Å-3

  • [Delta][rho]min = -0.86 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14A...I1i 0.93 3.00 3.915 (3) 169
C17-H17A...I1ii 0.93 2.93 3.840 (3) 167
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5025 ).


Acknowledgements

KC thanks the Crystal Materials Research Unit, Prince of Songkla University, for a research assistance fellowship. NW thanks the Prince of Songkla University for a postdoctoral fellowship. The authors thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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.
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.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Fun, H.-K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2048-o2049.  [CSD] [CrossRef] [details]
Fun, H.-K., Surasit, C., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2346-o2347.  [CSD] [CrossRef] [details]
Papaefstathiou, G. S., Friscic, T. & MacGillivray, L. R. (2002). J. Supramol. Chem. 2, 227-231.  [CSD] [CrossRef] [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.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yayli, N., Üçüncü, O., Yasar, A., Gök, Y., Küçük, M. & Kolayli, S. (2004). Turk. J. Chem. 28, 515-521.  [ChemPort]


Acta Cryst (2012). E68, o67-o68   [ doi:10.1107/S1600536811052433 ]

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