2,2′-[2,4-Bis(naphthalen-1-yl)cyclo­butane-1,3-di­yl]bis­(1-methyl­pyridinium) diiodide: thermal-induced [2 + 2] cyclo­addition reaction of a heterostilbeneThis paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand on the occasion of his 84th birthday, which fell on December 5th, 2011.

Chantrapromma, S.; Chanawanno, K.; Boonnak, N.; Fun, H.-K.

doi:10.1107/S1600536811052433

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 (C-C) = 0.005 Å
R = 0.042
wR = 0.080
Data-to-parameter ratio = 23.4
Details

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

Suchada Chantrapromma,^a ^*⁺ Kullapa Chanawanno,^a Nawong Boonnak ^a and Hoong-Kun Fun ^b ⁺⁺

^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-HI 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). For background to stilbene and [2 + 2] photodimerization, see: Chanawanno et al. (2010); Papaefstathiou et al. (2002); Ruanwas et al. (2010); Yayli et al. (2004). For related structures, see: Fun, Chanawanno & Chantrapromma (2009); Fun, Surasit et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₃₆H₃₂N₂²⁺·2I^-
M_r = 746.44
Monoclinic, P 2₁ /c
a = 7.0061 (1) Å
b = 20.7920 (4) Å
c = 10.8956 (2) Å
= 106.063 (1)°
V = 1525.21 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.749, T_max = 0.854
18762 measured reflections
4449 independent reflections
3475 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(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
_max = 1.92 e Å^-3
_min = -0.86 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H14AI1ⁱ	0.93	3.00	3.915 (3)	169
C17-H17AI1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2048-o2049.
Fun, H.-K., Surasit, C., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2346-o2347.
Papaefstathiou, G. S., Friscic, T. & MacGillivray, L. R. (2002). J. Supramol. Chem. 2, 227-231.
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yayli, N., Üçüncü, O., Yasar, A., Gök, Y., Küçük, M. & Kolayli, S. (2004). Turk. J. Chem. 28, 515-521.