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

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

doi:10.1107/S1600536811052433

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o67-o68

doi:10.1107/S1600536811052433

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

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

(Received 3 December 2011; accepted 5 December 2011; online 10 December 2011)

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 π–π 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
β = 106.063 (1)°
V = 1525.21 (5) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(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
Δρ_max = 1.92 e Å⁻³
Δρ_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); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811052433/is5025sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052433/is5025Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052433/is5025Isup3.cml

checkCIF report

Comment top

Stilbene derivatives have been reported to exhibit non-linear optical (NLO) property (Ruanwas et al., 2010) and antibacterial activity (Chanawanno et al., 2010). It has led us to investigate the bioactivity of [2 + 2] cycloaddition product of stibene derivatives. In general the [2 + 2] dimerization of stilbene can occurred by photoinduced cycloaddition reaction (Papaefstathiou et al., 2002). In our case, however, the [2,2'-(2,4-di(naphthalen-1-yl)cyclobutane-1,3-diyl)bis(1-methylpyridinium)] diiodide, compound (I), was produced by thermal-induced [2 + 2] cycloaddition reaction of (E)-1-methyl-2-[2-(1-naphthyl)vinyl)pyridinium iodide in hot methanol at 323 K. We have also previously reported the crystal structures of the [2 + 2] cycloaddition compounds (Fun, Chanawanno and Chantrapromma, 2009; Fun, Surasit et al., 2009).

The molecular structure of the title compound consists of one C₃₆H₃₂N₂²⁺ cation and two I^- anions (Fig. 1). The cation lie on and the anion lie near an inversion center. The naphthalene (C1–C10) ring system is planar with an r.m.s. deviation of 0.0479 (4) Å. The dihedral angle between the pyridine (N1/C13–C17) ring and the naphthalenyl ring system is 19.01 (14)°. The steroisomer of (I) is syn head-to-tail (Yayli et al., 2004), and the torsion angle C10–C11–C12–C13 = 1.8 (4)°. The cyclobutane ring makes the dihedral angles of 88.1 (2), 75.9 (2) and 70.8 (2)° with the N1/C13–C17, C1–C6 and C1/C6–C10 rings, respectively. The bond lengths in cation are in normal ranges (Allen et al., 1987) and comparable with those in related structures (Fun, Surasit et al., 2009; Fun, Chanawanno & Chantrapromma, 2009).

The crystal packing of (I) is shown in Fig. 2. The anions are located in the interstitials of the cations and linked with the cations into three-dimensional network by C—H···I interactions (Table 1). π–π interactions were presented with distances of Cg1···Cg2 = 3.580 (2) Å, Cg1···Cg3 = 3.533 (2) Å, Cg1···Cg2^{iii, iv} = 3.807 (2) Å [symmetry codes: (iii) -1 + x, y, z; (iv) 1 + x, y, z]; Cg1, Cg2 and Cg3 are the centroids of N1/C13–C17, C1–C6 and C1/C6–C10 rings, respectively.

Related literature top

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 top

A solution of (E)-1-methyl-2-[2-(1-naphthyl)vinyl)pyridinium iodide (500 mg) in CH₃OH (20 ml) was heated at 323 K until a clear solution was obtained and then left to stand at room temperature overnight. The yellow powder which is the product of [2 + 2] cycloaddition reaction of heterostilbene was formed. Yellow block-shaped single crystals of compound (I) suitable for X-ray structure determination were obtained after recrystallization in CH₃OH by slow evaporation of the solvent at room temperature after a few weeks.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. The suffix A corresponds to symmetry code 1 - x, 1 - y, 1 - z.
	Fig. 2. The crystal packing of the title compound viewed down the a axis. C—H···I interactions are shown as dashed lines.

2,2'-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) diiodide top

Crystal data top

C₃₆H₃₂N₂²⁺·2I⁻	F(000) = 736
M_r = 746.44	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4449 reflections
a = 7.0061 (1) Å	θ = 2.2–30.0°
b = 20.7920 (4) Å	µ = 2.09 mm⁻¹
c = 10.8956 (2) Å	T = 100 K
β = 106.063 (1)°	Block, yellow
V = 1525.21 (5) Å³	0.15 × 0.13 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	4449 independent reflections
Radiation source: sealed tube	3475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.749, T_max = 0.854	k = −22→29
18762 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0278P)² + 1.442P] where P = (F_o² + 2F_c²)/3
4449 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 1.92 e Å⁻³
0 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

C₃₆H₃₂N₂²⁺·2I⁻	V = 1525.21 (5) Å³
M_r = 746.44	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0061 (1) Å	µ = 2.09 mm⁻¹
b = 20.7920 (4) Å	T = 100 K
c = 10.8956 (2) Å	0.15 × 0.13 × 0.08 mm
β = 106.063 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4449 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3475 reflections with I > 2σ(I)
T_min = 0.749, T_max = 0.854	R_int = 0.050
18762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 1.92 e Å⁻³
4449 reflections	Δρ_min = −0.86 e Å⁻³
190 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.51619 (4)	0.361747 (10)	0.802649 (19)	0.02498 (7)
N1	0.5483 (4)	0.35243 (12)	0.3555 (2)	0.0160 (5)
C1	0.0993 (5)	0.40695 (16)	0.3501 (3)	0.0195 (6)
C2	0.1492 (5)	0.35697 (16)	0.4416 (3)	0.0235 (7)
H2A	0.2212	0.3664	0.5250	0.028*
C3	0.0915 (5)	0.29415 (17)	0.4080 (4)	0.0291 (8)
H3A	0.1233	0.2618	0.4692	0.035*
C4	−0.0154 (5)	0.27911 (19)	0.2811 (4)	0.0347 (9)
H4A	−0.0477	0.2366	0.2576	0.042*
C5	−0.0712 (5)	0.3272 (2)	0.1930 (4)	0.0313 (9)
H5A	−0.1445	0.3170	0.1103	0.038*
C6	−0.0201 (5)	0.39223 (18)	0.2246 (3)	0.0241 (8)
C7	−0.0847 (5)	0.44256 (19)	0.1352 (3)	0.0276 (8)
H7A	−0.1624	0.4331	0.0532	0.033*
C8	−0.0340 (5)	0.50453 (19)	0.1684 (3)	0.0281 (8)
H8A	−0.0860	0.5375	0.1113	0.034*
C9	0.0972 (5)	0.51915 (17)	0.2890 (3)	0.0226 (7)
H9A	0.1347	0.5617	0.3086	0.027*
C10	0.1710 (5)	0.47208 (15)	0.3781 (3)	0.0182 (6)
C11	0.3468 (5)	0.48207 (15)	0.4937 (3)	0.0168 (6)
C12	0.5522 (5)	0.45067 (14)	0.4853 (3)	0.0145 (6)
C13	0.5385 (4)	0.41782 (15)	0.3610 (3)	0.0153 (6)
C14	0.4890 (5)	0.45169 (15)	0.2464 (3)	0.0174 (6)
H14A	0.4889	0.4964	0.2474	0.021*
C15	0.4397 (5)	0.41930 (16)	0.1308 (3)	0.0203 (7)
H15A	0.4098	0.4422	0.0545	0.024*
C16	0.4353 (5)	0.35306 (16)	0.1291 (3)	0.0229 (7)
H16A	0.3934	0.3308	0.0523	0.027*
C17	0.4939 (5)	0.32046 (16)	0.2430 (3)	0.0215 (7)
H17A	0.4961	0.2757	0.2427	0.026*
C18	0.6237 (5)	0.31341 (15)	0.4735 (3)	0.0203 (7)
H18A	0.7586	0.3253	0.5149	0.030*
H18B	0.6182	0.2686	0.4515	0.030*
H18C	0.5430	0.3211	0.5303	0.030*
H11	0.305 (5)	0.4670 (18)	0.574 (3)	0.026 (10)*
H12	0.610 (5)	0.4215 (17)	0.560 (3)	0.019 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.04756 (15)	0.01318 (10)	0.01593 (10)	−0.00056 (11)	0.01167 (8)	0.00136 (9)
N1	0.0222 (13)	0.0125 (13)	0.0156 (12)	0.0010 (11)	0.0089 (10)	0.0007 (10)
C1	0.0145 (15)	0.0240 (17)	0.0214 (16)	−0.0010 (13)	0.0071 (12)	−0.0014 (13)
C2	0.0201 (16)	0.0197 (16)	0.0315 (18)	−0.0017 (14)	0.0082 (13)	−0.0016 (14)
C3	0.0250 (19)	0.0199 (17)	0.044 (2)	−0.0014 (15)	0.0115 (16)	0.0018 (15)
C4	0.027 (2)	0.0250 (19)	0.051 (3)	−0.0103 (16)	0.0085 (18)	−0.0148 (17)
C5	0.0227 (18)	0.036 (2)	0.034 (2)	−0.0104 (16)	0.0056 (16)	−0.0149 (17)
C6	0.0143 (15)	0.0321 (19)	0.0263 (19)	−0.0038 (14)	0.0065 (14)	−0.0053 (14)
C7	0.0197 (17)	0.042 (2)	0.0186 (17)	−0.0033 (16)	0.0007 (13)	−0.0016 (15)
C8	0.0182 (17)	0.036 (2)	0.0262 (18)	−0.0011 (15)	−0.0005 (14)	0.0061 (15)
C9	0.0202 (16)	0.0238 (17)	0.0238 (17)	0.0014 (14)	0.0059 (13)	0.0006 (13)
C10	0.0198 (16)	0.0185 (15)	0.0176 (15)	−0.0016 (13)	0.0075 (12)	−0.0048 (12)
C11	0.0186 (15)	0.0155 (14)	0.0165 (14)	0.0007 (12)	0.0053 (12)	−0.0011 (11)
C12	0.0182 (15)	0.0132 (14)	0.0131 (14)	0.0001 (12)	0.0061 (11)	−0.0011 (11)
C13	0.0190 (15)	0.0127 (14)	0.0151 (14)	0.0009 (12)	0.0061 (11)	−0.0017 (12)
C14	0.0206 (16)	0.0144 (15)	0.0184 (14)	−0.0002 (12)	0.0073 (12)	0.0019 (12)
C15	0.0220 (16)	0.0226 (16)	0.0170 (15)	0.0006 (14)	0.0068 (12)	0.0028 (13)
C16	0.0292 (18)	0.0215 (18)	0.0185 (15)	−0.0012 (14)	0.0075 (13)	−0.0028 (13)
C17	0.0326 (19)	0.0131 (15)	0.0206 (15)	−0.0014 (14)	0.0104 (14)	−0.0053 (12)
C18	0.0285 (18)	0.0146 (15)	0.0179 (15)	0.0034 (13)	0.0069 (13)	0.0037 (12)

Geometric parameters (Å, º) top

N1—C17	1.354 (4)	C9—H9A	0.9300
N1—C13	1.363 (4)	C10—C11	1.513 (4)
N1—C18	1.488 (4)	C11—C12ⁱ	1.555 (4)
C1—C2	1.415 (5)	C11—C12	1.606 (4)
C1—C6	1.424 (4)	C11—H11	1.05 (4)
C1—C10	1.447 (4)	C12—C13	1.496 (4)
C2—C3	1.386 (5)	C12—C11ⁱ	1.555 (4)
C2—H2A	0.9300	C12—H12	1.01 (3)
C3—C4	1.413 (5)	C13—C14	1.392 (4)
C3—H3A	0.9300	C14—C15	1.385 (4)
C4—C5	1.365 (6)	C14—H14A	0.9300
C4—H4A	0.9300	C15—C16	1.377 (5)
C5—C6	1.417 (5)	C15—H15A	0.9300
C5—H5A	0.9300	C16—C17	1.373 (5)
C6—C7	1.416 (5)	C16—H16A	0.9300
C7—C8	1.359 (5)	C17—H17A	0.9300
C7—H7A	0.9300	C18—H18A	0.9600
C8—C9	1.413 (5)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18C	0.9600
C9—C10	1.375 (4)

C17—N1—C13	121.6 (3)	C10—C11—C12ⁱ	118.6 (3)
C17—N1—C18	117.3 (3)	C10—C11—C12	115.6 (2)
C13—N1—C18	121.1 (3)	C12ⁱ—C11—C12	89.7 (2)
C2—C1—C6	118.9 (3)	C10—C11—H11	108 (2)
C2—C1—C10	122.3 (3)	C12ⁱ—C11—H11	112 (2)
C6—C1—C10	118.7 (3)	C12—C11—H11	113 (2)
C3—C2—C1	120.6 (3)	C13—C12—C11ⁱ	117.1 (3)
C3—C2—H2A	119.7	C13—C12—C11	113.8 (2)
C1—C2—H2A	119.7	C11ⁱ—C12—C11	90.3 (2)
C2—C3—C4	120.2 (4)	C13—C12—H12	111.6 (19)
C2—C3—H3A	119.9	C11ⁱ—C12—H12	111 (2)
C4—C3—H3A	119.9	C11—C12—H12	111.4 (19)
C5—C4—C3	119.8 (3)	N1—C13—C14	117.9 (3)
C5—C4—H4A	120.1	N1—C13—C12	120.3 (3)
C3—C4—H4A	120.1	C14—C13—C12	121.3 (3)
C4—C5—C6	121.6 (3)	C15—C14—C13	120.5 (3)
C4—C5—H5A	119.2	C15—C14—H14A	119.8
C6—C5—H5A	119.2	C13—C14—H14A	119.8
C7—C6—C5	121.8 (3)	C16—C15—C14	119.8 (3)
C7—C6—C1	119.5 (3)	C16—C15—H15A	120.1
C5—C6—C1	118.7 (3)	C14—C15—H15A	120.1
C8—C7—C6	120.5 (3)	C17—C16—C15	118.8 (3)
C8—C7—H7A	119.8	C17—C16—H16A	120.6
C6—C7—H7A	119.8	C15—C16—H16A	120.6
C7—C8—C9	120.4 (3)	N1—C17—C16	121.0 (3)
C7—C8—H8A	119.8	N1—C17—H17A	119.5
C9—C8—H8A	119.8	C16—C17—H17A	119.5
C10—C9—C8	121.6 (3)	N1—C18—H18A	109.5
C10—C9—H9A	119.2	N1—C18—H18B	109.5
C8—C9—H9A	119.2	H18A—C18—H18B	109.5
C9—C10—C1	118.4 (3)	N1—C18—H18C	109.5
C9—C10—C11	123.4 (3)	H18A—C18—H18C	109.5
C1—C10—C11	117.3 (3)	H18B—C18—H18C	109.5

C6—C1—C2—C3	3.3 (5)	C1—C10—C11—C12ⁱ	170.7 (3)
C10—C1—C2—C3	−174.5 (3)	C9—C10—C11—C12	−103.7 (4)
C1—C2—C3—C4	1.0 (5)	C1—C10—C11—C12	65.9 (4)
C2—C3—C4—C5	−3.5 (6)	C10—C11—C12—C13	1.8 (4)
C3—C4—C5—C6	1.6 (6)	C12ⁱ—C11—C12—C13	−120.0 (3)
C4—C5—C6—C7	−177.3 (3)	C10—C11—C12—C11ⁱ	121.9 (3)
C4—C5—C6—C1	2.6 (5)	C12ⁱ—C11—C12—C11ⁱ	0.0
C2—C1—C6—C7	174.9 (3)	C17—N1—C13—C14	−6.2 (4)
C10—C1—C6—C7	−7.3 (5)	C18—N1—C13—C14	172.5 (3)
C2—C1—C6—C5	−5.0 (5)	C17—N1—C13—C12	165.3 (3)
C10—C1—C6—C5	172.8 (3)	C18—N1—C13—C12	−16.0 (4)
C5—C6—C7—C8	179.8 (3)	C11ⁱ—C12—C13—N1	147.3 (3)
C1—C6—C7—C8	−0.1 (5)	C11—C12—C13—N1	−109.3 (3)
C6—C7—C8—C9	5.2 (5)	C11ⁱ—C12—C13—C14	−41.5 (4)
C7—C8—C9—C10	−2.7 (5)	C11—C12—C13—C14	61.9 (4)
C8—C9—C10—C1	−4.8 (5)	N1—C13—C14—C15	3.8 (5)
C8—C9—C10—C11	164.7 (3)	C12—C13—C14—C15	−167.6 (3)
C2—C1—C10—C9	−172.6 (3)	C13—C14—C15—C16	1.5 (5)
C6—C1—C10—C9	9.6 (5)	C14—C15—C16—C17	−4.6 (5)
C2—C1—C10—C11	17.3 (4)	C13—N1—C17—C16	3.1 (5)
C6—C1—C10—C11	−160.5 (3)	C18—N1—C17—C16	−175.6 (3)
C9—C10—C11—C12ⁱ	1.1 (5)	C15—C16—C17—N1	2.4 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₃₆H₃₂N₂²⁺·2I⁻
M_r	746.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.0061 (1), 20.7920 (4), 10.8956 (2)
β (°)	106.063 (1)
V (Å³)	1525.21 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.15 × 0.13 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.749, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	18762, 4449, 3475
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.080, 1.09
No. of reflections	4449
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.92, −0.86

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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+1/2, z−1/2.

Footnotes

†This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand on the occasion of his 84th birthday, which fell on December 5th, 2011.

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

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.

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