2,2'-[2,4-Bis(naphthalen-1-yl)cyclo-butane-1,3-di-yl]bis-(1-methyl-pyridinium) diiodide: thermal-induced [2 + 2] cyclo-addition reaction of a heterostilbene.

The asymmetric unit of the title compound, C(36)H(32)N(2) (2+)·2I(-), consists of one half-mol-ecule 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 inter-actions into a layer parallel to the bc plane. Intra- and inter-molecular π-π inter-actions 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

C36H32N2 2+·2I−

M = 746.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.080

S = 1.09

4449 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.92 e Å−3

Δρmin = −0.86 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052433/is5025sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811052433/is5025Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C36H32N22+·2I−	F(000) = 736
Mr = 746.44	Dx = 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

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

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(Fo2) + (0.0278P)2 + 1.442P] where P = (Fo2 + 2Fc2)/3
4449 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 1.92 e Å−3
0 restraints	Δρmin = −0.86 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) .