(E)-1-Methyl-2-styrylpyridinium iodide.

In the title compound, C(14)H(14)N(+)·I(-), the cation exists in an E configuration with respect to the ethenyl bond and is slightly twisted, the inter-planar angle between the pyridinium and phenyl rings of the cation being 4.8 (2)°. In the crystal packing, the cations are stacked in an anti-parallel fashion along the a axis by a π-π inter-action involving both pyridinium and phenyl rings; the centroid-centroid distance is 3.542 (3) Å. Each iodide ion is sandwiched between two cations. The cations and iodide anions are linked together by weak C-H⋯I inter-actions, giving rise to ladder-like ribbons along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to non-linear optical materials research, see: Wenseleers et al. (1998 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Chantrapromma et al. (2009a ▶,b ▶); Fun et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C14H14N+·I−

M = 323.16

Monoclinic,

a = 7.0841 (1) Å

b = 10.0664 (2) Å

c = 19.1771 (3) Å

β = 109.017 (1)°

V = 1292.91 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.45 mm−1

T = 100 K

0.28 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.552, T max = 0.735

15764 measured reflections

3753 independent reflections

3186 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.09

3753 reflections

146 parameters

H-atom parameters constrained

Δρmax = 1.53 e Å−3

Δρmin = −1.30 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 datablocks global, I. DOI: 10.1107/S1600536809027810/wn2338sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027810/wn2338Isup2.hkl

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

C14H14N+·I−	F(000) = 632
Mr = 323.16	Dx = 1.660 Mg m−3
Monoclinic, P21/c	Melting point = 505–506 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0841 (1) Å	Cell parameters from 3753 reflections
b = 10.0664 (2) Å	θ = 2.3–30.0°
c = 19.1771 (3) Å	µ = 2.45 mm−1
β = 109.017 (1)°	T = 100 K
V = 1292.91 (4) Å3	Block, pale yellow
Z = 4	0.28 × 0.18 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	3753 independent reflections
Radiation source: sealed tube	3186 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
Tmin = 0.552, Tmax = 0.735	k = −14→14
15764 measured reflections	l = −26→26

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.037P)2 + 4.8574P] where P = (Fo2 + 2Fc2)/3
3753 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 1.53 e Å−3
0 restraints	Δρmin = −1.30 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.70838 (4)	0.18319 (3)	0.382571 (14)	0.03436 (10)
N1	0.6191 (5)	0.7789 (4)	0.45127 (18)	0.0298 (7)
C1	0.5059 (6)	0.8350 (4)	0.3870 (2)	0.0327 (8)
H1A	0.4830	0.9261	0.3851	0.039*
C2	0.4245 (6)	0.7599 (5)	0.3248 (2)	0.0332 (8)
H2A	0.3463	0.7993	0.2811	0.040*
C3	0.4607 (6)	0.6242 (4)	0.3281 (2)	0.0305 (8)
H3A	0.4094	0.5718	0.2863	0.037*
C4	0.5727 (6)	0.5682 (4)	0.3936 (2)	0.0316 (8)
H4A	0.5958	0.4772	0.3962	0.038*
C5	0.6529 (7)	0.6466 (4)	0.4568 (2)	0.0328 (8)
C6	0.7642 (7)	0.5934 (4)	0.5286 (2)	0.0346 (9)
H6A	0.7946	0.6493	0.5694	0.041*
C7	0.8250 (6)	0.4660 (5)	0.5384 (2)	0.0350 (9)
H7A	0.7885	0.4131	0.4964	0.042*
C8	0.9420 (6)	0.4001 (4)	0.6074 (2)	0.0272 (7)
C9	0.9771 (6)	0.2630 (4)	0.6079 (2)	0.0299 (8)
H9A	0.9310	0.2151	0.5641	0.036*
C10	1.0797 (6)	0.1984 (4)	0.6727 (3)	0.0335 (9)
H10A	1.1008	0.1073	0.6724	0.040*
C11	1.1507 (7)	0.2682 (5)	0.7377 (2)	0.0365 (9)
H11A	1.2225	0.2247	0.7810	0.044*
C12	1.1146 (7)	0.4048 (5)	0.7385 (2)	0.0341 (9)
H12A	1.1590	0.4516	0.7826	0.041*
C13	1.0130 (6)	0.4704 (4)	0.6736 (2)	0.0291 (8)
H13A	0.9920	0.5615	0.6742	0.035*
C14	0.7074 (7)	0.8689 (5)	0.5147 (2)	0.0364 (9)
H14A	0.8469	0.8492	0.5367	0.055*
H14B	0.6409	0.8564	0.5505	0.055*
H14C	0.6917	0.9593	0.4980	0.055*

	U11	U22	U33	U12	U13	U23
I1	0.04036 (17)	0.03000 (15)	0.02839 (14)	0.00091 (11)	0.00527 (11)	−0.00118 (10)
N1	0.0326 (17)	0.0315 (17)	0.0280 (15)	−0.0039 (14)	0.0137 (14)	−0.0016 (13)
C1	0.0287 (19)	0.034 (2)	0.036 (2)	0.0047 (16)	0.0115 (16)	0.0009 (16)
C2	0.0278 (19)	0.040 (2)	0.0309 (19)	0.0078 (17)	0.0080 (16)	0.0005 (17)
C3	0.0273 (18)	0.037 (2)	0.0278 (17)	−0.0012 (16)	0.0093 (15)	−0.0019 (16)
C4	0.035 (2)	0.028 (2)	0.0306 (18)	−0.0052 (16)	0.0094 (16)	0.0010 (15)
C5	0.038 (2)	0.0277 (19)	0.0304 (19)	−0.0067 (16)	0.0087 (17)	0.0050 (15)
C6	0.037 (2)	0.032 (2)	0.035 (2)	0.0006 (17)	0.0126 (17)	0.0000 (16)
C7	0.037 (2)	0.033 (2)	0.035 (2)	−0.0014 (17)	0.0115 (17)	0.0006 (17)
C8	0.0288 (18)	0.0266 (18)	0.0270 (16)	−0.0042 (15)	0.0100 (14)	0.0036 (14)
C9	0.0308 (19)	0.0301 (19)	0.0333 (19)	−0.0038 (16)	0.0166 (16)	−0.0037 (15)
C10	0.031 (2)	0.0222 (18)	0.047 (2)	0.0010 (15)	0.0130 (18)	0.0064 (16)
C11	0.033 (2)	0.036 (2)	0.036 (2)	−0.0011 (18)	0.0055 (17)	0.0119 (18)
C12	0.037 (2)	0.038 (2)	0.0268 (18)	−0.0043 (18)	0.0097 (16)	−0.0017 (16)
C13	0.0315 (19)	0.0222 (17)	0.0345 (19)	0.0014 (15)	0.0118 (16)	0.0002 (14)
C14	0.047 (2)	0.030 (2)	0.032 (2)	−0.0036 (19)	0.0130 (18)	−0.0053 (16)

N1—C5	1.352 (5)	C7—H7A	0.9300
N1—C1	1.355 (5)	C8—C13	1.397 (5)
N1—C14	1.481 (5)	C8—C9	1.402 (6)
C1—C2	1.370 (6)	C9—C10	1.381 (6)
C1—H1A	0.9300	C9—H9A	0.9300
C2—C3	1.387 (6)	C10—C11	1.376 (6)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.369 (6)	C11—C12	1.399 (7)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.402 (6)	C12—C13	1.384 (6)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.448 (6)	C13—H13A	0.9300
C6—C7	1.347 (6)	C14—H14A	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—C8	1.470 (6)	C14—H14C	0.9600
C5—N1—C1	121.3 (4)	C13—C8—C9	118.8 (4)
C5—N1—C14	121.4 (4)	C13—C8—C7	121.3 (4)
C1—N1—C14	117.3 (4)	C9—C8—C7	119.8 (4)
N1—C1—C2	121.2 (4)	C10—C9—C8	120.6 (4)
N1—C1—H1A	119.4	C10—C9—H9A	119.7
C2—C1—H1A	119.4	C8—C9—H9A	119.7
C1—C2—C3	119.0 (4)	C11—C10—C9	120.4 (4)
C1—C2—H2A	120.5	C11—C10—H10A	119.8
C3—C2—H2A	120.5	C9—C10—H10A	119.8
C4—C3—C2	119.4 (4)	C10—C11—C12	119.8 (4)
C4—C3—H3A	120.3	C10—C11—H11A	120.1
C2—C3—H3A	120.3	C12—C11—H11A	120.1
C3—C4—C5	120.8 (4)	C13—C12—C11	120.2 (4)
C3—C4—H4A	119.6	C13—C12—H12A	119.9
C5—C4—H4A	119.6	C11—C12—H12A	119.9
N1—C5—C4	118.4 (4)	C12—C13—C8	120.2 (4)
N1—C5—C6	117.8 (4)	C12—C13—H13A	119.9
C4—C5—C6	123.8 (4)	C8—C13—H13A	119.9
C7—C6—C5	122.3 (4)	N1—C14—H14A	109.5
C7—C6—H6A	118.8	N1—C14—H14B	109.5
C5—C6—H6A	118.8	H14A—C14—H14B	109.5
C6—C7—C8	128.1 (4)	N1—C14—H14C	109.5
C6—C7—H7A	116.0	H14A—C14—H14C	109.5
C8—C7—H7A	116.0	H14B—C14—H14C	109.5
C5—N1—C1—C2	−1.3 (6)	C4—C5—C6—C7	10.0 (7)
C14—N1—C1—C2	177.6 (4)	C5—C6—C7—C8	178.5 (4)
N1—C1—C2—C3	−0.4 (6)	C6—C7—C8—C13	−2.8 (7)
C1—C2—C3—C4	1.4 (6)	C6—C7—C8—C9	174.6 (4)
C2—C3—C4—C5	−0.8 (6)	C13—C8—C9—C10	0.2 (6)
C1—N1—C5—C4	1.9 (6)	C7—C8—C9—C10	−177.3 (4)
C14—N1—C5—C4	−176.9 (4)	C8—C9—C10—C11	−0.7 (6)
C1—N1—C5—C6	−175.9 (4)	C9—C10—C11—C12	1.5 (7)
C14—N1—C5—C6	5.3 (6)	C10—C11—C12—C13	−1.9 (7)
C3—C4—C5—N1	−0.8 (6)	C11—C12—C13—C8	1.5 (6)
C3—C4—C5—C6	176.8 (4)	C9—C8—C13—C12	−0.6 (6)
N1—C5—C6—C7	−172.4 (4)	C7—C8—C13—C12	176.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···I1i	0.93	3.05	3.799 (4)	139
C14—H14A···I1ii	0.96	3.04	3.996 (5)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯I1i	0.93	3.05	3.799 (4)	139
C14—H14A⋯I1ii	0.96	3.04	3.996 (5)	173

Symmetry codes: (i) ; (ii) .