1-Methyl-2-[(E)-2,4,5-trimeth-oxy-styr-yl]-pyridinium iodide.

In the title compound, C(17)H(20)NO(3) (+)·I(-), the cation exists in the E configuration. The pyridinium and benzene rings are close to coplanar, with a dihedral angle of 7.43 (12)° between them. The three meth-oxy groups of 2,4,5-trimeth-oxy-phenyl are essentially coplanar with the benzene plane, with C-O-C-C torsion angles of 1.0 (3), -1.9 (3) and 3.6 (3)°. A weak intra-molecular C-H⋯O inter-action generates an S(6) ring motif. In the crystal, the cations are stacked in columns in an anti-parallel manner along the a axis through π-π inter-actions, with a centroid-centroid distance of 3.7714 (16) Å. The iodide anion is situated between the columns and linked to the cation by a weak C-H⋯I inter-action.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to nonlinear optical properties and applications of pyridinium and quinolinium derivatives, see: Chanawanno et al. (2010 ▶); Chantrapromma et al. (2010 ▶); Ruanwas et al. (2010 ▶); Williams (1984 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Fun et al. (2009 ▶); Kaewmanee et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C17H20NO3 +·I−

M = 413.24

Triclinic,

a = 8.9109 (1) Å

b = 10.3551 (1) Å

c = 10.8201 (2) Å

α = 113.382 (1)°

β = 109.243 (1)°

γ = 96.831 (1)°

V = 828.51 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.94 mm−1

T = 100 K

0.37 × 0.32 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.534, T max = 0.720

29408 measured reflections

4827 independent reflections

4686 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.084

S = 1.14

4827 reflections

203 parameters

H-atom parameters constrained

Δρmax = 1.85 e Å−3

Δρmin = −0.33 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/S1600536810043254/is2612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043254/is2612Isup2.hkl

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

C17H20NO3+·I−	Z = 2
Mr = 413.24	F(000) = 412
Triclinic, P1	Dx = 1.656 Mg m−3
Hall symbol: -P 1	Melting point = 544–545 K
a = 8.9109 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3551 (1) Å	Cell parameters from 4827 reflections
c = 10.8201 (2) Å	θ = 2.2–30.0°
α = 113.382 (1)°	µ = 1.94 mm−1
β = 109.243 (1)°	T = 100 K
γ = 96.831 (1)°	Block, orange
V = 828.51 (2) Å3	0.37 × 0.32 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	4827 independent reflections
Radiation source: sealed tube	4686 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.534, Tmax = 0.720	k = −14→13
29408 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0418P)2 + 1.7349P] where P = (Fo2 + 2Fc2)/3
4827 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 1.85 e Å−3
0 restraints	Δρmin = −0.33 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	0.63632 (2)	0.272468 (17)	0.263674 (17)	0.01981 (6)
O1	0.1870 (2)	0.19738 (18)	0.43228 (18)	0.0142 (3)
O2	0.0422 (2)	0.40374 (18)	0.85063 (19)	0.0141 (3)
O3	0.1169 (2)	0.20276 (19)	0.92393 (19)	0.0152 (3)
N1	0.3476 (2)	−0.2139 (2)	0.1812 (2)	0.0116 (3)
C1	0.3923 (3)	−0.3317 (3)	0.1060 (3)	0.0164 (4)
H1A	0.3941	−0.3480	0.0156	0.020*
C2	0.4348 (3)	−0.4269 (3)	0.1614 (3)	0.0179 (4)
H2A	0.4628	−0.5085	0.1084	0.022*
C3	0.4351 (3)	−0.3990 (3)	0.2983 (3)	0.0157 (4)
H3A	0.4656	−0.4611	0.3387	0.019*
C4	0.3902 (3)	−0.2792 (2)	0.3738 (2)	0.0133 (4)
H4A	0.3916	−0.2604	0.4657	0.016*
C5	0.3422 (3)	−0.1847 (2)	0.3140 (2)	0.0105 (3)
C6	0.2895 (3)	−0.0589 (2)	0.3851 (2)	0.0118 (4)
H6A	0.2727	0.0048	0.3442	0.014*
C7	0.2639 (3)	−0.0305 (2)	0.5083 (2)	0.0109 (3)
H7A	0.2832	−0.0967	0.5456	0.013*
C8	0.2103 (3)	0.0895 (2)	0.5905 (2)	0.0101 (3)
C9	0.1697 (3)	0.2006 (2)	0.5538 (2)	0.0109 (4)
C10	0.1146 (3)	0.3083 (2)	0.6399 (2)	0.0117 (4)
H10A	0.0887	0.3814	0.6148	0.014*
C11	0.0984 (3)	0.3064 (2)	0.7627 (2)	0.0111 (4)
C12	0.1396 (3)	0.1966 (2)	0.8021 (2)	0.0116 (4)
C13	0.1940 (3)	0.0915 (2)	0.7170 (2)	0.0112 (4)
H13A	0.2210	0.0193	0.7435	0.013*
C14	0.3022 (3)	−0.1177 (3)	0.1125 (3)	0.0177 (4)
H14A	0.3121	−0.1545	0.0198	0.027*
H14B	0.3754	−0.0198	0.1771	0.027*
H14C	0.1899	−0.1165	0.0960	0.027*
C15	0.1497 (3)	0.3104 (3)	0.3933 (3)	0.0196 (5)
H15A	0.1785	0.3010	0.3127	0.029*
H15B	0.2124	0.4049	0.4769	0.029*
H15C	0.0333	0.3012	0.3641	0.029*
C16	0.0013 (3)	0.5189 (3)	0.8167 (3)	0.0163 (4)
H16A	−0.0356	0.5804	0.8869	0.024*
H16B	−0.0855	0.4769	0.7189	0.024*
H16C	0.0977	0.5766	0.8214	0.024*
C17	0.1636 (3)	0.0946 (3)	0.9660 (3)	0.0197 (4)
H17A	0.1415	0.1061	1.0503	0.030*
H17B	0.2798	0.1062	0.9907	0.030*
H17C	0.1008	−0.0016	0.8853	0.030*

	U11	U22	U33	U12	U13	U23
I1	0.02761 (10)	0.01804 (9)	0.01905 (9)	0.00876 (6)	0.01258 (7)	0.01051 (7)
O1	0.0254 (8)	0.0137 (7)	0.0124 (7)	0.0114 (6)	0.0120 (6)	0.0092 (6)
O2	0.0208 (8)	0.0128 (7)	0.0159 (7)	0.0108 (6)	0.0126 (6)	0.0075 (6)
O3	0.0240 (8)	0.0171 (8)	0.0139 (7)	0.0115 (6)	0.0132 (6)	0.0102 (6)
N1	0.0147 (8)	0.0123 (8)	0.0100 (8)	0.0061 (6)	0.0071 (6)	0.0052 (7)
C1	0.0202 (10)	0.0179 (10)	0.0138 (9)	0.0106 (8)	0.0107 (8)	0.0054 (8)
C2	0.0220 (11)	0.0166 (10)	0.0176 (10)	0.0115 (8)	0.0115 (9)	0.0058 (8)
C3	0.0185 (10)	0.0143 (10)	0.0189 (10)	0.0093 (8)	0.0101 (8)	0.0089 (8)
C4	0.0171 (9)	0.0136 (9)	0.0131 (9)	0.0076 (7)	0.0082 (8)	0.0074 (8)
C5	0.0117 (8)	0.0107 (8)	0.0097 (8)	0.0043 (7)	0.0056 (7)	0.0041 (7)
C6	0.0151 (9)	0.0109 (9)	0.0110 (9)	0.0062 (7)	0.0066 (7)	0.0049 (7)
C7	0.0132 (8)	0.0101 (8)	0.0108 (9)	0.0052 (7)	0.0060 (7)	0.0046 (7)
C8	0.0122 (8)	0.0101 (8)	0.0098 (8)	0.0048 (7)	0.0061 (7)	0.0046 (7)
C9	0.0138 (9)	0.0114 (9)	0.0093 (8)	0.0050 (7)	0.0058 (7)	0.0052 (7)
C10	0.0149 (9)	0.0111 (9)	0.0120 (9)	0.0061 (7)	0.0070 (7)	0.0064 (7)
C11	0.0122 (8)	0.0107 (9)	0.0117 (9)	0.0053 (7)	0.0071 (7)	0.0041 (7)
C12	0.0138 (9)	0.0134 (9)	0.0109 (9)	0.0060 (7)	0.0072 (7)	0.0066 (7)
C13	0.0142 (9)	0.0115 (9)	0.0109 (9)	0.0055 (7)	0.0066 (7)	0.0062 (7)
C14	0.0277 (11)	0.0193 (10)	0.0157 (10)	0.0122 (9)	0.0133 (9)	0.0120 (9)
C15	0.0355 (13)	0.0173 (10)	0.0165 (10)	0.0149 (9)	0.0146 (9)	0.0125 (9)
C16	0.0205 (10)	0.0128 (9)	0.0216 (11)	0.0100 (8)	0.0128 (9)	0.0089 (8)
C17	0.0298 (12)	0.0228 (11)	0.0190 (11)	0.0142 (10)	0.0154 (9)	0.0152 (9)

O1—C9	1.362 (2)	C7—H7A	0.9300
O1—C15	1.432 (3)	C8—C9	1.407 (3)
O2—C11	1.358 (2)	C8—C13	1.416 (3)
O2—C16	1.433 (3)	C9—C10	1.399 (3)
O3—C12	1.377 (3)	C10—C11	1.391 (3)
O3—C17	1.423 (3)	C10—H10A	0.9300
N1—C1	1.360 (3)	C11—C12	1.411 (3)
N1—C5	1.366 (3)	C12—C13	1.375 (3)
N1—C14	1.481 (3)	C13—H13A	0.9300
C1—C2	1.372 (3)	C14—H14A	0.9600
C1—H1A	0.9300	C14—H14B	0.9600
C2—C3	1.391 (3)	C14—H14C	0.9600
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.378 (3)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.406 (3)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.448 (3)	C16—H16C	0.9600
C6—C7	1.350 (3)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.451 (3)	C17—H17C	0.9600
C9—O1—C15	118.29 (17)	C9—C10—H10A	119.8
C11—O2—C16	117.54 (18)	O2—C11—C10	124.67 (19)
C12—O3—C17	115.34 (17)	O2—C11—C12	115.43 (18)
C1—N1—C5	122.11 (19)	C10—C11—C12	119.89 (19)
C1—N1—C14	117.39 (19)	C13—C12—O3	125.15 (19)
C5—N1—C14	120.50 (18)	C13—C12—C11	119.29 (19)
N1—C1—C2	121.0 (2)	O3—C12—C11	115.53 (18)
N1—C1—H1A	119.5	C12—C13—C8	122.16 (19)
C2—C1—H1A	119.5	C12—C13—H13A	118.9
C1—C2—C3	118.8 (2)	C8—C13—H13A	118.9
C1—C2—H2A	120.6	N1—C14—H14A	109.5
C3—C2—H2A	120.6	N1—C14—H14B	109.5
C4—C3—C2	119.8 (2)	H14A—C14—H14B	109.5
C4—C3—H3A	120.1	N1—C14—H14C	109.5
C2—C3—H3A	120.1	H14A—C14—H14C	109.5
C3—C4—C5	121.0 (2)	H14B—C14—H14C	109.5
C3—C4—H4A	119.5	O1—C15—H15A	109.5
C5—C4—H4A	119.5	O1—C15—H15B	109.5
N1—C5—C4	117.30 (19)	H15A—C15—H15B	109.5
N1—C5—C6	118.57 (19)	O1—C15—H15C	109.5
C4—C5—C6	124.13 (19)	H15A—C15—H15C	109.5
C7—C6—C5	122.6 (2)	H15B—C15—H15C	109.5
C7—C6—H6A	118.7	O2—C16—H16A	109.5
C5—C6—H6A	118.7	O2—C16—H16B	109.5
C6—C7—C8	128.7 (2)	H16A—C16—H16B	109.5
C6—C7—H7A	115.6	O2—C16—H16C	109.5
C8—C7—H7A	115.6	H16A—C16—H16C	109.5
C9—C8—C13	117.62 (18)	H16B—C16—H16C	109.5
C9—C8—C7	126.06 (19)	O3—C17—H17A	109.5
C13—C8—C7	116.29 (18)	O3—C17—H17B	109.5
O1—C9—C10	122.56 (19)	H17A—C17—H17B	109.5
O1—C9—C8	116.78 (18)	O3—C17—H17C	109.5
C10—C9—C8	120.65 (19)	H17A—C17—H17C	109.5
C11—C10—C9	120.37 (19)	H17B—C17—H17C	109.5
C11—C10—H10A	119.8
C5—N1—C1—C2	−0.2 (3)	C7—C8—C9—O1	−2.0 (3)
C14—N1—C1—C2	−179.5 (2)	C13—C8—C9—C10	−0.3 (3)
N1—C1—C2—C3	−1.5 (4)	C7—C8—C9—C10	178.1 (2)
C1—C2—C3—C4	1.3 (4)	O1—C9—C10—C11	179.8 (2)
C2—C3—C4—C5	0.6 (4)	C8—C9—C10—C11	−0.3 (3)
C1—N1—C5—C4	2.0 (3)	C16—O2—C11—C10	−1.9 (3)
C14—N1—C5—C4	−178.8 (2)	C16—O2—C11—C12	178.99 (19)
C1—N1—C5—C6	−178.5 (2)	C9—C10—C11—O2	−178.3 (2)
C14—N1—C5—C6	0.6 (3)	C9—C10—C11—C12	0.8 (3)
C3—C4—C5—N1	−2.2 (3)	C17—O3—C12—C13	3.6 (3)
C3—C4—C5—C6	178.4 (2)	C17—O3—C12—C11	−178.1 (2)
N1—C5—C6—C7	173.0 (2)	O2—C11—C12—C13	178.53 (19)
C4—C5—C6—C7	−7.7 (3)	C10—C11—C12—C13	−0.6 (3)
C5—C6—C7—C8	−179.5 (2)	O2—C11—C12—O3	0.1 (3)
C6—C7—C8—C9	1.7 (4)	C10—C11—C12—O3	−179.03 (19)
C6—C7—C8—C13	−179.9 (2)	O3—C12—C13—C8	178.2 (2)
C15—O1—C9—C10	1.0 (3)	C11—C12—C13—C8	0.0 (3)
C15—O1—C9—C8	−178.9 (2)	C9—C8—C13—C12	0.4 (3)
C13—C8—C9—O1	179.63 (19)	C7—C8—C13—C12	−178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1	0.93	2.19	2.819 (3)	124
C14—H14A···I1i	0.96	3.03	3.992 (3)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1	0.93	2.19	2.819 (3)	124
C14—H14A⋯I1i	0.96	3.03	3.992 (3)	177

Symmetry code: (i) .