(E)-2-[4-(Dimethyl-amino)-styr-yl]-1-methyl-pyridinium triiodide.

The asymmetric unit of the title compound, C(16)H(19)N(2) (+)·I(3) (-), contains a (E)-2-[4-(dimethyl-amino)-styr-yl)-1-methyl-pyrid-in-ium cation and half each of two triiodide anions. The complete triiodide anions are each generated by inversion symmetry. The planar cation has all of its eighteen non-H atoms situated on a mirror plane. In the crystal, the cations are stacked along the b axis by π-π inter-actions with a centroid-centroid distance of 3.5757 (13) Å. The triiodide anions are located between the cations. The crystal structure is further consolidated by short C⋯C [3.322 (9)-3.3952 (19) Å] contacts.

Related literature

For background to and applications of pyridinium compounds, see: Chanawanno et al. (2010 ▶); Fisicaro et al. (1990 ▶); Pernak et al. (2001 ▶). For related structures, see: Chantrapromma et al. (2010 ▶); Zhang et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H19N2 +·I3 −

M = 620.03

Monoclinic,

a = 19.8760 (3) Å

b = 6.6126 (1) Å

c = 14.4421 (2) Å

β = 95.107 (1)°

V = 1890.62 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.96 mm−1

T = 100 K

0.45 × 0.15 × 0.04 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.212, T max = 0.838

16143 measured reflections

2484 independent reflections

2263 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.04

2484 reflections

129 parameters

H-atom parameters constrained

Δρmax = 1.74 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811028753/sj5182sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028753/sj5182Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028753/sj5182Isup3.cml

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

C16H19N2+·I3−	F(000) = 1152
Mr = 620.03	Dx = 2.178 Mg m−3
Monoclinic, C2/m	Melting point > 537 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 19.8760 (3) Å	Cell parameters from 2484 reflections
b = 6.6126 (1) Å	θ = 1.4–28.0°
c = 14.4421 (2) Å	µ = 4.96 mm−1
β = 95.107 (1)°	T = 100 K
V = 1890.62 (5) Å3	Needle, orange
Z = 4	0.45 × 0.15 × 0.04 mm

Bruker APEX DUO CCD area-detector diffractometer	2484 independent reflections
Radiation source: sealed tube	2263 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.212, Tmax = 0.838	k = −8→8
16143 measured reflections	l = −19→18

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0387P)2 + 13.6577P] where P = (Fo2 + 2Fc2)/3
2484 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 1.74 e Å−3
0 restraints	Δρmin = −0.60 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	0.5000	0.5000	0.0000	0.02351 (12)
I2	0.424696 (18)	0.5000	0.16345 (3)	0.03339 (11)
I3	0.5000	0.5000	0.5000	0.03354 (14)
I4	0.35817 (2)	0.5000	0.42352 (3)	0.03813 (12)
N1	0.2700 (3)	0.0000	1.2529 (3)	0.0300 (10)
N2	0.4157 (3)	0.0000	0.6794 (4)	0.0393 (12)
C1	0.2277 (3)	0.0000	1.3233 (4)	0.0338 (13)
H1A	0.2472	0.0000	1.3858	0.041*
C2	0.1609 (3)	0.0000	1.3078 (4)	0.0356 (13)
H2A	0.1331	0.0000	1.3580	0.043*
C3	0.1319 (3)	0.0000	1.2140 (4)	0.0329 (12)
H3A	0.0842	0.0000	1.2007	0.039*
C4	0.1724 (3)	0.0000	1.1446 (4)	0.0319 (12)
H4A	0.1530	0.0000	1.0820	0.038*
C5	0.2453 (3)	0.0000	1.1631 (4)	0.0288 (11)
C6	0.2883 (3)	0.0000	1.0881 (4)	0.0255 (10)
H6A	0.3355	0.0000	1.1052	0.031*
C7	0.2692 (3)	0.0000	0.9977 (4)	0.0275 (11)
H7A	0.2218	0.0000	0.9817	0.033*
C8	0.3107 (3)	0.0000	0.9192 (4)	0.0290 (11)
C9	0.2775 (3)	0.0000	0.8304 (4)	0.0289 (11)
H9A	0.2295	0.0000	0.8240	0.035*
C10	0.3105 (3)	0.0000	0.7535 (4)	0.0272 (11)
H10A	0.2852	0.0000	0.6945	0.033*
C11	0.3815 (3)	0.0000	0.7579 (4)	0.0232 (10)
C12	0.4171 (3)	0.0000	0.8475 (4)	0.0272 (11)
H12A	0.4651	0.0000	0.8536	0.033*
C13	0.3818 (3)	0.0000	0.9268 (4)	0.0336 (12)
H13A	0.4059	0.0000	0.9866	0.040*
C14	0.3424 (3)	0.0000	1.2755 (5)	0.0361 (13)
H14A	0.3599	0.1166	1.2461	0.043*
H14B	0.3546	0.0000	1.3414	0.043*
C15	0.3804 (4)	0.0000	0.5885 (4)	0.0391 (14)
H15A	0.3516	0.1166	0.5844	0.047*
H15B	0.4110	0.0000	0.5407	0.047*
C16	0.4903 (3)	0.0000	0.6862 (5)	0.0460 (16)
H16A	0.5052	0.1166	0.7219	0.055*
H16B	0.5073	0.0000	0.6261	0.055*

	U11	U22	U33	U12	U13	U23
I1	0.0208 (2)	0.0210 (2)	0.0277 (2)	0.000	−0.00351 (16)	0.000
I2	0.03043 (19)	0.0368 (2)	0.0338 (2)	0.000	0.00747 (14)	0.000
I3	0.0526 (3)	0.0261 (3)	0.0232 (2)	0.000	0.0100 (2)	0.000
I4	0.0541 (3)	0.0367 (2)	0.02383 (19)	0.000	0.00475 (16)	0.000
N1	0.038 (2)	0.023 (2)	0.028 (2)	0.000	−0.0003 (19)	0.000
N2	0.047 (3)	0.044 (3)	0.028 (2)	0.000	0.011 (2)	0.000
C1	0.059 (4)	0.018 (2)	0.026 (3)	0.000	0.014 (2)	0.000
C2	0.054 (4)	0.023 (3)	0.031 (3)	0.000	0.010 (3)	0.000
C3	0.038 (3)	0.023 (3)	0.037 (3)	0.000	0.002 (2)	0.000
C4	0.052 (3)	0.020 (2)	0.022 (2)	0.000	−0.005 (2)	0.000
C5	0.050 (3)	0.015 (2)	0.023 (2)	0.000	0.011 (2)	0.000
C6	0.036 (3)	0.017 (2)	0.024 (2)	0.000	0.004 (2)	0.000
C7	0.033 (3)	0.022 (2)	0.027 (3)	0.000	0.002 (2)	0.000
C8	0.039 (3)	0.017 (2)	0.034 (3)	0.000	0.013 (2)	0.000
C9	0.026 (2)	0.017 (2)	0.044 (3)	0.000	0.005 (2)	0.000
C10	0.027 (2)	0.017 (2)	0.036 (3)	0.000	−0.008 (2)	0.000
C11	0.033 (3)	0.017 (2)	0.021 (2)	0.000	0.0046 (19)	0.000
C12	0.025 (2)	0.025 (3)	0.030 (3)	0.000	−0.003 (2)	0.000
C13	0.052 (3)	0.025 (3)	0.022 (3)	0.000	−0.008 (2)	0.000
C14	0.040 (3)	0.030 (3)	0.038 (3)	0.000	0.005 (2)	0.000
C15	0.052 (4)	0.037 (3)	0.028 (3)	0.000	0.004 (3)	0.000
C16	0.040 (3)	0.056 (4)	0.044 (4)	0.000	0.015 (3)	0.000

I1—I2i	2.9054 (4)	C6—H6A	0.9500
I1—I2	2.9054 (4)	C7—C8	1.459 (8)
I3—I4	2.9347 (4)	C7—H7A	0.9500
I3—I4ii	2.9347 (4)	C8—C9	1.389 (8)
N1—C5	1.346 (7)	C8—C13	1.407 (9)
N1—C1	1.375 (7)	C9—C10	1.339 (8)
N1—C14	1.448 (8)	C9—H9A	0.9500
N2—C11	1.373 (7)	C10—C11	1.407 (7)
N2—C15	1.433 (8)	C10—H10A	0.9500
N2—C16	1.476 (9)	C11—C12	1.420 (7)
C1—C2	1.327 (9)	C12—C13	1.396 (8)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.425 (9)	C13—H13A	0.9500
C2—H2A	0.9500	C14—H14A	0.9601
C3—C4	1.341 (9)	C14—H14B	0.9600
C3—H3A	0.9500	C15—H15A	0.9600
C4—C5	1.449 (9)	C15—H15B	0.9598
C4—H4A	0.9500	C16—H16A	0.9600
C5—C6	1.438 (7)	C16—H16B	0.9600
C6—C7	1.327 (8)
I2i—I1—I2	180.000 (12)	C8—C7—H7A	115.4
I4—I3—I4ii	180.0	C9—C8—C13	117.6 (5)
C5—N1—C1	121.2 (5)	C9—C8—C7	117.5 (5)
C5—N1—C14	119.2 (5)	C13—C8—C7	124.9 (5)
C1—N1—C14	119.6 (5)	C10—C9—C8	122.6 (5)
C11—N2—C15	121.2 (5)	C10—C9—H9A	118.7
C11—N2—C16	120.9 (5)	C8—C9—H9A	118.7
C15—N2—C16	117.9 (5)	C9—C10—C11	121.7 (5)
C2—C1—N1	122.9 (6)	C9—C10—H10A	119.2
C2—C1—H1A	118.6	C11—C10—H10A	119.2
N1—C1—H1A	118.6	N2—C11—C10	122.2 (5)
C1—C2—C3	118.4 (6)	N2—C11—C12	120.6 (5)
C1—C2—H2A	120.8	C10—C11—C12	117.3 (5)
C3—C2—H2A	120.8	C13—C12—C11	120.1 (5)
C4—C3—C2	119.4 (6)	C13—C12—H12A	120.0
C4—C3—H3A	120.3	C11—C12—H12A	120.0
C2—C3—H3A	120.3	C12—C13—C8	120.8 (5)
C3—C4—C5	121.3 (5)	C12—C13—H13A	119.6
C3—C4—H4A	119.4	C8—C13—H13A	119.6
C5—C4—H4A	119.4	N1—C14—H14A	106.9
N1—C5—C6	122.4 (5)	N1—C14—H14B	112.4
N1—C5—C4	116.8 (5)	H14A—C14—H14B	111.7
C6—C5—C4	120.8 (5)	N2—C15—H15A	107.3
C7—C6—C5	127.2 (5)	N2—C15—H15B	111.7
C7—C6—H6A	116.4	H15A—C15—H15B	111.7
C5—C6—H6A	116.4	N2—C16—H16A	107.2
C6—C7—C8	129.3 (5)	N2—C16—H16B	111.9
C6—C7—H7A	115.4	H16A—C16—H16B	111.7
C5—N1—C1—C2	0.000 (3)	C6—C7—C8—C13	0.000 (2)
C14—N1—C1—C2	180.000 (2)	C13—C8—C9—C10	0.000 (2)
N1—C1—C2—C3	0.000 (3)	C7—C8—C9—C10	180.000 (2)
C1—C2—C3—C4	0.000 (3)	C8—C9—C10—C11	0.000 (2)
C2—C3—C4—C5	0.000 (3)	C15—N2—C11—C10	0.000 (2)
C1—N1—C5—C6	180.000 (2)	C16—N2—C11—C10	180.000 (1)
C14—N1—C5—C6	0.000 (3)	C15—N2—C11—C12	180.000 (1)
C1—N1—C5—C4	0.000 (3)	C16—N2—C11—C12	0.000 (2)
C14—N1—C5—C4	180.000 (2)	C9—C10—C11—N2	180.000 (1)
C3—C4—C5—N1	0.000 (2)	C9—C10—C11—C12	0.000 (2)
C3—C4—C5—C6	180.000 (2)	N2—C11—C12—C13	180.000 (2)
N1—C5—C6—C7	180.000 (2)	C10—C11—C12—C13	0.000 (2)
C4—C5—C6—C7	0.000 (3)	C11—C12—C13—C8	0.000 (2)
C5—C6—C7—C8	180.000 (2)	C9—C8—C13—C12	0.000 (2)
C6—C7—C8—C9	180.000 (2)	C7—C8—C13—C12	180.000 (2)