2-[(E)-4-(Diethyl-amino)-styr-yl]-1-methyl-pyridinium iodide.

In the title compound, C(18)H(23)N(2) (+)·I(-), the cation exists in the E configuration with respect to the ethenyl C=C bond. The pyridinium and benzene rings are nearly coplanar, making a dihedral angle of 4.63 (7)°. The two ethyl groups of the diethyl-amino substituent point in opposite directions with respect to the benzene plane. In the crystal, the cation and the iodide anion are linked by a weak C-H⋯I inter-action. The cations are stacked in an anti-parallel manner along the a axis by a π-π inter-action with a centroid-centroid distance of 3.5262 (9) Å. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to styryl pyridinium quaternary ammonium compounds, see: Browning et al. (1922 ▶, 1923 ▶); Chanawanno et al. (2010 ▶); Wainwright & Kristiansen (2003 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Fun et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H23N2 +·I−

M = 394.28

Monoclinic,

a = 7.7099 (1) Å

b = 20.2780 (4) Å

c = 10.9375 (2) Å

β = 92.527 (1)°

V = 1708.32 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.87 mm−1

T = 100 K

0.34 × 0.30 × 0.21 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.570, T max = 0.691

23707 measured reflections

6198 independent reflections

5765 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.070

S = 1.10

6198 reflections

282 parameters

All H-atom parameters refined

Δρmax = 0.51 e Å−3

Δρmin = −0.63 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/S1600536810037505/is2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037505/is2599Isup2.hkl

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

C18H23N2+·I−	F(000) = 792
Mr = 394.28	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Melting point = 527–529 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7099 (1) Å	Cell parameters from 6198 reflections
b = 20.2780 (4) Å	θ = 2.0–32.6°
c = 10.9375 (2) Å	µ = 1.87 mm−1
β = 92.527 (1)°	T = 100 K
V = 1708.32 (5) Å3	Block, orange
Z = 4	0.34 × 0.30 × 0.21 mm

Bruker APEXII CCD area detector diffractometer	6198 independent reflections
Radiation source: sealed tube	5765 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 32.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→11
Tmin = 0.570, Tmax = 0.691	k = −29→30
23707 measured reflections	l = −16→16

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0312P)2 + 1.8072P] where P = (Fo2 + 2Fc2)/3
6198 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.63 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	0.385998 (14)	0.649927 (5)	0.254076 (9)	0.01744 (4)
N1	0.27082 (18)	0.63425 (7)	0.69740 (12)	0.0128 (2)
N2	0.1456 (2)	0.33502 (7)	0.09996 (13)	0.0165 (3)
C1	0.3117 (2)	0.66702 (9)	0.80338 (15)	0.0156 (3)
C2	0.3971 (2)	0.63637 (9)	0.89989 (15)	0.0169 (3)
C3	0.4439 (2)	0.57021 (9)	0.88598 (15)	0.0181 (3)
C4	0.4023 (2)	0.53711 (8)	0.77893 (15)	0.0159 (3)
C5	0.3120 (2)	0.56923 (8)	0.68124 (14)	0.0130 (3)
C6	0.2616 (2)	0.53758 (8)	0.56679 (15)	0.0149 (3)
C7	0.3027 (2)	0.47469 (8)	0.53980 (14)	0.0141 (3)
C8	0.2575 (2)	0.44086 (8)	0.42673 (14)	0.0136 (3)
C9	0.1595 (2)	0.46906 (8)	0.32844 (15)	0.0144 (3)
C10	0.1223 (2)	0.43480 (8)	0.22166 (15)	0.0150 (3)
C11	0.1815 (2)	0.36902 (8)	0.20590 (14)	0.0135 (3)
C12	0.2802 (2)	0.34044 (8)	0.30475 (15)	0.0131 (3)
C13	0.3169 (2)	0.37578 (8)	0.41093 (14)	0.0133 (3)
C14	0.0388 (2)	0.36290 (9)	−0.00116 (15)	0.0173 (3)
C15	0.1390 (3)	0.40606 (10)	−0.08716 (17)	0.0216 (3)
C16	0.2067 (2)	0.26717 (8)	0.08518 (15)	0.0164 (3)
C17	0.0948 (3)	0.21691 (9)	0.14881 (17)	0.0201 (3)
C18	0.1817 (2)	0.67224 (9)	0.59821 (16)	0.0182 (3)
H1A	0.285 (3)	0.7107 (13)	0.805 (2)	0.020 (6)*
H2A	0.426 (4)	0.6591 (13)	0.971 (3)	0.029 (7)*
H3A	0.512 (4)	0.5499 (14)	0.954 (3)	0.031 (7)*
H4A	0.434 (3)	0.4942 (13)	0.774 (2)	0.019 (6)*
H6A	0.198 (3)	0.5628 (12)	0.507 (2)	0.014 (5)*
H7A	0.369 (3)	0.4489 (13)	0.598 (2)	0.020 (6)*
H9A	0.120 (3)	0.5160 (13)	0.332 (2)	0.021 (6)*
H10A	0.055 (4)	0.4541 (14)	0.158 (3)	0.027 (7)*
H12A	0.325 (3)	0.2966 (13)	0.298 (2)	0.020 (6)*
H14A	−0.057 (3)	0.3869 (13)	0.030 (2)	0.017 (6)*
H13A	0.384 (3)	0.3571 (11)	0.476 (2)	0.015 (6)*
H14B	−0.013 (3)	0.3265 (13)	−0.047 (2)	0.021 (6)*
H15A	0.061 (4)	0.4195 (15)	−0.156 (3)	0.037 (8)*
H15B	0.238 (4)	0.3824 (14)	−0.117 (2)	0.026 (7)*
H15C	0.180 (4)	0.4425 (15)	−0.047 (3)	0.028 (7)*
H16A	0.323 (3)	0.2637 (13)	0.115 (2)	0.022 (6)*
H16B	0.202 (3)	0.2567 (13)	0.002 (2)	0.020 (6)*
H17A	0.139 (4)	0.1730 (15)	0.135 (3)	0.029 (7)*
H17B	0.098 (3)	0.2228 (14)	0.236 (2)	0.021 (6)*
H17C	−0.022 (4)	0.2207 (14)	0.121 (2)	0.027 (7)*
H18A	0.176 (4)	0.7175 (14)	0.623 (2)	0.027 (7)*
H18B	0.069 (4)	0.6552 (14)	0.586 (3)	0.032 (8)*
H18C	0.244 (4)	0.6682 (14)	0.525 (3)	0.023 (6)*

	U11	U22	U33	U12	U13	U23
I1	0.02091 (6)	0.01714 (6)	0.01425 (6)	0.00473 (4)	0.00049 (4)	0.00028 (3)
N1	0.0135 (6)	0.0121 (6)	0.0130 (5)	0.0000 (4)	0.0022 (4)	0.0001 (4)
N2	0.0239 (7)	0.0128 (6)	0.0126 (6)	0.0009 (5)	−0.0015 (5)	−0.0015 (5)
C1	0.0179 (7)	0.0143 (7)	0.0147 (6)	−0.0003 (5)	0.0036 (5)	−0.0022 (5)
C2	0.0183 (7)	0.0200 (7)	0.0126 (6)	−0.0052 (6)	0.0026 (5)	−0.0017 (5)
C3	0.0205 (7)	0.0187 (7)	0.0149 (6)	−0.0030 (6)	−0.0018 (5)	0.0035 (6)
C4	0.0196 (7)	0.0125 (7)	0.0154 (6)	−0.0013 (5)	−0.0016 (5)	0.0020 (5)
C5	0.0121 (6)	0.0129 (6)	0.0140 (6)	−0.0011 (5)	0.0019 (5)	−0.0003 (5)
C6	0.0161 (7)	0.0143 (7)	0.0142 (6)	0.0000 (5)	−0.0013 (5)	−0.0013 (5)
C7	0.0142 (6)	0.0140 (7)	0.0141 (6)	−0.0010 (5)	0.0006 (5)	−0.0007 (5)
C8	0.0144 (6)	0.0128 (6)	0.0136 (6)	0.0001 (5)	0.0013 (5)	−0.0011 (5)
C9	0.0143 (6)	0.0128 (6)	0.0160 (6)	0.0015 (5)	0.0014 (5)	−0.0003 (5)
C10	0.0168 (7)	0.0137 (7)	0.0146 (6)	0.0021 (5)	−0.0005 (5)	0.0014 (5)
C11	0.0150 (6)	0.0128 (6)	0.0127 (6)	−0.0012 (5)	0.0011 (5)	−0.0010 (5)
C12	0.0134 (6)	0.0122 (6)	0.0140 (6)	−0.0014 (5)	0.0016 (5)	0.0012 (5)
C13	0.0136 (6)	0.0126 (6)	0.0138 (6)	0.0009 (5)	0.0011 (5)	0.0003 (5)
C14	0.0184 (7)	0.0195 (7)	0.0137 (6)	−0.0006 (6)	−0.0029 (5)	−0.0005 (6)
C15	0.0229 (8)	0.0255 (9)	0.0166 (7)	0.0000 (7)	0.0018 (6)	0.0029 (6)
C16	0.0208 (7)	0.0134 (7)	0.0150 (6)	0.0005 (6)	0.0019 (5)	−0.0033 (5)
C17	0.0229 (8)	0.0172 (8)	0.0205 (7)	−0.0029 (6)	0.0025 (6)	−0.0042 (6)
C18	0.0213 (8)	0.0171 (7)	0.0161 (7)	0.0037 (6)	−0.0008 (6)	0.0014 (6)

N1—C1	1.361 (2)	C9—H9A	1.00 (3)
N1—C5	1.369 (2)	C10—C11	1.423 (2)
N1—C18	1.475 (2)	C10—H10A	0.93 (3)
N2—C11	1.366 (2)	C11—C12	1.418 (2)
N2—C14	1.463 (2)	C12—C13	1.383 (2)
N2—C16	1.466 (2)	C12—H12A	0.96 (3)
C1—C2	1.368 (2)	C13—H13A	0.94 (2)
C1—H1A	0.91 (3)	C14—C15	1.521 (3)
C2—C3	1.399 (3)	C14—H14A	0.96 (3)
C2—H2A	0.92 (3)	C14—H14B	0.97 (3)
C3—C4	1.375 (2)	C15—H15A	0.99 (3)
C3—H3A	0.98 (3)	C15—H15B	0.97 (3)
C4—C5	1.409 (2)	C15—H15C	0.91 (3)
C4—H4A	0.91 (3)	C16—C17	1.523 (3)
C5—C6	1.445 (2)	C16—H16A	0.94 (3)
C6—C7	1.350 (2)	C16—H16B	0.94 (2)
C6—H6A	0.95 (2)	C17—H17A	0.97 (3)
C7—C8	1.443 (2)	C17—H17B	0.96 (2)
C7—H7A	0.95 (3)	C17—H17C	0.94 (3)
C8—C9	1.408 (2)	C18—H18A	0.96 (3)
C8—C13	1.410 (2)	C18—H18B	0.94 (3)
C9—C10	1.378 (2)	C18—H18C	0.95 (3)
C1—N1—C5	122.25 (14)	C12—C11—C10	117.06 (14)
C1—N1—C18	117.02 (14)	C13—C12—C11	120.75 (15)
C5—N1—C18	120.72 (14)	C13—C12—H12A	119.0 (15)
C11—N2—C14	122.16 (15)	C11—C12—H12A	120.2 (15)
C11—N2—C16	120.88 (14)	C12—C13—C8	122.16 (14)
C14—N2—C16	116.90 (13)	C12—C13—H13A	120.7 (15)
N1—C1—C2	121.39 (16)	C8—C13—H13A	117.1 (15)
N1—C1—H1A	116.3 (16)	N2—C14—C15	113.93 (15)
C2—C1—H1A	122.2 (16)	N2—C14—H14A	110.1 (15)
C1—C2—C3	117.98 (15)	C15—C14—H14A	110.4 (15)
C1—C2—H2A	120.7 (18)	N2—C14—H14B	107.8 (16)
C3—C2—H2A	121.3 (18)	C15—C14—H14B	109.0 (16)
C4—C3—C2	120.60 (15)	H14A—C14—H14B	105 (2)
C4—C3—H3A	122.5 (17)	C14—C15—H15A	108.9 (18)
C2—C3—H3A	116.9 (17)	C14—C15—H15B	110.5 (17)
C3—C4—C5	120.59 (16)	H15A—C15—H15B	110 (2)
C3—C4—H4A	118.0 (16)	C14—C15—H15C	110.0 (18)
C5—C4—H4A	121.4 (16)	H15A—C15—H15C	109 (2)
N1—C5—C4	117.18 (14)	H15B—C15—H15C	108 (2)
N1—C5—C6	118.99 (14)	N2—C16—C17	112.73 (15)
C4—C5—C6	123.83 (15)	N2—C16—H16A	109.7 (16)
C7—C6—C5	123.55 (15)	C17—C16—H16A	109.9 (16)
C7—C6—H6A	118.6 (15)	N2—C16—H16B	108.7 (16)
C5—C6—H6A	117.8 (15)	C17—C16—H16B	107.1 (16)
C6—C7—C8	125.91 (15)	H16A—C16—H16B	109 (2)
C6—C7—H7A	119.8 (15)	C16—C17—H17A	109.6 (17)
C8—C7—H7A	114.3 (15)	C16—C17—H17B	112.3 (16)
C9—C8—C13	116.92 (14)	H17A—C17—H17B	106 (2)
C9—C8—C7	124.21 (15)	C16—C17—H17C	110.5 (17)
C13—C8—C7	118.86 (14)	H17A—C17—H17C	111 (2)
C10—C9—C8	121.80 (15)	H17B—C17—H17C	107 (2)
C10—C9—H9A	117.3 (14)	N1—C18—H18A	108.7 (16)
C8—C9—H9A	120.8 (14)	N1—C18—H18B	107.8 (18)
C9—C10—C11	121.30 (15)	H18A—C18—H18B	110 (2)
C9—C10—H10A	120.4 (17)	N1—C18—H18C	109.5 (17)
C11—C10—H10A	118.3 (17)	H18A—C18—H18C	110 (2)
N2—C11—C12	121.47 (15)	H18B—C18—H18C	111 (3)
N2—C11—C10	121.47 (15)
C5—N1—C1—C2	0.1 (2)	C7—C8—C9—C10	179.02 (16)
C18—N1—C1—C2	−178.88 (16)	C8—C9—C10—C11	0.0 (3)
N1—C1—C2—C3	1.0 (3)	C14—N2—C11—C12	177.77 (15)
C1—C2—C3—C4	−1.1 (3)	C16—N2—C11—C12	0.6 (2)
C2—C3—C4—C5	0.1 (3)	C14—N2—C11—C10	−2.6 (3)
C1—N1—C5—C4	−1.1 (2)	C16—N2—C11—C10	−179.73 (15)
C18—N1—C5—C4	177.87 (15)	C9—C10—C11—N2	−179.66 (16)
C1—N1—C5—C6	178.99 (15)	C9—C10—C11—C12	0.0 (2)
C18—N1—C5—C6	−2.1 (2)	N2—C11—C12—C13	179.33 (15)
C3—C4—C5—N1	1.0 (2)	C10—C11—C12—C13	−0.3 (2)
C3—C4—C5—C6	−179.10 (16)	C11—C12—C13—C8	0.6 (2)
N1—C5—C6—C7	176.94 (16)	C9—C8—C13—C12	−0.6 (2)
C4—C5—C6—C7	−3.0 (3)	C7—C8—C13—C12	−179.43 (15)
C5—C6—C7—C8	−179.29 (16)	C11—N2—C14—C15	84.7 (2)
C6—C7—C8—C9	−1.4 (3)	C16—N2—C14—C15	−98.03 (19)
C6—C7—C8—C13	177.33 (16)	C11—N2—C16—C17	79.0 (2)
C13—C8—C9—C10	0.3 (2)	C14—N2—C16—C17	−98.24 (18)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···I1i	0.91 (3)	2.99 (3)	3.7980 (18)	148.8 (19)
C18—H18B···Cg2ii	0.94 (3)	2.79 (3)	3.6270 (17)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯I1i	0.91 (3)	2.99 (3)	3.7980 (18)	148.8 (19)
C18—H18B⋯Cg2ii	0.94 (3)	2.79 (3)	3.6270 (17)	149 (3)

Symmetry codes: (i) ; (ii) .