1-Methyl-2-[(E)-2-(2-thien-yl)ethen-yl]quinolinium iodide.

In the title compound, C(16)H(14)NS(+)·I(-), the cation has an E configuration about the C=C double bond of the ethyl-ene unit. The dihedral angle between the thio-phene ring and the quinolinium ring system is 11.67 (11)°. A weak C-H⋯S intra-molecular inter-action involving the thio-phene ring generates an S(5) ring motif. In the crystal structure, the iodide ion, located between the cations arranged in an anti-parallel manner, forms weak C-H⋯I inter-actions. The crystal structure is further stabilized by a π-π inter-action between the thio-phene and pyridine rings; the centroid-centroid distance is 3.6818 (13) Å.

Related literature

For bond lengths, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see, for example: Chantrapromma et al. (2006 ▶, 2008 ▶); Chantrapromma, Jindawong & Fun (2007 ▶); Chantrapromma, Jindawong, Fun & Patil (2007 ▶). For background literature on non-linear optical properties, see, for example: Chou et al. (1996 ▶); Dittrich et al. (2003 ▶); Drost et al. (1995 ▶); Morley (1991 ▶).

Experimental

Crystal data

C16H14NS+·I−

M = 379.25

Triclinic,

a = 7.8243 (1) Å

b = 9.6906 (1) Å

c = 10.7633 (2) Å

α = 97.521 (1)°

β = 95.338 (1)°

γ = 112.758 (1)°

V = 736.82 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.30 mm−1

T = 100.0 (1) K

0.58 × 0.28 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.346, T max = 0.725

17060 measured reflections

4261 independent reflections

4118 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.059

S = 1.10

4261 reflections

173 parameters

H-atom parameters constrained

Δρmax = 1.50 e Å−3

Δρmin = −0.90 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020734/is2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020734/is2311Isup2.hkl

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

C16H14NS+·I–	Z = 2
Mr = 379.25	F000 = 372
Triclinic, P1	Dx = 1.709 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.8243 (1) Å	Cell parameters from 4261 reflections
b = 9.6906 (1) Å	θ = 2.3–30.0º
c = 10.7633 (2) Å	µ = 2.30 mm−1
α = 97.521 (1)º	T = 100.0 (1) K
β = 95.338 (1)º	Block, brown
γ = 112.758 (1)º	0.58 × 0.28 × 0.14 mm
V = 736.817 (18) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4261 independent reflections
Radiation source: fine-focus sealed tube	4118 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.3º
ω scans	h = −11→11
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.346, Tmax = 0.725	l = −15→15
17060 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0282P)2 + 0.8519P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.002
4261 reflections	Δρmax = 1.50 e Å−3
173 parameters	Δρmin = −0.89 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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	0.681003 (17)	0.790360 (14)	0.269777 (12)	0.02186 (5)
S1	0.65928 (8)	0.89200 (6)	0.69144 (6)	0.02828 (11)
N1	0.0896 (2)	0.54762 (17)	0.31586 (15)	0.0162 (3)
C1	−0.0473 (3)	0.4405 (2)	0.21950 (17)	0.0167 (3)
C2	−0.1289 (3)	0.4838 (2)	0.11749 (18)	0.0198 (3)
H2A	−0.0945	0.5863	0.1138	0.024*
C3	−0.2600 (3)	0.3734 (2)	0.02336 (19)	0.0227 (4)
H3A	−0.3128	0.4025	−0.0441	0.027*
C4	−0.3158 (3)	0.2180 (2)	0.02687 (19)	0.0227 (4)
H4A	−0.4034	0.1452	−0.0382	0.027*
C5	−0.2405 (3)	0.1739 (2)	0.12667 (19)	0.0206 (3)
H5A	−0.2781	0.0711	0.1297	0.025*
C6	−0.1062 (3)	0.2843 (2)	0.22486 (18)	0.0180 (3)
C7	−0.0267 (3)	0.2412 (2)	0.32868 (18)	0.0193 (3)
H7A	−0.0686	0.1391	0.3357	0.023*
C8	0.1112 (3)	0.3491 (2)	0.41844 (18)	0.0180 (3)
H8A	0.1644	0.3198	0.4855	0.022*
C9	0.1745 (2)	0.5058 (2)	0.41052 (17)	0.0161 (3)
C10	0.3282 (3)	0.6203 (2)	0.50081 (18)	0.0175 (3)
H10A	0.3838	0.7174	0.4822	0.021*
C11	0.3950 (3)	0.5929 (2)	0.61089 (17)	0.0174 (3)
H11A	0.3399	0.4946	0.6273	0.021*
C12	0.5444 (3)	0.7036 (2)	0.70463 (18)	0.0177 (3)
C13	0.6158 (3)	0.6721 (2)	0.82202 (19)	0.0217 (4)
H13A	0.5752	0.5776	0.8468	0.026*
C14	0.7577 (3)	0.8091 (3)	0.8930 (2)	0.0282 (4)
H14A	0.8203	0.8145	0.9724	0.034*
C15	0.7946 (3)	0.9321 (3)	0.8350 (2)	0.0300 (4)
H15A	0.8850	1.0285	0.8706	0.036*
C16	0.1413 (3)	0.7112 (2)	0.31385 (19)	0.0211 (3)
H16A	0.1810	0.7677	0.3991	0.032*
H16B	0.0345	0.7250	0.2756	0.032*
H16C	0.2418	0.7471	0.2655	0.032*

	U11	U22	U33	U12	U13	U23
I1	0.02044 (7)	0.02041 (7)	0.02481 (7)	0.00758 (5)	0.00089 (5)	0.00842 (5)
S1	0.0287 (3)	0.0207 (2)	0.0312 (3)	0.00775 (19)	−0.0017 (2)	0.00210 (19)
N1	0.0151 (7)	0.0161 (7)	0.0176 (7)	0.0066 (5)	0.0021 (5)	0.0033 (5)
C1	0.0158 (7)	0.0191 (8)	0.0165 (8)	0.0083 (6)	0.0035 (6)	0.0031 (6)
C2	0.0179 (8)	0.0227 (9)	0.0192 (8)	0.0082 (7)	0.0029 (6)	0.0058 (7)
C3	0.0202 (8)	0.0295 (10)	0.0184 (8)	0.0101 (7)	0.0013 (7)	0.0056 (7)
C4	0.0178 (8)	0.0262 (9)	0.0197 (8)	0.0065 (7)	−0.0009 (7)	−0.0006 (7)
C5	0.0188 (8)	0.0193 (8)	0.0213 (8)	0.0068 (7)	0.0007 (7)	−0.0005 (7)
C6	0.0161 (8)	0.0187 (8)	0.0184 (8)	0.0068 (6)	0.0023 (6)	0.0019 (6)
C7	0.0195 (8)	0.0165 (8)	0.0217 (8)	0.0075 (7)	0.0028 (7)	0.0028 (6)
C8	0.0183 (8)	0.0177 (8)	0.0181 (8)	0.0077 (6)	0.0017 (6)	0.0033 (6)
C9	0.0153 (7)	0.0175 (8)	0.0164 (7)	0.0074 (6)	0.0036 (6)	0.0030 (6)
C10	0.0178 (8)	0.0154 (7)	0.0188 (8)	0.0064 (6)	0.0023 (6)	0.0021 (6)
C11	0.0158 (8)	0.0173 (8)	0.0190 (8)	0.0070 (6)	0.0026 (6)	0.0023 (6)
C12	0.0168 (8)	0.0163 (8)	0.0198 (8)	0.0069 (6)	0.0026 (6)	0.0015 (6)
C13	0.0121 (7)	0.0217 (9)	0.0238 (9)	0.0014 (6)	0.0068 (6)	−0.0071 (7)
C14	0.0231 (9)	0.0395 (12)	0.0201 (9)	0.0132 (9)	−0.0010 (7)	0.0002 (8)
C15	0.0263 (10)	0.0248 (10)	0.0295 (11)	0.0056 (8)	−0.0030 (8)	−0.0066 (8)
C16	0.0219 (9)	0.0163 (8)	0.0245 (9)	0.0075 (7)	−0.0003 (7)	0.0051 (7)

S1—C15	1.697 (2)	C7—H7A	0.9300
S1—C12	1.7273 (19)	C8—C9	1.421 (2)
N1—C9	1.354 (2)	C8—H8A	0.9300
N1—C1	1.397 (2)	C9—C10	1.446 (3)
N1—C16	1.481 (2)	C10—C11	1.350 (3)
C1—C2	1.410 (3)	C10—H10A	0.9300
C1—C6	1.413 (3)	C11—C12	1.436 (3)
C2—C3	1.377 (3)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.450 (3)
C3—C4	1.403 (3)	C13—C14	1.420 (3)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.371 (3)	C14—C15	1.361 (4)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.412 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C6—C7	1.415 (3)	C16—H16B	0.9600
C7—C8	1.364 (3)	C16—H16C	0.9600
C15—S1—C12	91.58 (11)	N1—C9—C8	119.08 (16)
C9—N1—C1	121.89 (16)	N1—C9—C10	119.79 (16)
C9—N1—C16	119.57 (16)	C8—C9—C10	121.13 (17)
C1—N1—C16	118.53 (15)	C11—C10—C9	123.13 (17)
N1—C1—C2	121.92 (17)	C11—C10—H10A	118.4
N1—C1—C6	118.98 (16)	C9—C10—H10A	118.4
C2—C1—C6	119.09 (17)	C10—C11—C12	125.11 (17)
C3—C2—C1	119.54 (18)	C10—C11—H11A	117.4
C3—C2—H2A	120.2	C12—C11—H11A	117.4
C1—C2—H2A	120.2	C11—C12—C13	124.49 (17)
C2—C3—C4	121.53 (19)	C11—C12—S1	123.74 (15)
C2—C3—H3A	119.2	C13—C12—S1	111.77 (14)
C4—C3—H3A	119.2	C14—C13—C12	108.83 (19)
C5—C4—C3	119.69 (18)	C14—C13—H13A	125.6
C5—C4—H4A	120.2	C12—C13—H13A	125.6
C3—C4—H4A	120.2	C15—C14—C13	114.4 (2)
C4—C5—C6	120.20 (18)	C15—C14—H14A	122.8
C4—C5—H5A	119.9	C13—C14—H14A	122.8
C6—C5—H5A	119.9	C14—C15—S1	113.38 (17)
C5—C6—C1	119.91 (18)	C14—C15—H15A	123.3
C5—C6—C7	121.09 (17)	S1—C15—H15A	123.3
C1—C6—C7	118.99 (17)	N1—C16—H16A	109.5
C8—C7—C6	120.12 (17)	N1—C16—H16B	109.5
C8—C7—H7A	119.9	H16A—C16—H16B	109.5
C6—C7—H7A	119.9	N1—C16—H16C	109.5
C7—C8—C9	120.69 (18)	H16A—C16—H16C	109.5
C7—C8—H8A	119.7	H16B—C16—H16C	109.5
C9—C8—H8A	119.7
C9—N1—C1—C2	−176.75 (17)	C1—N1—C9—C8	−5.6 (3)
C16—N1—C1—C2	3.6 (3)	C16—N1—C9—C8	173.99 (16)
C9—N1—C1—C6	3.5 (3)	C1—N1—C9—C10	173.83 (16)
C16—N1—C1—C6	−176.05 (16)	C16—N1—C9—C10	−6.6 (2)
N1—C1—C2—C3	178.41 (17)	C7—C8—C9—N1	3.2 (3)
C6—C1—C2—C3	−1.9 (3)	C7—C8—C9—C10	−176.23 (17)
C1—C2—C3—C4	0.5 (3)	N1—C9—C10—C11	166.39 (17)
C2—C3—C4—C5	0.8 (3)	C8—C9—C10—C11	−14.2 (3)
C3—C4—C5—C6	−0.6 (3)	C9—C10—C11—C12	−178.56 (17)
C4—C5—C6—C1	−0.8 (3)	C10—C11—C12—C13	−179.42 (18)
C4—C5—C6—C7	−179.96 (18)	C10—C11—C12—S1	1.4 (3)
N1—C1—C6—C5	−178.25 (16)	C15—S1—C12—C11	178.33 (17)
C2—C1—C6—C5	2.0 (3)	C15—S1—C12—C13	−0.98 (15)
N1—C1—C6—C7	0.9 (3)	C11—C12—C13—C14	−177.85 (18)
C2—C1—C6—C7	−178.77 (17)	S1—C12—C13—C14	1.5 (2)
C5—C6—C7—C8	175.96 (18)	C12—C13—C14—C15	−1.3 (3)
C1—C6—C7—C8	−3.2 (3)	C13—C14—C15—S1	0.6 (3)
C6—C7—C8—C9	1.2 (3)	C12—S1—C15—C14	0.22 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···S1	0.93	2.80	3.189 (2)	106
C11—H11A···I1i	0.93	3.06	3.934 (2)	157
C16—H16B···I1ii	0.96	3.06	3.962 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯S1	0.93	2.80	3.189 (2)	106
C11—H11A⋯I1i	0.93	3.06	3.934 (2)	157
C16—H16B⋯I1ii	0.96	3.06	3.962 (2)	156

Symmetry codes: (i) ; (ii) .