2-[(E)-2-(4-Meth-oxy-phen-yl)ethen-yl]-1-methyl-pyridinium iodide.

In the title mol-ecular salt, C16H10NO(+)·I(-), the dihedral angle between the pyridinium and benzene rings is 6.61 (8)°. In the crystal, the cation is linked to the anion by a C-H⋯I inter-action arising from the activated aromatic C atom adjacent to the N(+) cation.

Related literature

For background to organic non-linear optical materials, see: Jagannathan et al. (2007 ▶); Williams (1984 ▶). For a related structure, see: Chantrapromma et al. (2010 ▶).

Experimental

Crystal data

C15H16NO+·I−

M = 353.19

Triclinic,

a = 7.1760 (3) Å

b = 8.6895 (4) Å

c = 12.1555 (6) Å

α = 92.645 (2)°

β = 92.115 (2)°

γ = 103.781 (2)°

V = 734.47 (6) Å3

Z = 2

Mo Kα radiation

μ = 2.17 mm−1

T = 298 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.613, T max = 0.737

8523 measured reflections

2470 independent reflections

2363 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.052

S = 1.09

2470 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031929/hb7162sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031929/hb7162Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031929/hb7162Isup3.cml

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

C15H16NO+·I−	Z = 2
Mr = 353.19	F(000) = 348
Triclinic, P1	Dx = 1.597 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1760 (3) Å	Cell parameters from 8234 reflections
b = 8.6895 (4) Å	θ = 2.4–28.4°
c = 12.1555 (6) Å	µ = 2.17 mm−1
α = 92.645 (2)°	T = 298 K
β = 92.115 (2)°	Slab, yellow
γ = 103.781 (2)°	0.25 × 0.20 × 0.15 mm
V = 734.47 (6) Å3

Bruker APEXII CCD diffractometer	2470 independent reflections
Radiation source: fine-focus sealed tube	2363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→6
Tmin = 0.613, Tmax = 0.737	k = −10→10
8523 measured reflections	l = −12→14

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)] = 0.020	H-atom parameters constrained
wR(F2) = 0.052	w = 1/[σ2(Fo2) + (0.0211P)2 + 0.414P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2470 reflections	Δρmax = 0.31 e Å−3
165 parameters	Δρmin = −0.59 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0288 (14)

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
C1	−0.1445 (4)	0.0480 (3)	0.8878 (2)	0.0494 (6)
H1	−0.2582	−0.0296	0.8742	0.059*
C2	−0.1376 (4)	0.1673 (3)	0.9651 (2)	0.0560 (7)
H2	−0.2451	0.1722	1.0043	0.067*
C3	0.0321 (5)	0.2809 (3)	0.9843 (2)	0.0598 (7)
H3	0.0397	0.3633	1.0372	0.072*
C4	0.1896 (4)	0.2736 (3)	0.9260 (2)	0.0537 (6)
H4	0.3039	0.3503	0.9400	0.064*
C5	0.1799 (4)	0.1513 (3)	0.84555 (19)	0.0419 (5)
C6	0.3386 (4)	0.1382 (3)	0.7790 (2)	0.0468 (6)
H6	0.3297	0.0432	0.7383	0.056*
C7	0.4961 (4)	0.2531 (3)	0.7722 (2)	0.0460 (5)
H7	0.5055	0.3449	0.8167	0.055*
C8	0.6550 (3)	0.2503 (3)	0.7027 (2)	0.0422 (5)
C9	0.8189 (4)	0.3743 (3)	0.7121 (2)	0.0497 (6)
H9	0.8233	0.4583	0.7632	0.060*
C10	0.9754 (4)	0.3779 (3)	0.6488 (2)	0.0497 (6)
H10	1.0838	0.4618	0.6580	0.060*
C11	0.9687 (4)	0.2554 (3)	0.5718 (2)	0.0497 (6)
C13	0.8062 (4)	0.1296 (3)	0.5607 (3)	0.0622 (7)
H13	0.8019	0.0465	0.5088	0.075*
C14	0.6536 (4)	0.1264 (3)	0.6246 (2)	0.0549 (6)
H14	0.5470	0.0408	0.6163	0.066*
C15	1.2825 (4)	0.3695 (4)	0.5113 (3)	0.0652 (8)
H15A	1.2501	0.4670	0.4943	0.098*
H15B	1.3708	0.3459	0.4594	0.098*
H15C	1.3410	0.3800	0.5845	0.098*
C16	−0.0104 (4)	−0.0956 (3)	0.7487 (2)	0.0561 (7)
H16A	−0.1383	−0.1617	0.7491	0.084*
H16B	0.0805	−0.1563	0.7676	0.084*
H16C	0.0128	−0.0567	0.6766	0.084*
N1	0.0107 (3)	0.0400 (2)	0.83019 (16)	0.0409 (4)
O1	1.1126 (3)	0.2441 (3)	0.50511 (19)	0.0726 (6)
I1	0.43035 (2)	0.689767 (18)	0.803640 (16)	0.05847 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (13)	0.0580 (14)	0.0471 (14)	0.0149 (11)	0.0023 (11)	0.0090 (11)
C2	0.0638 (17)	0.0679 (16)	0.0428 (14)	0.0267 (14)	0.0105 (12)	0.0086 (12)
C3	0.085 (2)	0.0533 (15)	0.0434 (14)	0.0208 (14)	0.0134 (14)	0.0002 (11)
C4	0.0653 (16)	0.0454 (13)	0.0461 (14)	0.0048 (12)	0.0071 (12)	0.0004 (11)
C5	0.0502 (13)	0.0407 (11)	0.0355 (12)	0.0111 (10)	0.0015 (10)	0.0082 (9)
C6	0.0512 (14)	0.0437 (12)	0.0445 (13)	0.0096 (11)	0.0032 (11)	−0.0003 (10)
C7	0.0524 (14)	0.0402 (12)	0.0460 (14)	0.0123 (10)	0.0012 (11)	0.0025 (10)
C8	0.0435 (12)	0.0410 (11)	0.0425 (13)	0.0114 (10)	−0.0032 (10)	0.0045 (9)
C9	0.0563 (15)	0.0415 (12)	0.0475 (14)	0.0053 (11)	0.0016 (12)	−0.0025 (10)
C10	0.0460 (13)	0.0471 (13)	0.0510 (15)	0.0022 (10)	−0.0012 (11)	0.0014 (11)
C11	0.0401 (13)	0.0570 (14)	0.0507 (15)	0.0100 (11)	−0.0010 (11)	−0.0012 (11)
C13	0.0506 (15)	0.0616 (16)	0.0677 (19)	0.0053 (13)	0.0024 (13)	−0.0226 (14)
C14	0.0422 (13)	0.0537 (14)	0.0620 (17)	0.0012 (11)	−0.0002 (12)	−0.0104 (12)
C15	0.0443 (15)	0.0802 (19)	0.0671 (19)	0.0053 (14)	0.0059 (13)	0.0111 (15)
C16	0.0487 (14)	0.0548 (14)	0.0596 (17)	0.0057 (12)	0.0012 (12)	−0.0122 (12)
N1	0.0442 (11)	0.0444 (10)	0.0349 (10)	0.0125 (8)	−0.0016 (8)	0.0045 (8)
O1	0.0491 (11)	0.0816 (14)	0.0795 (15)	0.0041 (10)	0.0153 (10)	−0.0219 (11)
I1	0.04875 (13)	0.04564 (12)	0.07815 (17)	0.00721 (8)	0.00877 (9)	−0.00920 (8)

C1—N1	1.351 (3)	C9—C10	1.380 (4)
C1—C2	1.357 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.375 (4)
C2—C3	1.377 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—O1	1.355 (3)
C3—C4	1.369 (4)	C11—C13	1.393 (4)
C3—H3	0.9300	C13—C14	1.362 (4)
C4—C5	1.397 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—N1	1.361 (3)	C15—O1	1.426 (3)
C5—C6	1.445 (3)	C15—H15A	0.9600
C6—C7	1.326 (4)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.448 (4)	C16—N1	1.479 (3)
C7—H7	0.9300	C16—H16A	0.9600
C8—C9	1.390 (3)	C16—H16B	0.9600
C8—C14	1.400 (4)	C16—H16C	0.9600
N1—C1—C2	121.2 (2)	C11—C10—H10	120.5
N1—C1—H1	119.4	C9—C10—H10	120.5
C2—C1—H1	119.4	O1—C11—C10	124.9 (2)
C1—C2—C3	118.6 (3)	O1—C11—C13	115.6 (2)
C1—C2—H2	120.7	C10—C11—C13	119.5 (2)
C3—C2—H2	120.7	C14—C13—C11	121.0 (3)
C4—C3—C2	120.5 (3)	C14—C13—H13	119.5
C4—C3—H3	119.8	C11—C13—H13	119.5
C2—C3—H3	119.8	C13—C14—C8	120.9 (2)
C3—C4—C5	120.4 (3)	C13—C14—H14	119.6
C3—C4—H4	119.8	C8—C14—H14	119.6
C5—C4—H4	119.8	O1—C15—H15A	109.5
N1—C5—C4	117.4 (2)	O1—C15—H15B	109.5
N1—C5—C6	119.1 (2)	H15A—C15—H15B	109.5
C4—C5—C6	123.5 (2)	O1—C15—H15C	109.5
C7—C6—C5	124.1 (2)	H15A—C15—H15C	109.5
C7—C6—H6	117.9	H15B—C15—H15C	109.5
C5—C6—H6	117.9	N1—C16—H16A	109.5
C6—C7—C8	126.7 (2)	N1—C16—H16B	109.5
C6—C7—H7	116.6	H16A—C16—H16B	109.5
C8—C7—H7	116.6	N1—C16—H16C	109.5
C9—C8—C14	117.0 (2)	H16A—C16—H16C	109.5
C9—C8—C7	120.0 (2)	H16B—C16—H16C	109.5
C14—C8—C7	123.0 (2)	C1—N1—C5	121.9 (2)
C10—C9—C8	122.7 (2)	C1—N1—C16	117.2 (2)
C10—C9—H9	118.7	C5—N1—C16	120.9 (2)
C8—C9—H9	118.7	C11—O1—C15	118.6 (2)
C11—C10—C9	119.0 (2)
N1—C1—C2—C3	−0.2 (4)	C9—C10—C11—C13	−1.1 (4)
C1—C2—C3—C4	0.3 (4)	O1—C11—C13—C14	178.9 (3)
C2—C3—C4—C5	0.6 (4)	C10—C11—C13—C14	0.2 (5)
C3—C4—C5—N1	−1.5 (4)	C11—C13—C14—C8	0.6 (5)
C3—C4—C5—C6	178.4 (2)	C9—C8—C14—C13	−0.6 (4)
N1—C5—C6—C7	167.1 (2)	C7—C8—C14—C13	179.6 (3)
C4—C5—C6—C7	−12.8 (4)	C2—C1—N1—C5	−0.9 (4)
C5—C6—C7—C8	−176.5 (2)	C2—C1—N1—C16	179.3 (2)
C6—C7—C8—C9	−174.0 (3)	C4—C5—N1—C1	1.7 (3)
C6—C7—C8—C14	5.8 (4)	C6—C5—N1—C1	−178.2 (2)
C14—C8—C9—C10	−0.2 (4)	C4—C5—N1—C16	−178.4 (2)
C7—C8—C9—C10	179.5 (2)	C6—C5—N1—C16	1.6 (3)
C8—C9—C10—C11	1.1 (4)	C10—C11—O1—C15	−2.1 (4)
C9—C10—C11—O1	−179.6 (3)	C13—C11—O1—C15	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···I1i	0.93	2.96	3.872 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯I1i	0.93	2.96	3.872 (3)	168

Symmetry code: (i) .