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

In the title compound, C(16)H(18)NO(+)·I(-)·H(2)O, the cation is essentially planar, with a dihedral angle of 3.13 (16)° between the pyridinium and benzene rings. The mol-ecule adopts an E configuration with respect to the alkene double bond. In the crystal structure, the cations are packed in an anti--parallel manner through π-π inter-actions between adjacent pyridinium and benzene rings along the a axis, with centroid-to-centroid distances of 3.615 (2) and 3.630 (2) Å. Water mol-ecules bind the iodide ions through O-H⋯I hydrogen bonds into layers. These layers link with the cations through weak C-H⋯O and C-H⋯I inter-actions.

Related literature

For values of bond lengths, see Allen et al. (1987 ▶). For related structures, see, for example: Chantrapromma et al. (2005 ▶, 2006 ▶); Chantrapromma, Jindawong & Fun (2007 ▶); Chantra­promma, Jindawong, Fun & Patil (2007 ▶); Chantrapromma, Jindawong, Fun, Patil & Karalai (2007 ▶); Jindawong et al. (2005 ▶); Zhang et al. (2000 ▶). For background to nonlinear optics, see, for example: Oudar & Chemla (1977 ▶); Williams (1984 ▶).

Experimental

Crystal data

C16H18NO+·I−·H2O

M = 385.23

Triclinic,

a = 6.9261 (4) Å

b = 10.1857 (6) Å

c = 11.6303 (6) Å

α = 100.829 (2)°

β = 97.399 (2)°

γ = 92.892 (2)°

V = 796.81 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.01 mm−1

T = 100.0 (1) K

0.36 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.528, T max = 0.797

18790 measured reflections

4635 independent reflections

4333 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.14

4635 reflections

184 parameters

H-atom parameters constrained

Δρmax = 2.16 e Å−3

Δρmin = −0.83 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997 ▶); 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/S1600536807061375/sj2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061375/sj2440Isup2.hkl

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

C16H18NO+·I–·H2O	Z = 2
Mr = 385.23	F000 = 384
Triclinic, P1	Dx = 1.606 Mg m−3
Hall symbol: -P 1	Melting point = 481–483 K
a = 6.9261 (4) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.1857 (6) Å	Cell parameters from 4635 reflections
c = 11.6303 (6) Å	θ = 1.8–30.0º
α = 100.829 (2)º	µ = 2.01 mm−1
β = 97.399 (2)º	T = 100.0 (1) K
γ = 92.892 (2)º	Block, yellow
V = 796.81 (8) Å3	0.36 × 0.15 × 0.12 mm

Bruker APEXII CCD area-detector diffractometer	4635 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.8º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.528, Tmax = 0.797	l = −16→16
18790 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0521P)2 + 1.6362P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
4635 reflections	Δρmax = 2.16 e Å−3
184 parameters	Δρmin = −0.83 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem 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	0.46635 (3)	0.14640 (2)	0.24655 (2)	0.02735 (8)
O1	0.1292 (4)	0.6828 (2)	0.0835 (2)	0.0265 (5)
N1	0.3219 (4)	0.2513 (3)	0.6774 (2)	0.0246 (5)
C1	0.3453 (5)	0.2172 (4)	0.7851 (3)	0.0283 (7)
H1A	0.3605	0.1281	0.7900	0.034*
C2	0.3471 (5)	0.3101 (4)	0.8871 (3)	0.0287 (7)
H2A	0.3621	0.2850	0.9604	0.034*
C3	0.3261 (5)	0.4426 (4)	0.8781 (3)	0.0293 (7)
H3A	0.3244	0.5075	0.9458	0.035*
C4	0.3077 (5)	0.4781 (3)	0.7687 (3)	0.0270 (6)
H4A	0.2993	0.5677	0.7632	0.032*
C5	0.3015 (5)	0.3798 (3)	0.6650 (3)	0.0238 (6)
C6	0.2736 (5)	0.4093 (3)	0.5481 (3)	0.0258 (6)
H6A	0.2734	0.3395	0.4837	0.031*
C7	0.2478 (5)	0.5331 (3)	0.5277 (3)	0.0261 (6)
H7A	0.2481	0.6010	0.5935	0.031*
C8	0.2192 (5)	0.5716 (3)	0.4114 (3)	0.0240 (6)
C9	0.2019 (5)	0.7071 (3)	0.4050 (3)	0.0268 (6)
H9A	0.2116	0.7703	0.4749	0.032*
C10	0.1712 (5)	0.7494 (3)	0.2986 (3)	0.0269 (6)
H10A	0.1592	0.8396	0.2969	0.032*
C11	0.1585 (5)	0.6551 (3)	0.1938 (3)	0.0222 (6)
C12	0.1731 (5)	0.5193 (3)	0.1975 (3)	0.0243 (6)
H12A	0.1616	0.4560	0.1275	0.029*
C13	0.2042 (5)	0.4792 (3)	0.3044 (3)	0.0246 (6)
H13A	0.2156	0.3889	0.3057	0.029*
C14	0.1273 (5)	0.8225 (3)	0.0753 (3)	0.0269 (6)
H14A	0.2506	0.8705	0.1130	0.032*
H14B	0.0233	0.8631	0.1145	0.032*
C15	0.0951 (6)	0.8291 (4)	−0.0538 (3)	0.0322 (7)
H15A	0.1122	0.9207	−0.0624	0.048*
H15B	−0.0351	0.7933	−0.0875	0.048*
H15C	0.1875	0.7775	−0.0939	0.048*
C16	0.3131 (6)	0.1419 (3)	0.5723 (3)	0.0306 (7)
H16A	0.4084	0.1630	0.5241	0.046*
H16B	0.1852	0.1326	0.5273	0.046*
H16D	0.3401	0.0594	0.5975	0.046*
O1W	0.9790 (4)	0.0827 (4)	0.3301 (3)	0.0424 (7)
H1W1	0.8765	0.1147	0.3016	0.064*
H2W1	1.0745	0.1130	0.3010	0.064*

	U11	U22	U33	U12	U13	U23
I1	0.02420 (12)	0.01775 (11)	0.03903 (14)	0.00238 (7)	0.00703 (8)	0.00088 (8)
O1	0.0389 (13)	0.0160 (10)	0.0252 (11)	−0.0005 (9)	0.0091 (9)	0.0027 (8)
N1	0.0246 (13)	0.0208 (12)	0.0261 (13)	0.0056 (10)	0.0014 (10)	−0.0005 (10)
C1	0.0253 (15)	0.0303 (17)	0.0294 (16)	0.0034 (13)	0.0053 (12)	0.0052 (13)
C2	0.0282 (16)	0.0319 (17)	0.0259 (15)	0.0016 (13)	0.0069 (12)	0.0037 (13)
C3	0.0275 (16)	0.0299 (17)	0.0289 (16)	−0.0004 (13)	0.0080 (13)	−0.0005 (13)
C4	0.0228 (15)	0.0164 (13)	0.0381 (17)	0.0012 (11)	0.0019 (12)	−0.0019 (12)
C5	0.0202 (13)	0.0215 (14)	0.0286 (15)	0.0041 (11)	0.0014 (11)	0.0025 (12)
C6	0.0291 (16)	0.0233 (15)	0.0249 (14)	0.0042 (12)	0.0036 (12)	0.0042 (12)
C7	0.0277 (15)	0.0236 (15)	0.0266 (15)	−0.0001 (12)	0.0021 (12)	0.0054 (12)
C8	0.0223 (14)	0.0207 (14)	0.0268 (15)	0.0037 (11)	−0.0014 (11)	0.0015 (11)
C9	0.0326 (17)	0.0175 (14)	0.0267 (15)	0.0008 (12)	0.0012 (12)	−0.0027 (11)
C10	0.0360 (17)	0.0137 (13)	0.0294 (15)	−0.0009 (12)	0.0062 (13)	0.0002 (11)
C11	0.0234 (14)	0.0175 (13)	0.0261 (14)	0.0002 (11)	0.0075 (11)	0.0028 (11)
C12	0.0280 (15)	0.0161 (13)	0.0274 (14)	0.0022 (11)	0.0092 (12)	−0.0030 (11)
C13	0.0245 (15)	0.0172 (13)	0.0311 (15)	0.0053 (11)	0.0030 (12)	0.0021 (11)
C14	0.0357 (17)	0.0156 (13)	0.0297 (15)	0.0001 (12)	0.0073 (13)	0.0037 (11)
C15	0.048 (2)	0.0227 (16)	0.0302 (16)	0.0060 (14)	0.0148 (15)	0.0080 (13)
C16	0.042 (2)	0.0209 (15)	0.0265 (15)	0.0068 (14)	0.0019 (14)	−0.0004 (12)
O1W	0.0321 (14)	0.060 (2)	0.0382 (15)	0.0036 (13)	0.0045 (11)	0.0178 (14)

O1—C11	1.357 (4)	C9—C10	1.381 (5)
O1—C14	1.445 (4)	C9—H9A	0.9300
N1—C1	1.353 (4)	C10—C11	1.393 (4)
N1—C5	1.357 (4)	C10—H10A	0.9300
N1—C16	1.483 (4)	C11—C12	1.400 (4)
C1—C2	1.370 (5)	C12—C13	1.374 (5)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.387 (5)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.504 (5)
C3—C4	1.380 (5)	C14—H14A	0.9700
C3—H3A	0.9300	C14—H14B	0.9700
C4—C5	1.410 (5)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.438 (5)	C15—H15C	0.9600
C6—C7	1.342 (5)	C16—H16A	0.9600
C6—H6A	0.9300	C16—H16B	0.9600
C7—C8	1.470 (5)	C16—H16D	0.9600
C7—H7A	0.9300	O1W—H1W1	0.8501
C8—C13	1.401 (5)	O1W—H2W1	0.8500
C8—C9	1.406 (4)
C11—O1—C14	116.9 (3)	C9—C10—C11	119.0 (3)
C1—N1—C5	121.6 (3)	C9—C10—H10A	120.5
C1—N1—C16	117.5 (3)	C11—C10—H10A	120.5
C5—N1—C16	120.8 (3)	O1—C11—C10	125.1 (3)
N1—C1—C2	121.9 (3)	O1—C11—C12	114.9 (3)
N1—C1—H1A	119.1	C10—C11—C12	120.0 (3)
C2—C1—H1A	119.1	C13—C12—C11	120.1 (3)
C1—C2—C3	118.2 (3)	C13—C12—H12A	119.9
C1—C2—H2A	120.9	C11—C12—H12A	119.9
C3—C2—H2A	120.9	C12—C13—C8	121.4 (3)
C4—C3—C2	119.9 (3)	C12—C13—H13A	119.3
C4—C3—H3A	120.0	C8—C13—H13A	119.3
C2—C3—H3A	120.0	O1—C14—C15	107.6 (3)
C3—C4—C5	120.5 (3)	O1—C14—H14A	110.2
C3—C4—H4A	119.7	C15—C14—H14A	110.2
C5—C4—H4A	119.7	O1—C14—H14B	110.2
N1—C5—C4	117.7 (3)	C15—C14—H14B	110.2
N1—C5—C6	119.0 (3)	H14A—C14—H14B	108.5
C4—C5—C6	123.3 (3)	C14—C15—H15A	109.5
C7—C6—C5	122.9 (3)	C14—C15—H15B	109.5
C7—C6—H6A	118.5	H15A—C15—H15B	109.5
C5—C6—H6A	118.5	C14—C15—H15C	109.5
C6—C7—C8	126.3 (3)	H15A—C15—H15C	109.5
C6—C7—H7A	116.9	H15B—C15—H15C	109.5
C8—C7—H7A	116.9	N1—C16—H16A	109.5
C13—C8—C9	117.3 (3)	N1—C16—H16B	109.5
C13—C8—C7	123.3 (3)	H16A—C16—H16B	109.5
C9—C8—C7	119.4 (3)	N1—C16—H16D	109.5
C10—C9—C8	122.3 (3)	H16A—C16—H16D	109.5
C10—C9—H9A	118.9	H16B—C16—H16D	109.5
C8—C9—H9A	118.9	H1W1—O1W—H2W1	107.7
C5—N1—C1—C2	0.8 (5)	C6—C7—C8—C9	−177.4 (4)
C16—N1—C1—C2	−177.3 (3)	C13—C8—C9—C10	0.1 (5)
N1—C1—C2—C3	−0.6 (5)	C7—C8—C9—C10	−178.8 (3)
C1—C2—C3—C4	−1.2 (5)	C8—C9—C10—C11	−0.6 (5)
C2—C3—C4—C5	2.8 (5)	C14—O1—C11—C10	5.3 (5)
C1—N1—C5—C4	0.8 (5)	C14—O1—C11—C12	−175.7 (3)
C16—N1—C5—C4	178.8 (3)	C9—C10—C11—O1	−179.8 (3)
C1—N1—C5—C6	−178.9 (3)	C9—C10—C11—C12	1.2 (5)
C16—N1—C5—C6	−0.8 (5)	O1—C11—C12—C13	179.5 (3)
C3—C4—C5—N1	−2.5 (5)	C10—C11—C12—C13	−1.5 (5)
C3—C4—C5—C6	177.1 (3)	C11—C12—C13—C8	1.0 (5)
N1—C5—C6—C7	178.5 (3)	C9—C8—C13—C12	−0.3 (5)
C4—C5—C6—C7	−1.1 (5)	C7—C8—C13—C12	178.5 (3)
C5—C6—C7—C8	179.8 (3)	C11—O1—C14—C15	179.4 (3)
C6—C7—C8—C13	3.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1	0.85	2.88	3.681 (3)	158
O1W—H2W1···I1i	0.85	2.88	3.690 (3)	159
C16—H16B···O1Wii	0.96	2.49	3.346 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1	0.85	2.88	3.681 (3)	158
O1W—H2W1⋯I1i	0.85	2.88	3.690 (3)	159
C16—H16B⋯O1Wii	0.96	2.49	3.346 (5)	148

Symmetry codes: (i) ; (ii) .