(E)-1-Methyl-4-styrylpyridinium iodide monohydrate.

In the title compound, C(14)H(14)N(+)·I(-)·H(2)O, the cation is essentially planar, with a dihedral angle of 2.55 (7)° between the pyridinium and phenyl rings, and exists in an E configuration with respect to the ethenyl bond. In the crystal structure, the cations are stacked in an anti-parallel manner along the a axis. The cation is linked to the water mol-ecule by a weak C-H⋯O inter-action, and the water mol-ecule is further linked to the I(-) ion by O-H⋯I hydrogen bonds. The crystal structure is consolidated by these inter-actions and is further stabilized by a π-π inter-action between the pyridinium and phenyl rings with a centroid-centroid distance of 3.6850 (8) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to non-linear optical materials research, see: Chemla & Zyss (1987 ▶); Chia et al. (1995 ▶); Dittrich et al. (2003 ▶); Lin et al. (2002 ▶); Prasad & Williams (1991 ▶). For related structures, see: Chanawanno et al. (2008 ▶); Chantrapromma, Jindawong & Fun (2007 ▶); Chantrapromma, Jindawong, Fun & Patil (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H14N+·I−·H2O

M = 341.18

Monoclinic,

a = 7.3636 (1) Å

b = 10.5929 (1) Å

c = 18.2807 (2) Å

β = 106.770 (1)°

V = 1365.29 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.33 mm−1

T = 100 K

0.32 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.524, T max = 0.649

27548 measured reflections

6004 independent reflections

5307 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.058

S = 1.05

6004 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.32 e Å−3

Δρmin = −0.56 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/S1600536809040446/is2467sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040446/is2467Isup2.hkl

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

C14H14N+·I−·H2O	F(000) = 672
Mr = 341.18	Dx = 1.660 Mg m−3
Monoclinic, P21/c	Melting point = 489–490 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.3636 (1) Å	Cell parameters from 6004 reflections
b = 10.5929 (1) Å	θ = 2.3–35.0°
c = 18.2807 (2) Å	µ = 2.33 mm−1
β = 106.770 (1)°	T = 100 K
V = 1365.29 (3) Å3	Block, yellow
Z = 4	0.32 × 0.22 × 0.20 mm

Bruker APEXII CCD area-detector diffractometer	6004 independent reflections
Radiation source: sealed tube	5307 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 35.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.524, Tmax = 0.649	k = −17→16
27548 measured reflections	l = −29→28

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0248P)2 + 0.8184P] where P = (Fo2 + 2Fc2)/3
6004 reflections	(Δ/σ)max = 0.004
163 parameters	Δρmax = 1.32 e Å−3
0 restraints	Δρmin = −0.56 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	0.742589 (15)	0.831113 (9)	0.885210 (5)	0.02548 (3)
O1W	0.20711 (19)	0.98174 (12)	0.94686 (7)	0.0308 (2)
H1W1	0.086 (4)	0.944 (3)	0.9327 (16)	0.060 (8)*
H2W1	0.210 (4)	1.028 (2)	0.9901 (15)	0.048 (7)*
N1	0.53960 (16)	0.74866 (11)	1.12888 (6)	0.01776 (19)
C1	0.3622 (2)	0.68934 (13)	1.00380 (8)	0.0219 (2)
H1A	0.3146	0.7096	0.9523	0.026*
C2	0.4699 (2)	0.77624 (13)	1.05393 (8)	0.0218 (2)
H2A	0.4948	0.8546	1.0360	0.026*
C3	0.5064 (2)	0.63509 (12)	1.15607 (7)	0.0185 (2)
H3A	0.5556	0.6174	1.2079	0.022*
C4	0.4006 (2)	0.54563 (12)	1.10806 (7)	0.0187 (2)
H4A	0.3796	0.4676	1.1275	0.022*
C5	0.32393 (19)	0.57076 (12)	1.02979 (7)	0.0176 (2)
C6	0.2111 (2)	0.47325 (12)	0.98062 (7)	0.0191 (2)
H6A	0.1960	0.3967	1.0031	0.023*
C7	0.12773 (19)	0.48617 (12)	0.90531 (7)	0.0188 (2)
H7A	0.1434	0.5629	0.8832	0.023*
C8	0.01415 (19)	0.38969 (12)	0.85514 (7)	0.0175 (2)
C9	−0.0249 (2)	0.27106 (12)	0.88126 (8)	0.0195 (2)
H9A	0.0259	0.2496	0.9324	0.023*
C10	−0.1394 (2)	0.18542 (12)	0.83081 (9)	0.0214 (2)
H10A	−0.1634	0.1065	0.8482	0.026*
C11	−0.2182 (2)	0.21752 (13)	0.75423 (8)	0.0214 (2)
H11A	−0.2975	0.1609	0.7210	0.026*
C12	−0.1783 (2)	0.33396 (13)	0.72750 (8)	0.0226 (2)
H12A	−0.2297	0.3551	0.6763	0.027*
C13	−0.0616 (2)	0.41849 (13)	0.77750 (8)	0.0206 (2)
H13A	−0.0331	0.4956	0.7592	0.025*
C14	0.6473 (2)	0.84639 (13)	1.18135 (8)	0.0234 (3)
H14A	0.7349	0.8866	1.1588	0.035*
H14B	0.7160	0.8079	1.2288	0.035*
H14C	0.5611	0.9082	1.1906	0.035*

	U11	U22	U33	U12	U13	U23
I1	0.03493 (6)	0.02076 (4)	0.01682 (4)	−0.00883 (3)	0.00120 (3)	0.00305 (3)
O1W	0.0324 (6)	0.0315 (6)	0.0294 (5)	0.0025 (5)	0.0103 (5)	−0.0004 (4)
N1	0.0178 (5)	0.0184 (4)	0.0172 (4)	−0.0012 (4)	0.0054 (4)	−0.0003 (3)
C1	0.0249 (7)	0.0220 (6)	0.0176 (5)	−0.0017 (5)	0.0043 (5)	0.0029 (4)
C2	0.0247 (7)	0.0209 (6)	0.0199 (5)	−0.0022 (5)	0.0065 (5)	0.0038 (4)
C3	0.0203 (6)	0.0177 (5)	0.0183 (5)	0.0011 (4)	0.0068 (4)	0.0015 (4)
C4	0.0207 (6)	0.0174 (5)	0.0191 (5)	0.0005 (4)	0.0074 (4)	0.0018 (4)
C5	0.0166 (5)	0.0181 (5)	0.0182 (5)	0.0008 (4)	0.0055 (4)	0.0011 (4)
C6	0.0202 (6)	0.0177 (5)	0.0194 (5)	0.0002 (4)	0.0060 (4)	0.0017 (4)
C7	0.0193 (6)	0.0181 (5)	0.0192 (5)	0.0008 (4)	0.0058 (4)	0.0025 (4)
C8	0.0159 (5)	0.0178 (5)	0.0188 (5)	0.0006 (4)	0.0051 (4)	0.0005 (4)
C9	0.0186 (6)	0.0181 (5)	0.0212 (5)	0.0024 (4)	0.0049 (4)	0.0033 (4)
C10	0.0207 (6)	0.0158 (5)	0.0281 (6)	0.0012 (4)	0.0077 (5)	0.0023 (4)
C11	0.0198 (6)	0.0208 (6)	0.0238 (6)	−0.0012 (5)	0.0068 (5)	−0.0047 (4)
C12	0.0243 (7)	0.0251 (6)	0.0178 (5)	−0.0005 (5)	0.0054 (5)	0.0005 (4)
C13	0.0212 (6)	0.0207 (5)	0.0200 (5)	−0.0015 (5)	0.0064 (5)	0.0026 (4)
C14	0.0248 (7)	0.0228 (6)	0.0224 (6)	−0.0050 (5)	0.0065 (5)	−0.0044 (4)

O1W—H1W1	0.94 (3)	C7—C8	1.4637 (18)
O1W—H2W1	0.93 (3)	C7—H7A	0.9300
N1—C2	1.3491 (17)	C8—C13	1.4005 (18)
N1—C3	1.3507 (17)	C8—C9	1.4032 (19)
N1—C14	1.4772 (18)	C9—C10	1.391 (2)
C1—C2	1.377 (2)	C9—H9A	0.9300
C1—C5	1.4003 (19)	C10—C11	1.394 (2)
C1—H1A	0.9300	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.389 (2)
C3—C4	1.3711 (19)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.387 (2)
C4—C5	1.4039 (18)	C12—H12A	0.9300
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.4608 (19)	C14—H14A	0.9600
C6—C7	1.3429 (18)	C14—H14B	0.9600
C6—H6A	0.9300	C14—H14C	0.9600
H1W1—O1W—H2W1	104 (2)	C13—C8—C9	118.63 (12)
C2—N1—C3	120.69 (12)	C13—C8—C7	118.12 (12)
C2—N1—C14	118.90 (12)	C9—C8—C7	123.24 (11)
C3—N1—C14	120.37 (11)	C10—C9—C8	120.19 (12)
C2—C1—C5	120.49 (12)	C10—C9—H9A	119.9
C2—C1—H1A	119.8	C8—C9—H9A	119.9
C5—C1—H1A	119.8	C9—C10—C11	120.24 (12)
N1—C2—C1	120.55 (12)	C9—C10—H10A	119.9
N1—C2—H2A	119.7	C11—C10—H10A	119.9
C1—C2—H2A	119.7	C12—C11—C10	120.06 (13)
N1—C3—C4	120.65 (12)	C12—C11—H11A	120.0
N1—C3—H3A	119.7	C10—C11—H11A	120.0
C4—C3—H3A	119.7	C13—C12—C11	119.69 (13)
C3—C4—C5	120.56 (12)	C13—C12—H12A	120.2
C3—C4—H4A	119.7	C11—C12—H12A	120.2
C5—C4—H4A	119.7	C12—C13—C8	121.14 (12)
C1—C5—C4	117.05 (12)	C12—C13—H13A	119.4
C1—C5—C6	124.05 (12)	C8—C13—H13A	119.4
C4—C5—C6	118.90 (12)	N1—C14—H14A	109.5
C7—C6—C5	124.71 (12)	N1—C14—H14B	109.5
C7—C6—H6A	117.6	H14A—C14—H14B	109.5
C5—C6—H6A	117.6	N1—C14—H14C	109.5
C6—C7—C8	125.51 (12)	H14A—C14—H14C	109.5
C6—C7—H7A	117.2	H14B—C14—H14C	109.5
C8—C7—H7A	117.2
C3—N1—C2—C1	0.5 (2)	C5—C6—C7—C8	−179.95 (13)
C14—N1—C2—C1	−177.34 (14)	C6—C7—C8—C13	−179.47 (14)
C5—C1—C2—N1	−0.2 (2)	C6—C7—C8—C9	1.6 (2)
C2—N1—C3—C4	−0.2 (2)	C13—C8—C9—C10	−1.1 (2)
C14—N1—C3—C4	177.64 (13)	C7—C8—C9—C10	177.78 (13)
N1—C3—C4—C5	−0.4 (2)	C8—C9—C10—C11	−0.9 (2)
C2—C1—C5—C4	−0.3 (2)	C9—C10—C11—C12	1.8 (2)
C2—C1—C5—C6	179.97 (14)	C10—C11—C12—C13	−0.7 (2)
C3—C4—C5—C1	0.7 (2)	C11—C12—C13—C8	−1.3 (2)
C3—C4—C5—C6	−179.63 (13)	C9—C8—C13—C12	2.2 (2)
C1—C5—C6—C7	−1.4 (2)	C7—C8—C13—C12	−176.72 (13)
C4—C5—C6—C7	178.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1i	0.94 (3)	2.70 (3)	3.6458 (14)	177 (3)
O1W—H2W1···I1ii	0.93 (3)	2.66 (2)	3.5826 (12)	174 (2)
C14—H14A···O1Wii	0.96	2.52	3.3775 (19)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1i	0.94 (3)	2.70 (3)	3.6458 (14)	177 (3)
O1W—H2W1⋯I1ii	0.93 (3)	2.66 (2)	3.5826 (12)	174 (2)
C14—H14A⋯O1Wii	0.96	2.52	3.3775 (19)	149

Symmetry codes: (i) ; (ii) .