2-[(E)-2-(4-Chloro-phen-yl)ethen-yl]-1-methylpyridinium iodide monohydrate.

In the title compound, C(14)H(13)ClN(+)·I(-)·H(2)O, the cation is nearly planar and exists in an E configuration; the dihedral angle between the pyridinium and benzene rings is 0.98 (17)°. The cations stack in an anti-parallel manner along the a axis through two π-π inter-actions between the pyridinium and benzene rings [centroid-centroid distances 3.569 (2) and 3.6818 (13) Å, respectively]. The cation, anion and water mol-ecule are linked into a chain along the a axis by weak C-H⋯O and C-H⋯I inter-actions together with O-H⋯I hydrogen bonds and the chains are further connected into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Chantrapromma et al. (2007a ▶,b ▶,c ▶). For background on non-linear optical properties, see, for example: Lakshmanaperumal et al. (2004 ▶); Marder et al. (1994 ▶); Qiu et al. (2007 ▶); Williams (1984 ▶); Zhai et al. (1999 ▶); Zhan et al. (2006 ▶).

Experimental

Crystal data

C14H13ClN+·I−·H2O

M = 375.62

Monoclinic,

a = 7.0876 (1) Å

b = 9.8096 (2) Å

c = 21.0940 (4) Å

β = 95.147 (1)°

V = 1460.68 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.36 mm−1

T = 100.0 (1) K

0.28 × 0.17 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.560, T max = 0.845

18928 measured reflections

4241 independent reflections

3486 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.13

4241 reflections

164 parameters

H-atom parameters constrained

Δρmax = 2.13 e Å−3

Δρmin = −0.79 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/S1600536808027724/is2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027724/is2329Isup2.hkl

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

C14H13ClN+·I−·H2O	F(000) = 736
Mr = 375.62	Dx = 1.708 Mg m−3
Monoclinic, P21/c	Melting point: 492-493 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0876 (1) Å	Cell parameters from 4241 reflections
b = 9.8096 (2) Å	θ = 1.9–30.0°
c = 21.0940 (4) Å	µ = 2.36 mm−1
β = 95.147 (1)°	T = 100 K
V = 1460.68 (5) Å3	Plate, orange
Z = 4	0.28 × 0.17 × 0.07 mm

Bruker SMART APEXII CCD area-detector diffractometer	4241 independent reflections
Radiation source: fine-focus sealed tube	3486 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 1.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→12
Tmin = 0.561, Tmax = 0.845	l = −26→29
18928 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0483P)2 + 1.1431P] where P = (Fo2 + 2Fc2)/3
4241 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 2.13 e Å−3
0 restraints	Δρmin = −0.79 e Å−3

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	0.96440 (3)	0.30947 (2)	0.374487 (10)	0.02517 (9)
Cl1	0.65015 (14)	−0.33018 (11)	0.25791 (5)	0.0349 (2)
N1	0.7517 (4)	0.2927 (3)	0.58820 (14)	0.0228 (6)
O1W	0.4685 (5)	0.3289 (4)	0.39663 (18)	0.0589 (10)
H1W1	0.5617	0.2949	0.3782	0.088*
H2W1	0.3691	0.2881	0.3808	0.088*
C1	0.7754 (5)	0.3535 (4)	0.64637 (17)	0.0254 (7)
H1A	0.7521	0.4464	0.6498	0.030*
C2	0.8329 (5)	0.2805 (4)	0.69966 (18)	0.0277 (8)
H2A	0.8473	0.3228	0.7393	0.033*
C3	0.8698 (5)	0.1412 (4)	0.69383 (17)	0.0262 (7)
H3A	0.9115	0.0900	0.7294	0.031*
C4	0.8440 (5)	0.0817 (4)	0.63559 (17)	0.0264 (7)
H4A	0.8674	−0.0111	0.6318	0.032*
C5	0.7828 (5)	0.1569 (4)	0.58078 (17)	0.0221 (7)
C6	0.7492 (5)	0.0969 (4)	0.51828 (17)	0.0256 (7)
H6A	0.7187	0.1548	0.4839	0.031*
C7	0.7592 (5)	−0.0353 (4)	0.50694 (17)	0.0268 (7)
H7A	0.7883	−0.0912	0.5421	0.032*
C8	0.7293 (5)	−0.1035 (4)	0.44465 (16)	0.0235 (7)
C9	0.7663 (5)	−0.2435 (4)	0.44164 (18)	0.0266 (7)
H9A	0.8075	−0.2903	0.4786	0.032*
C10	0.7425 (5)	−0.3135 (4)	0.38414 (19)	0.0271 (8)
H10A	0.7680	−0.4063	0.3824	0.033*
C11	0.6808 (5)	−0.2432 (4)	0.33021 (17)	0.0238 (7)
C12	0.6421 (5)	−0.1050 (4)	0.33059 (17)	0.0258 (7)
H12A	0.6005	−0.0596	0.2932	0.031*
C13	0.6668 (5)	−0.0354 (4)	0.38847 (17)	0.0250 (7)
H13A	0.6414	0.0575	0.3896	0.030*
C14	0.6940 (5)	0.3805 (4)	0.53292 (18)	0.0298 (8)
H14D	0.6802	0.4727	0.5470	0.045*
H14A	0.5754	0.3489	0.5126	0.045*
H14B	0.7889	0.3769	0.5032	0.045*

	U11	U22	U33	U12	U13	U23
I1	0.02744 (14)	0.02228 (14)	0.02596 (14)	0.00264 (9)	0.00324 (9)	0.00111 (9)
Cl1	0.0368 (5)	0.0385 (6)	0.0293 (5)	−0.0051 (4)	0.0027 (4)	−0.0126 (4)
N1	0.0206 (13)	0.0229 (16)	0.0249 (15)	0.0010 (11)	0.0027 (11)	0.0046 (12)
O1W	0.0347 (17)	0.083 (3)	0.058 (2)	0.0104 (16)	−0.0028 (15)	−0.028 (2)
C1	0.0246 (17)	0.0238 (18)	0.0278 (18)	0.0003 (14)	0.0028 (14)	0.0000 (15)
C2	0.0255 (17)	0.032 (2)	0.0261 (18)	−0.0004 (14)	0.0028 (14)	−0.0020 (15)
C3	0.0209 (16)	0.031 (2)	0.0263 (17)	0.0017 (14)	−0.0021 (13)	0.0030 (15)
C4	0.0218 (16)	0.0267 (19)	0.0307 (18)	−0.0010 (14)	0.0017 (14)	0.0034 (15)
C5	0.0175 (15)	0.0230 (18)	0.0265 (17)	−0.0009 (12)	0.0050 (12)	−0.0007 (14)
C6	0.0265 (17)	0.0245 (19)	0.0258 (17)	0.0002 (14)	0.0018 (14)	0.0001 (14)
C7	0.0272 (17)	0.0261 (19)	0.0268 (18)	0.0021 (14)	0.0002 (14)	−0.0019 (15)
C8	0.0227 (16)	0.0244 (19)	0.0236 (16)	−0.0012 (13)	0.0027 (13)	−0.0021 (14)
C9	0.0288 (18)	0.0231 (19)	0.0272 (18)	0.0000 (14)	−0.0009 (14)	0.0014 (15)
C10	0.0266 (17)	0.0195 (18)	0.035 (2)	−0.0016 (14)	0.0038 (15)	0.0009 (15)
C11	0.0203 (16)	0.0253 (19)	0.0257 (17)	−0.0029 (13)	0.0025 (13)	−0.0064 (14)
C12	0.0233 (16)	0.027 (2)	0.0267 (17)	0.0026 (14)	−0.0011 (13)	0.0029 (14)
C13	0.0246 (16)	0.0172 (17)	0.0329 (19)	0.0022 (13)	0.0013 (14)	0.0009 (14)
C14	0.037 (2)	0.025 (2)	0.0281 (18)	0.0052 (15)	0.0056 (15)	0.0032 (15)

Cl1—C11	1.744 (4)	C6—H6A	0.9300
N1—C1	1.361 (5)	C7—C8	1.473 (5)
N1—C5	1.361 (5)	C7—H7A	0.9300
N1—C14	1.478 (5)	C8—C13	1.397 (5)
O1W—H1W1	0.8628	C8—C9	1.400 (5)
O1W—H2W1	0.8523	C9—C10	1.391 (5)
C1—C2	1.364 (5)	C9—H9A	0.9300
C1—H1A	0.9300	C10—C11	1.368 (5)
C2—C3	1.399 (6)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.383 (5)
C3—C4	1.358 (5)	C12—C13	1.396 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.407 (5)	C13—H13A	0.9300
C4—H4A	0.9300	C14—H14D	0.9600
C5—C6	1.444 (5)	C14—H14A	0.9600
C6—C7	1.322 (5)	C14—H14B	0.9600
C1—N1—C5	121.6 (3)	C13—C8—C9	118.5 (3)
C1—N1—C14	117.3 (3)	C13—C8—C7	123.3 (3)
C5—N1—C14	121.0 (3)	C9—C8—C7	118.2 (3)
H1W1—O1W—H2W1	106.3	C10—C9—C8	121.0 (3)
N1—C1—C2	121.1 (4)	C10—C9—H9A	119.5
N1—C1—H1A	119.4	C8—C9—H9A	119.5
C2—C1—H1A	119.4	C11—C10—C9	118.8 (3)
C1—C2—C3	119.0 (4)	C11—C10—H10A	120.6
C1—C2—H2A	120.5	C9—C10—H10A	120.6
C3—C2—H2A	120.5	C10—C11—C12	122.5 (3)
C4—C3—C2	119.2 (3)	C10—C11—Cl1	119.1 (3)
C4—C3—H3A	120.4	C12—C11—Cl1	118.4 (3)
C2—C3—H3A	120.4	C11—C12—C13	118.4 (3)
C3—C4—C5	121.7 (4)	C11—C12—H12A	120.8
C3—C4—H4A	119.2	C13—C12—H12A	120.8
C5—C4—H4A	119.2	C12—C13—C8	120.9 (3)
N1—C5—C4	117.4 (3)	C12—C13—H13A	119.6
N1—C5—C6	119.3 (3)	C8—C13—H13A	119.6
C4—C5—C6	123.4 (3)	N1—C14—H14D	109.5
C7—C6—C5	123.9 (3)	N1—C14—H14A	109.5
C7—C6—H6A	118.0	H14D—C14—H14A	109.5
C5—C6—H6A	118.0	N1—C14—H14B	109.5
C6—C7—C8	127.0 (4)	H14D—C14—H14B	109.5
C6—C7—H7A	116.5	H14A—C14—H14B	109.5
C8—C7—H7A	116.5
C5—N1—C1—C2	0.5 (5)	C5—C6—C7—C8	−179.2 (3)
C14—N1—C1—C2	−178.4 (3)	C6—C7—C8—C13	−6.4 (6)
N1—C1—C2—C3	0.7 (5)	C6—C7—C8—C9	173.2 (4)
C1—C2—C3—C4	−1.3 (5)	C13—C8—C9—C10	0.3 (5)
C2—C3—C4—C5	0.6 (5)	C7—C8—C9—C10	−179.4 (3)
C1—N1—C5—C4	−1.1 (5)	C8—C9—C10—C11	−0.4 (5)
C14—N1—C5—C4	177.7 (3)	C9—C10—C11—C12	0.3 (5)
C1—N1—C5—C6	177.9 (3)	C9—C10—C11—Cl1	−179.9 (3)
C14—N1—C5—C6	−3.2 (5)	C10—C11—C12—C13	−0.2 (5)
C3—C4—C5—N1	0.6 (5)	Cl1—C11—C12—C13	−179.9 (3)
C3—C4—C5—C6	−178.4 (3)	C11—C12—C13—C8	0.0 (5)
N1—C5—C6—C7	−173.9 (3)	C9—C8—C13—C12	−0.1 (5)
C4—C5—C6—C7	5.1 (6)	C7—C8—C13—C12	179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1	0.86	2.87	3.592 (4)	143
O1W—H2W1···I1i	0.85	2.87	3.567 (4)	141
C14—H14A···O1W	0.96	2.50	3.202 (5)	130
C14—H14D···O1Wii	0.96	2.56	3.460 (5)	157
C1—H1A···I1iii	0.93	3.20	3.830 (4)	127
C2—H2A···I1iv	0.93	3.18	3.825 (4)	129
C3—H3A···I1iv	0.93	3.21	3.840 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1	0.86	2.87	3.592 (4)	143
O1W—H2W1⋯I1i	0.85	2.87	3.567 (4)	141
C14—H14A⋯O1W	0.96	2.50	3.202 (5)	130
C14—H14D⋯O1Wii	0.96	2.56	3.460 (5)	157
C1—H1A⋯I1iii	0.93	3.20	3.830 (4)	127
C2—H2A⋯I1iv	0.93	3.17	3.825 (4)	129
C3—H3A⋯I1iv	0.93	3.21	3.840 (4)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .