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

In the title compound, C(20)H(20)NO(+)·I(-)·2H(2)O, the cation is almost planar (r.m.s. deviation = 0.038 Å) and exists in an E configuration. The dihedral angle between the quinolinium ring system and the benzene ring is 0.7 (4)°. In the crystal structure, the cations are stacked in an anti-parallel manner along [100] with π-π inter-actions between the pyridinium and ethoxy-benzene rings [centroid-centroid distance = 3.678 (5) Å]. The cations, iodide anions and water mol-ecules are linked together through O-H⋯O, O-H⋯I and C-H⋯I hydrogen bonds into a two-dimensional network parallel to (001).

Related literature

For background to non-linear optical materials research, see: Kagawa et al. (1994 ▶); Williams (1984 ▶). For the anti­bacterial activity of quinoline derivatives, see: Hopkins et al. (2005 ▶); Kaminsky & Meltzer (1968 ▶); Musiol et al. (2006 ▶); O’Donnell et al. (2010 ▶). For a related structure, see: Laksana et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H20NO+·I−·2H2O

M = 453.30

Triclinic,

a = 8.2450 (9) Å

b = 10.6676 (12) Å

c = 12.2492 (14) Å

α = 85.789 (2)°

β = 70.516 (2)°

γ = 71.272 (2)°

V = 961.21 (19) Å3

Z = 2

Mo Kα radiation

μ = 1.68 mm−1

T = 100 K

0.49 × 0.08 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.493, T max = 0.927

11172 measured reflections

3910 independent reflections

3551 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.211

S = 1.15

3910 reflections

220 parameters

20 restraints

H-atom parameters constrained

Δρmax = 2.43 e Å−3

Δρmin = −0.85 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810010548/ci5058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010548/ci5058Isup2.hkl

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

C20H20NO+·I−·2H2O	Z = 2
Mr = 453.30	F(000) = 456
Triclinic, P1	Dx = 1.566 Mg m−3
Hall symbol: -P 1	Melting point = 492–494 K
a = 8.2450 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6676 (12) Å	Cell parameters from 3910 reflections
c = 12.2492 (14) Å	θ = 1.8–26.5°
α = 85.789 (2)°	µ = 1.68 mm−1
β = 70.516 (2)°	T = 100 K
γ = 71.272 (2)°	Needle, brown
V = 961.21 (19) Å3	0.49 × 0.08 × 0.05 mm

Bruker APEX DUO CCD area-detector diffractometer	3910 independent reflections
Radiation source: sealed tube	3551 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.493, Tmax = 0.927	k = −13→12
11172 measured reflections	l = −15→15

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.1163P)2 + 8.5465P] where P = (Fo2 + 2Fc2)/3
3910 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 2.43 e Å−3
20 restraints	Δρmin = −0.85 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	0.20275 (7)	0.86454 (5)	0.22772 (4)	0.0286 (2)
O1	1.0063 (6)	0.2957 (5)	0.0164 (4)	0.0164 (10)
N1	0.0190 (9)	0.6541 (6)	0.6219 (5)	0.0208 (13)
C1	−0.1326 (9)	0.6672 (8)	0.7248 (6)	0.0217 (11)
C2	−0.2476 (13)	0.7907 (9)	0.7709 (8)	0.0326 (19)
H2A	−0.2303	0.8675	0.7351	0.039*
C3	−0.3924 (12)	0.7963 (10)	0.8742 (9)	0.040 (2)
H3A	−0.4731	0.8783	0.9064	0.048*
C4	−0.4171 (11)	0.6817 (11)	0.9290 (7)	0.034 (2)
H4A	−0.5106	0.6869	0.9985	0.041*
C5	−0.3070 (14)	0.5671 (11)	0.8815 (8)	0.040 (2)
H5A	−0.3259	0.4904	0.9167	0.048*
C6	−0.1606 (11)	0.5559 (9)	0.7787 (8)	0.0286 (18)
C7	−0.0408 (12)	0.4278 (9)	0.7286 (8)	0.0314 (18)
H7A	−0.0604	0.3517	0.7646	0.038*
C8	0.0966 (11)	0.4172 (8)	0.6319 (8)	0.0317 (19)
H8A	0.1738	0.3342	0.6002	0.038*
C9	0.1275 (9)	0.5398 (8)	0.5737 (6)	0.0217 (11)
C10	0.2787 (10)	0.5185 (8)	0.4684 (6)	0.0237 (15)
H10A	0.2917	0.5939	0.4280	0.028*
C11	0.4004 (11)	0.4063 (9)	0.4220 (7)	0.0298 (17)
H11A	0.3834	0.3316	0.4622	0.036*
C12	0.5632 (11)	0.3792 (10)	0.3141 (7)	0.0322 (19)
C13	0.6568 (11)	0.2555 (10)	0.2820 (7)	0.0325 (19)
H13A	0.6225	0.1887	0.3276	0.039*
C14	0.8067 (11)	0.2211 (9)	0.1813 (7)	0.0267 (16)
H14A	0.8703	0.1327	0.1590	0.032*
C15	0.8592 (9)	0.3215 (7)	0.1150 (6)	0.0155 (13)
C16	0.7674 (10)	0.4541 (8)	0.1450 (6)	0.0225 (15)
H16A	0.8050	0.5203	0.1003	0.027*
C17	0.6132 (11)	0.4851 (9)	0.2471 (7)	0.0308 (18)
H17A	0.5457	0.5728	0.2702	0.037*
C18	1.0977 (11)	0.1578 (8)	−0.0216 (7)	0.0251 (16)
H18A	1.0150	0.1195	−0.0369	0.030*
H18B	1.1423	0.1076	0.0375	0.030*
C19	1.2542 (11)	0.1552 (10)	−0.1316 (7)	0.037 (2)
H19A	1.3064	0.0676	−0.1668	0.055*
H19B	1.3445	0.1797	−0.1130	0.055*
H19C	1.2106	0.2166	−0.1845	0.055*
C20	0.0510 (12)	0.7731 (9)	0.5679 (8)	0.0340 (19)
H20A	0.1758	0.7529	0.5203	0.051*
H20B	0.0235	0.8385	0.6267	0.051*
H20C	−0.0252	0.8067	0.5209	0.051*
O1W	0.2568 (8)	0.0771 (7)	0.5862 (6)	0.0385 (15)
H1W1	0.3030	−0.0003	0.6046	0.058*
H2W1	0.1437	0.0966	0.6162	0.058*
O2W	0.5594 (9)	0.1337 (7)	0.5759 (5)	0.0335 (14)
H1W2	0.4515	0.1362	0.6067	0.050*
H2W2	0.6181	0.0959	0.6196	0.050*

	U11	U22	U33	U12	U13	U23
I1	0.0254 (3)	0.0302 (3)	0.0278 (3)	−0.0099 (2)	−0.0040 (2)	−0.0019 (2)
O1	0.014 (2)	0.013 (2)	0.014 (2)	0.0002 (18)	0.0023 (18)	−0.0053 (18)
N1	0.025 (3)	0.021 (3)	0.018 (3)	−0.006 (2)	−0.011 (2)	0.001 (2)
C1	0.015 (2)	0.042 (3)	0.011 (2)	−0.010 (2)	−0.0062 (18)	−0.005 (2)
C2	0.042 (5)	0.033 (5)	0.041 (5)	−0.021 (4)	−0.029 (4)	0.016 (4)
C3	0.029 (4)	0.039 (5)	0.052 (5)	0.009 (4)	−0.026 (4)	−0.027 (4)
C4	0.021 (4)	0.071 (7)	0.014 (4)	−0.022 (4)	−0.001 (3)	−0.004 (4)
C5	0.055 (6)	0.054 (6)	0.035 (5)	−0.035 (5)	−0.032 (5)	0.020 (5)
C6	0.023 (3)	0.035 (4)	0.036 (4)	−0.003 (3)	−0.023 (3)	−0.010 (3)
C7	0.035 (4)	0.034 (5)	0.033 (5)	−0.017 (4)	−0.016 (4)	0.011 (4)
C8	0.025 (4)	0.019 (4)	0.048 (5)	−0.001 (3)	−0.012 (4)	−0.012 (4)
C9	0.015 (2)	0.042 (3)	0.011 (2)	−0.010 (2)	−0.0062 (18)	−0.005 (2)
C10	0.018 (3)	0.032 (4)	0.018 (3)	−0.004 (3)	−0.003 (3)	−0.007 (3)
C11	0.028 (4)	0.033 (5)	0.024 (4)	−0.008 (3)	−0.004 (3)	0.000 (3)
C12	0.026 (4)	0.058 (6)	0.013 (3)	−0.013 (4)	−0.008 (3)	0.004 (3)
C13	0.024 (4)	0.049 (6)	0.019 (4)	−0.014 (4)	0.001 (3)	0.005 (4)
C14	0.022 (4)	0.038 (5)	0.019 (4)	−0.010 (3)	−0.006 (3)	0.007 (3)
C15	0.010 (3)	0.023 (4)	0.014 (3)	−0.006 (3)	−0.004 (2)	−0.002 (3)
C16	0.018 (3)	0.025 (4)	0.019 (4)	0.005 (3)	−0.009 (3)	−0.007 (3)
C17	0.027 (4)	0.035 (5)	0.026 (4)	0.006 (3)	−0.014 (3)	−0.016 (3)
C18	0.027 (4)	0.017 (4)	0.024 (4)	0.006 (3)	−0.010 (3)	−0.009 (3)
C19	0.025 (4)	0.047 (6)	0.024 (4)	0.008 (4)	−0.006 (3)	−0.017 (4)
C20	0.031 (4)	0.034 (5)	0.026 (4)	−0.005 (3)	−0.003 (3)	0.007 (4)
O1W	0.016 (3)	0.057 (4)	0.034 (3)	−0.007 (3)	0.000 (2)	−0.007 (3)
O2W	0.043 (3)	0.047 (4)	0.023 (3)	−0.026 (3)	−0.015 (3)	0.001 (3)

O1—C15	1.365 (8)	C11—H11A	0.93
O1—C18	1.450 (9)	C12—C13	1.308 (14)
N1—C9	1.300 (10)	C12—C17	1.435 (14)
N1—C1	1.426 (9)	C13—C14	1.393 (11)
N1—C20	1.447 (11)	C13—H13A	0.93
C1—C6	1.364 (13)	C14—C15	1.389 (11)
C1—C2	1.380 (13)	C14—H14A	0.93
C2—C3	1.410 (14)	C15—C16	1.383 (11)
C2—H2A	0.93	C16—C17	1.421 (11)
C3—C4	1.391 (15)	C16—H16A	0.93
C3—H3A	0.93	C17—H17A	0.93
C4—C5	1.303 (15)	C18—C19	1.517 (12)
C4—H4A	0.93	C18—H18A	0.97
C5—C6	1.404 (14)	C18—H18B	0.97
C5—H5A	0.93	C19—H19A	0.96
C6—C7	1.440 (13)	C19—H19B	0.96
C7—C8	1.319 (13)	C19—H19C	0.96
C7—H7A	0.93	C20—H20A	0.96
C8—C9	1.496 (12)	C20—H20B	0.96
C8—H8A	0.93	C20—H20C	0.96
C9—C10	1.435 (10)	O1W—H1W1	0.84
C10—C11	1.307 (12)	O1W—H2W1	0.84
C10—H10A	0.93	O2W—H1W2	0.84
C11—C12	1.502 (11)	O2W—H2W2	0.84
C15—O1—C18	116.7 (6)	C13—C12—C11	117.9 (8)
C9—N1—C1	122.7 (7)	C17—C12—C11	121.3 (8)
C9—N1—C20	118.8 (7)	C12—C13—C14	121.8 (9)
C1—N1—C20	118.6 (7)	C12—C13—H13A	119.1
C6—C1—C2	120.2 (7)	C14—C13—H13A	119.1
C6—C1—N1	119.1 (7)	C15—C14—C13	118.7 (8)
C2—C1—N1	120.7 (8)	C15—C14—H14A	120.6
C1—C2—C3	117.6 (8)	C13—C14—H14A	120.6
C1—C2—H2A	121.2	O1—C15—C16	115.6 (6)
C3—C2—H2A	121.2	O1—C15—C14	122.1 (7)
C4—C3—C2	121.4 (8)	C16—C15—C14	122.3 (7)
C4—C3—H3A	119.3	C15—C16—C17	117.2 (8)
C2—C3—H3A	119.3	C15—C16—H16A	121.4
C5—C4—C3	119.0 (8)	C17—C16—H16A	121.4
C5—C4—H4A	120.5	C16—C17—C12	119.1 (8)
C3—C4—H4A	120.5	C16—C17—H17A	120.5
C4—C5—C6	122.0 (9)	C12—C17—H17A	120.5
C4—C5—H5A	119.0	O1—C18—C19	106.7 (7)
C6—C5—H5A	119.0	O1—C18—H18A	110.4
C1—C6—C5	119.9 (8)	C19—C18—H18A	110.4
C1—C6—C7	119.4 (8)	O1—C18—H18B	110.4
C5—C6—C7	120.7 (9)	C19—C18—H18B	110.4
C8—C7—C6	120.7 (8)	H18A—C18—H18B	108.6
C8—C7—H7A	119.7	C18—C19—H19A	109.5
C6—C7—H7A	119.7	C18—C19—H19B	109.5
C7—C8—C9	119.6 (8)	H19A—C19—H19B	109.5
C7—C8—H8A	120.2	C18—C19—H19C	109.5
C9—C8—H8A	120.2	H19A—C19—H19C	109.5
N1—C9—C10	126.0 (8)	H19B—C19—H19C	109.5
N1—C9—C8	118.4 (7)	N1—C20—H20A	109.5
C10—C9—C8	115.6 (7)	N1—C20—H20B	109.5
C11—C10—C9	128.1 (8)	H20A—C20—H20B	109.5
C11—C10—H10A	115.9	N1—C20—H20C	109.5
C9—C10—H10A	115.9	H20A—C20—H20C	109.5
C10—C11—C12	130.2 (9)	H20B—C20—H20C	109.5
C10—C11—H11A	114.9	H1W1—O1W—H2W1	107.7
C12—C11—H11A	114.9	H1W2—O2W—H2W2	109.1
C13—C12—C17	120.9 (8)
C9—N1—C1—C6	3.5 (10)	C20—N1—C9—C8	178.3 (7)
C20—N1—C1—C6	−177.8 (7)	C7—C8—C9—N1	1.4 (11)
C9—N1—C1—C2	−177.9 (7)	C7—C8—C9—C10	−179.2 (7)
C20—N1—C1—C2	0.8 (10)	N1—C9—C10—C11	173.5 (8)
C6—C1—C2—C3	0.0 (11)	C8—C9—C10—C11	−5.8 (12)
N1—C1—C2—C3	−178.6 (6)	C9—C10—C11—C12	−178.2 (8)
C1—C2—C3—C4	1.1 (11)	C10—C11—C12—C13	−175.1 (9)
C2—C3—C4—C5	−2.2 (12)	C10—C11—C12—C17	3.9 (14)
C3—C4—C5—C6	2.2 (12)	C17—C12—C13—C14	−0.9 (13)
C2—C1—C6—C5	0.0 (10)	C11—C12—C13—C14	178.1 (8)
N1—C1—C6—C5	178.6 (6)	C12—C13—C14—C15	1.3 (12)
C2—C1—C6—C7	179.1 (7)	C18—O1—C15—C16	−175.9 (6)
N1—C1—C6—C7	−2.3 (10)	C18—O1—C15—C14	4.8 (9)
C4—C5—C6—C1	−1.2 (12)	C13—C14—C15—O1	178.9 (7)
C4—C5—C6—C7	179.7 (8)	C13—C14—C15—C16	−0.4 (11)
C1—C6—C7—C8	0.8 (11)	O1—C15—C16—C17	179.9 (6)
C5—C6—C7—C8	179.9 (8)	C14—C15—C16—C17	−0.8 (10)
C6—C7—C8—C9	−0.3 (12)	C15—C16—C17—C12	1.1 (10)
C1—N1—C9—C10	177.7 (6)	C13—C12—C17—C16	−0.3 (12)
C20—N1—C9—C10	−1.1 (11)	C11—C12—C17—C16	−179.3 (7)
C1—N1—C9—C8	−3.0 (10)	C15—O1—C18—C19	179.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H1W2···O1W	0.83	1.99	2.711 (11)	143
O1W—H2W1···I1i	0.84	2.77	3.588 (7)	163
O2W—H2W2···I1ii	0.84	2.87	3.579 (7)	144
C2—H2A···I1iii	0.93	3.02	3.814 (10)	145
C7—H7A···I1i	0.93	2.89	3.708 (10)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H1W2⋯O1W	0.83	1.99	2.711 (11)	143
O1W—H2W1⋯I1i	0.84	2.77	3.588 (7)	163
O2W—H2W2⋯I1ii	0.84	2.87	3.579 (7)	144
C2—H2A⋯I1iii	0.93	3.02	3.814 (10)	145
C7—H7A⋯I1i	0.93	2.89	3.708 (10)	148

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