(E)-2-[4-(Dimethyl-amino)styr-yl]-1-methyl-quinolinium iodide sesquihydrate.

In the title compound, C(20)H(21)N(2) (+.)I(-)·1.5H(2)O, the cation exists in the E configuration and is not planar. The dihedral angle between the quinolinium and dimethyl-amino-phenyl rings is 9.26 (6)°. The O atom of one of the solvent water mol-ecules lies on a twofold rotation axis. In the crystal structure, the cations form one-dimensional zigzag chains along the [001] direction. The cations are linked to water mol-ecules and iodide ions through weak C-H⋯O and C-H⋯I inter-actions, respectively. Water mol-ecules and iodide ions form O-H⋯O and O-H⋯I hydrogen bonds, which stabilize the crystal structure. A C-H⋯π inter-action is also present.

Related literature

For bond lengths, see: Allen et al. (1987 ▶). For background to non-linear optical (NLO) materials research, see: Chia et al. (1995 ▶); Marder et al. (1994 ▶); Otero et al. (2002 ▶); Pan et al. (1996 ▶). For related structures, see for example: Chantrapromma et al. (2006 ▶, 2007a ▶,b ▶,c ▶,d ▶); Dittrich et al. (2003 ▶); Jindawong et al. (2005 ▶); Kobkeatthawin et al. (2008 ▶); Nogi et al. (2000 ▶); Sato et al. (1999 ▶); Umezawa et al. (2000 ▶).

Experimental

Crystal data

C20H21N2 +·I−·1.5H2O

M = 443.31

Monoclinic,

a = 20.8997 (4) Å

b = 10.5941 (2) Å

c = 18.4020 (4) Å

β = 113.047 (1)°

V = 3749.24 (13) Å3

Z = 8

Mo Kα radiation

μ = 1.72 mm−1

T = 100.0 (1) K

0.52 × 0.35 × 0.12 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.469, T max = 0.818

50083 measured reflections

8240 independent reflections

7476 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.07

8240 reflections

237 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.58 e Å−3

Δρmin = −0.80 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/S1600536808010465/sj2479sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010465/sj2479Isup2.hkl

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

C20H21N2+·I–·1.5H2O	F000 = 1784
Mr = 443.31	Dx = 1.571 Mg m−3
Monoclinic, C2/c	Melting point = 491–493 K
Hall symbol: -C 2yc	Mo Kα radiation λ = 0.71073 Å
a = 20.8997 (4) Å	Cell parameters from 8240 reflections
b = 10.5941 (2) Å	θ = 2.1–35.0º
c = 18.4020 (4) Å	µ = 1.72 mm−1
β = 113.047 (1)º	T = 100.0 (1) K
V = 3749.24 (13) Å3	Block, green
Z = 8	0.52 × 0.35 × 0.12 mm

Bruker SMART APEX2 CCD area-detector diffractometer	8240 independent reflections
Radiation source: fine-focus sealed tube	7476 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 8.33 pixels mm-1	θmax = 35.0º
T = 100.0(1) K	θmin = 2.1º
ω scans	h = −33→33
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −17→15
Tmin = 0.469, Tmax = 0.818	l = −29→28
50083 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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0246P)2 + 7.1959P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
8240 reflections	Δρmax = 1.58 e Å−3
237 parameters	Δρmin = −0.80 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem 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	0.121463 (5)	0.401312 (10)	0.489877 (6)	0.02205 (3)
N1	0.34849 (6)	0.45765 (12)	−0.04848 (7)	0.0163 (2)
N2	0.16088 (7)	0.23257 (14)	0.29101 (8)	0.0219 (2)
C1	0.39458 (7)	0.47357 (14)	−0.08616 (8)	0.0173 (2)
C2	0.38630 (8)	0.57284 (16)	−0.13994 (9)	0.0222 (3)
H2A	0.3488	0.6279	−0.1525	0.027*
C3	0.43416 (9)	0.58795 (17)	−0.17383 (10)	0.0249 (3)
H3A	0.4283	0.6533	−0.2096	0.030*
C4	0.49123 (8)	0.50731 (18)	−0.15566 (9)	0.0244 (3)
H4A	0.5234	0.5202	−0.1784	0.029*
C5	0.49965 (8)	0.40906 (16)	−0.10418 (9)	0.0219 (3)
H5A	0.5371	0.3542	−0.0929	0.026*
C6	0.45170 (8)	0.39079 (14)	−0.06823 (8)	0.0183 (2)
C7	0.45974 (8)	0.29187 (16)	−0.01383 (9)	0.0211 (3)
H7A	0.4961	0.2347	−0.0029	0.025*
C8	0.41475 (8)	0.27979 (15)	0.02247 (9)	0.0201 (3)
H8A	0.4206	0.2142	0.0581	0.024*
C9	0.35853 (7)	0.36612 (14)	0.00684 (8)	0.0163 (2)
C10	0.31320 (7)	0.35646 (14)	0.04900 (8)	0.0173 (2)
H10A	0.2735	0.4065	0.0326	0.021*
C11	0.32564 (7)	0.27790 (14)	0.11134 (8)	0.0170 (2)
H11A	0.3652	0.2275	0.1265	0.020*
C12	0.28250 (7)	0.26643 (13)	0.15584 (8)	0.0157 (2)
C13	0.29994 (7)	0.18026 (14)	0.21874 (9)	0.0185 (2)
H13A	0.3396	0.1309	0.2309	0.022*
C14	0.26020 (7)	0.16647 (14)	0.26310 (9)	0.0193 (2)
H14A	0.2730	0.1075	0.3038	0.023*
C15	0.20009 (7)	0.24148 (14)	0.24709 (8)	0.0164 (2)
C16	0.18213 (7)	0.32815 (14)	0.18357 (8)	0.0177 (2)
H16A	0.1428	0.3783	0.1714	0.021*
C17	0.22208 (7)	0.33918 (14)	0.13970 (8)	0.0176 (2)
H17A	0.2088	0.3964	0.0981	0.021*
C18	0.17497 (9)	0.13464 (18)	0.35064 (10)	0.0262 (3)
H18A	0.2231	0.1376	0.3857	0.039*
H18B	0.1646	0.0535	0.3254	0.039*
H18C	0.1465	0.1481	0.3801	0.039*
C19	0.09759 (8)	0.30611 (17)	0.27093 (10)	0.0236 (3)
H19A	0.1078	0.3939	0.2680	0.035*
H19B	0.0792	0.2943	0.3107	0.035*
H19C	0.0640	0.2788	0.2208	0.035*
C20	0.28968 (8)	0.54554 (16)	−0.07022 (10)	0.0223 (3)
H20A	0.2575	0.5167	−0.0483	0.034*
H20B	0.2667	0.5494	−0.1267	0.034*
H20C	0.3064	0.6280	−0.0499	0.034*
O1W	0.03830 (8)	0.54957 (15)	0.13362 (8)	0.0297 (3)
O2W	0.0000	0.6809 (2)	0.2500	0.0385 (5)
H1W2	0.0114 (15)	0.633 (3)	0.2215 (16)	0.044 (8)*
H1W1	0.0030 (16)	0.508 (3)	0.1033 (17)	0.049 (8)*
H2W1	0.0580 (16)	0.564 (3)	0.1055 (18)	0.049 (8)*

	U11	U22	U33	U12	U13	U23
I1	0.01875 (5)	0.02151 (5)	0.02561 (5)	−0.00453 (3)	0.00840 (4)	−0.00498 (4)
N1	0.0154 (5)	0.0157 (5)	0.0180 (5)	0.0016 (4)	0.0066 (4)	0.0002 (4)
N2	0.0203 (5)	0.0256 (6)	0.0235 (6)	0.0038 (5)	0.0126 (5)	0.0083 (5)
C1	0.0164 (5)	0.0198 (6)	0.0165 (5)	−0.0016 (5)	0.0073 (5)	−0.0020 (5)
C2	0.0190 (6)	0.0242 (7)	0.0236 (6)	0.0016 (5)	0.0086 (5)	0.0041 (5)
C3	0.0233 (7)	0.0289 (8)	0.0229 (7)	−0.0006 (6)	0.0096 (6)	0.0055 (6)
C4	0.0214 (6)	0.0351 (8)	0.0199 (6)	−0.0028 (6)	0.0117 (5)	−0.0010 (6)
C5	0.0180 (6)	0.0282 (7)	0.0205 (6)	0.0022 (5)	0.0088 (5)	−0.0032 (5)
C6	0.0177 (6)	0.0205 (6)	0.0167 (5)	0.0008 (5)	0.0067 (5)	−0.0009 (5)
C7	0.0198 (6)	0.0222 (7)	0.0219 (6)	0.0056 (5)	0.0088 (5)	0.0013 (5)
C8	0.0183 (6)	0.0222 (7)	0.0214 (6)	0.0051 (5)	0.0095 (5)	0.0036 (5)
C9	0.0168 (5)	0.0153 (5)	0.0173 (5)	0.0002 (4)	0.0072 (5)	−0.0001 (4)
C10	0.0182 (6)	0.0172 (6)	0.0185 (6)	−0.0002 (5)	0.0093 (5)	−0.0006 (5)
C11	0.0149 (5)	0.0184 (6)	0.0179 (5)	0.0003 (4)	0.0068 (4)	−0.0001 (5)
C12	0.0149 (5)	0.0160 (5)	0.0162 (5)	−0.0004 (4)	0.0060 (4)	0.0004 (4)
C13	0.0162 (5)	0.0194 (6)	0.0199 (6)	0.0031 (5)	0.0071 (5)	0.0036 (5)
C14	0.0183 (6)	0.0193 (6)	0.0208 (6)	0.0028 (5)	0.0082 (5)	0.0057 (5)
C15	0.0152 (5)	0.0173 (6)	0.0164 (5)	−0.0011 (4)	0.0059 (4)	0.0012 (4)
C16	0.0161 (5)	0.0182 (6)	0.0187 (6)	0.0021 (4)	0.0067 (5)	0.0036 (5)
C17	0.0179 (6)	0.0179 (6)	0.0178 (6)	0.0023 (5)	0.0079 (5)	0.0041 (5)
C18	0.0246 (7)	0.0310 (8)	0.0267 (7)	0.0036 (6)	0.0143 (6)	0.0111 (6)
C19	0.0213 (6)	0.0291 (8)	0.0236 (6)	0.0040 (6)	0.0125 (5)	0.0025 (6)
C20	0.0209 (6)	0.0212 (7)	0.0284 (7)	0.0064 (5)	0.0133 (6)	0.0048 (5)
O1W	0.0271 (6)	0.0340 (7)	0.0266 (6)	0.0012 (5)	0.0092 (5)	0.0014 (5)
O2W	0.0530 (13)	0.0278 (10)	0.0469 (12)	0.000	0.0329 (11)	0.000

N1—C9	1.3614 (19)	C11—C12	1.4411 (19)
N1—C1	1.4001 (18)	C11—H11A	0.9300
N1—C20	1.4672 (19)	C12—C13	1.406 (2)
N2—C15	1.3611 (18)	C12—C17	1.408 (2)
N2—C19	1.453 (2)	C13—C14	1.381 (2)
N2—C18	1.454 (2)	C13—H13A	0.9300
C1—C2	1.408 (2)	C14—C15	1.417 (2)
C1—C6	1.412 (2)	C14—H14A	0.9300
C2—C3	1.380 (2)	C15—C16	1.417 (2)
C2—H2A	0.9300	C16—C17	1.3750 (19)
C3—C4	1.397 (2)	C16—H16A	0.9300
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.372 (2)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.414 (2)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.413 (2)	C19—H19B	0.9600
C7—C8	1.356 (2)	C19—H19C	0.9600
C7—H7A	0.9300	C20—H20A	0.9600
C8—C9	1.427 (2)	C20—H20B	0.9600
C8—H8A	0.9300	C20—H20C	0.9600
C9—C10	1.4442 (19)	O1W—H1W1	0.85 (3)
C10—C11	1.357 (2)	O1W—H2W1	0.79 (3)
C10—H10A	0.9300	O2W—H1W2	0.83 (3)
C9—N1—C1	121.43 (12)	C12—C11—H11A	117.4
C9—N1—C20	121.57 (12)	C13—C12—C17	116.83 (12)
C1—N1—C20	116.99 (12)	C13—C12—C11	120.29 (13)
C15—N2—C19	120.78 (13)	C17—C12—C11	122.88 (13)
C15—N2—C18	120.43 (13)	C14—C13—C12	122.22 (13)
C19—N2—C18	118.03 (12)	C14—C13—H13A	118.9
N1—C1—C2	121.28 (13)	C12—C13—H13A	118.9
N1—C1—C6	119.48 (13)	C13—C14—C15	120.47 (13)
C2—C1—C6	119.22 (13)	C13—C14—H14A	119.8
C3—C2—C1	119.55 (15)	C15—C14—H14A	119.8
C3—C2—H2A	120.2	N2—C15—C14	121.92 (13)
C1—C2—H2A	120.2	N2—C15—C16	120.54 (13)
C2—C3—C4	121.53 (15)	C14—C15—C16	117.54 (12)
C2—C3—H3A	119.2	C17—C16—C15	120.92 (13)
C4—C3—H3A	119.2	C17—C16—H16A	119.5
C5—C4—C3	119.73 (14)	C15—C16—H16A	119.5
C5—C4—H4A	120.1	C16—C17—C12	122.01 (13)
C3—C4—H4A	120.1	C16—C17—H17A	119.0
C4—C5—C6	120.29 (14)	C12—C17—H17A	119.0
C4—C5—H5A	119.9	N2—C18—H18A	109.5
C6—C5—H5A	119.9	N2—C18—H18B	109.5
C1—C6—C7	118.76 (13)	H18A—C18—H18B	109.5
C1—C6—C5	119.66 (14)	N2—C18—H18C	109.5
C7—C6—C5	121.58 (14)	H18A—C18—H18C	109.5
C8—C7—C6	120.39 (14)	H18B—C18—H18C	109.5
C8—C7—H7A	119.8	N2—C19—H19A	109.5
C6—C7—H7A	119.8	N2—C19—H19B	109.5
C7—C8—C9	121.03 (14)	H19A—C19—H19B	109.5
C7—C8—H8A	119.5	N2—C19—H19C	109.5
C9—C8—H8A	119.5	H19A—C19—H19C	109.5
N1—C9—C8	118.76 (13)	H19B—C19—H19C	109.5
N1—C9—C10	120.71 (13)	N1—C20—H20A	109.5
C8—C9—C10	120.53 (13)	N1—C20—H20B	109.5
C11—C10—C9	123.26 (13)	H20A—C20—H20B	109.5
C11—C10—H10A	118.4	N1—C20—H20C	109.5
C9—C10—H10A	118.4	H20A—C20—H20C	109.5
C10—C11—C12	125.20 (13)	H20B—C20—H20C	109.5
C10—C11—H11A	117.4	H1W1—O1W—H2W1	102 (3)
C9—N1—C1—C2	−176.27 (14)	C7—C8—C9—N1	3.4 (2)
C20—N1—C1—C2	2.6 (2)	C7—C8—C9—C10	−176.63 (14)
C9—N1—C1—C6	1.9 (2)	N1—C9—C10—C11	−171.48 (14)
C20—N1—C1—C6	−179.27 (14)	C8—C9—C10—C11	8.5 (2)
N1—C1—C2—C3	177.80 (15)	C9—C10—C11—C12	179.05 (14)
C6—C1—C2—C3	−0.3 (2)	C10—C11—C12—C13	179.02 (14)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—C17	−1.2 (2)
C2—C3—C4—C5	1.3 (3)	C17—C12—C13—C14	0.0 (2)
C3—C4—C5—C6	−1.4 (2)	C11—C12—C13—C14	179.79 (14)
N1—C1—C6—C7	1.5 (2)	C12—C13—C14—C15	−1.0 (2)
C2—C1—C6—C7	179.65 (14)	C19—N2—C15—C14	−176.95 (15)
N1—C1—C6—C5	−177.92 (13)	C18—N2—C15—C14	−7.2 (2)
C2—C1—C6—C5	0.2 (2)	C19—N2—C15—C16	3.7 (2)
C4—C5—C6—C1	0.6 (2)	C18—N2—C15—C16	173.45 (15)
C4—C5—C6—C7	−178.79 (15)	C13—C14—C15—N2	−178.22 (15)
C1—C6—C7—C8	−2.3 (2)	C13—C14—C15—C16	1.2 (2)
C5—C6—C7—C8	177.06 (15)	N2—C15—C16—C17	178.95 (15)
C6—C7—C8—C9	−0.1 (2)	C14—C15—C16—C17	−0.5 (2)
C1—N1—C9—C8	−4.2 (2)	C15—C16—C17—C12	−0.5 (2)
C20—N1—C9—C8	176.94 (14)	C13—C12—C17—C16	0.7 (2)
C1—N1—C9—C10	175.76 (13)	C11—C12—C17—C16	−179.05 (14)
C20—N1—C9—C10	−3.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···I1i	0.85 (3)	2.74 (3)	3.5832 (16)	172 (3)
O2W—H1W2···O1W	0.83 (3)	2.10 (3)	2.9164 (19)	167 (3)
O1W—H2W1···I1ii	0.79 (3)	2.94 (3)	3.7267 (16)	174 (3)
C3—H3A···O2Wiii	0.93	2.60	3.371 (2)	141
C7—H7A···I1iv	0.93	3.04	3.9290 (18)	161
C17—H17A···I1ii	0.93	3.01	3.8784 (14)	157
C2—H2A···Cg1ii	0.93	3.02	3.7648 (17)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯I1i	0.85 (3)	2.74 (3)	3.5832 (16)	172 (3)
O2W—H1W2⋯O1W	0.83 (3)	2.10 (3)	2.9164 (19)	167 (3)
O1W—H2W1⋯I1ii	0.79 (3)	2.94 (3)	3.7267 (16)	174 (3)
C3—H3A⋯O2Wiii	0.93	2.60	3.371 (2)	141
C7—H7A⋯I1iv	0.93	3.04	3.9290 (18)	161
C17—H17A⋯I1ii	0.93	3.01	3.8784 (14)	157
C2—H2A⋯Cg1ii	0.93	3.02	3.7648 (17)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C12–C17 ring.