2-[(E)-2-(4-Eth­oxy­phen­yl)ethen­yl]-1-methyl­quinolinium 4-fluoro­benzene­sulfonate

Fun, H.-K.; Kobkeatthawin, T.; Ruanwas, P.; Quah, C.K.; Chantrapromma, S.

doi:10.1107/S1600536813032509

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o11-o12

https://doi.org/10.1107/S1600536813032509

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2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylquinolinium 4-fluorobenzenesulfonate

Hoong-Kun Fun,^a ^*‡ Thawanrat Kobkeatthawin,^b Pumsak Ruanwas,^b Ching Kheng Quah ^a and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 22 November 2013; accepted 29 November 2013; online 4 December 2013)

In the structure of the title salt, C₂₀H₂₀NO⁺·C₆H₄FO₃S⁻, the 4-(ethoxyphenyl)ethenyl unit is disordered over two positions with a refined site-occupancy ratio of 0.610 (6):0.390 (6). The cation is nearly planar, the dihedral angle between the quinolinium and benzene rings being 6.7 (4) and 1.7 (7)° for the major and minor components, respectively. The ethoxy group is essentially coplanar with the benzene ring [C—O—C—C_methy = 177.1 (8) and 177.8 (12)° for the major and minor components, respectively]. In the crystal, cations and anions are linked into chains along the b-axis direction by C—H⋯O_sulfonyl weak interactions. These chains are further connected into sheets parallel to (001) by C—H⋯O_sulfonyl weak interactions. The chains are also stacked along the a axis through π–π interactions involving the quinolinium and benzene rings [centroid–centroid distances = 3.636 (5) Å for the major component and 3.800 (9) Å for the minor component]. C—H⋯π interactions are also present.

CCDC reference: 974454

Related literature

For background to the bioactivity and non-linear optical properties of quinolinium derivatives, see: Chanawanno et al. (2010 ); Hopkins et al. (2005 ); Musiol et al. (2006 ); O'Donnell et al. (2010 ); Ruanwas et al. (2010 ). For related structures, see: Chantrapromma et al. (2011 ); Fun et al. (2010 ); Ruanwas et al. (2010). 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⁺·C₆H₄FO₃S⁻
M_r = 465.52
Monoclinic, P 2₁ /n
a = 6.4366 (3) Å
b = 9.8909 (5) Å
c = 34.3628 (15) Å
β = 95.102 (2)°
V = 2179.00 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.37 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.932, T_max = 0.991
19050 measured reflections
4993 independent reflections
3609 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.154
S = 1.09
4993 reflections
392 parameters
418 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C12B–C17B and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2ⁱ	0.93	2.55	3.456 (4)	166
C8—H8A⋯O4ⁱⁱ	0.93	2.41	3.306 (3)	161
C10—H10A⋯O3	0.96	2.55	3.483 (4)	164
C11A—H11A⋯O4ⁱⁱ	0.93	2.52	3.408 (19)	159
C17A—H17A⋯O3	0.93	2.58	3.510 (10)	177
C20—H20B⋯O2ⁱ	0.96	2.53	3.441 (4)	158
C20—H20C⋯O3	0.96	2.44	3.085 (4)	124
C25—H25A⋯O4ⁱⁱⁱ	0.93	2.55	3.264 (4)	134
C13A—H13A⋯Cg5ⁱⁱ	0.93	2.82	3.575 (10)	139
C16A—H16A⋯Cg5	0.93	2.98	3.826 (9)	151
C19A—H19B⋯Cg4ⁱⁱⁱ	0.96	2.99	3.862 (11)	152
C13B—H13B⋯Cg5ⁱⁱ	0.93	2.95	3.765 (16)	147
C16B—H16B⋯Cg5	0.93	2.70	3.562 (13)	155
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) x-1, y, z.

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, PLATON (Spek, 2009 ), Mercury (Macrae et al., 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 974454

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813032509/rz5097sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032509/rz5097Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813032509/rz5097Isup3.cml

checkCIF report

Comment top

Quinolinium derivatives were reported to possess interesting bioactivities and pharmacological activities (Chanawanno et al., 2010; Hopkins et al., 2005; Musiol et al., 2006; O'Donnell et al., 2010), including non-linear optic properties (Ruanwas et al., 2010). During the course of our research on the antibacterial activity of pyridinium and quinolinium salts, the title quinolinium salt (I) was synthesized in order to study the effect of the anion counter-part on its antibacterial activity because its starting quinolinium iodide salt (Chanawanno et al., 2010) was found to be very active against the methicillin-resistant Staphylococcus aureus with a MIC value of 2.34 µg/ml. Herein the synthesis and crystal structure of (I) are reported.

In the title salt (Fig. 1), C₂₀H₂₀NO⁺.C₆H₄FSO₃^-, the 4-(ethoxyphenyl)ethenyl unit is disordered over two positions with a refined site-occupancy ratio of 0.610 (6):0.390 (6). The cation exists in an E configuration with respect to the ethenyl bond [C10 ═C11 = 1.326 (18) Å for the major A component and 1.38 (3) Å for the minor B component] and torsion angle C9—C10—C11—C12 = -178.3 (12) ° for the major A component, and -179.0 (19)° for the minor B component. The 1-methylquinolinium ring system is planar with a rms deviation of 0.0199 (3) Å for the eleven non-H atoms. The cation is planar with dihedral angles between the N1/C1–C9 quinolinium and C12–C17 benzene rings of 6.7 (4) and 1.7 (7)° for the major A and minor B components, respectively. The ethoxy unit is disordered over two positions in such a way that the major A and minor B components are related by a 180° rotation. Moreover the ethoxy unit is co-planar with the attached benzene ring as indicated by the torsion angles C16–C15–O1–C18 = 2.5 (15)° and C15–O1–C18–C19 = 177.1 (8)° for the major A component. The corresponding values are 180.0 (14) and 177.8 (12)° for the minor B component. Bond distances in both cation and anion have normal values (Allen et al., 1987) and are comparable to those observed in related structures (Chantrapromma et al., 2011; Fun et al., 2010; Ruanwas et al., 2010).

In the crystal packing (Fig. 2), cations and anions are linked into chains along the b axis by C—H···O_sulfonyl weak interactions. These chains are further connected into sheets parallel to the (001) plane by C—H···O_sulfonyl weak interactions (Table 1), and these chains are also stacked by π–π interactions involving quinolinium and benzene rings (Fig. 3) with separations Cg₁···Cg₃ⁱ = 3.636 (5) Å in the major component A and Cg₁···Cg₄ⁱ = 3.800 (9) Å in the minor component B (symmetry code as in Table 1); Cg₁, Cg₃ and Cg₄ are the centroids of the N1/C1/C6–C9, C12A–C17A and C12B–C17B rings, respectively. C—H···π interactions (Table 1) are also present.

Related literature top

For background to the bioactivity and non-linear optical properties of quinolinium derivatives, see: Chanawanno et al. (2010); Hopkins et al. (2005); Musiol et al. (2006); O'Donnell et al. (2010); Ruanwas et al. (2010). For related structures, see: Chantrapromma et al. (2011); Fun et al. (2010); Ruanwas et al. (2010). 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 top

The title compound was synthesized by dissolving silver(I) 4-fluorobenzenesulfonate (0.20 g, 0.71 mmol) in methanol (20 ml) which upon heating was added to a solution of 2-[(E)-2-(4-ethoxyphenyl)ethenyl]-1-methylquinolinium iodide (Fun et al., 2010) (0.29 g, 0.71 mmol) in hot methanol (30 ml). The mixture turned yellow and cloudy immediately. After stirring for 0.5 h, the precipitate of silver iodide which formed was filtered and the filtrate was evaporated to give a yellow solid. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after a few weeks.

Structure description top

For background to the bioactivity and non-linear optical properties of quinolinium derivatives, see: Chanawanno et al. (2010); Hopkins et al. (2005); Musiol et al. (2006); O'Donnell et al. (2010); Ruanwas et al. (2010). For related structures, see: Chantrapromma et al. (2011); Fun et al. (2010); Ruanwas et al. (2010). 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).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. Open bonds show the minor component.
	Fig. 2. The crystal packing of the major component of the title compound viewed approximately along the a axis. Hydrogen bonds are drawn as dashed lines.
	Fig. 3. π–π interaction between aromatic rings of the cations of the major component. H-atoms of the cations not involved in hydrogen bonds are omitted for clarity.

2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylquinolinium 4-fluorobenzenesulfonate top

Crystal data top

C₂₀H₂₀NO⁺·C₆H₄FO₃S⁻	F(000) = 976
M_r = 465.52	D_x = 1.419 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4993 reflections
a = 6.4366 (3) Å	θ = 2.1–27.5°
b = 9.8909 (5) Å	µ = 0.19 mm⁻¹
c = 34.3628 (15) Å	T = 100 K
β = 95.102 (2)°	Plate, yellow
V = 2179.00 (18) Å³	0.37 × 0.12 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4993 independent reflections
Radiation source: sealed tube	3609 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.932, T_max = 0.991	k = −12→11
19050 measured reflections	l = −44→44

Refinement top

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0388P)² + 4.3613P] where P = (F_o² + 2F_c²)/3
4993 reflections	(Δ/σ)_max < 0.001
392 parameters	Δρ_max = 0.39 e Å⁻³
418 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₀H₂₀NO⁺·C₆H₄FO₃S⁻	V = 2179.00 (18) Å³
M_r = 465.52	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.4366 (3) Å	µ = 0.19 mm⁻¹
b = 9.8909 (5) Å	T = 100 K
c = 34.3628 (15) Å	0.37 × 0.12 × 0.05 mm
β = 95.102 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4993 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3609 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.991	R_int = 0.060
19050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	418 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.09	Δρ_max = 0.39 e Å⁻³
4993 reflections	Δρ_min = −0.49 e Å⁻³
392 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	1.5593 (3)	0.1235 (2)	0.18311 (7)	0.0173 (5)
C1	1.7488 (4)	0.0857 (3)	0.20382 (8)	0.0170 (6)
C2	1.8922 (4)	0.1828 (3)	0.22024 (9)	0.0211 (6)
H2A	1.8655	0.2748	0.2173	0.025*
C3	2.0733 (4)	0.1375 (3)	0.24085 (9)	0.0233 (6)
H3A	2.1660	0.2008	0.2524	0.028*
C4	2.1223 (4)	0.0006 (3)	0.24491 (9)	0.0214 (6)
H4A	2.2460	−0.0267	0.2587	0.026*
C5	1.9854 (4)	−0.0928 (3)	0.22830 (9)	0.0205 (6)
H5A	2.0182	−0.1842	0.2303	0.025*
C6	1.7957 (4)	−0.0528 (3)	0.20815 (8)	0.0184 (6)
C7	1.6492 (4)	−0.1489 (3)	0.19255 (9)	0.0191 (6)
H7A	1.6790	−0.2406	0.1952	0.023*
C8	1.4663 (4)	−0.1090 (3)	0.17380 (9)	0.0198 (6)
H8A	1.3698	−0.1738	0.1644	0.024*
C9	1.4191 (4)	0.0300 (3)	0.16827 (8)	0.0163 (5)
C10	1.2247 (4)	0.0745 (3)	0.14715 (9)	0.0197 (6)
H10A	1.1959	0.1693	0.1442	0.024*	0.610 (6)
H10B	1.1971	0.1699	0.1466	0.024*	0.390 (6)
C20	1.5120 (5)	0.2681 (3)	0.17700 (10)	0.0245 (7)
H20A	1.4912	0.2865	0.1495	0.037*
H20B	1.6262	0.3213	0.1884	0.037*
H20C	1.3876	0.2905	0.1891	0.037*
O1A	0.3281 (9)	0.0972 (6)	0.04235 (19)	0.0386 (14)	0.610 (6)
C11A	1.086 (2)	−0.0139 (19)	0.1318 (6)	0.0169 (19)	0.610 (6)
H11A	1.1156	−0.1053	0.1356	0.020*	0.610 (6)
C12A	0.889 (2)	0.0214 (10)	0.1092 (4)	0.0174 (16)	0.610 (6)
C13A	0.7675 (19)	−0.0815 (10)	0.0915 (5)	0.0235 (16)	0.610 (6)
H13A	0.8105	−0.1708	0.0950	0.028*	0.610 (6)
C14A	0.5834 (16)	−0.0542 (8)	0.0687 (4)	0.0250 (16)	0.610 (6)
H14A	0.5068	−0.1244	0.0565	0.030*	0.610 (6)
C15A	0.5146 (15)	0.0770 (8)	0.0641 (4)	0.0246 (16)	0.610 (6)
C16A	0.6277 (15)	0.1820 (9)	0.0829 (3)	0.0246 (18)	0.610 (6)
H16A	0.5789	0.2703	0.0805	0.030*	0.610 (6)
C17A	0.8141 (15)	0.1543 (10)	0.1054 (3)	0.0190 (18)	0.610 (6)
H17A	0.8891	0.2246	0.1179	0.023*	0.610 (6)
C18A	0.2520 (9)	0.2376 (8)	0.03791 (18)	0.0459 (17)	0.610 (6)
H18A	0.3556	0.2933	0.0267	0.055*	0.610 (6)
H18B	0.2271	0.2745	0.0632	0.055*	0.610 (6)
C19A	0.0542 (11)	0.2371 (11)	0.0117 (2)	0.061 (2)	0.610 (6)
H19A	−0.0053	0.3262	0.0108	0.092*	0.610 (6)
H19B	−0.0423	0.1745	0.0216	0.092*	0.610 (6)
H19C	0.0832	0.2104	−0.0141	0.092*	0.610 (6)
O1B	0.3343 (14)	0.1530 (7)	0.0407 (3)	0.0238 (16)	0.390 (6)
C11B	1.076 (4)	−0.005 (3)	0.1270 (9)	0.019 (3)	0.390 (6)
H11B	1.1013	−0.0980	0.1272	0.023*	0.390 (6)
C12B	0.883 (3)	0.0408 (17)	0.1054 (8)	0.019 (2)	0.390 (6)
C13B	0.748 (3)	−0.0595 (16)	0.0880 (7)	0.022 (2)	0.390 (6)
H13B	0.7842	−0.1504	0.0903	0.026*	0.390 (6)
C14B	0.561 (3)	−0.0215 (13)	0.0672 (6)	0.022 (2)	0.390 (6)
H14B	0.4692	−0.0872	0.0564	0.027*	0.390 (6)
C15B	0.512 (2)	0.1117 (12)	0.0627 (6)	0.0188 (19)	0.390 (6)
C16B	0.647 (2)	0.2108 (13)	0.0783 (5)	0.020 (2)	0.390 (6)
H16B	0.6125	0.3016	0.0747	0.024*	0.390 (6)
C17B	0.831 (2)	0.1749 (15)	0.0993 (5)	0.017 (2)	0.390 (6)
H17B	0.9209	0.2421	0.1094	0.020*	0.390 (6)
C18B	0.1886 (13)	0.0568 (9)	0.0237 (3)	0.038 (2)	0.390 (6)
H18C	0.1379	−0.0008	0.0436	0.046*	0.390 (6)
H18D	0.2530	0.0005	0.0050	0.046*	0.390 (6)
C19B	0.0125 (13)	0.1380 (12)	0.0035 (3)	0.038 (2)	0.390 (6)
H19D	−0.0927	0.0778	−0.0080	0.057*	0.390 (6)
H19E	0.0647	0.1929	−0.0165	0.057*	0.390 (6)
H19F	−0.0468	0.1950	0.0223	0.057*	0.390 (6)
S1	0.97568 (10)	0.53446 (7)	0.16403 (2)	0.02062 (19)
F1	0.3508 (3)	0.6116 (3)	0.03020 (7)	0.0605 (7)
O2	0.8648 (3)	0.5242 (2)	0.19899 (6)	0.0262 (5)
O3	1.0931 (3)	0.4139 (2)	0.15628 (7)	0.0337 (6)
O4	1.0969 (3)	0.6584 (2)	0.16254 (6)	0.0261 (5)
C21	0.7812 (4)	0.5484 (3)	0.12372 (9)	0.0223 (6)
C22	0.8393 (5)	0.5361 (4)	0.08595 (10)	0.0331 (8)
H22A	0.9763	0.5141	0.0820	0.040*
C23	0.6945 (5)	0.5564 (4)	0.05408 (11)	0.0436 (10)
H23A	0.7320	0.5488	0.0287	0.052*
C24	0.4930 (5)	0.5883 (4)	0.06144 (11)	0.0378 (9)
C25	0.4299 (5)	0.5984 (3)	0.09833 (10)	0.0286 (7)
H25A	0.2922	0.6191	0.1021	0.034*
C26	0.5755 (4)	0.5771 (3)	0.12989 (9)	0.0212 (6)
H26A	0.5355	0.5819	0.1552	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0140 (11)	0.0130 (11)	0.0247 (13)	−0.0001 (8)	0.0009 (9)	−0.0002 (10)
C1	0.0109 (12)	0.0221 (13)	0.0181 (15)	0.0002 (10)	0.0016 (10)	−0.0002 (11)
C2	0.0206 (14)	0.0151 (13)	0.0278 (17)	0.0008 (11)	0.0031 (12)	−0.0024 (12)
C3	0.0174 (14)	0.0256 (15)	0.0268 (17)	−0.0101 (12)	0.0008 (12)	−0.0069 (13)
C4	0.0159 (13)	0.0268 (16)	0.0209 (16)	0.0014 (11)	−0.0011 (11)	0.0017 (12)
C5	0.0213 (14)	0.0170 (13)	0.0231 (16)	0.0033 (11)	0.0013 (12)	0.0011 (12)
C6	0.0154 (13)	0.0196 (14)	0.0201 (15)	−0.0023 (11)	0.0006 (11)	−0.0027 (12)
C7	0.0193 (14)	0.0132 (13)	0.0250 (16)	−0.0004 (10)	0.0031 (11)	−0.0014 (11)
C8	0.0167 (13)	0.0167 (13)	0.0261 (17)	−0.0056 (11)	0.0019 (12)	−0.0019 (12)
C9	0.0100 (12)	0.0209 (13)	0.0184 (14)	−0.0014 (11)	0.0026 (10)	−0.0023 (12)
C10	0.0144 (13)	0.0206 (14)	0.0242 (16)	0.0010 (11)	0.0020 (11)	−0.0012 (12)
C20	0.0198 (14)	0.0152 (13)	0.0371 (19)	0.0009 (11)	−0.0052 (13)	0.0016 (13)
O1A	0.019 (2)	0.065 (3)	0.030 (2)	0.010 (3)	−0.0085 (17)	0.005 (3)
C11A	0.013 (3)	0.019 (3)	0.018 (5)	0.005 (2)	−0.001 (3)	0.003 (3)
C12A	0.013 (2)	0.024 (3)	0.015 (3)	0.006 (2)	0.000 (2)	0.004 (3)
C13A	0.018 (3)	0.026 (3)	0.026 (3)	0.003 (2)	−0.006 (2)	0.005 (3)
C14A	0.019 (3)	0.027 (3)	0.029 (3)	0.004 (3)	−0.003 (2)	−0.002 (3)
C15A	0.016 (2)	0.035 (4)	0.022 (2)	0.006 (3)	−0.003 (2)	0.003 (3)
C16A	0.019 (3)	0.026 (4)	0.030 (3)	0.010 (3)	0.005 (2)	0.008 (3)
C17A	0.014 (3)	0.025 (4)	0.018 (3)	0.000 (2)	0.004 (2)	0.003 (3)
C18A	0.029 (3)	0.077 (4)	0.030 (3)	0.035 (3)	−0.002 (2)	0.009 (3)
C19A	0.037 (3)	0.110 (6)	0.036 (4)	0.033 (4)	−0.006 (3)	0.005 (4)
O1B	0.021 (3)	0.023 (3)	0.026 (3)	−0.008 (3)	−0.006 (2)	0.003 (3)
C11B	0.018 (4)	0.022 (5)	0.017 (5)	−0.004 (4)	0.000 (4)	0.002 (4)
C12B	0.011 (3)	0.027 (4)	0.019 (4)	0.000 (3)	0.001 (3)	0.003 (3)
C13B	0.021 (4)	0.018 (4)	0.025 (4)	0.003 (3)	−0.001 (3)	0.003 (4)
C14B	0.019 (4)	0.025 (4)	0.021 (3)	−0.002 (4)	−0.008 (3)	0.001 (4)
C15B	0.015 (3)	0.022 (4)	0.019 (3)	0.006 (3)	0.002 (3)	0.004 (3)
C16B	0.015 (3)	0.019 (4)	0.026 (4)	−0.001 (3)	0.005 (3)	0.005 (3)
C17B	0.013 (3)	0.015 (4)	0.023 (4)	−0.001 (3)	0.004 (3)	0.008 (3)
C18B	0.031 (4)	0.046 (4)	0.036 (4)	−0.007 (3)	−0.002 (3)	0.002 (4)
C19B	0.017 (4)	0.057 (5)	0.039 (5)	0.006 (4)	−0.007 (3)	0.013 (4)
S1	0.0126 (3)	0.0153 (3)	0.0329 (4)	0.0008 (3)	−0.0040 (3)	−0.0043 (3)
F1	0.0400 (13)	0.096 (2)	0.0406 (14)	0.0180 (13)	−0.0222 (10)	−0.0190 (13)
O2	0.0217 (10)	0.0269 (11)	0.0298 (13)	−0.0014 (9)	0.0015 (9)	0.0035 (10)
O3	0.0195 (11)	0.0232 (11)	0.0559 (16)	0.0070 (9)	−0.0105 (10)	−0.0129 (11)
O4	0.0193 (10)	0.0225 (11)	0.0355 (13)	−0.0056 (8)	−0.0031 (9)	−0.0040 (9)
C21	0.0145 (13)	0.0160 (13)	0.0353 (18)	−0.0031 (11)	−0.0050 (12)	−0.0068 (13)
C22	0.0163 (14)	0.049 (2)	0.0331 (19)	0.0027 (14)	−0.0005 (13)	−0.0184 (17)
C23	0.0313 (18)	0.067 (3)	0.032 (2)	0.0029 (18)	−0.0008 (15)	−0.0210 (19)
C24	0.0289 (17)	0.048 (2)	0.033 (2)	0.0046 (16)	−0.0146 (15)	−0.0118 (17)
C25	0.0139 (14)	0.0277 (16)	0.043 (2)	0.0015 (12)	−0.0054 (13)	−0.0066 (15)
C26	0.0171 (13)	0.0151 (13)	0.0311 (17)	−0.0014 (11)	0.0011 (12)	−0.0029 (12)

Geometric parameters (Å, º) top

N1—C9	1.359 (3)	C18A—H18A	0.9700
N1—C1	1.407 (3)	C18A—H18B	0.9700
N1—C20	1.473 (3)	C19A—H19A	0.9600
C1—C6	1.407 (4)	C19A—H19B	0.9600
C1—C2	1.414 (4)	C19A—H19C	0.9600
C2—C3	1.383 (4)	O1B—C15B	1.375 (11)
C2—H2A	0.9300	O1B—C18B	1.425 (10)
C3—C4	1.394 (4)	C11B—C12B	1.463 (12)
C3—H3A	0.9300	C11B—H11B	0.9300
C4—C5	1.366 (4)	C12B—C17B	1.380 (12)
C4—H4A	0.9300	C12B—C13B	1.417 (12)
C5—C6	1.406 (4)	C13B—C14B	1.399 (12)
C5—H5A	0.9300	C13B—H13B	0.9300
C6—C7	1.411 (4)	C14B—C15B	1.360 (11)
C7—C8	1.350 (4)	C14B—H14B	0.9300
C7—H7A	0.9300	C15B—C16B	1.385 (11)
C8—C9	1.418 (4)	C16B—C17B	1.377 (11)
C8—H8A	0.9300	C16B—H16B	0.9300
C9—C10	1.457 (4)	C17B—H17B	0.9300
C10—C11A	1.326 (18)	C18B—C19B	1.506 (10)
C10—C11B	1.38 (3)	C18B—H18C	0.9700
C10—H10A	0.9600	C18B—H18D	0.9700
C10—H10B	0.9600	C19B—H19D	0.9600
C20—H20A	0.9600	C19B—H19E	0.9600
C20—H20B	0.9600	C19B—H19F	0.9600
C20—H20C	0.9600	S1—O3	1.449 (2)
O1A—C15A	1.371 (7)	S1—O2	1.454 (2)
O1A—C18A	1.475 (8)	S1—O4	1.457 (2)
C11A—C12A	1.467 (8)	S1—C21	1.788 (3)
C11A—H11A	0.9300	F1—C24	1.367 (4)
C12A—C13A	1.392 (8)	C21—C22	1.388 (5)
C12A—C17A	1.403 (8)	C21—C26	1.389 (4)
C13A—C14A	1.388 (8)	C22—C23	1.388 (5)
C13A—H13A	0.9300	C22—H22A	0.9300
C14A—C15A	1.375 (8)	C23—C24	1.380 (5)
C14A—H14A	0.9300	C23—H23A	0.9300
C15A—C16A	1.394 (9)	C24—C25	1.369 (5)
C16A—C17A	1.394 (8)	C25—C26	1.385 (4)
C16A—H16A	0.9300	C25—H25A	0.9300
C17A—H17A	0.9300	C26—H26A	0.9300
C18A—C19A	1.492 (8)

C9—N1—C1	121.7 (2)	C12A—C17A—H17A	119.7
C9—N1—C20	119.0 (2)	O1A—C18A—C19A	108.5 (6)
C1—N1—C20	119.3 (2)	O1A—C18A—H18A	110.0
C6—C1—N1	118.7 (2)	C19A—C18A—H18A	110.0
C6—C1—C2	119.5 (2)	O1A—C18A—H18B	110.0
N1—C1—C2	121.8 (2)	C19A—C18A—H18B	110.0
C3—C2—C1	118.3 (3)	H18A—C18A—H18B	108.4
C3—C2—H2A	120.8	C15B—O1B—C18B	120.8 (8)
C1—C2—H2A	120.8	C10—C11B—C12B	127 (2)
C2—C3—C4	122.6 (3)	C10—C11B—H11B	116.7
C2—C3—H3A	118.7	C12B—C11B—H11B	116.7
C4—C3—H3A	118.7	C17B—C12B—C13B	118.3 (11)
C5—C4—C3	118.9 (3)	C17B—C12B—C11B	124.3 (14)
C5—C4—H4A	120.6	C13B—C12B—C11B	117.2 (13)
C3—C4—H4A	120.6	C14B—C13B—C12B	119.8 (11)
C4—C5—C6	121.0 (3)	C14B—C13B—H13B	120.1
C4—C5—H5A	119.5	C12B—C13B—H13B	120.1
C6—C5—H5A	119.5	C15B—C14B—C13B	119.8 (11)
C5—C6—C1	119.6 (2)	C15B—C14B—H14B	120.1
C5—C6—C7	121.3 (3)	C13B—C14B—H14B	120.1
C1—C6—C7	119.1 (2)	C14B—C15B—O1B	121.5 (10)
C8—C7—C6	120.6 (3)	C14B—C15B—C16B	120.8 (10)
C8—C7—H7A	119.7	O1B—C15B—C16B	117.6 (9)
C6—C7—H7A	119.7	C17B—C16B—C15B	120.0 (10)
C7—C8—C9	121.0 (2)	C17B—C16B—H16B	120.0
C7—C8—H8A	119.5	C15B—C16B—H16B	120.0
C9—C8—H8A	119.5	C16B—C17B—C12B	121.1 (11)
N1—C9—C8	118.8 (2)	C16B—C17B—H17B	119.5
N1—C9—C10	119.6 (2)	C12B—C17B—H17B	119.5
C8—C9—C10	121.6 (2)	O1B—C18B—C19B	105.9 (8)
C11A—C10—C9	121.2 (6)	O1B—C18B—H18C	110.6
C11B—C10—C9	127.1 (10)	C19B—C18B—H18C	110.6
C11A—C10—H10A	119.1	O1B—C18B—H18D	110.6
C11B—C10—H10A	112.9	C19B—C18B—H18D	110.6
C9—C10—H10A	119.8	H18C—C18B—H18D	108.7
C11A—C10—H10B	121.6	C18B—C19B—H19D	109.5
C11B—C10—H10B	115.8	C18B—C19B—H19E	109.5
C9—C10—H10B	117.1	H19D—C19B—H19E	109.5
N1—C20—H20A	109.5	C18B—C19B—H19F	109.5
N1—C20—H20B	109.5	H19D—C19B—H19F	109.5
H20A—C20—H20B	109.5	H19E—C19B—H19F	109.5
N1—C20—H20C	109.5	O3—S1—O2	113.38 (14)
H20A—C20—H20C	109.5	O3—S1—O4	113.36 (13)
H20B—C20—H20C	109.5	O2—S1—O4	113.04 (13)
C15A—O1A—C18A	117.4 (6)	O3—S1—C21	105.18 (13)
C10—C11A—C12A	124.9 (12)	O2—S1—C21	106.51 (13)
C10—C11A—H11A	117.5	O4—S1—C21	104.35 (13)
C12A—C11A—H11A	117.5	C22—C21—C26	120.1 (3)
C13A—C12A—C17A	117.9 (7)	C22—C21—S1	119.3 (2)
C13A—C12A—C11A	118.9 (8)	C26—C21—S1	120.6 (2)
C17A—C12A—C11A	123.2 (9)	C21—C22—C23	120.5 (3)
C14A—C13A—C12A	121.6 (7)	C21—C22—H22A	119.8
C14A—C13A—H13A	119.2	C23—C22—H22A	119.8
C12A—C13A—H13A	119.2	C24—C23—C22	117.7 (3)
C15A—C14A—C13A	119.9 (7)	C24—C23—H23A	121.2
C15A—C14A—H14A	120.0	C22—C23—H23A	121.2
C13A—C14A—H14A	120.0	F1—C24—C25	118.8 (3)
O1A—C15A—C14A	117.2 (7)	F1—C24—C23	118.0 (3)
O1A—C15A—C16A	122.7 (7)	C25—C24—C23	123.2 (3)
C14A—C15A—C16A	120.0 (7)	C24—C25—C26	118.5 (3)
C15A—C16A—C17A	119.9 (7)	C24—C25—H25A	120.7
C15A—C16A—H16A	120.0	C26—C25—H25A	120.7
C17A—C16A—H16A	120.0	C25—C26—C21	120.0 (3)
C16A—C17A—C12A	120.5 (7)	C25—C26—H26A	120.0
C16A—C17A—H17A	119.7	C21—C26—H26A	120.0

C9—N1—C1—C6	1.9 (4)	O1A—C15A—C16A—C17A	178.5 (10)
C20—N1—C1—C6	−177.6 (3)	C14A—C15A—C16A—C17A	2.1 (16)
C9—N1—C1—C2	−178.2 (3)	C15A—C16A—C17A—C12A	0.1 (15)
C20—N1—C1—C2	2.4 (4)	C13A—C12A—C17A—C16A	−3.0 (17)
C6—C1—C2—C3	−1.3 (4)	C11A—C12A—C17A—C16A	178.8 (13)
N1—C1—C2—C3	178.7 (3)	C15A—O1A—C18A—C19A	177.1 (8)
C1—C2—C3—C4	2.1 (5)	C11A—C10—C11B—C12B	140 (19)
C2—C3—C4—C5	−0.7 (5)	C9—C10—C11B—C12B	−179.0 (19)
C3—C4—C5—C6	−1.5 (5)	C10—C11B—C12B—C17B	6 (4)
C4—C5—C6—C1	2.2 (4)	C10—C11B—C12B—C13B	−178 (3)
C4—C5—C6—C7	−176.9 (3)	C17B—C12B—C13B—C14B	−4 (3)
N1—C1—C6—C5	179.2 (3)	C11B—C12B—C13B—C14B	180 (2)
C2—C1—C6—C5	−0.8 (4)	C12B—C13B—C14B—C15B	2 (3)
N1—C1—C6—C7	−1.7 (4)	C13B—C14B—C15B—O1B	176.6 (19)
C2—C1—C6—C7	178.4 (3)	C13B—C14B—C15B—C16B	0 (3)
C5—C6—C7—C8	179.0 (3)	C18B—O1B—C15B—C14B	3 (2)
C1—C6—C7—C8	−0.2 (4)	C18B—O1B—C15B—C16B	180.0 (14)
C6—C7—C8—C9	1.9 (5)	C14B—C15B—C16B—C17B	−1 (3)
C1—N1—C9—C8	−0.2 (4)	O1B—C15B—C16B—C17B	−177.5 (16)
C20—N1—C9—C8	179.3 (3)	C15B—C16B—C17B—C12B	−1 (3)
C1—N1—C9—C10	179.8 (3)	C13B—C12B—C17B—C16B	3 (3)
C20—N1—C9—C10	−0.7 (4)	C11B—C12B—C17B—C16B	180 (2)
C7—C8—C9—N1	−1.7 (4)	C15B—O1B—C18B—C19B	177.8 (12)
C7—C8—C9—C10	178.3 (3)	O3—S1—C21—C22	−48.2 (3)
N1—C9—C10—C11A	178.9 (12)	O2—S1—C21—C22	−168.8 (2)
C8—C9—C10—C11A	−1.0 (12)	O4—S1—C21—C22	71.3 (3)
N1—C9—C10—C11B	173 (2)	O3—S1—C21—C26	134.5 (2)
C8—C9—C10—C11B	−7 (2)	O2—S1—C21—C26	13.9 (3)
C11B—C10—C11A—C12A	−36 (15)	O4—S1—C21—C26	−105.9 (2)
C9—C10—C11A—C12A	−178.3 (12)	C26—C21—C22—C23	2.0 (5)
C10—C11A—C12A—C13A	173.8 (18)	S1—C21—C22—C23	−175.2 (3)
C10—C11A—C12A—C17A	−8 (2)	C21—C22—C23—C24	−0.3 (6)
C17A—C12A—C13A—C14A	4 (2)	C22—C23—C24—F1	178.5 (3)
C11A—C12A—C13A—C14A	−177.8 (15)	C22—C23—C24—C25	−1.1 (6)
C12A—C13A—C14A—C15A	−2 (2)	F1—C24—C25—C26	−178.9 (3)
C18A—O1A—C15A—C14A	179.0 (10)	C23—C24—C25—C26	0.7 (6)
C18A—O1A—C15A—C16A	2.5 (15)	C24—C25—C26—C21	1.1 (4)
C13A—C14A—C15A—O1A	−177.8 (12)	C22—C21—C26—C25	−2.4 (4)
C13A—C14A—C15A—C16A	−1.2 (18)	S1—C21—C26—C25	174.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg4 and Cg5 are the centroids of the C12B–C17B and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.93	2.55	3.456 (4)	166
C8—H8A···O4ⁱⁱ	0.93	2.41	3.306 (3)	161
C10—H10A···O3	0.96	2.55	3.483 (4)	164
C11A—H11A···O4ⁱⁱ	0.93	2.52	3.408 (19)	159
C17A—H17A···O3	0.93	2.58	3.510 (10)	177
C20—H20B···O2ⁱ	0.96	2.53	3.441 (4)	158
C20—H20C···O3	0.96	2.44	3.085 (4)	124
C25—H25A···O4ⁱⁱⁱ	0.93	2.55	3.264 (4)	134
C13A—H13A···Cg5ⁱⁱ	0.93	2.82	3.575 (10)	139
C16A—H16A···Cg5	0.93	2.98	3.826 (9)	151
C19A—H19B···Cg4ⁱⁱⁱ	0.96	2.99	3.862 (11)	152
C13B—H13B···Cg5ⁱⁱ	0.93	2.95	3.765 (16)	147
C16B—H16B···Cg5	0.93	2.70	3.562 (13)	155

Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg4 and Cg5 are the centroids of the C12B–C17B and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.93	2.55	3.456 (4)	166
C8—H8A···O4ⁱⁱ	0.93	2.41	3.306 (3)	161
C10—H10A···O3	0.96	2.55	3.483 (4)	164
C11A—H11A···O4ⁱⁱ	0.93	2.52	3.408 (19)	159
C17A—H17A···O3	0.93	2.58	3.510 (10)	177
C20—H20B···O2ⁱ	0.96	2.53	3.441 (4)	158
C20—H20C···O3	0.96	2.44	3.085 (4)	124
C25—H25A···O4ⁱⁱⁱ	0.93	2.55	3.264 (4)	134
C13A—H13A···Cg5ⁱⁱ	0.93	2.82	3.575 (10)	139
C16A—H16A···Cg5	0.93	2.98	3.826 (9)	151
C19A—H19B···Cg4ⁱⁱⁱ	0.96	2.99	3.862 (11)	152
C13B—H13B···Cg5ⁱⁱ	0.93	2.95	3.765 (16)	147
C16B—H16B···Cg5	0.93	2.70	3.562 (13)	155

Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x−1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank Prince of Songkla University for a research grant. They also thank the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

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Volume 70| Part 1| January 2014| Pages o11-o12

https://doi.org/10.1107/S1600536813032509

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[(E)-2-(4-Eth­­oxy­phen­yl)ethen­yl]-1-methyl­quinolinium 4-fluoro­benzene­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylquinolinium 4-fluorobenzenesulfonate