2-[(E)-2-(4-Eth­oxy­phen­yl)ethen­yl]-1-methyl­pyridinium 4-chloro­benzene­sulfonate monohydrate

Suchada Chantrapromma; Kullapa Chanawanno; Hoong-Kun Fun

doi:10.1107/S1600536810053572

. 2011 Jan 29;67(Pt 2):o515–o516. doi: 10.1107/S1600536810053572

2-[(E)-2-(4-Ethoxyphenyl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate monohydrate¹

Suchada Chantrapromma ^a,^‡, Kullapa Chanawanno ^a, Hoong-Kun Fun ^b,^§

PMCID: PMC3051682 PMID: 21523166

Abstract

In the title compound, C₁₆H₁₈NO⁺·C₆H₄ClO₃S⁻·H₂O, the cation exists in an E configuration with respect to the ethenyl bond and is slightly twisted with a dihedral angle of 9.85 (5)° between the pyridinium and the benzene rings. The anion is inclined to the cation with the dihedral angles between the benzene ring of the anion and the pyridinium and benzene rings of the cation of 78.33 (6) and 68.73 (6)°, respectively. In the crystal, the cations and anions are arranged alternately into head-to-head ribbons along the c axis, with the cationic ribbons stacked along the b axis. The crystal is consolidated by O—H⋯O hydrogen bonds, weak C—H⋯O and C—H⋯π interactions. π–π interactions with centroid–centroid distances of 3.6111 (7) and 3.6466 (7) Å are also observed.

Related literature

For background to and the biological activity of quaternary ammonium compounds, see: Armitage et al. (1929 ▶); Browning et al. (1922 ▶); Chanawanno et al. (2010 ▶); Chantrapromma et al. (2010 ▶); Wainwright & Kristiansen (2003 ▶). For related structures, see: Fun 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

C₁₆H₁₈NO⁺·C₆H₄ClO₃S⁻·H₂O
M _r = 449.94
Monoclinic,
a = 9.7568 (5) Å
b = 6.5284 (3) Å
c = 34.6568 (15) Å
β = 104.784 (1)°
V = 2134.43 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.45 × 0.32 × 0.13 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.873, T _max = 0.962
30082 measured reflections
7670 independent reflections
6483 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.141
S = 1.11
7670 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.60 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053572/rz2539sup1.cif

e-67-0o515-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053572/rz2539Isup2.hkl

e-67-0o515-Isup2.hkl^{(375.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg3 are the centroids of the C8–C13 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4ⁱ	0.91	1.95	2.8148 (16)	158
O1W—H2W1⋯O2	0.82	2.11	2.9265 (14)	173
C1—H1A⋯O1Wⁱⁱ	0.93	2.23	3.1544 (17)	176
C2—H2A⋯O1Wⁱⁱⁱ	0.93	2.44	3.2200 (17)	142
C4—H4A⋯O2ⁱ	0.93	2.50	3.3768 (17)	158
C6—H6A⋯O3^iv	0.93	2.56	3.4308 (17)	155
C13—H13A⋯O3^iv	0.93	2.51	3.3859 (17)	157
C16—H16A⋯O4^v	0.96	2.57	3.3766 (18)	142
C16—H16B⋯O3^iv	0.96	2.50	3.1307 (17)	124
C22—H22A⋯O4	0.93	2.56	2.9246 (17)	104
C9—H9A⋯Cg3ⁱ	0.93	2.90	3.5924 (13)	132
C12—H12A⋯Cg3^iv	0.93	2.96	3.7431 (13)	143
C15—H15C⋯Cg2^vi	0.96	2.87	3.6918 (14)	145

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors thank the Prince of Songkla University for a research grant. They also thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Various quaternary ammonium compounds, such as styryl pyridinium derivatives, exhibit antiseptic properties (Armitage et al., 1929; Browning et al., 1922; Wainwright & Kristiansen, 2003). From our previous investigation on bioactive styryl pyridinium compounds, we found that dimethylaminostyryl pyridinium 4-substituted-benzenesulfonates possess high activity against both susceptible and methicillin-resistant Staphylococcus aureus (MRSA) (Chanawanno et al., 2010). In continuing our on-going research on biologically-active quaternary ammonium compounds (Chanawanno et al., 2010; Chantrapromma et al., 2010), the title pyridinium derivative (I) was synthesized. Our results show that (I) is moderately active against the MRSA with the MIC value = 75 µg/ml, whereas it is inactive against susceptible Staphylococcus aureus. Herein we report the crystal structure of (I).

In the title compound (Fig. 1), the cation exists in an E configuration with respect to the ethenyl bond [torsion angle C5—C6—C7—C8 = 179.53 (11)°]. The cation is slightly twisted with a dihedral angle between the N1/C1–C5 pyridinium and C8–C13 benzene rings of 9.85 (5)°. The ethoxy group is slightly twisted from the mean plane of the attached benzene ring with the torsion angle C11–O1–C14–C15 = -174.84 (10)°. The 4-chlorobenzenesulfonate anion is inclined to the cation as indicated by the dihedral angles between the benzene ring of the anion and the pyridinium and benzene rings of the cation of 78.33 (6) and 68.73 (6)°, respectively. The water molecule forms an O—H···O hydrogen bond with the anion (Table 1). Bond distances in (I) have normal values (Allen et al., 1987) and are comparable to those observed in a related structure (Fun et al., 2010).

In the crystal (Fig. 2), cations and anions are arranged alternatively into head-to-head ribbons along the c axis, with the cationic ribbons stacked along the b axis. The water molecules are linked to the anions by O—H···O hydrogen bonds and to the cations by C—H···O weak interactions. The crystal is consolidated by O—H···O hydrogen bonds, weak C—H···O and C—H···π interactions (Table 1). π–π interactions with distances Cg₁···Cg₁ = 3.6466 (7) Å (symmetry code; 2-x, 2-y, 1-z) and Cg₁···Cg₂ = 3.6466 (7) Å (symmetry code; x, 1+y, z) are observed (Cg₁, Cg₂ and Cg₃ are the centroids of N1/C1–C5, C8–C13 and C17–C22 rings, respectively).

Experimental

The title compound was prepared according to our reported procedure (Chanawanno et al., 2010). Yellow block-shaped single crystal 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. M. p. 458-459 K.