(E)-2-[4-(Diethyl­amino)­styr­yl]-1-methyl­pyridinium benzene­sulfonate mono­hydrate

Hoong-Kun Fun; Narissara Kaewmanee; Kullapa Chanawanno; Suchada Chantrapromma

doi:10.1107/S1600536811004156

. 2011 Feb 9;67(Pt 3):o593–o594. doi: 10.1107/S1600536811004156

(E)-2-[4-(Diethylamino)styryl]-1-methylpyridinium benzenesulfonate monohydrate

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

PMCID: PMC3051968 PMID: 21522353

Abstract

The asymmetric unit of the title compound, C₁₈H₂₃N₂ ⁺·C₆H₅O₃S⁻·H₂O, comprises a 2-[4-(diethylamino)styryl]-1-methylpyridinium cation, a benzenesulfonate anion and a solvent water molecule. One ethyl substituent of the diethylamino group of the cation is disordered over two positions in a 0.73789 (9):0.26211 (9) ratio. The cation exists in the E configuration with respect to the C=C bond and the π-conjugated system is essentially planar with a dihedral angle of 0.82 (10)° between the pyridinium and benzene rings. The cation and anion are almost orthogonal with a dihedral angle of 86.71 (10)° between the π-conjugated system of the cation and benzene ring of the anion. In the crystal, molecules are arranged into chains along [001] and adjacent chains are linked by weak C—H⋯O interactions. The crystal is further stablilized by O—H⋯O hydrogen bonds and weak C—H⋯π interactions.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For background to and applications of quaternary ammonium compounds, see: Chanawanno et al. (2010 ▶); Fun et al. (2010 ▶); Massi et al. (2003 ▶); Soprey & Maxcy (1968 ▶); Yabuhara et al. (2004 ▶). For related structures, see: Chanawanno et al. (2010 ▶); Kaewmanee et al. (2010 ▶).

Experimental

Crystal data

C₁₈H₂₃N₂ ⁺·C₆H₅O₃S⁻·H₂O
M _r = 442.57
Monoclinic,
a = 9.9393 (5) Å
b = 17.9047 (9) Å
c = 13.2532 (7) Å
β = 100.715 (1)°
V = 2317.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 297 K
0.47 × 0.28 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector. diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.924, T _max = 0.955
23078 measured reflections
6105 independent reflections
3770 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.173
S = 1.04
6105 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 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/S1600536811004156/sj5101sup1.cif

e-67-0o593-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004156/sj5101Isup2.hkl

e-67-0o593-Isup2.hkl^{(298.9KB, hkl)}

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

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

Cg1 is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2ⁱ	0.97	1.91	2.821 (3)	156
O1W—H2W1⋯O1ⁱⁱ	1.07	1.88	2.933 (3)	170
C1—H1A⋯O3ⁱⁱⁱ	0.93	2.26	3.151 (3)	160
C3—H3A⋯O2ⁱⁱ	0.93	2.41	3.335 (4)	178
C4—H4A⋯O1W	0.93	2.50	3.338 (3)	149
C18—H18B⋯O3	0.96	2.45	3.371 (3)	162
C10—H10A⋯Cg1ⁱ	0.93	2.95	3.741 (2)	144

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

Acknowledgments

Financial support by the Prince of Songkla University is gratefully acknowledged. KC thanks the Crystal Materials Research Unit (CMRU), Prince of Songkla University, for the research assistance fellowship. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Quaternary ammonium compounds (QACs) are relatively low toxicity and wide-ranging antimicrobial agents that are commonly used for water treatment, food industry additives and hygienic care for both medical and domestic purposes (Yabuhara et al., 2004). However, due to the long-term usage of common QACs such as benzalkonium chloride and cetylpridinium chloride, QAC resistant microorganisms have appeared. It was reported that some Staphylococcus spp. contain genes conveying resistance to this type of disinfectant (Massi et al., 2003; Soprey et al., 1968; Yabuhara et al., 2004). Therefore, we have developed the novel pyridinium QACs which can overcome this Staphylococcus-resistant phenomenon by exhibiting strong anti-methicillin-resistant Staphylococcus aureus activity and reported this discovery in our previous work (Chanawanno et al., 2010; Fun et al., 2010). The title compound was the one among many pyridinium QACs which was synthesized in our laboratory hoping for a new antibacterial drug candidate. The antibacterial activity of this compound is under investigation and its crystal structure is reported here.

Fig. 1 shows the asymmetric unit of the title compound (I) which consists of the C₁₈H₂₃N₂⁺ cation, C₆H₅O₃S^- anion and one H₂O molecule. The cation exists in the E configuration with respect to the C6═C7 double bond [1.337 (2) Å]. The π-conjugated system of cation (N1/C1–C13) is planar with an r.m.s deviation of 0.0215 (2) Å and the dihedral angle between the C1–C5/N1 pyridinium and the C8–C13 benzene rings is 0.82 (10)° with the torsion angle C5–C6–C7–C8 = -179.19 (17)°. One ethyl unit of the diethylamino moiety is disordered over two positions; the major component A and the minor component B (Fig. 1), with a refined site-occupancy ratio of 0.73789 (9)/0.26211 (9). The diethylamino group deviates from the attached C8–C13 ring and its conformation can be indicated by the torsion angles C11–N2–C14–C15 = 83.8 (4)°, C11–N2–C16–C17 = -95.3 (4)° for the major component A and 106.1 (7)° for the minor component B. The cation and anion are inclined to each other as indicated by the dihedral angle between the π-conjugated system of cation (N1/C1–C13) and the C19–C24 benzene ring of anion being 86.71 (10)°. The bond lengths (Allen et al., 1987) and angles in (I) are in normal ranges and comparable with those for related structures (Chanawanno et al., 2010; Kaewmanee et al., 2010).

In the crystal packing, the cations, anions and water molecules are arranged into individual chains along the [001] direction (Fig. 2). The cations are linked to the anions and water molecules in neighboring chains by C—H···O weak interactions (Table 1 and Fig. 2) whereas the anions are linked to water molecule by O—H···O hydrogen bonds (Table 1). A C—H···π interaction involving the benzenesulfonate anion was observed (Table 1).

Experimental

(E)-2-(4-(diethylamino)styryl)-1-methylpyridinium iodide (compound A, 0.14 g, 0.37 mmol) was prepared by a literature method (Kaewmanee et al., 2010) and then was mixed with silver (I) benzenesulfonate (Chanawanno et al., 2010) (0.10 g, 0.37 mmol) in methanol (100 ml). The mixture immediately yielded a grey precipitate of silver iodide. After stirring the mixture for 30 min, the precipitate of silver iodide was removed and the resulting solution was evaporated yielding the title compound as an orange solid. Orange block-shaped single crystals of the title compound suitable for x-ray structure determination was recrystallized from methanol by slow evaporation of the solvent at room temperature after a few weeks, Mp. 466–468 K.