1-Methyl-2-[(E)-2,4,5-trimeth­oxy­styr­yl]pyridinium 4-meth­oxy­benzene­sulfonate monohydrate

Hoong-Kun Fun; Charoensak Mueangkeaw; Pumsak Ruanwas; Suchada Chantrapromma

doi:10.1107/S1600536811008610

. 2011 Mar 12;67(Pt 4):o867–o868. doi: 10.1107/S1600536811008610

1-Methyl-2-[(E)-2,4,5-trimethoxystyryl]pyridinium 4-methoxybenzenesulfonate monohydrate

Hoong-Kun Fun ^a,^*,^‡, Charoensak Mueangkeaw ^b, Pumsak Ruanwas ^b, Suchada Chantrapromma ^b,^§

PMCID: PMC3100012 PMID: 21754147

Abstract

In the title compound, C₁₇H₂₀NO₃ ⁺·C₇H₇O₄S⁻·H₂O, the cation exists in an E configuration with respect to the C=C bond and is twisted with a dihedral angle of 17.81 (8)° between the pyridinium and benzene rings. The benzene ring of the anion is almost parallel to the pyridinium ring [dihedral angle = 3.45 (9)°], whereas it is inclined to the benzene ring of the cation [dihedral angle = 17.62 (8)°]. The crystal structure is stabilized by O—H⋯O hydrogen bonds and weak C—H⋯O interactions which link the cations, anions and water molecules into chains along the a axis. π–π interactions with centroid–centroid distances of 3.7751 (9) and 3.7920 (11) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the non-linear optical properties and applications of pyridinium and quinolinium derivatives, see: Chanawanno et al. (2010 ▶), Chantrapromma et al. (2010 ▶); Fun et al. (2009 ▶); Ruanwas et al. (2010 ▶); Williams (1984 ▶). For related structures, see, Chantrapromma et al. (2007 ▶); Mueangkeaw et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₁₇H₂₀NO₃ ⁺·C₇H₇O₄S⁻·H₂O
M _r = 491.55
Triclinic,
a = 6.8463 (4) Å
b = 10.8855 (5) Å
c = 15.8137 (8) Å
α = 83.950 (2)°
β = 81.355 (2)°
γ = 81.140 (2)°
V = 1147.14 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.40 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.927, T _max = 0.989
20386 measured reflections
5219 independent reflections
4534 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.124
S = 1.05
5219 reflections
320 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536811008610/rz2563sup1.cif

e-67-0o867-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008610/rz2563Isup2.hkl

e-67-0o867-Isup2.hkl^{(255.6KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O6	0.80 (3)	2.08 (3)	2.8703 (19)	175 (3)
O1W—H1W1⋯O5ⁱ	0.85 (3)	1.98 (3)	2.8233 (19)	173 (2)
C9—H9A⋯O4	0.93	2.53	3.445 (2)	167
C14—H14A⋯O1Wⁱⁱ	0.96	2.32	3.262 (2)	168
C14—H14C⋯O1ⁱⁱⁱ	0.96	2.54	3.487 (2)	168
C16—H16A⋯O7^iv	0.96	2.53	3.388 (2)	149
C16—H16B⋯O5ⁱⁱⁱ	0.96	2.54	3.408 (2)	150
C16—H16C⋯O6^v	0.96	2.44	3.371 (2)	163
C17—H17C⋯O4ⁱⁱⁱ	0.96	2.47	3.419 (2)	168
C18—H18A⋯O1W^vi	0.93	2.43	3.354 (2)	171
C22—H22A⋯O2^iv	0.93	2.36	3.281 (2)	170

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

Acknowledgments

CM thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. Financial support from the Prince of Songkla University is acknowledged. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Within the frame of our on-going research on non-linear optic (NLO) materials and antibacterial compounds, we have synthesized several pyridinium and quinolinium derivatives, and their NLO properties and antibacterial activities have been reported (Chanawanno et al., 2010; Chantrapromma et al., 2007; Fun et al., 2009; Ruanwas et al., 2010). As part of this research the title pyridinium derivative, (I), was synthesized and its crystal structure is herein reported. The title compound crystallizes in the centrosymmetric triclinic P1 space group and therefore it does not exhibit second order NLO properties (Williams, 1984). In addition, (I) was also tested for antibacterial activities against Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei, and it was found to be inactive.

Fig. 1 shows the asymmetric unit of (I) which consists of a C₁₇H₂₀NO₃⁺ cation, a C₇H₇O₄S^- anion and a water solvent molecule. The cation exists in the E configuration with respect to the C6═C7 double bond [1.352 (2) Å] with the torsion angle C5–C6–C7–C8 = -174.98 (16)°. The cation is twisted with the dihedral angle between the pyridinium and benzene rings of 17.81 (8)°. One of the three methoxy substituent of the 2,4,5-trimethoxyphenyl ring is twisted whereas the other two are essentially co-planar with torsion angles of 6.4 (2), 1.7 (2) and 0.7 (2)° for C15–O1–C10–C9, C16–O2–C11–C12 and C17–O3–C13–C12, respectively. The methyl groups of two methoxy substituents at atoms C11 and C13 point toward whereas at atoms C10 and C11 point away from each other (Fig. 1) due to the steric effect of their positions. In the anion, the methoxy group is co-planar with the benzene ring forming a torsion angle C24–O7–C23–C18 = 1.2 (2)°. The benzene ring of the anion is almost parallel to the pyridinium ring (dihedral angle 3.45 (9)°), whereas it is inclined to the benzene ring of the cation at 17.62 (8)°. The bond lengths of (I) are in normal ranges (Allen et al., 1987) and comparable to those found in related structures (Chantrapromma et al., 2010; Mueangkeaw et al., 2010).

In the crystal packing, the cations are linked to both anions and water molecules by weak C—H···O interactions, and the anions are linked to water molecules by O—H···O hydrogen bonds to form chains along the a axis (Table 1, Fig. 2). π–π interactions are observed with centroid-to-centroid distances Cg₁···Cg₂ⁱ = 3.7920 (11) Å and Cg₃···Cg₃ⁱⁱ = 3.775 (9) Å; Cg₁, Cg₂ and Cg₃ are the centroids of the N1/C1–C5, C18–C23 and C8–C13 rings, respectively (symmetry codes: (i) x, -1+y, z; (ii) = 2-x, -y, 1-z).

Experimental

1-Methyl-2-[(E)-2,4,5-trimethoxystyryl]pyridinium iodide (compound A) was prepared according to the previously reported method (Mueangkeaw et al.,2010). Silver(I) 4-methoxybenzenesulfonate (compound B) was synthesized by following the previous procedure (Chantrapromma et al.,2007). The title compound was prepared by mixing a 1:1 molar ratio of compound A (0.100 g, 0.24 mmol) and compound B (0.071 g, 0.24 mmol) in hot CH₃OH (50 ml). The mixture immediately yielded a grey precipitate of silver iodide. After stirring the mixture for ca. 30 min, the precipitate was removed and the resulting solution was evaporated yielding an orange viscous oil. Orange needle-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from DMSO by slow evaporation at room temperature over a few weeks, M.p. 453-454 K.