1-Methyl-4-[(E)-2-(3-hy­droxy-4-meth­oxy­phen­yl)ethen­yl]pyridinium 4-bromo­benzene­sulfonate monohydrate

Chantrapromma, S.; Ruanwas, P.; Jindawong, B.; Fun, H.-K.

doi:10.1107/S1600536813027244

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1623-o1624

doi:10.1107/S1600536813027244

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1-Methyl-4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]pyridinium 4-bromobenzenesulfonate monohydrate

Suchada Chantrapromma,^a ^*‡ Pumsak Ruanwas,^a Boonwasana Jindawong ^a and Hoong-Kun Fun ^b §

^aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 25 September 2013; accepted 3 October 2013; online 9 October 2013)

In the title hydrated salt, C₁₅H₁₆NO₂⁺·C₆H₄BrO₃S⁻·H₂O, the cation exists in an E conformation with respect to the ethenyl bond and is almost planar, with a dihedral angle of 2.62 (12)° between the planes of the pyridinium and benzene rings. The methoxy substituent deviates slightly from the plane of its attached benzene ring [C_methyl—O—C—C torsion angle = −11.6 (6)°]. In the crystal, the cations, anion and water molecules are linked together into chains along [010] by O—H⋯O hydrogen bonds and weak C—H⋯O interactions. There is a short Br⋯O contact [3.029 (2) Å]. The crystal structure also features C—H⋯π interactions involving the benzene ring of the anion.

CCDC reference: 293058

Related literature

For bond-length data, see: Allen et al. (1987 ). For applications of stilbene derivatives, see: Belluti et al. (2010 ); Chanawanno et al. (2010 ); Frombaum et al. (2012 ); Hussain et al. (2009 ); Jindawong et al. (2005 ); Li et al. (2013 ); Ruanwas et al. (2010 ). For related structures, see: Chanawanno et al. (2009 ); Fun et al. (2011 ); Jindawong et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₅H₁₆NO₂⁺·C₆H₄BrO₃S⁻·H₂O
M_r = 496.37
Triclinic, $[P \overline 1]$
a = 9.7426 (7) Å
b = 9.8821 (7) Å
c = 11.8356 (8) Å
α = 80.107 (1)°
β = 73.140 (1)°
γ = 83.297 (1)°
V = 1071.60 (13) Å³
Z = 2
Mo Kα radiation
μ = 2.05 mm⁻¹
T = 100 K
0.54 × 0.51 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.402, T_max = 0.728
5431 measured reflections
3717 independent reflections
3392 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.05
3717 reflections
286 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg₁ is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O4ⁱ	0.80 (5)	2.52 (5)	3.015 (4)	122 (4)
O1W—H1W1⋯O5ⁱ	0.80 (5)	2.22 (5)	3.008 (4)	166 (4)
O1W—H2W1⋯O3	0.82 (5)	2.00 (5)	2.809 (4)	169 (5)
O4—H4A⋯O1Wⁱⁱ	0.79 (4)	1.88 (4)	2.656 (4)	168 (3)
C2—H2A⋯O1ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C5—H5A⋯O4	0.93	2.40	3.241 (3)	150
C18—H18A⋯O1^iv	0.93	2.60	3.476 (5)	158
C10—H10A⋯Cg1^v	0.93	2.78	3.672 (4)	160
C16—H16A⋯Cg1^vi	0.93	2.72	3.543 (3)	148
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) x-1, y, z+1; (v) -x+1, -y, -z+1; (vi) x, y, z+1.

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, PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 293058

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813027244/sj5354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813027244/sj5354Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813027244/sj5354Isup3.cml

checkCIF report

Comment top

The stilbene scaffold is a basic element for a number of biologically active natural and synthetic compounds. Stilbene-based compounds are extensively present in nature and have attracted chemists and biologists because of their wide range of biological activities, acting as antibacterial (Chanawanno et al., 2010), anticancer (Belluti et al., 2010) and antioxidant (Frombaum et al., 2012) agents. In addition, some stilbenes also exhibit non-linear optical (Ruanwas et al., 2010) and fluorescent properties (Li et al., 2013). They are also generally used in the manufacturing industry as whitening agents (Hussain et al., 2009). Due to these interesting properties, the title pyridinium-stilbene (I) was synthesized. We report herein the synthesis and crystal structure of (I).

The asymmetric unit of (I) consists of a C₁₅H₁₆NO₂⁺ cation, a C₆H₄BrSO₃^- anion and a H₂O molecule (Fig. 1). All bond lengths (Allen et al., 1987) and angles in both the cation and anion are normal and compare well with those found in closely related structures (Chanawanno et al., 2009; Fun et al., 2011; Jindawong et al., 2005). The cation exists in an E configuration with respect to the C13 ═C14 double bond [1.326 (5) Å] and the C12—C13—C14—C15 torsion angle is 179.3 (3)°. The cation is essentially planar with a dihedral angle between the pyridinium and benzene rings of the cation of 2.62 (12)°. The hydroxy group lies close to the plane of the C7···C12 benzene ring whereas the methoxy group is slightly twisted from this plane with a C21–O5–C9–C10 torsion angle of -11.6 (6)°. The benzene ring of the 4-bromobenzenesulfonate anion makes dihedral angles of 80.35 (15) and 78.37 (15)° with pyridinium and benzene rings of the cation, respectively.

In the crystal packing (Fig. 2), intermolecular O—H···O hydrogen bonds form between the water molecule (O1W) and the O3 (sulfonate), O4 (hydroxy) and O5 (methoxy) atoms, and between the hydroxy substituent (O4) and the water molecule (O1W) (Table 1). Atoms O1 and O4 are involved in weak intermolecular C—H···O interactions (Table 1). The cations, anions and water molecules are linked into chains along [0 1 0] through these O–H···O and weak C—H···O hydrogen bonds (Fig. 2 and Table 1). The crystal structure is further stabilized by C—H···π interactions involving the centroid of the benzene ring of the cation (Table 1). A short Br···O contact [3.029 (2) Å; symmetry code +x, -1+y, z] also forms between adjacent anions.

Related literature top

For bond-length data, see: Allen et al. (1987). For applications of stilbene derivatives, see: Belluti et al. (2010); Chanawanno et al. (2010); Frombaum et al. (2012); Hussain et al. (2009); Jindawong et al. (2005); Li et al. (2013); Ruanwas et al. (2010). For related structures, see: Chanawanno et al. (2009); Fun et al. (2011); Jindawong et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).

Experimental top

First of all, 1-methyl-4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]pyridinium iodide (compound A) was prepared by mixing a solution (1:1:1 molar ratio) of 1,4-dimethylpyridinium iodide (2.98 g, 12.68 mmol), isovanillin (1.96 g, 12.86 mmol) and piperidine (1.09 g, 12.80 mmol). The resulting solution was refluxed for 3 h under a nitrogen atmosphere. The solid which formed was filtered, washed with diethylether and recrystallized from methanol, to give brown crystals of compound A (3.99 g, 85% yield Mp. 503-504 K). Thereafter, the title compound was synthesized by mixing a solution of compound A (0.21 g, 0.58 mmol) in hot methanol (45 ml) and a solution of silver (I) 4-bromobenzenesulfonate (Jindawong et al., 2005), (0.20 g, 0.58 mmol) in hot methanol (40 ml). The mixture yielded a yellow solid of silver iodide immediately. After stirring the mixture for 20 min, the precipitate of silver iodide was removed and the resulting yellow solution was evaporated to yield the title compound as a yellow solid (0.27 g, 94% yield). Yellow needle-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from ethanol/methanol (1:1 v/v) by slow evaporation of the solvent at room temperature over several days, Mp. 511–512 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids. A hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed approximately along the c axis. Only H atoms involved in O—H···O hydrogen bonds and weak C—H···O interactions are shown for clarity. Hydrogen bonds are drawn as dashed lines.

1-Methyl-4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]pyridinium 4-bromobenzenesulfonate monohydrate top

Crystal data top

C₁₅H₁₆NO₂⁺·C₆H₄BrO₃S⁻·H₂O	Z = 2
M_r = 496.37	F(000) = 508
Triclinic, P1	D_x = 1.538 Mg m⁻³
Hall symbol: -P 1	Melting point = 511–512 K
a = 9.7426 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8821 (7) Å	Cell parameters from 3717 reflections
c = 11.8356 (8) Å	θ = 2.1–25.0°
α = 80.107 (1)°	µ = 2.05 mm⁻¹
β = 73.140 (1)°	T = 100 K
γ = 83.297 (1)°	Needle, yellow
V = 1071.60 (13) Å³	0.54 × 0.51 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3717 independent reflections
Radiation source: sealed tube	3392 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.402, T_max = 0.728	k = −11→11
5431 measured reflections	l = −14→12

Refinement top

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0865P)² + 0.2408P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3717 reflections	Δρ_max = 0.59 e Å⁻³
286 parameters	Δρ_min = −0.82 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

Crystal data top

C₁₅H₁₆NO₂⁺·C₆H₄BrO₃S⁻·H₂O	γ = 83.297 (1)°
M_r = 496.37	V = 1071.60 (13) Å³
Triclinic, P1	Z = 2
a = 9.7426 (7) Å	Mo Kα radiation
b = 9.8821 (7) Å	µ = 2.05 mm⁻¹
c = 11.8356 (8) Å	T = 100 K
α = 80.107 (1)°	0.54 × 0.51 × 0.16 mm
β = 73.140 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3717 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3392 reflections with I > 2σ(I)
T_min = 0.402, T_max = 0.728	R_int = 0.027
5431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.59 e Å⁻³
3717 reflections	Δρ_min = −0.82 e Å⁻³
286 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
Br1	0.33252 (3)	−0.08552 (3)	0.17801 (3)	0.05706 (18)
S1	0.31851 (7)	0.54351 (6)	0.25594 (6)	0.0432 (2)
O1	0.3962 (3)	0.6148 (2)	0.14279 (19)	0.0682 (7)
O2	0.3892 (3)	0.5389 (2)	0.3481 (2)	0.0690 (6)
O3	0.1683 (2)	0.5911 (2)	0.2912 (3)	0.0717 (7)
O4	0.0748 (2)	0.0170 (3)	0.57781 (19)	0.0612 (6)
H4A	0.021 (4)	0.083 (4)	0.573 (3)	0.060 (10)*
O5	0.3044 (3)	−0.1435 (3)	0.5684 (2)	0.0673 (7)
N1	−0.1966 (3)	0.4820 (3)	1.2500 (2)	0.0552 (6)
C1	0.3205 (3)	0.3703 (3)	0.2328 (2)	0.0370 (5)
C2	0.3903 (3)	0.3303 (3)	0.1220 (2)	0.0397 (5)
H2A	0.4362	0.3947	0.0595	0.048*
C3	0.3917 (3)	0.1959 (3)	0.1045 (2)	0.0413 (6)
H3A	0.4375	0.1692	0.0303	0.050*
C4	0.3239 (3)	0.1009 (3)	0.1991 (2)	0.0414 (6)
C5	0.2534 (3)	0.1391 (3)	0.3101 (2)	0.0473 (6)
H5A	0.2081	0.0745	0.3728	0.057*
C6	0.2516 (3)	0.2742 (3)	0.3261 (2)	0.0434 (6)
H6A	0.2040	0.3013	0.3999	0.052*
C7	0.0825 (3)	0.0955 (3)	0.7566 (2)	0.0459 (6)
H7A	−0.0007	0.1528	0.7583	0.055*
C8	0.1366 (3)	0.0180 (3)	0.6658 (2)	0.0450 (6)
C9	0.2618 (3)	−0.0698 (3)	0.6621 (3)	0.0512 (7)
C10	0.3307 (3)	−0.0750 (4)	0.7487 (3)	0.0607 (8)
H10A	0.4147	−0.1313	0.7460	0.073*
C11	0.2752 (4)	0.0035 (4)	0.8403 (3)	0.0630 (9)
H11A	0.3226	−0.0016	0.8988	0.076*
C12	0.1506 (3)	0.0898 (3)	0.8470 (2)	0.0483 (7)
C13	0.0935 (3)	0.1690 (3)	0.9448 (3)	0.0536 (7)
H13A	0.1457	0.1596	1.0006	0.064*
C14	−0.0245 (3)	0.2534 (3)	0.9641 (3)	0.0518 (7)
H14A	−0.0767	0.2641	0.9082	0.062*
C15	−0.0802 (3)	0.3305 (3)	1.0634 (2)	0.0482 (6)
C16	−0.0137 (3)	0.3290 (4)	1.1535 (3)	0.0601 (8)
H16A	0.0721	0.2758	1.1515	0.072*
C17	−0.0727 (4)	0.4041 (4)	1.2442 (3)	0.0621 (8)
H17A	−0.0265	0.4016	1.3032	0.074*
C18	−0.2637 (4)	0.4864 (4)	1.1655 (3)	0.0610 (8)
H18A	−0.3492	0.5408	1.1698	0.073*
C19	−0.2093 (3)	0.4127 (4)	1.0733 (3)	0.0580 (8)
H19A	−0.2585	0.4169	1.0160	0.070*
C20	−0.2569 (5)	0.5637 (4)	1.3496 (3)	0.0757 (10)
H20A	−0.3572	0.5877	1.3571	0.114*
H20B	−0.2069	0.6460	1.3336	0.114*
H20C	−0.2456	0.5101	1.4225	0.114*
C21	0.4426 (4)	−0.2138 (5)	0.5445 (4)	0.0830 (12)
H21A	0.4610	−0.2535	0.4725	0.125*
H21B	0.4467	−0.2854	0.6097	0.125*
H21C	0.5137	−0.1501	0.5350	0.125*
O1W	0.0853 (3)	0.7571 (3)	0.4734 (2)	0.0615 (6)
H1W1	0.143 (5)	0.796 (5)	0.490 (4)	0.087 (16)*
H2W1	0.120 (5)	0.706 (5)	0.423 (4)	0.082 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0620 (3)	0.0341 (2)	0.0688 (3)	−0.01219 (14)	−0.00293 (16)	−0.01084 (14)
S1	0.0501 (4)	0.0321 (4)	0.0444 (4)	−0.0052 (3)	−0.0061 (3)	−0.0074 (3)
O1	0.1028 (18)	0.0350 (11)	0.0525 (12)	−0.0186 (11)	0.0039 (11)	−0.0027 (9)
O2	0.0927 (18)	0.0552 (13)	0.0709 (14)	−0.0150 (12)	−0.0346 (13)	−0.0139 (11)
O3	0.0546 (14)	0.0496 (13)	0.1069 (18)	0.0051 (11)	−0.0082 (12)	−0.0308 (12)
O4	0.0587 (13)	0.0770 (16)	0.0564 (13)	0.0155 (12)	−0.0285 (10)	−0.0243 (11)
O5	0.0547 (13)	0.0828 (17)	0.0703 (14)	0.0182 (12)	−0.0225 (11)	−0.0339 (12)
N1	0.0515 (14)	0.0595 (16)	0.0491 (13)	−0.0117 (12)	−0.0023 (11)	−0.0081 (11)
C1	0.0358 (12)	0.0314 (12)	0.0415 (13)	−0.0042 (9)	−0.0072 (10)	−0.0035 (10)
C2	0.0385 (13)	0.0331 (13)	0.0404 (13)	−0.0050 (10)	−0.0029 (10)	0.0011 (10)
C3	0.0414 (13)	0.0413 (14)	0.0374 (12)	−0.0029 (11)	−0.0031 (10)	−0.0088 (10)
C4	0.0395 (13)	0.0308 (12)	0.0504 (14)	−0.0062 (10)	−0.0066 (11)	−0.0044 (10)
C5	0.0489 (15)	0.0361 (14)	0.0483 (15)	−0.0130 (11)	−0.0004 (12)	0.0010 (11)
C6	0.0436 (14)	0.0439 (14)	0.0362 (12)	−0.0063 (11)	0.0008 (10)	−0.0065 (11)
C7	0.0360 (13)	0.0552 (16)	0.0451 (14)	−0.0043 (11)	−0.0100 (11)	−0.0046 (12)
C8	0.0405 (14)	0.0519 (16)	0.0424 (14)	−0.0059 (11)	−0.0114 (11)	−0.0049 (11)
C9	0.0434 (15)	0.0558 (17)	0.0542 (16)	−0.0043 (13)	−0.0131 (12)	−0.0074 (13)
C10	0.0456 (16)	0.073 (2)	0.067 (2)	0.0074 (15)	−0.0225 (15)	−0.0151 (16)
C11	0.0545 (18)	0.082 (2)	0.0612 (19)	0.0042 (16)	−0.0302 (15)	−0.0147 (17)
C12	0.0418 (14)	0.0584 (18)	0.0457 (14)	−0.0108 (13)	−0.0127 (11)	−0.0045 (12)
C13	0.0492 (16)	0.069 (2)	0.0475 (15)	−0.0099 (14)	−0.0185 (13)	−0.0073 (14)
C14	0.0492 (16)	0.0628 (19)	0.0464 (15)	−0.0109 (14)	−0.0160 (12)	−0.0062 (13)
C15	0.0410 (14)	0.0563 (17)	0.0451 (14)	−0.0122 (12)	−0.0089 (11)	−0.0003 (13)
C16	0.0465 (16)	0.081 (2)	0.0544 (17)	0.0015 (15)	−0.0150 (13)	−0.0177 (16)
C17	0.0539 (18)	0.081 (2)	0.0534 (17)	−0.0055 (16)	−0.0158 (14)	−0.0145 (16)
C18	0.0500 (17)	0.067 (2)	0.0607 (18)	−0.0004 (15)	−0.0111 (14)	−0.0061 (15)
C19	0.0522 (17)	0.071 (2)	0.0527 (17)	−0.0032 (15)	−0.0192 (14)	−0.0075 (15)
C20	0.080 (2)	0.079 (3)	0.064 (2)	−0.005 (2)	−0.0029 (18)	−0.0287 (19)
C21	0.064 (2)	0.090 (3)	0.095 (3)	0.023 (2)	−0.022 (2)	−0.036 (2)
O1W	0.0623 (14)	0.0660 (15)	0.0545 (13)	0.0033 (12)	−0.0109 (11)	−0.0183 (11)

Geometric parameters (Å, º) top

Br1—C4	1.890 (3)	C9—C10	1.370 (4)
S1—O1	1.440 (2)	C10—C11	1.386 (5)
S1—O2	1.441 (2)	C10—H10A	0.9300
S1—O3	1.445 (2)	C11—C12	1.390 (4)
S1—C1	1.777 (2)	C11—H11A	0.9300
O4—C8	1.348 (3)	C12—C13	1.448 (4)
O4—H4A	0.79 (4)	C13—C14	1.326 (5)
O5—C9	1.369 (4)	C13—H13A	0.9300
O5—C21	1.416 (4)	C14—C15	1.449 (4)
N1—C18	1.338 (4)	C14—H14A	0.9300
N1—C17	1.344 (4)	C15—C16	1.397 (4)
N1—C20	1.483 (4)	C15—C19	1.402 (4)
C1—C6	1.390 (4)	C16—C17	1.361 (5)
C1—C2	1.391 (4)	C16—H16A	0.9300
C2—C3	1.377 (4)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C19	1.359 (5)
C3—C4	1.388 (4)	C18—H18A	0.9300
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.389 (4)	C20—H20A	0.9600
C5—C6	1.377 (4)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—H6A	0.9300	C21—H21A	0.9600
C7—C8	1.371 (4)	C21—H21B	0.9600
C7—C12	1.404 (4)	C21—H21C	0.9600
C7—H7A	0.9300	O1W—H1W1	0.80 (5)
C8—C9	1.406 (4)	O1W—H2W1	0.81 (4)

O1—S1—O2	112.81 (16)	C10—C11—C12	121.9 (3)
O1—S1—O3	112.92 (16)	C10—C11—H11A	119.1
O2—S1—O3	113.31 (16)	C12—C11—H11A	119.1
O1—S1—C1	105.43 (12)	C11—C12—C7	117.4 (3)
O2—S1—C1	106.15 (12)	C11—C12—C13	120.8 (3)
O3—S1—C1	105.34 (12)	C7—C12—C13	121.8 (3)
C8—O4—H4A	111 (3)	C14—C13—C12	127.6 (3)
C9—O5—C21	118.7 (3)	C14—C13—H13A	116.2
C18—N1—C17	119.8 (3)	C12—C13—H13A	116.2
C18—N1—C20	120.5 (3)	C13—C14—C15	126.5 (3)
C17—N1—C20	119.6 (3)	C13—C14—H14A	116.7
C6—C1—C2	119.9 (2)	C15—C14—H14A	116.7
C6—C1—S1	119.64 (19)	C16—C15—C19	116.0 (3)
C2—C1—S1	120.50 (19)	C16—C15—C14	124.2 (3)
C3—C2—C1	120.3 (2)	C19—C15—C14	119.8 (3)
C3—C2—H2A	119.8	C17—C16—C15	120.9 (3)
C1—C2—H2A	119.8	C17—C16—H16A	119.5
C2—C3—C4	119.1 (2)	C15—C16—H16A	119.5
C2—C3—H3A	120.4	N1—C17—C16	121.1 (3)
C4—C3—H3A	120.4	N1—C17—H17A	119.4
C3—C4—C5	121.3 (2)	C16—C17—H17A	119.4
C3—C4—Br1	119.4 (2)	N1—C18—C19	121.2 (3)
C5—C4—Br1	119.21 (19)	N1—C18—H18A	119.4
C6—C5—C4	119.0 (2)	C19—C18—H18A	119.4
C6—C5—H5A	120.5	C18—C19—C15	121.0 (3)
C4—C5—H5A	120.5	C18—C19—H19A	119.5
C5—C6—C1	120.4 (2)	C15—C19—H19A	119.5
C5—C6—H6A	119.8	N1—C20—H20A	109.5
C1—C6—H6A	119.8	N1—C20—H20B	109.5
C8—C7—C12	121.1 (3)	H20A—C20—H20B	109.5
C8—C7—H7A	119.5	N1—C20—H20C	109.5
C12—C7—H7A	119.5	H20A—C20—H20C	109.5
O4—C8—C7	123.9 (2)	H20B—C20—H20C	109.5
O4—C8—C9	115.8 (2)	O5—C21—H21A	109.5
C7—C8—C9	120.3 (2)	O5—C21—H21B	109.5
O5—C9—C10	125.6 (3)	H21A—C21—H21B	109.5
O5—C9—C8	115.0 (2)	O5—C21—H21C	109.5
C10—C9—C8	119.4 (3)	H21A—C21—H21C	109.5
C9—C10—C11	120.0 (3)	H21B—C21—H21C	109.5
C9—C10—H10A	120.0	H1W1—O1W—H2W1	115 (4)
C11—C10—H10A	120.0

O1—S1—C1—C6	−179.1 (2)	C7—C8—C9—C10	−1.3 (5)
O2—S1—C1—C6	61.0 (2)	O5—C9—C10—C11	−179.0 (3)
O3—S1—C1—C6	−59.5 (2)	C8—C9—C10—C11	1.4 (5)
O1—S1—C1—C2	0.9 (3)	C9—C10—C11—C12	−0.5 (6)
O2—S1—C1—C2	−119.0 (2)	C10—C11—C12—C7	−0.4 (5)
O3—S1—C1—C2	120.5 (2)	C10—C11—C12—C13	178.9 (3)
C6—C1—C2—C3	−0.1 (4)	C8—C7—C12—C11	0.5 (4)
S1—C1—C2—C3	179.9 (2)	C8—C7—C12—C13	−178.8 (3)
C1—C2—C3—C4	−0.6 (4)	C11—C12—C13—C14	−178.9 (3)
C2—C3—C4—C5	0.8 (4)	C7—C12—C13—C14	0.4 (5)
C2—C3—C4—Br1	−177.19 (19)	C12—C13—C14—C15	179.3 (3)
C3—C4—C5—C6	−0.2 (4)	C13—C14—C15—C16	1.6 (5)
Br1—C4—C5—C6	177.8 (2)	C13—C14—C15—C19	−178.1 (3)
C4—C5—C6—C1	−0.6 (4)	C19—C15—C16—C17	−0.3 (5)
C2—C1—C6—C5	0.8 (4)	C14—C15—C16—C17	−179.9 (3)
S1—C1—C6—C5	−179.3 (2)	C18—N1—C17—C16	0.0 (5)
C12—C7—C8—O4	178.7 (3)	C20—N1—C17—C16	−179.4 (4)
C12—C7—C8—C9	0.4 (5)	C15—C16—C17—N1	0.1 (6)
C21—O5—C9—C10	−11.6 (6)	C17—N1—C18—C19	0.3 (5)
C21—O5—C9—C8	168.1 (3)	C20—N1—C18—C19	179.6 (3)
O4—C8—C9—O5	0.6 (4)	N1—C18—C19—C15	−0.5 (6)
C7—C8—C9—O5	179.0 (3)	C16—C15—C19—C18	0.5 (5)
O4—C8—C9—C10	−179.8 (3)	C14—C15—C19—C18	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg₁ is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4ⁱ	0.80 (5)	2.52 (5)	3.015 (4)	122 (4)
O1W—H1W1···O5ⁱ	0.80 (5)	2.22 (5)	3.008 (4)	166 (4)
O1W—H2W1···O3	0.82 (5)	2.00 (5)	2.809 (4)	169 (5)
O4—H4A···O1Wⁱⁱ	0.79 (4)	1.88 (4)	2.656 (4)	168 (3)
C2—H2A···O1ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C5—H5A···O4	0.93	2.40	3.241 (3)	150
C18—H18A···O1^iv	0.93	2.60	3.476 (5)	158
C10—H10A···Cg1^v	0.93	2.78	3.672 (4)	160
C16—H16A···Cg1^vi	0.93	2.72	3.543 (3)	148

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

Hydrogen-bond geometry (Å, º) top

Cg₁ is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O4ⁱ	0.80 (5)	2.52 (5)	3.015 (4)	122 (4)
O1W—H1W1···O5ⁱ	0.80 (5)	2.22 (5)	3.008 (4)	166 (4)
O1W—H2W1···O3	0.82 (5)	2.00 (5)	2.809 (4)	169 (5)
O4—H4A···O1Wⁱⁱ	0.79 (4)	1.88 (4)	2.656 (4)	168 (3)
C2—H2A···O1ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C5—H5A···O4	0.93	2.40	3.241 (3)	150
C18—H18A···O1^iv	0.93	2.60	3.476 (5)	158
C10—H10A···Cg1^v	0.93	2.78	3.672 (4)	160
C16—H16A···Cg1^vi	0.93	2.72	3.543 (3)	148

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Prince of Songkla University for generous support. The authors also thank the Universiti Sains Malaysia for the APEX DE2012 (grant No. 1002/PFIZIK/910323).

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Volume 69| Part 11| November 2013| Pages o1623-o1624

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

1-Methyl-4-[(E)-2-(3-hy­dr­oxy-4-meth­­oxy­phen­yl)ethen­yl]pyridinium 4-bromo­benzene­sulfonate monohydrate

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organic compounds

1-Methyl-4-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]pyridinium 4-bromobenzenesulfonate monohydrate