1-Methyl-4-[(E)-2-(3-hy-droxy-4-meth-oxy-phen-yl)ethen-yl]pyridinium 4-bromo-benzene-sulfonate monohydrate.

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 meth-oxy substituent deviates slightly from the plane of its attached benzene ring [Cmeth-yl-O-C-C torsion angle = -11.6 (6)°]. In the crystal, the cations, anion and water mol-ecules are linked together into chains along [010] by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions. There is a short Br⋯O contact [3.029 (2) Å]. The crystal structure also features C-H⋯π inter-actions involving the benzene ring of the anion.

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 = 496.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.05

3717 reflections

286 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.82 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027244/sj5354sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027244/sj5354Isup3.cml

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

C15H16NO2+·C6H4BrO3S−·H2O	Z = 2
Mr = 496.37	F(000) = 508
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0865P)2 + 0.2408P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3717 reflections	Δρmax = 0.59 e Å−3
286 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	0.93	2.60	3.476 (5)	158
C10—H10A···Cg1v	0.93	2.78	3.672 (4)	160
C16—H16A···Cg1vi	0.93	2.72	3.543 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg 1 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⋯O1W ii	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⋯O1iv	0.93	2.60	3.476 (5)	158
C10—H10A⋯Cg1v	0.93	2.78	3.672 (4)	160
C16—H16A⋯Cg1vi	0.93	2.72	3.543 (3)	148

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