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

The title salt crystallized as the monohydrate C15H16NO2 (+)·C6H4BrSO3 (-)·H2O. The cation exists in an E conformation with respect to the ethynyl bond and is essentially planar, with a dihedral angle of 6.52 (14)° between the pyridinium and the benzene rings. The hy-droxy and meth-oxy substituents are coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0116 (3) Å for the nine non-H atoms [Cmeth-yl-O-C-C torsion angle = -0.8 (4)°]. In the crystal, the cations and anions are stacked by π-π inter-actions, with centroid-centroid distances of 3.7818 (19) and 3.9004 (17) Å. The cations, anions and water mol-ecules are linked by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For applications of stilbene derivatives, see: Chanawanno et al. (2010 ▶); Frombaum et al. (2012 ▶); Hussain et al. (2009 ▶); Jindawong et al. (2005 ▶); Kobkeatthawin et al. (2009 ▶); Li et al. (2013 ▶); Ruanwas et al. (2010 ▶). For related structures, see, Chanawanno et al. (2009 ▶); Chantrapromma et al. (2013 ▶); Fun et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). 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 = 9.8201 (13) Å

b = 10.3315 (14) Å

c = 12.4914 (17) Å

α = 99.898 (2)°

β = 111.134 (2)°

γ = 107.042 (2)°

V = 1074.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.05 mm−1

T = 100 K

0.59 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.378, T max = 0.768

11172 measured reflections

4186 independent reflections

3356 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.05

4186 reflections

281 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.93 e Å−3

Δρmin = −0.94 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031917/sj5370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031917/sj5370Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031917/sj5370Isup3.cml

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

C15H16NO2+·C6H4BrO3S−·H2O	Z = 2
Mr = 496.37	F(000) = 508
Triclinic, P1	Dx = 1.535 Mg m−3
Hall symbol: -P 1	Melting point = 490–491 K
a = 9.8201 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3315 (14) Å	Cell parameters from 4186 reflections
c = 12.4914 (17) Å	θ = 1.8–26.0°
α = 99.898 (2)°	µ = 2.05 mm−1
β = 111.134 (2)°	T = 100 K
γ = 107.042 (2)°	Block, orange
V = 1074.1 (3) Å3	0.59 × 0.15 × 0.14 mm

Bruker APEXII CCD area-detector diffractometer	4186 independent reflections
Radiation source: sealed tube	3356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.378, Tmax = 0.768	k = −12→12
11172 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.8763P] where P = (Fo2 + 2Fc2)/3
4186 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.94 e Å−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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.41562 (5)	0.27735 (5)	0.15160 (5)	0.0940 (2)
S1	1.07185 (8)	0.19371 (9)	0.35750 (8)	0.0644 (2)
O1	−0.2430 (2)	0.1320 (2)	−0.12616 (19)	0.0664 (6)
O2	−0.4997 (2)	0.1780 (2)	−0.22714 (18)	0.0617 (5)
H1O2	−0.5807	0.1942	−0.2456	0.092*
O3	1.0331 (3)	0.0475 (3)	0.3536 (3)	0.1036 (10)
O4	1.1634 (3)	0.2910 (3)	0.4784 (2)	0.1020 (9)
O5	1.1441 (3)	0.2289 (3)	0.2791 (3)	0.0922 (8)
N1	0.3889 (2)	0.6912 (2)	0.43554 (19)	0.0449 (5)
C1	0.4991 (3)	0.7901 (3)	0.5431 (2)	0.0542 (7)
H1A	0.5957	0.7823	0.5812	0.065*
C2	0.4719 (4)	0.8995 (3)	0.5961 (3)	0.0566 (7)
H2A	0.5483	0.9660	0.6698	0.068*
C3	0.3287 (4)	0.9101 (3)	0.5387 (3)	0.0586 (7)
H3A	0.3080	0.9848	0.5732	0.070*
C4	0.2177 (3)	0.8115 (3)	0.4318 (3)	0.0555 (7)
H4A	0.1215	0.8199	0.3936	0.067*
C5	0.2451 (3)	0.6974 (3)	0.3778 (2)	0.0455 (6)
C6	0.1282 (3)	0.5869 (3)	0.2659 (2)	0.0478 (6)
H6A	0.1532	0.5114	0.2388	0.057*
C7	−0.0113 (3)	0.5867 (3)	0.2003 (2)	0.0492 (6)
H7A	−0.0320	0.6648	0.2281	0.059*
C8	−0.1367 (3)	0.4785 (3)	0.0895 (2)	0.0435 (6)
C9	−0.1236 (3)	0.3541 (3)	0.0378 (2)	0.0443 (6)
H9A	−0.0318	0.3384	0.0750	0.053*
C10	−0.2452 (3)	0.2549 (3)	−0.0674 (2)	0.0446 (6)
C11	−0.3846 (3)	0.2778 (3)	−0.1224 (2)	0.0446 (6)
C12	−0.3978 (3)	0.3996 (3)	−0.0715 (2)	0.0484 (6)
H12A	−0.4902	0.4148	−0.1079	0.058*
C13	−0.2746 (3)	0.4999 (3)	0.0333 (2)	0.0513 (6)
H13A	−0.2843	0.5825	0.0665	0.062*
C14	0.4288 (3)	0.5777 (3)	0.3817 (3)	0.0575 (7)
H14A	0.5370	0.5939	0.4304	0.086*
H14B	0.4148	0.5782	0.3017	0.086*
H14C	0.3607	0.4871	0.3780	0.086*
C15	−0.1033 (4)	0.1044 (4)	−0.0758 (3)	0.0733 (10)
H15A	−0.1162	0.0160	−0.1260	0.110*
H15B	−0.0847	0.0984	0.0038	0.110*
H15C	−0.0147	0.1802	−0.0712	0.110*
C16	0.8901 (3)	0.2169 (3)	0.3001 (2)	0.0474 (6)
C17	0.8818 (4)	0.3438 (3)	0.3475 (3)	0.0577 (7)
H17A	0.9713	0.4164	0.4103	0.069*
C18	0.7421 (4)	0.3636 (3)	0.3025 (3)	0.0649 (8)
H18A	0.7365	0.4492	0.3339	0.078*
C19	0.6110 (3)	0.2548 (3)	0.2102 (3)	0.0568 (7)
C20	0.6163 (3)	0.1274 (3)	0.1621 (3)	0.0547 (7)
H20A	0.5259	0.0546	0.1002	0.066*
C21	0.7575 (3)	0.1089 (3)	0.2070 (2)	0.0519 (6)
H21A	0.7633	0.0238	0.1744	0.062*
O1W	0.2172 (3)	0.1988 (3)	0.6854 (3)	0.0753 (7)
H2W1	0.196 (5)	0.217 (5)	0.622 (4)	0.093 (16)*
H1W1	0.148 (5)	0.124 (4)	0.671 (3)	0.079 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.0699 (3)	0.1027 (3)	0.1419 (4)	0.0567 (2)	0.0504 (3)	0.0641 (3)
S1	0.0390 (4)	0.0670 (5)	0.0786 (6)	0.0186 (3)	0.0175 (4)	0.0237 (4)
O1	0.0524 (11)	0.0487 (11)	0.0694 (13)	0.0257 (9)	0.0008 (10)	−0.0031 (10)
O2	0.0436 (10)	0.0497 (11)	0.0594 (12)	0.0154 (9)	−0.0018 (9)	−0.0002 (9)
O3	0.0558 (14)	0.0819 (17)	0.171 (3)	0.0330 (13)	0.0319 (16)	0.0612 (19)
O4	0.0677 (16)	0.118 (2)	0.0798 (18)	0.0354 (16)	−0.0017 (14)	0.0105 (16)
O5	0.0644 (15)	0.112 (2)	0.122 (2)	0.0398 (15)	0.0553 (16)	0.0469 (18)
N1	0.0371 (11)	0.0485 (12)	0.0416 (12)	0.0127 (9)	0.0123 (9)	0.0139 (10)
C1	0.0380 (14)	0.0643 (18)	0.0439 (15)	0.0100 (13)	0.0079 (12)	0.0178 (13)
C2	0.0526 (16)	0.0527 (16)	0.0403 (15)	0.0047 (13)	0.0113 (13)	0.0048 (12)
C3	0.0587 (18)	0.0557 (17)	0.0496 (16)	0.0162 (14)	0.0207 (14)	0.0056 (13)
C4	0.0462 (15)	0.0586 (17)	0.0508 (16)	0.0210 (13)	0.0139 (13)	0.0065 (13)
C5	0.0386 (13)	0.0493 (15)	0.0412 (14)	0.0135 (11)	0.0133 (11)	0.0125 (11)
C6	0.0393 (13)	0.0471 (14)	0.0441 (14)	0.0154 (11)	0.0103 (11)	0.0042 (11)
C7	0.0467 (14)	0.0477 (15)	0.0440 (14)	0.0187 (12)	0.0133 (12)	0.0062 (12)
C8	0.0391 (13)	0.0471 (14)	0.0377 (13)	0.0163 (11)	0.0118 (11)	0.0092 (11)
C9	0.0344 (12)	0.0466 (14)	0.0454 (14)	0.0168 (11)	0.0097 (11)	0.0137 (11)
C10	0.0416 (13)	0.0389 (13)	0.0461 (14)	0.0150 (11)	0.0130 (11)	0.0107 (11)
C11	0.0362 (12)	0.0407 (13)	0.0424 (14)	0.0091 (10)	0.0075 (11)	0.0104 (11)
C12	0.0361 (13)	0.0537 (15)	0.0470 (15)	0.0202 (12)	0.0092 (11)	0.0110 (12)
C13	0.0462 (15)	0.0524 (15)	0.0478 (15)	0.0246 (12)	0.0124 (12)	0.0063 (12)
C14	0.0448 (15)	0.0613 (17)	0.0609 (18)	0.0240 (13)	0.0149 (13)	0.0182 (14)
C15	0.0608 (19)	0.0602 (19)	0.084 (2)	0.0365 (16)	0.0133 (17)	0.0043 (17)
C16	0.0414 (13)	0.0529 (15)	0.0481 (15)	0.0163 (12)	0.0204 (12)	0.0178 (12)
C17	0.0547 (17)	0.0511 (16)	0.0597 (18)	0.0130 (13)	0.0259 (15)	0.0107 (14)
C18	0.070 (2)	0.0483 (16)	0.089 (2)	0.0268 (15)	0.0453 (19)	0.0212 (16)
C19	0.0525 (16)	0.0658 (19)	0.0734 (19)	0.0317 (15)	0.0359 (15)	0.0370 (16)
C20	0.0464 (15)	0.0619 (17)	0.0501 (16)	0.0190 (13)	0.0174 (13)	0.0159 (13)
C21	0.0498 (15)	0.0536 (16)	0.0513 (16)	0.0227 (13)	0.0217 (13)	0.0098 (13)
O1W	0.0510 (14)	0.0705 (17)	0.0782 (19)	0.0190 (13)	0.0064 (12)	0.0174 (14)

Br1—C19	1.892 (3)	C8—C9	1.398 (4)
S1—O3	1.433 (3)	C9—C10	1.375 (4)
S1—O5	1.438 (3)	C9—H9A	0.9300
S1—O4	1.438 (3)	C10—C11	1.404 (4)
S1—C16	1.773 (3)	C11—C12	1.373 (4)
O1—C10	1.363 (3)	C12—C13	1.382 (4)
O1—C15	1.425 (3)	C12—H12A	0.9300
O2—C11	1.356 (3)	C13—H13A	0.9300
O2—H1O2	0.8200	C14—H14A	0.9600
N1—C1	1.360 (3)	C14—H14B	0.9600
N1—C5	1.361 (3)	C14—H14C	0.9600
N1—C14	1.473 (4)	C15—H15A	0.9600
C1—C2	1.355 (4)	C15—H15B	0.9600
C1—H1A	0.9300	C15—H15C	0.9600
C2—C3	1.376 (4)	C16—C21	1.380 (4)
C2—H2A	0.9300	C16—C17	1.381 (4)
C3—C4	1.357 (4)	C17—C18	1.373 (4)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.400 (4)	C18—C19	1.374 (5)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.449 (4)	C19—C20	1.374 (4)
C6—C7	1.318 (4)	C20—C21	1.380 (4)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.454 (4)	C21—H21A	0.9300
C7—H7A	0.9300	O1W—H2W1	0.81 (4)
C8—C13	1.385 (4)	O1W—H1W1	0.80 (4)
O3—S1—O5	112.54 (19)	O2—C11—C12	122.9 (2)
O3—S1—O4	112.9 (2)	O2—C11—C10	117.3 (2)
O5—S1—O4	112.02 (19)	C12—C11—C10	119.8 (2)
O3—S1—C16	106.57 (14)	C11—C12—C13	120.4 (2)
O5—S1—C16	105.90 (14)	C11—C12—H12A	119.8
O4—S1—C16	106.35 (15)	C13—C12—H12A	119.8
C10—O1—C15	117.7 (2)	C12—C13—C8	120.6 (2)
C11—O2—H1O2	109.5	C12—C13—H13A	119.7
C1—N1—C5	121.0 (2)	C8—C13—H13A	119.7
C1—N1—C14	118.6 (2)	N1—C14—H14A	109.5
C5—N1—C14	120.4 (2)	N1—C14—H14B	109.5
C2—C1—N1	121.7 (3)	H14A—C14—H14B	109.5
C2—C1—H1A	119.1	N1—C14—H14C	109.5
N1—C1—H1A	119.1	H14A—C14—H14C	109.5
C1—C2—C3	118.6 (3)	H14B—C14—H14C	109.5
C1—C2—H2A	120.7	O1—C15—H15A	109.5
C3—C2—H2A	120.7	O1—C15—H15B	109.5
C4—C3—C2	120.1 (3)	H15A—C15—H15B	109.5
C4—C3—H3A	120.0	O1—C15—H15C	109.5
C2—C3—H3A	120.0	H15A—C15—H15C	109.5
C3—C4—C5	121.3 (3)	H15B—C15—H15C	109.5
C3—C4—H4A	119.4	C21—C16—C17	120.0 (3)
C5—C4—H4A	119.4	C21—C16—S1	120.0 (2)
N1—C5—C4	117.3 (2)	C17—C16—S1	120.0 (2)
N1—C5—C6	119.4 (2)	C18—C17—C16	120.4 (3)
C4—C5—C6	123.3 (2)	C18—C17—H17A	119.8
C7—C6—C5	124.1 (3)	C16—C17—H17A	119.8
C7—C6—H6A	118.0	C17—C18—C19	118.9 (3)
C5—C6—H6A	118.0	C17—C18—H18A	120.6
C6—C7—C8	127.6 (3)	C19—C18—H18A	120.6
C6—C7—H7A	116.2	C18—C19—C20	121.7 (3)
C8—C7—H7A	116.2	C18—C19—Br1	119.4 (2)
C13—C8—C9	118.9 (2)	C20—C19—Br1	118.8 (2)
C13—C8—C7	118.4 (2)	C19—C20—C21	119.1 (3)
C9—C8—C7	122.7 (2)	C19—C20—H20A	120.5
C10—C9—C8	120.7 (2)	C21—C20—H20A	120.5
C10—C9—H9A	119.7	C16—C21—C20	119.9 (3)
C8—C9—H9A	119.7	C16—C21—H21A	120.0
O1—C10—C9	125.3 (2)	C20—C21—H21A	120.0
O1—C10—C11	115.1 (2)	H2W1—O1W—H1W1	105 (4)
C9—C10—C11	119.6 (2)
C5—N1—C1—C2	−1.1 (4)	O1—C10—C11—C12	−178.8 (2)
C14—N1—C1—C2	178.2 (3)	C9—C10—C11—C12	0.8 (4)
N1—C1—C2—C3	−0.2 (4)	O2—C11—C12—C13	−177.9 (3)
C1—C2—C3—C4	0.6 (5)	C10—C11—C12—C13	0.1 (4)
C2—C3—C4—C5	0.2 (5)	C11—C12—C13—C8	−0.7 (4)
C1—N1—C5—C4	1.9 (4)	C9—C8—C13—C12	0.5 (4)
C14—N1—C5—C4	−177.4 (3)	C7—C8—C13—C12	−179.4 (3)
C1—N1—C5—C6	−177.4 (2)	O3—S1—C16—C21	−36.2 (3)
C14—N1—C5—C6	3.3 (4)	O5—S1—C16—C21	83.9 (3)
C3—C4—C5—N1	−1.5 (4)	O4—S1—C16—C21	−156.8 (2)
C3—C4—C5—C6	177.8 (3)	O3—S1—C16—C17	144.8 (3)
N1—C5—C6—C7	−176.7 (3)	O5—S1—C16—C17	−95.2 (3)
C4—C5—C6—C7	4.1 (4)	O4—S1—C16—C17	24.2 (3)
C5—C6—C7—C8	−178.0 (3)	C21—C16—C17—C18	0.0 (4)
C6—C7—C8—C13	−179.1 (3)	S1—C16—C17—C18	179.0 (2)
C6—C7—C8—C9	1.0 (5)	C16—C17—C18—C19	0.4 (5)
C13—C8—C9—C10	0.4 (4)	C17—C18—C19—C20	−0.1 (5)
C7—C8—C9—C10	−179.8 (2)	C17—C18—C19—Br1	177.5 (2)
C15—O1—C10—C9	−0.8 (4)	C18—C19—C20—C21	−0.6 (5)
C15—O1—C10—C11	178.8 (3)	Br1—C19—C20—C21	−178.2 (2)
C8—C9—C10—O1	178.6 (3)	C17—C16—C21—C20	−0.7 (4)
C8—C9—C10—C11	−1.0 (4)	S1—C16—C21—C20	−179.7 (2)
O1—C10—C11—O2	−0.8 (4)	C19—C20—C21—C16	1.0 (4)
C9—C10—C11—O2	178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1Wi	0.82	1.88	2.685 (4)	169
O1W—H2W1···O4ii	0.81 (5)	2.03 (5)	2.834 (4)	172 (5)
O1W—H1W1···O3iii	0.81 (4)	1.99 (5)	2.793 (5)	173 (5)
C1—H1A···O5iv	0.93	2.57	3.491 (4)	170
C2—H2A···O1v	0.93	2.51	3.440 (4)	176
C2—H2A···O2v	0.93	2.60	3.183 (4)	121
C3—H3A···O2v	0.93	2.54	3.160 (4)	124
C14—H14A···O4iv	0.96	2.54	3.448 (5)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1W i	0.82	1.88	2.685 (4)	169
O1W—H2W1⋯O4ii	0.81 (5)	2.03 (5)	2.834 (4)	172 (5)
O1W—H1W1⋯O3iii	0.81 (4)	1.99 (5)	2.793 (5)	173 (5)
C1—H1A⋯O5iv	0.93	2.57	3.491 (4)	170
C2—H2A⋯O1v	0.93	2.51	3.440 (4)	176
C2—H2A⋯O2v	0.93	2.60	3.183 (4)	121
C3—H3A⋯O2v	0.93	2.54	3.160 (4)	124
C14—H14A⋯O4iv	0.96	2.54	3.448 (5)	158

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