2-[(E)-4-(Dimethyl-amino)-styr-yl]-1-methyl-pyridinium 4-chloro-benzene-sulfonate monohydrate.

In the title hydrated mol-ecular salt, C(16)H(19)N(2) (+)·C(6)H(4)ClO(3)S(-)·H(2)O, the 2-[4-(dimethyl-amino)-styr-yl]-1-methyl-pyridinium cation exists in an E configuration with respect to the C=C bond and is slightly twisted, with the dihedral angle between the pyridinium and benzene rings being 9.33 (10)°. In the crystal structure, the packing is stabilized by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, which link the cations, anions and water mol-ecules into chains propagating in [010]. These chains are stacked along the a axis by π-π inter-actions, with centroid-to-centroid distances of 3.6429 (12) and 3.6879 (12) Å; weak C-H⋯π inter-actions are also observed.

Related literature

For representative bond lengths, see Allen et al. (1987 ▶). For background to and application of quarternary ammonium compounds, see: Armitage et al. (1929 ▶); Browning et al. (1922 ▶); Chanawanno et al. (2010 ▶); Wainwright & Kristiansen (2003 ▶); Wainwright (2008 ▶). For a related structure, see: Chantra­promma et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H19N2 +·C6H4ClO3S−·H2O

M = 448.96

Triclinic,

a = 6.3895 (1) Å

b = 9.8739 (2) Å

c = 17.0074 (3) Å

α = 95.721 (1)°

β = 90.500 (1)°

γ = 91.260 (1)°

V = 1067.32 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.31 × 0.10 × 0.05 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.912, T max = 0.984

23113 measured reflections

6156 independent reflections

4327 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.135

S = 1.03

6156 reflections

282 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.43 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043230/hb5695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043230/hb5695Isup2.hkl

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

C16H19N2+·C6H4ClO3S−·H2O	Z = 2
Mr = 448.96	F(000) = 472
Triclinic, P1	Dx = 1.397 Mg m−3
Hall symbol: -P 1	Melting point = 516–517 K
a = 6.3895 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8739 (2) Å	Cell parameters from 6156 reflections
c = 17.0074 (3) Å	θ = 1.2–30.0°
α = 95.721 (1)°	µ = 0.31 mm−1
β = 90.500 (1)°	T = 100 K
γ = 91.260 (1)°	Block, orange
V = 1067.32 (3) Å3	0.31 × 0.10 × 0.05 mm

Bruker APEX DUO CCD diffractometer	6156 independent reflections
Radiation source: sealed tube	4327 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 30.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.912, Tmax = 0.984	k = −12→13
23113 measured reflections	l = −23→23

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.637P] where P = (Fo2 + 2Fc2)/3
6156 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.43 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
N1	0.0246 (3)	0.11936 (19)	0.10897 (11)	0.0156 (4)
N2	1.2149 (3)	0.17645 (19)	0.39494 (11)	0.0193 (4)
C1	−0.1576 (3)	0.0753 (2)	0.07232 (13)	0.0173 (4)
H1A	−0.2417	0.1374	0.0500	0.021*
C2	−0.2199 (3)	−0.0591 (2)	0.06768 (13)	0.0188 (5)
H2A	−0.3458	−0.0881	0.0431	0.023*
C3	−0.0922 (3)	−0.1511 (2)	0.10026 (13)	0.0189 (5)
H3A	−0.1307	−0.2429	0.0969	0.023*
C4	0.0920 (3)	−0.1056 (2)	0.13766 (13)	0.0174 (4)
H4A	0.1774	−0.1676	0.1594	0.021*
C5	0.1533 (3)	0.0327 (2)	0.14361 (12)	0.0157 (4)
C6	0.3439 (3)	0.0866 (2)	0.18323 (13)	0.0167 (4)
H6A	0.3830	0.1767	0.1785	0.020*
C7	0.4671 (3)	0.0127 (2)	0.22659 (13)	0.0167 (4)
H7A	0.4256	−0.0776	0.2294	0.020*
C8	0.6572 (3)	0.0584 (2)	0.26937 (13)	0.0162 (4)
C9	0.7629 (3)	−0.0320 (2)	0.31341 (13)	0.0173 (4)
H9A	0.7088	−0.1201	0.3143	0.021*
C10	0.9449 (3)	0.0052 (2)	0.35563 (13)	0.0181 (4)
H10A	1.0101	−0.0573	0.3845	0.022*
C11	1.0323 (3)	0.1382 (2)	0.35494 (13)	0.0161 (4)
C12	0.9253 (3)	0.2302 (2)	0.31130 (13)	0.0168 (4)
H12A	0.9784	0.3185	0.3103	0.020*
C13	0.7425 (3)	0.1910 (2)	0.26998 (13)	0.0162 (4)
H13A	0.6747	0.2537	0.2420	0.019*
C14	0.0814 (4)	0.2658 (2)	0.10930 (14)	0.0198 (5)
H14A	0.1017	0.3053	0.1628	0.030*
H14B	−0.0291	0.3115	0.0849	0.030*
H14C	0.2084	0.2754	0.0804	0.030*
C15	1.3197 (4)	0.0833 (3)	0.44178 (15)	0.0237 (5)
H15A	1.2260	0.0554	0.4813	0.036*
H15B	1.4412	0.1278	0.4670	0.036*
H15C	1.3614	0.0048	0.4082	0.036*
C16	1.3169 (3)	0.3058 (2)	0.38333 (14)	0.0204 (5)
H16A	1.3290	0.3140	0.3278	0.031*
H16B	1.4538	0.3098	0.4072	0.031*
H16C	1.2352	0.3789	0.4073	0.031*
Cl1	1.18810 (10)	0.69360 (7)	0.46691 (4)	0.02879 (16)
S1	0.57475 (8)	0.54114 (6)	0.17948 (3)	0.01647 (13)
O1	0.4692 (2)	0.66863 (16)	0.17231 (10)	0.0204 (3)
O2	0.4357 (3)	0.43430 (17)	0.20239 (10)	0.0249 (4)
O3	0.7023 (3)	0.50131 (18)	0.11086 (10)	0.0247 (4)
C17	0.7541 (3)	0.5767 (2)	0.26013 (13)	0.0164 (4)
C18	0.6803 (3)	0.5782 (2)	0.33656 (13)	0.0192 (5)
H18A	0.5409	0.5554	0.3451	0.023*
C19	0.8147 (4)	0.6137 (2)	0.40055 (14)	0.0209 (5)
H19A	0.7663	0.6153	0.4520	0.025*
C20	1.0214 (3)	0.6468 (2)	0.38611 (13)	0.0190 (5)
C21	1.0976 (3)	0.6445 (2)	0.31068 (14)	0.0204 (5)
H21A	1.2371	0.6672	0.3024	0.024*
C22	0.9634 (3)	0.6076 (2)	0.24660 (14)	0.0184 (4)
H22A	1.0134	0.6037	0.1953	0.022*
O1W	0.5623 (3)	0.29024 (19)	0.99640 (12)	0.0270 (4)
H1W1	0.595 (5)	0.366 (4)	1.026 (2)	0.054 (10)*
H2W1	0.552 (6)	0.317 (4)	0.946 (3)	0.075 (13)*

	U11	U22	U33	U12	U13	U23
N1	0.0147 (8)	0.0158 (9)	0.0156 (9)	−0.0006 (7)	−0.0013 (7)	−0.0013 (7)
N2	0.0156 (9)	0.0188 (10)	0.0236 (10)	−0.0026 (7)	−0.0070 (7)	0.0046 (8)
C1	0.0133 (9)	0.0227 (11)	0.0157 (10)	0.0012 (8)	−0.0015 (8)	0.0004 (9)
C2	0.0155 (10)	0.0239 (12)	0.0164 (11)	−0.0026 (9)	−0.0017 (8)	−0.0008 (9)
C3	0.0196 (10)	0.0178 (11)	0.0188 (11)	−0.0048 (9)	−0.0009 (8)	0.0002 (9)
C4	0.0171 (10)	0.0168 (11)	0.0183 (11)	0.0001 (8)	−0.0018 (8)	0.0018 (8)
C5	0.0132 (9)	0.0197 (11)	0.0139 (10)	0.0018 (8)	−0.0010 (8)	−0.0002 (8)
C6	0.0150 (10)	0.0157 (10)	0.0189 (11)	−0.0024 (8)	−0.0010 (8)	0.0004 (8)
C7	0.0157 (10)	0.0138 (10)	0.0198 (11)	−0.0014 (8)	−0.0010 (8)	−0.0014 (8)
C8	0.0146 (10)	0.0174 (11)	0.0161 (10)	0.0016 (8)	−0.0005 (8)	−0.0006 (8)
C9	0.0181 (10)	0.0134 (10)	0.0200 (11)	−0.0015 (8)	−0.0005 (8)	0.0000 (8)
C10	0.0200 (10)	0.0162 (11)	0.0185 (11)	0.0022 (8)	−0.0028 (8)	0.0040 (8)
C11	0.0137 (9)	0.0202 (11)	0.0139 (10)	−0.0008 (8)	−0.0008 (8)	−0.0010 (8)
C12	0.0164 (10)	0.0167 (11)	0.0171 (10)	−0.0023 (8)	−0.0007 (8)	0.0012 (8)
C13	0.0162 (10)	0.0173 (11)	0.0153 (10)	0.0013 (8)	−0.0004 (8)	0.0025 (8)
C14	0.0194 (10)	0.0152 (11)	0.0249 (12)	−0.0007 (8)	−0.0031 (9)	0.0024 (9)
C15	0.0183 (11)	0.0275 (13)	0.0260 (12)	−0.0007 (9)	−0.0068 (9)	0.0073 (10)
C16	0.0182 (10)	0.0220 (11)	0.0205 (11)	−0.0047 (9)	−0.0029 (8)	0.0005 (9)
Cl1	0.0305 (3)	0.0304 (3)	0.0238 (3)	−0.0009 (3)	−0.0125 (2)	−0.0040 (2)
S1	0.0171 (3)	0.0136 (3)	0.0182 (3)	−0.00053 (19)	−0.0044 (2)	−0.0003 (2)
O1	0.0215 (8)	0.0158 (8)	0.0239 (9)	0.0022 (6)	−0.0041 (6)	0.0017 (6)
O2	0.0251 (8)	0.0192 (8)	0.0306 (10)	−0.0073 (7)	−0.0091 (7)	0.0056 (7)
O3	0.0225 (8)	0.0312 (10)	0.0187 (8)	0.0052 (7)	−0.0026 (6)	−0.0070 (7)
C17	0.0186 (10)	0.0104 (10)	0.0199 (11)	0.0008 (8)	−0.0036 (8)	0.0004 (8)
C18	0.0173 (10)	0.0202 (11)	0.0202 (11)	−0.0008 (9)	0.0001 (8)	0.0023 (9)
C19	0.0257 (11)	0.0207 (11)	0.0159 (11)	0.0005 (9)	0.0002 (9)	0.0001 (9)
C20	0.0212 (11)	0.0161 (11)	0.0191 (11)	0.0019 (9)	−0.0061 (9)	−0.0014 (9)
C21	0.0159 (10)	0.0183 (11)	0.0266 (12)	−0.0019 (9)	−0.0048 (9)	0.0013 (9)
C22	0.0207 (11)	0.0166 (11)	0.0180 (11)	0.0011 (9)	−0.0005 (8)	0.0013 (9)
O1W	0.0358 (10)	0.0209 (9)	0.0238 (10)	−0.0001 (8)	−0.0092 (8)	0.0010 (8)

N1—C1	1.358 (3)	C13—H13A	0.9300
N1—C5	1.371 (3)	C14—H14A	0.9600
N1—C14	1.482 (3)	C14—H14B	0.9600
N2—C11	1.372 (2)	C14—H14C	0.9600
N2—C15	1.447 (3)	C15—H15A	0.9600
N2—C16	1.452 (3)	C15—H15B	0.9600
C1—C2	1.372 (3)	C15—H15C	0.9600
C1—H1A	0.9300	C16—H16A	0.9600
C2—C3	1.387 (3)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.378 (3)	Cl1—C20	1.750 (2)
C3—H3A	0.9300	S1—O2	1.4495 (17)
C4—C5	1.406 (3)	S1—O3	1.4562 (18)
C4—H4A	0.9300	S1—O1	1.4561 (16)
C5—C6	1.451 (3)	S1—C17	1.782 (2)
C6—C7	1.349 (3)	C17—C18	1.386 (3)
C6—H6A	0.9300	C17—C22	1.391 (3)
C7—C8	1.451 (3)	C18—C19	1.392 (3)
C7—H7A	0.9300	C18—H18A	0.9300
C8—C9	1.402 (3)	C19—C20	1.383 (3)
C8—C13	1.406 (3)	C19—H19A	0.9300
C9—C10	1.385 (3)	C20—C21	1.374 (3)
C9—H9A	0.9300	C21—C22	1.395 (3)
C10—C11	1.417 (3)	C21—H21A	0.9300
C10—H10A	0.9300	C22—H22A	0.9300
C11—C12	1.413 (3)	O1W—H1W1	0.88 (4)
C12—C13	1.386 (3)	O1W—H2W1	0.91 (4)
C12—H12A	0.9300
C1—N1—C5	121.90 (19)	C8—C13—H13A	119.2
C1—N1—C14	117.25 (18)	N1—C14—H14A	109.5
C5—N1—C14	120.85 (17)	N1—C14—H14B	109.5
C11—N2—C15	120.73 (19)	H14A—C14—H14B	109.5
C11—N2—C16	119.76 (18)	N1—C14—H14C	109.5
C15—N2—C16	119.16 (17)	H14A—C14—H14C	109.5
N1—C1—C2	121.1 (2)	H14B—C14—H14C	109.5
N1—C1—H1A	119.4	N2—C15—H15A	109.5
C2—C1—H1A	119.4	N2—C15—H15B	109.5
C1—C2—C3	118.99 (19)	H15A—C15—H15B	109.5
C1—C2—H2A	120.5	N2—C15—H15C	109.5
C3—C2—H2A	120.5	H15A—C15—H15C	109.5
C4—C3—C2	119.6 (2)	H15B—C15—H15C	109.5
C4—C3—H3A	120.2	N2—C16—H16A	109.5
C2—C3—H3A	120.2	N2—C16—H16B	109.5
C3—C4—C5	121.2 (2)	H16A—C16—H16B	109.5
C3—C4—H4A	119.4	N2—C16—H16C	109.5
C5—C4—H4A	119.4	H16A—C16—H16C	109.5
N1—C5—C4	117.15 (18)	H16B—C16—H16C	109.5
N1—C5—C6	119.21 (19)	O2—S1—O3	114.41 (11)
C4—C5—C6	123.64 (19)	O2—S1—O1	113.10 (10)
C7—C6—C5	123.3 (2)	O3—S1—O1	112.03 (10)
C7—C6—H6A	118.3	O2—S1—C17	105.34 (10)
C5—C6—H6A	118.3	O3—S1—C17	105.74 (10)
C6—C7—C8	127.2 (2)	O1—S1—C17	105.26 (10)
C6—C7—H7A	116.4	C18—C17—C22	120.5 (2)
C8—C7—H7A	116.4	C18—C17—S1	118.96 (16)
C9—C8—C13	117.25 (18)	C22—C17—S1	120.51 (18)
C9—C8—C7	119.4 (2)	C17—C18—C19	120.0 (2)
C13—C8—C7	123.38 (19)	C17—C18—H18A	120.0
C10—C9—C8	122.3 (2)	C19—C18—H18A	120.0
C10—C9—H9A	118.9	C20—C19—C18	118.8 (2)
C8—C9—H9A	118.9	C20—C19—H19A	120.6
C9—C10—C11	120.26 (19)	C18—C19—H19A	120.6
C9—C10—H10A	119.9	C21—C20—C19	121.9 (2)
C11—C10—H10A	119.9	C21—C20—Cl1	119.68 (17)
N2—C11—C12	121.0 (2)	C19—C20—Cl1	118.42 (18)
N2—C11—C10	121.27 (19)	C20—C21—C22	119.3 (2)
C12—C11—C10	117.72 (18)	C20—C21—H21A	120.4
C13—C12—C11	121.0 (2)	C22—C21—H21A	120.4
C13—C12—H12A	119.5	C17—C22—C21	119.5 (2)
C11—C12—H12A	119.5	C17—C22—H22A	120.3
C12—C13—C8	121.5 (2)	C21—C22—H22A	120.3
C12—C13—H13A	119.2	H1W1—O1W—H2W1	104 (3)
C5—N1—C1—C2	−0.7 (3)	C9—C10—C11—N2	−178.6 (2)
C14—N1—C1—C2	178.5 (2)	C9—C10—C11—C12	1.1 (3)
N1—C1—C2—C3	−0.8 (3)	N2—C11—C12—C13	179.1 (2)
C1—C2—C3—C4	1.1 (3)	C10—C11—C12—C13	−0.7 (3)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C8	−0.4 (3)
C1—N1—C5—C4	1.9 (3)	C9—C8—C13—C12	1.0 (3)
C14—N1—C5—C4	−177.3 (2)	C7—C8—C13—C12	−179.6 (2)
C1—N1—C5—C6	−178.8 (2)	O2—S1—C17—C18	−39.6 (2)
C14—N1—C5—C6	2.0 (3)	O3—S1—C17—C18	−161.15 (18)
C3—C4—C5—N1	−1.6 (3)	O1—S1—C17—C18	80.12 (19)
C3—C4—C5—C6	179.1 (2)	O2—S1—C17—C22	142.77 (18)
N1—C5—C6—C7	172.1 (2)	O3—S1—C17—C22	21.3 (2)
C4—C5—C6—C7	−8.6 (4)	O1—S1—C17—C22	−97.47 (19)
C5—C6—C7—C8	−178.7 (2)	C22—C17—C18—C19	1.5 (3)
C6—C7—C8—C9	178.2 (2)	S1—C17—C18—C19	−176.11 (18)
C6—C7—C8—C13	−1.1 (4)	C17—C18—C19—C20	−0.2 (3)
C13—C8—C9—C10	−0.5 (3)	C18—C19—C20—C21	−0.5 (4)
C7—C8—C9—C10	−179.9 (2)	C18—C19—C20—Cl1	179.14 (18)
C8—C9—C10—C11	−0.5 (3)	C19—C20—C21—C22	−0.1 (3)
C15—N2—C11—C12	177.8 (2)	Cl1—C20—C21—C22	−179.73 (17)
C16—N2—C11—C12	−9.1 (3)	C18—C17—C22—C21	−2.1 (3)
C15—N2—C11—C10	−2.5 (3)	S1—C17—C22—C21	175.48 (17)
C16—N2—C11—C10	170.6 (2)	C20—C21—C22—C17	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3i	0.88 (4)	1.97 (4)	2.831 (3)	164 (3)
O1W—H2W1···O1ii	0.92 (5)	2.04 (5)	2.944 (3)	167 (4)
C1—H1A···O1Wiii	0.93	2.24	3.170 (3)	179
C2—H2A···O1Wiv	0.93	2.44	3.229 (3)	143
C4—H4A···O1v	0.93	2.52	3.406 (2)	160
C6—H6A···O2	0.93	2.55	3.453 (3)	164
C13—H13A···O2	0.93	2.51	3.414 (3)	164
C14—H14A···O2	0.96	2.51	3.106 (3)	120
C14—H14B···O3vi	0.96	2.58	3.393 (3)	143
C9—H9A···Cg3v	0.93	2.93	3.650 (2)	135
C12—H12A···Cg3	0.93	2.95	3.760 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3i	0.88 (4)	1.97 (4)	2.831 (3)	164 (3)
O1W—H2W1⋯O1ii	0.92 (5)	2.04 (5)	2.944 (3)	167 (4)
C1—H1A⋯O1Wiii	0.93	2.24	3.170 (3)	179
C2—H2A⋯O1Wiv	0.93	2.44	3.229 (3)	143
C4—H4A⋯O1v	0.93	2.52	3.406 (2)	160
C6—H6A⋯O2	0.93	2.55	3.453 (3)	164
C13—H13A⋯O2	0.93	2.51	3.414 (3)	164
C14—H14A⋯O2	0.96	2.51	3.106 (3)	120
C14—H14B⋯O3vi	0.96	2.58	3.393 (3)	143
C9—H9A⋯Cg3v	0.93	2.93	3.650 (2)	135
C12—H12A⋯Cg3	0.93	2.95	3.760 (2)	147

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