4-{2-[4-(Dimethyl-amino)-phen-yl]ethen-yl}-1-methyl-pyridinium 2,4,6-trimethyl-benzene-sulfonate monohydrate.

In the crystal structure of the title organic salt, C(16)H(19)N(2) (+)·C(9)H(11)O(3)S(-)·H(2)O, the cations pack head-to-tail within a sheet and are aligned in opposite directions in neighboring sheets. The benzene ring of the anion makes an angle of 76.99 (6)° with the plane of the cationic chromophore. The cations are situated in the ab plane, whereas the benzene rings of the anions lie in the ac plane.

Related literature

For the crystal structure of solvent-free 2,4,6- trimethyl­benzene­sulfonate (DSTMS), see: Yang et al. (2007 ▶); Mutter et al. (2007 ▶). For the crystal structure of 4-N,N-dimethyl­amino-4′-N′-methyl­stilbazolium tosyl­ate (DAST) and DAST·H2O, see: Marder et al. (1989 ▶); Pan et al. (1996 ▶); Bryant et al. (1993 ▶). For the synthesis, see: Marder et al. (1994 ▶).

Experimental

Crystal data

C16H19N2 +·C9H11O3S−·H2O

M = 456.59

Triclinic,

a = 8.1993 (17) Å

b = 9.669 (2) Å

c = 15.247 (3) Å

α = 87.806 (7)°

β = 75.805 (6)°

γ = 83.239 (5)°

V = 1163.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 103 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.918, T max = 0.966

11232 measured reflections

5240 independent reflections

4259 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.00

5240 reflections

303 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007690/im2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007690/im2263Isup2.hkl

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

C16H19N2+·C9H11O3S−·H2O	Z = 2
Mr = 456.59	F(000) = 488
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1993 (17) Å	Cell parameters from 3579 reflections
b = 9.669 (2) Å	θ = 3.2–27.5°
c = 15.247 (3) Å	µ = 0.17 mm−1
α = 87.806 (7)°	T = 103 K
β = 75.805 (6)°	Chunk, red
γ = 83.239 (5)°	0.50 × 0.40 × 0.20 mm
V = 1163.7 (4) Å3

Rigaku AFC10/Saturn724+ diffractometer	5240 independent reflections
Radiation source: Rotating Anode	4259 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→12
Tmin = 0.918, Tmax = 0.966	l = −19→19
11232 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.560P] where P = (Fo2 + 2Fc2)/3
5240 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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
S1	0.36608 (5)	0.78675 (4)	0.16984 (2)	0.01575 (11)
O1	0.51685 (14)	0.75321 (13)	0.20319 (8)	0.0232 (3)
O2	0.36736 (15)	0.92045 (12)	0.12167 (8)	0.0231 (3)
O3	0.33464 (15)	0.67560 (12)	0.11702 (8)	0.0235 (3)
N1	1.13709 (16)	0.36393 (14)	0.06835 (9)	0.0163 (3)
N2	−0.18615 (17)	0.31865 (14)	0.36790 (9)	0.0199 (3)
C1	1.0477 (2)	0.25780 (17)	0.06110 (11)	0.0194 (3)
H1	1.1037	0.1764	0.0292	0.023*
C2	0.8769 (2)	0.26638 (18)	0.09932 (11)	0.0215 (3)
H2	0.8158	0.1908	0.0940	0.026*
C3	0.7916 (2)	0.38704 (18)	0.14644 (11)	0.0204 (3)
C4	0.8883 (2)	0.49457 (18)	0.15010 (11)	0.0221 (3)
H4	0.8351	0.5788	0.1794	0.027*
C5	1.0588 (2)	0.48092 (17)	0.11214 (11)	0.0197 (3)
H5	1.1228	0.5549	0.1167	0.024*
C6	1.3204 (2)	0.35286 (19)	0.02549 (11)	0.0226 (4)
H6A	1.3378	0.3588	−0.0404	0.027*
H6B	1.3750	0.2634	0.0421	0.027*
H6C	1.3701	0.4290	0.0463	0.027*
C7	0.6116 (2)	0.40354 (18)	0.19219 (11)	0.0222 (3)
H7	0.5612	0.4933	0.2138	0.027*
C8	0.5143 (2)	0.29984 (17)	0.20536 (11)	0.0209 (3)
H8	0.5658	0.2119	0.1810	0.025*
C9	0.3364 (2)	0.30837 (18)	0.25350 (11)	0.0204 (3)
C10	0.2517 (2)	0.19128 (18)	0.25496 (11)	0.0213 (3)
H10	0.3134	0.1078	0.2282	0.026*
C11	0.0816 (2)	0.19291 (17)	0.29396 (10)	0.0189 (3)
H11	0.0281	0.1110	0.2939	0.023*
C12	−0.01440 (19)	0.31519 (16)	0.33420 (10)	0.0163 (3)
C13	0.0716 (2)	0.43197 (16)	0.33729 (11)	0.0202 (3)
H13	0.0117	0.5140	0.3670	0.024*
C14	0.2427 (2)	0.42795 (17)	0.29738 (11)	0.0213 (3)
H14	0.2983	0.5081	0.2997	0.026*
C15	−0.2692 (2)	0.19605 (18)	0.36304 (11)	0.0221 (3)
H15A	−0.2441	0.1659	0.3000	0.027*
H15B	−0.3918	0.2181	0.3858	0.027*
H15C	−0.2279	0.1212	0.4000	0.027*
C16	−0.2850 (2)	0.44394 (19)	0.40913 (13)	0.0295 (4)
H16A	−0.2528	0.4623	0.4650	0.035*
H16B	−0.4056	0.4316	0.4231	0.035*
H16C	−0.2634	0.5227	0.3671	0.035*
C17	0.02360 (19)	0.82889 (15)	0.24753 (10)	0.0154 (3)
C18	−0.1177 (2)	0.83123 (16)	0.32025 (11)	0.0174 (3)
H18	−0.2270	0.8412	0.3084	0.021*
C19	−0.1047 (2)	0.81959 (16)	0.40931 (11)	0.0183 (3)
C20	0.0562 (2)	0.80729 (17)	0.42491 (11)	0.0199 (3)
H20	0.0670	0.8027	0.4856	0.024*
C21	0.2030 (2)	0.80140 (16)	0.35469 (10)	0.0178 (3)
C22	0.18631 (19)	0.80801 (15)	0.26519 (10)	0.0143 (3)
C23	−0.0066 (2)	0.85704 (17)	0.15439 (11)	0.0211 (3)
H23A	−0.1263	0.8522	0.1567	0.025*
H23B	0.0635	0.7872	0.1122	0.025*
H23C	0.0233	0.9500	0.1338	0.025*
C24	−0.2586 (2)	0.8222 (2)	0.48747 (11)	0.0261 (4)
H24A	−0.3611	0.8382	0.4646	0.031*
H24B	−0.2578	0.8972	0.5287	0.031*
H24C	−0.2570	0.7327	0.5199	0.031*
C25	0.3698 (2)	0.7919 (2)	0.38181 (12)	0.0287 (4)
H25A	0.3481	0.8006	0.4476	0.034*
H25B	0.4343	0.8671	0.3521	0.034*
H25C	0.4350	0.7017	0.3632	0.034*
O4	0.69606 (17)	1.00845 (14)	0.04707 (10)	0.0259 (3)
H4A	0.611 (3)	0.977 (3)	0.0748 (18)	0.053 (8)*
H4B	0.675 (3)	1.039 (3)	−0.0023 (18)	0.050 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.01557 (19)	0.01519 (19)	0.01466 (18)	−0.00387 (14)	0.00108 (14)	−0.00183 (13)
O1	0.0144 (5)	0.0307 (7)	0.0228 (6)	−0.0005 (5)	−0.0015 (5)	−0.0032 (5)
O2	0.0271 (6)	0.0198 (6)	0.0196 (6)	−0.0058 (5)	0.0006 (5)	0.0033 (4)
O3	0.0215 (6)	0.0238 (6)	0.0230 (6)	−0.0079 (5)	0.0028 (5)	−0.0095 (5)
N1	0.0142 (6)	0.0215 (7)	0.0136 (6)	−0.0040 (5)	−0.0028 (5)	0.0006 (5)
N2	0.0143 (6)	0.0190 (7)	0.0240 (7)	−0.0016 (5)	0.0001 (5)	−0.0006 (5)
C1	0.0218 (8)	0.0198 (8)	0.0186 (8)	−0.0046 (6)	−0.0077 (6)	0.0004 (6)
C2	0.0218 (8)	0.0247 (8)	0.0217 (8)	−0.0100 (7)	−0.0098 (7)	0.0048 (6)
C3	0.0183 (8)	0.0276 (9)	0.0160 (7)	−0.0042 (7)	−0.0058 (6)	0.0073 (6)
C4	0.0212 (8)	0.0242 (8)	0.0198 (8)	−0.0014 (7)	−0.0031 (6)	0.0000 (6)
C5	0.0205 (8)	0.0207 (8)	0.0179 (8)	−0.0056 (6)	−0.0033 (6)	−0.0005 (6)
C6	0.0136 (7)	0.0326 (9)	0.0202 (8)	−0.0046 (7)	−0.0002 (6)	−0.0015 (7)
C7	0.0229 (8)	0.0219 (8)	0.0219 (8)	−0.0007 (7)	−0.0064 (7)	0.0010 (6)
C8	0.0200 (8)	0.0229 (8)	0.0202 (8)	−0.0011 (6)	−0.0061 (6)	0.0006 (6)
C9	0.0163 (8)	0.0277 (9)	0.0164 (7)	0.0005 (6)	−0.0041 (6)	0.0034 (6)
C10	0.0198 (8)	0.0236 (8)	0.0190 (8)	0.0026 (6)	−0.0042 (6)	−0.0025 (6)
C11	0.0203 (8)	0.0175 (8)	0.0186 (8)	−0.0010 (6)	−0.0045 (6)	−0.0016 (6)
C12	0.0159 (7)	0.0176 (7)	0.0146 (7)	−0.0010 (6)	−0.0029 (6)	0.0021 (6)
C13	0.0190 (8)	0.0157 (7)	0.0248 (8)	0.0005 (6)	−0.0046 (6)	0.0002 (6)
C14	0.0213 (8)	0.0187 (8)	0.0255 (8)	−0.0057 (6)	−0.0078 (7)	0.0048 (6)
C15	0.0199 (8)	0.0244 (8)	0.0222 (8)	−0.0057 (7)	−0.0046 (6)	0.0039 (6)
C16	0.0182 (8)	0.0279 (9)	0.0363 (10)	0.0028 (7)	0.0034 (7)	−0.0055 (8)
C17	0.0176 (7)	0.0116 (7)	0.0167 (7)	−0.0005 (6)	−0.0043 (6)	0.0004 (5)
C18	0.0151 (7)	0.0165 (7)	0.0204 (8)	−0.0010 (6)	−0.0042 (6)	−0.0005 (6)
C19	0.0170 (8)	0.0173 (8)	0.0181 (7)	−0.0018 (6)	0.0001 (6)	0.0007 (6)
C20	0.0197 (8)	0.0262 (8)	0.0132 (7)	−0.0023 (7)	−0.0027 (6)	0.0006 (6)
C21	0.0159 (7)	0.0196 (8)	0.0179 (7)	−0.0021 (6)	−0.0040 (6)	−0.0004 (6)
C22	0.0146 (7)	0.0115 (7)	0.0151 (7)	−0.0020 (5)	0.0005 (6)	−0.0014 (5)
C23	0.0228 (8)	0.0232 (8)	0.0180 (8)	−0.0004 (7)	−0.0074 (6)	0.0015 (6)
C24	0.0193 (8)	0.0344 (10)	0.0201 (8)	−0.0005 (7)	0.0025 (7)	0.0008 (7)
C25	0.0191 (8)	0.0506 (12)	0.0169 (8)	−0.0021 (8)	−0.0058 (7)	−0.0031 (8)
O4	0.0243 (7)	0.0278 (7)	0.0286 (7)	−0.0110 (5)	−0.0098 (6)	0.0085 (5)

S1—O1	1.4468 (12)	C12—C13	1.408 (2)
S1—O3	1.4503 (11)	C13—C14	1.382 (2)
S1—O2	1.4619 (12)	C13—H13	0.9500
S1—C22	1.7969 (15)	C14—H14	0.9500
N1—C5	1.347 (2)	C15—H15A	0.9800
N1—C1	1.352 (2)	C15—H15B	0.9800
N1—C6	1.478 (2)	C15—H15C	0.9800
N2—C12	1.372 (2)	C16—H16A	0.9800
N2—C15	1.448 (2)	C16—H16B	0.9800
N2—C16	1.448 (2)	C16—H16C	0.9800
C1—C2	1.372 (2)	C17—C18	1.392 (2)
C1—H1	0.9500	C17—C22	1.415 (2)
C2—C3	1.411 (2)	C17—C23	1.510 (2)
C2—H2	0.9500	C18—C19	1.387 (2)
C3—C4	1.390 (2)	C18—H18	0.9500
C3—C7	1.463 (2)	C19—C20	1.388 (2)
C4—C5	1.369 (2)	C19—C24	1.507 (2)
C4—H4	0.9500	C20—C21	1.398 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—H6A	0.9800	C21—C22	1.403 (2)
C6—H6B	0.9800	C21—C25	1.515 (2)
C6—H6C	0.9800	C23—H23A	0.9800
C7—C8	1.333 (2)	C23—H23B	0.9800
C7—H7	0.9500	C23—H23C	0.9800
C8—C9	1.457 (2)	C24—H24A	0.9800
C8—H8	0.9500	C24—H24B	0.9800
C9—C10	1.393 (2)	C24—H24C	0.9800
C9—C14	1.405 (2)	C25—H25A	0.9800
C10—C11	1.374 (2)	C25—H25B	0.9800
C10—H10	0.9500	C25—H25C	0.9800
C11—C12	1.412 (2)	O4—H4A	0.81 (3)
C11—H11	0.9500	O4—H4B	0.85 (3)
O1—S1—O3	112.80 (7)	C12—C13—H13	119.8
O1—S1—O2	111.61 (7)	C13—C14—C9	121.66 (15)
O3—S1—O2	112.36 (7)	C13—C14—H14	119.2
O1—S1—C22	108.39 (7)	C9—C14—H14	119.2
O3—S1—C22	105.54 (7)	N2—C15—H15A	109.5
O2—S1—C22	105.59 (7)	N2—C15—H15B	109.5
C5—N1—C1	120.26 (14)	H15A—C15—H15B	109.5
C5—N1—C6	120.03 (13)	N2—C15—H15C	109.5
C1—N1—C6	119.69 (13)	H15A—C15—H15C	109.5
C12—N2—C15	119.93 (13)	H15B—C15—H15C	109.5
C12—N2—C16	120.42 (14)	N2—C16—H16A	109.5
C15—N2—C16	119.65 (14)	N2—C16—H16B	109.5
N1—C1—C2	120.76 (15)	H16A—C16—H16B	109.5
N1—C1—H1	119.6	N2—C16—H16C	109.5
C2—C1—H1	119.6	H16A—C16—H16C	109.5
C1—C2—C3	120.28 (15)	H16B—C16—H16C	109.5
C1—C2—H2	119.9	C18—C17—C22	118.60 (14)
C3—C2—H2	119.9	C18—C17—C23	117.57 (14)
C4—C3—C2	116.78 (15)	C22—C17—C23	123.74 (14)
C4—C3—C7	119.04 (15)	C19—C18—C17	122.41 (15)
C2—C3—C7	124.16 (15)	C19—C18—H18	118.8
C5—C4—C3	121.03 (16)	C17—C18—H18	118.8
C5—C4—H4	119.5	C18—C19—C20	117.74 (14)
C3—C4—H4	119.5	C18—C19—C24	121.92 (15)
N1—C5—C4	120.85 (15)	C20—C19—C24	120.33 (15)
N1—C5—H5	119.6	C19—C20—C21	122.50 (15)
C4—C5—H5	119.6	C19—C20—H20	118.7
N1—C6—H6A	109.5	C21—C20—H20	118.7
N1—C6—H6B	109.5	C20—C21—C22	118.52 (14)
H6A—C6—H6B	109.5	C20—C21—C25	116.73 (14)
N1—C6—H6C	109.5	C22—C21—C25	124.74 (14)
H6A—C6—H6C	109.5	C21—C22—C17	120.04 (14)
H6B—C6—H6C	109.5	C21—C22—S1	122.28 (12)
C8—C7—C3	123.74 (16)	C17—C22—S1	117.66 (11)
C8—C7—H7	118.1	C17—C23—H23A	109.5
C3—C7—H7	118.1	C17—C23—H23B	109.5
C7—C8—C9	126.30 (16)	H23A—C23—H23B	109.5
C7—C8—H8	116.9	C17—C23—H23C	109.5
C9—C8—H8	116.8	H23A—C23—H23C	109.5
C10—C9—C14	117.34 (15)	H23B—C23—H23C	109.5
C10—C9—C8	118.18 (15)	C19—C24—H24A	109.5
C14—C9—C8	124.46 (16)	C19—C24—H24B	109.5
C11—C10—C9	121.99 (15)	H24A—C24—H24B	109.5
C11—C10—H10	119.0	C19—C24—H24C	109.5
C9—C10—H10	119.0	H24A—C24—H24C	109.5
C10—C11—C12	120.65 (15)	H24B—C24—H24C	109.5
C10—C11—H11	119.7	C21—C25—H25A	109.5
C12—C11—H11	119.7	C21—C25—H25B	109.5
N2—C12—C13	121.89 (14)	H25A—C25—H25B	109.5
N2—C12—C11	120.30 (14)	C21—C25—H25C	109.5
C13—C12—C11	117.81 (14)	H25A—C25—H25C	109.5
C14—C13—C12	120.40 (15)	H25B—C25—H25C	109.5
C14—C13—H13	119.8	H4A—O4—H4B	105 (2)
C5—N1—C1—C2	−1.1 (2)	C12—C13—C14—C9	−0.6 (2)
C6—N1—C1—C2	−179.16 (14)	C10—C9—C14—C13	−2.6 (2)
N1—C1—C2—C3	0.4 (2)	C8—C9—C14—C13	176.07 (15)
C1—C2—C3—C4	1.1 (2)	C22—C17—C18—C19	2.7 (2)
C1—C2—C3—C7	−177.60 (15)	C23—C17—C18—C19	−173.92 (14)
C2—C3—C4—C5	−2.1 (2)	C17—C18—C19—C20	1.0 (2)
C7—C3—C4—C5	176.71 (15)	C17—C18—C19—C24	−179.96 (15)
C1—N1—C5—C4	0.1 (2)	C18—C19—C20—C21	−2.3 (2)
C6—N1—C5—C4	178.19 (15)	C24—C19—C20—C21	178.59 (15)
C3—C4—C5—N1	1.5 (3)	C19—C20—C21—C22	−0.1 (2)
C4—C3—C7—C8	−168.78 (16)	C19—C20—C21—C25	178.41 (16)
C2—C3—C7—C8	9.9 (3)	C20—C21—C22—C17	3.9 (2)
C3—C7—C8—C9	177.35 (15)	C25—C21—C22—C17	−174.51 (15)
C7—C8—C9—C10	175.50 (16)	C20—C21—C22—S1	−174.67 (12)
C7—C8—C9—C14	−3.2 (3)	C25—C21—C22—S1	7.0 (2)
C14—C9—C10—C11	2.8 (2)	C18—C17—C22—C21	−5.1 (2)
C8—C9—C10—C11	−175.95 (15)	C23—C17—C22—C21	171.28 (14)
C9—C10—C11—C12	0.2 (2)	C18—C17—C22—S1	173.46 (11)
C15—N2—C12—C13	179.87 (15)	C23—C17—C22—S1	−10.1 (2)
C16—N2—C12—C13	−0.7 (2)	O1—S1—C22—C21	4.19 (15)
C15—N2—C12—C11	0.6 (2)	O3—S1—C22—C21	125.28 (13)
C16—N2—C12—C11	−179.95 (15)	O2—S1—C22—C21	−115.53 (13)
C10—C11—C12—N2	175.85 (14)	O1—S1—C22—C17	−174.38 (11)
C10—C11—C12—C13	−3.4 (2)	O3—S1—C22—C17	−53.28 (13)
N2—C12—C13—C14	−175.66 (15)	O2—S1—C22—C17	65.90 (13)
C11—C12—C13—C14	3.6 (2)