4-{2-[4-(Dimethyl­amino)­phen­yl]ethen­yl}-1-methyl­pyridinium 2-amino-3,5-dimethyl­benzene­sulfonate monohydrate

Li, L.; Tao, X.; Yang, H.; Yang, Z.

doi:10.1107/S160053681200089X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o426-o427

doi:10.1107/S160053681200089X

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4-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridinium 2-amino-3,5-dimethylbenzenesulfonate monohydrate

Liang Li,^a Xutang Tao,^b Huai Yang ^a and Zhou Yang ^a ^*

^aDepartment of Materials Physics and Chemistry, School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083, People's Republic of China, and ^bState Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, People's Republic of China
^*Correspondence e-mail: yangz@ustb.edu.cn

(Received 18 December 2011; accepted 9 January 2012; online 18 January 2012)

In the crystal structure of the title compound, C₁₆H₁₉N₂⁺·C₈H₁₀NO₃S⁻·H₂O, the cations and anions are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming alternating layers parallel to the ac plane. An intramolecular N—H⋯O hydrogen bond occurs in the anion. The crystal structure is further stabilized by π–π interactions, with centroid–centroid distances of 3.7240 (9) and 3.6803 (8) Å.

Related literature

For the synthesis, see: Okada et al. (1990 ). For background to non-linear optical materials, see: Gu et al. (2003 ); Dorrer (2006 ); Yang, Mutter et al. (2007 ); Ruiz et al. (2006 ). For the effects of different substituents of benzene sulfonate on its non-linear optical properties, see: Okada et al. (2003 ); Yang, Wörle et al. (2007 ); Ogawa et al. (2008 ), Yang et al. (2005 ), Yang, Jazbinsek et al., (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₉N₂⁺·C₈H₁₀NO₃S⁻·H₂O
M_r = 457.58
Triclinic, $[P \overline 1]$
a = 8.7430 (17) Å
b = 9.5463 (19) Å
c = 14.109 (3) Å
α = 95.00 (3)°
β = 101.89 (3)°
γ = 96.29 (3)°
V = 1138.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 173 K
0.30 × 0.24 × 0.23 mm

Data collection

Rigaku MM007HF + CCD (Saturn724+) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.713, T_max = 1.000
8126 measured reflections
3986 independent reflections
3722 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 1.10
3986 reflections
294 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯O3	0.84	2.01	2.854 (2)	179
O4—H4A⋯O2ⁱ	0.84	2.04	2.874 (2)	172
N3—H3A⋯O1	0.89	1.96	2.732 (2)	144
N3—H3B⋯O4ⁱⁱ	0.89	2.27	3.110 (3)	158
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z+1.

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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200089X/zj2049sup1.cif

Supporting information file. DOI: 10.1107/S160053681200089X/zj2049Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S160053681200089X/zj2049Isup3.hkl

Supporting information file. DOI: 10.1107/S160053681200089X/zj2049Isup4.cml

checkCIF report

Comment top

There has been intensive research on the development of nonlinear optical materials for its potential application in high-speed and high-density data processing, storage and telecommunications. (Gu et al., 2003; Dorrer, 2006; Yang, Mutter et al., 2007). The title compound was synthesized as part of our continuing research on the nonlinear optical properties of DAS (4-N,N-dimethylamino-4'-N'-methyl-stilbazolium) derivatives. (Okada et al., 2003; Ogawa et al., 2008; Yang et al., 2005; Ruiz et al., 2006; Yang Wörle et al., 2007; Yang, Jazbinsek et al., 2007). Fig. 1 illustrates the molecular structure of organic salt with the atomic numbering scheme. The bond distances and angles in both the cation and anion are in normal ranges (Allen et al., 1987). The unit cell of the title compound contains two asymmetric units, each consisting of one C₁₆H₁₉N₂⁺ cation, one C₈H₅O₇S^- anion and one water molecule. In the crystal structure, atoms H3A and H3B are involved in N—H—O interactions, while atoms H4A and H4B are involved O—H—O hydrogen bonds. The distance of H3A—O1 and H3B—O4 are 1.96 Å and 2.27 Å, while the distance of H4B—O2 and H4B—O3 are 2.01 Å and 2.04 Å. The cations and anions are stacked in a parallel manner and form alternating layers. The crystal structure is further stabilized by π–π interactions with a Cg1···Cg1 and a Cg1···Cg2 separation of 3.6803 (8) Å and 3.7240 (9) Å, respectively (Cg1 and Cg2 are the centroids of the N2/C11—C15 pyridine ring and C3—C8 benzene ring, respectively).

Related literature top

For the synthesis, see: Okada et al. (1990). For background to non-linear optical materials, see: Gu et al. (2003); Dorrer (2006); Yang, Mutter et al. (2007); Ruiz et al. (2006). For the effects of different substituents of benzene sulfonate on its non-linear optical properties, see: Okada et al. (2003); Yang, Wörle et al. (2007); Ogawa et al. (2008), Yang et al. (2005), Yang, Jazbinsek et al., (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

4-N,N-dimethylamino-4'-N'-methyl-stilbazolium 2-amino-3,5-dimethylbenzenesulfonate was prepared by the metathesization of 4-N,N-dimethylamino-4'-N'-methyl-stilbazolium iodide (Okada et al., 1990) with the sodium salt of the 2-amino-3,5-dimethylbenzenesulfonic acid. The title salt was then recrystallized from methanol to get high purity material for crystal growth. 4-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridinium 2-amino-3,5-dimethylbenzenesulfonate monohydrate: yield 65%; ¹H-NMR (400 MHz, DMSO-d6): delta=8.68 (d, 2H, J= 6.8 Hz, C₅H₄N), 8.04(d, 2H, J= 6.8 Hz, C₅H₄N), 7.92 (d, 1H, J=16.0 Hz, CH), 7.60(d, 2H, J= 8.4 Hz, C₆H₄), 7.18 (m, 2H, J= 16.0 Hz, CH+C₆H₂SO₃^-), 6.80 (d, 2H, J= 8.8 Hz, C₆H₄), 6.73(s, 1H, C₆H₄SO₃^-),5.18(s, 2H, NH₂), 4.16(s, 3H, NMe), 3.01 (s, 6H, NMe₂), 2.10(s, 3H, Me), 2.01(s, 3H, Me). C, H, N analysis calcd. for C₂₄H₂₄N₂O₇S: C 65.58, H 6.65, N 9.56; found: C 65.60,H 6.67, N 9.53. Crystals were obtained by slow cooling method from 45^OC to room temperature in methanol: first the saturated solution of the title compound in methanol at 45°C was prepared. Spontaneous nucleation could be observed after cooling down the saturated solution. Then the temperature was increased to dissolve most of the nuclei and made sure that only one or two nucleated crystals remained undissolved. After that, large crystals with good quality for X-Ray measurements could be obtained by slow cooling the solution at the temperature of about 34°C.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title organic salt, viewed down the y axis. Hydrogen bonds are shown as dashed lines.

4-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridinium 2-amino-3,5-dimethylbenzenesulfonate monohydrate top

Crystal data top

C₁₆H₁₉N₂⁺·C₈H₁₀NO₃S⁻·H₂O	Z = 2
M_r = 457.58	F(000) = 488
Triclinic, P1	D_x = 1.335 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7430 (17) Å	Cell parameters from 4072 reflections
b = 9.5463 (19) Å	θ = 1.5–27.5°
c = 14.109 (3) Å	µ = 0.18 mm⁻¹
α = 95.00 (3)°	T = 173 K
β = 101.89 (3)°	Block, red
γ = 96.29 (3)°	0.30 × 0.24 × 0.23 mm
V = 1138.1 (4) Å³

Data collection top

Rigaku MM007HF + CCD (Saturn724+) diffractometer	3986 independent reflections
Radiation source: Rotating Anode	3722 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.032
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.8°
ω scans at fixed χ = 45°	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −11→10
T_min = 0.713, T_max = 1.000	l = −13→16
8126 measured reflections

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0533P)² + 0.5973P] where P = (F_o² + 2F_c²)/3
3986 reflections	(Δ/σ)_max < 0.001
294 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₉N₂⁺·C₈H₁₀NO₃S⁻·H₂O	γ = 96.29 (3)°
M_r = 457.58	V = 1138.1 (4) Å³
Triclinic, P1	Z = 2
a = 8.7430 (17) Å	Mo Kα radiation
b = 9.5463 (19) Å	µ = 0.18 mm⁻¹
c = 14.109 (3) Å	T = 173 K
α = 95.00 (3)°	0.30 × 0.24 × 0.23 mm
β = 101.89 (3)°

Data collection top

Rigaku MM007HF + CCD (Saturn724+) diffractometer	3986 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	3722 reflections with I > 2σ(I)
T_min = 0.713, T_max = 1.000	R_int = 0.032
8126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.10	Δρ_max = 0.27 e Å⁻³
3986 reflections	Δρ_min = −0.36 e Å⁻³
294 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.35960 (6)	−0.01854 (5)	0.64442 (4)	0.02452 (16)
O1	0.25159 (18)	−0.09428 (18)	0.55886 (11)	0.0414 (4)
O2	0.47733 (18)	−0.10464 (18)	0.68633 (12)	0.0413 (4)
O3	0.4275 (2)	0.12009 (16)	0.62811 (12)	0.0415 (4)
O4	0.33542 (17)	0.21476 (16)	0.44082 (11)	0.0359 (4)
H4B	0.3642	0.1870	0.4958	0.043*
H4A	0.3960	0.1802	0.4087	0.043*
N1	−0.1077 (2)	0.43155 (18)	0.10981 (14)	0.0323 (4)
N2	1.14453 (19)	0.57343 (18)	0.40983 (12)	0.0250 (4)
N3	−0.0089 (2)	−0.02843 (19)	0.62299 (13)	0.0313 (4)
H3A	0.0435	−0.0563	0.5784	0.038*
H3B	−0.1114	−0.0597	0.6115	0.038*
C1	−0.1983 (3)	0.5453 (2)	0.08007 (17)	0.0340 (5)
H1C	−0.1826	0.6198	0.1348	0.051*
H1A	−0.3105	0.5078	0.0601	0.051*
H1B	−0.1630	0.5849	0.0253	0.051*
C2	−0.1884 (3)	0.2877 (2)	0.0917 (2)	0.0419 (6)
H2A	−0.1506	0.2345	0.0405	0.063*
H2C	−0.3022	0.2896	0.0708	0.063*
H2B	−0.1670	0.2417	0.1517	0.063*
C3	0.0515 (2)	0.4578 (2)	0.14488 (14)	0.0246 (4)
C4	0.1328 (2)	0.5964 (2)	0.15746 (15)	0.0272 (4)
H4	0.0761	0.6733	0.1407	0.033*
C5	0.2934 (2)	0.6218 (2)	0.19382 (15)	0.0284 (5)
H5	0.3447	0.7163	0.2012	0.034*
C6	0.3837 (2)	0.5134 (2)	0.22030 (14)	0.0249 (4)
C7	0.3029 (2)	0.3751 (2)	0.20748 (14)	0.0261 (4)
H7	0.3600	0.2986	0.2245	0.031*
C8	0.1428 (2)	0.3481 (2)	0.17085 (15)	0.0265 (4)
H8	0.0922	0.2532	0.1628	0.032*
C9	0.5511 (2)	0.5491 (2)	0.26169 (14)	0.0264 (4)
H9	0.5922	0.6465	0.2676	0.032*
C10	0.6549 (2)	0.4597 (2)	0.29268 (15)	0.0267 (4)
H10	0.6164	0.3616	0.2870	0.032*
C11	0.8219 (2)	0.5027 (2)	0.33428 (14)	0.0249 (4)
C12	0.8933 (2)	0.6450 (2)	0.35356 (15)	0.0276 (4)
H12	0.8308	0.7194	0.3410	0.033*
C13	1.0521 (2)	0.6765 (2)	0.39030 (14)	0.0266 (4)
H13	1.0984	0.7729	0.4024	0.032*
C14	1.0799 (2)	0.4359 (2)	0.39385 (14)	0.0268 (4)
H14	1.1451	0.3637	0.4080	0.032*
C15	0.9215 (2)	0.3997 (2)	0.35749 (15)	0.0269 (4)
H15	0.8782	0.3025	0.3478	0.032*
C16	1.3155 (2)	0.6116 (2)	0.45006 (16)	0.0323 (5)
H16C	1.3328	0.6552	0.5175	0.049*
H16B	1.3593	0.6789	0.4109	0.049*
H16A	1.3678	0.5260	0.4484	0.049*
C17	−0.1655 (2)	0.0252 (2)	0.77634 (18)	0.0343 (5)
H17A	−0.2024	0.0886	0.7280	0.051*
H17C	−0.1968	0.0533	0.8373	0.051*
H17B	−0.2123	−0.0725	0.7518	0.051*
C18	0.0114 (2)	0.0350 (2)	0.79461 (16)	0.0264 (4)
C19	0.0835 (2)	0.00344 (19)	0.71531 (14)	0.0237 (4)
C20	0.2495 (2)	0.01369 (19)	0.73519 (14)	0.0228 (4)
C21	0.3380 (2)	0.0561 (2)	0.82936 (15)	0.0257 (4)
H21	0.4496	0.0628	0.8407	0.031*
C22	0.2692 (2)	0.0888 (2)	0.90665 (15)	0.0280 (5)
C23	0.3656 (3)	0.1396 (3)	1.00757 (17)	0.0408 (6)
H23A	0.4755	0.1241	1.0108	0.061*
H23C	0.3235	0.0868	1.0551	0.061*
H23B	0.3607	0.2410	1.0225	0.061*
C24	0.1045 (3)	0.0758 (2)	0.88675 (16)	0.0288 (5)
H24	0.0541	0.0959	0.9391	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0209 (3)	0.0246 (3)	0.0281 (3)	0.00316 (19)	0.0056 (2)	0.0024 (2)
O1	0.0290 (8)	0.0526 (10)	0.0371 (9)	0.0016 (7)	0.0053 (7)	−0.0147 (8)
O2	0.0332 (9)	0.0554 (10)	0.0448 (10)	0.0240 (8)	0.0159 (7)	0.0172 (8)
O3	0.0585 (11)	0.0287 (8)	0.0407 (9)	−0.0035 (7)	0.0239 (8)	0.0034 (7)
O4	0.0296 (8)	0.0451 (9)	0.0367 (9)	0.0135 (7)	0.0090 (7)	0.0098 (7)
N1	0.0238 (9)	0.0268 (9)	0.0430 (11)	0.0035 (7)	−0.0011 (8)	0.0057 (8)
N2	0.0225 (9)	0.0290 (9)	0.0237 (9)	0.0037 (7)	0.0060 (7)	0.0018 (7)
N3	0.0206 (9)	0.0381 (10)	0.0331 (10)	0.0039 (7)	0.0018 (7)	0.0027 (8)
C1	0.0278 (11)	0.0359 (12)	0.0390 (13)	0.0078 (9)	0.0047 (10)	0.0100 (10)
C2	0.0283 (12)	0.0344 (13)	0.0567 (16)	−0.0016 (10)	−0.0028 (11)	0.0071 (11)
C3	0.0235 (10)	0.0276 (10)	0.0230 (10)	0.0034 (8)	0.0054 (8)	0.0045 (8)
C4	0.0268 (11)	0.0246 (10)	0.0316 (11)	0.0062 (8)	0.0071 (9)	0.0050 (8)
C5	0.0289 (11)	0.0231 (10)	0.0329 (11)	0.0017 (8)	0.0070 (9)	0.0029 (8)
C6	0.0241 (10)	0.0294 (11)	0.0224 (10)	0.0043 (8)	0.0080 (8)	0.0011 (8)
C7	0.0275 (11)	0.0258 (10)	0.0272 (10)	0.0085 (8)	0.0074 (8)	0.0050 (8)
C8	0.0282 (11)	0.0230 (10)	0.0281 (11)	0.0013 (8)	0.0066 (9)	0.0024 (8)
C9	0.0270 (11)	0.0249 (10)	0.0279 (11)	0.0024 (8)	0.0086 (9)	0.0019 (8)
C10	0.0259 (10)	0.0247 (10)	0.0303 (11)	0.0021 (8)	0.0085 (9)	0.0024 (8)
C11	0.0265 (10)	0.0275 (10)	0.0227 (10)	0.0048 (8)	0.0087 (8)	0.0045 (8)
C12	0.0286 (11)	0.0272 (11)	0.0278 (11)	0.0076 (8)	0.0057 (9)	0.0046 (8)
C13	0.0284 (11)	0.0242 (10)	0.0269 (10)	0.0032 (8)	0.0061 (8)	0.0013 (8)
C14	0.0290 (11)	0.0263 (10)	0.0270 (10)	0.0086 (8)	0.0078 (9)	0.0033 (8)
C15	0.0280 (11)	0.0233 (10)	0.0306 (11)	0.0031 (8)	0.0087 (9)	0.0047 (8)
C16	0.0222 (11)	0.0418 (13)	0.0310 (11)	0.0036 (9)	0.0029 (9)	0.0005 (9)
C17	0.0238 (11)	0.0316 (12)	0.0502 (14)	0.0053 (9)	0.0119 (10)	0.0081 (10)
C18	0.0232 (10)	0.0196 (10)	0.0382 (12)	0.0044 (8)	0.0089 (9)	0.0059 (8)
C19	0.0228 (10)	0.0179 (9)	0.0307 (11)	0.0033 (8)	0.0049 (8)	0.0058 (8)
C20	0.0214 (10)	0.0179 (9)	0.0290 (10)	0.0037 (7)	0.0042 (8)	0.0044 (8)
C21	0.0204 (10)	0.0245 (10)	0.0313 (11)	0.0033 (8)	0.0027 (8)	0.0042 (8)
C22	0.0315 (11)	0.0239 (10)	0.0283 (11)	0.0062 (8)	0.0042 (9)	0.0039 (8)
C23	0.0431 (14)	0.0459 (14)	0.0325 (12)	0.0128 (11)	0.0040 (10)	0.0002 (10)
C24	0.0339 (11)	0.0236 (10)	0.0335 (11)	0.0076 (9)	0.0152 (9)	0.0051 (9)

Geometric parameters (Å, º) top

S1—O3	1.4470 (16)	C9—C10	1.347 (3)
S1—O1	1.4492 (17)	C9—H9	0.9500
S1—O2	1.4507 (16)	C10—C11	1.455 (3)
S1—C20	1.779 (2)	C10—H10	0.9500
O4—H4B	0.8400	C11—C15	1.399 (3)
O4—H4A	0.8401	C11—C12	1.411 (3)
N1—C3	1.365 (3)	C12—C13	1.368 (3)
N1—C2	1.450 (3)	C12—H12	0.9500
N1—C1	1.454 (3)	C13—H13	0.9500
N2—C13	1.352 (3)	C14—C15	1.368 (3)
N2—C14	1.352 (3)	C14—H14	0.9500
N2—C16	1.478 (3)	C15—H15	0.9500
N3—C19	1.373 (3)	C16—H16C	0.9800
N3—H3A	0.8902	C16—H16B	0.9800
N3—H3B	0.8900	C16—H16A	0.9800
C1—H1C	0.9800	C17—C18	1.505 (3)
C1—H1A	0.9800	C17—H17A	0.9800
C1—H1B	0.9800	C17—H17C	0.9800
C2—H2A	0.9800	C17—H17B	0.9800
C2—H2C	0.9800	C18—C24	1.382 (3)
C2—H2B	0.9800	C18—C19	1.419 (3)
C3—C4	1.410 (3)	C19—C20	1.411 (3)
C3—C8	1.413 (3)	C20—C21	1.394 (3)
C4—C5	1.379 (3)	C21—C22	1.379 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.399 (3)	C22—C24	1.399 (3)
C5—H5	0.9500	C22—C23	1.506 (3)
C6—C7	1.405 (3)	C23—H23A	0.9800
C6—C9	1.451 (3)	C23—H23C	0.9800
C7—C8	1.376 (3)	C23—H23B	0.9800
C7—H7	0.9500	C24—H24	0.9500
C8—H8	0.9500

O3—S1—O1	113.26 (11)	C15—C11—C12	116.18 (19)
O3—S1—O2	112.91 (11)	C15—C11—C10	119.85 (18)
O1—S1—O2	111.58 (10)	C12—C11—C10	123.98 (18)
O3—S1—C20	105.38 (9)	C13—C12—C11	120.40 (19)
O1—S1—C20	107.64 (9)	C13—C12—H12	119.8
O2—S1—C20	105.41 (9)	C11—C12—H12	119.8
H4B—O4—H4A	102.7	N2—C13—C12	121.43 (19)
C3—N1—C2	120.82 (18)	N2—C13—H13	119.3
C3—N1—C1	120.90 (17)	C12—C13—H13	119.3
C2—N1—C1	117.98 (17)	N2—C14—C15	120.57 (19)
C13—N2—C14	119.89 (17)	N2—C14—H14	119.7
C13—N2—C16	119.89 (17)	C15—C14—H14	119.7
C14—N2—C16	120.22 (17)	C14—C15—C11	121.51 (19)
C19—N3—H3A	113.8	C14—C15—H15	119.2
C19—N3—H3B	123.0	C11—C15—H15	119.2
H3A—N3—H3B	117.1	N2—C16—H16C	109.5
N1—C1—H1C	109.5	N2—C16—H16B	109.5
N1—C1—H1A	109.5	H16C—C16—H16B	109.5
H1C—C1—H1A	109.5	N2—C16—H16A	109.5
N1—C1—H1B	109.5	H16C—C16—H16A	109.5
H1C—C1—H1B	109.5	H16B—C16—H16A	109.5
H1A—C1—H1B	109.5	C18—C17—H17A	109.5
N1—C2—H2A	109.5	C18—C17—H17C	109.5
N1—C2—H2C	109.5	H17A—C17—H17C	109.5
H2A—C2—H2C	109.5	C18—C17—H17B	109.5
N1—C2—H2B	109.5	H17A—C17—H17B	109.5
H2A—C2—H2B	109.5	H17C—C17—H17B	109.5
H2C—C2—H2B	109.5	C24—C18—C19	119.59 (18)
N1—C3—C4	121.40 (18)	C24—C18—C17	121.22 (19)
N1—C3—C8	121.85 (18)	C19—C18—C17	119.19 (19)
C4—C3—C8	116.75 (18)	N3—C19—C20	123.04 (18)
C5—C4—C3	120.87 (19)	N3—C19—C18	119.28 (18)
C5—C4—H4	119.6	C20—C19—C18	117.60 (18)
C3—C4—H4	119.6	C21—C20—C19	120.54 (18)
C4—C5—C6	122.42 (19)	C21—C20—S1	115.75 (15)
C4—C5—H5	118.8	C19—C20—S1	123.67 (15)
C6—C5—H5	118.8	C22—C21—C20	122.29 (19)
C5—C6—C7	116.73 (18)	C22—C21—H21	118.9
C5—C6—C9	119.24 (18)	C20—C21—H21	118.9
C7—C6—C9	124.00 (19)	C21—C22—C24	116.84 (19)
C8—C7—C6	121.48 (19)	C21—C22—C23	122.0 (2)
C8—C7—H7	119.3	C24—C22—C23	121.1 (2)
C6—C7—H7	119.3	C22—C23—H23A	109.5
C7—C8—C3	121.73 (18)	C22—C23—H23C	109.5
C7—C8—H8	119.1	H23A—C23—H23C	109.5
C3—C8—H8	119.1	C22—C23—H23B	109.5
C10—C9—C6	127.36 (19)	H23A—C23—H23B	109.5
C10—C9—H9	116.3	H23C—C23—H23B	109.5
C6—C9—H9	116.3	C18—C24—C22	123.12 (19)
C9—C10—C11	124.62 (19)	C18—C24—H24	118.4
C9—C10—H10	117.7	C22—C24—H24	118.4
C11—C10—H10	117.7

C2—N1—C3—C4	176.3 (2)	N2—C14—C15—C11	1.0 (3)
C1—N1—C3—C4	2.7 (3)	C12—C11—C15—C14	−2.0 (3)
C2—N1—C3—C8	−4.1 (3)	C10—C11—C15—C14	177.92 (19)
C1—N1—C3—C8	−177.65 (19)	C24—C18—C19—N3	−175.99 (18)
N1—C3—C4—C5	179.38 (19)	C17—C18—C19—N3	3.2 (3)
C8—C3—C4—C5	−0.3 (3)	C24—C18—C19—C20	0.8 (3)
C3—C4—C5—C6	−0.3 (3)	C17—C18—C19—C20	−179.99 (17)
C4—C5—C6—C7	0.5 (3)	N3—C19—C20—C21	175.45 (18)
C4—C5—C6—C9	−177.54 (19)	C18—C19—C20—C21	−1.2 (3)
C5—C6—C7—C8	−0.1 (3)	N3—C19—C20—S1	−2.0 (3)
C9—C6—C7—C8	177.76 (19)	C18—C19—C20—S1	−178.72 (14)
C6—C7—C8—C3	−0.4 (3)	O3—S1—C20—C21	−72.98 (17)
N1—C3—C8—C7	−179.06 (19)	O1—S1—C20—C21	165.88 (15)
C4—C3—C8—C7	0.6 (3)	O2—S1—C20—C21	46.66 (17)
C5—C6—C9—C10	178.8 (2)	O3—S1—C20—C19	104.61 (18)
C7—C6—C9—C10	0.9 (3)	O1—S1—C20—C19	−16.53 (19)
C6—C9—C10—C11	−179.54 (19)	O2—S1—C20—C19	−135.75 (17)
C9—C10—C11—C15	−175.28 (19)	C19—C20—C21—C22	0.4 (3)
C9—C10—C11—C12	4.7 (3)	S1—C20—C21—C22	178.10 (15)
C15—C11—C12—C13	1.8 (3)	C20—C21—C22—C24	0.8 (3)
C10—C11—C12—C13	−178.17 (19)	C20—C21—C22—C23	−177.79 (19)
C14—N2—C13—C12	−0.6 (3)	C19—C18—C24—C22	0.4 (3)
C16—N2—C13—C12	−179.62 (18)	C17—C18—C24—C22	−178.75 (18)
C11—C12—C13—N2	−0.5 (3)	C21—C22—C24—C18	−1.2 (3)
C13—N2—C14—C15	0.4 (3)	C23—C22—C24—C18	177.38 (19)
C16—N2—C14—C15	179.38 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O3	0.84	2.01	2.854 (2)	179
O4—H4A···O2ⁱ	0.84	2.04	2.874 (2)	172
N3—H3A···O1	0.89	1.96	2.732 (2)	144
N3—H3B···O4ⁱⁱ	0.89	2.27	3.110 (3)	158

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₂⁺·C₈H₁₀NO₃S⁻·H₂O
M_r	457.58
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.7430 (17), 9.5463 (19), 14.109 (3)
α, β, γ (°)	95.00 (3), 101.89 (3), 96.29 (3)
V (Å³)	1138.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.24 × 0.23

Data collection
Diffractometer	Rigaku MM007HF + CCD (Saturn724+) diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.713, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8126, 3986, 3722
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.10
No. of reflections	3986
No. of parameters	294
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.36

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O3	0.84	2.01	2.854 (2)	178.5
O4—H4A···O2ⁱ	0.84	2.04	2.874 (2)	171.8
N3—H3A···O1	0.89	1.96	2.732 (2)	143.8
N3—H3B···O4ⁱⁱ	0.89	2.27	3.110 (3)	157.5

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

Acknowledgements

The authors thank the National Natural Science Foundation (grant No. 50803005), the Fundamental Research Funds for the Central Universities, the Scientific Research Foundation for Returned Overseas Chinese Scholars and the National Natural Science Fund for Distinguished Young Scholars (grant No. 51025313).

References

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Volume 68| Part 2| February 2012| Pages o426-o427

doi:10.1107/S160053681200089X

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

4-{2-[4-(Di­methyl­amino)­phen­yl]ethen­yl}-1-methyl­pyridinium 2-amino-3,5-di­methyl­benzene­sulfonate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridinium 2-amino-3,5-dimethylbenzenesulfonate monohydrate