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In the title compound, C15H16NO2+·C7H7O3S, the cation is almost planar and makes a dihedral angle of 83.1 (1)° with the benzene ring of the anion. In the crystal structure, alternate layers of anions and cations are interconnected by O—H...O hydrogen bonds, C—H...O and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023286/ci6286sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023286/ci6286Isup2.hkl
Contains datablock I

CCDC reference: 227015

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.065
  • wR factor = 0.155
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... S1
Alert level C PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.01
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

4-[(4-hydroxy-3-methoxyphenyl)ethenyl]-N-methylpyridinium p-toluenesulfonate top
Crystal data top
C15H16NO2+·C7H7O3SZ = 2
Mr = 413.47F(000) = 436
Triclinic, P1Dx = 1.376 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7154 (16) ÅCell parameters from 4331 reflections
b = 10.4598 (17) Åθ = 2.1–27.7°
c = 10.6997 (18) ŵ = 0.20 mm1
α = 110.436 (4)°T = 293 K
β = 94.184 (4)°Block, red
γ = 98.581 (3)°0.38 × 0.20 × 0.18 mm
V = 998.3 (3) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
3518 independent reflections
Radiation source: fine-focus sealed tube3251 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.1°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.896, Tmax = 0.966l = 1212
10593 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0594P)2 + 0.884P]
where P = (Fo2 + 2Fc2)/3
3518 reflections(Δ/σ)max = 0.001
269 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.41 e Å3
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
xyzUiso*/Ueq
S10.12655 (8)0.48537 (8)0.74266 (8)0.0458 (2)
O10.3255 (3)0.0721 (2)0.0448 (2)0.0637 (7)
H1O0.225 (4)0.240 (4)0.138 (4)0.066 (11)*
O20.2442 (3)0.1627 (2)0.1093 (2)0.0600 (7)
O30.1265 (3)0.6238 (3)0.8381 (3)0.0869 (9)
O40.1670 (3)0.4667 (5)0.6072 (3)0.1146 (13)
O50.2036 (2)0.3844 (3)0.7847 (3)0.0688 (7)
N11.0075 (3)0.0736 (2)0.7222 (2)0.0462 (6)
C10.4924 (3)0.0084 (3)0.2483 (3)0.0450 (7)
H10.52220.07630.22510.054*
C20.3909 (3)0.0258 (3)0.1632 (3)0.0424 (7)
C30.3447 (3)0.1529 (3)0.1976 (3)0.0419 (7)
C40.4017 (3)0.2585 (3)0.3173 (3)0.0462 (7)
H40.37060.34260.34140.055*
C50.5048 (3)0.2401 (3)0.4018 (3)0.0480 (7)
H50.54320.31280.48190.058*
C60.5520 (3)0.1157 (3)0.3695 (3)0.0421 (7)
C70.6581 (3)0.1000 (3)0.4638 (3)0.0467 (7)
H70.69040.17640.54270.056*
C80.7133 (3)0.0119 (3)0.4486 (3)0.0471 (7)
H80.68380.08740.36840.056*
C90.8157 (3)0.0281 (3)0.5456 (3)0.0423 (7)
C100.8651 (3)0.0708 (3)0.6728 (3)0.0485 (7)
H100.83340.15480.70030.058*
C110.9595 (3)0.0456 (3)0.7575 (3)0.0499 (7)
H110.99160.11320.84230.060*
C120.9624 (4)0.1705 (3)0.6002 (3)0.0552 (8)
H120.99580.25350.57530.066*
C130.8688 (3)0.1499 (3)0.5121 (3)0.0532 (8)
H130.83960.21880.42750.064*
C141.1089 (4)0.0993 (4)0.8159 (4)0.0628 (9)
H14A1.18760.12790.77160.094*
H14B1.06430.17110.84410.094*
H14C1.14080.01560.89320.094*
C150.3604 (5)0.2069 (3)0.0070 (4)0.0748 (12)
H15A0.30960.26490.07960.112*
H15B0.33570.24680.07250.112*
H15C0.45950.19970.00270.112*
C160.0515 (3)0.4664 (3)0.7578 (3)0.0378 (6)
C170.1410 (3)0.5019 (3)0.6762 (3)0.0418 (7)
H170.10790.53520.61200.050*
C180.2785 (3)0.4882 (3)0.6899 (3)0.0452 (7)
H180.33780.51140.63360.054*
C190.3317 (3)0.4406 (3)0.7858 (3)0.0443 (7)
C200.2404 (3)0.4060 (3)0.8668 (3)0.0453 (7)
H200.27370.37360.93170.054*
C210.1015 (3)0.4181 (3)0.8540 (3)0.0421 (7)
H210.04170.39400.90950.051*
C220.4825 (4)0.4261 (4)0.7998 (4)0.0690 (10)
H22A0.50320.40300.87760.103*
H22B0.54170.51230.80990.103*
H22C0.49930.35390.72090.103*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0375 (4)0.0515 (5)0.0506 (5)0.0154 (3)0.0007 (3)0.0198 (4)
O10.0846 (17)0.0449 (12)0.0509 (13)0.0300 (12)0.0226 (12)0.0033 (10)
O20.0699 (16)0.0471 (13)0.0573 (14)0.0286 (12)0.0179 (11)0.0104 (11)
O30.0643 (17)0.0518 (15)0.136 (3)0.0311 (13)0.0014 (16)0.0184 (16)
O40.0553 (17)0.233 (4)0.0714 (19)0.030 (2)0.0056 (14)0.077 (2)
O50.0432 (13)0.0671 (16)0.108 (2)0.0180 (11)0.0195 (13)0.0412 (15)
N10.0450 (14)0.0459 (14)0.0486 (15)0.0065 (11)0.0079 (11)0.0219 (12)
C10.0502 (17)0.0400 (16)0.0474 (17)0.0184 (13)0.0007 (13)0.0161 (13)
C20.0492 (17)0.0389 (15)0.0375 (15)0.0145 (13)0.0023 (13)0.0110 (12)
C30.0430 (16)0.0420 (15)0.0440 (16)0.0130 (12)0.0008 (12)0.0190 (13)
C40.0536 (18)0.0358 (15)0.0488 (17)0.0124 (13)0.0010 (14)0.0144 (13)
C50.0520 (18)0.0429 (16)0.0443 (17)0.0055 (14)0.0039 (14)0.0135 (13)
C60.0421 (16)0.0436 (16)0.0423 (16)0.0081 (12)0.0001 (12)0.0189 (13)
C70.0493 (17)0.0462 (17)0.0431 (16)0.0072 (14)0.0020 (13)0.0168 (13)
C80.0507 (18)0.0457 (17)0.0407 (16)0.0056 (14)0.0084 (13)0.0151 (13)
C90.0407 (15)0.0419 (16)0.0441 (16)0.0033 (12)0.0027 (12)0.0191 (13)
C100.0545 (18)0.0427 (16)0.0481 (17)0.0130 (14)0.0015 (14)0.0162 (14)
C110.0548 (19)0.0468 (17)0.0412 (16)0.0064 (14)0.0052 (14)0.0111 (13)
C120.062 (2)0.0412 (17)0.059 (2)0.0139 (15)0.0117 (16)0.0155 (15)
C130.0580 (19)0.0408 (16)0.0507 (18)0.0081 (14)0.0135 (15)0.0091 (14)
C140.056 (2)0.073 (2)0.064 (2)0.0127 (17)0.0159 (16)0.0345 (19)
C150.104 (3)0.0466 (19)0.059 (2)0.034 (2)0.022 (2)0.0007 (16)
C160.0392 (15)0.0353 (14)0.0341 (14)0.0101 (11)0.0001 (11)0.0065 (11)
C170.0486 (17)0.0371 (15)0.0387 (15)0.0097 (12)0.0022 (12)0.0125 (12)
C180.0423 (16)0.0435 (16)0.0465 (17)0.0048 (13)0.0095 (13)0.0131 (13)
C190.0363 (15)0.0429 (16)0.0441 (16)0.0084 (12)0.0006 (12)0.0052 (13)
C200.0478 (17)0.0498 (17)0.0385 (15)0.0146 (13)0.0045 (13)0.0164 (13)
C210.0403 (15)0.0495 (17)0.0379 (15)0.0120 (13)0.0044 (12)0.0163 (13)
C220.0433 (19)0.088 (3)0.076 (2)0.0189 (18)0.0044 (17)0.029 (2)
Geometric parameters (Å, º) top
S1—O41.410 (3)C10—C111.361 (4)
S1—O51.422 (2)C10—H100.93
S1—O31.452 (3)C11—H110.93
S1—C161.773 (3)C12—C131.355 (4)
O1—C21.357 (3)C12—H120.93
O1—C151.425 (4)C13—H130.93
O2—C31.349 (3)C14—H14A0.96
O2—H1O0.81 (4)C14—H14B0.96
N1—C121.336 (4)C14—H14C0.96
N1—C111.336 (4)C15—H15A0.96
N1—C141.474 (4)C15—H15B0.96
C1—C21.368 (4)C15—H15C0.96
C1—C61.399 (4)C16—C171.376 (4)
C1—H10.93C16—C211.384 (4)
C2—C31.402 (4)C17—C181.368 (4)
C3—C41.376 (4)C17—H170.93
C4—C51.380 (4)C18—C191.387 (4)
C4—H40.93C18—H180.93
C5—C61.382 (4)C19—C201.379 (4)
C5—H50.93C19—C221.497 (4)
C6—C71.457 (4)C20—C211.376 (4)
C7—C81.324 (4)C20—H200.93
C7—H70.93C21—H210.93
C8—C91.456 (4)C22—H22A0.96
C8—H80.93C22—H22B0.96
C9—C131.386 (4)C22—H22C0.96
C9—C101.388 (4)
O4—S1—O5113.7 (2)C10—C11—H11119.1
O4—S1—O3114.4 (2)N1—C12—C13121.1 (3)
O5—S1—O3109.93 (18)N1—C12—H12119.5
O4—S1—C16107.18 (15)C13—C12—H12119.5
O5—S1—C16106.58 (13)C12—C13—C9121.3 (3)
O3—S1—C16104.29 (14)C12—C13—H13119.4
C2—O1—C15117.9 (2)C9—C13—H13119.4
C3—O2—H1O109 (3)N1—C14—H14A109.5
C12—N1—C11119.3 (3)N1—C14—H14B109.5
C12—N1—C14119.8 (3)H14A—C14—H14B109.5
C11—N1—C14120.9 (3)N1—C14—H14C109.5
C2—C1—C6121.2 (3)H14A—C14—H14C109.5
C2—C1—H1119.4H14B—C14—H14C109.5
C6—C1—H1119.4O1—C15—H15A109.5
O1—C2—C1125.6 (3)O1—C15—H15B109.5
O1—C2—C3114.5 (2)H15A—C15—H15B109.5
C1—C2—C3119.8 (3)O1—C15—H15C109.5
O2—C3—C4124.0 (3)H15A—C15—H15C109.5
O2—C3—C2116.7 (3)H15B—C15—H15C109.5
C4—C3—C2119.3 (3)C17—C16—C21119.8 (3)
C3—C4—C5120.3 (3)C17—C16—S1120.5 (2)
C3—C4—H4119.8C21—C16—S1119.7 (2)
C5—C4—H4119.8C18—C17—C16119.9 (3)
C4—C5—C6121.2 (3)C18—C17—H17120.1
C4—C5—H5119.4C16—C17—H17120.1
C6—C5—H5119.4C17—C18—C19121.6 (3)
C5—C6—C1118.1 (3)C17—C18—H18119.2
C5—C6—C7119.1 (3)C19—C18—H18119.2
C1—C6—C7122.7 (3)C20—C19—C18117.6 (3)
C8—C7—C6126.6 (3)C20—C19—C22121.3 (3)
C8—C7—H7116.7C18—C19—C22121.1 (3)
C6—C7—H7116.7C21—C20—C19121.7 (3)
C7—C8—C9126.1 (3)C21—C20—H20119.2
C7—C8—H8117.0C19—C20—H20119.2
C9—C8—H8117.0C20—C21—C16119.4 (3)
C13—C9—C10116.3 (3)C20—C21—H21120.3
C13—C9—C8119.2 (3)C16—C21—H21120.3
C10—C9—C8124.5 (3)C19—C22—H22A109.5
C11—C10—C9120.3 (3)C19—C22—H22B109.5
C11—C10—H10119.8H22A—C22—H22B109.5
C9—C10—H10119.8C19—C22—H22C109.5
N1—C11—C10121.8 (3)H22A—C22—H22C109.5
N1—C11—H11119.1H22B—C22—H22C109.5
C15—O1—C2—C12.6 (5)C14—N1—C11—C10179.5 (3)
C15—O1—C2—C3176.1 (3)C9—C10—C11—N10.2 (5)
C6—C1—C2—O1179.0 (3)C11—N1—C12—C130.2 (5)
C6—C1—C2—C30.3 (5)C14—N1—C12—C13179.8 (3)
O1—C2—C3—O21.0 (4)N1—C12—C13—C90.5 (5)
C1—C2—C3—O2179.8 (3)C10—C9—C13—C120.7 (5)
O1—C2—C3—C4178.4 (3)C8—C9—C13—C12178.8 (3)
C1—C2—C3—C40.4 (5)O4—S1—C16—C1730.1 (3)
O2—C3—C4—C5179.7 (3)O5—S1—C16—C17152.1 (2)
C2—C3—C4—C50.9 (5)O3—S1—C16—C1791.6 (3)
C3—C4—C5—C60.8 (5)O4—S1—C16—C21151.1 (3)
C4—C5—C6—C10.1 (5)O5—S1—C16—C2129.1 (3)
C4—C5—C6—C7178.3 (3)O3—S1—C16—C2187.2 (3)
C2—C1—C6—C50.5 (5)C21—C16—C17—C180.5 (4)
C2—C1—C6—C7178.7 (3)S1—C16—C17—C18179.3 (2)
C5—C6—C7—C8179.5 (3)C16—C17—C18—C190.8 (4)
C1—C6—C7—C81.2 (5)C17—C18—C19—C200.6 (4)
C6—C7—C8—C9177.7 (3)C17—C18—C19—C22180.0 (3)
C7—C8—C9—C13176.9 (3)C18—C19—C20—C210.1 (4)
C7—C8—C9—C103.7 (5)C22—C19—C20—C21179.6 (3)
C13—C9—C10—C110.4 (5)C19—C20—C21—C160.1 (4)
C8—C9—C10—C11179.0 (3)C17—C16—C21—C200.1 (4)
C12—N1—C11—C100.5 (5)S1—C16—C21—C20178.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O···O3i0.81 (4)1.79 (4)2.567 (4)160 (4)
C10—H10···O5ii0.932.353.266 (5)170
C14—H14B···O3iii0.962.603.501 (5)157
C14—H14C···O2iv0.962.433.378 (5)167
C17—H17···O4i0.932.453.186 (5)136
C13—H13···Cg1v0.932.593.479 (3)161
C15—H15A···Cg1vi0.962.833.616 (4)140
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y1, z; (iv) x+1, y, z+1; (v) x+1, y, z+1; (vi) x, y1, z1.
 

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