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In the title compound, C15H16NO2+·C6H4BrSO3, the cation is almost planar. The benzene ring of the anion makes dihedral angles of 82.00 (8) and 74.96 (8)° with the mean planes through the benzene ring of the cation and the pyridinium ring, respectively. In the solid state, the cations and anions are packed as alternate layers parallel to the ac plane. These layers are interconnected through O—H...O, C—H...O and C—H...π interactions to form a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011086/ci6556sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011086/ci6556Isup2.hkl
Contains datablock I

CCDC reference: 271835

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.092
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Author Response: The high angle reflections are very weak.

Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for S1 PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O1 .. 2.99 Ang.
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H21D .. CG1 .. 2.84 Ang.
1 ALERT level A = In general: serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 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, 2003).

4(4'-Hydroxy-3'-methoxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate top
Crystal data top
C15H16NO2+·C6H4BrO3SZ = 2
Mr = 478.35F(000) = 488
Triclinic, P1Dx = 1.583 Mg m3
Hall symbol: -P 1Melting point: 515-516 K K
a = 9.9319 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3666 (8) ÅCell parameters from 4970 reflections
c = 10.5606 (8) Åθ = 2.1–28.3°
α = 109.71 (1)°µ = 2.19 mm1
β = 94.138 (1)°T = 293 K
γ = 98.458 (1)°Plate, pale yellow
V = 1003.79 (15) Å30.47 × 0.24 × 0.21 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4970 independent reflections
Radiation source: fine-focus sealed tube3596 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.1°
ω scanh = 1213
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1213
Tmin = 0.543, Tmax = 0.638l = 1413
6754 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.584P]
where P = (Fo2 + 2Fc2)/3
4118 reflections(Δ/σ)max = 0.002
264 parametersΔρmax = 0.70 e Å3
12 restraintsΔρmin = 0.42 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
Br11.01679 (3)0.42000 (3)0.29816 (3)0.04784 (11)
S10.38479 (6)0.48268 (7)0.24218 (7)0.04138 (16)
O10.3131 (2)0.3946 (2)0.3039 (2)0.0563 (5)
O20.3413 (2)0.4401 (4)0.1008 (3)0.1080 (12)
O30.3872 (3)0.6267 (2)0.3204 (4)0.1027 (11)
O40.2573 (2)0.1677 (2)0.6065 (2)0.0543 (5)
H40.28960.23740.64310.081*
O50.1747 (2)0.0686 (2)0.53882 (19)0.0554 (6)
N10.5043 (2)0.0693 (2)1.2192 (2)0.0420 (5)
C10.5595 (2)0.4651 (2)0.2588 (2)0.0325 (5)
C20.6454 (3)0.5013 (3)0.1733 (2)0.0363 (5)
H20.61130.53430.10810.044*
C30.7818 (3)0.4881 (3)0.1857 (2)0.0367 (5)
H30.84010.51180.12880.044*
C40.8304 (2)0.4393 (2)0.2835 (2)0.0346 (5)
C50.7464 (3)0.4037 (3)0.3691 (2)0.0380 (5)
H50.78080.37090.43430.046*
C60.6098 (3)0.4173 (3)0.3567 (2)0.0364 (5)
H60.55190.39410.41420.044*
C70.0017 (3)0.2406 (3)0.9005 (3)0.0431 (6)
H70.03530.31250.98150.052*
C80.1033 (3)0.2606 (3)0.8159 (3)0.0425 (6)
H80.13470.34480.84090.051*
C90.1580 (3)0.1562 (3)0.6949 (2)0.0382 (5)
C100.1112 (3)0.0283 (3)0.6590 (2)0.0385 (5)
C110.0117 (3)0.0093 (3)0.7443 (2)0.0399 (6)
H110.01830.07550.72050.048*
C120.0457 (3)0.1163 (3)0.8672 (2)0.0384 (5)
C130.1499 (3)0.0995 (3)0.9614 (3)0.0414 (6)
H130.17990.17511.04140.050*
C140.2066 (3)0.0117 (3)0.9456 (3)0.0423 (6)
H140.17810.08710.86520.051*
C150.3093 (3)0.0270 (3)1.0424 (2)0.0379 (5)
C160.3678 (3)0.1454 (3)1.0073 (3)0.0458 (6)
H160.34130.21330.92160.055*
C170.4634 (3)0.1650 (3)1.0950 (3)0.0486 (7)
H170.50060.24581.06830.058*
C180.4510 (3)0.0476 (3)1.2568 (3)0.0461 (6)
H180.48030.11421.34270.055*
C190.3550 (3)0.0713 (3)1.1725 (3)0.0448 (6)
H190.31970.15311.20150.054*
C200.6072 (3)0.0936 (4)1.3124 (3)0.0588 (8)
H20A0.68050.12761.26420.088*
H20B0.56480.16121.34790.088*
H20C0.64320.00781.38580.088*
C210.1394 (4)0.2034 (3)0.5003 (3)0.0662 (10)
H21D0.19280.26230.41560.099*
H21A0.15800.24280.56880.099*
H21B0.04350.19620.49040.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02899 (15)0.0620 (2)0.05246 (17)0.01567 (13)0.00234 (11)0.01766 (13)
S10.0273 (3)0.0484 (4)0.0513 (4)0.0117 (3)0.0001 (3)0.0204 (3)
O10.0336 (10)0.0673 (14)0.0798 (14)0.0180 (10)0.0168 (10)0.0355 (11)
O20.0406 (13)0.229 (4)0.0666 (15)0.0135 (18)0.0052 (11)0.074 (2)
O30.0467 (14)0.0444 (13)0.209 (3)0.0228 (12)0.0075 (17)0.0312 (17)
O40.0581 (13)0.0480 (11)0.0535 (11)0.0277 (10)0.0119 (9)0.0101 (9)
O50.0710 (14)0.0412 (10)0.0457 (10)0.0252 (10)0.0186 (9)0.0037 (8)
N10.0386 (12)0.0427 (12)0.0442 (11)0.0024 (10)0.0100 (9)0.0199 (9)
C10.0279 (12)0.0330 (12)0.0332 (11)0.0093 (10)0.0003 (9)0.0066 (9)
C20.0371 (13)0.0365 (13)0.0374 (12)0.0110 (11)0.0019 (10)0.0144 (10)
C30.0329 (13)0.0377 (13)0.0387 (12)0.0046 (11)0.0066 (10)0.0128 (10)
C40.0255 (11)0.0345 (12)0.0380 (12)0.0081 (10)0.0012 (9)0.0053 (9)
C50.0361 (13)0.0463 (14)0.0330 (11)0.0144 (12)0.0006 (9)0.0139 (10)
C60.0320 (12)0.0438 (14)0.0338 (11)0.0083 (11)0.0049 (9)0.0134 (10)
C70.0494 (16)0.0373 (13)0.0388 (12)0.0067 (12)0.0036 (11)0.0109 (10)
C80.0489 (16)0.0345 (13)0.0452 (13)0.0145 (12)0.0028 (11)0.0134 (10)
C90.0381 (14)0.0385 (13)0.0415 (12)0.0132 (11)0.0008 (10)0.0171 (10)
C100.0413 (14)0.0362 (13)0.0363 (12)0.0116 (11)0.0014 (10)0.0099 (10)
C110.0420 (14)0.0383 (13)0.0426 (13)0.0153 (12)0.0008 (11)0.0162 (10)
C120.0354 (13)0.0422 (14)0.0393 (12)0.0057 (12)0.0013 (10)0.0185 (10)
C130.0416 (15)0.0415 (14)0.0402 (12)0.0058 (12)0.0031 (11)0.0158 (11)
C140.0427 (15)0.0405 (14)0.0409 (13)0.0054 (12)0.0048 (11)0.0140 (11)
C150.0353 (13)0.0381 (13)0.0418 (13)0.0024 (11)0.0009 (10)0.0190 (10)
C160.0484 (16)0.0381 (14)0.0440 (14)0.0068 (13)0.0126 (11)0.0097 (11)
C170.0502 (17)0.0387 (14)0.0527 (15)0.0113 (13)0.0102 (12)0.0129 (12)
C180.0516 (17)0.0438 (15)0.0368 (13)0.0028 (13)0.0028 (11)0.0104 (11)
C190.0504 (16)0.0396 (14)0.0454 (14)0.0124 (13)0.0029 (12)0.0151 (11)
C200.0508 (18)0.071 (2)0.0573 (17)0.0086 (16)0.0162 (14)0.0319 (15)
C210.094 (3)0.0423 (16)0.0521 (17)0.0308 (17)0.0162 (16)0.0017 (13)
Geometric parameters (Å, º) top
Br1—C41.892 (2)C8—C91.376 (4)
S1—O21.420 (3)C8—H80.93
S1—O11.429 (2)C9—C101.410 (3)
S1—O31.438 (3)C10—C111.368 (3)
S1—C11.774 (2)C11—C121.406 (4)
O4—C91.354 (3)C11—H110.93
O4—H40.82C12—C131.453 (3)
O5—C101.363 (3)C13—C141.322 (4)
O5—C211.422 (3)C13—H130.93
N1—C171.341 (3)C14—C151.455 (3)
N1—C181.343 (4)C14—H140.93
N1—C201.474 (3)C15—C161.385 (4)
C1—C61.382 (3)C15—C191.400 (4)
C1—C21.388 (3)C16—C171.362 (4)
C2—C31.382 (3)C16—H160.93
C2—H20.93C17—H170.93
C3—C41.382 (3)C18—C191.361 (4)
C3—H30.93C18—H180.93
C4—C51.375 (4)C19—H190.93
C5—C61.386 (3)C20—H20A0.96
C5—H50.93C20—H20B0.96
C6—H60.93C20—H20C0.96
C7—C121.380 (4)C21—H21D0.96
C7—C81.384 (4)C21—H21A0.96
C7—H70.93C21—H21B0.96
O2—S1—O1112.76 (17)C11—C10—C9119.8 (2)
O2—S1—O3116.3 (2)C10—C11—C12121.0 (2)
O1—S1—O3110.35 (18)C10—C11—H11119.5
O2—S1—C1106.19 (14)C12—C11—H11119.5
O1—S1—C1106.50 (12)C7—C12—C11118.3 (2)
O3—S1—C1103.78 (13)C7—C12—C13119.0 (2)
C9—O4—H4109.5C11—C12—C13122.6 (2)
C10—O5—C21117.6 (2)C14—C13—C12127.0 (2)
C17—N1—C18119.3 (2)C14—C13—H13116.5
C17—N1—C20119.7 (2)C12—C13—H13116.5
C18—N1—C20121.0 (2)C13—C14—C15126.1 (2)
C6—C1—C2120.4 (2)C13—C14—H14117.0
C6—C1—S1120.25 (19)C15—C14—H14117.0
C2—C1—S1119.32 (18)C16—C15—C19116.0 (2)
C3—C2—C1119.7 (2)C16—C15—C14119.6 (2)
C3—C2—H2120.2C19—C15—C14124.4 (2)
C1—C2—H2120.2C17—C16—C15121.7 (2)
C4—C3—C2119.2 (2)C17—C16—H16119.2
C4—C3—H3120.4C15—C16—H16119.2
C2—C3—H3120.4N1—C17—C16120.9 (3)
C5—C4—C3121.6 (2)N1—C17—H17119.6
C5—C4—Br1119.60 (18)C16—C17—H17119.6
C3—C4—Br1118.79 (19)N1—C18—C19121.8 (2)
C4—C5—C6119.1 (2)N1—C18—H18119.1
C4—C5—H5120.5C19—C18—H18119.1
C6—C5—H5120.5C18—C19—C15120.3 (2)
C1—C6—C5120.0 (2)C18—C19—H19119.8
C1—C6—H6120.0C15—C19—H19119.8
C5—C6—H6120.0N1—C20—H20A109.5
C12—C7—C8121.3 (2)N1—C20—H20B109.5
C12—C7—H7119.4H20A—C20—H20B109.5
C8—C7—H7119.4N1—C20—H20C109.5
C9—C8—C7120.2 (2)H20A—C20—H20C109.5
C9—C8—H8119.9H20B—C20—H20C109.5
C7—C8—H8119.9O5—C21—H21D109.5
O4—C9—C8123.8 (2)O5—C21—H21A109.5
O4—C9—C10116.8 (2)H21D—C21—H21A109.5
C8—C9—C10119.4 (2)O5—C21—H21B109.5
O5—C10—C11125.7 (2)H21D—C21—H21B109.5
O5—C10—C9114.4 (2)H21A—C21—H21B109.5
O2—S1—C1—C6141.4 (2)O4—C9—C10—C11179.5 (2)
O1—S1—C1—C621.0 (2)C8—C9—C10—C110.3 (4)
O3—S1—C1—C695.5 (3)O5—C10—C11—C12179.1 (3)
O2—S1—C1—C239.2 (3)C9—C10—C11—C120.5 (4)
O1—S1—C1—C2159.6 (2)C8—C7—C12—C110.1 (4)
O3—S1—C1—C283.9 (3)C8—C7—C12—C13178.4 (3)
C6—C1—C2—C30.6 (4)C10—C11—C12—C70.6 (4)
S1—C1—C2—C3179.93 (18)C10—C11—C12—C13179.0 (3)
C1—C2—C3—C40.2 (4)C7—C12—C13—C14179.9 (3)
C2—C3—C4—C50.0 (4)C11—C12—C13—C141.8 (5)
C2—C3—C4—Br1179.37 (18)C12—C13—C14—C15178.9 (3)
C3—C4—C5—C60.1 (4)C13—C14—C15—C16174.7 (3)
Br1—C4—C5—C6179.49 (18)C13—C14—C15—C195.5 (5)
C2—C1—C6—C50.7 (4)C19—C15—C16—C170.6 (4)
S1—C1—C6—C5179.96 (19)C14—C15—C16—C17179.3 (3)
C4—C5—C6—C10.4 (4)C18—N1—C17—C160.5 (5)
C12—C7—C8—C90.9 (4)C20—N1—C17—C16179.6 (3)
C7—C8—C9—O4179.8 (3)C15—C16—C17—N10.1 (5)
C7—C8—C9—C101.0 (4)C17—N1—C18—C190.7 (4)
C21—O5—C10—C112.8 (4)C20—N1—C18—C19179.4 (3)
C21—O5—C10—C9175.9 (3)N1—C18—C19—C150.2 (5)
O4—C9—C10—O50.8 (4)C16—C15—C19—C180.4 (4)
C8—C9—C10—O5178.5 (3)C14—C15—C19—C18179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O3i0.821.782.578 (4)165
C2—H2···O2ii0.932.383.160 (4)141
C6—H6···O10.932.572.919 (4)103
C19—H19···O1iii0.932.383.269 (4)160
C20—H20B···O3iv0.962.533.394 (5)150
C20—H20C···O4v0.962.453.383 (4)164
C16—H16···Cg1vi0.932.583.465 (3)160
C21—H21D···Cg1vii0.962.843.627 (3)140
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z; (iii) x, y, z+1; (iv) x, y1, z+1; (v) x+1, y, z+1; (vi) x+1, y, z+1; (vii) x1, y1, z.
 

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