The title compound, C
15H
16NO
2+·C
6H
4ClO
3S
−, is isomorphous with the 4-bromobenzenesulfonate derivative. The cation is almost planar and the benzene ring of the anion makes dihedral angles of 82.79 (1) and 76.39 (1)° with the mean planes through the benzene ring of the cation and the pyridinium ring, respectively. 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
CCDC reference: 277795
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - O2 .. 7.03 su
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for S1
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O3 .. 5.61 su
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O3 .. 3.02 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C15 H16 N O2
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
1 ALERT type 4 Improvement, methodology, query or suggestion
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-chlorobenzenesulfonate
top
Crystal data top
C15H16NO2+·C6H4ClO3S− | Z = 2 |
Mr = 433.89 | F(000) = 452 |
Triclinic, P1 | Dx = 1.445 Mg m−3 |
Hall symbol: -P 1 | Melting point: 505-506 K K |
a = 9.8153 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4218 (17) Å | Cell parameters from 9566 reflections |
c = 10.5894 (17) Å | θ = 2.1–25.0° |
α = 110.538 (2)° | µ = 0.33 mm−1 |
β = 93.864 (2)° | T = 293 K |
γ = 97.819 (2)° | Needle, red |
V = 997.2 (3) Å3 | 0.50 × 0.27 × 0.19 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3517 independent reflections |
Radiation source: fine-focus sealed tube | 3150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.899, Tmax = 0.939 | l = −12→12 |
9566 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0676P)2 + 0.5159P] where P = (Fo2 + 2Fc2)/3 |
3517 reflections | (Δ/σ)max = 0.001 |
265 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | Uiso*/Ueq | |
Cl1 | 1.01184 (6) | 0.92106 (7) | 0.79894 (7) | 0.0642 (2) | |
S1 | 0.38749 (5) | 0.98497 (6) | 0.74329 (6) | 0.04639 (18) | |
O1 | 0.3453 (2) | 0.9460 (4) | 0.6029 (2) | 0.1169 (11) | |
O2 | 0.3881 (2) | 1.1280 (2) | 0.8265 (3) | 0.1037 (9) | |
O3 | 0.31413 (17) | 0.89487 (19) | 0.8011 (2) | 0.0650 (5) | |
O4 | 0.25389 (18) | 1.33328 (17) | 0.89172 (17) | 0.0600 (5) | |
H4A | 0.2811 | 1.2589 | 0.8588 | 0.090* | |
O5 | 0.16998 (19) | 1.57044 (16) | 0.95645 (16) | 0.0606 (5) | |
N1 | −0.50959 (18) | 1.57119 (18) | 0.27730 (18) | 0.0459 (4) | |
C1 | 0.5645 (2) | 0.9657 (2) | 0.7596 (2) | 0.0388 (4) | |
C2 | 0.6521 (2) | 1.0008 (2) | 0.6749 (2) | 0.0426 (5) | |
H2B | 0.6181 | 1.0336 | 0.6101 | 0.051* | |
C3 | 0.7895 (2) | 0.9871 (2) | 0.6870 (2) | 0.0447 (5) | |
H3B | 0.8486 | 1.0098 | 0.6301 | 0.054* | |
C4 | 0.8385 (2) | 0.9389 (2) | 0.7848 (2) | 0.0442 (5) | |
C5 | 0.7530 (2) | 0.9050 (2) | 0.8705 (2) | 0.0465 (5) | |
H5A | 0.7877 | 0.8737 | 0.9362 | 0.056* | |
C6 | 0.6151 (2) | 0.9182 (2) | 0.8577 (2) | 0.0431 (5) | |
H6A | 0.5562 | 0.8952 | 0.9146 | 0.052* | |
C7 | −0.0010 (2) | 1.2561 (2) | 0.5945 (2) | 0.0477 (5) | |
H7A | −0.0374 | 1.1834 | 0.5136 | 0.057* | |
C8 | 0.1005 (2) | 1.2373 (2) | 0.6810 (2) | 0.0472 (5) | |
H8A | 0.1323 | 1.1529 | 0.6573 | 0.057* | |
C9 | 0.1544 (2) | 1.3437 (2) | 0.8019 (2) | 0.0427 (5) | |
C10 | 0.1078 (2) | 1.4719 (2) | 0.8364 (2) | 0.0430 (5) | |
C11 | 0.0075 (2) | 1.4900 (2) | 0.7500 (2) | 0.0441 (5) | |
H11A | −0.0233 | 1.5749 | 0.7732 | 0.053* | |
C12 | −0.0493 (2) | 1.3813 (2) | 0.6268 (2) | 0.0427 (5) | |
C13 | −0.1542 (2) | 1.3972 (2) | 0.5319 (2) | 0.0462 (5) | |
H13A | −0.1843 | 1.3212 | 0.4519 | 0.055* | |
C14 | −0.2111 (2) | 1.5097 (2) | 0.5485 (2) | 0.0466 (5) | |
H14A | −0.1827 | 1.5852 | 0.6294 | 0.056* | |
C15 | −0.3140 (2) | 1.5259 (2) | 0.4519 (2) | 0.0422 (5) | |
C16 | −0.3708 (2) | 1.6470 (2) | 0.4881 (2) | 0.0504 (5) | |
H16A | −0.3427 | 1.7155 | 0.5736 | 0.061* | |
C17 | −0.4668 (3) | 1.6676 (2) | 0.4010 (2) | 0.0529 (6) | |
H17A | −0.5029 | 1.7498 | 0.4279 | 0.064* | |
C18 | −0.4579 (2) | 1.4521 (2) | 0.2386 (2) | 0.0508 (5) | |
H18A | −0.4884 | 1.3853 | 0.1526 | 0.061* | |
C19 | −0.3618 (2) | 1.4269 (2) | 0.3222 (2) | 0.0496 (5) | |
H19A | −0.3280 | 1.3435 | 0.2930 | 0.059* | |
C20 | −0.6133 (3) | 1.5962 (3) | 0.1844 (3) | 0.0628 (7) | |
H20A | −0.6870 | 1.6323 | 0.2333 | 0.094* | |
H20B | −0.6501 | 1.5103 | 0.1110 | 0.094* | |
H20C | −0.5700 | 1.6621 | 0.1486 | 0.094* | |
C21 | 0.1333 (3) | 1.7053 (3) | 0.9938 (3) | 0.0709 (8) | |
H21A | 0.1833 | 1.7641 | 1.0805 | 0.106* | |
H21B | 0.0356 | 1.6984 | 0.9995 | 0.106* | |
H21C | 0.1564 | 1.7443 | 0.9267 | 0.106* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0377 (3) | 0.0845 (5) | 0.0712 (4) | 0.0219 (3) | 0.0015 (3) | 0.0262 (3) |
S1 | 0.0346 (3) | 0.0518 (3) | 0.0554 (3) | 0.0149 (2) | −0.0010 (2) | 0.0212 (3) |
O1 | 0.0494 (12) | 0.242 (3) | 0.0762 (14) | 0.0201 (16) | −0.0053 (10) | 0.0834 (19) |
O2 | 0.0541 (12) | 0.0523 (11) | 0.196 (3) | 0.0252 (9) | 0.0002 (14) | 0.0317 (14) |
O3 | 0.0414 (9) | 0.0735 (11) | 0.0913 (13) | 0.0198 (8) | 0.0162 (9) | 0.0388 (10) |
O4 | 0.0649 (11) | 0.0528 (10) | 0.0593 (10) | 0.0304 (8) | −0.0143 (8) | 0.0134 (8) |
O5 | 0.0765 (11) | 0.0474 (9) | 0.0501 (9) | 0.0297 (8) | −0.0184 (8) | 0.0061 (7) |
N1 | 0.0419 (10) | 0.0483 (10) | 0.0489 (10) | 0.0052 (8) | −0.0078 (8) | 0.0226 (8) |
C1 | 0.0375 (10) | 0.0365 (10) | 0.0398 (10) | 0.0121 (8) | −0.0007 (8) | 0.0098 (8) |
C2 | 0.0463 (12) | 0.0396 (10) | 0.0431 (11) | 0.0118 (9) | −0.0002 (9) | 0.0159 (9) |
C3 | 0.0417 (11) | 0.0450 (11) | 0.0470 (12) | 0.0081 (9) | 0.0075 (9) | 0.0156 (9) |
C4 | 0.0356 (11) | 0.0445 (11) | 0.0463 (11) | 0.0121 (9) | −0.0015 (9) | 0.0084 (9) |
C5 | 0.0451 (12) | 0.0546 (13) | 0.0414 (11) | 0.0164 (10) | −0.0028 (9) | 0.0178 (10) |
C6 | 0.0411 (11) | 0.0502 (12) | 0.0397 (11) | 0.0135 (9) | 0.0037 (8) | 0.0164 (9) |
C7 | 0.0514 (13) | 0.0413 (11) | 0.0471 (12) | 0.0085 (9) | −0.0018 (10) | 0.0132 (9) |
C8 | 0.0521 (13) | 0.0383 (11) | 0.0526 (12) | 0.0144 (9) | 0.0014 (10) | 0.0166 (9) |
C9 | 0.0414 (11) | 0.0431 (11) | 0.0472 (11) | 0.0146 (9) | −0.0001 (9) | 0.0193 (9) |
C10 | 0.0447 (11) | 0.0426 (11) | 0.0413 (11) | 0.0143 (9) | −0.0015 (9) | 0.0136 (9) |
C11 | 0.0455 (12) | 0.0431 (11) | 0.0476 (12) | 0.0181 (9) | 0.0005 (9) | 0.0183 (9) |
C12 | 0.0397 (11) | 0.0461 (11) | 0.0445 (11) | 0.0076 (9) | −0.0005 (9) | 0.0199 (9) |
C13 | 0.0461 (12) | 0.0468 (12) | 0.0460 (11) | 0.0078 (9) | −0.0024 (9) | 0.0190 (9) |
C14 | 0.0476 (12) | 0.0463 (12) | 0.0443 (11) | 0.0076 (10) | −0.0048 (9) | 0.0166 (9) |
C15 | 0.0397 (11) | 0.0432 (11) | 0.0455 (11) | 0.0055 (9) | −0.0007 (9) | 0.0199 (9) |
C16 | 0.0534 (13) | 0.0416 (11) | 0.0496 (12) | 0.0090 (10) | −0.0109 (10) | 0.0112 (10) |
C17 | 0.0550 (13) | 0.0440 (12) | 0.0581 (14) | 0.0148 (10) | −0.0098 (11) | 0.0173 (10) |
C18 | 0.0568 (14) | 0.0479 (12) | 0.0422 (12) | 0.0048 (10) | −0.0051 (10) | 0.0132 (10) |
C19 | 0.0539 (13) | 0.0445 (12) | 0.0515 (13) | 0.0147 (10) | 0.0005 (10) | 0.0178 (10) |
C20 | 0.0564 (15) | 0.0747 (17) | 0.0615 (15) | 0.0101 (12) | −0.0165 (12) | 0.0345 (13) |
C21 | 0.096 (2) | 0.0458 (13) | 0.0588 (15) | 0.0311 (14) | −0.0164 (14) | 0.0024 (11) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.738 (2) | C8—C9 | 1.379 (3) |
S1—O1 | 1.413 (2) | C8—H8A | 0.9300 |
S1—O3 | 1.4334 (19) | C9—C10 | 1.405 (3) |
S1—O2 | 1.440 (2) | C10—C11 | 1.375 (3) |
S1—C1 | 1.780 (2) | C11—C12 | 1.410 (3) |
O4—C9 | 1.358 (2) | C11—H11A | 0.9300 |
O4—H4A | 0.8200 | C12—C13 | 1.457 (3) |
O5—C10 | 1.361 (3) | C13—C14 | 1.328 (3) |
O5—C21 | 1.424 (3) | C13—H13A | 0.9300 |
N1—C17 | 1.337 (3) | C14—C15 | 1.457 (3) |
N1—C18 | 1.344 (3) | C14—H14A | 0.9300 |
N1—C20 | 1.479 (3) | C15—C16 | 1.389 (3) |
C1—C2 | 1.387 (3) | C15—C19 | 1.399 (3) |
C1—C6 | 1.389 (3) | C16—C17 | 1.365 (3) |
C2—C3 | 1.377 (3) | C16—H16A | 0.9300 |
C2—H2B | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.386 (3) | C18—C19 | 1.365 (3) |
C3—H3B | 0.9300 | C18—H18A | 0.9300 |
C4—C5 | 1.378 (3) | C19—H19A | 0.9300 |
C5—C6 | 1.381 (3) | C20—H20A | 0.9600 |
C5—H5A | 0.9300 | C20—H20B | 0.9600 |
C6—H6A | 0.9300 | C20—H20C | 0.9600 |
C7—C12 | 1.387 (3) | C21—H21A | 0.9600 |
C7—C8 | 1.388 (3) | C21—H21B | 0.9600 |
C7—H7A | 0.9300 | C21—H21C | 0.9600 |
| | | |
O1—S1—O3 | 112.70 (15) | C11—C10—C9 | 119.80 (19) |
O1—S1—O2 | 116.47 (18) | C10—C11—C12 | 120.81 (19) |
O3—S1—O2 | 109.96 (14) | C10—C11—H11A | 119.6 |
O1—S1—C1 | 106.42 (12) | C12—C11—H11A | 119.6 |
O3—S1—C1 | 106.36 (10) | C7—C12—C11 | 118.40 (19) |
O2—S1—C1 | 103.99 (11) | C7—C12—C13 | 119.20 (19) |
C9—O4—H4A | 109.5 | C11—C12—C13 | 122.39 (19) |
C10—O5—C21 | 117.87 (17) | C14—C13—C12 | 126.3 (2) |
C17—N1—C18 | 119.61 (18) | C14—C13—H13A | 116.8 |
C17—N1—C20 | 119.8 (2) | C12—C13—H13A | 116.8 |
C18—N1—C20 | 120.55 (19) | C13—C14—C15 | 126.1 (2) |
C2—C1—C6 | 120.24 (19) | C13—C14—H14A | 117.0 |
C2—C1—S1 | 119.45 (15) | C15—C14—H14A | 117.0 |
C6—C1—S1 | 120.30 (16) | C16—C15—C19 | 116.18 (19) |
C3—C2—C1 | 120.02 (19) | C16—C15—C14 | 119.18 (19) |
C3—C2—H2B | 120.0 | C19—C15—C14 | 124.65 (19) |
C1—C2—H2B | 120.0 | C17—C16—C15 | 121.5 (2) |
C2—C3—C4 | 119.2 (2) | C17—C16—H16A | 119.3 |
C2—C3—H3B | 120.4 | C15—C16—H16A | 119.3 |
C4—C3—H3B | 120.4 | N1—C17—C16 | 120.8 (2) |
C5—C4—C3 | 121.46 (19) | N1—C17—H17A | 119.6 |
C5—C4—Cl1 | 119.62 (17) | C16—C17—H17A | 119.6 |
C3—C4—Cl1 | 118.92 (17) | N1—C18—C19 | 121.6 (2) |
C4—C5—C6 | 119.2 (2) | N1—C18—H18A | 119.2 |
C4—C5—H5A | 120.4 | C19—C18—H18A | 119.2 |
C6—C5—H5A | 120.4 | C18—C19—C15 | 120.3 (2) |
C5—C6—C1 | 119.9 (2) | C18—C19—H19A | 119.9 |
C5—C6—H6A | 120.1 | C15—C19—H19A | 119.9 |
C1—C6—H6A | 120.1 | N1—C20—H20A | 109.5 |
C12—C7—C8 | 121.1 (2) | N1—C20—H20B | 109.5 |
C12—C7—H7A | 119.5 | H20A—C20—H20B | 109.5 |
C8—C7—H7A | 119.5 | N1—C20—H20C | 109.5 |
C9—C8—C7 | 120.11 (19) | H20A—C20—H20C | 109.5 |
C9—C8—H8A | 119.9 | H20B—C20—H20C | 109.5 |
C7—C8—H8A | 119.9 | O5—C21—H21A | 109.5 |
O4—C9—C8 | 123.57 (18) | O5—C21—H21B | 109.5 |
O4—C9—C10 | 116.63 (18) | H21A—C21—H21B | 109.5 |
C8—C9—C10 | 119.79 (19) | O5—C21—H21C | 109.5 |
O5—C10—C11 | 125.26 (19) | H21A—C21—H21C | 109.5 |
O5—C10—C9 | 114.94 (18) | H21B—C21—H21C | 109.5 |
| | | |
O1—S1—C1—C2 | 37.9 (2) | O4—C9—C10—C11 | 179.8 (2) |
O3—S1—C1—C2 | 158.24 (17) | C8—C9—C10—C11 | 0.8 (3) |
O2—S1—C1—C2 | −85.7 (2) | O5—C10—C11—C12 | 179.2 (2) |
O1—S1—C1—C6 | −143.2 (2) | C9—C10—C11—C12 | −0.1 (3) |
O3—S1—C1—C6 | −22.8 (2) | C8—C7—C12—C11 | 0.1 (3) |
O2—S1—C1—C6 | 93.3 (2) | C8—C7—C12—C13 | 178.9 (2) |
C6—C1—C2—C3 | 0.7 (3) | C10—C11—C12—C7 | −0.3 (3) |
S1—C1—C2—C3 | 179.66 (15) | C10—C11—C12—C13 | −179.1 (2) |
C1—C2—C3—C4 | −0.4 (3) | C7—C12—C13—C14 | 179.6 (2) |
C2—C3—C4—C5 | −0.2 (3) | C11—C12—C13—C14 | −1.7 (4) |
C2—C3—C4—Cl1 | 179.70 (16) | C12—C13—C14—C15 | 178.6 (2) |
C3—C4—C5—C6 | 0.6 (3) | C13—C14—C15—C16 | 175.6 (2) |
Cl1—C4—C5—C6 | −179.34 (16) | C13—C14—C15—C19 | −4.3 (4) |
C4—C5—C6—C1 | −0.3 (3) | C19—C15—C16—C17 | −0.6 (3) |
C2—C1—C6—C5 | −0.3 (3) | C14—C15—C16—C17 | 179.6 (2) |
S1—C1—C6—C5 | −179.28 (16) | C18—N1—C17—C16 | 0.3 (4) |
C12—C7—C8—C9 | 0.6 (4) | C20—N1—C17—C16 | −179.7 (2) |
C7—C8—C9—O4 | −180.0 (2) | C15—C16—C17—N1 | 0.1 (4) |
C7—C8—C9—C10 | −1.0 (3) | C17—N1—C18—C19 | −0.3 (3) |
C21—O5—C10—C11 | −2.9 (4) | C20—N1—C18—C19 | 179.8 (2) |
C21—O5—C10—C9 | 176.5 (2) | N1—C18—C19—C15 | −0.2 (4) |
O4—C9—C10—O5 | 0.4 (3) | C16—C15—C19—C18 | 0.6 (3) |
C8—C9—C10—O5 | −178.6 (2) | C14—C15—C19—C18 | −179.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O2 | 0.82 | 1.79 | 2.577 (4) | 161 |
C2—H2B···O1i | 0.93 | 2.38 | 3.180 (3) | 144 |
C6—H6A···O3 | 0.93 | 2.59 | 2.934 (3) | 103 |
C19—H19A···O3ii | 0.93 | 2.36 | 3.257 (3) | 163 |
C20—H20B···O4iii | 0.96 | 2.43 | 3.367 (4) | 165 |
C20—H20C···O2iv | 0.96 | 2.55 | 3.420 (4) | 151 |
C16—H16A···Cg1v | 0.93 | 2.58 | 3.476 (2) | 162 |
C21—H21A···Cg1vi | 0.96 | 2.84 | 3.626 (3) | 140 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y, z−1; (iv) −x, −y+3, −z+1; (v) x−1, y+1, z; (vi) −x+1, −y+3, −z+2. |