Buy article online - an online subscription or single-article purchase is required to access this article.
In the title compound, C
15H
16NO
2+·C
6H
4BrSO
3−, 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
CCDC reference: 271835
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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+·C6H4BrO3S− | Z = 2 |
Mr = 478.35 | F(000) = 488 |
Triclinic, P1 | Dx = 1.583 Mg m−3 |
Hall symbol: -P 1 | Melting point: 515-516 K K |
a = 9.9319 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3666 (8) Å | Cell parameters from 4970 reflections |
c = 10.5606 (8) Å | θ = 2.1–28.3° |
α = 109.71 (1)° | µ = 2.19 mm−1 |
β = 94.138 (1)° | T = 293 K |
γ = 98.458 (1)° | Plate, pale yellow |
V = 1003.79 (15) Å3 | 0.47 × 0.24 × 0.21 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 4970 independent reflections |
Radiation source: fine-focus sealed tube | 3596 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.1° |
ω scan | h = −12→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→13 |
Tmin = 0.543, Tmax = 0.638 | l = −14→13 |
6754 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-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 parameters | Δρmax = 0.70 e Å−3 |
12 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 | |
Br1 | 1.01679 (3) | 0.42000 (3) | 0.29816 (3) | 0.04784 (11) | |
S1 | 0.38479 (6) | 0.48268 (7) | 0.24218 (7) | 0.04138 (16) | |
O1 | 0.3131 (2) | 0.3946 (2) | 0.3039 (2) | 0.0563 (5) | |
O2 | 0.3413 (2) | 0.4401 (4) | 0.1008 (3) | 0.1080 (12) | |
O3 | 0.3872 (3) | 0.6267 (2) | 0.3204 (4) | 0.1027 (11) | |
O4 | −0.2573 (2) | 0.1677 (2) | 0.6065 (2) | 0.0543 (5) | |
H4 | −0.2896 | 0.2374 | 0.6431 | 0.081* | |
O5 | −0.1747 (2) | −0.0686 (2) | 0.53882 (19) | 0.0554 (6) | |
N1 | 0.5043 (2) | −0.0693 (2) | 1.2192 (2) | 0.0420 (5) | |
C1 | 0.5595 (2) | 0.4651 (2) | 0.2588 (2) | 0.0325 (5) | |
C2 | 0.6454 (3) | 0.5013 (3) | 0.1733 (2) | 0.0363 (5) | |
H2 | 0.6113 | 0.5343 | 0.1081 | 0.044* | |
C3 | 0.7818 (3) | 0.4881 (3) | 0.1857 (2) | 0.0367 (5) | |
H3 | 0.8401 | 0.5118 | 0.1288 | 0.044* | |
C4 | 0.8304 (2) | 0.4393 (2) | 0.2835 (2) | 0.0346 (5) | |
C5 | 0.7464 (3) | 0.4037 (3) | 0.3691 (2) | 0.0380 (5) | |
H5 | 0.7808 | 0.3709 | 0.4343 | 0.046* | |
C6 | 0.6098 (3) | 0.4173 (3) | 0.3567 (2) | 0.0364 (5) | |
H6 | 0.5519 | 0.3941 | 0.4142 | 0.044* | |
C7 | −0.0017 (3) | 0.2406 (3) | 0.9005 (3) | 0.0431 (6) | |
H7 | 0.0353 | 0.3125 | 0.9815 | 0.052* | |
C8 | −0.1033 (3) | 0.2606 (3) | 0.8159 (3) | 0.0425 (6) | |
H8 | −0.1347 | 0.3448 | 0.8409 | 0.051* | |
C9 | −0.1580 (3) | 0.1562 (3) | 0.6949 (2) | 0.0382 (5) | |
C10 | −0.1112 (3) | 0.0283 (3) | 0.6590 (2) | 0.0385 (5) | |
C11 | −0.0117 (3) | 0.0093 (3) | 0.7443 (2) | 0.0399 (6) | |
H11 | 0.0183 | −0.0755 | 0.7205 | 0.048* | |
C12 | 0.0457 (3) | 0.1163 (3) | 0.8672 (2) | 0.0384 (5) | |
C13 | 0.1499 (3) | 0.0995 (3) | 0.9614 (3) | 0.0414 (6) | |
H13 | 0.1799 | 0.1751 | 1.0414 | 0.050* | |
C14 | 0.2066 (3) | −0.0117 (3) | 0.9456 (3) | 0.0423 (6) | |
H14 | 0.1781 | −0.0871 | 0.8652 | 0.051* | |
C15 | 0.3093 (3) | −0.0270 (3) | 1.0424 (2) | 0.0379 (5) | |
C16 | 0.3678 (3) | −0.1454 (3) | 1.0073 (3) | 0.0458 (6) | |
H16 | 0.3413 | −0.2133 | 0.9216 | 0.055* | |
C17 | 0.4634 (3) | −0.1650 (3) | 1.0950 (3) | 0.0486 (7) | |
H17 | 0.5006 | −0.2458 | 1.0683 | 0.058* | |
C18 | 0.4510 (3) | 0.0476 (3) | 1.2568 (3) | 0.0461 (6) | |
H18 | 0.4803 | 0.1142 | 1.3427 | 0.055* | |
C19 | 0.3550 (3) | 0.0713 (3) | 1.1725 (3) | 0.0448 (6) | |
H19 | 0.3197 | 0.1531 | 1.2015 | 0.054* | |
C20 | 0.6072 (3) | −0.0936 (4) | 1.3124 (3) | 0.0588 (8) | |
H20A | 0.6805 | −0.1276 | 1.2642 | 0.088* | |
H20B | 0.5648 | −0.1612 | 1.3479 | 0.088* | |
H20C | 0.6432 | −0.0078 | 1.3858 | 0.088* | |
C21 | −0.1394 (4) | −0.2034 (3) | 0.5003 (3) | 0.0662 (10) | |
H21D | −0.1928 | −0.2623 | 0.4156 | 0.099* | |
H21A | −0.1580 | −0.2428 | 0.5688 | 0.099* | |
H21B | −0.0435 | −0.1962 | 0.4904 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02899 (15) | 0.0620 (2) | 0.05246 (17) | 0.01567 (13) | 0.00234 (11) | 0.01766 (13) |
S1 | 0.0273 (3) | 0.0484 (4) | 0.0513 (4) | 0.0117 (3) | 0.0001 (3) | 0.0204 (3) |
O1 | 0.0336 (10) | 0.0673 (14) | 0.0798 (14) | 0.0180 (10) | 0.0168 (10) | 0.0355 (11) |
O2 | 0.0406 (13) | 0.229 (4) | 0.0666 (15) | 0.0135 (18) | −0.0052 (11) | 0.074 (2) |
O3 | 0.0467 (14) | 0.0444 (13) | 0.209 (3) | 0.0228 (12) | 0.0075 (17) | 0.0312 (17) |
O4 | 0.0581 (13) | 0.0480 (11) | 0.0535 (11) | 0.0277 (10) | −0.0119 (9) | 0.0101 (9) |
O5 | 0.0710 (14) | 0.0412 (10) | 0.0457 (10) | 0.0252 (10) | −0.0186 (9) | 0.0037 (8) |
N1 | 0.0386 (12) | 0.0427 (12) | 0.0442 (11) | 0.0024 (10) | −0.0100 (9) | 0.0199 (9) |
C1 | 0.0279 (12) | 0.0330 (12) | 0.0332 (11) | 0.0093 (10) | −0.0003 (9) | 0.0066 (9) |
C2 | 0.0371 (13) | 0.0365 (13) | 0.0374 (12) | 0.0110 (11) | 0.0019 (10) | 0.0144 (10) |
C3 | 0.0329 (13) | 0.0377 (13) | 0.0387 (12) | 0.0046 (11) | 0.0066 (10) | 0.0128 (10) |
C4 | 0.0255 (11) | 0.0345 (12) | 0.0380 (12) | 0.0081 (10) | −0.0012 (9) | 0.0053 (9) |
C5 | 0.0361 (13) | 0.0463 (14) | 0.0330 (11) | 0.0144 (12) | −0.0006 (9) | 0.0139 (10) |
C6 | 0.0320 (12) | 0.0438 (14) | 0.0338 (11) | 0.0083 (11) | 0.0049 (9) | 0.0134 (10) |
C7 | 0.0494 (16) | 0.0373 (13) | 0.0388 (12) | 0.0067 (12) | −0.0036 (11) | 0.0109 (10) |
C8 | 0.0489 (16) | 0.0345 (13) | 0.0452 (13) | 0.0145 (12) | 0.0028 (11) | 0.0134 (10) |
C9 | 0.0381 (14) | 0.0385 (13) | 0.0415 (12) | 0.0132 (11) | 0.0008 (10) | 0.0171 (10) |
C10 | 0.0413 (14) | 0.0362 (13) | 0.0363 (12) | 0.0116 (11) | −0.0014 (10) | 0.0099 (10) |
C11 | 0.0420 (14) | 0.0383 (13) | 0.0426 (13) | 0.0153 (12) | 0.0008 (11) | 0.0162 (10) |
C12 | 0.0354 (13) | 0.0422 (14) | 0.0393 (12) | 0.0057 (12) | −0.0013 (10) | 0.0185 (10) |
C13 | 0.0416 (15) | 0.0415 (14) | 0.0402 (12) | 0.0058 (12) | −0.0031 (11) | 0.0158 (11) |
C14 | 0.0427 (15) | 0.0405 (14) | 0.0409 (13) | 0.0054 (12) | −0.0048 (11) | 0.0140 (11) |
C15 | 0.0353 (13) | 0.0381 (13) | 0.0418 (13) | 0.0024 (11) | −0.0009 (10) | 0.0190 (10) |
C16 | 0.0484 (16) | 0.0381 (14) | 0.0440 (14) | 0.0068 (13) | −0.0126 (11) | 0.0097 (11) |
C17 | 0.0502 (17) | 0.0387 (14) | 0.0527 (15) | 0.0113 (13) | −0.0102 (12) | 0.0129 (12) |
C18 | 0.0516 (17) | 0.0438 (15) | 0.0368 (13) | 0.0028 (13) | −0.0028 (11) | 0.0104 (11) |
C19 | 0.0504 (16) | 0.0396 (14) | 0.0454 (14) | 0.0124 (13) | 0.0029 (12) | 0.0151 (11) |
C20 | 0.0508 (18) | 0.071 (2) | 0.0573 (17) | 0.0086 (16) | −0.0162 (14) | 0.0319 (15) |
C21 | 0.094 (3) | 0.0423 (16) | 0.0521 (17) | 0.0308 (17) | −0.0162 (16) | 0.0017 (13) |
Geometric parameters (Å, º) top
Br1—C4 | 1.892 (2) | C8—C9 | 1.376 (4) |
S1—O2 | 1.420 (3) | C8—H8 | 0.93 |
S1—O1 | 1.429 (2) | C9—C10 | 1.410 (3) |
S1—O3 | 1.438 (3) | C10—C11 | 1.368 (3) |
S1—C1 | 1.774 (2) | C11—C12 | 1.406 (4) |
O4—C9 | 1.354 (3) | C11—H11 | 0.93 |
O4—H4 | 0.82 | C12—C13 | 1.453 (3) |
O5—C10 | 1.363 (3) | C13—C14 | 1.322 (4) |
O5—C21 | 1.422 (3) | C13—H13 | 0.93 |
N1—C17 | 1.341 (3) | C14—C15 | 1.455 (3) |
N1—C18 | 1.343 (4) | C14—H14 | 0.93 |
N1—C20 | 1.474 (3) | C15—C16 | 1.385 (4) |
C1—C6 | 1.382 (3) | C15—C19 | 1.400 (4) |
C1—C2 | 1.388 (3) | C16—C17 | 1.362 (4) |
C2—C3 | 1.382 (3) | C16—H16 | 0.93 |
C2—H2 | 0.93 | C17—H17 | 0.93 |
C3—C4 | 1.382 (3) | C18—C19 | 1.361 (4) |
C3—H3 | 0.93 | C18—H18 | 0.93 |
C4—C5 | 1.375 (4) | C19—H19 | 0.93 |
C5—C6 | 1.386 (3) | C20—H20A | 0.96 |
C5—H5 | 0.93 | C20—H20B | 0.96 |
C6—H6 | 0.93 | C20—H20C | 0.96 |
C7—C12 | 1.380 (4) | C21—H21D | 0.96 |
C7—C8 | 1.384 (4) | C21—H21A | 0.96 |
C7—H7 | 0.93 | C21—H21B | 0.96 |
| | | |
O2—S1—O1 | 112.76 (17) | C11—C10—C9 | 119.8 (2) |
O2—S1—O3 | 116.3 (2) | C10—C11—C12 | 121.0 (2) |
O1—S1—O3 | 110.35 (18) | C10—C11—H11 | 119.5 |
O2—S1—C1 | 106.19 (14) | C12—C11—H11 | 119.5 |
O1—S1—C1 | 106.50 (12) | C7—C12—C11 | 118.3 (2) |
O3—S1—C1 | 103.78 (13) | C7—C12—C13 | 119.0 (2) |
C9—O4—H4 | 109.5 | C11—C12—C13 | 122.6 (2) |
C10—O5—C21 | 117.6 (2) | C14—C13—C12 | 127.0 (2) |
C17—N1—C18 | 119.3 (2) | C14—C13—H13 | 116.5 |
C17—N1—C20 | 119.7 (2) | C12—C13—H13 | 116.5 |
C18—N1—C20 | 121.0 (2) | C13—C14—C15 | 126.1 (2) |
C6—C1—C2 | 120.4 (2) | C13—C14—H14 | 117.0 |
C6—C1—S1 | 120.25 (19) | C15—C14—H14 | 117.0 |
C2—C1—S1 | 119.32 (18) | C16—C15—C19 | 116.0 (2) |
C3—C2—C1 | 119.7 (2) | C16—C15—C14 | 119.6 (2) |
C3—C2—H2 | 120.2 | C19—C15—C14 | 124.4 (2) |
C1—C2—H2 | 120.2 | C17—C16—C15 | 121.7 (2) |
C4—C3—C2 | 119.2 (2) | C17—C16—H16 | 119.2 |
C4—C3—H3 | 120.4 | C15—C16—H16 | 119.2 |
C2—C3—H3 | 120.4 | N1—C17—C16 | 120.9 (3) |
C5—C4—C3 | 121.6 (2) | N1—C17—H17 | 119.6 |
C5—C4—Br1 | 119.60 (18) | C16—C17—H17 | 119.6 |
C3—C4—Br1 | 118.79 (19) | N1—C18—C19 | 121.8 (2) |
C4—C5—C6 | 119.1 (2) | N1—C18—H18 | 119.1 |
C4—C5—H5 | 120.5 | C19—C18—H18 | 119.1 |
C6—C5—H5 | 120.5 | C18—C19—C15 | 120.3 (2) |
C1—C6—C5 | 120.0 (2) | C18—C19—H19 | 119.8 |
C1—C6—H6 | 120.0 | C15—C19—H19 | 119.8 |
C5—C6—H6 | 120.0 | N1—C20—H20A | 109.5 |
C12—C7—C8 | 121.3 (2) | N1—C20—H20B | 109.5 |
C12—C7—H7 | 119.4 | H20A—C20—H20B | 109.5 |
C8—C7—H7 | 119.4 | N1—C20—H20C | 109.5 |
C9—C8—C7 | 120.2 (2) | H20A—C20—H20C | 109.5 |
C9—C8—H8 | 119.9 | H20B—C20—H20C | 109.5 |
C7—C8—H8 | 119.9 | O5—C21—H21D | 109.5 |
O4—C9—C8 | 123.8 (2) | O5—C21—H21A | 109.5 |
O4—C9—C10 | 116.8 (2) | H21D—C21—H21A | 109.5 |
C8—C9—C10 | 119.4 (2) | O5—C21—H21B | 109.5 |
O5—C10—C11 | 125.7 (2) | H21D—C21—H21B | 109.5 |
O5—C10—C9 | 114.4 (2) | H21A—C21—H21B | 109.5 |
| | | |
O2—S1—C1—C6 | −141.4 (2) | O4—C9—C10—C11 | −179.5 (2) |
O1—S1—C1—C6 | −21.0 (2) | C8—C9—C10—C11 | −0.3 (4) |
O3—S1—C1—C6 | 95.5 (3) | O5—C10—C11—C12 | −179.1 (3) |
O2—S1—C1—C2 | 39.2 (3) | C9—C10—C11—C12 | −0.5 (4) |
O1—S1—C1—C2 | 159.6 (2) | C8—C7—C12—C11 | 0.1 (4) |
O3—S1—C1—C2 | −83.9 (3) | C8—C7—C12—C13 | −178.4 (3) |
C6—C1—C2—C3 | 0.6 (4) | C10—C11—C12—C7 | 0.6 (4) |
S1—C1—C2—C3 | 179.93 (18) | C10—C11—C12—C13 | 179.0 (3) |
C1—C2—C3—C4 | −0.2 (4) | C7—C12—C13—C14 | −179.9 (3) |
C2—C3—C4—C5 | 0.0 (4) | C11—C12—C13—C14 | 1.8 (5) |
C2—C3—C4—Br1 | 179.37 (18) | C12—C13—C14—C15 | −178.9 (3) |
C3—C4—C5—C6 | −0.1 (4) | C13—C14—C15—C16 | −174.7 (3) |
Br1—C4—C5—C6 | −179.49 (18) | C13—C14—C15—C19 | 5.5 (5) |
C2—C1—C6—C5 | −0.7 (4) | C19—C15—C16—C17 | 0.6 (4) |
S1—C1—C6—C5 | 179.96 (19) | C14—C15—C16—C17 | −179.3 (3) |
C4—C5—C6—C1 | 0.4 (4) | C18—N1—C17—C16 | −0.5 (5) |
C12—C7—C8—C9 | −0.9 (4) | C20—N1—C17—C16 | 179.6 (3) |
C7—C8—C9—O4 | −179.8 (3) | C15—C16—C17—N1 | −0.1 (5) |
C7—C8—C9—C10 | 1.0 (4) | C17—N1—C18—C19 | 0.7 (4) |
C21—O5—C10—C11 | 2.8 (4) | C20—N1—C18—C19 | −179.4 (3) |
C21—O5—C10—C9 | −175.9 (3) | N1—C18—C19—C15 | −0.2 (5) |
O4—C9—C10—O5 | −0.8 (4) | C16—C15—C19—C18 | −0.4 (4) |
C8—C9—C10—O5 | 178.5 (3) | C14—C15—C19—C18 | 179.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3i | 0.82 | 1.78 | 2.578 (4) | 165 |
C2—H2···O2ii | 0.93 | 2.38 | 3.160 (4) | 141 |
C6—H6···O1 | 0.93 | 2.57 | 2.919 (4) | 103 |
C19—H19···O1iii | 0.93 | 2.38 | 3.269 (4) | 160 |
C20—H20B···O3iv | 0.96 | 2.53 | 3.394 (5) | 150 |
C20—H20C···O4v | 0.96 | 2.45 | 3.383 (4) | 164 |
C16—H16···Cg1vi | 0.93 | 2.58 | 3.465 (3) | 160 |
C21—H21D···Cg1vii | 0.96 | 2.84 | 3.627 (3) | 140 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x, y, z+1; (iv) x, y−1, z+1; (v) x+1, y, z+1; (vi) −x+1, −y, −z+1; (vii) x−1, y−1, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.