organic compounds
1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate
aDepartment of Physics, Presidency College, Chennai 600 005, India, bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and cDepartment of physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, mohan66@hotmail.com
In the title salt, C15H16N+·C7H7O3S−, the dihedral angle between the pyridine and benzene rings of the cation is 5.98 (18)°. In the crystal, adjacent anions and cations are linked by weak non-classical C—H⋯O hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.749 (2) Å.
Related literature
For molecular compounds with non-linear optical properties, see: Bosshard et al. (1995); Nalwa & Miyata (1997). For related structures, see: Murugavel et al. (2009); Sivakumar et al. (2012); Okada et al. (1990).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812044509/rk2384sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044509/rk2384Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044509/rk2384Isup3.cml
The title compound was synthesized by the condensation of 4-methyl-N-methyl pyridinium tosylate, which was prepared from 4-picoline (4.65 g, 5 mmol) and methyl p-toluenesulfonate (9.31 g, 5 mmol), and 4-methylbenzaldehyde (6 g, 5 mmol) in the presence of piperidine. The single crystals were grown by slow evaporation method in room temperature.
The H atoms were positioned geometrically and refined using riding model with C–H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic H, C–H = 0.96Å and Uiso(H) = 1.5Ueq(C) for methyl H. The components of the anisotropic displacement parameters for C7 and C8 were restrained to be equal within an effective deviation of 0.001 using DELU instruction in SHELXL (Sheldrick, 2008).
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C15H16N+·C7H7O3S− | F(000) = 808 |
Mr = 381.48 | Dx = 1.278 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4112 reflections |
a = 9.1380 (6) Å | θ = 2.2–28.4° |
b = 6.4257 (5) Å | µ = 0.19 mm−1 |
c = 33.884 (2) Å | T = 295 K |
β = 95.004 (4)° | Block, colourless |
V = 1982.0 (2) Å3 | 0.28 × 0.22 × 0.20 mm |
Z = 4 |
Bruker Kappa APEXII diffractometer | 4902 independent reflections |
Radiation source: fine-focus sealed tube | 3850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω– and ϕ–scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.950, Tmax = 0.964 | k = −8→8 |
18512 measured reflections | l = −44→45 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0478P)2 + 2.5149P] where P = (Fo2 + 2Fc2)/3 |
4902 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.57 e Å−3 |
1 restraint | Δρmin = −0.37 e Å−3 |
C15H16N+·C7H7O3S− | V = 1982.0 (2) Å3 |
Mr = 381.48 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.1380 (6) Å | µ = 0.19 mm−1 |
b = 6.4257 (5) Å | T = 295 K |
c = 33.884 (2) Å | 0.28 × 0.22 × 0.20 mm |
β = 95.004 (4)° |
Bruker Kappa APEXII diffractometer | 4902 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3850 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.964 | Rint = 0.031 |
18512 measured reflections |
R[F2 > 2σ(F2)] = 0.075 | 1 restraint |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.57 e Å−3 |
4902 reflections | Δρmin = −0.37 e Å−3 |
247 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8177 (3) | 0.1727 (5) | 0.32460 (9) | 0.0480 (7) | |
C2 | 0.9323 (3) | 0.0485 (6) | 0.31430 (10) | 0.0586 (9) | |
H2 | 1.0286 | 0.0873 | 0.3219 | 0.070* | |
C3 | 0.9059 (3) | −0.1293 (6) | 0.29319 (10) | 0.0557 (8) | |
H3 | 0.9848 | −0.2100 | 0.2867 | 0.067* | |
C4 | 0.6546 (3) | −0.0742 (5) | 0.29074 (9) | 0.0519 (7) | |
H4 | 0.5595 | −0.1168 | 0.2826 | 0.062* | |
C5 | 0.6764 (3) | 0.1060 (5) | 0.31182 (10) | 0.0535 (8) | |
H5 | 0.5959 | 0.1851 | 0.3177 | 0.064* | |
C6 | 0.8525 (4) | 0.3602 (6) | 0.34869 (10) | 0.0581 (8) | |
H6 | 0.9514 | 0.3895 | 0.3552 | 0.070* | |
C7 | 0.7580 (4) | 0.4879 (6) | 0.36164 (10) | 0.0562 (8) | |
H7 | 0.6593 | 0.4607 | 0.3545 | 0.067* | |
C8 | 0.7923 (4) | 0.6722 (5) | 0.38662 (9) | 0.0511 (7) | |
C9 | 0.6807 (4) | 0.8026 (7) | 0.39551 (11) | 0.0687 (10) | |
H9 | 0.5849 | 0.7725 | 0.3856 | 0.082* | |
C10 | 0.7073 (5) | 0.9779 (7) | 0.41889 (13) | 0.0780 (12) | |
H10 | 0.6288 | 1.0626 | 0.4242 | 0.094* | |
C11 | 0.8446 (5) | 1.0290 (6) | 0.43424 (10) | 0.0666 (10) | |
C12 | 0.9570 (5) | 0.8987 (8) | 0.42589 (13) | 0.0834 (13) | |
H12 | 1.0523 | 0.9282 | 0.4363 | 0.100* | |
C13 | 0.9312 (4) | 0.7257 (7) | 0.40249 (13) | 0.0757 (11) | |
H13 | 1.0101 | 0.6419 | 0.3972 | 0.091* | |
C14 | 0.7436 (4) | −0.3798 (5) | 0.25756 (10) | 0.0623 (9) | |
H14A | 0.7213 | −0.3417 | 0.2303 | 0.093* | |
H14B | 0.6626 | −0.4558 | 0.2666 | 0.093* | |
H14C | 0.8301 | −0.4652 | 0.2600 | 0.093* | |
C15 | 0.8745 (7) | 1.2200 (7) | 0.45951 (14) | 0.1050 (18) | |
H15A | 0.7848 | 1.2962 | 0.4611 | 0.157* | |
H15B | 0.9449 | 1.3065 | 0.4479 | 0.157* | |
H15C | 0.9127 | 1.1789 | 0.4856 | 0.157* | |
C16 | 0.3056 (3) | 0.4990 (4) | 0.36655 (8) | 0.0397 (6) | |
C17 | 0.3040 (4) | 0.6399 (5) | 0.39722 (10) | 0.0530 (8) | |
H17 | 0.2963 | 0.7815 | 0.3917 | 0.064* | |
C18 | 0.3140 (4) | 0.5713 (6) | 0.43625 (10) | 0.0669 (10) | |
H18 | 0.3134 | 0.6685 | 0.4566 | 0.080* | |
C19 | 0.3247 (4) | 0.3641 (6) | 0.44559 (11) | 0.0619 (9) | |
C20 | 0.3257 (5) | 0.2259 (6) | 0.41467 (12) | 0.0685 (10) | |
H20 | 0.3332 | 0.0845 | 0.4203 | 0.082* | |
C21 | 0.3159 (4) | 0.2887 (5) | 0.37551 (11) | 0.0587 (8) | |
H21 | 0.3163 | 0.1907 | 0.3553 | 0.070* | |
C22 | 0.3344 (6) | 0.2865 (9) | 0.48800 (12) | 0.0999 (16) | |
H22A | 0.2391 | 0.2933 | 0.4978 | 0.150* | |
H22B | 0.4019 | 0.3719 | 0.5041 | 0.150* | |
H22C | 0.3684 | 0.1450 | 0.4889 | 0.150* | |
N1 | 0.7693 (3) | −0.1908 (4) | 0.28160 (7) | 0.0447 (6) | |
O1 | 0.4209 (2) | 0.5016 (4) | 0.30040 (7) | 0.0603 (6) | |
O2 | 0.1565 (2) | 0.5055 (4) | 0.29878 (7) | 0.0611 (6) | |
O3 | 0.2956 (3) | 0.8137 (4) | 0.31892 (8) | 0.0753 (8) | |
S1 | 0.29376 (8) | 0.58894 (12) | 0.31685 (2) | 0.0444 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0485 (16) | 0.0467 (17) | 0.0488 (16) | −0.0024 (13) | 0.0038 (13) | 0.0100 (13) |
C2 | 0.0406 (15) | 0.070 (2) | 0.065 (2) | −0.0036 (15) | 0.0044 (14) | 0.0021 (18) |
C3 | 0.0442 (16) | 0.058 (2) | 0.066 (2) | 0.0095 (15) | 0.0092 (14) | 0.0037 (16) |
C4 | 0.0411 (15) | 0.0583 (19) | 0.0555 (17) | 0.0006 (14) | −0.0001 (13) | 0.0049 (16) |
C5 | 0.0463 (16) | 0.0573 (19) | 0.0573 (17) | 0.0138 (15) | 0.0063 (13) | 0.0017 (16) |
C6 | 0.0443 (16) | 0.063 (2) | 0.067 (2) | −0.0036 (15) | 0.0009 (15) | 0.0071 (17) |
C7 | 0.0491 (17) | 0.0618 (19) | 0.0572 (18) | −0.0059 (15) | 0.0013 (14) | 0.0045 (14) |
C8 | 0.0536 (17) | 0.0527 (17) | 0.0471 (15) | −0.0037 (14) | 0.0054 (13) | 0.0111 (12) |
C9 | 0.0517 (19) | 0.081 (3) | 0.073 (2) | −0.0037 (19) | 0.0066 (17) | −0.006 (2) |
C10 | 0.077 (3) | 0.083 (3) | 0.077 (3) | 0.018 (2) | 0.017 (2) | −0.007 (2) |
C11 | 0.098 (3) | 0.056 (2) | 0.0452 (17) | −0.007 (2) | 0.0031 (18) | −0.0002 (16) |
C12 | 0.064 (2) | 0.094 (3) | 0.090 (3) | −0.015 (2) | −0.007 (2) | −0.023 (3) |
C13 | 0.055 (2) | 0.077 (3) | 0.094 (3) | 0.0079 (19) | −0.0004 (19) | −0.020 (2) |
C14 | 0.086 (3) | 0.0438 (18) | 0.0580 (19) | 0.0003 (17) | 0.0103 (17) | 0.0020 (15) |
C15 | 0.172 (5) | 0.071 (3) | 0.070 (3) | −0.007 (3) | 0.004 (3) | −0.016 (2) |
C16 | 0.0302 (12) | 0.0407 (14) | 0.0484 (14) | 0.0002 (11) | 0.0045 (10) | −0.0091 (12) |
C17 | 0.0646 (19) | 0.0361 (15) | 0.0587 (18) | 0.0034 (14) | 0.0073 (15) | −0.0088 (14) |
C18 | 0.082 (2) | 0.069 (2) | 0.0492 (18) | 0.005 (2) | 0.0062 (17) | −0.0137 (18) |
C19 | 0.063 (2) | 0.067 (2) | 0.0559 (19) | −0.0052 (17) | 0.0040 (16) | 0.0039 (17) |
C20 | 0.088 (3) | 0.0448 (18) | 0.071 (2) | −0.0081 (18) | 0.000 (2) | 0.0052 (18) |
C21 | 0.075 (2) | 0.0398 (17) | 0.0613 (19) | −0.0021 (16) | 0.0046 (16) | −0.0086 (15) |
C22 | 0.126 (4) | 0.109 (4) | 0.063 (2) | −0.008 (3) | 0.000 (3) | 0.017 (3) |
N1 | 0.0504 (13) | 0.0415 (13) | 0.0426 (12) | 0.0024 (11) | 0.0059 (10) | 0.0067 (11) |
O1 | 0.0446 (12) | 0.0814 (17) | 0.0565 (13) | 0.0081 (11) | 0.0131 (10) | −0.0025 (12) |
O2 | 0.0406 (11) | 0.0816 (17) | 0.0599 (13) | 0.0075 (11) | −0.0034 (9) | −0.0081 (12) |
O3 | 0.109 (2) | 0.0446 (13) | 0.0723 (16) | 0.0049 (14) | 0.0096 (15) | 0.0082 (12) |
S1 | 0.0406 (4) | 0.0440 (4) | 0.0488 (4) | 0.0053 (3) | 0.0045 (3) | −0.0026 (3) |
C1—C2 | 1.385 (5) | C14—N1 | 1.470 (4) |
C1—C5 | 1.393 (4) | C14—H14A | 0.9600 |
C1—C6 | 1.474 (5) | C14—H14B | 0.9600 |
C2—C3 | 1.358 (5) | C14—H14C | 0.9600 |
C2—H2 | 0.9300 | C15—H15A | 0.9600 |
C3—N1 | 1.336 (4) | C15—H15B | 0.9600 |
C3—H3 | 0.9300 | C15—H15C | 0.9600 |
C4—N1 | 1.346 (4) | C16—C17 | 1.379 (4) |
C4—C5 | 1.366 (5) | C16—C21 | 1.386 (4) |
C4—H4 | 0.9300 | C16—S1 | 1.775 (3) |
C5—H5 | 0.9300 | C17—C18 | 1.389 (5) |
C6—C7 | 1.296 (5) | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | C18—C19 | 1.370 (5) |
C7—C8 | 1.474 (5) | C18—H18 | 0.9300 |
C7—H7 | 0.9300 | C19—C20 | 1.374 (5) |
C8—C9 | 1.373 (5) | C19—C22 | 1.517 (5) |
C8—C13 | 1.378 (5) | C20—C21 | 1.383 (5) |
C9—C10 | 1.386 (6) | C20—H20 | 0.9300 |
C9—H9 | 0.9300 | C21—H21 | 0.9300 |
C10—C11 | 1.357 (6) | C22—H22A | 0.9600 |
C10—H10 | 0.9300 | C22—H22B | 0.9600 |
C11—C12 | 1.373 (6) | C22—H22C | 0.9600 |
C11—C15 | 1.507 (6) | O1—S1 | 1.446 (2) |
C12—C13 | 1.374 (6) | O2—S1 | 1.449 (2) |
C12—H12 | 0.9300 | O3—S1 | 1.446 (3) |
C13—H13 | 0.9300 | ||
C2—C1—C5 | 116.4 (3) | N1—C14—H14C | 109.5 |
C2—C1—C6 | 118.6 (3) | H14A—C14—H14C | 109.5 |
C5—C1—C6 | 124.9 (3) | H14B—C14—H14C | 109.5 |
C3—C2—C1 | 120.9 (3) | C11—C15—H15A | 109.5 |
C3—C2—H2 | 119.5 | C11—C15—H15B | 109.5 |
C1—C2—H2 | 119.5 | H15A—C15—H15B | 109.5 |
N1—C3—C2 | 121.5 (3) | C11—C15—H15C | 109.5 |
N1—C3—H3 | 119.3 | H15A—C15—H15C | 109.5 |
C2—C3—H3 | 119.3 | H15B—C15—H15C | 109.5 |
N1—C4—C5 | 120.7 (3) | C17—C16—C21 | 118.7 (3) |
N1—C4—H4 | 119.6 | C17—C16—S1 | 119.8 (2) |
C5—C4—H4 | 119.6 | C21—C16—S1 | 121.5 (2) |
C4—C5—C1 | 120.8 (3) | C16—C17—C18 | 120.3 (3) |
C4—C5—H5 | 119.6 | C16—C17—H17 | 119.9 |
C1—C5—H5 | 119.6 | C18—C17—H17 | 119.9 |
C7—C6—C1 | 125.9 (3) | C19—C18—C17 | 121.7 (3) |
C7—C6—H6 | 117.0 | C19—C18—H18 | 119.1 |
C1—C6—H6 | 117.0 | C17—C18—H18 | 119.1 |
C6—C7—C8 | 126.1 (3) | C18—C19—C20 | 117.2 (3) |
C6—C7—H7 | 117.0 | C18—C19—C22 | 122.4 (4) |
C8—C7—H7 | 117.0 | C20—C19—C22 | 120.4 (4) |
C9—C8—C13 | 116.0 (3) | C19—C20—C21 | 122.6 (3) |
C9—C8—C7 | 119.5 (3) | C19—C20—H20 | 118.7 |
C13—C8—C7 | 124.5 (3) | C21—C20—H20 | 118.7 |
C8—C9—C10 | 121.7 (4) | C20—C21—C16 | 119.5 (3) |
C8—C9—H9 | 119.2 | C20—C21—H21 | 120.3 |
C10—C9—H9 | 119.2 | C16—C21—H21 | 120.3 |
C11—C10—C9 | 121.7 (4) | C19—C22—H22A | 109.5 |
C11—C10—H10 | 119.1 | C19—C22—H22B | 109.5 |
C9—C10—H10 | 119.1 | H22A—C22—H22B | 109.5 |
C10—C11—C12 | 117.2 (4) | C19—C22—H22C | 109.5 |
C10—C11—C15 | 122.0 (4) | H22A—C22—H22C | 109.5 |
C12—C11—C15 | 120.8 (4) | H22B—C22—H22C | 109.5 |
C11—C12—C13 | 121.2 (4) | C3—N1—C4 | 119.6 (3) |
C11—C12—H12 | 119.4 | C3—N1—C14 | 120.5 (3) |
C13—C12—H12 | 119.4 | C4—N1—C14 | 119.8 (3) |
C12—C13—C8 | 122.2 (4) | O1—S1—O3 | 113.58 (17) |
C12—C13—H13 | 118.9 | O1—S1—O2 | 112.85 (14) |
C8—C13—H13 | 118.9 | O3—S1—O2 | 113.34 (17) |
N1—C14—H14A | 109.5 | O1—S1—C16 | 104.78 (13) |
N1—C14—H14B | 109.5 | O3—S1—C16 | 106.24 (15) |
H14A—C14—H14B | 109.5 | O2—S1—C16 | 105.02 (14) |
C5—C1—C2—C3 | −0.6 (5) | C21—C16—C17—C18 | 0.6 (5) |
C6—C1—C2—C3 | 178.0 (3) | S1—C16—C17—C18 | −179.7 (3) |
C1—C2—C3—N1 | 0.0 (5) | C16—C17—C18—C19 | −0.4 (6) |
N1—C4—C5—C1 | −0.4 (5) | C17—C18—C19—C20 | 0.2 (6) |
C2—C1—C5—C4 | 0.8 (5) | C17—C18—C19—C22 | −179.5 (4) |
C6—C1—C5—C4 | −177.7 (3) | C18—C19—C20—C21 | −0.2 (6) |
C2—C1—C6—C7 | −177.8 (3) | C22—C19—C20—C21 | 179.5 (4) |
C5—C1—C6—C7 | 0.6 (6) | C19—C20—C21—C16 | 0.4 (6) |
C1—C6—C7—C8 | 178.2 (3) | C17—C16—C21—C20 | −0.6 (5) |
C6—C7—C8—C9 | 174.9 (4) | S1—C16—C21—C20 | 179.6 (3) |
C6—C7—C8—C13 | −5.5 (6) | C2—C3—N1—C4 | 0.4 (5) |
C13—C8—C9—C10 | 0.4 (6) | C2—C3—N1—C14 | 177.8 (3) |
C7—C8—C9—C10 | 180.0 (4) | C5—C4—N1—C3 | −0.2 (5) |
C8—C9—C10—C11 | −0.2 (7) | C5—C4—N1—C14 | −177.6 (3) |
C9—C10—C11—C12 | −0.4 (6) | C17—C16—S1—O1 | 124.9 (2) |
C9—C10—C11—C15 | 179.7 (4) | C21—C16—S1—O1 | −55.3 (3) |
C10—C11—C12—C13 | 0.9 (7) | C17—C16—S1—O3 | 4.4 (3) |
C15—C11—C12—C13 | −179.2 (4) | C21—C16—S1—O3 | −175.8 (3) |
C11—C12—C13—C8 | −0.8 (7) | C17—C16—S1—O2 | −116.0 (3) |
C9—C8—C13—C12 | 0.1 (6) | C21—C16—S1—O2 | 63.8 (3) |
C7—C8—C13—C12 | −179.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.42 | 3.273 (4) | 152 |
C14—H14B···O1ii | 0.96 | 2.59 | 3.482 (4) | 155 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H16N+·C7H7O3S− |
Mr | 381.48 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 9.1380 (6), 6.4257 (5), 33.884 (2) |
β (°) | 95.004 (4) |
V (Å3) | 1982.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.28 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.950, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18512, 4902, 3850 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.184, 1.13 |
No. of reflections | 4902 |
No. of parameters | 247 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.37 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.93 | 2.42 | 3.273 (4) | 152 |
C14—H14B···O1ii | 0.96 | 2.59 | 3.482 (4) | 155 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z. |
Acknowledgements
The authors wish to acknowledge the SAIF, IIT Madras for the data collection. MK would also like to thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for providing financial support (project No. 03 (1200)/EMR-II).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In continuation of our studies of molecular compounds with non linear optical properties which are known to exhibit applications in optoelectronic and photonic devices (Bosshard et al., 1995; Nalwa & Miyata, 1997), we determined the crystal structure of the title compound I.
The asymmetric unit of I, (Fig. 1), contains C15H16N+ cation and C7H7O3S- anion. The geometric parameters of the title compound are comparable with the similar reported structures: Murugavel et al., 2009; Sivakumar et al., 2012; Okada et al., 1990. The cation is planar - torsion angle about the double bond between the two rings in the cation, C1–C6═C7–C8 is 178.2 (3)°. The benzene ring in the anion is almost planar, with the maximum deviation of 0.003 (3)Å.
In the crystal structure, the adjacent anions and cations are linked by weak non-classical C–H···O H bonds (Table 1 & Fig.2) and π–π interactions - Cg1···Cg2iii = 3.749 (2)Å, where Cg1 and Cg2 are the centroids of the rings (C1-C5/N1) and (C8-C13), respectively. Symmetry code: (iii) x, -y-1/2, z+1/2.