1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate.

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 inter-actions, 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

C15H16N+·C7H7O3S−

M = 381.48

Monoclinic,

a = 9.1380 (6) Å

b = 6.4257 (5) Å

c = 33.884 (2) Å

β = 95.004 (4)°

V = 1982.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.964

18512 measured reflections

4902 independent reflections

3850 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.184

S = 1.13

4902 reflections

247 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044509/rk2384sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044509/rk2384Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044509/rk2384Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .