4-[2-(4-But-oxy-phen-yl)ethen-yl]-1-methyl-pyridinium tosylate.

In the title mol-ecular salt, C18H22NO(+)·C7H7O3S(-), the dihedral angle between the aromatic rings in the cation is 10.00 (9)°; its alkyl side chain adopts an extended conformation. In the crystal, weak C-H⋯O and π-π [centroid-centroid distance = 3.7658 (17) Å] inter-actions link the components, generating a three-dimensional network.

Related literature

For mol­ecular compounds with non-linear optical properties, see: Nalwa & Miyata (1997 ▶). For related structures, see: Krishnakumar et al. (2012 ▶); Sivakumar et al.(2012 ▶).

Experimental

Crystal data

C18H22NO+·C7H7O3S−

M = 439.55

Monoclinic,

a = 9.0884 (6) Å

b = 6.4559 (5) Å

c = 39.827 (3) Å

β = 95.404 (3)°

V = 2326.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.954, T max = 0.967

20608 measured reflections

5629 independent reflections

4258 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.160

S = 1.16

5629 reflections

291 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.39 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/S1600536813009616/hb7067sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009616/hb7067Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009616/hb7067Isup3.cml

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

C18H22NO+·C7H7O3S−	F(000) = 936
Mr = 439.55	Dx = 1.255 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4259 reflections
a = 9.0884 (6) Å	θ = 2.0–28.3°
b = 6.4559 (5) Å	µ = 0.17 mm−1
c = 39.827 (3) Å	T = 295 K
β = 95.404 (3)°	Block, colourless
V = 2326.4 (2) Å3	0.28 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	5629 independent reflections
Radiation source: fine-focus sealed tube	4258 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.954, Tmax = 0.967	k = −8→8
20608 measured reflections	l = −53→53

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0359P)2 + 2.0379P] where P = (Fo2 + 2Fc2)/3
5629 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.50367 (7)	0.31025 (11)	0.192843 (17)	0.04861 (19)
O1	0.5412 (3)	1.3940 (4)	0.42984 (6)	0.0809 (7)
O2	0.5079 (3)	0.5330 (3)	0.19010 (6)	0.0789 (7)
O3	0.6435 (2)	0.2208 (4)	0.20606 (5)	0.0640 (6)
O4	0.3804 (2)	0.2348 (4)	0.20972 (5)	0.0664 (6)
N1	0.4977 (2)	0.0292 (3)	0.27689 (5)	0.0469 (5)
C1	0.3694 (3)	0.0849 (5)	0.28821 (7)	0.0573 (7)
H1	0.2863	0.0023	0.2833	0.069*
C2	0.3587 (3)	0.2596 (5)	0.30663 (7)	0.0575 (7)
H2	0.2683	0.2937	0.3144	0.069*
C3	0.4789 (3)	0.3888 (4)	0.31426 (6)	0.0466 (6)
C4	0.6110 (3)	0.3277 (5)	0.30151 (7)	0.0503 (6)
H4	0.6949	0.4097	0.3055	0.060*
C5	0.6177 (3)	0.1500 (4)	0.28339 (7)	0.0500 (6)
H5	0.7066	0.1114	0.2754	0.060*
C6	0.5076 (4)	−0.1583 (5)	0.25612 (7)	0.0612 (8)
H6A	0.4267	−0.2491	0.2596	0.092*
H6B	0.5993	−0.2279	0.2625	0.092*
H6C	0.5031	−0.1200	0.2328	0.092*
C7	0.4653 (3)	0.5724 (5)	0.33512 (7)	0.0556 (7)
H7	0.3736	0.5967	0.3429	0.067*
C8	0.5707 (3)	0.7068 (5)	0.34388 (7)	0.0519 (7)
H8	0.6614	0.6843	0.3354	0.062*
C9	0.5600 (3)	0.8877 (5)	0.36552 (6)	0.0497 (6)
C10	0.4379 (3)	0.9313 (6)	0.38288 (8)	0.0700 (9)
H10	0.3564	0.8437	0.3803	0.084*
C11	0.4343 (4)	1.0995 (6)	0.40360 (9)	0.0765 (10)
H11	0.3508	1.1248	0.4148	0.092*
C12	0.5539 (3)	1.2327 (5)	0.40816 (7)	0.0607 (8)
C13	0.6756 (3)	1.1942 (5)	0.39102 (8)	0.0653 (8)
H13	0.7565	1.2829	0.3935	0.078*
C14	0.6773 (3)	1.0237 (5)	0.37012 (7)	0.0580 (7)
H14	0.7605	0.9996	0.3587	0.070*
C15	0.6659 (4)	1.5244 (6)	0.43681 (8)	0.0738 (9)
H15A	0.6903	1.5913	0.4162	0.089*
H15B	0.7504	1.4430	0.4457	0.089*
C16	0.6299 (5)	1.6859 (6)	0.46230 (9)	0.0851 (11)
H16A	0.5430	1.7627	0.4535	0.102*
H16B	0.6073	1.6175	0.4829	0.102*
C17	0.7561 (6)	1.8339 (7)	0.47022 (10)	0.1014 (14)
H17A	0.7817	1.8957	0.4493	0.122*
H17B	0.8414	1.7567	0.4799	0.122*
C18	0.7232 (7)	2.0047 (8)	0.49432 (12)	0.133 (2)
H18A	0.6429	2.0875	0.4844	0.199*
H18B	0.8093	2.0900	0.4989	0.199*
H18C	0.6967	1.9451	0.5150	0.199*
C19	0.4720 (2)	0.2172 (4)	0.15089 (6)	0.0428 (6)
C20	0.4479 (4)	0.3501 (5)	0.12436 (8)	0.0613 (8)
C21	0.4179 (4)	0.2789 (6)	0.09167 (8)	0.0700 (9)
H21	0.4026	0.3738	0.0741	0.084*
C22	0.4105 (4)	0.0713 (6)	0.08467 (8)	0.0687 (9)
C23	0.4372 (4)	−0.0616 (5)	0.11138 (9)	0.0737 (10)
C24	0.4687 (3)	0.0078 (5)	0.14422 (8)	0.0597 (8)
H24	0.4875	−0.0869	0.1617	0.072*
C25	0.3715 (5)	−0.0092 (8)	0.04919 (10)	0.1049 (14)
H25A	0.4179	−0.1412	0.0467	0.157*
H25B	0.4056	0.0868	0.0332	0.157*
H25C	0.2663	−0.0243	0.0451	0.157*
H23	0.435 (4)	−0.2033 (19)	0.1073 (8)	0.083 (11)*
H20	0.449 (3)	0.489 (2)	0.1308 (8)	0.071 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0408 (3)	0.0486 (4)	0.0569 (4)	0.0088 (3)	0.0075 (3)	0.0052 (3)
O1	0.0891 (17)	0.0787 (17)	0.0752 (15)	0.0093 (14)	0.0099 (12)	−0.0245 (13)
O2	0.1106 (19)	0.0453 (13)	0.0813 (15)	0.0024 (13)	0.0112 (13)	−0.0055 (11)
O3	0.0428 (10)	0.0851 (16)	0.0633 (12)	0.0141 (10)	0.0009 (8)	0.0020 (11)
O4	0.0463 (10)	0.0839 (16)	0.0715 (13)	0.0134 (11)	0.0189 (9)	0.0157 (12)
N1	0.0499 (12)	0.0433 (13)	0.0469 (11)	−0.0035 (10)	0.0009 (9)	0.0074 (10)
C1	0.0428 (14)	0.0621 (19)	0.0664 (17)	−0.0118 (14)	0.0022 (12)	0.0051 (16)
C2	0.0379 (13)	0.069 (2)	0.0667 (17)	−0.0022 (13)	0.0094 (12)	0.0010 (16)
C3	0.0433 (13)	0.0479 (15)	0.0486 (13)	0.0010 (12)	0.0046 (10)	0.0079 (12)
C4	0.0405 (12)	0.0525 (16)	0.0580 (15)	−0.0096 (12)	0.0058 (11)	−0.0002 (14)
C5	0.0413 (13)	0.0511 (17)	0.0586 (15)	−0.0037 (12)	0.0104 (11)	0.0030 (13)
C6	0.078 (2)	0.0452 (16)	0.0594 (16)	−0.0041 (15)	−0.0014 (14)	−0.0017 (14)
C7	0.0431 (14)	0.0617 (19)	0.0630 (16)	0.0058 (14)	0.0108 (12)	0.0020 (15)
C8	0.0455 (13)	0.0559 (17)	0.0548 (15)	0.0068 (13)	0.0072 (11)	0.0052 (14)
C9	0.0495 (14)	0.0526 (17)	0.0469 (13)	0.0107 (13)	0.0044 (11)	0.0026 (13)
C10	0.0547 (17)	0.080 (2)	0.077 (2)	−0.0043 (17)	0.0136 (15)	−0.0155 (19)
C11	0.0638 (19)	0.091 (3)	0.077 (2)	0.0096 (19)	0.0193 (16)	−0.020 (2)
C12	0.0690 (19)	0.061 (2)	0.0519 (15)	0.0182 (16)	0.0064 (13)	−0.0063 (14)
C13	0.0618 (17)	0.066 (2)	0.0682 (18)	−0.0005 (16)	0.0069 (14)	−0.0090 (17)
C14	0.0527 (16)	0.0624 (19)	0.0605 (16)	0.0072 (14)	0.0129 (13)	−0.0060 (15)
C15	0.095 (3)	0.062 (2)	0.0630 (19)	0.009 (2)	0.0010 (17)	−0.0061 (17)
C16	0.123 (3)	0.069 (2)	0.0623 (19)	0.018 (2)	0.000 (2)	−0.0104 (18)
C17	0.154 (4)	0.078 (3)	0.070 (2)	−0.001 (3)	0.001 (2)	−0.010 (2)
C18	0.208 (6)	0.091 (3)	0.095 (3)	0.000 (4)	−0.008 (3)	−0.029 (3)
C19	0.0328 (11)	0.0383 (14)	0.0576 (14)	0.0006 (10)	0.0062 (10)	0.0095 (12)
C20	0.0727 (19)	0.0432 (17)	0.0667 (18)	0.0019 (15)	−0.0003 (15)	0.0114 (15)
C21	0.080 (2)	0.067 (2)	0.0604 (18)	−0.0054 (18)	−0.0040 (15)	0.0238 (17)
C22	0.069 (2)	0.071 (2)	0.0651 (19)	−0.0089 (18)	0.0039 (15)	−0.0003 (18)
C23	0.097 (3)	0.0449 (19)	0.077 (2)	−0.0071 (18)	−0.0009 (19)	−0.0015 (17)
C24	0.0704 (19)	0.0421 (16)	0.0659 (18)	−0.0007 (14)	0.0022 (14)	0.0145 (14)
C25	0.133 (4)	0.104 (3)	0.075 (2)	−0.023 (3)	−0.003 (2)	−0.011 (2)

S1—O2	1.443 (2)	C12—C13	1.376 (4)
S1—O4	1.445 (2)	C13—C14	1.381 (4)
S1—O3	1.4487 (19)	C13—H13	0.9300
S1—C19	1.773 (3)	C14—H14	0.9300
O1—C12	1.364 (4)	C15—C16	1.512 (5)
O1—C15	1.418 (4)	C15—H15A	0.9700
N1—C1	1.339 (3)	C15—H15B	0.9700
N1—C5	1.346 (3)	C16—C17	1.503 (6)
N1—C6	1.474 (4)	C16—H16A	0.9700
C1—C2	1.354 (4)	C16—H16B	0.9700
C1—H1	0.9300	C17—C18	1.510 (6)
C2—C3	1.385 (4)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.404 (4)	C18—H18A	0.9600
C3—C7	1.459 (4)	C18—H18B	0.9600
C4—C5	1.360 (4)	C18—H18C	0.9600
C4—H4	0.9300	C19—C20	1.363 (4)
C5—H5	0.9300	C19—C24	1.378 (4)
C6—H6A	0.9600	C20—C21	1.383 (5)
C6—H6B	0.9600	C20—H20	0.933 (10)
C6—H6C	0.9600	C21—C22	1.369 (5)
C7—C8	1.315 (4)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.370 (5)
C8—C9	1.460 (4)	C22—C25	1.516 (5)
C8—H8	0.9300	C23—C24	1.386 (5)
C9—C14	1.379 (4)	C23—H23	0.930 (10)
C9—C10	1.391 (4)	C24—H24	0.9300
C10—C11	1.366 (5)	C25—H25A	0.9600
C10—H10	0.9300	C25—H25B	0.9600
C11—C12	1.384 (5)	C25—H25C	0.9600
C11—H11	0.9300
O2—S1—O4	113.47 (14)	C9—C14—C13	122.3 (3)
O2—S1—O3	113.34 (15)	C9—C14—H14	118.8
O4—S1—O3	112.88 (13)	C13—C14—H14	118.8
O2—S1—C19	105.64 (13)	O1—C15—C16	108.8 (3)
O4—S1—C19	105.08 (12)	O1—C15—H15A	109.9
O3—S1—C19	105.44 (12)	C16—C15—H15A	109.9
C12—O1—C15	117.6 (3)	O1—C15—H15B	109.9
C1—N1—C5	119.7 (2)	C16—C15—H15B	109.9
C1—N1—C6	120.7 (2)	H15A—C15—H15B	108.3
C5—N1—C6	119.5 (2)	C17—C16—C15	111.7 (4)
N1—C1—C2	121.0 (3)	C17—C16—H16A	109.3
N1—C1—H1	119.5	C15—C16—H16A	109.3
C2—C1—H1	119.5	C17—C16—H16B	109.3
C1—C2—C3	121.7 (3)	C15—C16—H16B	109.3
C1—C2—H2	119.2	H16A—C16—H16B	107.9
C3—C2—H2	119.2	C16—C17—C18	113.9 (4)
C2—C3—C4	115.8 (3)	C16—C17—H17A	108.8
C2—C3—C7	120.5 (2)	C18—C17—H17A	108.8
C4—C3—C7	123.7 (2)	C16—C17—H17B	108.8
C5—C4—C3	120.8 (2)	C18—C17—H17B	108.8
C5—C4—H4	119.6	H17A—C17—H17B	107.7
C3—C4—H4	119.6	C17—C18—H18A	109.5
N1—C5—C4	121.0 (2)	C17—C18—H18B	109.5
N1—C5—H5	119.5	H18A—C18—H18B	109.5
C4—C5—H5	119.5	C17—C18—H18C	109.5
N1—C6—H6A	109.5	H18A—C18—H18C	109.5
N1—C6—H6B	109.5	H18B—C18—H18C	109.5
H6A—C6—H6B	109.5	C20—C19—C24	118.0 (3)
N1—C6—H6C	109.5	C20—C19—S1	121.1 (2)
H6A—C6—H6C	109.5	C24—C19—S1	120.9 (2)
H6B—C6—H6C	109.5	C19—C20—C21	121.6 (3)
C8—C7—C3	126.0 (3)	C19—C20—H20	113 (2)
C8—C7—H7	117.0	C21—C20—H20	125 (2)
C3—C7—H7	117.0	C22—C21—C20	121.2 (3)
C7—C8—C9	126.6 (3)	C22—C21—H21	119.4
C7—C8—H8	116.7	C20—C21—H21	119.4
C9—C8—H8	116.7	C21—C22—C23	116.9 (3)
C14—C9—C10	116.6 (3)	C21—C22—C25	121.9 (3)
C14—C9—C8	119.6 (2)	C23—C22—C25	121.2 (4)
C10—C9—C8	123.8 (3)	C22—C23—C24	122.4 (3)
C11—C10—C9	121.8 (3)	C22—C23—H23	119 (2)
C11—C10—H10	119.1	C24—C23—H23	119 (2)
C9—C10—H10	119.1	C19—C24—C23	119.8 (3)
C10—C11—C12	120.7 (3)	C19—C24—H24	120.1
C10—C11—H11	119.7	C23—C24—H24	120.1
C12—C11—H11	119.7	C22—C25—H25A	109.5
O1—C12—C13	124.9 (3)	C22—C25—H25B	109.5
O1—C12—C11	116.4 (3)	H25A—C25—H25B	109.5
C13—C12—C11	118.7 (3)	C22—C25—H25C	109.5
C12—C13—C14	119.9 (3)	H25A—C25—H25C	109.5
C12—C13—H13	120.1	H25B—C25—H25C	109.5
C14—C13—H13	120.1
C5—N1—C1—C2	−1.1 (4)	C11—C12—C13—C14	−0.9 (5)
C6—N1—C1—C2	−178.4 (3)	C10—C9—C14—C13	0.5 (4)
N1—C1—C2—C3	0.7 (5)	C8—C9—C14—C13	−178.1 (3)
C1—C2—C3—C4	0.4 (4)	C12—C13—C14—C9	0.1 (5)
C1—C2—C3—C7	−177.9 (3)	C12—O1—C15—C16	−177.7 (3)
C2—C3—C4—C5	−1.1 (4)	O1—C15—C16—C17	−178.4 (3)
C7—C3—C4—C5	177.2 (3)	C15—C16—C17—C18	177.2 (3)
C1—N1—C5—C4	0.4 (4)	O2—S1—C19—C20	−4.2 (3)
C6—N1—C5—C4	177.8 (2)	O4—S1—C19—C20	116.1 (2)
C3—C4—C5—N1	0.7 (4)	O3—S1—C19—C20	−124.5 (2)
C2—C3—C7—C8	−179.6 (3)	O2—S1—C19—C24	176.9 (2)
C4—C3—C7—C8	2.2 (5)	O4—S1—C19—C24	−62.8 (2)
C3—C7—C8—C9	−178.1 (3)	O3—S1—C19—C24	56.7 (3)
C7—C8—C9—C14	−174.7 (3)	C24—C19—C20—C21	1.3 (5)
C7—C8—C9—C10	6.8 (5)	S1—C19—C20—C21	−177.7 (3)
C14—C9—C10—C11	−0.4 (5)	C19—C20—C21—C22	0.4 (5)
C8—C9—C10—C11	178.2 (3)	C20—C21—C22—C23	−1.4 (5)
C9—C10—C11—C12	−0.3 (6)	C20—C21—C22—C25	177.4 (3)
C15—O1—C12—C13	−4.1 (5)	C21—C22—C23—C24	0.8 (6)
C15—O1—C12—C11	175.6 (3)	C25—C22—C23—C24	−178.0 (4)
C10—C11—C12—O1	−178.8 (3)	C20—C19—C24—C23	−1.8 (5)
C10—C11—C12—C13	1.0 (5)	S1—C19—C24—C23	177.1 (3)
O1—C12—C13—C14	178.8 (3)	C22—C23—C24—C19	0.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4i	0.93	2.33	3.210 (3)	158
C4—H4···O3ii	0.93	2.56	3.412 (3)	153
C6—H6B···O3iii	0.96	2.57	3.470 (4)	157
C8—H8···O3ii	0.93	2.55	3.418 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.93	2.33	3.210 (3)	158
C4—H4⋯O3ii	0.93	2.56	3.412 (3)	153
C6—H6B⋯O3iii	0.96	2.57	3.470 (4)	157
C8—H8⋯O3ii	0.93	2.55	3.418 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .