(E)-1-Methyl-4-[2-(1-naphth-yl)vin-yl]pyridinium 4-chloro-benzene-sulfonate.

In the title compound, C(18)H(16)N(+)·C(6)H(4)ClO(3)S(-), the cation exists in an E configuration with respect to the central C=C bond. The naphthalene ring system is slightly bent, the dihedral angle between the two aromatic rings being 3.71 (14)°. The whole cation is twisted, the dihedral angles between the pyridinium and the two aromatic rings of the naphthalene ring system being 47.44 (14) and 50.81 (14)°. The pyridinium ring and the benzene ring of the anion are inclined to each other at a dihedral angle of 68.21 (13)°. In the crystal structure, the cations and anions are arranged alternately with the cations stacked in an anti-parallel manner along the c axis and the anions linked into chains along the same direction. The cations are linked to the anions by weak C-H⋯O inter-actions, forming a three-dimensional network. The crystal structure is further stabilized by C-H⋯π inter-actions and π-π contacts with centroid-centroid distances of 3.6374 (16) and 3.6733 (17) Å. A short Cl⋯O contact [3.108 (2) Å] is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to NLO materials, see: Amila et al. (2004 ▶); Babu et al. (2009 ▶); Chandramohan et al. (2008 ▶); Martin et al. (2002 ▶); Srinivasan et al. (2007 ▶); Yildiz et al. (2009 ▶). For related structures, see: Chantrapromma et al. (2007 ▶, 2009 ▶); Fun et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H16N+·C6H4ClO3S−

M = 437.93

Orthorhombic,

a = 12.3379 (8) Å

b = 21.8466 (16) Å

c = 7.5032 (5) Å

V = 2022.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 100 K

0.52 × 0.15 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.852, T max = 0.990

26247 measured reflections

5881 independent reflections

5018 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.119

S = 1.03

5881 reflections

272 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 2716 Friedel pairs

Flack parameter: 0.01 (6)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047734/is2479sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047734/is2479Isup2.hkl

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

C18H16N+·C6H4ClO3S−	Dx = 1.438 Mg m−3
Mr = 437.93	Melting point = 476–477 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5881 reflections
a = 12.3379 (8) Å	θ = 2.5–30.0°
b = 21.8466 (16) Å	µ = 0.32 mm−1
c = 7.5032 (5) Å	T = 100 K
V = 2022.4 (2) Å3	Needle, yellow
Z = 4	0.52 × 0.15 × 0.03 mm
F(000) = 912

Bruker APEXII CCD area-detector diffractometer	5881 independent reflections
Radiation source: sealed tube	5018 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.852, Tmax = 0.990	k = −25→30
26247 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0563P)2 + 1.1415P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5881 reflections	Δρmax = 0.79 e Å−3
272 parameters	Δρmin = −0.32 e Å−3
1 restraint	Absolute structure: Flack (1983), 2716 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	−0.09030 (5)	0.23662 (3)	0.30957 (10)	0.02946 (15)
S1	0.22593 (4)	0.33346 (2)	0.90465 (9)	0.01933 (12)
O1	0.15823 (14)	0.35562 (10)	1.0481 (3)	0.0330 (5)
O2	0.28543 (16)	0.27849 (8)	0.9519 (3)	0.0334 (5)
O3	0.29257 (15)	0.37986 (9)	0.8218 (3)	0.0345 (5)
N1	1.27331 (16)	0.61843 (10)	0.6247 (3)	0.0254 (5)
C1	0.8387 (2)	0.39813 (12)	0.5753 (4)	0.0285 (6)
H1A	0.9051	0.3871	0.5262	0.034*
C2	0.7561 (2)	0.35470 (13)	0.5858 (4)	0.0329 (6)
H2A	0.7677	0.3153	0.5428	0.040*
C3	0.6593 (2)	0.36949 (13)	0.6579 (4)	0.0329 (6)
H3A	0.6043	0.3404	0.6621	0.040*
C4	0.6405 (2)	0.42940 (13)	0.7278 (4)	0.0285 (6)
C5	0.5414 (2)	0.44348 (13)	0.8145 (4)	0.0331 (6)
H5A	0.4872	0.4140	0.8209	0.040*
C6	0.5245 (2)	0.49983 (14)	0.8888 (4)	0.0346 (6)
H6A	0.4606	0.5079	0.9502	0.042*
C7	0.6038 (2)	0.54547 (13)	0.8719 (4)	0.0347 (7)
H7A	0.5909	0.5842	0.9191	0.042*
C8	0.7004 (2)	0.53381 (12)	0.7868 (4)	0.0307 (6)
H8A	0.7517	0.5647	0.7753	0.037*
C9	0.7219 (2)	0.47452 (12)	0.7161 (4)	0.0254 (5)
C10	0.8240 (2)	0.45755 (12)	0.6368 (4)	0.0270 (6)
C11	0.9108 (2)	0.50246 (12)	0.6253 (4)	0.0269 (6)
H11A	0.8919	0.5431	0.6063	0.032*
C12	1.0164 (2)	0.48887 (12)	0.6404 (4)	0.0287 (6)
H12A	1.0349	0.4482	0.6602	0.034*
C13	1.1056 (2)	0.53391 (12)	0.6279 (4)	0.0246 (5)
C14	1.09004 (19)	0.59384 (11)	0.5685 (4)	0.0237 (5)
H14A	1.0217	0.6060	0.5300	0.028*
C15	1.17418 (19)	0.63513 (11)	0.5659 (4)	0.0226 (5)
H15A	1.1628	0.6746	0.5236	0.027*
C16	1.2913 (2)	0.56030 (14)	0.6814 (4)	0.0295 (6)
H16A	1.3602	0.5492	0.7195	0.035*
C17	1.2101 (2)	0.51791 (13)	0.6835 (4)	0.0262 (5)
H17A	1.2243	0.4782	0.7220	0.031*
C18	1.3610 (2)	0.66379 (14)	0.6319 (5)	0.0351 (7)
H18A	1.3364	0.7016	0.5810	0.053*
H18B	1.4222	0.6490	0.5657	0.053*
H18C	1.3817	0.6704	0.7537	0.053*
C19	0.15667 (19)	0.31883 (11)	0.5567 (4)	0.0236 (5)
H19A	0.2191	0.3400	0.5250	0.028*
C20	0.0877 (2)	0.29687 (11)	0.4251 (4)	0.0252 (5)
H20A	0.1034	0.3034	0.3053	0.030*
C21	−0.0051 (2)	0.26499 (11)	0.4749 (4)	0.0243 (5)
C22	−0.03135 (19)	0.25634 (12)	0.6525 (4)	0.0243 (5)
H22A	−0.0946	0.2358	0.6839	0.029*
C23	0.03806 (19)	0.27873 (11)	0.7836 (4)	0.0218 (5)
H23A	0.0212	0.2733	0.9034	0.026*
C24	0.13284 (19)	0.30930 (11)	0.7354 (3)	0.0200 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0291 (3)	0.0304 (3)	0.0289 (3)	0.0041 (2)	−0.0085 (3)	−0.0063 (3)
S1	0.0201 (2)	0.0166 (2)	0.0212 (3)	0.0019 (2)	0.0004 (2)	0.0021 (2)
O1	0.0269 (9)	0.0453 (11)	0.0269 (11)	0.0013 (8)	−0.0008 (8)	−0.0109 (10)
O2	0.0385 (11)	0.0259 (9)	0.0359 (12)	0.0103 (8)	−0.0144 (9)	−0.0033 (8)
O3	0.0330 (9)	0.0374 (11)	0.0330 (11)	−0.0125 (8)	−0.0062 (9)	0.0090 (10)
N1	0.0193 (9)	0.0272 (11)	0.0296 (12)	−0.0021 (8)	0.0001 (9)	−0.0025 (9)
C1	0.0293 (12)	0.0293 (13)	0.0268 (14)	0.0079 (10)	−0.0029 (11)	−0.0006 (12)
C2	0.0407 (15)	0.0218 (12)	0.0362 (17)	−0.0005 (11)	−0.0091 (13)	−0.0015 (12)
C3	0.0385 (15)	0.0263 (13)	0.0340 (17)	−0.0031 (11)	−0.0076 (13)	0.0042 (12)
C4	0.0308 (12)	0.0292 (13)	0.0256 (14)	0.0020 (11)	−0.0024 (11)	0.0058 (11)
C5	0.0294 (12)	0.0393 (15)	0.0305 (15)	−0.0015 (11)	−0.0047 (13)	0.0090 (14)
C6	0.0268 (12)	0.0488 (16)	0.0283 (15)	0.0093 (12)	0.0010 (13)	0.0068 (14)
C7	0.0346 (13)	0.0322 (14)	0.0374 (17)	0.0130 (11)	−0.0045 (12)	−0.0006 (13)
C8	0.0294 (12)	0.0215 (12)	0.0413 (17)	0.0039 (10)	−0.0046 (12)	0.0033 (12)
C9	0.0264 (12)	0.0246 (12)	0.0252 (14)	0.0019 (10)	0.0000 (11)	0.0050 (11)
C10	0.0265 (12)	0.0220 (12)	0.0325 (15)	−0.0011 (10)	−0.0055 (11)	0.0016 (11)
C11	0.0285 (12)	0.0227 (12)	0.0297 (15)	−0.0004 (10)	0.0006 (11)	0.0013 (11)
C12	0.0322 (13)	0.0228 (13)	0.0313 (16)	0.0018 (10)	−0.0036 (12)	0.0014 (11)
C13	0.0248 (11)	0.0215 (11)	0.0274 (14)	0.0027 (9)	0.0025 (11)	−0.0030 (10)
C14	0.0203 (10)	0.0222 (11)	0.0285 (14)	0.0013 (9)	0.0043 (10)	−0.0010 (11)
C15	0.0226 (11)	0.0215 (11)	0.0239 (13)	0.0011 (9)	0.0037 (10)	0.0019 (10)
C16	0.0255 (12)	0.0361 (15)	0.0268 (14)	0.0087 (11)	−0.0039 (11)	−0.0023 (12)
C17	0.0303 (13)	0.0250 (12)	0.0233 (13)	0.0046 (10)	0.0035 (11)	0.0021 (10)
C18	0.0219 (12)	0.0359 (15)	0.0475 (19)	−0.0072 (11)	−0.0005 (12)	−0.0064 (14)
C19	0.0233 (11)	0.0217 (11)	0.0256 (13)	−0.0005 (9)	−0.0004 (10)	0.0017 (10)
C20	0.0305 (12)	0.0242 (12)	0.0210 (13)	0.0039 (9)	0.0011 (11)	0.0013 (11)
C21	0.0243 (11)	0.0210 (11)	0.0277 (14)	0.0038 (9)	−0.0066 (10)	−0.0020 (10)
C22	0.0204 (11)	0.0245 (12)	0.0280 (14)	0.0005 (9)	−0.0020 (10)	0.0013 (11)
C23	0.0215 (10)	0.0212 (11)	0.0226 (14)	0.0026 (9)	0.0005 (10)	0.0003 (10)
C24	0.0206 (10)	0.0182 (11)	0.0211 (12)	0.0024 (9)	−0.0007 (9)	0.0021 (9)

Cl1—C21	1.740 (3)	C10—C11	1.455 (4)
S1—O1	1.446 (2)	C11—C12	1.341 (4)
S1—O3	1.446 (2)	C11—H11A	0.9300
S1—O2	1.4514 (18)	C12—C13	1.480 (4)
S1—C24	1.792 (3)	C12—H12A	0.9300
N1—C15	1.350 (3)	C13—C14	1.396 (4)
N1—C16	1.358 (4)	C13—C17	1.400 (4)
N1—C18	1.468 (3)	C14—C15	1.375 (3)
C1—C10	1.389 (4)	C14—H14A	0.9300
C1—C2	1.395 (4)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.364 (4)
C2—C3	1.351 (4)	C16—H16A	0.9300
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.429 (4)	C18—H18A	0.9600
C3—H3A	0.9300	C18—H18B	0.9600
C4—C9	1.410 (4)	C18—H18C	0.9600
C4—C5	1.419 (4)	C19—C24	1.388 (4)
C5—C6	1.367 (4)	C19—C20	1.389 (4)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.402 (4)	C20—C21	1.392 (4)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.376 (4)	C21—C22	1.384 (4)
C7—H7A	0.9300	C22—C23	1.393 (4)
C8—C9	1.425 (4)	C22—H22A	0.9300
C8—H8A	0.9300	C23—C24	1.395 (3)
C9—C10	1.441 (4)	C23—H23A	0.9300
O1—S1—O3	114.45 (13)	C11—C12—C13	124.8 (2)
O1—S1—O2	112.79 (13)	C11—C12—H12A	117.6
O3—S1—O2	113.43 (12)	C13—C12—H12A	117.6
O1—S1—C24	104.83 (11)	C14—C13—C17	117.1 (2)
O3—S1—C24	105.43 (12)	C14—C13—C12	122.8 (2)
O2—S1—C24	104.70 (11)	C17—C13—C12	120.0 (2)
C15—N1—C16	120.2 (2)	C15—C14—C13	121.0 (2)
C15—N1—C18	119.8 (2)	C15—C14—H14A	119.5
C16—N1—C18	120.0 (2)	C13—C14—H14A	119.5
C10—C1—C2	121.4 (3)	N1—C15—C14	120.1 (2)
C10—C1—H1A	119.3	N1—C15—H15A	119.9
C2—C1—H1A	119.3	C14—C15—H15A	119.9
C3—C2—C1	120.4 (3)	N1—C16—C17	121.2 (2)
C3—C2—H2A	119.8	N1—C16—H16A	119.4
C1—C2—H2A	119.8	C17—C16—H16A	119.4
C2—C3—C4	120.6 (3)	C16—C17—C13	120.2 (2)
C2—C3—H3A	119.7	C16—C17—H17A	119.9
C4—C3—H3A	119.7	C13—C17—H17A	119.9
C9—C4—C5	119.4 (3)	N1—C18—H18A	109.5
C9—C4—C3	120.2 (3)	N1—C18—H18B	109.5
C5—C4—C3	120.4 (3)	H18A—C18—H18B	109.5
C6—C5—C4	120.9 (3)	N1—C18—H18C	109.5
C6—C5—H5A	119.6	H18A—C18—H18C	109.5
C4—C5—H5A	119.6	H18B—C18—H18C	109.5
C5—C6—C7	119.8 (3)	C24—C19—C20	120.3 (2)
C5—C6—H6A	120.1	C24—C19—H19A	119.8
C7—C6—H6A	120.1	C20—C19—H19A	119.8
C8—C7—C6	120.9 (3)	C19—C20—C21	119.1 (3)
C8—C7—H7A	119.5	C19—C20—H20A	120.5
C6—C7—H7A	119.5	C21—C20—H20A	120.5
C7—C8—C9	120.2 (3)	C22—C21—C20	121.3 (2)
C7—C8—H8A	119.9	C22—C21—Cl1	119.7 (2)
C9—C8—H8A	119.9	C20—C21—Cl1	119.0 (2)
C4—C9—C8	118.6 (2)	C21—C22—C23	119.2 (2)
C4—C9—C10	117.9 (2)	C21—C22—H22A	120.4
C8—C9—C10	123.4 (2)	C23—C22—H22A	120.4
C1—C10—C9	119.4 (2)	C22—C23—C24	120.0 (3)
C1—C10—C11	121.0 (3)	C22—C23—H23A	120.0
C9—C10—C11	119.6 (2)	C24—C23—H23A	120.0
C12—C11—C10	124.1 (2)	C19—C24—C23	120.0 (2)
C12—C11—H11A	118.0	C19—C24—S1	120.30 (18)
C10—C11—H11A	118.0	C23—C24—S1	119.6 (2)
C10—C1—C2—C3	−0.5 (5)	C17—C13—C14—C15	−0.3 (4)
C1—C2—C3—C4	−1.2 (5)	C12—C13—C14—C15	177.2 (3)
C2—C3—C4—C9	2.4 (4)	C16—N1—C15—C14	2.0 (4)
C2—C3—C4—C5	−175.6 (3)	C18—N1—C15—C14	−176.2 (3)
C9—C4—C5—C6	−0.9 (4)	C13—C14—C15—N1	−1.3 (4)
C3—C4—C5—C6	177.1 (3)	C15—N1—C16—C17	−1.1 (4)
C4—C5—C6—C7	3.1 (5)	C18—N1—C16—C17	177.1 (3)
C5—C6—C7—C8	−2.2 (5)	N1—C16—C17—C13	−0.5 (5)
C6—C7—C8—C9	−0.9 (5)	C14—C13—C17—C16	1.2 (4)
C5—C4—C9—C8	−2.1 (4)	C12—C13—C17—C16	−176.4 (3)
C3—C4—C9—C8	179.8 (3)	C24—C19—C20—C21	−0.3 (4)
C5—C4—C9—C10	176.3 (3)	C19—C20—C21—C22	1.8 (4)
C3—C4—C9—C10	−1.8 (4)	C19—C20—C21—Cl1	−179.12 (19)
C7—C8—C9—C4	3.0 (4)	C20—C21—C22—C23	−1.6 (4)
C7—C8—C9—C10	−175.3 (3)	Cl1—C21—C22—C23	179.36 (18)
C2—C1—C10—C9	1.1 (4)	C21—C22—C23—C24	−0.2 (4)
C2—C1—C10—C11	180.0 (3)	C20—C19—C24—C23	−1.4 (4)
C4—C9—C10—C1	0.1 (4)	C20—C19—C24—S1	176.12 (18)
C8—C9—C10—C1	178.4 (3)	C22—C23—C24—C19	1.7 (4)
C4—C9—C10—C11	−178.8 (3)	C22—C23—C24—S1	−175.90 (18)
C8—C9—C10—C11	−0.5 (4)	O1—S1—C24—C19	142.5 (2)
C1—C10—C11—C12	−33.3 (4)	O3—S1—C24—C19	21.3 (2)
C9—C10—C11—C12	145.6 (3)	O2—S1—C24—C19	−98.6 (2)
C10—C11—C12—C13	179.6 (3)	O1—S1—C24—C23	−40.0 (2)
C11—C12—C13—C14	−11.4 (5)	O3—S1—C24—C23	−161.1 (2)
C11—C12—C13—C17	166.1 (3)	O2—S1—C24—C23	79.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3	0.93	2.51	3.370 (3)	153
C11—H11A···O1i	0.93	2.34	3.267 (3)	178
C14—H14A···O1i	0.93	2.38	3.260 (3)	158
C15—H15A···O2ii	0.93	2.42	3.285 (3)	155
C17—H17A···O3iii	0.93	2.43	3.348 (3)	171
C18—H18A···O2ii	0.96	2.45	3.372 (4)	160
C20—H20A···O1iv	0.93	2.34	3.226 (4)	159
C22—H22A···O2v	0.93	2.52	3.277 (3)	139
C1—H1A···Cg4iii	0.93	2.98	3.682 (3)	133
C3—H3A···Cg4vi	0.93	2.87	3.651 (3)	142
C6—H6A···Cg3vii	0.93	2.82	3.593 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3	0.93	2.51	3.370 (3)	153
C11—H11A⋯O1i	0.93	2.34	3.267 (3)	178
C14—H14A⋯O1i	0.93	2.38	3.260 (3)	158
C15—H15A⋯O2ii	0.93	2.42	3.285 (3)	155
C17—H17A⋯O3iii	0.93	2.43	3.348 (3)	171
C18—H18A⋯O2ii	0.96	2.45	3.372 (4)	160
C20—H20A⋯O1iv	0.93	2.34	3.226 (4)	159
C22—H22A⋯O2v	0.93	2.52	3.277 (3)	139
C1—H1A⋯Cg4iii	0.93	2.98	3.682 (3)	133
C3—H3A⋯Cg4vi	0.93	2.87	3.651 (3)	142
C6—H6A⋯Cg3vii	0.93	2.82	3.593 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C13–C17, C1–C4/C9/C10, C4–C9 and C19–C24 rings, respectively.