Literature DB >> 23723874

(E)-4-[2-(4-Eth-oxy-phen-yl)ethen-yl]-1-methyl-pyridinium naphthalene-2-sulfonate.

R K Balachandar¹, S Kalainathan, P G Aravindan, Shibu M Eappen, Jiban Podder.

Abstract

In the title salt, C16H18NO(+)·C10H7O3S(-), the substituents attached to the central C=C bond adopt a trans conformation and the benzene and pyridinium rings are nearly coplanar, making a dihedral angle of 6.01 (9)°. The crystal structure features weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions .

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 23723874 PMCID： PMC3648254 DOI： 10.1107/S1600536813009240

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

The title compound was synthesized as part of a search for materials with non-linear optical properties, see: Okada et al. (1990 ▶); Yang et al. (2007 ▶). For the synthesis of the pyridinium precursor, see: Okada et al. (1990 ▶). For related compounds, see: Ruiz et al. (2006 ▶); Murugavel et al. (2009 ▶).

Experimental

Crystal data

C16H18NO+·C10H7O3S− M = 447.53 Monoclinic, a = 10.896 (1) Å b = 17.2838 (16) Å c = 11.8888 (10) Å β = 92.752 (4)° V = 2236.4 (3) Å3 Z = 4 Mo Kα radiation μ = 0.18 mm−1 T = 296 K 0.40 × 0.35 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.932, T max = 0.949 9220 measured reflections 5354 independent reflections 3678 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.159 S = 1.03 5354 reflections 291 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.32 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶)’; software used to prepare material for publication: SHELXL97. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009240/bh2474sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009240/bh2474Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813009240/bh2474Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₈NO⁺·C₁₀H₇O₃S⁻	F(000) = 944
M_r = 447.53	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2935 reflections
a = 10.896 (1) Å	θ = 4.7–55.0°
b = 17.2838 (16) Å	µ = 0.18 mm⁻¹
c = 11.8888 (10) Å	T = 296 K
β = 92.752 (4)°	Block, yellow
V = 2236.4 (3) Å³	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	5354 independent reflections
Radiation source: fine-focus sealed tube	3678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and φ scan	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→14
T_min = 0.932, T_max = 0.949	k = −22→11
9220 measured reflections	l = −15→9

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0795P)² + 0.5684P] where P = (F_o² + 2F_c²)/3
5354 reflections	(Δ/σ)_max = 0.004
291 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³
0 constraints

	x	y	z	U_iso*/U_eq
S1	−0.13928 (4)	0.46834 (3)	0.22800 (4)	0.03758 (16)
O1	−0.22890 (17)	0.26974 (11)	0.70188 (18)	0.0674 (5)
O2	−0.17437 (15)	0.39399 (10)	0.27088 (15)	0.0621 (5)
O3	−0.15214 (14)	0.47353 (9)	0.10620 (13)	0.0496 (4)
O4	−0.19562 (15)	0.53257 (11)	0.28333 (15)	0.0614 (5)
N1	0.67371 (16)	0.21961 (12)	0.39556 (15)	0.0439 (4)
C1	−0.4210 (2)	0.24499 (16)	0.7732 (2)	0.0598 (7)
H1A	−0.4018	0.2784	0.8361	0.090*
H1B	−0.4758	0.2049	0.7956	0.090*
H1C	−0.4596	0.2744	0.7129	0.090*
C2	−0.3040 (2)	0.20899 (16)	0.7340 (2)	0.0569 (6)
H2A	−0.2636	0.1794	0.7943	0.068*
H2B	−0.3221	0.1747	0.6708	0.068*
C3	−0.1151 (2)	0.25166 (14)	0.66518 (19)	0.0464 (5)
C4	−0.0432 (2)	0.31443 (15)	0.6413 (2)	0.0565 (6)
H4	−0.0741	0.3641	0.6501	0.068*
C5	0.0732 (2)	0.30478 (14)	0.6047 (2)	0.0502 (6)
H5	0.1200	0.3480	0.5885	0.060*
C6	0.12266 (19)	0.23083 (13)	0.59137 (17)	0.0382 (5)
C7	0.24500 (19)	0.21686 (13)	0.55280 (17)	0.0396 (5)
H7	0.2698	0.1654	0.5500	0.048*
C8	0.3257 (2)	0.26921 (13)	0.52101 (18)	0.0431 (5)
H8	0.3042	0.3211	0.5255	0.052*
C9	0.44579 (19)	0.25042 (12)	0.47955 (17)	0.0389 (5)
C10	0.4916 (2)	0.17538 (13)	0.47388 (19)	0.0457 (5)
H10	0.4452	0.1343	0.4992	0.055*
C11	0.6037 (2)	0.16135 (14)	0.4317 (2)	0.0487 (5)
H11	0.6322	0.1107	0.4279	0.058*
C12	0.7940 (2)	0.20278 (17)	0.3504 (2)	0.0599 (7)
H12A	0.8180	0.2449	0.3036	0.090*
H12B	0.7888	0.1562	0.3066	0.090*
H12C	0.8540	0.1963	0.4115	0.090*
C13	0.0494 (2)	0.16808 (14)	0.6163 (2)	0.0469 (5)
H13	0.0801	0.1183	0.6082	0.056*
C14	−0.0689 (2)	0.17784 (14)	0.6530 (2)	0.0504 (6)
H14	−0.1166	0.1350	0.6692	0.060*
C15	0.6331 (2)	0.29222 (15)	0.4003 (2)	0.0551 (6)
H15	0.6818	0.3323	0.3752	0.066*
C16	0.5214 (2)	0.30866 (15)	0.4413 (2)	0.0559 (6)
H16	0.4953	0.3598	0.4438	0.067*
C17	0.02063 (18)	0.47725 (11)	0.26229 (16)	0.0335 (4)
C18	0.0604 (2)	0.46691 (12)	0.37619 (17)	0.0403 (5)
H18	0.0045	0.4519	0.4287	0.048*
C19	0.1800 (2)	0.47885 (13)	0.40938 (18)	0.0457 (5)
H19	0.2046	0.4733	0.4849	0.055*
C20	0.26751 (19)	0.49955 (13)	0.33080 (19)	0.0417 (5)
C21	0.3931 (2)	0.51132 (15)	0.3618 (2)	0.0567 (7)
H21	0.4194	0.5074	0.4372	0.068*
C22	0.4766 (2)	0.52831 (16)	0.2831 (3)	0.0651 (8)
H22	0.5590	0.5348	0.3049	0.078*
C23	0.10290 (18)	0.49640 (11)	0.18361 (16)	0.0341 (4)
H23	0.0761	0.5022	0.1086	0.041*
C24	0.22918 (18)	0.50750 (12)	0.21552 (17)	0.0367 (4)
C25	0.3178 (2)	0.52578 (13)	0.1359 (2)	0.0476 (5)
H25	0.2938	0.5309	0.0601	0.057*
C26	0.4380 (2)	0.53582 (16)	0.1703 (3)	0.0620 (7)
H26	0.4952	0.5479	0.1174	0.074*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0314 (3)	0.0373 (3)	0.0442 (3)	−0.0046 (2)	0.00312 (19)	−0.0015 (2)
O1	0.0487 (10)	0.0612 (12)	0.0944 (14)	0.0025 (9)	0.0244 (9)	0.0087 (10)
O2	0.0515 (10)	0.0550 (11)	0.0799 (12)	−0.0178 (8)	0.0034 (9)	0.0173 (9)
O3	0.0410 (8)	0.0584 (10)	0.0486 (9)	−0.0081 (7)	−0.0055 (6)	0.0012 (8)
O4	0.0419 (9)	0.0679 (12)	0.0748 (11)	0.0089 (8)	0.0046 (8)	−0.0213 (9)
N1	0.0359 (9)	0.0542 (12)	0.0424 (9)	−0.0050 (8)	0.0097 (7)	0.0004 (9)
C1	0.0369 (13)	0.0729 (19)	0.0707 (17)	0.0030 (12)	0.0144 (11)	−0.0028 (14)
C2	0.0491 (14)	0.0530 (16)	0.0687 (16)	−0.0018 (12)	0.0035 (12)	−0.0022 (13)
C3	0.0359 (11)	0.0528 (14)	0.0512 (13)	0.0054 (10)	0.0108 (9)	0.0038 (11)
C4	0.0502 (14)	0.0406 (13)	0.0805 (17)	0.0066 (11)	0.0215 (12)	0.0006 (12)
C5	0.0466 (13)	0.0386 (13)	0.0669 (15)	−0.0026 (10)	0.0168 (11)	0.0035 (11)
C6	0.0348 (10)	0.0409 (12)	0.0393 (10)	0.0007 (9)	0.0057 (8)	0.0026 (9)
C7	0.0403 (11)	0.0370 (11)	0.0419 (11)	0.0008 (9)	0.0057 (8)	0.0021 (9)
C8	0.0422 (12)	0.0369 (12)	0.0510 (12)	0.0015 (9)	0.0118 (9)	0.0027 (10)
C9	0.0380 (11)	0.0397 (12)	0.0395 (10)	−0.0029 (9)	0.0069 (8)	0.0030 (9)
C10	0.0423 (12)	0.0394 (12)	0.0568 (13)	−0.0086 (10)	0.0158 (10)	0.0021 (10)
C11	0.0465 (13)	0.0411 (13)	0.0597 (13)	−0.0033 (10)	0.0146 (10)	−0.0030 (11)
C12	0.0354 (12)	0.082 (2)	0.0635 (15)	−0.0020 (12)	0.0175 (10)	0.0022 (14)
C13	0.0407 (12)	0.0381 (12)	0.0628 (14)	0.0024 (10)	0.0105 (10)	0.0025 (11)
C14	0.0423 (12)	0.0450 (14)	0.0648 (14)	−0.0072 (10)	0.0114 (10)	0.0062 (11)
C15	0.0482 (14)	0.0476 (14)	0.0710 (16)	−0.0131 (11)	0.0179 (11)	0.0094 (12)
C16	0.0498 (14)	0.0390 (13)	0.0807 (17)	−0.0032 (11)	0.0209 (12)	0.0096 (12)
C17	0.0336 (10)	0.0283 (10)	0.0386 (10)	−0.0002 (8)	0.0004 (8)	−0.0022 (8)
C18	0.0456 (12)	0.0398 (12)	0.0358 (10)	0.0006 (9)	0.0050 (8)	0.0006 (9)
C19	0.0521 (13)	0.0468 (13)	0.0374 (10)	0.0054 (10)	−0.0070 (9)	−0.0005 (10)
C20	0.0391 (11)	0.0334 (11)	0.0517 (12)	0.0025 (9)	−0.0084 (9)	−0.0011 (10)
C21	0.0458 (13)	0.0534 (15)	0.0688 (15)	0.0015 (11)	−0.0197 (12)	−0.0015 (12)
C22	0.0343 (12)	0.0618 (17)	0.098 (2)	−0.0072 (12)	−0.0126 (13)	0.0035 (15)
C23	0.0341 (10)	0.0322 (10)	0.0359 (9)	−0.0023 (8)	0.0008 (7)	0.0015 (8)
C24	0.0341 (10)	0.0308 (10)	0.0449 (11)	−0.0008 (8)	−0.0004 (8)	0.0015 (9)
C25	0.0386 (12)	0.0463 (13)	0.0581 (13)	−0.0033 (10)	0.0036 (10)	0.0060 (11)
C26	0.0391 (13)	0.0583 (17)	0.089 (2)	−0.0074 (11)	0.0099 (12)	0.0050 (14)

S1—O2	1.4408 (17)	C10—H10	0.9300
S1—O4	1.4425 (17)	C11—H11	0.9300
S1—O3	1.4510 (16)	C12—H12A	0.9600
S1—C17	1.777 (2)	C12—H12B	0.9600
O1—C3	1.371 (3)	C12—H12C	0.9600
O1—C2	1.396 (3)	C13—C14	1.390 (3)
N1—C15	1.333 (3)	C13—H13	0.9300
N1—C11	1.346 (3)	C14—H14	0.9300
N1—C12	1.470 (3)	C15—C16	1.362 (3)
C1—C2	1.512 (3)	C15—H15	0.9300
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C23	1.367 (3)
C1—H1C	0.9600	C17—C18	1.413 (3)
C2—H2A	0.9700	C18—C19	1.359 (3)
C2—H2B	0.9700	C18—H18	0.9300
C3—C4	1.375 (3)	C19—C20	1.412 (3)
C3—C14	1.382 (3)	C19—H19	0.9300
C4—C5	1.371 (3)	C20—C21	1.415 (3)
C4—H4	0.9300	C20—C24	1.420 (3)
C5—C6	1.399 (3)	C21—C22	1.368 (4)
C5—H5	0.9300	C21—H21	0.9300
C6—C13	1.387 (3)	C22—C26	1.392 (4)
C6—C7	1.451 (3)	C22—H22	0.9300
C7—C8	1.329 (3)	C23—C24	1.423 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.457 (3)	C24—C25	1.420 (3)
C8—H8	0.9300	C25—C26	1.365 (3)
C9—C16	1.391 (3)	C25—H25	0.9300
C9—C10	1.393 (3)	C26—H26	0.9300
C10—C11	1.364 (3)

O2—S1—O4	113.52 (11)	N1—C12—H12A	109.5
O2—S1—O3	113.19 (10)	N1—C12—H12B	109.5
O4—S1—O3	112.62 (11)	H12A—C12—H12B	109.5
O2—S1—C17	105.67 (10)	N1—C12—H12C	109.5
O4—S1—C17	105.23 (10)	H12A—C12—H12C	109.5
O3—S1—C17	105.68 (9)	H12B—C12—H12C	109.5
C3—O1—C2	117.9 (2)	C6—C13—C14	121.6 (2)
C15—N1—C11	119.78 (19)	C6—C13—H13	119.2
C15—N1—C12	120.4 (2)	C14—C13—H13	119.2
C11—N1—C12	119.9 (2)	C3—C14—C13	119.5 (2)
C2—C1—H1A	109.5	C3—C14—H14	120.2
C2—C1—H1B	109.5	C13—C14—H14	120.2
H1A—C1—H1B	109.5	N1—C15—C16	121.0 (2)
C2—C1—H1C	109.5	N1—C15—H15	119.5
H1A—C1—H1C	109.5	C16—C15—H15	119.5
H1B—C1—H1C	109.5	C15—C16—C9	121.3 (2)
O1—C2—C1	106.8 (2)	C15—C16—H16	119.4
O1—C2—H2A	110.4	C9—C16—H16	119.4
C1—C2—H2A	110.4	C23—C17—C18	120.35 (18)
O1—C2—H2B	110.4	C23—C17—S1	122.14 (15)
C1—C2—H2B	110.4	C18—C17—S1	117.46 (15)
H2A—C2—H2B	108.6	C19—C18—C17	120.31 (19)
O1—C3—C4	114.7 (2)	C19—C18—H18	119.8
O1—C3—C14	125.7 (2)	C17—C18—H18	119.8
C4—C3—C14	119.5 (2)	C18—C19—C20	120.97 (19)
C5—C4—C3	120.9 (2)	C18—C19—H19	119.5
C5—C4—H4	119.5	C20—C19—H19	119.5
C3—C4—H4	119.5	C19—C20—C21	122.6 (2)
C4—C5—C6	121.0 (2)	C19—C20—C24	119.10 (18)
C4—C5—H5	119.5	C21—C20—C24	118.3 (2)
C6—C5—H5	119.5	C22—C21—C20	121.3 (2)
C13—C6—C5	117.5 (2)	C22—C21—H21	119.4
C13—C6—C7	119.0 (2)	C20—C21—H21	119.4
C5—C6—C7	123.6 (2)	C21—C22—C26	120.0 (2)
C8—C7—C6	127.4 (2)	C21—C22—H22	120.0
C8—C7—H7	116.3	C26—C22—H22	120.0
C6—C7—H7	116.3	C17—C23—C24	120.52 (17)
C7—C8—C9	124.2 (2)	C17—C23—H23	119.7
C7—C8—H8	117.9	C24—C23—H23	119.7
C9—C8—H8	117.9	C25—C24—C20	119.16 (19)
C16—C9—C10	116.0 (2)	C25—C24—C23	122.15 (18)
C16—C9—C8	120.3 (2)	C20—C24—C23	118.69 (18)
C10—C9—C8	123.65 (19)	C26—C25—C24	120.2 (2)
C11—C10—C9	120.9 (2)	C26—C25—H25	119.9
C11—C10—H10	119.6	C24—C25—H25	119.9
C9—C10—H10	119.6	C25—C26—C22	121.2 (2)
N1—C11—C10	121.0 (2)	C25—C26—H26	119.4
N1—C11—H11	119.5	C22—C26—H26	119.4
C10—C11—H11	119.5

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O3	0.93	2.54	2.912 (2)	105
C10—H10···O3ⁱ	0.93	2.52	3.433 (3)	168
C11—H11···O3ⁱⁱ	0.93	2.42	3.323 (3)	165
C12—H12B···O4ⁱⁱ	0.96	2.58	3.488 (3)	159
C15—H15···O2ⁱⁱⁱ	0.93	2.31	3.189 (3)	158
C25—H25···O3^iv	0.93	2.45	3.323 (3)	156
C14—H14···Cg1^v	0.93	2.84	3.686 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3ⁱ	0.93	2.52	3.433 (3)	168
C11—H11⋯O3ⁱⁱ	0.93	2.42	3.323 (3)	165
C12—H12B⋯O4ⁱⁱ	0.96	2.58	3.488 (3)	159
C15—H15⋯O2ⁱⁱⁱ	0.93	2.31	3.189 (3)	158
C25—H25⋯O3^iv	0.93	2.45	3.323 (3)	156
C14—H14⋯Cg1^v	0.93	2.84	3.686 (3)	152

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 4-(3-Eth-oxy-4-hydroxy-styr-yl)-1-methyl-pyridinium tosyl-ate monohydrate.

Authors: S Murugavel; A Subbiahpandi; C Srikanth; S Kalainathan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-12-10

2 in total