Literature DB >> 21580938

1-Methyl-4-[(E)-2-(2-thien-yl)-ethen-yl]-pyridinium 4-methyl-benzene-sulfonate.

Suchada Chantrapromma, Pumsak Ruanwas, Hoong-Kun Fun, Chatchanok Karalai.   

Abstract

In the title compound, C(12)H(12)NS(+)·C(7)H(7)O(3)S(-), the cation exists in an E configuration with respect to the ethenyl C=C bond. The cation is essentially planar with a dihedral angle of 1.94 (10)° between the pyridinium and thio-phene rings. The benzene ring of the anion makes dihedral angles of 75.23 (10) and 76.83 (10)°, respectively, with the pyridinium and thio-phene rings. In the crystal structure, cations and anions form alternate layers parallel to the bc plane. Within each layer, both cations and anions are arranged into chains directed along the b axis. The cation chain and the anion chain are inter-connected by weak C-H⋯O inter-actions into a three-dimensional network. The crystal structure is further stabilized by C-H⋯π inter-actions.

Entities:  

Year:  2008        PMID： 21580938      PMCID： PMC2959609          DOI： 10.1107/S1600536808031401

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


Related literature

For bond lengths, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see, for example: Chantrapromma, Jindawong & Fun (2007 ▶); Chantrapromma, Jindawong, Fun & Patil (2007 ▶); Chantrapromma et al. (2008 ▶); Lakshmanaperumal et al. (2002 ▶, 2004 ▶); Rahman et al. (2003 ▶); Ruanwas et al. (2008 ▶); Usman et al. (2000 ▶, 2001 ▶).

Experimental

Crystal data

C12H12NS+·C7H7O3S− M = 373.49 Triclinic, a = 9.2947 (1) Å b = 9.6144 (1) Å c = 10.7790 (1) Å α = 87.817 (1)° β = 64.702 (1)° γ = 88.712 (1)° V = 870.21 (1) Å3 Z = 2 Mo Kα radiation μ = 0.32 mm−1 T = 100.0 (1) K 0.36 × 0.35 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.893, T max = 0.945 18024 measured reflections 4606 independent reflections 4122 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.148 S = 1.04 4606 reflections 228 parameters H-atom parameters constrained Δρmax = 0.98 e Å−3 Δρmin = −0.71 e Å−3 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, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031401/is2338sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031401/is2338Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H12NS+·C7H7O3S−Z = 2
Mr = 373.49F(000) = 392
Triclinic, P1Dx = 1.425 Mg m−3
Hall symbol: -P 1Melting point = 507–509 K
a = 9.2947 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6144 (1) ÅCell parameters from 4606 reflections
c = 10.7790 (1) Åθ = 2.4–29.0°
α = 87.817 (1)°µ = 0.32 mm−1
β = 64.702 (1)°T = 100 K
γ = 88.712 (1)°Block, yellow
V = 870.21 (2) Å30.36 × 0.35 × 0.18 mm
Bruker SMART APEXII CCD area-detector diffractometer4606 independent reflections
Radiation source: fine-focus sealed tube4122 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 29.0°, θmin = 2.4°
ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −13→13
Tmin = 0.893, Tmax = 0.945l = −14→14
18024 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0809P)2 + 1.1333P] where P = (Fo2 + 2Fc2)/3
4606 reflections(Δ/σ)max = 0.001
228 parametersΔρmax = 0.98 e Å−3
0 restraintsΔρmin = −0.71 e Å−3
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.
xyzUiso*/Ueq
S10.15733 (7)0.99833 (6)0.16005 (6)0.02891 (16)
S20.55035 (5)0.58728 (4)0.20813 (4)0.01428 (13)
O10.69298 (18)0.61236 (15)0.08113 (15)0.0220 (3)
O20.40517 (17)0.63620 (15)0.19977 (15)0.0194 (3)
O30.56449 (18)0.63482 (14)0.32920 (14)0.0196 (3)
N1−0.0092 (2)0.50151 (17)0.75333 (17)0.0169 (3)
C10.1573 (2)0.6066 (2)0.5395 (2)0.0221 (4)
H1A0.25740.61450.46620.026*
C20.1351 (2)0.5142 (2)0.6456 (2)0.0208 (4)
H2A0.21990.45970.64370.025*
C3−0.1335 (2)0.5809 (2)0.7588 (2)0.0195 (4)
H3A−0.23170.57210.83420.023*
C4−0.1159 (2)0.6742 (2)0.6539 (2)0.0206 (4)
H4A−0.20250.72790.65860.025*
C50.0314 (2)0.6894 (2)0.5397 (2)0.0196 (4)
C60.0632 (2)0.7841 (2)0.4220 (2)0.0220 (4)
H6A0.16430.78270.34970.026*
C7−0.0453 (3)0.8733 (2)0.4121 (2)0.0235 (4)
H7A−0.14610.87190.48490.028*
C8−0.0211 (3)0.9713 (2)0.2998 (2)0.0225 (4)
C9−0.1401 (2)1.0515 (2)0.29383 (19)0.0151 (3)
H9A−0.24541.04890.35910.018*
C10−0.0793 (3)1.1440 (2)0.1689 (2)0.0247 (4)
H10A−0.14171.20860.14740.030*
C110.0787 (3)1.1230 (2)0.0896 (2)0.0262 (4)
H11A0.13671.17090.00700.031*
C12−0.0343 (3)0.3981 (2)0.8657 (2)0.0241 (4)
H12A0.06490.37950.87100.036*
H12B−0.07400.31340.84790.036*
H12C−0.10990.43410.95100.036*
C130.4960 (2)0.1137 (2)0.2619 (2)0.0178 (4)
C140.5220 (2)0.1820 (2)0.1374 (2)0.0179 (4)
H14A0.52730.13030.06430.021*
C150.5401 (2)0.3257 (2)0.12029 (19)0.0161 (3)
H15A0.55730.36940.03670.019*
C160.5323 (2)0.40335 (18)0.22945 (18)0.0141 (3)
C170.5046 (2)0.33792 (19)0.35510 (19)0.0158 (3)
H17A0.49830.38990.42830.019*
C180.4864 (2)0.1940 (2)0.3702 (2)0.0174 (4)
H18A0.46740.15050.45430.021*
C190.4833 (3)−0.0423 (2)0.2771 (3)0.0260 (4)
H19A0.3967−0.06750.36320.039*
H19B0.5807−0.08090.27440.039*
H19C0.4644−0.07790.20340.039*
U11U22U33U12U13U23
S10.0231 (3)0.0296 (3)0.0285 (3)0.0008 (2)−0.0063 (2)0.0060 (2)
S20.0174 (2)0.0119 (2)0.0122 (2)0.00110 (15)−0.00523 (17)0.00122 (15)
O10.0223 (7)0.0188 (7)0.0167 (7)−0.0017 (5)−0.0007 (6)0.0020 (5)
O20.0224 (7)0.0171 (6)0.0200 (7)0.0047 (5)−0.0105 (6)0.0004 (5)
O30.0284 (7)0.0151 (6)0.0183 (7)0.0020 (5)−0.0129 (6)−0.0014 (5)
N10.0175 (7)0.0161 (7)0.0172 (7)0.0001 (6)−0.0076 (6)−0.0002 (6)
C10.0187 (9)0.0242 (10)0.0180 (9)−0.0016 (7)−0.0028 (7)−0.0009 (7)
C20.0163 (8)0.0210 (9)0.0229 (10)0.0035 (7)−0.0062 (7)−0.0033 (7)
C30.0150 (8)0.0234 (9)0.0190 (9)0.0000 (7)−0.0061 (7)−0.0007 (7)
C40.0182 (9)0.0221 (9)0.0235 (10)0.0023 (7)−0.0112 (8)0.0002 (7)
C50.0252 (9)0.0169 (9)0.0181 (9)−0.0040 (7)−0.0104 (8)0.0005 (7)
C60.0215 (9)0.0222 (10)0.0205 (9)−0.0015 (7)−0.0074 (8)0.0003 (7)
C70.0218 (9)0.0251 (10)0.0218 (10)−0.0018 (8)−0.0077 (8)0.0010 (8)
C80.0275 (10)0.0195 (9)0.0225 (10)−0.0024 (8)−0.0127 (8)0.0015 (7)
C90.0091 (7)0.0229 (9)0.0135 (8)0.0019 (6)−0.0051 (6)−0.0011 (7)
C100.0281 (10)0.0218 (10)0.0280 (11)−0.0013 (8)−0.0162 (9)0.0061 (8)
C110.0295 (11)0.0243 (10)0.0242 (10)−0.0038 (8)−0.0115 (9)0.0076 (8)
C120.0322 (11)0.0195 (9)0.0224 (10)−0.0001 (8)−0.0137 (9)0.0034 (8)
C130.0158 (8)0.0145 (8)0.0243 (9)0.0013 (6)−0.0098 (7)0.0004 (7)
C140.0181 (8)0.0169 (9)0.0187 (9)0.0016 (7)−0.0079 (7)−0.0030 (7)
C150.0167 (8)0.0172 (9)0.0139 (8)0.0014 (6)−0.0061 (7)0.0001 (6)
C160.0147 (8)0.0123 (8)0.0141 (8)0.0012 (6)−0.0051 (6)0.0004 (6)
C170.0172 (8)0.0160 (8)0.0142 (8)0.0013 (6)−0.0069 (7)0.0007 (6)
C180.0172 (8)0.0165 (9)0.0190 (9)0.0000 (6)−0.0086 (7)0.0043 (7)
C190.0313 (11)0.0141 (9)0.0367 (12)−0.0006 (8)−0.0186 (10)0.0020 (8)
S1—C111.707 (2)C9—C101.484 (3)
S1—C81.715 (2)C9—H9A0.9300
S2—O21.4569 (15)C10—C111.362 (3)
S2—O31.4574 (14)C10—H10A0.9300
S2—O11.4587 (14)C11—H11A0.9300
S2—C161.7769 (18)C12—H12A0.9600
N1—C31.351 (2)C12—H12B0.9600
N1—C21.352 (3)C12—H12C0.9600
N1—C121.479 (3)C13—C181.394 (3)
C1—C21.367 (3)C13—C141.398 (3)
C1—C51.400 (3)C13—C191.504 (3)
C1—H1A0.9300C14—C151.391 (3)
C2—H2A0.9300C14—H14A0.9300
C3—C41.371 (3)C15—C161.393 (3)
C3—H3A0.9300C15—H15A0.9300
C4—C51.403 (3)C16—C171.393 (3)
C4—H4A0.9300C17—C181.393 (3)
C5—C61.458 (3)C17—H17A0.9300
C6—C71.346 (3)C18—H18A0.9300
C6—H6A0.9300C19—H19A0.9600
C7—C81.447 (3)C19—H19B0.9600
C7—H7A0.9300C19—H19C0.9600
C8—C91.357 (3)
C11—S1—C892.72 (11)C11—C10—C9112.07 (19)
O2—S2—O3112.96 (8)C11—C10—H10A124.0
O2—S2—O1113.06 (9)C9—C10—H10A124.0
O3—S2—O1113.19 (9)C10—C11—S1111.84 (17)
O2—S2—C16105.46 (9)C10—C11—H11A124.1
O3—S2—C16105.73 (9)S1—C11—H11A124.1
O1—S2—C16105.54 (8)N1—C12—H12A109.5
C3—N1—C2120.63 (17)N1—C12—H12B109.5
C3—N1—C12118.95 (17)H12A—C12—H12B109.5
C2—N1—C12120.41 (17)N1—C12—H12C109.5
C2—C1—C5120.85 (18)H12A—C12—H12C109.5
C2—C1—H1A119.6H12B—C12—H12C109.5
C5—C1—H1A119.6C18—C13—C14118.08 (18)
N1—C2—C1120.52 (18)C18—C13—C19121.03 (18)
N1—C2—H2A119.7C14—C13—C19120.87 (18)
C1—C2—H2A119.7C15—C14—C13121.46 (18)
N1—C3—C4120.49 (18)C15—C14—H14A119.3
N1—C3—H3A119.8C13—C14—H14A119.3
C4—C3—H3A119.8C14—C15—C16119.38 (17)
C3—C4—C5120.62 (18)C14—C15—H15A120.3
C3—C4—H4A119.7C16—C15—H15A120.3
C5—C4—H4A119.7C15—C16—C17120.27 (17)
C1—C5—C4116.87 (18)C15—C16—S2119.07 (14)
C1—C5—C6117.82 (18)C17—C16—S2120.61 (14)
C4—C5—C6125.30 (19)C16—C17—C18119.45 (17)
C7—C6—C5123.75 (19)C16—C17—H17A120.3
C7—C6—H6A118.1C18—C17—H17A120.3
C5—C6—H6A118.1C17—C18—C13121.35 (18)
C6—C7—C8126.6 (2)C17—C18—H18A119.3
C6—C7—H7A116.7C13—C18—H18A119.3
C8—C7—H7A116.7C13—C19—H19A109.5
C9—C8—C7122.8 (2)C13—C19—H19B109.5
C9—C8—S1112.58 (16)H19A—C19—H19B109.5
C7—C8—S1124.57 (17)C13—C19—H19C109.5
C8—C9—C10110.76 (17)H19A—C19—H19C109.5
C8—C9—H9A124.6H19B—C19—H19C109.5
C10—C9—H9A124.6
C3—N1—C2—C1−0.7 (3)C8—C9—C10—C111.8 (3)
C12—N1—C2—C1177.87 (19)C9—C10—C11—S1−0.7 (3)
C5—C1—C2—N1−0.3 (3)C8—S1—C11—C10−0.32 (19)
C2—N1—C3—C41.0 (3)C18—C13—C14—C150.9 (3)
C12—N1—C3—C4−177.58 (19)C19—C13—C14—C15−177.44 (18)
N1—C3—C4—C5−0.3 (3)C13—C14—C15—C160.0 (3)
C2—C1—C5—C40.9 (3)C14—C15—C16—C17−0.8 (3)
C2—C1—C5—C6−179.05 (19)C14—C15—C16—S2−178.34 (14)
C3—C4—C5—C1−0.6 (3)O2—S2—C16—C1569.43 (16)
C3—C4—C5—C6179.3 (2)O3—S2—C16—C15−170.67 (14)
C1—C5—C6—C7−177.1 (2)O1—S2—C16—C15−50.48 (17)
C4—C5—C6—C73.0 (3)O2—S2—C16—C17−108.10 (16)
C5—C6—C7—C8178.9 (2)O3—S2—C16—C1711.80 (18)
C6—C7—C8—C9175.6 (2)O1—S2—C16—C17131.99 (16)
C6—C7—C8—S1−3.7 (3)C15—C16—C17—C180.7 (3)
C11—S1—C8—C91.40 (18)S2—C16—C17—C18178.16 (14)
C11—S1—C8—C7−179.3 (2)C16—C17—C18—C130.3 (3)
C7—C8—C9—C10178.64 (19)C14—C13—C18—C17−1.0 (3)
S1—C8—C9—C10−2.0 (2)C19—C13—C18—C17177.30 (18)
D—H···AD—HH···AD···AD—H···A
C2—H2A···O3i0.932.313.219 (3)166
C3—H3A···O1ii0.932.493.168 (2)130
C6—H6A···O20.932.563.378 (3)147
C11—H11A···O1iii0.932.543.303 (3)139
C12—H12A···O1i0.962.523.455 (3)165
C12—H12C···O1ii0.962.473.341 (3)151
C15—H15A···O2iv0.932.423.272 (2)152
C17—H17A···O3i0.932.433.202 (2)141
C4—H4A···Cg1v0.932.623.431 (2)145
C10—H10A···Cg1vi0.932.953.666 (3)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2A⋯O3i0.932.313.219 (3)166
C3—H3A⋯O1ii0.932.493.168 (2)130
C6—H6A⋯O20.932.563.378 (3)147
C11—H11A⋯O1iii0.932.543.303 (3)139
C12—H12A⋯O1i0.962.523.455 (3)165
C12—H12C⋯O1ii0.962.473.341 (3)151
C15—H15A⋯O2iv0.932.423.272 (2)152
C17—H17A⋯O3i0.932.433.202 (2)141
C4—H4A⋯Cg1v0.932.623.431 (2)145
C10—H10A⋯Cg1vi0.932.953.666 (3)135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C13–C18 benzene ring.

  3 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.  1-Methyl-2-[(E)-2-(2-thien-yl)ethen-yl]quinolinium iodide.

Authors:  Pumsak Ruanwas; Thawanrat Kobkeatthawin; Suchada Chantrapromma; Hoong-Kun Fun; Chatchanok Karalai
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-07-09

3.  1-Methyl-4-[(E)-2-(2-thien-yl)ethen-yl]pyridinium 4-chloro-benzene-sulfonate.

Authors:  Suchada Chantrapromma; Chotika Laksana; Pumsak Ruanwas; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-13
  3 in total

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