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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o574–o575.
Published online 2008 February 13. doi:  10.1107/S1600536808003929
PMCID: PMC2960744

1-Methyl-4-[(E)-2-(2-thien­yl)ethen­yl]pyridinium 4-chloro­benzene­sulfonate1

Abstract

In the title compound, C12H12NS+·C6H4ClO3S, the cation is almost planar and exists in the E configuration. The cations and anions form alternate layers parallel to the ab plane. Within each layer, both cations and anions form chains directed along the b axis. The mol­ecules are inter­connected by weak C—H(...)O inter­actions into a three-dimensional network. The crystal structure is further stabilized by C—H(...)π inter­actions involving the thio­phene ring. The sulfonate and thio­phene groups are involved in weak intra­molecular C—H(...)O and C—H(...)S inter­actions, respectively. The latter intra­molecular hydrogen bonds produce S(5) ring motifs.

Related literature

For bond lengths and angles, see Allen (2002 [triangle]); Allen et al. (1987 [triangle]). For related literature on hydrogen-bond motifs, see Bernstein et al. (1995 [triangle]). For related structures, see for example Chantrapromma et al. (2005 [triangle], 2006a [triangle],b [triangle], 2007a [triangle],b [triangle],c [triangle],d [triangle]); Drost et al. (1995 [triangle]); Jindawong et al. (2005 [triangle]); Subramaniyan et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o574-scheme1.jpg

Experimental

Crystal data

  • C12H12NS+·C6H4ClO3S
  • M r = 393.91
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o574-efi1.jpg
  • a = 7.3532 (1) Å
  • b = 14.0250 (2) Å
  • c = 18.3755 (2) Å
  • β = 111.232 (1)°
  • V = 1766.41 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.47 mm−1
  • T = 100.0 (1) K
  • 0.49 × 0.22 × 0.18 mm

Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.883, T max = 0.919
  • 23692 measured reflections
  • 4688 independent reflections
  • 3913 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.094
  • S = 1.06
  • 4688 reflections
  • 227 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003929/fb2086sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003929/fb2086Isup2.hkl

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

Acknowledgments

The authors thank the Prince of Songkla University for the research grant. PR thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors also thank the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) No. 304/PFIZIK/653003/A118.

supplementary crystallographic information

Comment

Molecules with extended π systems have been extensively used in attempts to obtain materials with non-linear optical (NLO) properties. Organic crystal with the required conjugated π electrons are attractive candidates because of the large NLO coefficients. In our research for second-order NLO materials, we have previously synthesized and crystallized several organic ionic salts of pyridinium and quinolinium derivatives to study their non-linear optical properties (Chantrapromma et al., 2005; 2006a; 2006b; 2007a; 2007b; 2007c; 2007 d; Jindawong et al., 2005). An earlier study carried out by Drost et al. (1995) has revealed that the products of the dipole moment and the molecular hyperpolarizability (β) of thiophene-containing conjugated moieties are larger than those of the phenyl analogues. Based on this reason, we have synthesized the title compound which was designed by replacement of the cationic phenyl ring by the thiophene ring that is present in 4-(4'-Hydroxy-3'-methoxystyryl)-1-methylpyridinium 4-chlorobenzenesulfonate (Chantrapromma et al., 2005).

The asymmetric unit of the title compound consists of the C12H12NS+ cation and the C6H4ClO3S- anion. The cation is almost planar and exists in the E configuration with respect to the C6?C7 double bond [1.334 (3) Å]. The cation is almost perpendicular to the anion as is indicated by the angles between the mean planes of the chlorophenyl ring to the pyridinium as well as to the thiophene ring being 87.64 (9)° and 86.73 (9)°, respectively. The dihedral angle between the pyridinium and the thiophene rings is 5.74 (10)°. The ethenyl unit is nearly planar. The torsion angles C4–C5–C6–C7 = -4.3 (3)° and C6–C7–C8–S1 = -1.5 (3)°.

The atom O3 of the sulfonate and the S atom of the thiophene contribute to the C—H···O and C—H···S intramolecular weak interactions (Fig. 1 and Table 1) forming S(5) ring motifs (Bernstein et al., 1995). The bond lengths and angles are normal (Allen et al., 1987) and are comparable with closely related structures (Chantrapromma et al., 2005; 2006b; 2007c; 2007 d).

All the O atoms of 4-chlorobenzenesulfonate anion are involved in the C—H···O weak interactions (Table 1). The cations and anions form alternate layers parallel to the ab plane. Within each respective layer, the ions are interconnected by C—H···O weak interactions and in each respective layer can be distinguished chains directed along the b axis. The alternating layers are separated by 4.282 (2) Å and are further linked into a three dimensional network by C—H···O weak interactions (Table 1). The sulfonate as well as the thiophene are involved in C—H···O and C—H···S intramolecular weak interactions, respectively. These weak hydrogen bonds participate in S(5) ring motifs. The crystal structure is further stabilized by the C12—H12B···π interaction to the thiophene ring C8–C11/S1: C12—H12B=0.96; H12B···Cg1i=2.692; C12—Cg1i=3.515 (2) Å; C12—H12B···Cg1i= 144°. [Cg1i is the centroid of the S1/C8–C11 thiophene ring (symmetry code: (i): 2 - x, 2 - y, 1 - z).]

A very interesting feature is the short non-bonding contact between Cl1 and O3 that is 2.963 (1) Å long only. A search in the Cambridge Structural Database (version 5.29 and addenda up to 25-th January 2008; Allen, 2002) among the structures which have been flagged with no error or disorder as well as with R-factor < 0.05 and which contained chloro-phenyl with any substituent in the para position showed that the present structure contains an unprecedentedly short contact of this kind. The up-to-now shortest contact of this type was 2.996 (2) Å long and it was observed in MUTDOU [Spiro(2-carbomethoxy-3-(4-chlorophenyl)-5-(S,R)-(cis-1-(4-methoxyphenyl) -3-phenyl-4-oxoazetidin-2-(S,R)-yl)pyrrolidine-4,31-chroman-41-one)] determined by Subramaniyan et al. (2003).

Experimental

4-(2-Thiophenestyryl)-1-methylpyridinium iodide (compound A) was synthesized by mixing a solution (1:1:1 molar ratio) of 1,4-dimethylpyridinium iodide (2.00 g, 8.5 mmol), 2-thiophenecarboxaldehyde (6.00 ml, 8.5 mmol) and piperidine (0.84 ml, 8.5 mmol) in hot methanol (40 ml). The resulting solution was refluxed for 5 h under a nitrogen atmosphere. The resultant solid was filtered off, washed with diethyl ether and recrystallized from methanol. The title compound was synthesized by mixing compound A (0.10 g, 0.3 mmol) in hot methanol (20 ml) and silver(I) 4-chlorobenzenesulfonate (0.08 g, 0.3 mmol) in hot methanol (30 ml). Silver(I) 4-chlorobenzenesulfonate was synthesized according to our previously reported procedure (Chantrapromma et al., 2006b). The mixture immediately yielded a grey solid of silver iodide. After stirring the mixture for ca 30 min, the precipitate of silver iodide was removed and the resulting solution was evaporated and a brown solid was obtained. Brown block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol solvent by slow evaporation of the solvent at room temperature after several days (Mp. 503–505 K).

Refinement

All the hydrogen atoms could have been discerned in the difference Fourier map. Nevertheless, all the H atoms attached to the carbon atoms were constrained in a riding motion approximation with Caryl—H=0.93 and Cmethyl—H=0.968 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.75 Å from C8 and the deepest hole is located at 0.50 Å from S1.

Figures

Fig. 1.
The title molecules showing 50% probability displacement ellipsoids and the atom-numbering scheme. The intramolecular C—H···O and C—H···S weak interactions are drawn as dashed lines.
Fig. 2.
The packing diagram of the title structure viewed along the a axis. The weak C—H···O and C—H···S interactions are drawn as dashed lines.

Crystal data

C12H12NS+·C6H4ClO3SF000 = 816
Mr = 393.91Dx = 1.481 Mg m3
Monoclinic, P21/cMelting point = 503–505 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 7.3532 (1) ÅCell parameters from 4688 reflections
b = 14.0250 (2) Åθ = 1.9–29.0º
c = 18.3755 (2) ŵ = 0.47 mm1
β = 111.232 (1)ºT = 100.0 (1) K
V = 1766.41 (4) Å3Block, brown
Z = 40.49 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer4688 independent reflections
Radiation source: fine-focus sealed tube3913 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
Detector resolution: 8.33 pixels mm-1θmax = 29.0º
T = 100.0(1) Kθmin = 1.9º
ω scansh = −10→10
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −19→19
Tmin = 0.883, Tmax = 0.919l = −21→25
23692 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.094  w = 1/[σ2(Fo2) + (0.0415P)2 + 1.1208P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4688 reflectionsΔρmax = 0.57 e Å3
227 parametersΔρmin = −0.42 e Å3
63 constraintsExtinction correction: none
Primary atom site location: difference Fourier map

Special details

Experimental. The low-temparture data was collected with the Oxford Cryosystem 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.57131 (7)0.72654 (3)0.43805 (3)0.02450 (11)
S21.05267 (5)0.60506 (3)0.27447 (2)0.01477 (10)
Cl10.37650 (6)0.31936 (3)0.25045 (2)0.02092 (10)
O11.09007 (17)0.58763 (9)0.20315 (7)0.0219 (3)
O21.21870 (16)0.58102 (9)0.34443 (7)0.0196 (3)
O30.97435 (17)0.69943 (8)0.27824 (7)0.0210 (3)
N10.8323 (2)1.24164 (11)0.49389 (9)0.0214 (3)
C10.6981 (3)1.10669 (14)0.41625 (11)0.0273 (4)
H1A0.63421.08080.36690.033*
C20.7408 (3)1.20156 (14)0.42351 (11)0.0265 (4)
H2A0.70601.23940.37900.032*
C30.8863 (3)1.18711 (14)0.55895 (11)0.0259 (4)
H3A0.95011.21500.60750.031*
C40.8481 (3)1.09132 (14)0.55424 (11)0.0267 (4)
H4A0.88811.05470.59950.032*
C50.7490 (2)1.04783 (13)0.48184 (11)0.0216 (3)
C60.6999 (3)0.94698 (14)0.47236 (11)0.0239 (4)
H6A0.62620.92520.42260.029*
C70.7537 (3)0.88364 (13)0.53044 (11)0.0227 (4)
H7A0.82680.90660.57990.027*
C80.7098 (2)0.78300 (13)0.52426 (10)0.0213 (3)
C90.7700 (2)0.72058 (12)0.58541 (10)0.0190 (3)
H9A0.84510.73790.63630.023*
C100.7037 (3)0.62467 (13)0.56186 (11)0.0234 (4)
H10A0.73130.57300.59580.028*
C110.5956 (3)0.61854 (13)0.48386 (11)0.0234 (4)
H11A0.54150.56220.45860.028*
C120.8779 (3)1.34470 (13)0.50102 (12)0.0287 (4)
H12A0.81191.37540.45180.043*
H12B1.01611.35350.51590.043*
H12C0.83531.37220.54000.043*
C130.8648 (2)0.52345 (12)0.27171 (9)0.0151 (3)
C140.8824 (2)0.42781 (12)0.25482 (9)0.0165 (3)
H14A0.99440.40670.24750.020*
C150.7332 (2)0.36386 (12)0.24892 (10)0.0174 (3)
H15A0.74340.30000.23720.021*
C160.5682 (2)0.39778 (12)0.26093 (9)0.0165 (3)
C170.5512 (2)0.49151 (12)0.28055 (10)0.0186 (3)
H17A0.44170.51200.29020.022*
C180.7013 (2)0.55480 (12)0.28563 (10)0.0181 (3)
H18A0.69200.61830.29840.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0255 (2)0.0248 (2)0.0196 (2)−0.00284 (17)0.00382 (17)0.00120 (17)
S20.01233 (18)0.01553 (19)0.01604 (19)0.00021 (14)0.00465 (14)0.00095 (14)
Cl10.01861 (19)0.0189 (2)0.0272 (2)−0.00466 (14)0.01069 (16)−0.00201 (16)
O10.0200 (6)0.0292 (7)0.0181 (6)−0.0020 (5)0.0090 (5)0.0007 (5)
O20.0144 (5)0.0239 (6)0.0174 (6)0.0000 (4)0.0022 (5)0.0013 (5)
O30.0181 (6)0.0143 (6)0.0314 (7)−0.0003 (4)0.0099 (5)0.0002 (5)
N10.0225 (7)0.0214 (7)0.0240 (8)−0.0001 (6)0.0127 (6)0.0011 (6)
C10.0289 (9)0.0304 (10)0.0204 (9)−0.0058 (8)0.0063 (7)−0.0019 (7)
C20.0298 (10)0.0285 (10)0.0192 (8)−0.0031 (8)0.0066 (7)0.0034 (7)
C30.0309 (9)0.0293 (10)0.0174 (8)−0.0016 (8)0.0085 (7)−0.0019 (7)
C40.0329 (10)0.0273 (10)0.0208 (9)0.0009 (8)0.0108 (8)0.0035 (7)
C50.0192 (8)0.0227 (9)0.0256 (9)−0.0001 (6)0.0114 (7)−0.0001 (7)
C60.0219 (8)0.0285 (9)0.0209 (8)−0.0034 (7)0.0073 (7)−0.0016 (7)
C70.0192 (8)0.0274 (9)0.0224 (9)0.0001 (7)0.0086 (7)−0.0019 (7)
C80.0181 (8)0.0239 (9)0.0227 (8)−0.0015 (6)0.0085 (7)−0.0015 (7)
C90.0176 (8)0.0251 (9)0.0133 (7)−0.0012 (6)0.0045 (6)0.0008 (6)
C100.0219 (8)0.0249 (9)0.0220 (9)−0.0019 (7)0.0061 (7)0.0044 (7)
C110.0225 (8)0.0211 (9)0.0242 (9)−0.0038 (7)0.0058 (7)0.0004 (7)
C120.0318 (10)0.0219 (9)0.0376 (11)−0.0020 (8)0.0186 (9)−0.0005 (8)
C130.0139 (7)0.0171 (8)0.0142 (7)−0.0002 (6)0.0048 (6)−0.0002 (6)
C140.0145 (7)0.0190 (8)0.0170 (8)0.0024 (6)0.0068 (6)−0.0008 (6)
C150.0186 (7)0.0148 (7)0.0192 (8)0.0016 (6)0.0075 (6)−0.0010 (6)
C160.0148 (7)0.0176 (8)0.0166 (7)−0.0027 (6)0.0051 (6)0.0008 (6)
C170.0148 (7)0.0180 (8)0.0249 (9)0.0018 (6)0.0094 (7)0.0001 (6)
C180.0182 (8)0.0148 (8)0.0217 (8)0.0011 (6)0.0078 (6)−0.0014 (6)

Geometric parameters (Å, °)

S1—C111.7105 (19)C7—C81.443 (3)
S1—C81.7335 (18)C7—H7A0.9300
S2—O11.4541 (12)C8—C91.366 (2)
S2—O31.4550 (12)C9—C101.443 (2)
S2—O21.4560 (12)C9—H9A0.9300
S2—C131.7806 (16)C10—C111.367 (3)
Cl1—C161.7428 (16)C10—H10A0.9300
N1—C21.346 (2)C11—H11A0.9300
N1—C31.352 (2)C12—H12A0.9600
N1—C121.479 (2)C12—H12B0.9600
C1—C21.363 (3)C12—H12C0.9600
C1—C51.395 (3)C13—C181.388 (2)
C1—H1A0.9300C13—C141.393 (2)
C2—H2A0.9300C14—C151.390 (2)
C3—C41.369 (3)C14—H14A0.9300
C3—H3A0.9300C15—C161.393 (2)
C4—C51.404 (3)C15—H15A0.9300
C4—H4A0.9300C16—C171.381 (2)
C5—C61.455 (3)C17—C181.393 (2)
C6—C71.334 (3)C17—H17A0.9300
C6—H6A0.9300C18—H18A0.9300
C11—S1—C891.87 (9)C8—C9—C10112.16 (15)
O1—S2—O3113.77 (7)C8—C9—H9A123.9
O1—S2—O2112.64 (7)C10—C9—H9A123.9
O3—S2—O2112.86 (7)C11—C10—C9112.22 (16)
O1—S2—C13105.32 (7)C11—C10—H10A123.9
O3—S2—C13105.65 (7)C9—C10—H10A123.9
O2—S2—C13105.68 (7)C10—C11—S1112.19 (14)
C2—N1—C3119.87 (16)C10—C11—H11A123.9
C2—N1—C12120.78 (16)S1—C11—H11A123.9
C3—N1—C12119.34 (16)N1—C12—H12A109.5
C2—C1—C5120.86 (18)N1—C12—H12B109.5
C2—C1—H1A119.6H12A—C12—H12B109.5
C5—C1—H1A119.6N1—C12—H12C109.5
N1—C2—C1121.28 (17)H12A—C12—H12C109.5
N1—C2—H2A119.4H12B—C12—H12C109.5
C1—C2—H2A119.4C18—C13—C14120.17 (15)
N1—C3—C4120.76 (17)C18—C13—S2120.39 (13)
N1—C3—H3A119.6C14—C13—S2119.44 (12)
C4—C3—H3A119.6C15—C14—C13120.28 (15)
C3—C4—C5120.70 (17)C15—C14—H14A119.9
C3—C4—H4A119.6C13—C14—H14A119.9
C5—C4—H4A119.6C14—C15—C16118.36 (15)
C1—C5—C4116.51 (17)C14—C15—H15A120.8
C1—C5—C6119.63 (17)C16—C15—H15A120.8
C4—C5—C6123.86 (17)C17—C16—C15122.20 (15)
C7—C6—C5124.26 (17)C17—C16—Cl1118.91 (12)
C7—C6—H6A117.9C15—C16—Cl1118.89 (13)
C5—C6—H6A117.9C16—C17—C18118.65 (15)
C6—C7—C8126.54 (17)C16—C17—H17A120.7
C6—C7—H7A116.7C18—C17—H17A120.7
C8—C7—H7A116.7C13—C18—C17120.27 (15)
C9—C8—C7124.44 (16)C13—C18—H18A119.9
C9—C8—S1111.55 (13)C17—C18—H18A119.9
C7—C8—S1124.01 (14)
C3—N1—C2—C11.0 (3)C8—C9—C10—C11−0.1 (2)
C12—N1—C2—C1179.98 (18)C9—C10—C11—S1−0.2 (2)
C5—C1—C2—N1−0.3 (3)C8—S1—C11—C100.36 (15)
C2—N1—C3—C4−0.4 (3)O1—S2—C13—C18−130.91 (14)
C12—N1—C3—C4−179.30 (17)O3—S2—C13—C18−10.19 (16)
N1—C3—C4—C5−1.1 (3)O2—S2—C13—C18109.65 (14)
C2—C1—C5—C4−1.0 (3)O1—S2—C13—C1448.59 (15)
C2—C1—C5—C6179.41 (18)O3—S2—C13—C14169.30 (13)
C3—C4—C5—C11.7 (3)O2—S2—C13—C14−70.85 (14)
C3—C4—C5—C6−178.76 (17)C18—C13—C14—C152.4 (2)
C1—C5—C6—C7175.16 (18)S2—C13—C14—C15−177.09 (12)
C4—C5—C6—C7−4.4 (3)C13—C14—C15—C16−0.5 (2)
C5—C6—C7—C8−179.72 (17)C14—C15—C16—C17−1.9 (3)
C6—C7—C8—C9179.23 (18)C14—C15—C16—Cl1177.84 (12)
C6—C7—C8—S1−1.5 (3)C15—C16—C17—C182.4 (3)
C11—S1—C8—C9−0.44 (14)Cl1—C16—C17—C18−177.33 (13)
C11—S1—C8—C7−179.82 (15)C14—C13—C18—C17−1.9 (2)
C7—C8—C9—C10179.78 (16)S2—C13—C18—C17177.59 (13)
S1—C8—C9—C100.40 (19)C16—C17—C18—C13−0.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···O3i0.932.313.211 (2)164
C6—H6A···S10.932.843.228 (2)106
C7—H7A···O1ii0.932.393.266 (2)157
C9—H9A···O3ii0.932.593.495 (2)166
C10—H10A···O2iii0.932.393.302 (2)167
C11—H11A···O2iv0.932.553.063 (2)115
C12—H12C···O2i0.962.393.334 (2)168
C17—H17A···O2iv0.932.413.318 (2)166
C18—H18A···O30.932.512.892 (2)105
C12—H12B···Cg1i0.962.693.515 (2)144

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x−1, y, z.

Footnotes

1This paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2086).

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