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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Page o1601
doi:10.1107/S160053681102099X

1,4-Dimeth­­oxy-2,5-bis­­{2-[4-(tri­fluoro­meth­yl)phen­yl]ethyn­yl}benzene

Baohai Zhao,a Jimao Lin,a Cuihua Zhaoa* and Ziying Wangb

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and bDepartment of Chemistry and Environmental Science, Taishan University, Taian 271021, Shandong, People's Republic of China
*Correspondence e-mail: zhaobaohai0136@163.com

(Received 9 May 2011; accepted 31 May 2011; online 11 June 2011)

The asymmetric unit of the title compound, C26H16F6O2, contains one half of the mol­ecule situated on an inversion centre. In the rod-like mol­ecule, the two terminal benzene rings form a dihedral angle of 71.9 (1)° with the central benzene ring. The trifluoro­methyl group is rotationally disordered over two orientations in a 0.53 (1):0.47 (1) ratio. The crystal packing exhibits no classical inter­molecular inter­actions.

Related literature

For applications and details of the synthesis of (aryl­ene)­ethynylene derivatives, see: Dirk et al. (2001[Dirk, S. M., Price, D. W., Chanteau, S., Kosynkin, D. V. & Tour, J. M. (2001). Tetrahedron, 57, 5109-5121.]); Miljanić et al. (2005[Miljanić, O. Š., Holmes, D. & Vollhardt, K. P. C. (2005). Org. Lett. 7, 4001-4004.]); Morin et al. (2007[Morin, J. F., Sasaki, T., Shirai, Y., Guerrero, J. M. & Tour, J. M. (2007). J. Org. Chem. 72, 9481-9490.]). For the crystal structure of a related 1,4-bis­(p-tolyl­ethyn­yl)benzene, see: Filatov & Petrukhina (2005[Filatov, A. S. & Petrukhina, M. A. (2005). Acta Cryst. C61, o193-o194.]).

[Scheme 1]

Experimental

Crystal data

  • C26H16F6O2

  • Mr = 474.39

  • Monoclinic, P 21 /c

  • a = 11.1473 (4) Å

  • b = 13.0795 (6) Å

  • c = 7.5875 (4) Å

  • β = 97.467 (3)°

  • V = 1096.88 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 293 K

  • 0.22 × 0.20 × 0.19 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.977

  • 9899 measured reflections

  • 2484 independent reflections

  • 1753 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.04

  • 2484 reflections

  • 184 parameters

  • 30 restraints

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102099X/cv5093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102099X/cv5093Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681102099X/cv5093Isup3.cml

checkCIF report


Comment top

Recently, the synthesis and applications of new aryleneethynylene derivatives were reported (Dirk et al., 2001; Miljanić et al., 2005; Morin et al., 2007). To make our own contribution in this field of material science, herewith we report the synthesis and crystal structure of the title compound, (I), which can be used as luminescent material.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those reported for 1,4-bis(p-tolylethynyl)benzene (Filatov & Petrukhina, 2005). The asymmetric unit of (I) contains a half of the rod-like molecule. The centroid of the central benzene ring is situated on an inversion centre. The central benzene ring and C2–C7 ring form a dihedral angle of 71.9 (1)°. The crystal packing exhibits no classical intermolecular interactions.

Related literature top

For applications and details of the synthesis of aryleneethynylene derivatives, see: Dirk et al. (2001); Miljanić et al. (2005); Morin et al. (2007). For the crystal structure of a related 1,4-bis(p-tolylethynyl)benzene, see: Filatov & Petrukhina (2005).

Experimental top

1,4-Dimethoxy-2,5-diethynylbenzene (93 mg, 0.5 mmol), Pd(PPh3)2Cl2 (17.5 mg)and CuI (9.5 mg) were added to triethylamine (3 ml) and tetrahydrofuran (9 ml)in a Schlenk flask under N2 atmosphere. The mixture was stirred at room temperature overnight. Then the solution was cooled to room temperature and the solvent was removed in vacuum. CH2Cl2 (15 ml) was added and the suspension was filtered. The filtrate was washed with HCl (1 mol l-1), ammonium chloride solution and water. Then organic phase was dried with MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel to afford the title compound (185.3 mg, 78%). Crystals suitable for X-ray structure analysis were obtained by slowly evaporating dichloromethane solution of the title compound at room temperature.

Refinement top

All the H atoms were treated as riding atoms in geometrically idealized positions (C—H 0.93–0.96 Å), with Uiso(H) = 1.2–1.5Ueq(C). Trifluoromethyl fragment was treated as rotationally disordered over two orientations with the refined occupancies of 0.53 (1):0.47 (1), respectively.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-numbering scheme and 50% probabilty displacement ellipsoids. Unlabelled atoms are related with the labelled ones by symmetry operation (-x, 2 - y, 2 - z). For the disordered F atoms, only major parts are shown.
1,4-Dimethoxy-2,5-bis{2-[4-(trifluoromethyl)phenyl]ethynyl}benzene top
Crystal data top
C26H16F6O2F(000) = 484
Mr = 474.39Dx = 1.436 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.1473 (4) Åθ = 2.4–27.4°
b = 13.0795 (6) ŵ = 0.13 mm−1
c = 7.5875 (4) ÅT = 293 K
β = 97.467 (3)°Block, colourless
V = 1096.88 (9) Å30.22 × 0.20 × 0.19 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer		2484 independent reflections
Radiation source: fine-focus sealed tube1753 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −14→14
Tmin = 0.973, Tmax = 0.977k = −15→16
9899 measured reflectionsl = −9→9
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.235P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2484 reflectionsΔρmax = 0.16 e Å−3
184 parametersΔρmin = −0.21 e Å−3
30 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)
Crystal data top
C26H16F6O2V = 1096.88 (9) Å3
Mr = 474.39Z = 2
Monoclinic, P21/cMo Kα radiation
a = 11.1473 (4) ŵ = 0.13 mm−1
b = 13.0795 (6) ÅT = 293 K
c = 7.5875 (4) Å0.22 × 0.20 × 0.19 mm
β = 97.467 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		2484 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		1753 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.977Rint = 0.022
9899 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04230 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.04Δρmax = 0.16 e Å−3
2484 reflectionsΔρmin = −0.21 e Å−3
184 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
C10.75647 (18)0.83209 (17)0.5592 (3)0.0718 (6)
C20.63855 (14)0.85402 (14)0.6275 (2)0.0527 (4)
C30.54917 (16)0.78099 (15)0.6153 (3)0.0588 (5)
H30.56170.71780.56470.071*
C40.44076 (15)0.80134 (14)0.6781 (2)0.0562 (5)
H40.38050.75180.66970.067*
C50.42165 (13)0.89548 (14)0.7537 (2)0.0473 (4)
C60.51220 (16)0.96868 (14)0.7635 (3)0.0589 (5)
H60.49991.03220.81310.071*
C70.62038 (16)0.94824 (15)0.7003 (3)0.0608 (5)
H70.68060.99780.70690.073*
C80.31058 (14)0.91755 (14)0.8243 (2)0.0525 (4)
C90.22045 (14)0.93931 (13)0.8846 (2)0.0497 (4)
C100.10877 (13)0.96910 (12)0.9454 (2)0.0452 (4)
C110.03456 (14)1.03921 (12)0.8455 (2)0.0477 (4)
H110.05841.06560.74170.057*
C120.07381 (13)0.92971 (12)1.1021 (2)0.0455 (4)
C130.1199 (2)0.82346 (18)1.3576 (3)0.0769 (6)
H13A0.11090.87911.43720.115*
H13B0.18230.77821.41050.115*
H13C0.04490.78671.33480.115*
O10.15207 (10)0.86246 (10)1.19450 (17)0.0605 (4)
F10.7461 (6)0.8553 (4)0.3877 (5)0.0928 (16)0.530 (10)
F20.8484 (5)0.8832 (9)0.6296 (14)0.183 (5)0.530 (10)
F30.7807 (6)0.7351 (3)0.5523 (9)0.125 (3)0.530 (10)
F1'0.7695 (6)0.7396 (4)0.5079 (11)0.136 (4)0.470 (10)
F2'0.8458 (4)0.8398 (6)0.6905 (7)0.0953 (18)0.470 (10)
F3'0.7830 (9)0.8979 (10)0.4453 (17)0.205 (6)0.470 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0550 (12)0.0973 (17)0.0678 (14)0.0107 (11)0.0252 (10)−0.0029 (13)
C20.0413 (8)0.0727 (12)0.0462 (9)0.0070 (8)0.0135 (7)−0.0022 (8)
C30.0545 (10)0.0638 (12)0.0603 (11)0.0052 (8)0.0152 (8)−0.0127 (9)
C40.0465 (9)0.0623 (11)0.0613 (11)−0.0033 (8)0.0128 (8)−0.0070 (9)
C50.0374 (8)0.0606 (10)0.0454 (9)0.0062 (7)0.0118 (7)0.0025 (8)
C60.0543 (10)0.0562 (11)0.0703 (12)0.0008 (8)0.0239 (9)−0.0095 (9)
C70.0468 (9)0.0697 (12)0.0696 (12)−0.0083 (8)0.0213 (9)−0.0073 (10)
C80.0438 (9)0.0616 (11)0.0542 (10)0.0045 (8)0.0146 (7)0.0039 (8)
C90.0409 (8)0.0552 (10)0.0552 (10)0.0014 (7)0.0142 (7)0.0028 (8)
C100.0354 (7)0.0494 (9)0.0531 (9)−0.0011 (7)0.0144 (7)−0.0027 (7)
C110.0422 (8)0.0532 (10)0.0503 (9)−0.0016 (7)0.0162 (7)0.0039 (8)
C120.0379 (8)0.0464 (9)0.0532 (10)0.0014 (6)0.0099 (7)0.0029 (7)
C130.0759 (13)0.0846 (15)0.0732 (14)0.0208 (11)0.0207 (11)0.0317 (12)
O10.0510 (7)0.0679 (8)0.0653 (8)0.0144 (6)0.0170 (6)0.0167 (6)
F10.089 (3)0.120 (3)0.081 (2)0.005 (2)0.0551 (18)0.006 (2)
F20.056 (3)0.278 (10)0.228 (8)−0.065 (5)0.068 (4)−0.175 (8)
F30.119 (4)0.109 (4)0.168 (5)0.074 (3)0.095 (4)0.067 (4)
F1'0.071 (3)0.180 (8)0.163 (5)0.005 (3)0.031 (3)−0.118 (6)
F2'0.0321 (19)0.142 (4)0.115 (3)0.0013 (19)0.0200 (17)0.000 (3)
F3'0.142 (8)0.247 (10)0.260 (10)0.105 (7)0.157 (8)0.190 (9)
Geometric parameters (Å, º) top
C1—F21.281 (4)C6—C71.380 (2)
C1—F3'1.281 (4)C6—H60.9300
C1—F1'1.285 (4)C7—H70.9300
C1—F31.300 (4)C8—C91.191 (2)
C1—F2'1.318 (4)C9—C101.437 (2)
C1—F11.327 (4)C10—C111.391 (2)
C1—C21.502 (2)C10—C121.397 (2)
C2—C31.375 (3)C11—C12i1.381 (2)
C2—C71.376 (3)C11—H110.9300
C3—C41.381 (2)C12—O11.3664 (19)
C3—H30.9300C12—C11i1.381 (2)
C4—C51.386 (2)C13—O11.427 (2)
C4—H40.9300C13—H13A0.9600
C5—C61.386 (2)C13—H13B0.9600
C5—C81.441 (2)C13—H13C0.9600
F2—C1—F3'71.9 (5)C5—C4—H4119.9
F2—C1—F1'120.1 (5)C6—C5—C4119.06 (14)
F3'—C1—F1'112.5 (6)C6—C5—C8119.78 (16)
F2—C1—F3111.5 (5)C4—C5—C8121.15 (16)
F3'—C1—F3124.1 (6)C7—C6—C5120.70 (17)
F1'—C1—F315.5 (5)C7—C6—H6119.6
F2—C1—F2'32.8 (6)C5—C6—H6119.6
F3'—C1—F2'103.9 (7)C2—C7—C6119.57 (17)
F1'—C1—F2'101.3 (4)C2—C7—H7120.2
F3—C1—F2'87.9 (5)C6—C7—H7120.2
F2—C1—F1104.7 (6)C9—C8—C5177.5 (2)
F3'—C1—F135.2 (8)C8—C9—C10175.89 (19)
F1'—C1—F185.2 (4)C11—C10—C12119.64 (13)
F3—C1—F1100.1 (4)C11—C10—C9118.86 (14)
F2'—C1—F1133.2 (3)C12—C10—C9121.50 (15)
F2—C1—C2116.4 (3)C12i—C11—C10121.18 (15)
F3'—C1—C2113.2 (3)C12i—C11—H11119.4
F1'—C1—C2115.0 (4)C10—C11—H11119.4
F3—C1—C2113.4 (3)O1—C12—C11i124.45 (15)
F2'—C1—C2109.5 (3)O1—C12—C10116.37 (13)
F1—C1—C2109.1 (3)C11i—C12—C10119.18 (15)
C3—C2—C7120.41 (15)O1—C13—H13A109.5
C3—C2—C1120.20 (17)O1—C13—H13B109.5
C7—C2—C1119.38 (17)H13A—C13—H13B109.5
C2—C3—C4120.11 (17)O1—C13—H13C109.5
C2—C3—H3119.9H13A—C13—H13C109.5
C4—C3—H3119.9H13B—C13—H13C109.5
C3—C4—C5120.14 (17)C12—O1—C13117.37 (13)
C3—C4—H4119.9
F2—C1—C2—C3−154.8 (8)C8—C5—C6—C7178.50 (18)
F3'—C1—C2—C3124.7 (9)C3—C2—C7—C60.9 (3)
F1'—C1—C2—C3−6.6 (5)C1—C2—C7—C6−179.94 (18)
F3—C1—C2—C3−23.5 (4)C5—C6—C7—C2−0.3 (3)
F2'—C1—C2—C3−119.9 (4)C6—C5—C8—C9−1 (5)
F1—C1—C2—C387.1 (3)C4—C5—C8—C9178 (100)
F2—C1—C2—C726.0 (8)C5—C8—C9—C1085 (5)
F3'—C1—C2—C7−54.5 (10)C8—C9—C10—C11−11 (3)
F1'—C1—C2—C7174.2 (5)C8—C9—C10—C12169 (3)
F3—C1—C2—C7157.3 (4)C12—C10—C11—C12i−0.4 (3)
F2'—C1—C2—C760.9 (4)C9—C10—C11—C12i179.90 (16)
F1—C1—C2—C7−92.1 (3)C11—C10—C12—O1−179.04 (15)
C7—C2—C3—C4−0.8 (3)C9—C10—C12—O10.6 (2)
C1—C2—C3—C4−179.95 (18)C11—C10—C12—C11i0.4 (3)
C2—C3—C4—C50.0 (3)C9—C10—C12—C11i−179.92 (16)
C3—C4—C5—C60.6 (3)C11i—C12—O1—C13−1.1 (3)
C3—C4—C5—C8−178.37 (17)C10—C12—O1—C13178.26 (17)
C4—C5—C6—C7−0.5 (3)
Symmetry code: (i) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formulaC26H16F6O2
Mr474.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.1473 (4), 13.0795 (6), 7.5875 (4)
β (°) 97.467 (3)
V (Å3)1096.88 (9)
Z2
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.22 × 0.20 × 0.19
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.973, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections		9899, 2484, 1753
Rint0.022
(sin θ/λ)max (Å−1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.04
No. of reflections2484
No. of parameters184
No. of restraints30
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Shandong Province (grant No. Q2008B02) and the Science Foundation of the Ministry of Education of China (grant No. 200804221009).

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDirk, S. M., Price, D. W., Chanteau, S., Kosynkin, D. V. & Tour, J. M. (2001). Tetrahedron, 57, 5109–5121.  CrossRef CAS Google Scholar
 First citationFilatov, A. S. & Petrukhina, M. A. (2005). Acta Cryst. C61, o193–o194.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMiljanić, O. Š., Holmes, D. & Vollhardt, K. P. C. (2005). Org. Lett. 7, 4001–4004.  Web of Science PubMed Google Scholar
 First citationMorin, J. F., Sasaki, T., Shirai, Y., Guerrero, J. M. & Tour, J. M. (2007). J. Org. Chem. 72, 9481–9490.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 7| July 2011| Page o1601
doi:10.1107/S160053681102099X
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