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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1930.
Published online 2009 July 18. doi:  10.1107/S1600536809026920
PMCID: PMC2977130

4,4′-Bis(2-methoxy­lstyr­yl)biphen­yl

Abstract

The title compound, C30H26O2, was prepared by the reaction of a Wittig reagent and 2-methoxy­benzaldehyde. The mol­ecule lies about an inversion centre located at the midpoint of the C—C bond between the inner benzene rings. The crystal structure is stabilized by C—H(...)π inter­actions.

Related literature

For the optical properties of ethyl­ene biphenyls, see: Song et al. (2003 [triangle]). For comparative bond lengths, see: Trueblood et al. (1982 [triangle]).

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Object name is e-65-o1930-scheme1.jpg

Experimental

Crystal data

  • C30H26O2
  • M r = 418.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1930-efi1.jpg
  • a = 15.499 (3) Å
  • b = 5.5050 (11) Å
  • c = 13.445 (3) Å
  • β = 98.61 (3)°
  • V = 1134.2 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 2541 measured reflections
  • 2431 independent reflections
  • 1144 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.218
  • S = 1.01
  • 2431 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026920/at2831sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026920/at2831Isup2.hkl

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

supplementary crystallographic information

Comment

Ethylene biphenyl have received considerable attention in the literature. They are attractive from several points of view, such as the optics characteristic. (Song et al., 2003). As part of our search for new ethylene biphenyl compounds we synthesized the title compound (I), and describe its structure here.

As shown in Fig. 1, the molecule has an inversion centre lied on the midpoint of the C—C bond between the inner benzene rings. The C8—C9 bond length of 1.314 (4)Å is comparable with C—C double bond [1.336 (2) Å] reported (Trueblood et al., 1982).

In the structure, there is no classcial hydrogen bonds. The crystal structure is stabilized by C—H···π interactions (Table 1).

Experimental

A mixture of the Wittig-reagent (0.1 mol), and 2-methoxybenzaldehyde (0.2 mol) was stirred in refluxing N,N-dimethylformamide (20 mL) for 4 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 - 0.96 Å, and with Uiso(H) =1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C30H26O2F(000) = 444
Mr = 418.51Dx = 1.225 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 987 reflections
a = 15.499 (3) Åθ = 2.2–27.5°
b = 5.5050 (11) ŵ = 0.08 mm1
c = 13.445 (3) ÅT = 293 K
β = 98.61 (3)°Block, yellow
V = 1134.2 (4) Å30.25 × 0.20 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer1144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 27.0°, θmin = 1.3°
[var phi] and ω scansh = −18→18
2541 measured reflectionsk = −6→0
2431 independent reflectionsl = −16→0

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.218w = 1/[σ2(Fo2) + (0.1165P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2431 reflectionsΔρmax = 0.22 e Å3
146 parametersΔρmin = −0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (8)

Special details

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
O10.37628 (14)0.1134 (4)0.17470 (14)0.0684 (7)
C10.4420 (2)−0.0626 (6)0.1680 (2)0.0738 (11)
H1A0.4491−0.16270.22710.111*
H1B0.49610.01780.16270.111*
H1C0.4254−0.16190.10960.111*
C20.35652 (18)0.2759 (5)0.09673 (19)0.0493 (7)
C30.3997 (2)0.2830 (6)0.0136 (2)0.0602 (9)
H3A0.44420.17270.00820.072*
C40.3770 (2)0.4529 (7)−0.0611 (2)0.0665 (10)
H4A0.40660.4568−0.11640.080*
C50.3114 (2)0.6160 (6)−0.0545 (2)0.0625 (9)
H5A0.29630.7302−0.10510.075*
C60.26746 (19)0.6097 (6)0.0283 (2)0.0565 (8)
H6A0.22330.72160.03270.068*
C70.28816 (16)0.4391 (5)0.10519 (19)0.0456 (7)
C80.24047 (17)0.4232 (5)0.19277 (19)0.0497 (8)
H8A0.25370.29110.23540.060*
C90.18161 (18)0.5755 (5)0.2166 (2)0.0493 (8)
H9A0.17050.71200.17590.059*
C100.13109 (17)0.5531 (5)0.30137 (19)0.0434 (7)
C110.1426 (2)0.3639 (6)0.3705 (2)0.0616 (9)
H11A0.18510.24720.36540.074*
C120.0920 (2)0.3457 (5)0.4468 (2)0.0615 (9)
H12A0.10160.21590.49140.074*
C130.02809 (16)0.5122 (5)0.45942 (19)0.0406 (6)
C140.0180 (2)0.7035 (5)0.3911 (2)0.0556 (8)
H14A−0.02390.82160.39700.067*
C150.0683 (2)0.7237 (6)0.3145 (2)0.0576 (9)
H15A0.05960.85530.27070.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0824 (16)0.0795 (15)0.0477 (12)0.0305 (13)0.0238 (11)0.0099 (12)
C10.083 (2)0.081 (3)0.057 (2)0.027 (2)0.0114 (17)−0.0030 (18)
C20.0517 (16)0.0613 (18)0.0365 (15)−0.0004 (15)0.0114 (12)−0.0031 (14)
C30.0571 (18)0.082 (2)0.0457 (17)0.0071 (17)0.0228 (15)−0.0038 (17)
C40.0594 (19)0.104 (3)0.0409 (17)−0.0055 (19)0.0235 (14)0.0008 (18)
C50.0603 (19)0.089 (2)0.0393 (16)−0.0015 (19)0.0110 (14)0.0128 (17)
C60.0491 (16)0.075 (2)0.0465 (16)0.0034 (16)0.0091 (13)0.0075 (16)
C70.0404 (15)0.063 (2)0.0350 (14)−0.0034 (13)0.0107 (11)−0.0011 (13)
C80.0475 (16)0.065 (2)0.0393 (15)0.0066 (15)0.0136 (12)0.0041 (14)
C90.0523 (17)0.0556 (19)0.0423 (15)−0.0007 (15)0.0142 (12)0.0004 (13)
C100.0411 (15)0.0501 (17)0.0397 (15)−0.0015 (13)0.0081 (12)−0.0064 (13)
C110.0591 (18)0.065 (2)0.067 (2)0.0249 (16)0.0306 (16)0.0138 (17)
C120.067 (2)0.063 (2)0.0608 (19)0.0243 (17)0.0318 (16)0.0209 (16)
C130.0403 (14)0.0462 (15)0.0357 (13)−0.0002 (12)0.0078 (10)−0.0044 (12)
C140.0585 (18)0.0579 (19)0.0554 (17)0.0198 (15)0.0248 (14)0.0066 (15)
C150.0662 (19)0.062 (2)0.0490 (16)0.0172 (16)0.0235 (15)0.0154 (15)

Geometric parameters (Å, °)

O1—C21.377 (3)C8—C91.314 (4)
O1—C11.419 (4)C8—H8A0.9300
C1—H1A0.9600C9—C101.482 (4)
C1—H1B0.9600C9—H9A0.9300
C1—H1C0.9600C10—C151.383 (4)
C2—C31.386 (4)C10—C111.389 (4)
C2—C71.407 (4)C11—C121.386 (4)
C3—C41.379 (4)C11—H11A0.9300
C3—H3A0.9300C12—C131.379 (4)
C4—C51.370 (4)C12—H12A0.9300
C4—H4A0.9300C13—C141.391 (4)
C5—C61.390 (4)C13—C13i1.500 (5)
C5—H5A0.9300C14—C151.387 (4)
C6—C71.398 (4)C14—H14A0.9300
C6—H6A0.9300C15—H15A0.9300
C7—C81.484 (3)
C2—O1—C1118.4 (2)C9—C8—C7127.1 (3)
O1—C1—H1A109.5C9—C8—H8A116.5
O1—C1—H1B109.5C7—C8—H8A116.5
H1A—C1—H1B109.5C8—C9—C10126.9 (3)
O1—C1—H1C109.5C8—C9—H9A116.5
H1A—C1—H1C109.5C10—C9—H9A116.5
H1B—C1—H1C109.5C15—C10—C11116.5 (2)
O1—C2—C3123.6 (3)C15—C10—C9120.3 (3)
O1—C2—C7116.0 (2)C11—C10—C9123.2 (2)
C3—C2—C7120.5 (3)C12—C11—C10121.3 (3)
C4—C3—C2120.4 (3)C12—C11—H11A119.4
C4—C3—H3A119.8C10—C11—H11A119.4
C2—C3—H3A119.8C13—C12—C11122.7 (3)
C5—C4—C3120.5 (3)C13—C12—H12A118.7
C5—C4—H4A119.7C11—C12—H12A118.7
C3—C4—H4A119.7C12—C13—C14115.7 (2)
C4—C5—C6119.5 (3)C12—C13—C13i122.4 (3)
C4—C5—H5A120.2C14—C13—C13i121.8 (3)
C6—C5—H5A120.2C15—C14—C13122.1 (3)
C5—C6—C7121.6 (3)C15—C14—H14A119.0
C5—C6—H6A119.2C13—C14—H14A119.0
C7—C6—H6A119.2C10—C15—C14121.7 (3)
C6—C7—C2117.5 (2)C10—C15—H15A119.2
C6—C7—C8122.7 (3)C14—C15—H15A119.2
C2—C7—C8119.8 (3)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1C···Cg1ii0.962.763.611 (3)149
C15—H15A···Cg2iii0.932.913.643 (3)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2831).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, H. C., Xu, X. H. & Liu, G. R. (2003). Chin. Chem. Res.14, 1–5.
  • Trueblood, K., Mirsky, K., Maverick, E., Knobler, C. & Grossenbacher, L. (1982). Acta Cryst. B38, 2428–2435.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography