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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Dec 24;67(Pt 1):o220. doi: 10.1107/S1600536810052840

4,4′-Bis(2,2-diphenyl­vin­yl)-1,1′-biphen­yl

Hong-Ni Liu a,*, Gao Zhang a, Lan Hu a, Peng-Fei Su a, Yun-Feng Li b
PMCID: PMC3050360  PMID: 21522719

Abstract

The title mol­ecule, C40H30, lies on an inversion center. The two unique phenyl rings form dihedral angles of 51.98 (8) and 67.58 (8)° with the essentially planar biphenyl unit [maximum deviation = 0.0360 (14) Å].

Related literature

For applications of the title compound, see: Park et al. (2005 ▶); Kim et al. (2009 ▶). For the preparation of the title compound, see: Zheng et al. (2004 ▶).graphic file with name e-67-0o220-scheme1.jpg

Experimental

Crystal data

  • C40H30

  • M r = 510.7

  • Monoclinic, Inline graphic

  • a = 9.277 (2) Å

  • b = 14.625 (3) Å

  • c = 10.460 (2) Å

  • β = 92.669 (4)°

  • V = 1417.6 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 296 K

  • 0.39 × 0.25 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer

  • 6984 measured reflections

  • 2508 independent reflections

  • 1479 reflections with I > 2σ(I)

  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 0.110

  • S = 0.94

  • 2508 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.18 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052840/lh5185sup1.cif

e-67-0o220-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052840/lh5185Isup2.hkl

e-67-0o220-Isup2.hkl (123.2KB, hkl)

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

Acknowledgments

The authors are grateful for financial support from the Xi’an Modern Chemistry Institute (grant No. jcky28).

supplementary crystallographic information

Comment

Distyrylarylene (DSA) derivatives have been widely investigated because of there high thermal stability and good film forming ability. The title compound has been used to fabricate white organic light-emitting diodes (WOLEDs)(Kim et al., 2009; Park et al., 2005). The synthesis and luminescent properties of DPVBi have already been described (Zheng, et al. 2004). The molecular structure of the title compound is shown in Fig.1. The molecule lies on an inversion center. The two unique phenyl rings form dihedral angles of 51.98 (8) [for C9-C14] and 67.58 (8)° [for C15-C20] with the essentially planar biphenyl unit [maximum deviation = 0.0360 (14)Å]

Experimental

The synthesis of the crude product was carried out according to reported methods (Zheng, et al. 2004). Suitable crystals were obtained by evaporation of a tetrahydrofuran/methanol (1:9, v/v) solution of the title compound at room temperature. Spectroscopic analysis: IR(KBr, cm-1): 3020,1597,1494,1441,762,697,815; 1H NMR (CDCl3, δ, p.p.m.): 7.3 (s, 20H), 6.9—7.2 (m, 10 H).

Refinement

All H atoms were positioned geometrically and refined as riding [C—H = 0.93Å; Uiso(H) = 1.2Ueq(C)].

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms (symmetry code (A): 1-x, 2-y, -z).

Crystal data

C40H30 F(000) = 540
Mr = 510.7 Dx = 1.196 Mg m−3
Monoclinic, P21/c Melting point: 477 K
Hall symbol: -P 2ybc Mo Kα radiation, λ = 0.71073 Å
a = 9.277 (2) Å Cell parameters from 1536 reflections
b = 14.625 (3) Å θ = 2.4–25.1°
c = 10.460 (2) Å µ = 0.07 mm−1
β = 92.669 (4)° T = 296 K
V = 1417.6 (5) Å3 Block, yellow
Z = 2 0.39 × 0.25 × 0.18 mm
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Data collection

Bruker SMART CCD diffractometer 1479 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.030
graphite θmax = 25.1°, θmin = 2.4°
φ and ω scans h = −11→10
6984 measured reflections k = −17→17
2508 independent reflections l = −12→10
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Refinement

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)] = 0.043 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110 H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0637P)2] where P = (Fo2 + 2Fc2)/3
2508 reflections (Δ/σ)max < 0.001
181 parameters Δρmax = 0.12 e Å−3
0 restraints Δρmin = −0.18 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.69791 (18) 0.84611 (10) 0.10768 (16) 0.0652 (5)
H1 0.6951 0.7855 0.1343 0.078*
C2 0.57204 (17) 0.88788 (10) 0.06689 (14) 0.0625 (4)
H2 0.4864 0.8549 0.0677 0.075*
C3 0.56784 (15) 0.97810 (9) 0.02422 (13) 0.0488 (4)
C4 0.69840 (17) 1.02440 (10) 0.03150 (16) 0.0633 (5)
H4 0.7009 1.0854 0.0066 0.076*
C5 0.82414 (17) 0.98268 (10) 0.07443 (16) 0.0642 (5)
H5 0.9088 1.0168 0.0795 0.077*
C6 0.82915 (16) 0.89105 (10) 0.11058 (13) 0.0539 (4)
C7 0.96931 (16) 0.85159 (11) 0.15032 (14) 0.0609 (4)
H7 1.0411 0.8943 0.1703 0.073*
C8 1.01194 (17) 0.76349 (10) 0.16283 (14) 0.0570 (4)
C9 1.16235 (17) 0.74195 (11) 0.20673 (15) 0.0599 (4)
C10 1.2386 (2) 0.79640 (12) 0.29442 (18) 0.0746 (5)
H10 1.1933 0.8464 0.3300 0.090*
C11 1.3807 (2) 0.77781 (13) 0.33001 (19) 0.0849 (6)
H11 1.4301 0.8155 0.3887 0.102*
C12 1.4498 (2) 0.70404 (14) 0.27931 (19) 0.0835 (6)
H12 1.5463 0.6923 0.3014 0.100*
C13 1.3742 (2) 0.64829 (16) 0.19597 (19) 0.0928 (6)
H13 1.4194 0.5974 0.1625 0.111*
C14 1.2324 (2) 0.66610 (13) 0.16054 (17) 0.0809 (5)
H14 1.1828 0.6265 0.1046 0.097*
C15 0.91607 (18) 0.68499 (10) 0.12923 (15) 0.0588 (4)
C16 0.86251 (18) 0.62995 (10) 0.22408 (15) 0.0630 (4)
H16 0.8899 0.6411 0.3093 0.076*
C17 0.7692 (2) 0.55891 (11) 0.19388 (18) 0.0730 (5)
H17 0.7328 0.5235 0.2588 0.088*
C18 0.7301 (2) 0.54030 (12) 0.0686 (2) 0.0828 (6)
H18 0.6666 0.4927 0.0485 0.099*
C19 0.7846 (2) 0.59197 (14) −0.02639 (18) 0.0935 (6)
H19 0.7599 0.5786 −0.1115 0.112*
C20 0.8763 (2) 0.66401 (12) 0.00322 (17) 0.0815 (6)
H20 0.9120 0.6991 −0.0624 0.098*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0611 (11) 0.0537 (9) 0.0803 (12) 0.0013 (9) −0.0031 (9) 0.0190 (8)
C2 0.0585 (11) 0.0566 (10) 0.0719 (11) −0.0035 (8) −0.0022 (8) 0.0120 (8)
C3 0.0532 (9) 0.0464 (8) 0.0472 (8) 0.0022 (7) 0.0066 (7) −0.0038 (6)
C4 0.0540 (11) 0.0446 (8) 0.0918 (12) 0.0042 (8) 0.0095 (9) 0.0033 (8)
C5 0.0487 (10) 0.0507 (9) 0.0937 (12) 0.0002 (8) 0.0088 (9) −0.0001 (8)
C6 0.0510 (10) 0.0550 (9) 0.0558 (9) 0.0048 (8) 0.0044 (7) 0.0019 (7)
C7 0.0555 (11) 0.0601 (10) 0.0673 (10) 0.0027 (8) 0.0046 (8) 0.0031 (8)
C8 0.0604 (10) 0.0573 (10) 0.0536 (10) 0.0061 (8) 0.0068 (7) 0.0043 (7)
C9 0.0627 (11) 0.0613 (10) 0.0560 (9) 0.0105 (8) 0.0052 (8) 0.0096 (8)
C10 0.0694 (13) 0.0656 (11) 0.0882 (13) 0.0097 (9) −0.0017 (10) 0.0013 (9)
C11 0.0693 (13) 0.0806 (13) 0.1033 (15) 0.0018 (11) −0.0101 (11) 0.0094 (11)
C12 0.0641 (12) 0.1014 (15) 0.0855 (15) 0.0166 (12) 0.0084 (11) 0.0284 (12)
C13 0.0890 (16) 0.1085 (16) 0.0810 (14) 0.0430 (13) 0.0047 (12) 0.0004 (12)
C14 0.0833 (14) 0.0875 (13) 0.0713 (12) 0.0301 (11) −0.0033 (10) −0.0057 (10)
C15 0.0696 (11) 0.0540 (9) 0.0531 (10) 0.0130 (8) 0.0038 (8) 0.0019 (7)
C16 0.0745 (11) 0.0573 (9) 0.0572 (10) 0.0107 (9) 0.0035 (8) 0.0040 (8)
C17 0.0866 (13) 0.0547 (10) 0.0784 (13) 0.0044 (9) 0.0127 (10) 0.0072 (9)
C18 0.0938 (15) 0.0632 (11) 0.0905 (15) −0.0015 (10) −0.0057 (12) −0.0074 (11)
C19 0.1305 (18) 0.0808 (13) 0.0676 (12) −0.0064 (13) −0.0119 (12) −0.0094 (11)
C20 0.1173 (17) 0.0712 (12) 0.0558 (11) −0.0056 (11) 0.0041 (10) 0.0024 (9)
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Geometric parameters (Å, °)

C1—C2 1.368 (2) C10—H10 0.9300
C1—C6 1.383 (2) C11—C12 1.374 (2)
C1—H1 0.9300 C11—H11 0.9300
C2—C3 1.3929 (19) C12—C13 1.363 (3)
C2—H2 0.9300 C12—H12 0.9300
C3—C4 1.387 (2) C13—C14 1.375 (3)
C3—C3i 1.481 (3) C13—H13 0.9300
C4—C5 1.373 (2) C14—H14 0.9300
C4—H4 0.9300 C15—C20 1.386 (2)
C5—C6 1.393 (2) C15—C16 1.388 (2)
C5—H5 0.9300 C16—C17 1.379 (2)
C6—C7 1.465 (2) C16—H16 0.9300
C7—C8 1.352 (2) C17—C18 1.371 (2)
C7—H7 0.9300 C17—H17 0.9300
C8—C9 1.482 (2) C18—C19 1.364 (3)
C8—C15 1.484 (2) C18—H18 0.9300
C9—C10 1.384 (2) C19—C20 1.380 (3)
C9—C14 1.384 (2) C19—H19 0.9300
C10—C11 1.380 (3) C20—H20 0.9300
C2—C1—C6 122.16 (14) C12—C11—C10 120.49 (19)
C2—C1—H1 118.9 C12—C11—H11 119.8
C6—C1—H1 118.9 C10—C11—H11 119.8
C1—C2—C3 122.25 (15) C13—C12—C11 118.78 (18)
C1—C2—H2 118.9 C13—C12—H12 120.6
C3—C2—H2 118.9 C11—C12—H12 120.6
C4—C3—C2 115.70 (14) C12—C13—C14 121.05 (19)
C4—C3—C3i 122.27 (16) C12—C13—H13 119.5
C2—C3—C3i 122.02 (17) C14—C13—H13 119.5
C5—C4—C3 121.84 (14) C13—C14—C9 121.11 (19)
C5—C4—H4 119.1 C13—C14—H14 119.4
C3—C4—H4 119.1 C9—C14—H14 119.4
C4—C5—C6 122.23 (15) C20—C15—C16 117.58 (16)
C4—C5—H5 118.9 C20—C15—C8 121.76 (14)
C6—C5—H5 118.9 C16—C15—C8 120.66 (14)
C1—C6—C5 115.68 (14) C17—C16—C15 120.99 (16)
C1—C6—C7 126.01 (14) C17—C16—H16 119.5
C5—C6—C7 118.30 (14) C15—C16—H16 119.5
C8—C7—C6 130.88 (15) C18—C17—C16 120.27 (16)
C8—C7—H7 114.6 C18—C17—H17 119.9
C6—C7—H7 114.6 C16—C17—H17 119.9
C7—C8—C9 119.95 (15) C19—C18—C17 119.70 (18)
C7—C8—C15 123.00 (14) C19—C18—H18 120.1
C9—C8—C15 117.00 (13) C17—C18—H18 120.1
C10—C9—C14 117.29 (16) C18—C19—C20 120.32 (18)
C10—C9—C8 121.86 (14) C18—C19—H19 119.8
C14—C9—C8 120.85 (16) C20—C19—H19 119.8
C11—C10—C9 121.19 (17) C19—C20—C15 121.09 (17)
C11—C10—H10 119.4 C19—C20—H20 119.5
C9—C10—H10 119.4 C15—C20—H20 119.5
C6—C1—C2—C3 0.7 (2) C8—C9—C10—C11 −177.03 (15)
C1—C2—C3—C4 −3.0 (2) C9—C10—C11—C12 −0.4 (3)
C1—C2—C3—C3i 177.73 (16) C10—C11—C12—C13 −1.7 (3)
C2—C3—C4—C5 1.9 (2) C11—C12—C13—C14 1.4 (3)
C3i—C3—C4—C5 −178.81 (15) C12—C13—C14—C9 1.0 (3)
C3—C4—C5—C6 1.4 (2) C10—C9—C14—C13 −3.0 (3)
C2—C1—C6—C5 2.6 (2) C8—C9—C14—C13 176.71 (15)
C2—C1—C6—C7 −178.80 (14) C7—C8—C15—C20 71.1 (2)
C4—C5—C6—C1 −3.7 (2) C9—C8—C15—C20 −106.38 (18)
C4—C5—C6—C7 177.62 (14) C7—C8—C15—C16 −108.71 (17)
C1—C6—C7—C8 17.8 (2) C9—C8—C15—C16 73.86 (18)
C5—C6—C7—C8 −163.63 (15) C20—C15—C16—C17 −2.1 (2)
C6—C7—C8—C9 −179.39 (14) C8—C15—C16—C17 177.65 (14)
C6—C7—C8—C15 3.3 (2) C15—C16—C17—C18 1.3 (2)
C7—C8—C9—C10 34.1 (2) C16—C17—C18—C19 0.5 (3)
C15—C8—C9—C10 −148.38 (15) C17—C18—C19—C20 −1.5 (3)
C7—C8—C9—C14 −145.60 (15) C18—C19—C20—C15 0.6 (3)
C15—C8—C9—C14 31.9 (2) C16—C15—C20—C19 1.2 (3)
C14—C9—C10—C11 2.7 (2) C8—C15—C20—C19 −178.61 (16)
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Symmetry codes: (i) −x+1, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5185).

References

  1. Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Kim, Y.-H., Seo, J. H., Hyung, G. W., Lee, S. Y., Ryu, D. H., Chae, S. J., Shin, S. S., Kim, Y. K. & Kim, W. Y. (2009). Mol. Cryst. Liq. Cryst. 510, 282–292.
  3. Park, J. S., Lee, J. W., Kim, Y. M., Bae, S. J., Jang, J., Kim, J. K. & Ju, B. K. (2005). J. Electrochem. Soc. 152, H196–H199.
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  5. Zheng, X.-Y., Zhu, W.-Q., Wu, Y.-Z., Ding, B.-D., Jiang, X.-Y., Zhang, Z.-L., Sun, R.-G. & Xu, S.-H. (2004). Guangxue Xuebao, 24, 70–74.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052840/lh5185sup1.cif

e-67-0o220-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052840/lh5185Isup2.hkl

e-67-0o220-Isup2.hkl (123.2KB, hkl)

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

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

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