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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1179.
Published online 2009 April 30. doi:  10.1107/S1600536809015815
PMCID: PMC2977843

2,2′-Bis(all­yloxy)-1,1′-binaphth­yl

Abstract

The complete mol­ecule of the title compound, C26H22O2, is generated by a crystallographic twofold rotation axis. The dihedral angle between the planes of the two symmetry-related naphthalene ring systems is 69.05 (4)°, while that between the naphthalene ring system and the allyl plane is 13.7 (2)°. No hydrogen bonds or aromatic π–π stacking inter­actions are observed.

Related literature

For related structures, see: Fu & Zhao (2007 [triangle]); Zhang et al. (2008 [triangle]).

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Object name is e-65-o1179-scheme1.jpg

Experimental

Crystal data

  • C26H22O2
  • M r = 366.46
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-o1179-efi1.jpg
  • a = 11.7167 (9) Å
  • c = 14.583 (2) Å
  • V = 2001.9 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.20 × 0.18 × 0.14 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.892, T max = 0.990
  • 5346 measured reflections
  • 1024 independent reflections
  • 806 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.095
  • S = 1.02
  • 1024 reflections
  • 127 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015815/ci2788sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015815/ci2788Isup2.hkl

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

Acknowledgments

The authors are grateful to the Starter Fund of Southeast University for financial support to buy the CCD X-ray diffractometer.

supplementary crystallographic information

Comment

The molecule is located on a twofold rotation axis. The dihedral angle between the two naphthalene ring systems is 69.05 (4)° while that between the naphthalene ring and allyl plane is 13.7 (2)°. The molecule is twisted around the central C1—C1A bond with a torsion angle C2—C1—C1A—C2A of -66.6 (3)°. There are no remarkable short intermolecular interactions observed in the structure.

Experimental

Racemic 1,1'-binaphthyl-2,2'-diol (2.86 g, 10 mmol) and allyl bromide (2.42 g, 20 mmol) were dissolved in acetone (50 ml) in the presence of K2CO3 (1.38 g, 10 mmol) and refluxed for 24 h. After the mixture was cooled to room temperature, the solution was filtered and rotated in vacuum. The title compound was purified by column chromatography with dichloromethane as eluent and was recrystallized from dichloromethane. Colorless single crystals of the title compound suitable for X-ray diffraction were obtained from an ethanol solution after a week.

Refinement

H atoms were positioned geometrically and were allowed to ride on the C atoms to which they are bonded, with C-H = 0.93-0.97 Å and Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs were merged prior to the final refinement.

Figures

Fig. 1.
The molecular structure of the compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Atoms labelled with the suffix A are generated by the symmetry operation (1-x, -y, z).

Crystal data

C26H22O2Dx = 1.216 Mg m3
Mr = 366.46Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41Cell parameters from 1024 reflections
Hall symbol: I 4bwθ = 2.0–27.5°
a = 11.7167 (9) ŵ = 0.08 mm1
c = 14.583 (2) ÅT = 298 K
V = 2001.9 (4) Å3Prism, colourless
Z = 40.20 × 0.18 × 0.14 mm
F(000) = 776

Data collection

Rigaku SCXmini diffractometer1024 independent reflections
Radiation source: fine-focus sealed tube806 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = −6→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −14→14
Tmin = 0.892, Tmax = 0.990l = −17→17
5346 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0479P)2 + 0.119P] where P = (Fo2 + 2Fc2)/3
1024 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = −0.12 e Å3

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
C90.3589 (2)0.0005 (2)0.65091 (16)0.0410 (6)
C10.4419 (2)−0.0269 (2)0.71920 (16)0.0406 (6)
C100.2494 (2)−0.0516 (2)0.65478 (17)0.0419 (6)
O10.49556 (16)−0.12473 (17)0.85183 (13)0.0557 (5)
C70.2987 (2)0.1036 (2)0.51508 (19)0.0571 (8)
H7A0.31470.15590.46880.068*
C20.4132 (2)−0.1021 (2)0.78793 (19)0.0451 (6)
C40.2253 (2)−0.1283 (2)0.72628 (18)0.0490 (6)
H4A0.1537−0.16240.72930.059*
C80.3794 (2)0.0793 (2)0.57953 (19)0.0486 (6)
H8A0.44990.11550.57640.058*
C30.3047 (2)−0.1536 (2)0.79115 (19)0.0499 (7)
H3A0.2873−0.20490.83770.060*
C50.1674 (2)−0.0254 (3)0.5868 (2)0.0540 (7)
H5A0.0961−0.06020.58880.065*
C60.1911 (2)0.0498 (3)0.5184 (2)0.0597 (8)
H6A0.13660.06580.47380.072*
C110.4636 (3)−0.1789 (3)0.9343 (2)0.0687 (9)
H11A0.4433−0.25780.92240.082*
H11B0.3979−0.14080.96070.082*
C120.5612 (4)−0.1738 (3)0.9988 (3)0.0834 (11)
H12A0.5519−0.21021.05500.100*
C130.6573 (4)−0.1243 (4)0.9849 (3)0.0976 (13)
H13C0.6709−0.08680.92980.117*
H13A0.7135−0.12591.03000.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C90.0387 (14)0.0427 (14)0.0415 (14)0.0017 (11)0.0029 (11)−0.0071 (12)
C10.0377 (13)0.0424 (14)0.0419 (13)−0.0010 (11)0.0017 (12)−0.0031 (12)
C100.0335 (14)0.0452 (14)0.0470 (14)0.0019 (12)0.0042 (12)−0.0120 (12)
O10.0517 (11)0.0685 (13)0.0468 (10)−0.0008 (10)−0.0022 (9)0.0134 (10)
C70.0595 (18)0.0593 (18)0.0524 (17)0.0089 (15)−0.0030 (14)0.0075 (14)
C20.0455 (14)0.0467 (14)0.0430 (13)0.0033 (12)0.0010 (13)−0.0022 (12)
C40.0389 (14)0.0541 (15)0.0539 (15)−0.0053 (13)0.0104 (13)−0.0073 (13)
C80.0422 (15)0.0506 (15)0.0529 (15)0.0006 (12)0.0003 (13)0.0025 (13)
C30.0504 (15)0.0525 (15)0.0468 (14)−0.0058 (13)0.0108 (14)0.0037 (13)
C50.0372 (15)0.0618 (17)0.0630 (18)0.0028 (13)−0.0016 (14)−0.0109 (16)
C60.0495 (17)0.074 (2)0.0556 (17)0.0094 (15)−0.0096 (15)−0.0009 (16)
C110.085 (2)0.073 (2)0.0484 (17)−0.0002 (18)0.0014 (17)0.0169 (16)
C120.106 (3)0.085 (3)0.0588 (19)0.004 (2)−0.020 (2)0.0141 (19)
C130.106 (3)0.089 (3)0.098 (3)0.001 (3)−0.044 (3)0.005 (3)

Geometric parameters (Å, °)

C9—C81.411 (4)C4—H4A0.93
C9—C101.422 (3)C8—H8A0.93
C9—C11.428 (3)C3—H3A0.93
C1—C21.376 (3)C5—C61.360 (4)
C1—C1i1.500 (5)C5—H5A0.93
C10—C41.405 (4)C6—H6A0.93
C10—C51.415 (4)C11—C121.482 (5)
O1—C21.368 (3)C11—H11A0.97
O1—C111.411 (4)C11—H11B0.97
C7—C81.363 (4)C12—C131.282 (5)
C7—C61.410 (4)C12—H12A0.93
C7—H7A0.93C13—H13C0.93
C2—C31.408 (4)C13—H13A0.93
C4—C31.359 (4)
C8—C9—C10117.6 (2)C4—C3—C2120.1 (3)
C8—C9—C1123.1 (2)C4—C3—H3A120.0
C10—C9—C1119.3 (2)C2—C3—H3A120.0
C2—C1—C9119.0 (2)C6—C5—C10121.0 (3)
C2—C1—C1i119.4 (2)C6—C5—H5A119.5
C9—C1—C1i121.6 (2)C10—C5—H5A119.5
C4—C10—C5121.5 (2)C5—C6—C7119.8 (3)
C4—C10—C9119.0 (2)C5—C6—H6A120.1
C5—C10—C9119.5 (2)C7—C6—H6A120.1
C2—O1—C11118.8 (2)O1—C11—C12108.6 (3)
C8—C7—C6120.2 (3)O1—C11—H11A110.0
C8—C7—H7A119.9C12—C11—H11A110.0
C6—C7—H7A119.9O1—C11—H11B110.0
O1—C2—C1116.6 (2)C12—C11—H11B110.0
O1—C2—C3122.1 (2)H11A—C11—H11B108.4
C1—C2—C3121.3 (2)C13—C12—C11126.6 (4)
C3—C4—C10121.2 (2)C13—C12—H12A116.7
C3—C4—H4A119.4C11—C12—H12A116.7
C10—C4—H4A119.4C12—C13—H13C120.0
C7—C8—C9121.8 (3)C12—C13—H13A120.0
C7—C8—H8A119.1H13C—C13—H13A120.0
C9—C8—H8A119.1
C8—C9—C1—C2178.0 (2)C5—C10—C4—C3179.6 (2)
C10—C9—C1—C2−0.9 (3)C9—C10—C4—C3−0.2 (4)
C8—C9—C1—C1i−0.2 (4)C6—C7—C8—C90.0 (4)
C10—C9—C1—C1i−179.1 (2)C10—C9—C8—C7−1.3 (4)
C8—C9—C10—C4−178.5 (2)C1—C9—C8—C7179.8 (2)
C1—C9—C10—C40.4 (3)C10—C4—C3—C20.4 (4)
C8—C9—C10—C51.7 (3)O1—C2—C3—C4179.8 (2)
C1—C9—C10—C5−179.4 (2)C1—C2—C3—C4−0.9 (4)
C11—O1—C2—C1165.4 (2)C4—C10—C5—C6179.3 (3)
C11—O1—C2—C3−15.3 (4)C9—C10—C5—C6−0.8 (4)
C9—C1—C2—O1−179.6 (2)C10—C5—C6—C7−0.5 (4)
C1i—C1—C2—O1−1.4 (4)C8—C7—C6—C50.9 (4)
C9—C1—C2—C31.1 (3)C2—O1—C11—C12−169.1 (2)
C1i—C1—C2—C3179.3 (3)O1—C11—C12—C133.0 (5)

Symmetry codes: (i) −x+1, −y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2788).

References

  • Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317. [PMC free article] [PubMed]

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