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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 5| May 2009| Page o1179

2,2′-Bis(all­yl­oxy)-1,1′-binaphth­yl

aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: seuwangwei@gmail.com

(Received 21 April 2009; accepted 28 April 2009; online 30 April 2009)

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 ππ stacking inter­actions are observed.

Related literature

For related structures, see: Fu & Zhao (2007[Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.]); Zhang et al. (2008[Zhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22O2

  • Mr = 366.46

  • Tetragonal, I 41

  • 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.892, Tmax = 0.990

  • 5346 measured reflections

  • 1024 independent reflections

  • 806 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] 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).
2,2'-Bis(allyloxy)-1,1'-binaphthyl top
Crystal data top
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 top
Rigaku SCXmini
diffractometer
1024 independent reflections
Radiation source: fine-focus sealed tube806 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 2.2°
ω scansh = 614
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1414
Tmin = 0.892, Tmax = 0.990l = 1717
5346 measured reflections
Refinement top
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 = 1.02 w = 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
Crystal data top
C26H22O2Z = 4
Mr = 366.46Mo Kα radiation
Tetragonal, I41µ = 0.08 mm1
a = 11.7167 (9) ÅT = 298 K
c = 14.583 (2) Å0.20 × 0.18 × 0.14 mm
V = 2001.9 (4) Å3
Data collection top
Rigaku SCXmini
diffractometer
1024 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
806 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.990Rint = 0.045
5346 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.095H-atom parameters constrained
S = 1.02Δρmax = 0.14 e Å3
1024 reflectionsΔρmin = 0.12 e Å3
127 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*/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)
H4A0.15370.16240.72930.059*
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)
H3A0.28730.20490.83770.060*
C50.1674 (2)0.0254 (3)0.5868 (2)0.0540 (7)
H5A0.09610.06020.58880.065*
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)
H11A0.44330.25780.92240.082*
H11B0.39790.14080.96070.082*
C120.5612 (4)0.1738 (3)0.9988 (3)0.0834 (11)
H12A0.55190.21021.05500.100*
C130.6573 (4)0.1243 (4)0.9849 (3)0.0976 (13)
H13C0.67090.08680.92980.117*
H13A0.71350.12591.03000.117*
Atomic displacement parameters (Å2) top
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, º) top
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—C20.9 (3)C9—C10—C4—C30.2 (4)
C8—C9—C1—C1i0.2 (4)C6—C7—C8—C90.0 (4)
C10—C9—C1—C1i179.1 (2)C10—C9—C8—C71.3 (4)
C8—C9—C10—C4178.5 (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—C5179.4 (2)C1—C2—C3—C40.9 (4)
C11—O1—C2—C1165.4 (2)C4—C10—C5—C6179.3 (3)
C11—O1—C2—C315.3 (4)C9—C10—C5—C60.8 (4)
C9—C1—C2—O1179.6 (2)C10—C5—C6—C70.5 (4)
C1i—C1—C2—O11.4 (4)C8—C7—C6—C50.9 (4)
C9—C1—C2—C31.1 (3)C2—O1—C11—C12169.1 (2)
C1i—C1—C2—C3179.3 (3)O1—C11—C12—C133.0 (5)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H22O2
Mr366.46
Crystal system, space groupTetragonal, I41
Temperature (K)298
a, c (Å)11.7167 (9), 14.583 (2)
V3)2001.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.18 × 0.14
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.892, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
5346, 1024, 806
Rint0.045
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.095, 1.02
No. of reflections1024
No. of parameters127
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.12

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationFu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317.  Web of Science CSD CrossRef 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 65| Part 5| May 2009| Page o1179
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds