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access2,2′-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
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.
![[Scheme 1]](ci2788scheme1.gif)
Experimental
Crystal data
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Data collection: CrystalClear (Rigaku, 2005![[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]](../../../../../../logos/arrows/e_arr.gif "Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.")
); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536809015815/ci2788sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536809015815/ci2788Isup2.hkl
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 with dichloromethane as 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.
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 Friedel pairs were merged prior to the final refinement.
Data collection: CrystalClear (Rigaku, 2005); cell 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).
![[Figure 1]](./ci2788fig1thm.gif) | 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). |
| C26H22O2 | Dx = 1.216 Mg m−3 |
| Mr = 366.46 | Mo Kα radiation, λ = 0.71073 Å |
| Tetragonal, I41 | Cell parameters from 1024 reflections |
| Hall symbol: I 4bw | θ = 2.0–27.5° |
| a = 11.7167 (9) Å | µ = 0.08 mm−1 |
| c = 14.583 (2) Å | T = 298 K |
| V = 2001.9 (4) Å3 | Prism, colourless |
| Z = 4 | 0.20 × 0.18 × 0.14 mm |
| F(000) = 776 |
| Rigaku SCXmini diffractometer | 1024 independent reflections |
| Radiation source: fine-focus sealed tube | 806 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.045 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 2.2° |
| ω scans | h = −6→14 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −14→14 |
| Tmin = 0.892, Tmax = 0.990 | l = −17→17 |
| 5346 measured reflections |
| 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.095 | H-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 parameters | Δρmax = 0.14 e Å−3 |
| 1 restraint | Δρmin = −0.12 e Å−3 |
| C26H22O2 | Z = 4 |
| Mr = 366.46 | Mo Kα radiation |
| Tetragonal, I41 | µ = 0.08 mm−1 |
| a = 11.7167 (9) Å | T = 298 K |
| c = 14.583 (2) Å | 0.20 × 0.18 × 0.14 mm |
| V = 2001.9 (4) Å3 |
| Rigaku SCXmini diffractometer | 1024 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 806 reflections with I > 2σ(I) |
| Tmin = 0.892, Tmax = 0.990 | Rint = 0.045 |
| 5346 measured reflections |
| R[F2 > 2σ(F2)] = 0.037 | 1 restraint |
| wR(F2) = 0.095 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.14 e Å−3 |
| 1024 reflections | Δρmin = −0.12 e Å−3 |
| 127 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| C9 | 0.3589 (2) | 0.0005 (2) | 0.65091 (16) | 0.0410 (6) | |
| C1 | 0.4419 (2) | −0.0269 (2) | 0.71920 (16) | 0.0406 (6) | |
| C10 | 0.2494 (2) | −0.0516 (2) | 0.65478 (17) | 0.0419 (6) | |
| O1 | 0.49556 (16) | −0.12473 (17) | 0.85183 (13) | 0.0557 (5) | |
| C7 | 0.2987 (2) | 0.1036 (2) | 0.51508 (19) | 0.0571 (8) | |
| H7A | 0.3147 | 0.1559 | 0.4688 | 0.068* | |
| C2 | 0.4132 (2) | −0.1021 (2) | 0.78793 (19) | 0.0451 (6) | |
| C4 | 0.2253 (2) | −0.1283 (2) | 0.72628 (18) | 0.0490 (6) | |
| H4A | 0.1537 | −0.1624 | 0.7293 | 0.059* | |
| C8 | 0.3794 (2) | 0.0793 (2) | 0.57953 (19) | 0.0486 (6) | |
| H8A | 0.4499 | 0.1155 | 0.5764 | 0.058* | |
| C3 | 0.3047 (2) | −0.1536 (2) | 0.79115 (19) | 0.0499 (7) | |
| H3A | 0.2873 | −0.2049 | 0.8377 | 0.060* | |
| C5 | 0.1674 (2) | −0.0254 (3) | 0.5868 (2) | 0.0540 (7) | |
| H5A | 0.0961 | −0.0602 | 0.5888 | 0.065* | |
| C6 | 0.1911 (2) | 0.0498 (3) | 0.5184 (2) | 0.0597 (8) | |
| H6A | 0.1366 | 0.0658 | 0.4738 | 0.072* | |
| C11 | 0.4636 (3) | −0.1789 (3) | 0.9343 (2) | 0.0687 (9) | |
| H11A | 0.4433 | −0.2578 | 0.9224 | 0.082* | |
| H11B | 0.3979 | −0.1408 | 0.9607 | 0.082* | |
| C12 | 0.5612 (4) | −0.1738 (3) | 0.9988 (3) | 0.0834 (11) | |
| H12A | 0.5519 | −0.2102 | 1.0550 | 0.100* | |
| C13 | 0.6573 (4) | −0.1243 (4) | 0.9849 (3) | 0.0976 (13) | |
| H13C | 0.6709 | −0.0868 | 0.9298 | 0.117* | |
| H13A | 0.7135 | −0.1259 | 1.0300 | 0.117* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C9 | 0.0387 (14) | 0.0427 (14) | 0.0415 (14) | 0.0017 (11) | 0.0029 (11) | −0.0071 (12) |
| C1 | 0.0377 (13) | 0.0424 (14) | 0.0419 (13) | −0.0010 (11) | 0.0017 (12) | −0.0031 (12) |
| C10 | 0.0335 (14) | 0.0452 (14) | 0.0470 (14) | 0.0019 (12) | 0.0042 (12) | −0.0120 (12) |
| O1 | 0.0517 (11) | 0.0685 (13) | 0.0468 (10) | −0.0008 (10) | −0.0022 (9) | 0.0134 (10) |
| C7 | 0.0595 (18) | 0.0593 (18) | 0.0524 (17) | 0.0089 (15) | −0.0030 (14) | 0.0075 (14) |
| C2 | 0.0455 (14) | 0.0467 (14) | 0.0430 (13) | 0.0033 (12) | 0.0010 (13) | −0.0022 (12) |
| C4 | 0.0389 (14) | 0.0541 (15) | 0.0539 (15) | −0.0053 (13) | 0.0104 (13) | −0.0073 (13) |
| C8 | 0.0422 (15) | 0.0506 (15) | 0.0529 (15) | 0.0006 (12) | 0.0003 (13) | 0.0025 (13) |
| C3 | 0.0504 (15) | 0.0525 (15) | 0.0468 (14) | −0.0058 (13) | 0.0108 (14) | 0.0037 (13) |
| C5 | 0.0372 (15) | 0.0618 (17) | 0.0630 (18) | 0.0028 (13) | −0.0016 (14) | −0.0109 (16) |
| C6 | 0.0495 (17) | 0.074 (2) | 0.0556 (17) | 0.0094 (15) | −0.0096 (15) | −0.0009 (16) |
| C11 | 0.085 (2) | 0.073 (2) | 0.0484 (17) | −0.0002 (18) | 0.0014 (17) | 0.0169 (16) |
| C12 | 0.106 (3) | 0.085 (3) | 0.0588 (19) | 0.004 (2) | −0.020 (2) | 0.0141 (19) |
| C13 | 0.106 (3) | 0.089 (3) | 0.098 (3) | 0.001 (3) | −0.044 (3) | 0.005 (3) |
| C9—C8 | 1.411 (4) | C4—H4A | 0.93 |
| C9—C10 | 1.422 (3) | C8—H8A | 0.93 |
| C9—C1 | 1.428 (3) | C3—H3A | 0.93 |
| C1—C2 | 1.376 (3) | C5—C6 | 1.360 (4) |
| C1—C1i | 1.500 (5) | C5—H5A | 0.93 |
| C10—C4 | 1.405 (4) | C6—H6A | 0.93 |
| C10—C5 | 1.415 (4) | C11—C12 | 1.482 (5) |
| O1—C2 | 1.368 (3) | C11—H11A | 0.97 |
| O1—C11 | 1.411 (4) | C11—H11B | 0.97 |
| C7—C8 | 1.363 (4) | C12—C13 | 1.282 (5) |
| C7—C6 | 1.410 (4) | C12—H12A | 0.93 |
| C7—H7A | 0.93 | C13—H13C | 0.93 |
| C2—C3 | 1.408 (4) | C13—H13A | 0.93 |
| C4—C3 | 1.359 (4) | ||
| C8—C9—C10 | 117.6 (2) | C4—C3—C2 | 120.1 (3) |
| C8—C9—C1 | 123.1 (2) | C4—C3—H3A | 120.0 |
| C10—C9—C1 | 119.3 (2) | C2—C3—H3A | 120.0 |
| C2—C1—C9 | 119.0 (2) | C6—C5—C10 | 121.0 (3) |
| C2—C1—C1i | 119.4 (2) | C6—C5—H5A | 119.5 |
| C9—C1—C1i | 121.6 (2) | C10—C5—H5A | 119.5 |
| C4—C10—C5 | 121.5 (2) | C5—C6—C7 | 119.8 (3) |
| C4—C10—C9 | 119.0 (2) | C5—C6—H6A | 120.1 |
| C5—C10—C9 | 119.5 (2) | C7—C6—H6A | 120.1 |
| C2—O1—C11 | 118.8 (2) | O1—C11—C12 | 108.6 (3) |
| C8—C7—C6 | 120.2 (3) | O1—C11—H11A | 110.0 |
| C8—C7—H7A | 119.9 | C12—C11—H11A | 110.0 |
| C6—C7—H7A | 119.9 | O1—C11—H11B | 110.0 |
| O1—C2—C1 | 116.6 (2) | C12—C11—H11B | 110.0 |
| O1—C2—C3 | 122.1 (2) | H11A—C11—H11B | 108.4 |
| C1—C2—C3 | 121.3 (2) | C13—C12—C11 | 126.6 (4) |
| C3—C4—C10 | 121.2 (2) | C13—C12—H12A | 116.7 |
| C3—C4—H4A | 119.4 | C11—C12—H12A | 116.7 |
| C10—C4—H4A | 119.4 | C12—C13—H13C | 120.0 |
| C7—C8—C9 | 121.8 (3) | C12—C13—H13A | 120.0 |
| C7—C8—H8A | 119.1 | H13C—C13—H13A | 120.0 |
| C9—C8—H8A | 119.1 | ||
| C8—C9—C1—C2 | 178.0 (2) | C5—C10—C4—C3 | 179.6 (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—C9 | 0.0 (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—C7 | 179.8 (2) |
| C1—C9—C10—C4 | 0.4 (3) | C10—C4—C3—C2 | 0.4 (4) |
| C8—C9—C10—C5 | 1.7 (3) | O1—C2—C3—C4 | 179.8 (2) |
| C1—C9—C10—C5 | −179.4 (2) | C1—C2—C3—C4 | −0.9 (4) |
| C11—O1—C2—C1 | 165.4 (2) | C4—C10—C5—C6 | 179.3 (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—C5 | 0.9 (4) |
| C9—C1—C2—C3 | 1.1 (3) | C2—O1—C11—C12 | −169.1 (2) |
| C1i—C1—C2—C3 | 179.3 (3) | O1—C11—C12—C13 | 3.0 (5) |
| Symmetry code: (i) −x+1, −y, z. |
Experimental details
| Crystal data | |
| Chemical formula | C26H22O2 |
| Mr | 366.46 |
| Crystal system, space group | Tetragonal, I41 |
| Temperature (K) | 298 |
| a, c (Å) | 11.7167 (9), 14.583 (2) |
| V (Å3) | 2001.9 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.08 |
| Crystal size (mm) | 0.20 × 0.18 × 0.14 |
| Data collection | |
| Diffractometer | Rigaku SCXmini diffractometer |
| Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
| Tmin, Tmax | 0.892, 0.990 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5346, 1024, 806 |
| Rint | 0.045 |
| (sin θ/λ)max (Å−1) | 0.616 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.02 |
| No. of reflections | 1024 |
| No. of parameters | 127 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 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
Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317. Web of Science CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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.