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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o317.
Published online 2007 December 21. doi:  10.1107/S1600536807066718
PMCID: PMC2915361

2,2′-Bis(prop-2-yn­yloxy)-1,1′-binaphth­yl

Abstract

In the title compound, C26H18O2, the mol­ecule is located on a twofold rotation axis. The two naphthyl ring planes in the mol­ecule are nearly perpendicular to each other [dihedral angle = 82.42 (1)°. No classical hydrogen bonds or aromatic π–π stacking inter­actions were observed.

Related literature

For related literature, see: Burchell et al. (2006 [triangle]); Steed & Atwood (2000 [triangle]); Wang & Kong (2007 [triangle]).

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Object name is e-64-0o317-scheme1.jpg

Experimental

Crystal data

  • C26H18O2
  • M r = 362.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o317-efi1.jpg
  • a = 13.866 (2) Å
  • b = 8.8591 (14) Å
  • c = 15.255 (2) Å
  • β = 96.317 (3)°
  • V = 1862.6 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 6053 measured reflections
  • 2298 independent reflections
  • 1321 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.139
  • S = 0.95
  • 2298 reflections
  • 127 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2005 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066718/rk2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066718/rk2069Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Henan Administration of Science and Technology (grant No. 0111030700).

supplementary crystallographic information

Comment

The title compound, C26H18O2, was obtained unintentionally as the product of an attempted synthesis of a network complex of cobalt(II) with 2,2'-bis(prop-2-ynyloxy)-1,1'-binaphthyl.

The title compound has two naphthyl rings. The bond lengths and angles show normal values. The dihedral angle between the two naphthyl rings of the molecule is 82.42 (1) °.

It seems like that the π-π stacking interaction is a normal interaction found in aromatics (Wang & Kong, 2007). But in the structure of the title complex, the minimal distance between ring centroids is 3.795 (1) Å. So there is no π-π stacking interactions (Steed & Atwood, 2000). The classic hydrogen bonds are not observed.

Experimental

The title compound was obtained unintentionally as the product of an attempted synthesis of a network complex (Burchell et al., 2006) of cobalt(II) with 2,2'-bis(prop-2-ynyloxy)-1,1'-binaphthyl, vapouring an methyl alcohol and acetone solution of cobalt(II) chloride, sodium azide and the title compound at room temperature.

Refinement

All H atoms were placed in calculated positions with C–H distances 0.93 and 0.97 Å and refined in the riding-model approximation with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title complound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
Fig. 2.
The molecular packing of the title compound.

Crystal data

C26H18O2F000 = 760
Mr = 362.40Dx = 1.292 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1326 reflections
a = 13.866 (2) Åθ = 5.4–55.7º
b = 8.8591 (14) ŵ = 0.08 mm1
c = 15.255 (2) ÅT = 293 (2) K
β = 96.317 (3)ºBlock, colourless
V = 1862.6 (5) Å30.22 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer1321 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Monochromator: graphiteθmax = 28.3º
T = 293(2) Kθmin = 2.7º
[var phi]– and ω–scansh = −18→13
Absorption correction: nonek = −11→11
6053 measured reflectionsl = −19→20
2298 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
2298 reflectionsΔρmax = 0.29 e Å3
127 parametersΔρmin = −0.17 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C10.53783 (11)0.02688 (17)0.28936 (9)0.0337 (4)
C20.53225 (11)−0.07606 (18)0.36043 (9)0.0351 (4)
C30.45901 (12)−0.18646 (19)0.36016 (11)0.0445 (4)
H30.4137−0.19650.31080.053*
C40.45339 (14)−0.2796 (2)0.43149 (12)0.0541 (5)
H40.4044−0.35160.42990.065*
C50.52108 (14)−0.2670 (2)0.50676 (12)0.0548 (5)
H50.5161−0.32900.55520.066*
C60.59366 (13)−0.1641 (2)0.50849 (10)0.0483 (5)
H60.6385−0.15700.55840.058*
C70.60280 (12)−0.06741 (18)0.43620 (10)0.0378 (4)
C80.67634 (12)0.04140 (19)0.43727 (10)0.0422 (4)
H80.72300.04690.48590.051*
C90.68140 (12)0.13914 (19)0.36920 (10)0.0416 (4)
H90.73080.21050.37160.050*
C100.61115 (12)0.13157 (18)0.29481 (9)0.0364 (4)
O10.61167 (9)0.22689 (14)0.22387 (7)0.0499 (4)
C110.68206 (13)0.3446 (2)0.22703 (11)0.0506 (5)
H11A0.68070.38950.16890.061*
H11B0.74600.30140.24210.061*
C120.66649 (14)0.4617 (2)0.29005 (12)0.0520 (5)
C130.65408 (17)0.5555 (3)0.34144 (16)0.0713 (6)
H130.64420.63020.38230.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0369 (9)0.0350 (9)0.0278 (7)0.0026 (7)−0.0028 (6)−0.0025 (7)
C20.0364 (9)0.0369 (9)0.0309 (8)0.0056 (7)−0.0007 (6)−0.0006 (7)
C30.0424 (10)0.0470 (10)0.0422 (9)−0.0026 (8)−0.0040 (7)0.0048 (8)
C40.0505 (12)0.0554 (12)0.0560 (11)−0.0054 (9)0.0044 (9)0.0092 (9)
C50.0629 (13)0.0583 (12)0.0433 (10)0.0080 (10)0.0060 (9)0.0155 (9)
C60.0547 (11)0.0561 (12)0.0320 (9)0.0080 (9)−0.0045 (7)0.0042 (8)
C70.0420 (10)0.0394 (9)0.0305 (8)0.0089 (7)−0.0027 (7)−0.0010 (7)
C80.0411 (10)0.0492 (10)0.0330 (8)0.0055 (8)−0.0112 (7)−0.0040 (8)
C90.0393 (9)0.0441 (10)0.0394 (9)−0.0039 (8)−0.0052 (7)−0.0047 (8)
C100.0424 (9)0.0363 (9)0.0295 (8)0.0007 (7)−0.0002 (7)−0.0022 (7)
O10.0598 (8)0.0502 (8)0.0370 (6)−0.0170 (6)−0.0072 (5)0.0071 (5)
C110.0564 (12)0.0485 (11)0.0465 (10)−0.0137 (9)0.0045 (8)0.0027 (9)
C120.0570 (12)0.0418 (11)0.0563 (11)−0.0049 (9)0.0032 (9)0.0027 (10)
C130.0842 (17)0.0549 (14)0.0746 (14)0.0047 (11)0.0083 (12)−0.0089 (12)

Geometric parameters (Å, °)

C1—C101.372 (2)C7—C81.402 (2)
C1—C21.425 (2)C8—C91.360 (2)
C1—C1i1.505 (3)C8—H80.9300
C2—C31.410 (2)C9—C101.413 (2)
C2—C71.432 (2)C9—H90.9300
C3—C41.375 (2)C10—O11.3734 (18)
C3—H30.9300O1—C111.425 (2)
C4—C51.405 (3)C11—C121.447 (2)
C4—H40.9300C11—H11A0.9700
C5—C61.356 (3)C11—H11B0.9700
C5—H50.9300C12—C131.168 (3)
C6—C71.413 (2)C13—H130.9300
C6—H60.9300
C10—C1—C2119.23 (13)C6—C7—C2119.05 (16)
C10—C1—C1i119.68 (13)C9—C8—C7121.84 (14)
C2—C1—C1i121.03 (13)C9—C8—H8119.1
C3—C2—C1122.77 (14)C7—C8—H8119.1
C3—C2—C7117.86 (14)C8—C9—C10119.60 (15)
C1—C2—C7119.37 (14)C8—C9—H9120.2
C4—C3—C2121.19 (15)C10—C9—H9120.2
C4—C3—H3119.4C1—C10—O1115.85 (13)
C2—C3—H3119.4C1—C10—C9121.43 (14)
C3—C4—C5120.53 (17)O1—C10—C9122.72 (14)
C3—C4—H4119.7C10—O1—C11119.09 (12)
C5—C4—H4119.7O1—C11—C12113.29 (15)
C6—C5—C4119.80 (17)O1—C11—H11A108.9
C6—C5—H5120.1C12—C11—H11A108.9
C4—C5—H5120.1O1—C11—H11B108.9
C5—C6—C7121.50 (16)C12—C11—H11B108.9
C5—C6—H6119.3H11A—C11—H11B107.7
C7—C6—H6119.3C13—C12—C11179.5 (2)
C8—C7—C6122.37 (15)C12—C13—H13180.0
C8—C7—C2118.53 (14)
C10—C1—C2—C3179.70 (15)C1—C2—C7—C6176.48 (15)
C1i—C1—C2—C32.5 (2)C6—C7—C8—C9−176.48 (15)
C10—C1—C2—C70.4 (2)C2—C7—C8—C90.9 (2)
C1i—C1—C2—C7−176.80 (14)C7—C8—C9—C10−0.2 (2)
C1—C2—C3—C4−177.15 (16)C2—C1—C10—O1−179.93 (13)
C7—C2—C3—C42.1 (2)C1i—C1—C10—O1−2.7 (2)
C2—C3—C4—C5−0.1 (3)C2—C1—C10—C90.2 (2)
C3—C4—C5—C6−1.3 (3)C1i—C1—C10—C9177.49 (15)
C4—C5—C6—C70.5 (3)C8—C9—C10—C1−0.4 (2)
C5—C6—C7—C8178.90 (17)C8—C9—C10—O1179.83 (15)
C5—C6—C7—C21.6 (3)C1—C10—O1—C11176.21 (15)
C3—C2—C7—C8179.73 (15)C9—C10—O1—C11−4.0 (2)
C1—C2—C7—C8−0.9 (2)C10—O1—C11—C12−68.9 (2)
C3—C2—C7—C6−2.8 (2)

Symmetry codes: (i) −x+1, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2069).

References

  • Bruker (2005). APEX2, SAINT and SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burchell, T. J., Jennings, M. C. & Puddephatt, R. J. (2006). Inorg. Chim. Acta, 359, 2812–2818.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Steed, J. W. & Atwood, J. L. (2000). Supramolecular Chemistry, p. 26. Chichester: John Wiley & Sons.
  • Wang, X.-B. & Kong, L.-Y. (2007). Acta Cryst. E63, o4340.

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