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

Zhang, W.; Cui, Q.; Yu, Z.

doi:10.1107/S1600536807066718

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o317

https://doi.org/10.1107/S1600536807066718

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

Wu Zhang,^a ^* Qingxia Cui ^a and Zhaowen Yu ^a

^aInstitute of Molecular and Crystal Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China
^*Correspondence e-mail: zhw@henu.edu.cn

(Received 17 November 2007; accepted 12 December 2007; online 21 December 2007)

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 ); Steed & Atwood (2000 ); Wang & Kong (2007 ).

Experimental

Crystal data

C₂₆H₁₈O₂
M_r = 362.40
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.139
S = 0.95
2298 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066718/rk2069Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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) °.

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

Computing details top

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

Figures top

	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.

2,2'-Bis(prop-2-ynyloxy)-1,1'-binaphthyl top

Crystal data top

C₂₆H₁₈O₂	F(000) = 760
M_r = 362.40	D_x = 1.292 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1326 reflections
a = 13.866 (2) Å	θ = 5.4–55.7°
b = 8.8591 (14) Å	µ = 0.08 mm⁻¹
c = 15.255 (2) Å	T = 293 K
β = 96.317 (3)°	Block, colourless
V = 1862.6 (5) Å³	0.22 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1321 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 28.3°, θ_min = 2.7°
φ– and ω–scans	h = −18→13
6053 measured reflections	k = −11→11
2298 independent reflections	l = −19→20

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.068P)²] where P = (F_o² + 2F_c²)/3
2298 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³
0 constraints

Crystal data top

C₂₆H₁₈O₂	V = 1862.6 (5) Å³
M_r = 362.40	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.866 (2) Å	µ = 0.08 mm⁻¹
b = 8.8591 (14) Å	T = 293 K
c = 15.255 (2) Å	0.22 × 0.18 × 0.16 mm
β = 96.317 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1321 reflections with I > 2σ(I)
6053 measured reflections	R_int = 0.058
2298 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 0.95	Δρ_max = 0.29 e Å⁻³
2298 reflections	Δρ_min = −0.17 e Å⁻³
127 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.53783 (11)	0.02688 (17)	0.28936 (9)	0.0337 (4)
C2	0.53225 (11)	−0.07606 (18)	0.36043 (9)	0.0351 (4)
C3	0.45901 (12)	−0.18646 (19)	0.36016 (11)	0.0445 (4)
H3	0.4137	−0.1965	0.3108	0.053*
C4	0.45339 (14)	−0.2796 (2)	0.43149 (12)	0.0541 (5)
H4	0.4044	−0.3516	0.4299	0.065*
C5	0.52108 (14)	−0.2670 (2)	0.50676 (12)	0.0548 (5)
H5	0.5161	−0.3290	0.5552	0.066*
C6	0.59366 (13)	−0.1641 (2)	0.50849 (10)	0.0483 (5)
H6	0.6385	−0.1570	0.5584	0.058*
C7	0.60280 (12)	−0.06741 (18)	0.43620 (10)	0.0378 (4)
C8	0.67634 (12)	0.04140 (19)	0.43727 (10)	0.0422 (4)
H8	0.7230	0.0469	0.4859	0.051*
C9	0.68140 (12)	0.13914 (19)	0.36920 (10)	0.0416 (4)
H9	0.7308	0.2105	0.3716	0.050*
C10	0.61115 (12)	0.13157 (18)	0.29481 (9)	0.0364 (4)
O1	0.61167 (9)	0.22689 (14)	0.22387 (7)	0.0499 (4)
C11	0.68206 (13)	0.3446 (2)	0.22703 (11)	0.0506 (5)
H11A	0.6807	0.3895	0.1689	0.061*
H11B	0.7460	0.3014	0.2421	0.061*
C12	0.66649 (14)	0.4617 (2)	0.29005 (12)	0.0520 (5)
C13	0.65408 (17)	0.5555 (3)	0.34144 (16)	0.0713 (6)
H13	0.6442	0.6302	0.3823	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (9)	0.0350 (9)	0.0278 (7)	0.0026 (7)	−0.0028 (6)	−0.0025 (7)
C2	0.0364 (9)	0.0369 (9)	0.0309 (8)	0.0056 (7)	−0.0007 (6)	−0.0006 (7)
C3	0.0424 (10)	0.0470 (10)	0.0422 (9)	−0.0026 (8)	−0.0040 (7)	0.0048 (8)
C4	0.0505 (12)	0.0554 (12)	0.0560 (11)	−0.0054 (9)	0.0044 (9)	0.0092 (9)
C5	0.0629 (13)	0.0583 (12)	0.0433 (10)	0.0080 (10)	0.0060 (9)	0.0155 (9)
C6	0.0547 (11)	0.0561 (12)	0.0320 (9)	0.0080 (9)	−0.0045 (7)	0.0042 (8)
C7	0.0420 (10)	0.0394 (9)	0.0305 (8)	0.0089 (7)	−0.0027 (7)	−0.0010 (7)
C8	0.0411 (10)	0.0492 (10)	0.0330 (8)	0.0055 (8)	−0.0112 (7)	−0.0040 (8)
C9	0.0393 (9)	0.0441 (10)	0.0394 (9)	−0.0039 (8)	−0.0052 (7)	−0.0047 (8)
C10	0.0424 (9)	0.0363 (9)	0.0295 (8)	0.0007 (7)	−0.0002 (7)	−0.0022 (7)
O1	0.0598 (8)	0.0502 (8)	0.0370 (6)	−0.0170 (6)	−0.0072 (5)	0.0071 (5)
C11	0.0564 (12)	0.0485 (11)	0.0465 (10)	−0.0137 (9)	0.0045 (8)	0.0027 (9)
C12	0.0570 (12)	0.0418 (11)	0.0563 (11)	−0.0049 (9)	0.0032 (9)	0.0027 (10)
C13	0.0842 (17)	0.0549 (14)	0.0746 (14)	0.0047 (11)	0.0083 (12)	−0.0089 (12)

Geometric parameters (Å, º) top

C1—C10	1.372 (2)	C7—C8	1.402 (2)
C1—C2	1.425 (2)	C8—C9	1.360 (2)
C1—C1ⁱ	1.505 (3)	C8—H8	0.9300
C2—C3	1.410 (2)	C9—C10	1.413 (2)
C2—C7	1.432 (2)	C9—H9	0.9300
C3—C4	1.375 (2)	C10—O1	1.3734 (18)
C3—H3	0.9300	O1—C11	1.425 (2)
C4—C5	1.405 (3)	C11—C12	1.447 (2)
C4—H4	0.9300	C11—H11A	0.9700
C5—C6	1.356 (3)	C11—H11B	0.9700
C5—H5	0.9300	C12—C13	1.168 (3)
C6—C7	1.413 (2)	C13—H13	0.9300
C6—H6	0.9300

C10—C1—C2	119.23 (13)	C6—C7—C2	119.05 (16)
C10—C1—C1ⁱ	119.68 (13)	C9—C8—C7	121.84 (14)
C2—C1—C1ⁱ	121.03 (13)	C9—C8—H8	119.1
C3—C2—C1	122.77 (14)	C7—C8—H8	119.1
C3—C2—C7	117.86 (14)	C8—C9—C10	119.60 (15)
C1—C2—C7	119.37 (14)	C8—C9—H9	120.2
C4—C3—C2	121.19 (15)	C10—C9—H9	120.2
C4—C3—H3	119.4	C1—C10—O1	115.85 (13)
C2—C3—H3	119.4	C1—C10—C9	121.43 (14)
C3—C4—C5	120.53 (17)	O1—C10—C9	122.72 (14)
C3—C4—H4	119.7	C10—O1—C11	119.09 (12)
C5—C4—H4	119.7	O1—C11—C12	113.29 (15)
C6—C5—C4	119.80 (17)	O1—C11—H11A	108.9
C6—C5—H5	120.1	C12—C11—H11A	108.9
C4—C5—H5	120.1	O1—C11—H11B	108.9
C5—C6—C7	121.50 (16)	C12—C11—H11B	108.9
C5—C6—H6	119.3	H11A—C11—H11B	107.7
C7—C6—H6	119.3	C13—C12—C11	179.5 (2)
C8—C7—C6	122.37 (15)	C12—C13—H13	180.0
C8—C7—C2	118.53 (14)

C10—C1—C2—C3	179.70 (15)	C1—C2—C7—C6	176.48 (15)
C1ⁱ—C1—C2—C3	2.5 (2)	C6—C7—C8—C9	−176.48 (15)
C10—C1—C2—C7	0.4 (2)	C2—C7—C8—C9	0.9 (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—C4	2.1 (2)	C1ⁱ—C1—C10—O1	−2.7 (2)
C2—C3—C4—C5	−0.1 (3)	C2—C1—C10—C9	0.2 (2)
C3—C4—C5—C6	−1.3 (3)	C1ⁱ—C1—C10—C9	177.49 (15)
C4—C5—C6—C7	0.5 (3)	C8—C9—C10—C1	−0.4 (2)
C5—C6—C7—C8	178.90 (17)	C8—C9—C10—O1	179.83 (15)
C5—C6—C7—C2	1.6 (3)	C1—C10—O1—C11	176.21 (15)
C3—C2—C7—C8	179.73 (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 code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈O₂
M_r	362.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	13.866 (2), 8.8591 (14), 15.255 (2)
β (°)	96.317 (3)
V (Å³)	1862.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6053, 2298, 1321
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.139, 0.95
No. of reflections	2298
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005).

Acknowledgements

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

References

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