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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.139
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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.

Related literature

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

S2. 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.

S3. 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 U_iso(H) = 1.2U_eq(C).

Computing details

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

	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

Crystal data

C26H18O2	F(000) = 760
Mr = 362.40	Dx = 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) Å^3	0.22 × 0.18 × 0.16 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.068P)^2] where P = (Fo^2 + 2Fc^2)/3
2298 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3
0 constraints

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

C1—C10	1.372 (2)	C7—C8	1.402 (2)
C1—C2	1.425 (2)	C8—C9	1.360 (2)
C1—C1^i	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—C1^i	119.68 (13)	C9—C8—C7	121.84 (14)
C2—C1—C1^i	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)
C1^i—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)
C1^i—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)	C1^i—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)	C1^i—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.