2,2'-Bis(prop-2-yn-yloxy)-1,1'-binaphth-yl.

In the title compound, C(26)H(18)O(2), the mol-ecule is located on a twofold rotation axis. The two naphthyl ring planes in the mol-ecule are nearly perpendicular to each other [dihedral angle = 82.42 (1)°. No classical hydrogen bonds or aromatic π-π stacking inter-actions were observed.

Related literature

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

Experimental

Crystal data

C26H18O2

M = 362.40

Monoclinic,

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 ▶); 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.

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

C26H18O2	F000 = 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 = 5.4–55.7º
b = 8.8591 (14) Å	µ = 0.08 mm−1
c = 15.255 (2) Å	T = 293 (2) K
β = 96.317 (3)º	Block, colourless
V = 1862.6 (5) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1321 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Monochromator: graphite	θmax = 28.3º
T = 293(2) K	θmin = 2.7º
φ– and ω–scans	h = −18→13
Absorption correction: none	k = −11→11
6053 measured reflections	l = −19→20
2298 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-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 reflections	Δρmax = 0.29 e Å−3
127 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	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*

	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)

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)