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

The complete mol-ecule of the title compound, C(26)H(22)O(2), 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 inter-actions are observed.

Related literature

For related structures, see: Fu & Zhao (2007 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C26H22O2

M = 366.46

Tetragonal,

a = 11.7167 (9) Å

c = 14.583 (2) Å

V = 2001.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.18 × 0.14 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.892, T max = 0.990

5346 measured reflections

1024 independent reflections

806 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.02

1024 reflections

127 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015815/ci2788sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015815/ci2788Isup2.hkl

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

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	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

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)