2,2′-Bis(meth­oxy­meth­oxy)-3,3′-diphenyl-1,1′-binaphthalene

Hua Zong; Hua-Yin Huang; Bing Hu; Guang-Ling Bian; Ling Song

doi:10.1107/S1600536810053018

. 2010 Dec 24;67(Pt 1):o222. doi: 10.1107/S1600536810053018

2,2′-Bis(methoxymethoxy)-3,3′-diphenyl-1,1′-binaphthalene

Hua Zong ^a, Hua-Yin Huang ^a, Bing Hu ^a, Guang-Ling Bian ^a, Ling Song ^a,^*

PMCID: PMC3050160 PMID: 21522721

Abstract

The asymmetric unit of the title compound, C₃₆H₃₀O₄, contains two crystallographically independent molecules of similar geometry. In both molecules, the methoxymethoxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). The dihedral angles between the naphthalene planes within the same molecule are 71.72 (7) and 71.73 (8)°. In the crystal, neighbouring molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming double chains parallel to the c axis.

Related literature

For the application of 1,1′-bi-2-naphthol derivatives in asymmetric syntheses, see: Lou et al. (2006 ▶); Brunel (2006 ▶). For the synthesis of the title compound, see: Wu et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₃₆H₃₀O₄
M _r = 526.60
Monoclinic,
a = 11.3166 (3) Å
b = 19.4841 (3) Å
c = 14.0155 (4) Å
β = 110.172 (3)°
V = 2900.77 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.43 × 0.40 × 0.36 mm

Data collection

Oxford Xcalibur Eos CCD diffractometer
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006 ▶) T _min = 0.828, T _max = 1.000
12553 measured reflections
6211 independent reflections
4315 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.069
S = 1.01
6211 reflections
769 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053018/rz2537sup1.cif

e-67-0o222-sup1.cif^{(40.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053018/rz2537Isup2.hkl

e-67-0o222-Isup2.hkl^{(304KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O6Aⁱ	0.93	2.59	3.448 (6)	153
C43—H43A⋯O2Bⁱⁱ	0.93	2.57	3.304 (7)	136
C51—H51A⋯O1	0.93	2.38	3.233 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the Natural Science Foundation of Fujian province (No. 2010 J01055) for financial support.

supplementary crystallographic information

Comment

Chiral compounds especially when used as chiral ligands are particularly important in asymmteric synthesis. 1,1'-Bi-2-naphthol (BINOL) and its derivatives have been widely used in asymmetric synthesis (Lou et al., 2006; Brunel, 2006), and used as effective chiral ligands for various metal complex catalysis. As part of our research in this field, we synthesized the title compound, whose X-ray crystal structure is reported herein.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). In both molecules, the methoxymethoxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angles between the naphthalene planes belonging to the same molecule are 71.72 (7)° and 71.73 (8)°. In the crystal structure, intramolecular C—H···O hydrogen bonds (Table 1) assemble neighbouring molecule into double chains running parallel to the c axis (Fig. 2).

Experimental

The title compound was prepared by the reaction of (R,R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene and phenylboronic acid according to the literature method (Wu et al., 2004). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (1.5 g) in ethyl acetate (20 ml) and evaporating the solvent slowly at room temperature for about 28 h.