Di-tert-Butyl 2,2′-[2,2′-methyl­enebis(naphthalene-2,1-diyldi­oxy)]diacetate

Qamar Ali; Itrat Anis; M Raza Shah; Seik Weng Ng

doi:10.1107/S1600536811003291

. 2011 Jan 29;67(Pt 2):o533. doi: 10.1107/S1600536811003291

Di-tert-Butyl 2,2′-[2,2′-methylenebis(naphthalene-2,1-diyldioxy)]diacetate

Qamar Ali ^a, Itrat Anis ^a, M Raza Shah ^a, Seik Weng Ng ^b,^*

PMCID: PMC3051626 PMID: 21523181

Abstract

In the title compound, C₃₃H₃₆O₆, two naphthalene ring systems are connected through a methylene linkage [C—C—C = 114.9 (2)°]; the ring systems are aligned at an angle of 76.5 (1)°. Of the two –O–CH₂–C(=O)–C(CH₃)₃ substituents, one adopts an extended conformation whereas the other is U-shaped. In the crystal, molecules are linked via weak C—H⋯O hydrogen bonding, forming supramolecular chains running along the c axis.

Related literature

For two related structures, see: Ali et al. (2008 ▶); Mustafa et al. (2009 ▶).

Experimental

Crystal data

C₃₃H₃₆O₆
M _r = 528.62
Triclinic,
a = 8.9849 (5) Å
b = 11.8327 (6) Å
c = 13.7768 (6) Å
α = 79.804 (4)°
β = 74.115 (4)°
γ = 88.094 (4)°
V = 1386.33 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.744, T _max = 1.000
11166 measured reflections
6119 independent reflections
3422 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.171
S = 1.03
6119 reflections
353 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003291/xu5152sup1.cif

e-67-0o533-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003291/xu5152Isup2.hkl

e-67-0o533-Isup2.hkl^{(299.5KB, 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
C4—H4B⋯O5ⁱ	0.98	2.46	3.419 (3)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The crystal structure (Scheme I) continues from the studies on di-tert-butyl 2,2'-(biphenyl-2,2,'-diyldioxy)diacetate (Ali et al., 2008) and di-tert-butyl (1,1'-binaphthyl-2,2'-dioxy)diacetate (Mustafa et al., 2009). The title compound has two naphthyl ring systems connected through a methylene linkage [C–C–C 114.9 (2)°] (Fig. 1); the rings are aligned at a dihedral angle of 76.5 (1)°. In the crystal structure the molecules are linked via weak C—H···O hydrogen bonding to form one dimensional supra-molecular chains running along the c axis (Table 1).

Experimental

1,1'-Methylenedi-2-naphthol (1 g, 3.3 mmol) was dissolved in acetone (25 ml). To the solution was added potassium cabonate (13.2 mmol) and t-butyl bromoacetate (3 ml, 19.8 mmol). The mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The aqueous layer was extracted three times with dichloromethane. The combined organic phases were evaporated under reduced pressure and the solid material was recrystallized from n-hexane.