2,2′,4,4′,6,6′-Hexamethyl­biphenyl-3,3′,5,5′-tetra­yltetra­methyl­ene tetra­acetate

Tuoping Hu

doi:10.1107/S1600536809018261

. 2009 May 20;65(Pt 6):o1355. doi: 10.1107/S1600536809018261

2,2′,4,4′,6,6′-Hexamethylbiphenyl-3,3′,5,5′-tetrayltetramethylene tetraacetate

Tuoping Hu ^a,^*

PMCID: PMC2969695 PMID: 21583206

Abstract

The title compound, C₃₀H₃₈O₈, possess C_i symmetry, with the inversion center situated at the center of the bridging C—C bond. In the crystal structure, molecules are held together by C—H⋯O interactions.

Related literature

For related structures, see: Frohlich & Musso (1985 ▶), Moorthy et al. (2002 ▶, 2005 ▶, 2006a ▶,b ▶); Natarajan et al. (2005a ▶,b ▶); Pickett (1936 ▶).

Experimental

Crystal data

C₃₀H₃₈O₈
M _r = 526.60
Orthorhombic,
a = 15.336 (2) Å
b = 12.658 (1) Å
c = 14.755 (2) Å
V = 2864.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.983, T _max = 0.991
8052 measured reflections
1709 independent reflections
1045 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.199
S = 1.02
1709 reflections
173 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018261/su2107sup1.cif

e-65-o1355-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018261/su2107Isup2.hkl

e-65-o1355-Isup2.hkl^{(82.5KB, 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
C15—H15A⋯O1ⁱ	0.96	2.58	3.472 (7)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author is grateful for funding support from the Natural Science Foundation of Shanxi Province (grant No. 2007011033), the Program for Technological Industrialization at the University of Shanxi Province (grant No. 20070308) and the start-up fund of the North University of China.

supplementary crystallographic information

Comment

The title compound, illustrated in Fig. 1, was obtained as a byproduct when preparing the first order dendrimer by using 2,2',4,4',6,6'-hexamethyl-3,3',5,5''-biphenylene- tetramethanol. The molecule possesses a centre of inversion situated at the center of the bridging C-C bond. The two benzene rings are almost perpendicular to one another, with a dihedral angle of 82.71 (2) °. The geometry and bond distances are close to those observed in similar structures (Frohlich et al., 1985); Moorthy et al., 2002, 2005, 2006a,b; Natarajan et al., 2005a,b; Pickett, 1936).

In the crystal structure of the title compound adjacent molecules have normal hydrophobic contacts with no intercalation or stacking interactions, only C-H···O interactions (Table 1 and Fig. 2).

Experimental

To (2,2',4,4',6,6'-trimethyl-1,1',3,3'-phenylene) tetramethanol (10 mmol, 3.585 mg), in 50 ml of CH₃COOH, was added 5 g of KOH. The mixture was stirred and heated at reflux for 24 h. The solution was then filtered, and the filtrate concentrated under vacumn. The sticky solid obtained was recrystalized in a mixture of benzene and acetone (1:1). Colourless prismatic crystals of the title compound were obtained. They were filtered, washed with cool diethylether and air dried.