3,3′,5,5′-Tetra-tert-butyl-2′-hy­droxy-[1,1′-biphen­yl]-2-yl 4-methyl­benzene­sulfonate

Chunli Jian; Jinjin Zhang; Lei Wang; Ning Tang; Jincai Wu

doi:10.1107/S1600536812051938

. 2013 Jan 4;69(Pt 2):o186. doi: 10.1107/S1600536812051938

3,3′,5,5′-Tetra-tert-butyl-2′-hydroxy-[1,1′-biphenyl]-2-yl 4-methylbenzenesulfonate

Chunli Jian ^a, Jinjin Zhang ^a, Lei Wang ^a, Ning Tang ^a, Jincai Wu ^a,^*

PMCID: PMC3569248 PMID: 23424471

Abstract

In the title molecule, C₃₇H₄₈O₄S, the benzene rings in the biphenyl fragment are inclined to each other at 61.1 (1)°. The hydroxy group is involved in a weak intramolecular O—H⋯O_sulfonate hydrogen bond. One tert-butyl group is disodered over two orientations in a 0.682 (17):0.318 (17) ratio. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into columns in direction [100].

Related literature

For applications of coordination complexes with close ligands in the ring-opening polymerization of cyclic esters, see: Wu et al. (2006 ▶). For the crystal structures of related compounds, see: Wu et al. (2009 ▶); Wang & Wu (2012 ▶).

Experimental

Crystal data

C₃₅H₄₈O₄S
M _r = 564.79
Triclinic,
a = 9.885 (2) Å
b = 12.948 (3) Å
c = 13.600 (3) Å
α = 101.761 (2)°
β = 102.539 (2)°
γ = 92.004 (2)°
V = 1657.8 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) ▶ T _min = 0.965, T _max = 0.973
11516 measured reflections
7609 independent reflections
3453 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.205
S = 0.99
7609 reflections
389 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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

Click here for additional data file.^{(30.8KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051938/cv5377sup1.cif

e-69-0o186-sup1.cif^{(30.8KB, cif)}

Click here for additional data file.^{(372.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051938/cv5377Isup2.hkl

e-69-0o186-Isup2.hkl^{(372.2KB, hkl)}

Click here for additional data file.^{(10.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812051938/cv5377Isup3.cml

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
O2—H2A⋯O4	0.82	2.59	3.322 (4)	149
C24—H24C⋯O3ⁱ	0.96	2.67	3.372 (4)	130
C25—H25C⋯O4ⁱⁱ	0.96	2.64	3.500 (4)	150
C20—H20B⋯O3ⁱⁱ	0.96	2.69	3.609 (5)	160

Open in a new tab

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

Acknowledgments

We thank the National Natural Science Foundation of China (grant Nos. 21071069, 21171078 and 21271092) for financial support.

supplementary crystallographic information

Comment

Polyesters as potentially valuable "green plastics" are attracting increasing attention. Many coordination complexes have been designed and synthesized as initiators or catalysts for the ring-opening polymerization of cyclic esters (Wu et al., 2006). Herewith we present the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Wu et al., 2009; Wang et al., 2012). Two benzene rings in the biphenyl fragment are inclined to each other at 61.1 (1)°. The hydroxy group is involved in a weak intramolecular O2—H2A···O4 hydrogen bond (Table 1). In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into columns in [100].

Experimental

This title compound was synthesized by condensation of 3,3',5,5'-tetra-tert-butyl-[1,1'-biphenyl]-2,2'-diol and and 4- methylbenzene-1-sulfonyl chloride in dichloromethane at 0°C for about 1 h in the presence of 10 equiv. triethylamine. The crystals were obtained by slow cooling a hexane solution.