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

Jian, C.; Zhang, J.; Wang, L.; Tang, N.; Wu, J.

doi:10.1107/S1600536812051938

Volume 69
Part 2
Page o186
February 2013

Received 21 December 2012
Accepted 27 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.074
wR = 0.205
Data-to-parameter ratio = 19.6
Details

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 and Jincai Wu ^a ^*

^aDepartment of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
Correspondence e-mail: wujc@lzu.edu.cn

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-HO_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-HO 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, $[P \overline 1]$
a = 9.885 (2) Å
b = 12.948 (3) Å
c = 13.600 (3) Å
= 101.761 (2)°
= 102.539 (2)°
= 92.004 (2)°
V = 1657.8 (6) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.205
S = 0.99
7609 reflections
389 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO4	0.82	2.59	3.322 (4)	149
C24-H24CO3ⁱ	0.96	2.67	3.372 (4)	130
C25-H25CO4ⁱⁱ	0.96	2.64	3.500 (4)	150
C20-H20BO3ⁱⁱ	0.96	2.69	3.609 (5)	160
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: CV5377 ).

Acknowledgements

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

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, C. & Wu, J. (2012). Acta Cryst. E68, o93.
Wu, J., Pan, X., Wang, L. & Yao, L. (2009). Acta Cryst. E65, o155.
Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.

organic compounds