2,4-Di-tert-butyl-6-[(R/S)-1-(3,5-di-tert-butyl-2-hy­droxy­phen­yl)eth­yl]phenyl [(1R,4S)-7,7-dimethyl-2-oxobicyclo­[2.2.1]heptan-1-yl]methane­sulfonate

Wang, C.; Wu, J.

doi:10.1107/S1600536811052664

Volume 68
Part 1
Page o93
January 2012

Received 24 November 2011
Accepted 7 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R = 0.069
wR = 0.203
Data-to-parameter ratio = 15.9
Details

2,4-Di-tert-butyl-6-[(R/S)-1-(3,5-di-tert-butyl-2-hydroxyphenyl)ethyl]phenyl [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonate

Cheng Wang ^a ^* and Jincai Wu ^b

^aDepartment of Thoracis Surgery, The Second Hospital of Lanzhou University, Lanzhou 730000, People's Republic of China, and ^bDepartment of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
Correspondence e-mail: wujc@lzu.edu.cn

The asymmetric unit of the title compound, C₄₀H₆₀O₅S, comprises two diastereomers related, except for the chiral camphor groups, by a pseudo-inversion centre. In both diasteromers, the camphor sulfate moiety maintained the absolute configuartion (R,S) of the precursor. However, the absolute configurations at the methine C atoms are of opposite chirality. Both molecules reveal intramolecular O-HO hydrogen bonds, whereas van der Waals interactions define the crystal packing.

Related literature

The title compound is a potential ligand for the investigation of ring-opening polymerization of lactides. Poly(lactide) and poly( [epsilon] -caprolactone) and their copolymers are the most promising biodegradable and biocompatible synthetic macromolecules. Due to the advantages of well controlled molecular weight and low polydispersity, many metal complexes have been used, see: Wu et al. (2006).

Experimental

Crystal data

C₄₀H₆₀O₅S
M_r = 652.98
Monoclinic, P 2₁
a = 18.2082 (19) Å
b = 10.6028 (11) Å
c = 20.287 (2) Å
= 93.003 (2)°
V = 3911.2 (7) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 293 K
0.32 × 0.28 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 1, T_max = 1
21496 measured reflections
13182 independent reflections
7458 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.203
S = 1.08
13182 reflections
829 parameters
53 restraints
H-atom parameters constrained
_max = 0.88 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 5058 Friedel pairs
Flack parameter: -0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO3	0.82	2.23	2.974 (6)	152
O1A-H1AAO3A	0.82	2.20	2.957 (6)	153

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); 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 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2372 ).

Acknowledgements

We thank the National Natural Science Foundation of China (No. 21071069) and the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, for financial support.

References

Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.

organic compounds