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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 [sigma](C-C) = 0.009 Å
R = 0.069
wR = 0.203
Data-to-parameter ratio = 15.9
Details
Open access

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

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-H...O 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[Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.]).

[Scheme 1]

Experimental

Crystal data
  • C40H60O5S

  • Mr = 652.98

  • Monoclinic, P 21

  • a = 18.2082 (19) Å

  • b = 10.6028 (11) Å

  • c = 20.287 (2) Å

  • [beta] = 93.003 (2)°

  • V = 3911.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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)[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 1, Tmax = 1

  • 21496 measured reflections

  • 13182 independent reflections

  • 7458 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.203

  • S = 1.08

  • 13182 reflections

  • 829 parameters

  • 53 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.88 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5058 Friedel pairs

  • Flack parameter: -0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O3 0.82 2.23 2.974 (6) 152
O1A-H1AA...O3A 0.82 2.20 2.957 (6) 153

Data collection: SMART (Bruker, 1998[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o93  [ doi:10.1107/S1600536811052664 ]

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