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Volume 64 
Part 6 
Page o1171  
June 2008  

Received 22 April 2008
Accepted 16 May 2008
Online 30 May 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.007 Å
R = 0.035
wR = 0.087
Data-to-parameter ratio = 14.9
Details
Open access

(1R,4'S)-4-(tert-Butyldimethylsilanoxy)-1-[2,2-dimethyl-3-(p-tolylsulfonyl)-1,3-oxazolidin-4-yl]but-2-yn-1-ol

aFachbereich Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
Correspondence e-mail: hans.preut@udo.edu

The chiral title compound, C22H35NO5SSi, is a precursor of novel furanomycin derivatives. It crystallizes with two molecules in the asymmetric unit; these show different conformations of the silyl substitutent, as indicated by the Si-O-C-C torsion angles of 41.4 (7) and -84.5 (5)° in the two molecules. The anti configuration of the adjacent stereogenic centers is consistent with the Felkin-Anh model. Each of the two crystallographically independent molecules is connected with a neighbouring molecule of the same type via two symmetry-equivalent O-H...O hydrogen bonds.

Related literature

For related literature, see: Anh & Eisenstein (1977[Anh, N. T. & Eisenstein, O. (1977). Nouv. J. Chim. 1, 61-70.]); Chérest et al. (1968[Chérest, M., Felkin, H. & Prudent, N. (1968). Tetrahedron Lett. 9, 2199-2204.]); Deutsch et al. (2008[Deutsch, C., Lipshutz, B. H. & Krause, N. (2008). J. Am. Chem. Soc. In preparation.]); Erdsack & Krause (2008[Erdsack, J. & Krause, N. (2008). Eur. J. Org. Chem. In preparation.]); Garner & Park (1987[Garner, P. & Park, J. M. (1987). J. Org. Chem. 52, 2361-2364.]); Hoffmann-Röder & Krause (2001[Hoffmann-Röder, A. & Krause, N. (2001). Org. Lett. 3, 2537-2538.]); Kim & Rhee (2000[Kim, G. & Rhee, H. (2000). J. Kor. Chem. Soc. 44, 30-36.]).

[Scheme 1]

Experimental

Crystal data
  • C22H35NO5SSi

  • Mr = 453.66

  • Monoclinic, C 2

  • a = 26.283 (5) Å

  • b = 11.335 (2) Å

  • c = 19.219 (4) Å

  • [beta] = 121.40 (3)°

  • V = 4887 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 173 (1) K

  • 0.10 × 0.08 × 0.01 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 8353 measured reflections

  • 8353 independent reflections

  • 3487 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.087

  • S = 1.03

  • 8353 reflections

  • 559 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3636 Friedel pairs

  • Flack parameter: -0.09 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O2i 0.84 2.01 2.828 (4) 164
O4'-H4'...O2'ii 0.84 2.06 2.851 (4) 157
Symmetry codes: (i) -x, y, -z; (ii) -x+1, y, -z+1.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M. Sweet, pp. 307-326, New York: Academic Press.]); data reduction: DENZO and SCALEPACK; 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-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2724 ).


References

Anh, N. T. & Eisenstein, O. (1977). Nouv. J. Chim. 1, 61-70.
Chérest, M., Felkin, H. & Prudent, N. (1968). Tetrahedron Lett. 9, 2199-2204.
Deutsch, C., Lipshutz, B. H. & Krause, N. (2008). J. Am. Chem. Soc. In preparation.
Erdsack, J. & Krause, N. (2008). Eur. J. Org. Chem. In preparation.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Garner, P. & Park, J. M. (1987). J. Org. Chem. 52, 2361-2364.  [CrossRef] [ChemPort]
Hoffmann-Röder, A. & Krause, N. (2001). Org. Lett. 3, 2537-2538.  [CrossRef] [PubMed] [ChemPort]
Kim, G. & Rhee, H. (2000). J. Kor. Chem. Soc. 44, 30-36.  [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M. Sweet, pp. 307-326, New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2008). E64, o1171  [ doi:10.1107/S1600536808014906 ]

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