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

Erdsack, J.; Schürmann, M.; Preut, H.; Krause, N.

doi:10.1107/S1600536808014906

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 (C-C) = 0.007 Å
R = 0.035
wR = 0.087
Data-to-parameter ratio = 14.9
Details

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

Jörg Erdsack,^a Markus Schürmann,^a Hans Preut ^a ^* and Norbert Krause ^a

^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-HO hydrogen bonds.

Related literature

For related literature, see: Anh & Eisenstein (1977); Chérest et al. (1968); Deutsch et al. (2008); Erdsack & Krause (2008); Garner & Park (1987); Hoffmann-Röder & Krause (2001); Kim & Rhee (2000).

Experimental

Crystal data

C₂₂H₃₅NO₅SSi
M_r = 453.66
Monoclinic, C 2
a = 26.283 (5) Å
b = 11.335 (2) Å
c = 19.219 (4) Å
= 121.40 (3)°
V = 4887 (2) Å³
Z = 8
Mo K radiation
= 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(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.087
S = 1.03
8353 reflections
559 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3
Absolute structure: Flack (1983), 3636 Friedel pairs
Flack parameter: -0.09 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4O2ⁱ	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); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

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.
Garner, P. & Park, J. M. (1987). J. Org. Chem. 52, 2361-2364.
Hoffmann-Röder, A. & Krause, N. (2001). Org. Lett. 3, 2537-2538.
Kim, G. & Rhee, H. (2000). J. Kor. Chem. Soc. 44, 30-36.
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.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds