(+)-(1S,5R,6R)-6-[(S)-1-Hy­droxy-2-(meth­oxy­meth­yloxy)eth­yl]-1-methyl-3-trichloro­methyl-2-aza-4,7-dioxa­bicyclo­[3.3.0]oct-2-en-8-one

Oishi, T.; Oishi, H.; Tsuzaki, S.; Sato, T.; Chida, N.

doi:10.1107/S1600536812042912

Volume 68
Part 11
Page o3185
November 2012

Received 9 October 2012
Accepted 15 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.069
Data-to-parameter ratio = 12.2
Details

(+)-(1S,5R,6R)-6-[(S)-1-Hydroxy-2-(methoxymethyloxy)ethyl]-1-methyl-3-trichloromethyl-2-aza-4,7-dioxabicyclo[3.3.0]oct-2-en-8-one

Takeshi Oishi,^a ^* Hiroki Oishi,^b Syun Tsuzaki,^b Takaaki Sato ^b and Noritaka Chida ^b

^aSchool of Medicine, Keio University, Hiyoshi 4-1-1, Kohoku-ku, Yokohama 223-8521, Japan, and ^bDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan
Correspondence e-mail: oec@a6.keio.jp

In the title compound, C₁₁H₁₄Cl₃NO₆, the fused five-membered oxazoline and tetrahydrofuran rings are essentially planar with maximum deviations of 0.069 (1) and 0.031 (1) Å, respectively, and make a dihedral angle of 64.23 (11)° with each other. In the crystal, molecules are linked by O-HO and C-HO hydrogen bonds, forming chains along the b-axis direction. Further C-HO hydrogen bonds are observed between the chains.

Related literature

For the synthesis, see: Oishi et al. (2012). For the isolation of sphingofungins, see: VanMiddlesworth, Giacobbe et al. (1992); VanMiddlesworth, Dufresne et al. (1992); Horn et al. (1992).

Experimental

Crystal data

C₁₁H₁₄Cl₃NO₆
M_r = 362.58
Monoclinic, P 2₁
a = 8.9311 (7) Å
b = 6.0283 (4) Å
c = 13.8694 (10) Å
= 99.699 (2)°
V = 736.05 (9) Å³
Z = 2
Mo K radiation
= 0.65 mm^-1
T = 90 K
0.50 × 0.25 × 0.16 mm

Data collection

Bruker D8 goniometer diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012) T_min = 0.738, T_max = 0.904
6662 measured reflections
2364 independent reflections
2291 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.069
S = 1.34
2364 reflections
193 parameters
1 restraint
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 947 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O12-H12O15ⁱ	0.84	1.90	2.695 (2)	157
C6-H6O9ⁱⁱ	1.00	2.43	3.402 (3)	164
C17-H17CO9ⁱⁱⁱ	0.98	2.53	3.320 (3)	137
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5207 ).

Acknowledgements

We thank Professor S. Ohba, Professor N. Yoshioka and Dr C. Maeda (Keio University, Japan) for providing valuable advice.

References

Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Horn, W. S., Smith, J. L., Bills, G. F., Raghoobar, S. L., Helms, G. L., Kurts, M. B., Marrinan, J. A., Frommer, B. R., Thornton, R. A. & Mandala, S. M. (1992). J. Antibiot. 45, 1692-1696.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oishi, H., Tsuzaki, S., Sato, T. & Chida, N. (2012). In preparation.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
VanMiddlesworth, F., Dufresne, C., Wincott, F. E., Mosley, R. T. & Wilson, K. E. (1992). Tetrahedron Lett. 33, 297-300.
VanMiddlesworth, F., Giacobbe, R. A., Lopez, M., Garrity, G., Bland, J. A., Bartizal, K., Fromtling, R. A., Polishook, J., Zweerink, M., Edison, A. M., Rozdilsky, W., Wilson, K. E. & Monaghan, R. L. (1992). J. Antibiot. 45, 861-867.

organic compounds