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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 [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.069
Data-to-parameter ratio = 12.2
Details
Open access

(+)-(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

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-H...O and C-H...O hydrogen bonds, forming chains along the b-axis direction. Further C-H...O hydrogen bonds are observed between the chains.

Related literature

For the synthesis, see: Oishi et al. (2012[Oishi, H., Tsuzaki, S., Sato, T. & Chida, N. (2012). In preparation.]). For the isolation of sphingofungins, see: VanMiddlesworth, Giacobbe et al. (1992[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.]); VanMiddlesworth, Dufresne et al. (1992[VanMiddlesworth, F., Dufresne, C., Wincott, F. E., Mosley, R. T. & Wilson, K. E. (1992). Tetrahedron Lett. 33, 297-300.]); Horn et al. (1992[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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14Cl3NO6

  • Mr = 362.58

  • Monoclinic, P 21

  • a = 8.9311 (7) Å

  • b = 6.0283 (4) Å

  • c = 13.8694 (10) Å

  • [beta] = 99.699 (2)°

  • V = 736.05 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.738, Tmax = 0.904

  • 6662 measured reflections

  • 2364 independent reflections

  • 2291 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.069

  • S = 1.34

  • 2364 reflections

  • 193 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 947 Friedel pairs

  • Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O12-H12...O15i 0.84 1.90 2.695 (2) 157
C6-H6...O9ii 1.00 2.43 3.402 (3) 164
C17-H17C...O9iii 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[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: Mercury (Macrae et al., 2006[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.]); 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.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Oishi, H., Tsuzaki, S., Sato, T. & Chida, N. (2012). In preparation.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
VanMiddlesworth, F., Dufresne, C., Wincott, F. E., Mosley, R. T. & Wilson, K. E. (1992). Tetrahedron Lett. 33, 297-300.  [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3185  [ doi:10.1107/S1600536812042912 ]

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