(+)-(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

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3185

doi:10.1107/S1600536812042912

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(+)-(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

(Received 9 October 2012; accepted 15 October 2012; online 20 October 2012)

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 ). 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
β = 99.699 (2)°
V = 736.05 (9) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.069
S = 1.34
2364 reflections
193 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_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—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); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042912/is5207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042912/is5207Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042912/is5207Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812042912/is5207Isup4.cml

checkCIF report

Comment top

Sphingofungins are natural antifungal agents isolated from Aspergillus and reported to be potent inhibitors of the biosynthesis of sphingolipids (VanMiddlesworth, Giacobbe et al., 1992; VanMiddlesworth, Dufresne et al., 1992; Horn et al., 1992). The title compound (I), C₁₁H₁₄Cl₃NO₆, which has four contiguous stereogenic center including a tetra-substituted carbon with nitrogen (Fig. 1), was provided in a synthetic study on the natural products sphingofungins from _D-ribose (Oishi et al., 2012). The absolute configurations were confirmed by the X-ray analysis as C1S, C5R, C6R and C10S. The crystal packing was stabilized by an intermolecular O—H···O hydrogen bond, forming molecular a chain along the b axis (Fig. 2). There are also C—H···O hydrogen bonds and intermolecular Cl···O short contacts, Cl19···O4 (x, y - 1, z) and Cl20···O7 (x + 1, y, z) being 3.070 (2) and 3.142 (2) Å, respectively.

Related literature top

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 top

The title compound was obtained in a synthetic study of sphingofungins from _D-ribose (Oishi et al., 2012), and recrystallized from ethyl acetate solution. [α]²⁷_D +83.1 (c 0.345, CHCl₃); m.p. 409.7–411.2 K.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. The dashed lines indicate O—H···O hydrogen bonds.

(+)-(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 top

Crystal data top

C₁₁H₁₄Cl₃NO₆	D_x = 1.636 Mg m⁻³
M_r = 362.58	Melting point: 409.7 K
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9311 (7) Å	Cell parameters from 5778 reflections
b = 6.0283 (4) Å	θ = 2.3–25.1°
c = 13.8694 (10) Å	µ = 0.65 mm⁻¹
β = 99.699 (2)°	T = 90 K
V = 736.05 (9) Å³	Prism, colourless
Z = 2	0.50 × 0.25 × 0.16 mm
F(000) = 372

Data collection top

Bruker D8 goniometer diffractometer	2364 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.4167 pixels mm^-1	θ_max = 25.1°, θ_min = 2.3°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −7→6
T_min = 0.738, T_max = 0.904	l = −16→16
6662 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0338P)²] where P = (F_o² + 2F_c²)/3
S = 1.34	(Δ/σ)_max = 0.001
2364 reflections	Δρ_max = 0.37 e Å⁻³
193 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 947 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Crystal data top

C₁₁H₁₄Cl₃NO₆	V = 736.05 (9) Å³
M_r = 362.58	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9311 (7) Å	µ = 0.65 mm⁻¹
b = 6.0283 (4) Å	T = 90 K
c = 13.8694 (10) Å	0.50 × 0.25 × 0.16 mm
β = 99.699 (2)°

Data collection top

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

Refinement top

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

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7195 (2)	0.5236 (4)	0.43062 (15)	0.0152 (5)
N2	0.7869 (2)	0.3750 (3)	0.36335 (12)	0.0139 (4)
C3	0.8554 (2)	0.5035 (4)	0.31378 (15)	0.0134 (5)
O4	0.85179 (17)	0.7255 (3)	0.32714 (10)	0.0156 (3)
C5	0.7464 (2)	0.7590 (4)	0.39563 (15)	0.0148 (5)
H5	0.7928	0.8550	0.4516	0.018*
C6	0.5893 (2)	0.8481 (4)	0.34831 (15)	0.0142 (5)
H6	0.5652	0.9825	0.3851	0.017*
O7	0.48036 (16)	0.6720 (3)	0.36046 (10)	0.0162 (4)
C8	0.5464 (2)	0.4965 (4)	0.40903 (15)	0.0142 (5)
O9	0.47385 (18)	0.3412 (3)	0.42994 (10)	0.0181 (4)
C10	0.5688 (3)	0.9041 (4)	0.24039 (15)	0.0161 (5)
H10	0.6464	1.0185	0.2316	0.019*
C11	0.4125 (3)	1.0049 (4)	0.20566 (15)	0.0165 (5)
H11A	0.3335	0.9027	0.2216	0.020*
H11B	0.4039	1.1462	0.2408	0.020*
O12	0.59596 (18)	0.7153 (3)	0.18539 (11)	0.0208 (4)
H12	0.5132	0.6520	0.1642	0.031*
O13	0.38660 (19)	1.0460 (3)	0.10212 (11)	0.0205 (4)
C14	0.4558 (3)	1.2396 (4)	0.07599 (16)	0.0192 (5)
H14A	0.4577	1.2365	0.0049	0.023*
H14B	0.5622	1.2437	0.1105	0.023*
O15	0.38097 (18)	1.4326 (3)	0.09848 (11)	0.0195 (4)
C16	0.2416 (3)	1.4735 (5)	0.03432 (17)	0.0256 (6)
H16A	0.1663	1.3625	0.0456	0.038*
H16B	0.2582	1.4641	−0.0336	0.038*
H16C	0.2045	1.6220	0.0468	0.038*
C17	0.7852 (3)	0.4676 (4)	0.53576 (15)	0.0194 (5)
H17A	0.8962	0.4793	0.5454	0.029*
H17B	0.7564	0.3159	0.5503	0.029*
H17C	0.7455	0.5714	0.5796	0.029*
C18	0.9561 (2)	0.4317 (4)	0.24145 (15)	0.0155 (5)
Cl19	0.95353 (6)	0.14171 (10)	0.22820 (4)	0.02283 (16)
Cl20	1.14459 (6)	0.51691 (10)	0.28730 (4)	0.02415 (16)
Cl21	0.89393 (7)	0.55359 (12)	0.12613 (4)	0.03251 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0208 (12)	0.0143 (12)	0.0113 (10)	0.0026 (11)	0.0052 (9)	−0.0013 (10)
N2	0.0157 (10)	0.0130 (10)	0.0135 (8)	0.0008 (8)	0.0040 (8)	0.0008 (8)
C3	0.0127 (11)	0.0159 (12)	0.0107 (10)	−0.0001 (10)	−0.0005 (8)	−0.0026 (10)
O4	0.0157 (8)	0.0130 (8)	0.0195 (8)	−0.0007 (7)	0.0071 (6)	0.0001 (7)
C5	0.0158 (11)	0.0172 (13)	0.0122 (10)	0.0006 (10)	0.0050 (8)	−0.0015 (11)
C6	0.0191 (12)	0.0100 (11)	0.0147 (10)	−0.0041 (10)	0.0063 (9)	−0.0026 (10)
O7	0.0162 (8)	0.0161 (9)	0.0174 (8)	−0.0006 (7)	0.0061 (6)	0.0032 (7)
C8	0.0219 (12)	0.0125 (12)	0.0094 (10)	0.0023 (11)	0.0065 (9)	−0.0024 (10)
O9	0.0228 (9)	0.0154 (9)	0.0174 (7)	−0.0033 (7)	0.0074 (7)	0.0001 (7)
C10	0.0195 (12)	0.0159 (12)	0.0143 (10)	−0.0009 (10)	0.0064 (9)	−0.0022 (10)
C11	0.0216 (11)	0.0175 (13)	0.0109 (10)	−0.0012 (10)	0.0041 (9)	0.0026 (10)
O12	0.0208 (9)	0.0239 (9)	0.0179 (8)	0.0014 (8)	0.0035 (7)	−0.0072 (8)
O13	0.0294 (9)	0.0177 (9)	0.0135 (8)	−0.0011 (8)	0.0010 (7)	0.0023 (7)
C14	0.0231 (13)	0.0195 (12)	0.0164 (11)	0.0038 (11)	0.0071 (9)	0.0027 (11)
O15	0.0219 (9)	0.0171 (8)	0.0194 (8)	0.0012 (7)	0.0038 (7)	0.0004 (8)
C16	0.0234 (13)	0.0262 (15)	0.0257 (12)	0.0023 (11)	−0.0005 (10)	−0.0014 (12)
C17	0.0190 (12)	0.0231 (14)	0.0168 (11)	0.0052 (10)	0.0048 (9)	0.0037 (11)
C18	0.0158 (12)	0.0159 (12)	0.0151 (11)	−0.0009 (10)	0.0032 (9)	−0.0003 (10)
Cl19	0.0254 (3)	0.0168 (3)	0.0290 (3)	−0.0034 (3)	0.0126 (3)	−0.0074 (3)
Cl20	0.0162 (3)	0.0259 (3)	0.0317 (3)	−0.0044 (3)	0.0079 (2)	−0.0094 (3)
Cl21	0.0345 (4)	0.0461 (5)	0.0202 (3)	0.0192 (3)	0.0139 (3)	0.0130 (3)

Geometric parameters (Å, º) top

C1—N2	1.491 (3)	C11—H11A	0.9900
C1—C17	1.515 (3)	C11—H11B	0.9900
C1—C5	1.532 (3)	O12—H12	0.8400
C1—C8	1.533 (3)	O13—C14	1.396 (3)
N2—C3	1.260 (3)	C14—O15	1.403 (3)
C3—O4	1.352 (3)	C14—H14A	0.9900
C3—C18	1.519 (3)	C14—H14B	0.9900
O4—C5	1.459 (3)	O15—C16	1.424 (3)
C5—C6	1.542 (3)	C16—H16A	0.9800
C5—H5	1.0000	C16—H16B	0.9800
C6—O7	1.468 (3)	C16—H16C	0.9800
C6—C10	1.515 (3)	C17—H17A	0.9800
C6—H6	1.0000	C17—H17B	0.9800
O7—C8	1.337 (3)	C17—H17C	0.9800
C8—O9	1.202 (3)	C18—Cl19	1.757 (3)
C10—O12	1.414 (3)	C18—Cl21	1.763 (2)
C10—C11	1.524 (3)	C18—Cl20	1.773 (2)
C10—H10	1.0000	Cl19—O4ⁱ	3.0697 (17)
C11—O13	1.437 (2)	Cl20—O7ⁱⁱ	3.1419 (16)

N2—C1—C17	109.67 (18)	O13—C11—H11A	109.3
N2—C1—C5	104.89 (16)	C10—C11—H11A	109.3
C17—C1—C5	117.1 (2)	O13—C11—H11B	109.3
N2—C1—C8	108.29 (17)	C10—C11—H11B	109.3
C17—C1—C8	112.22 (18)	H11A—C11—H11B	107.9
C5—C1—C8	104.10 (18)	C10—O12—H12	109.5
C3—N2—C1	104.83 (19)	C14—O13—C11	113.55 (17)
N2—C3—O4	120.6 (2)	O13—C14—O15	112.79 (17)
N2—C3—C18	125.5 (2)	O13—C14—H14A	109.0
O4—C3—C18	113.8 (2)	O15—C14—H14A	109.0
C3—O4—C5	105.01 (17)	O13—C14—H14B	109.0
O4—C5—C1	103.34 (17)	O15—C14—H14B	109.0
O4—C5—C6	114.30 (16)	H14A—C14—H14B	107.8
C1—C5—C6	106.11 (18)	C14—O15—C16	113.79 (18)
O4—C5—H5	110.9	O15—C16—H16A	109.5
C1—C5—H5	110.9	O15—C16—H16B	109.5
C6—C5—H5	110.9	H16A—C16—H16B	109.5
O7—C6—C10	107.59 (17)	O15—C16—H16C	109.5
O7—C6—C5	105.81 (18)	H16A—C16—H16C	109.5
C10—C6—C5	116.62 (18)	H16B—C16—H16C	109.5
O7—C6—H6	108.9	C1—C17—H17A	109.5
C10—C6—H6	108.9	C1—C17—H17B	109.5
C5—C6—H6	108.9	H17A—C17—H17B	109.5
C8—O7—C6	112.65 (16)	C1—C17—H17C	109.5
O9—C8—O7	121.9 (2)	H17A—C17—H17C	109.5
O9—C8—C1	127.1 (2)	H17B—C17—H17C	109.5
O7—C8—C1	111.04 (19)	C3—C18—Cl19	110.75 (17)
O12—C10—C11	112.46 (18)	C3—C18—Cl21	110.46 (16)
O12—C10—C6	110.51 (19)	Cl19—C18—Cl21	108.87 (12)
C11—C10—C6	110.68 (17)	C3—C18—Cl20	108.21 (15)
O12—C10—H10	107.7	Cl19—C18—Cl20	108.69 (13)
C11—C10—H10	107.7	Cl21—C18—Cl20	109.84 (12)
C6—C10—H10	107.7	C18—Cl19—O4ⁱ	139.97 (8)
O13—C11—C10	111.67 (17)	C18—Cl20—O7ⁱⁱ	177.84 (8)

C17—C1—N2—C3	−118.3 (2)	C17—C1—C8—O9	−47.7 (3)
C5—C1—N2—C3	8.3 (2)	C5—C1—C8—O9	−175.3 (2)
C8—C1—N2—C3	119.0 (2)	N2—C1—C8—O7	−105.6 (2)
C1—N2—C3—O4	−1.7 (3)	C17—C1—C8—O7	133.2 (2)
C1—N2—C3—C18	173.61 (19)	C5—C1—C8—O7	5.6 (2)
N2—C3—O4—C5	−6.0 (3)	O7—C6—C10—O12	−59.9 (2)
C18—C3—O4—C5	178.18 (16)	C5—C6—C10—O12	58.7 (3)
C3—O4—C5—C1	10.3 (2)	O7—C6—C10—C11	65.4 (2)
C3—O4—C5—C6	−104.5 (2)	C5—C6—C10—C11	−176.0 (2)
N2—C1—C5—O4	−11.3 (2)	O12—C10—C11—O13	−52.1 (3)
C17—C1—C5—O4	110.49 (19)	C6—C10—C11—O13	−176.20 (19)
C8—C1—C5—O4	−125.02 (17)	C10—C11—O13—C14	−79.6 (2)
N2—C1—C5—C6	109.24 (18)	C11—O13—C14—O15	−74.1 (2)
C17—C1—C5—C6	−128.9 (2)	O13—C14—O15—C16	−74.3 (2)
C8—C1—C5—C6	−4.4 (2)	N2—C3—C18—Cl19	4.6 (3)
O4—C5—C6—O7	115.31 (19)	O4—C3—C18—Cl19	−179.78 (15)
C1—C5—C6—O7	2.1 (2)	N2—C3—C18—Cl21	125.3 (2)
O4—C5—C6—C10	−4.2 (3)	O4—C3—C18—Cl21	−59.1 (2)
C1—C5—C6—C10	−117.4 (2)	N2—C3—C18—Cl20	−114.4 (2)
C10—C6—O7—C8	126.83 (19)	O4—C3—C18—Cl20	61.2 (2)
C5—C6—O7—C8	1.5 (2)	C3—C18—Cl19—O4ⁱ	−12.9 (2)
C6—O7—C8—O9	176.28 (19)	Cl21—C18—Cl19—O4ⁱ	−134.58 (9)
C6—O7—C8—C1	−4.6 (2)	Cl20—C18—Cl19—O4ⁱ	105.81 (13)
N2—C1—C8—O9	73.5 (3)

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

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···O9ⁱⁱⁱ	1.00	2.43	3.402 (3)	164
C17—H17C···O9^iv	0.98	2.53	3.320 (3)	137

Symmetry codes: (i) x, y−1, z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄Cl₃NO₆
M_r	362.58
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	90
a, b, c (Å)	8.9311 (7), 6.0283 (4), 13.8694 (10)
β (°)	99.699 (2)
V (Å³)	736.05 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.50 × 0.25 × 0.16

Data collection
Diffractometer	Bruker D8 goniometer diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2012)
T_min, T_max	0.738, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	6662, 2364, 2291
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.34
No. of reflections	2364
No. of parameters	193
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.22
Absolute structure	Flack (1983), 947 Friedel pairs
Absolute structure parameter	0.01 (5)

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+1.

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. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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 CAS Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oishi, H., Tsuzaki, S., Sato, T. & Chida, N. (2012). In preparation. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
VanMiddlesworth, F., Dufresne, C., Wincott, F. E., Mosley, R. T. & Wilson, K. E. (1992). Tetrahedron Lett. 33, 297–300. CAS Google Scholar
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 CAS Google Scholar

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Volume 68| Part 11| November 2012| Page o3185

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(+)-(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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(+)-(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