(+)-(1S,5R,6R)-6-[(S)-1-Hy-droxy-2-(meth-oxy-meth-yloxy)eth-yl]-1-methyl-3-trichloro-methyl-2-aza-4,7-dioxa-bicyclo-[3.3.0]oct-2-en-8-one.

In the title compound, C(11)H(14)Cl(3)NO(6), the fused five-membered oxazoline and tetra-hydro-furan 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, mol-ecules 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 = 362.58

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.069

S = 1.34

2364 reflections

193 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 947 Friedel pairs

Flack parameter: 0.01 (5)

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042912/is5207sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042912/is5207Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042912/is5207Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H14Cl3NO6	Dx = 1.636 Mg m−3
Mr = 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

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

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(Fo2) + (0.0338P)2] where P = (Fo2 + 2Fc2)/3
S = 1.34	(Δ/σ)max = 0.001
2364 reflections	Δρmax = 0.37 e Å−3
193 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 947 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O9iv	0.98	2.53	3.320 (3)	137

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) ; (ii) ; (iii) .