(3S,7aR)-7-Meth­oxy-7a-methyl-3-phenyl-2,3-dihydro­pyrrolo[2,1-b]oxazol-5(7aH)-one

Zheng, J.-F.; Jiang, L.-J.; Ye*, J.-L.

doi:10.1107/S1600536808040105

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o27

doi:10.1107/S1600536808040105

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(3S,7aR)-7-Methoxy-7a-methyl-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one

Jian-Feng Zheng,^a Li-Jiao Jiang ^a and Jian-Liang Ye ^a ^*

^aThe Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China
^*Correspondence e-mail: yejl@xmu.edu.cn

(Received 6 November 2008; accepted 28 November 2008; online 6 December 2008)

In the title chiral butterfly-like bicyclic lactam, C₁₄H₁₅NO₃, the phenyl and methyl groups are syn with respect to each other. The dihydropyrrrole ring adopts a boat conformation, whereas the oxazole ring has a slightly distorted boat conformation. The packing of molecules in the crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For reference bond-length data, see: Allen et al. (1987 ). For the chemistry of tetramic acids and methyl tetramates, see: Huang & Deng (2004 ); Huang et al. (2003 ); Jiang et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₅NO₃
M_r = 245.27
Monoclinic, P 2₁
a = 7.8238 (10) Å
b = 5.9033 (7) Å
c = 13.711 (3) Å
β = 96.597 (14)°
V = 629.05 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.40 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.964, T_max = 0.984
3205 measured reflections
1170 independent reflections
691 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.076
S = 0.89
1170 reflections
163 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2ⁱ	0.96	2.54	3.301 (4)	136
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040105/wn2289sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040105/wn2289Isup2.hkl

checkCIF report

Comment top

The title compound, which was obtained by treating 5-hydroxy-1-((S)-2-hydroxy-1-phenylethyl) -4-methoxy-5-methyl-1H-pyrrol-2(5H)-one and picolinic acid with a catalytic amount of p-TsOH in CH₂Cl₂ at room temperature, is a key intermediate for the preparation of tetramic acids and methyl tetramates bearing C-5 methyl substituents; this is a key framework in a number of bioactive natural products, such as melophlins and mirabimide E (Huang & Deng, 2004; Huang et al., 2003; Jiang et al., 2009).

An X-ray crystal structure determination of the molecular structure of the title compound was carried out to determine its conformation. In the title chiral butterfly-like bicyclic lactam, C₁₄H₁₅NO₃, in which the angle O3—C14—C6 is 112.3 (4)° and C8—N1—C9 is 119.6 (3)°, the phenyl and methyl groups are syn with respect to each other. The dihydropyrrrole ring adopts a boat conformation, whereas in the oxazole ring the conformation is that of a slightly distorted boat. Bond lengths and angles are in agreement with values reported in the literature (Allen et al., 1987). The packing of molecules in the crystal structure is stabilized by intermolecular C—H···O hydrogen bonds.

Related literature top

For reference bond-length data, see: Allen et al. (1987). For the chemistry of tetramic acids and methyl tetramates, see: Huang & Deng (2004); Huang et al. (2003); Jiang et al. (2009). [Should the chemical name be (3R,7aS)- rather than (3S,7aR)-;suggested by PLATON check report and a Chester check?]

Experimental top

To a cool (-78 °C) solution of (S)-1-(2-hydroxyl-1-phenylethyl) -3-methoxy-1H-pyrrole-2,5-dione (1.0 mmol) in anhydrous THF (10 ml) was added dropwise CH₃MgBr (3.0 mmol) in diethyl ether under a nitrogen atmosphere. After stirring at the same temperature for 45 minutes, the reaction was quenched with saturated ammonium chloride (6 ml), and extracted with EtOAc (4 × 10 ml). The combined extracts were washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was purified by flash chromatography and yielded a mixture of diastereomers. To the mixture of diastereomers (0.51 mmol) in CH₂Cl₂ (10 ml) was added p-toluenesulfonic acid monohydrate (0.16 mmol.). After stirring for 30 minutes at room temperature, the mixture was quenched with saturated NaHCO₃ solution. The organic layer was separated and the aqueous phase was extracted with CH₂Cl₂ (3 × 5 ml). The combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was purified by flash chromatography to yield the title compound. Single crystals were obtained by slow evaporation of a petroleum ether / ethyl acetate solution.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labelling scheme, showing 50% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The packing of the molecules, viewed down the b axis. C—H···O hydrogen bond interactions are shown as dashed lines.

(3S,7aR)-7-Methoxy-7a-methyl-3-phenyl-2,3- dihydropyrrolo[2,1-b]oxazol-5(7aH)-one top

Crystal data top

C₁₄H₁₅NO₃	F(000) = 260
M_r = 245.27	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 672 reflections
a = 7.8238 (10) Å	θ = 2.9–32.6°
b = 5.9033 (7) Å	µ = 0.09 mm⁻¹
c = 13.711 (3) Å	T = 293 K
β = 96.597 (14)°	Needle, colourless
V = 629.05 (16) Å³	0.40 × 0.18 × 0.12 mm
Z = 2

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	1170 independent reflections
Radiation source: fine-focus sealed tube	691 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −9→9
T_min = 0.964, T_max = 0.984	k = −4→7
3205 measured reflections	l = −16→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0229P)²] where P = (F_o² + 2F_c²)/3
1170 reflections	(Δ/σ)_max = 0.016
163 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₄H₁₅NO₃	V = 629.05 (16) Å³
M_r = 245.27	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.8238 (10) Å	µ = 0.09 mm⁻¹
b = 5.9033 (7) Å	T = 293 K
c = 13.711 (3) Å	0.40 × 0.18 × 0.12 mm
β = 96.597 (14)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	1170 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	691 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.984	R_int = 0.067
3205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.076	H-atom parameters constrained
S = 0.89	Δρ_max = 0.16 e Å⁻³
1170 reflections	Δρ_min = −0.15 e Å⁻³
163 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.1601 (4)	0.4015 (5)	0.7374 (3)	0.0243 (9)
O2	−0.1216 (3)	0.4978 (5)	0.6847 (3)	0.0474 (10)
C3	0.1854 (5)	0.2927 (6)	0.9142 (4)	0.0283 (12)
O1	0.3713 (4)	0.3770 (5)	0.5217 (3)	0.0460 (9)
C5	0.2722 (5)	0.4920 (7)	0.9416 (4)	0.0340 (12)
H5A	0.2952	0.5946	0.8934	0.041*
C6	0.2535 (5)	0.4025 (7)	0.5833 (4)	0.0323 (11)
C7	0.1517 (5)	0.1443 (7)	0.9894 (4)	0.0340 (13)
H7A	0.0933	0.0095	0.9740	0.041*
C8	0.1279 (5)	0.2310 (7)	0.8097 (4)	0.0309 (12)
H8A	0.0044	0.1977	0.8030	0.037*
C9	0.0262 (5)	0.4666 (6)	0.6652 (4)	0.0310 (11)
C10	0.2041 (5)	0.1961 (8)	1.0856 (5)	0.0416 (13)
H10A	0.1807	0.0959	1.1347	0.050*
C11	0.3251 (6)	0.5415 (8)	1.0386 (4)	0.0437 (14)
H11A	0.3842	0.6753	1.0551	0.052*
O3	0.3124 (4)	0.0915 (5)	0.6977 (3)	0.0601 (12)
C13	0.2908 (5)	0.3940 (8)	1.1107 (4)	0.0418 (13)
H13A	0.3259	0.4272	1.1762	0.050*
C14	0.3068 (5)	0.3310 (7)	0.6872 (4)	0.0339 (12)
C15	0.4755 (5)	0.4379 (9)	0.7300 (4)	0.0503 (14)
H15A	0.5033	0.3885	0.7966	0.075*
H15B	0.4645	0.5998	0.7284	0.075*
H15C	0.5654	0.3929	0.6919	0.075*
C16	0.0944 (5)	0.4851 (7)	0.5732 (4)	0.0386 (13)
H16A	0.0370	0.5450	0.5158	0.046*
C17	0.3234 (7)	0.4610 (10)	0.4231 (4)	0.0636 (16)
H17A	0.4160	0.4352	0.3842	0.095*
H17B	0.3001	0.6204	0.4255	0.095*
H17C	0.2223	0.3830	0.3942	0.095*
C19	0.2233 (7)	0.0254 (7)	0.7733 (5)	0.0562 (17)
H19A	0.3023	−0.0355	0.8266	0.067*
H19B	0.1414	−0.0921	0.7509	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0233 (17)	0.0272 (18)	0.022 (3)	0.0013 (15)	0.0014 (17)	0.0048 (18)
O2	0.0300 (16)	0.069 (2)	0.043 (3)	0.0111 (17)	0.0055 (16)	0.0099 (19)
C3	0.026 (2)	0.026 (3)	0.034 (4)	0.0031 (18)	0.005 (2)	0.002 (2)
O1	0.0494 (19)	0.0528 (19)	0.039 (3)	−0.0044 (17)	0.0195 (19)	−0.003 (2)
C5	0.042 (2)	0.023 (2)	0.037 (4)	−0.001 (2)	0.002 (2)	−0.003 (3)
C6	0.036 (3)	0.029 (2)	0.033 (3)	−0.012 (2)	0.007 (2)	−0.005 (2)
C7	0.027 (2)	0.029 (3)	0.046 (4)	−0.0049 (18)	0.004 (3)	−0.001 (3)
C8	0.034 (2)	0.025 (2)	0.033 (4)	−0.011 (2)	0.001 (2)	−0.003 (2)
C9	0.029 (2)	0.030 (2)	0.034 (3)	−0.002 (2)	0.004 (2)	0.000 (2)
C10	0.035 (3)	0.052 (3)	0.036 (4)	0.003 (3)	−0.001 (3)	0.012 (3)
C11	0.054 (3)	0.036 (3)	0.039 (4)	−0.005 (2)	−0.008 (3)	−0.004 (3)
O3	0.068 (2)	0.035 (2)	0.086 (4)	0.0224 (16)	0.047 (2)	0.020 (2)
C13	0.041 (3)	0.058 (3)	0.023 (3)	0.013 (3)	−0.009 (2)	0.004 (3)
C14	0.029 (2)	0.030 (3)	0.044 (4)	0.010 (2)	0.011 (2)	0.006 (2)
C15	0.030 (2)	0.078 (4)	0.043 (4)	−0.004 (3)	0.003 (2)	0.004 (3)
C16	0.030 (2)	0.042 (3)	0.041 (4)	−0.001 (2)	−0.005 (2)	0.007 (3)
C17	0.079 (4)	0.074 (4)	0.040 (4)	−0.025 (3)	0.018 (3)	−0.004 (4)
C19	0.082 (4)	0.032 (3)	0.059 (5)	−0.006 (3)	0.024 (4)	−0.003 (3)

Geometric parameters (Å, º) top

N1—C9	1.410 (5)	C10—C13	1.374 (7)
N1—C8	1.455 (5)	C10—H10A	0.9300
N1—C14	1.465 (5)	C11—C13	1.366 (7)
O2—C9	1.230 (4)	C11—H11A	0.9300
C3—C5	1.389 (5)	O3—C19	1.371 (6)
C3—C7	1.402 (6)	O3—C14	1.421 (5)
C3—C8	1.497 (7)	C13—H13A	0.9300
O1—C6	1.329 (5)	C14—C15	1.519 (6)
O1—C17	1.448 (7)	C15—H15A	0.9600
C5—C11	1.378 (7)	C15—H15B	0.9600
C5—H5A	0.9300	C15—H15C	0.9600
C6—C16	1.329 (5)	C16—H16A	0.9300
C6—C14	1.498 (7)	C17—H17A	0.9600
C7—C10	1.369 (7)	C17—H17B	0.9600
C7—H7A	0.9300	C17—H17C	0.9600
C8—C19	1.538 (6)	C19—H19A	0.9700
C8—H8A	0.9800	C19—H19B	0.9700
C9—C16	1.429 (6)

C9—N1—C8	119.6 (3)	C19—O3—C14	110.3 (4)
C9—N1—C14	107.9 (4)	C11—C13—C10	119.5 (5)
C8—N1—C14	109.3 (3)	C11—C13—H13A	120.2
C5—C3—C7	117.2 (5)	C10—C13—H13A	120.2
C5—C3—C8	123.4 (4)	O3—C14—N1	104.6 (3)
C7—C3—C8	119.5 (4)	O3—C14—C6	112.3 (4)
C6—O1—C17	115.5 (4)	N1—C14—C6	102.6 (3)
C11—C5—C3	121.7 (5)	O3—C14—C15	111.0 (4)
C11—C5—H5A	119.2	N1—C14—C15	113.2 (4)
C3—C5—H5A	119.2	C6—C14—C15	112.6 (4)
O1—C6—C16	133.2 (5)	C14—C15—H15A	109.5
O1—C6—C14	115.8 (4)	C14—C15—H15B	109.5
C16—C6—C14	111.0 (4)	H15A—C15—H15B	109.5
C10—C7—C3	120.6 (4)	C14—C15—H15C	109.5
C10—C7—H7A	119.7	H15A—C15—H15C	109.5
C3—C7—H7A	119.7	H15B—C15—H15C	109.5
N1—C8—C3	115.3 (3)	C6—C16—C9	108.7 (5)
N1—C8—C19	101.3 (4)	C6—C16—H16A	125.7
C3—C8—C19	113.5 (4)	C9—C16—H16A	125.7
N1—C8—H8A	108.8	O1—C17—H17A	109.5
C3—C8—H8A	108.8	O1—C17—H17B	109.5
C19—C8—H8A	108.8	H17A—C17—H17B	109.5
O2—C9—N1	122.0 (4)	O1—C17—H17C	109.5
O2—C9—C16	129.5 (5)	H17A—C17—H17C	109.5
N1—C9—C16	108.5 (3)	H17B—C17—H17C	109.5
C7—C10—C13	121.0 (5)	O3—C19—C8	109.2 (4)
C7—C10—H10A	119.5	O3—C19—H19A	109.8
C13—C10—H10A	119.5	C8—C19—H19A	109.8
C13—C11—C5	120.0 (5)	O3—C19—H19B	109.8
C13—C11—H11A	120.0	C8—C19—H19B	109.8
C5—C11—H11A	120.0	H19A—C19—H19B	108.3

C7—C3—C5—C11	0.7 (5)	C19—O3—C14—N1	−19.4 (6)
C8—C3—C5—C11	−179.1 (4)	C19—O3—C14—C6	−129.9 (5)
C17—O1—C6—C16	2.4 (7)	C19—O3—C14—C15	103.0 (5)
C17—O1—C6—C14	−175.9 (4)	C9—N1—C14—O3	−107.5 (4)
C5—C3—C7—C10	−0.3 (6)	C8—N1—C14—O3	24.0 (5)
C8—C3—C7—C10	179.5 (4)	C9—N1—C14—C6	9.9 (4)
C9—N1—C8—C3	−130.6 (4)	C8—N1—C14—C6	141.4 (3)
C14—N1—C8—C3	104.4 (4)	C9—N1—C14—C15	131.5 (4)
C9—N1—C8—C19	106.3 (4)	C8—N1—C14—C15	−97.0 (4)
C14—N1—C8—C19	−18.6 (5)	O1—C6—C14—O3	−74.1 (5)
C5—C3—C8—N1	−3.5 (6)	C16—C6—C14—O3	107.3 (4)
C7—C3—C8—N1	176.7 (3)	O1—C6—C14—N1	174.2 (3)
C5—C3—C8—C19	112.8 (4)	C16—C6—C14—N1	−4.4 (5)
C7—C3—C8—C19	−67.0 (5)	O1—C6—C14—C15	52.1 (5)
C8—N1—C9—O2	42.2 (6)	C16—C6—C14—C15	−126.5 (4)
C14—N1—C9—O2	167.8 (4)	O1—C6—C16—C9	179.0 (4)
C8—N1—C9—C16	−137.6 (4)	C14—C6—C16—C9	−2.7 (5)
C14—N1—C9—C16	−12.0 (4)	O2—C9—C16—C6	−170.5 (4)
C3—C7—C10—C13	−0.1 (6)	N1—C9—C16—C6	9.2 (5)
C3—C5—C11—C13	−0.7 (6)	C14—O3—C19—C8	8.1 (6)
C5—C11—C13—C10	0.3 (6)	N1—C8—C19—O3	6.7 (5)
C7—C10—C13—C11	0.1 (6)	C3—C8—C19—O3	−117.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2ⁱ	0.96	2.54	3.301 (4)	136

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₃
M_r	245.27
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.8238 (10), 5.9033 (7), 13.711 (3)
β (°)	96.597 (14)
V (Å³)	629.05 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.964, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3205, 1170, 691
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.076, 0.89
No. of reflections	1170
No. of parameters	163
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2ⁱ	0.96	2.54	3.301 (4)	136.4

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank the Natural Science Foundation of China (No. 20602028) and Xiamen University Science Foundation (No. XDKJCX20053013) for financial support. We also thank Mr Zan-Bin Wei and Mr Ting-Bin Wen for technical assistance.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Huang, P.-Q. & Deng, J. (2004). Synlett, pp. 247–250. Web of Science CrossRef Google Scholar
Huang, P.-Q., Wu, T.-J. & Ruan, Y.-P. (2003). Org. Lett. 5, 4341–4344. Web of Science CrossRef PubMed CAS Google Scholar
Jiang, L.-J., Lan, H.-Q., Zheng, J.-F., Ye, J.-L. & Huang, P.-Q. (2009). Synlett. In the press. Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Page o27

doi:10.1107/S1600536808040105

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

(3S,7aR)-7-Meth­­oxy-7a-methyl-3-phenyl-2,3-di­hydro­pyrrolo[2,1-b]oxazol-5(7aH)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3S,7aR)-7-Methoxy-7a-methyl-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one