(3S,7aR)-7-Meth-oxy-7a-methyl-3-phenyl-2,3-dihydro-pyrrolo[2,1-b]oxazol-5(7aH)-one.

In the title chiral butterfly-like bicyclic lactam, C(14)H(15)NO(3), the phenyl and methyl groups are syn with respect to each other. The dihydro-pyrrrole ring adopts a boat conformation, whereas the oxazole ring has a slightly distorted boat conformation. The packing of mol-ecules in the crystal structure is stabilized by inter-molecular 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 = 245.27

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.076

S = 0.89

1170 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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.

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

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

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

C14H15NO3	F(000) = 260
Mr = 245.27	Dx = 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

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

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(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3
1170 reflections	(Δ/σ)max = 0.016
163 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .