(3-Methyl-3a,4,7,7a-tetra­hydro-5H-4,7-methano­isoxazolo[4,5-d][1,2]oxazin-5-yl)(phen­yl)methanone

Lough, A.J.; Nagireddy, J.R.; Tam, W.

doi:10.1107/S1600536814007740

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o543

doi:10.1107/S1600536814007740

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(3-Methyl-3a,4,7,7a-tetrahydro-5H-4,7-methanoisoxazolo[4,5-d][1,2]oxazin-5-yl)(phenyl)methanone

Alan J. Lough,^a ^* Jaipal R. Nagireddy ^b and William Tam ^b

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and ^bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 19 March 2014; accepted 7 April 2014; online 12 April 2014)

The title compound, C₁₄H₁₄N₂O₃, is the exo isomer with a syn arrangement of two O atoms in the isoxazole and oxazine rings. The dihedral angle between the isoxazole and phenyl rings is 60.38 (4)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules, forming a three-dimensional network. The isoxazole O atom is an acceptor for three of these hydrogen bonds.

CCDC reference: 995952

Related literature

For 1,3-dipolar cycloaddition reactions of symmetrical and unsymmetrical bicyclic alkenes, see: Yip et al. (2001 ); Mayo et al. (2001 ). For a related structure, see: Lough et al. (2014 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₃
M_r = 258.27
Orthorhombic, P b c a
a = 9.5030 (18) Å
b = 10.2912 (16) Å
c = 25.347 (5) Å
V = 2478.9 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 147 K
0.38 × 0.16 × 0.10 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.671, T_max = 0.746
12134 measured reflections
2854 independent reflections
2145 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.101
S = 1.03
2854 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O3ⁱ	1.00	2.50	3.2793 (18)	135
C5—H5A⋯O2ⁱⁱ	1.00	2.59	3.4017 (18)	138
C7—H7B⋯O2ⁱⁱ	0.98	2.56	3.3900 (19)	142
C7—H7C⋯O2ⁱⁱⁱ	0.98	2.60	3.568 (2)	170
C11—H11A⋯O3^iv	0.95	2.58	3.470 (2)	156
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 995952

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007740/is5350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007740/is5350Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007740/is5350Isup3.cml

checkCIF report

Comment top

We have previously investigated the 1,3-dipolar cycloaddition reactions of symmetrical and unsymmetrical bicyclic alkenes (Yip et al., 2001; Mayo et al., 2001). When expanding this study on N-acyl-2-oxa-3-azanorborn-5-enes, the bicyclic alkene (III) reacts (see Fig. 1) with acetonitrile oxide (II) (generated in situ) in toluene, to give the cycloadducts (IV) and (V) as regioisomers in the ratio of 70:30 respectively (ratio was determined by isolated yields). The stereochemistry and regiochemistry of the major product (IV) was determined by this single-crystal X-ray analysis. Although different stereoisomers (exo and endo) could be formed, only the exo stereoisomer was formed with a mixture of the corresponding regioisomers. The major product obtained was found to be the syn isomer (two O atoms in the rings are on the same side of the molecule).

The molecular structure of the title compound is shown in Fig. 2. The dihedral angle between the isoxazole ring [C4/C5/C6/O2/N2 with r.m.s. deviation 0.0013 Å] and the phenyl ring (C9–C14) is 60.38 (4)°. In the crystal, weak C—H···O hydrogen bonds link molecules forming a three-dimensional network (Fig. 3). The isoxazole O atom is an acceptor for three of these hydrogen bonds. We have prepared by a similar method and carried out the structure determination of a related cycloadduct (Lough et al., 2014)

Related literature top

For 1,3-dipolar cycloaddition reactions of symmetrical and unsymmetrical bicyclic alkenes, see: Yip et al. (2001); Mayo et al. (2001). For a related structure, see: Lough et al. (2014).

Experimental top

A solution of nitroethane (I) (126 mg, 0.579 mmol) in toluene (2 ml) was added to a flame-dried flask containing bicyclic alkene (III) (140 mg, 0.642 mmol), (BOC)₂O (233.7 mg, 1.07 mmol), DMAP (9.4 mg, 0.077 mmol) and toluene (2 ml) via a cannula over 10 minutes. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed by rotary evaporation, and the crude product was purified by column chromatography (EtOAc:hexanes = 1:9 to 9:1) to obtain regiosomers (IV) and (V) in 61% and 26% respectively. A solution of isomer (IV) in EtOAc:hexanes = 1:3 gave single crystals suitable for X-ray analysis.

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: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of the title compound showing 30% probability ellipsoids.
	Fig. 3. Part of the crystal structure with weak hydrogen bonds shown as dashed lines.

(3-Methyl-3a,4,7,7a-tetrahydro-5H-4,7-methanoisoxazolo[4,5-d][1,2]oxazin-5-yl)(phenyl)methanone top

Crystal data top

C₁₄H₁₄N₂O₃	D_x = 1.384 Mg m⁻³
M_r = 258.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2381 reflections
a = 9.5030 (18) Å	θ = 2.7–26.8°
b = 10.2912 (16) Å	µ = 0.10 mm⁻¹
c = 25.347 (5) Å	T = 147 K
V = 2478.9 (8) Å³	Needle, colourless
Z = 8	0.38 × 0.16 × 0.10 mm
F(000) = 1088

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2145 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −12→9
T_min = 0.671, T_max = 0.746	k = −11→13
12134 measured reflections	l = −24→32
2854 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0436P)² + 0.7731P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2854 reflections	Δρ_max = 0.28 e Å⁻³
173 parameters	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₃	V = 2478.9 (8) Å³
M_r = 258.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.5030 (18) Å	µ = 0.10 mm⁻¹
b = 10.2912 (16) Å	T = 147 K
c = 25.347 (5) Å	0.38 × 0.16 × 0.10 mm

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2854 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	2145 reflections with I > 2σ(I)
T_min = 0.671, T_max = 0.746	R_int = 0.044
12134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
2854 reflections	Δρ_min = −0.20 e Å⁻³
173 parameters

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.

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

	x	y	z	U_iso*/U_eq
O1	0.42779 (11)	0.16029 (10)	0.34310 (4)	0.0239 (3)
O2	0.28195 (12)	0.06699 (10)	0.47211 (4)	0.0274 (3)
O3	0.44907 (11)	0.49825 (10)	0.35864 (4)	0.0261 (3)
N1	0.48705 (13)	0.28419 (11)	0.35988 (5)	0.0206 (3)
N2	0.32314 (13)	0.14237 (12)	0.51709 (5)	0.0240 (3)
C1	0.51026 (15)	0.27468 (14)	0.41673 (6)	0.0196 (3)
H1A	0.5784	0.3390	0.4316	0.023*
C2	0.55574 (16)	0.13321 (14)	0.42059 (6)	0.0247 (3)
H2A	0.6441	0.1146	0.4013	0.030*
H2B	0.5618	0.1013	0.4574	0.030*
C3	0.42502 (16)	0.08599 (14)	0.39177 (6)	0.0229 (3)
H3A	0.4207	−0.0103	0.3867	0.027*
C4	0.30441 (16)	0.14184 (14)	0.42428 (6)	0.0218 (3)
H4A	0.2162	0.1520	0.4031	0.026*
C5	0.36368 (14)	0.27359 (13)	0.44313 (6)	0.0183 (3)
H5A	0.3038	0.3490	0.4324	0.022*
C6	0.36722 (14)	0.25337 (14)	0.50174 (6)	0.0193 (3)
C7	0.41835 (16)	0.35181 (15)	0.54006 (6)	0.0242 (3)
H7A	0.4135	0.3160	0.5758	0.036*
H7B	0.3593	0.4297	0.5379	0.036*
H7C	0.5160	0.3747	0.5318	0.036*
C8	0.44268 (15)	0.39406 (14)	0.33502 (6)	0.0198 (3)
C9	0.40242 (15)	0.38382 (14)	0.27853 (6)	0.0201 (3)
C10	0.46180 (16)	0.29115 (14)	0.24524 (6)	0.0243 (3)
H10A	0.5260	0.2289	0.2589	0.029*
C11	0.42718 (18)	0.28984 (15)	0.19209 (6)	0.0271 (4)
H11A	0.4685	0.2274	0.1693	0.033*
C12	0.33260 (17)	0.37935 (15)	0.17233 (6)	0.0283 (4)
H12A	0.3077	0.3772	0.1361	0.034*
C13	0.27394 (16)	0.47228 (16)	0.20515 (7)	0.0281 (4)
H13A	0.2094	0.5340	0.1913	0.034*
C14	0.30932 (15)	0.47535 (14)	0.25820 (6)	0.0241 (3)
H14A	0.2701	0.5398	0.2806	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0346 (6)	0.0167 (5)	0.0205 (6)	−0.0054 (4)	−0.0012 (5)	−0.0033 (4)
O2	0.0370 (6)	0.0217 (5)	0.0236 (6)	−0.0101 (5)	0.0037 (5)	−0.0003 (4)
O3	0.0372 (6)	0.0194 (6)	0.0218 (6)	−0.0014 (5)	0.0026 (5)	−0.0042 (4)
N1	0.0278 (6)	0.0165 (6)	0.0177 (6)	−0.0063 (5)	−0.0007 (5)	−0.0024 (5)
N2	0.0275 (6)	0.0226 (7)	0.0220 (7)	−0.0017 (5)	0.0025 (5)	0.0002 (5)
C1	0.0212 (7)	0.0208 (7)	0.0167 (7)	−0.0028 (6)	−0.0001 (6)	−0.0003 (6)
C2	0.0244 (7)	0.0249 (8)	0.0248 (8)	0.0046 (6)	0.0015 (6)	0.0010 (6)
C3	0.0315 (8)	0.0157 (7)	0.0213 (8)	0.0002 (6)	0.0004 (6)	0.0008 (6)
C4	0.0234 (7)	0.0195 (8)	0.0224 (8)	−0.0036 (6)	−0.0005 (6)	0.0005 (6)
C5	0.0199 (7)	0.0167 (7)	0.0182 (7)	0.0003 (5)	−0.0011 (6)	0.0002 (6)
C6	0.0188 (6)	0.0202 (7)	0.0187 (8)	0.0025 (5)	0.0015 (6)	0.0013 (5)
C7	0.0292 (8)	0.0254 (8)	0.0179 (8)	−0.0026 (6)	−0.0018 (6)	0.0007 (6)
C8	0.0208 (7)	0.0195 (8)	0.0193 (8)	−0.0013 (6)	0.0044 (6)	−0.0019 (6)
C9	0.0233 (7)	0.0189 (7)	0.0181 (8)	−0.0033 (6)	0.0021 (6)	−0.0003 (6)
C10	0.0315 (8)	0.0219 (8)	0.0194 (8)	0.0016 (6)	0.0027 (6)	−0.0006 (6)
C11	0.0385 (9)	0.0226 (8)	0.0203 (8)	−0.0030 (7)	0.0042 (7)	−0.0029 (6)
C12	0.0353 (8)	0.0288 (9)	0.0206 (8)	−0.0115 (7)	−0.0043 (7)	0.0034 (6)
C13	0.0266 (8)	0.0279 (9)	0.0299 (9)	−0.0018 (6)	−0.0051 (7)	0.0072 (7)
C14	0.0245 (7)	0.0212 (8)	0.0265 (9)	−0.0003 (6)	0.0028 (6)	0.0006 (6)

Geometric parameters (Å, º) top

O1—C3	1.4515 (18)	C5—C6	1.501 (2)
O1—N1	1.4572 (15)	C5—H5A	1.0000
O2—N2	1.4333 (16)	C6—C7	1.485 (2)
O2—C4	1.4524 (18)	C7—H7A	0.9800
O3—C8	1.2296 (17)	C7—H7B	0.9800
N1—C8	1.3613 (19)	C7—H7C	0.9800
N1—C1	1.4611 (18)	C8—C9	1.486 (2)
N2—C6	1.2773 (19)	C9—C14	1.391 (2)
C1—C2	1.522 (2)	C9—C10	1.393 (2)
C1—C5	1.545 (2)	C10—C11	1.387 (2)
C1—H1A	1.0000	C10—H10A	0.9500
C2—C3	1.521 (2)	C11—C12	1.381 (2)
C2—H2A	0.9900	C11—H11A	0.9500
C2—H2B	0.9900	C12—C13	1.385 (2)
C3—C4	1.524 (2)	C12—H12A	0.9500
C3—H3A	1.0000	C13—C14	1.386 (2)
C4—C5	1.544 (2)	C13—H13A	0.9500
C4—H4A	1.0000	C14—H14A	0.9500

C3—O1—N1	102.71 (10)	C6—C5—H5A	112.9
N2—O2—C4	109.68 (10)	C4—C5—H5A	112.9
C8—N1—O1	118.17 (11)	C1—C5—H5A	112.9
C8—N1—C1	123.97 (12)	N2—C6—C7	121.22 (14)
O1—N1—C1	106.71 (10)	N2—C6—C5	114.71 (13)
C6—N2—O2	109.36 (12)	C7—C6—C5	124.07 (13)
N1—C1—C2	99.81 (12)	C6—C7—H7A	109.5
N1—C1—C5	106.95 (11)	C6—C7—H7B	109.5
C2—C1—C5	102.78 (11)	H7A—C7—H7B	109.5
N1—C1—H1A	115.2	C6—C7—H7C	109.5
C2—C1—H1A	115.2	H7A—C7—H7C	109.5
C5—C1—H1A	115.2	H7B—C7—H7C	109.5
C3—C2—C1	92.46 (11)	O3—C8—N1	118.93 (13)
C3—C2—H2A	113.2	O3—C8—C9	122.94 (13)
C1—C2—H2A	113.2	N1—C8—C9	117.83 (12)
C3—C2—H2B	113.2	C14—C9—C10	119.79 (14)
C1—C2—H2B	113.2	C14—C9—C8	118.21 (13)
H2A—C2—H2B	110.6	C10—C9—C8	121.87 (13)
O1—C3—C2	103.00 (12)	C11—C10—C9	119.94 (14)
O1—C3—C4	105.92 (11)	C11—C10—H10A	120.0
C2—C3—C4	103.54 (12)	C9—C10—H10A	120.0
O1—C3—H3A	114.4	C12—C11—C10	120.01 (15)
C2—C3—H3A	114.4	C12—C11—H11A	120.0
C4—C3—H3A	114.4	C10—C11—H11A	120.0
O2—C4—C3	111.21 (12)	C11—C12—C13	120.32 (15)
O2—C4—C5	105.13 (12)	C11—C12—H12A	119.8
C3—C4—C5	102.95 (11)	C13—C12—H12A	119.8
O2—C4—H4A	112.3	C12—C13—C14	120.05 (15)
C3—C4—H4A	112.3	C12—C13—H13A	120.0
C5—C4—H4A	112.3	C14—C13—H13A	120.0
C6—C5—C4	101.12 (11)	C13—C14—C9	119.87 (14)
C6—C5—C1	114.18 (11)	C13—C14—H14A	120.1
C4—C5—C1	101.61 (11)	C9—C14—H14A	120.1

C3—O1—N1—C8	−147.02 (12)	N1—C1—C5—C4	67.40 (13)
C3—O1—N1—C1	−1.68 (13)	C2—C1—C5—C4	−37.18 (14)
C4—O2—N2—C6	0.13 (15)	O2—N2—C6—C7	−179.40 (12)
C8—N1—C1—C2	179.42 (13)	O2—N2—C6—C5	0.08 (16)
O1—N1—C1—C2	36.62 (13)	C4—C5—C6—N2	−0.24 (15)
C8—N1—C1—C5	72.72 (16)	C1—C5—C6—N2	−108.48 (14)
O1—N1—C1—C5	−70.08 (13)	C4—C5—C6—C7	179.23 (13)
N1—C1—C2—C3	−53.69 (12)	C1—C5—C6—C7	70.99 (17)
C5—C1—C2—C3	56.34 (13)	O1—N1—C8—O3	154.39 (12)
N1—O1—C3—C2	−34.33 (13)	C1—N1—C8—O3	15.5 (2)
N1—O1—C3—C4	74.07 (12)	O1—N1—C8—C9	−31.74 (18)
C1—C2—C3—O1	54.66 (12)	C1—N1—C8—C9	−170.68 (12)
C1—C2—C3—C4	−55.54 (13)	O3—C8—C9—C14	−30.7 (2)
N2—O2—C4—C3	110.46 (13)	N1—C8—C9—C14	155.66 (13)
N2—O2—C4—C5	−0.27 (14)	O3—C8—C9—C10	145.16 (15)
O1—C3—C4—O2	174.48 (10)	N1—C8—C9—C10	−28.4 (2)
C2—C3—C4—O2	−77.50 (14)	C14—C9—C10—C11	−0.5 (2)
O1—C3—C4—C5	−73.40 (13)	C8—C9—C10—C11	−176.30 (14)
C2—C3—C4—C5	34.62 (14)	C9—C10—C11—C12	−0.8 (2)
O2—C4—C5—C6	0.29 (13)	C10—C11—C12—C13	1.2 (2)
C3—C4—C5—C6	−116.25 (12)	C11—C12—C13—C14	−0.4 (2)
O2—C4—C5—C1	118.09 (12)	C12—C13—C14—C9	−0.9 (2)
C3—C4—C5—C1	1.56 (14)	C10—C9—C14—C13	1.3 (2)
N1—C1—C5—C6	175.33 (11)	C8—C9—C14—C13	177.27 (13)
C2—C1—C5—C6	70.76 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3ⁱ	1.00	2.50	3.2793 (18)	135
C5—H5A···O2ⁱⁱ	1.00	2.59	3.4017 (18)	138
C7—H7B···O2ⁱⁱ	0.98	2.56	3.3900 (19)	142
C7—H7C···O2ⁱⁱⁱ	0.98	2.60	3.568 (2)	170
C11—H11A···O3^iv	0.95	2.58	3.470 (2)	156

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3ⁱ	1.00	2.50	3.2793 (18)	135
C5—H5A···O2ⁱⁱ	1.00	2.59	3.4017 (18)	138
C7—H7B···O2ⁱⁱ	0.98	2.56	3.3900 (19)	142
C7—H7C···O2ⁱⁱⁱ	0.98	2.60	3.568 (2)	170
C11—H11A···O3^iv	0.95	2.58	3.470 (2)	156

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

Acknowledgements

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).

References

Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lough, A. J., Nagireddy, J. R. & Tam, W. (2014). Acta Cryst. E70, o544. CSD CrossRef IUCr Journals Google Scholar
Mayo, P., Hecnar, T. & Tam, W. (2001). Tetrahedron, 57, 5931–5941. Web of Science CrossRef CAS Google Scholar
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Volume 70| Part 5| May 2014| Page o543

doi:10.1107/S1600536814007740

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

(3-Methyl-3a,4,7,7a-tetra­hydro-5H-4,7-methano­isoxazolo[4,5-d][1,2]oxazin-5-yl)(phen­yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3-Methyl-3a,4,7,7a-tetrahydro-5H-4,7-methanoisoxazolo[4,5-d][1,2]oxazin-5-yl)(phenyl)methanone