(3-Methyl-3a,4,7,7a-tetra-hydro-5H-4,7-methano-isoxazolo[4,5-d][1,2]oxazin-5-yl)(phen-yl)methanone.

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 mol-ecules, forming a three-dimensional network. The isoxazole O atom is an acceptor for three of these hydrogen bonds.

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 = 258.27

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.101

S = 1.03

2854 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

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

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

Click here for additional data file.

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

CCDC reference: 995952

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H14N2O3	Dx = 1.384 Mg m−3
Mr = 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

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

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(Fo2) + (0.0436P)2 + 0.7731P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2854 reflections	Δρmax = 0.28 e Å−3
173 parameters	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O3iv	0.95	2.58	3.470 (2)	156

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⋯O3iv	0.95	2.58	3.470 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .