5,8-Dimeth­oxy-3,9-dimethyl-3a,4,9,9a-tetra­hydro-4,9-ep­oxy­naphtho­[2,3-d]isoxazole

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

doi:10.1107/S1600536814007752

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o544

doi:10.1107/S1600536814007752

Open

access

5,8-Dimethoxy-3,9-dimethyl-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3-d]isoxazole

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, C₁₅H₁₇NO₄, is the exo isomer with a syn arrangement of the O atom in the isoxazole ring to the methyl group of the bicyclic alkene. The dihedral angle between the isoxazole ring and the benzene ring is 7.42 (9)°. In the crystal, weak C—H⋯O hydrogen bonds link molecules, forming a three-dimensional network. The isoxazole O atom is an acceptor for both weak hydrogen bonds.

CCDC reference: 995953

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

C₁₅H₁₇NO₄
M_r = 275.29
Monoclinic, P 2₁ /n
a = 9.0608 (12) Å
b = 14.3998 (17) Å
c = 10.1631 (12) Å
β = 104.835 (3)°
V = 1281.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 147 K
0.32 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.660, T_max = 0.746
11844 measured reflections
2937 independent reflections
2271 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.05
2937 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	1.00	2.35	3.2928 (17)	156
C14—H14C⋯O2ⁱⁱ	0.98	2.59	3.5340 (19)	161
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

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: 995953

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007752/is5351sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007752/is5351Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007752/is5351Isup3.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 reaction with C1-substituted oxabenzonorbornadienes, 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 89:11 respectively (ratio was determined by ¹H NMR). 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 (IV) obtained was found to be the product with the oxygen of the nitrile oxide syn to the C1-methyl group of the bicyclic alkene.

The molecular structure of the title compound is shown in Fig. 2. The dihedral angle between the isoxazole ring (C4/C5/C6/O2/N1 with an r.m.s. deviation 0.0125 Å) and the benzene ring (C8–C13) is 7.42 (9)°. 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 both weak 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) (130.0 mg, 1.733 mmol) in toluene (2 ml) was added to a flame-dried flask containing bicyclic alkene (II) (140 mg, 0.642 mmol), (BOC)₂O (233.7 mg, 1.07 mmol), DMAP (9.4 mg, 0.077 mmol) and toluene (6 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 8:2) followed by recrystallization in methanol to give cycloadduct (IV) in 70% yield. Recrystallization of a solution of the title compound in MeOH provided crystals suitable for X-ray diffraction.

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.

5,8-Dimethoxy-3,9-dimethyl-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3-d]isoxazole top

Crystal data top

C₁₅H₁₇NO₄	F(000) = 584
M_r = 275.29	D_x = 1.427 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0608 (12) Å	Cell parameters from 2761 reflections
b = 14.3998 (17) Å	θ = 2.5–27.5°
c = 10.1631 (12) Å	µ = 0.10 mm⁻¹
β = 104.835 (3)°	T = 147 K
V = 1281.8 (3) Å³	Needle, colourless
Z = 4	0.32 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2271 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→11
T_min = 0.660, T_max = 0.746	k = −18→17
11844 measured reflections	l = −11→13
2937 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0459P)² + 0.2574P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2937 reflections	Δρ_max = 0.28 e Å⁻³
185 parameters	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₇NO₄	V = 1281.8 (3) Å³
M_r = 275.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0608 (12) Å	µ = 0.10 mm⁻¹
b = 14.3998 (17) Å	T = 147 K
c = 10.1631 (12) Å	0.32 × 0.16 × 0.14 mm
β = 104.835 (3)°

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2937 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	2271 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.746	R_int = 0.041
11844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
2937 reflections	Δρ_min = −0.22 e Å⁻³
185 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	0.50314 (11)	0.25637 (7)	0.36251 (9)	0.0158 (2)
O2	0.59142 (11)	0.27152 (7)	0.66027 (10)	0.0199 (2)
O3	0.27204 (11)	0.49102 (7)	0.15675 (10)	0.0217 (2)
O4	0.89378 (11)	0.43196 (7)	0.37701 (10)	0.0205 (2)
N1	0.44029 (14)	0.24274 (9)	0.65909 (12)	0.0200 (3)
C1	0.39743 (15)	0.33293 (10)	0.34640 (13)	0.0147 (3)
H1A	0.2909	0.3190	0.2927	0.018*
C2	0.63942 (15)	0.30606 (9)	0.43544 (13)	0.0147 (3)
C3	0.77661 (17)	0.24375 (10)	0.46760 (15)	0.0201 (3)
H3A	0.8081	0.2309	0.3841	0.030*
H3B	0.7510	0.1853	0.5060	0.030*
H3C	0.8603	0.2743	0.5338	0.030*
C4	0.58557 (15)	0.34340 (10)	0.55933 (13)	0.0148 (3)
H4A	0.6418	0.4007	0.5992	0.018*
C5	0.41454 (15)	0.36162 (10)	0.49764 (13)	0.0141 (3)
H5A	0.3833	0.4272	0.5086	0.017*
C6	0.34470 (16)	0.29242 (10)	0.57416 (14)	0.0162 (3)
C7	0.17703 (16)	0.27995 (11)	0.55319 (15)	0.0203 (3)
H7A	0.1580	0.2282	0.6092	0.030*
H7B	0.1300	0.2665	0.4570	0.030*
H7C	0.1328	0.3369	0.5795	0.030*
C8	0.47998 (16)	0.40647 (10)	0.28645 (13)	0.0145 (3)
C9	0.42749 (16)	0.48105 (10)	0.20091 (14)	0.0163 (3)
C10	0.53678 (17)	0.53792 (10)	0.16776 (14)	0.0178 (3)
H10A	0.5052	0.5885	0.1070	0.021*
C11	0.69228 (17)	0.52157 (10)	0.22265 (14)	0.0182 (3)
H11A	0.7647	0.5609	0.1976	0.022*
C12	0.74383 (16)	0.44869 (10)	0.31354 (13)	0.0153 (3)
C13	0.63422 (15)	0.39029 (9)	0.34279 (13)	0.0144 (3)
C14	0.21634 (18)	0.57380 (10)	0.08270 (15)	0.0220 (3)
H14A	0.1046	0.5751	0.0622	0.033*
H14B	0.2481	0.5748	−0.0025	0.033*
H14C	0.2581	0.6282	0.1376	0.033*
C15	1.00530 (17)	0.47219 (11)	0.31725 (16)	0.0227 (3)
H15A	1.1070	0.4499	0.3652	0.034*
H15B	1.0019	0.5400	0.3244	0.034*
H15C	0.9835	0.4543	0.2212	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0159 (5)	0.0130 (5)	0.0180 (5)	−0.0010 (4)	0.0035 (4)	−0.0021 (4)
O2	0.0152 (5)	0.0255 (6)	0.0188 (5)	0.0024 (4)	0.0042 (4)	0.0073 (4)
O3	0.0169 (5)	0.0212 (6)	0.0255 (5)	0.0018 (4)	0.0029 (4)	0.0078 (4)
O4	0.0145 (5)	0.0259 (6)	0.0217 (5)	−0.0024 (4)	0.0057 (4)	0.0032 (4)
N1	0.0188 (6)	0.0216 (7)	0.0211 (6)	−0.0009 (5)	0.0077 (5)	0.0020 (5)
C1	0.0149 (7)	0.0139 (7)	0.0149 (6)	−0.0003 (5)	0.0031 (5)	−0.0003 (5)
C2	0.0140 (7)	0.0143 (7)	0.0161 (6)	−0.0012 (5)	0.0044 (5)	−0.0019 (5)
C3	0.0192 (8)	0.0183 (7)	0.0240 (7)	0.0035 (6)	0.0077 (6)	0.0010 (6)
C4	0.0161 (7)	0.0142 (7)	0.0144 (6)	0.0005 (5)	0.0043 (5)	0.0010 (5)
C5	0.0140 (7)	0.0133 (7)	0.0153 (6)	−0.0003 (5)	0.0044 (5)	−0.0005 (5)
C6	0.0197 (7)	0.0140 (7)	0.0159 (6)	−0.0006 (6)	0.0065 (5)	−0.0013 (5)
C7	0.0180 (8)	0.0220 (8)	0.0228 (7)	−0.0016 (6)	0.0088 (6)	0.0004 (6)
C8	0.0171 (7)	0.0139 (7)	0.0135 (6)	−0.0013 (5)	0.0055 (5)	−0.0025 (5)
C9	0.0171 (7)	0.0177 (7)	0.0140 (6)	0.0011 (6)	0.0035 (5)	−0.0008 (5)
C10	0.0241 (8)	0.0148 (7)	0.0149 (6)	0.0005 (6)	0.0058 (6)	0.0009 (5)
C11	0.0219 (8)	0.0173 (7)	0.0176 (7)	−0.0046 (6)	0.0092 (6)	−0.0027 (6)
C12	0.0151 (7)	0.0175 (7)	0.0144 (6)	−0.0007 (6)	0.0060 (5)	−0.0031 (5)
C13	0.0178 (7)	0.0133 (7)	0.0127 (6)	0.0007 (5)	0.0048 (5)	−0.0026 (5)
C14	0.0232 (8)	0.0204 (8)	0.0209 (7)	0.0060 (6)	0.0029 (6)	0.0048 (6)
C15	0.0165 (7)	0.0279 (8)	0.0256 (8)	−0.0038 (6)	0.0091 (6)	0.0005 (6)

Geometric parameters (Å, º) top

O1—C1	1.4420 (16)	C5—C6	1.5001 (19)
O1—C2	1.4550 (16)	C5—H5A	1.0000
O2—N1	1.4278 (16)	C6—C7	1.490 (2)
O2—C4	1.4487 (16)	C7—H7A	0.9800
O3—C9	1.3719 (17)	C7—H7B	0.9800
O3—C14	1.4309 (17)	C7—H7C	0.9800
O4—C12	1.3680 (17)	C8—C9	1.387 (2)
O4—C15	1.4282 (17)	C8—C13	1.3877 (19)
N1—C6	1.2744 (19)	C9—C10	1.391 (2)
C1—C8	1.5118 (18)	C10—C11	1.396 (2)
C1—C5	1.5605 (18)	C10—H10A	0.9500
C1—H1A	1.0000	C11—C12	1.397 (2)
C2—C3	1.4997 (19)	C11—H11A	0.9500
C2—C13	1.5288 (19)	C12—C13	1.3903 (19)
C2—C4	1.5580 (18)	C14—H14A	0.9800
C3—H3A	0.9800	C14—H14B	0.9800
C3—H3B	0.9800	C14—H14C	0.9800
C3—H3C	0.9800	C15—H15A	0.9800
C4—C5	1.5381 (18)	C15—H15B	0.9800
C4—H4A	1.0000	C15—H15C	0.9800

C1—O1—C2	97.72 (10)	C7—C6—C5	123.78 (12)
N1—O2—C4	109.89 (10)	C6—C7—H7A	109.5
C9—O3—C14	116.97 (11)	C6—C7—H7B	109.5
C12—O4—C15	116.97 (11)	H7A—C7—H7B	109.5
C6—N1—O2	109.07 (11)	C6—C7—H7C	109.5
O1—C1—C8	101.45 (10)	H7A—C7—H7C	109.5
O1—C1—C5	101.24 (10)	H7B—C7—H7C	109.5
C8—C1—C5	106.07 (11)	C9—C8—C13	122.42 (13)
O1—C1—H1A	115.4	C9—C8—C1	132.02 (13)
C8—C1—H1A	115.4	C13—C8—C1	105.43 (12)
C5—C1—H1A	115.4	O3—C9—C8	116.40 (12)
O1—C2—C3	111.39 (11)	O3—C9—C10	126.44 (13)
O1—C2—C13	100.84 (10)	C8—C9—C10	117.16 (13)
C3—C2—C13	120.13 (12)	C9—C10—C11	120.80 (13)
O1—C2—C4	100.42 (10)	C9—C10—H10A	119.6
C3—C2—C4	116.36 (11)	C11—C10—H10A	119.6
C13—C2—C4	104.91 (11)	C10—C11—C12	121.55 (13)
C2—C3—H3A	109.5	C10—C11—H11A	119.2
C2—C3—H3B	109.5	C12—C11—H11A	119.2
H3A—C3—H3B	109.5	O4—C12—C13	118.06 (12)
C2—C3—H3C	109.5	O4—C12—C11	124.58 (13)
H3A—C3—H3C	109.5	C13—C12—C11	117.35 (13)
H3B—C3—H3C	109.5	C8—C13—C12	120.62 (13)
O2—C4—C5	105.12 (11)	C8—C13—C2	104.85 (12)
O2—C4—C2	111.31 (11)	C12—C13—C2	134.47 (13)
C5—C4—C2	102.75 (10)	O3—C14—H14A	109.5
O2—C4—H4A	112.3	O3—C14—H14B	109.5
C5—C4—H4A	112.3	H14A—C14—H14B	109.5
C2—C4—H4A	112.3	O3—C14—H14C	109.5
C6—C5—C4	100.96 (11)	H14A—C14—H14C	109.5
C6—C5—C1	112.71 (11)	H14B—C14—H14C	109.5
C4—C5—C1	101.07 (11)	O4—C15—H15A	109.5
C6—C5—H5A	113.6	O4—C15—H15B	109.5
C4—C5—H5A	113.6	H15A—C15—H15B	109.5
C1—C5—H5A	113.6	O4—C15—H15C	109.5
N1—C6—C7	121.36 (13)	H15A—C15—H15C	109.5
N1—C6—C5	114.85 (13)	H15B—C15—H15C	109.5

C4—O2—N1—C6	−3.33 (15)	O1—C1—C8—C13	−32.41 (13)
C2—O1—C1—C8	51.19 (11)	C5—C1—C8—C13	72.97 (13)
C2—O1—C1—C5	−57.97 (11)	C14—O3—C9—C8	172.37 (12)
C1—O1—C2—C3	−179.30 (11)	C14—O3—C9—C10	−8.0 (2)
C1—O1—C2—C13	−50.69 (11)	C13—C8—C9—O3	−177.44 (12)
C1—O1—C2—C4	56.86 (11)	C1—C8—C9—O3	−2.2 (2)
N1—O2—C4—C5	2.76 (13)	C13—C8—C9—C10	2.9 (2)
N1—O2—C4—C2	−107.78 (12)	C1—C8—C9—C10	178.11 (13)
O1—C2—C4—O2	78.42 (12)	O3—C9—C10—C11	178.30 (13)
C3—C2—C4—O2	−41.92 (16)	C8—C9—C10—C11	−2.1 (2)
C13—C2—C4—O2	−177.29 (11)	C9—C10—C11—C12	−0.8 (2)
O1—C2—C4—C5	−33.63 (12)	C15—O4—C12—C13	161.27 (12)
C3—C2—C4—C5	−153.97 (12)	C15—O4—C12—C11	−19.88 (19)
C13—C2—C4—C5	70.66 (12)	C10—C11—C12—O4	−176.08 (12)
O2—C4—C5—C6	−1.30 (13)	C10—C11—C12—C13	2.8 (2)
C2—C4—C5—C6	115.27 (11)	C9—C8—C13—C12	−0.9 (2)
O2—C4—C5—C1	−117.31 (11)	C1—C8—C13—C12	−177.18 (12)
C2—C4—C5—C1	−0.74 (13)	C9—C8—C13—C2	176.63 (12)
O1—C1—C5—C6	−71.58 (13)	C1—C8—C13—C2	0.31 (13)
C8—C1—C5—C6	−177.12 (11)	O4—C12—C13—C8	176.95 (12)
O1—C1—C5—C4	35.38 (12)	C11—C12—C13—C8	−1.98 (19)
C8—C1—C5—C4	−70.15 (13)	O4—C12—C13—C2	0.3 (2)
O2—N1—C6—C7	−178.46 (12)	C11—C12—C13—C2	−178.59 (14)
O2—N1—C6—C5	2.48 (16)	O1—C2—C13—C8	31.49 (13)
C4—C5—C6—N1	−0.72 (15)	C3—C2—C13—C8	154.22 (12)
C1—C5—C6—N1	106.32 (14)	C4—C2—C13—C8	−72.49 (13)
C4—C5—C6—C7	−179.75 (13)	O1—C2—C13—C12	−151.53 (15)
C1—C5—C6—C7	−72.71 (17)	C3—C2—C13—C12	−28.8 (2)
O1—C1—C8—C9	151.77 (14)	C4—C2—C13—C12	104.49 (17)
C5—C1—C8—C9	−102.85 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	1.00	2.35	3.2928 (17)	156
C14—H14C···O2ⁱⁱ	0.98	2.59	3.5340 (19)	161

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	1.00	2.35	3.2928 (17)	156
C14—H14C···O2ⁱⁱ	0.98	2.59	3.5340 (19)	161

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

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, o543. CSD CrossRef IUCr Journals Google Scholar
Mayo, P., Hecnar, T. & Tam, W. (2001). Tetrahedron, 57, 5931–5941. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yip, C., Handerson, S., Tranmer, G. K. & Tam, W. (2001). J. Org. Chem. 66, 276–286. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o544

doi:10.1107/S1600536814007752

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

5,8-Dimeth­­oxy-3,9-di­methyl-3a,4,9,9a-tetra­hydro-4,9-ep­­oxy­naphtho­[2,3-d]isoxazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,8-Dimethoxy-3,9-dimethyl-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3-d]isoxazole