1-(3-Hy-droxy-5,8-dimeth-oxy-4-methyl-1,2,3,4-tetra-hydro-1,4-ep-oxy-naphthalen-2-yl)ethan-1-one.

The stereochemistry and regioschemistry (exo) of the title compound, C15H18O5, were determined by the X-ray analysis. The meth-oxy groups essentially lie in the plane of the benzene ring to which they are attached, as described by the C-O-C C torsion angles of -176.80 (12) and 4.67 (19)°. In the crystal, O-H⋯O hydrogen bonds and weak C-H⋯O hydrogen bonds link the mol-ecules, forming chains of R 2 (1)(8) rings along [010].

Related literature

For the metal-mediated cleavage of 2-isoxazoline rings fused to bicyclic frameworks, see: Tranmer & Tam (2002 ▶). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H18O5

M = 278.29

Orthorhombic,

a = 10.3091 (4) Å

b = 9.1309 (4) Å

c = 29.2552 (13) Å

V = 2753.8 (2) Å3

Z = 8

Cu Kα radiation

μ = 0.84 mm−1

T = 147 K

0.17 × 0.14 × 0.05 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.686, T max = 0.753

9265 measured reflections

2368 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.04

2368 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.24 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/S1600536814007764/tk5301sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007764/tk5301Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007764/tk5301Isup3.cml

CCDC reference: 995954

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

C15H18O5	Dx = 1.342 Mg m−3
Mr = 278.29	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 6136 reflections
a = 10.3091 (4) Å	θ = 5.3–66.6°
b = 9.1309 (4) Å	µ = 0.84 mm−1
c = 29.2552 (13) Å	T = 147 K
V = 2753.8 (2) Å3	Plate, colourless
Z = 8	0.17 × 0.14 × 0.05 mm
F(000) = 1184

Bruker Kappa APEX DUO CCD diffractometer	2195 reflections with I > 2σ(I)
Radiation source: Bruker ImuS with multi-layer optics	Rint = 0.021
φ and ω scans	θmax = 66.6°, θmin = 5.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→10
Tmin = 0.686, Tmax = 0.753	k = −6→10
9265 measured reflections	l = −34→34
2368 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0532P)2 + 1.2534P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2368 reflections	Δρmax = 0.42 e Å−3
189 parameters	Δρmin = −0.24 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	0.88037 (9)	0.52360 (10)	0.62898 (3)	0.0212 (2)
O2	0.70291 (9)	0.72212 (11)	0.58154 (3)	0.0259 (2)
O3	0.85382 (10)	0.46468 (11)	0.52476 (3)	0.0294 (3)
O4	0.93569 (9)	0.88101 (11)	0.72203 (3)	0.0267 (2)
O5	1.28252 (9)	0.59024 (12)	0.60787 (3)	0.0315 (3)
C1	0.99163 (13)	0.55891 (15)	0.60115 (4)	0.0212 (3)
H1A	1.0361	0.4727	0.5871	0.025*
C2	0.85197 (12)	0.67220 (14)	0.64418 (4)	0.0192 (3)
C3	0.73874 (13)	0.67520 (16)	0.67653 (4)	0.0250 (3)
H3A	0.7645	0.6323	0.7059	0.038*
H3B	0.6669	0.6185	0.6636	0.038*
H3C	0.7109	0.7767	0.6813	0.038*
C4	0.83079 (12)	0.74951 (14)	0.59729 (4)	0.0194 (3)
H4A	0.8488	0.8569	0.5994	0.023*
C5	0.93447 (13)	0.66931 (14)	0.56674 (4)	0.0204 (3)
H5A	1.0027	0.7399	0.5566	0.025*
C6	0.87214 (13)	0.59612 (15)	0.52575 (4)	0.0230 (3)
C7	0.84055 (16)	0.69186 (18)	0.48585 (5)	0.0328 (4)
H7A	0.7895	0.6362	0.4636	0.049*
H7B	0.9211	0.7256	0.4715	0.049*
H7C	0.7903	0.7766	0.4963	0.049*
C8	0.98548 (13)	0.71876 (14)	0.66166 (4)	0.0192 (3)
C9	1.02832 (13)	0.81205 (14)	0.69594 (4)	0.0212 (3)
C10	1.16170 (14)	0.82634 (16)	0.70211 (5)	0.0259 (3)
H10A	1.1935	0.8868	0.7261	0.031*
C11	1.24964 (14)	0.75349 (16)	0.67375 (5)	0.0276 (3)
H11A	1.3401	0.7656	0.6786	0.033*
C12	1.20648 (13)	0.66370 (15)	0.63864 (5)	0.0242 (3)
C13	1.07345 (13)	0.64562 (15)	0.63424 (4)	0.0213 (3)
C14	0.98079 (15)	0.98213 (16)	0.75556 (5)	0.0299 (3)
H14A	0.9064	1.0277	0.7708	0.045*
H14B	1.0333	1.0580	0.7407	0.045*
H14C	1.0337	0.9302	0.7782	0.045*
C15	1.41953 (14)	0.60214 (19)	0.61366 (6)	0.0354 (4)
H15A	1.4636	0.5488	0.5891	0.053*
H15B	1.4443	0.5603	0.6433	0.053*
H15C	1.4448	0.7055	0.6126	0.053*
H2O	0.673 (2)	0.813 (3)	0.5676 (8)	0.072 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0214 (5)	0.0188 (5)	0.0234 (5)	−0.0021 (4)	0.0009 (4)	−0.0006 (4)
O2	0.0188 (5)	0.0323 (6)	0.0267 (5)	0.0002 (4)	−0.0033 (4)	−0.0005 (4)
O3	0.0325 (6)	0.0294 (6)	0.0263 (5)	−0.0037 (4)	−0.0013 (4)	−0.0039 (4)
O4	0.0249 (5)	0.0278 (5)	0.0274 (5)	0.0002 (4)	−0.0040 (4)	−0.0091 (4)
O5	0.0177 (5)	0.0428 (6)	0.0341 (6)	0.0056 (4)	0.0026 (4)	0.0006 (5)
C1	0.0181 (7)	0.0226 (7)	0.0227 (7)	0.0012 (5)	0.0010 (5)	−0.0012 (5)
C2	0.0179 (7)	0.0183 (7)	0.0214 (6)	−0.0010 (5)	−0.0006 (5)	−0.0021 (5)
C3	0.0199 (7)	0.0322 (8)	0.0229 (7)	−0.0026 (6)	0.0019 (5)	−0.0003 (6)
C4	0.0155 (6)	0.0210 (7)	0.0217 (7)	−0.0008 (5)	−0.0009 (5)	−0.0013 (5)
C5	0.0177 (7)	0.0215 (7)	0.0221 (7)	0.0000 (5)	0.0016 (5)	0.0001 (5)
C6	0.0185 (7)	0.0280 (8)	0.0225 (7)	0.0030 (5)	0.0035 (5)	−0.0016 (6)
C7	0.0397 (9)	0.0377 (9)	0.0211 (7)	0.0107 (7)	−0.0001 (6)	−0.0010 (6)
C8	0.0183 (7)	0.0187 (6)	0.0208 (6)	−0.0008 (5)	−0.0017 (5)	0.0034 (5)
C9	0.0224 (7)	0.0198 (6)	0.0214 (6)	−0.0005 (5)	−0.0027 (5)	0.0021 (5)
C10	0.0250 (8)	0.0255 (7)	0.0271 (7)	−0.0057 (6)	−0.0075 (6)	0.0017 (6)
C11	0.0185 (7)	0.0324 (8)	0.0319 (7)	−0.0034 (6)	−0.0059 (6)	0.0063 (6)
C12	0.0184 (7)	0.0270 (7)	0.0273 (7)	0.0020 (6)	0.0004 (5)	0.0062 (6)
C13	0.0199 (7)	0.0215 (7)	0.0223 (7)	0.0008 (5)	−0.0013 (5)	0.0033 (5)
C14	0.0334 (8)	0.0292 (7)	0.0270 (7)	−0.0034 (6)	−0.0042 (6)	−0.0093 (6)
C15	0.0171 (8)	0.0468 (10)	0.0422 (9)	0.0059 (7)	0.0030 (6)	0.0146 (7)

O1—C1	1.4431 (16)	C5—C6	1.5157 (18)
O1—C2	1.4576 (16)	C5—H5A	1.0000
O2—C4	1.4187 (16)	C6—C7	1.494 (2)
O2—H2O	0.97 (3)	C7—H7A	0.9800
O3—C6	1.2153 (18)	C7—H7B	0.9800
O4—C9	1.3750 (17)	C7—H7C	0.9800
O4—C14	1.4252 (16)	C8—C13	1.3827 (19)
O5—C12	1.3692 (17)	C8—C9	1.3880 (19)
O5—C15	1.4268 (18)	C9—C10	1.393 (2)
C1—C13	1.5086 (19)	C10—C11	1.397 (2)
C1—C5	1.5417 (18)	C10—H10A	0.9500
C1—H1A	1.0000	C11—C12	1.387 (2)
C2—C3	1.5030 (18)	C11—H11A	0.9500
C2—C8	1.5286 (18)	C12—C13	1.387 (2)
C2—C4	1.5581 (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	1.5740 (18)	C15—H15B	0.9800
C4—H4A	1.0000	C15—H15C	0.9800
C1—O1—C2	97.11 (9)	C6—C7—H7A	109.5
C4—O2—H2O	106.0 (14)	C6—C7—H7B	109.5
C9—O4—C14	116.88 (11)	H7A—C7—H7B	109.5
C12—O5—C15	116.83 (12)	C6—C7—H7C	109.5
O1—C1—C13	101.51 (10)	H7A—C7—H7C	109.5
O1—C1—C5	102.17 (10)	H7B—C7—H7C	109.5
C13—C1—C5	106.84 (11)	C13—C8—C9	120.45 (12)
O1—C1—H1A	114.9	C13—C8—C2	105.20 (11)
C13—C1—H1A	114.9	C9—C8—C2	134.34 (12)
C5—C1—H1A	114.9	O4—C9—C8	117.45 (12)
O1—C2—C3	111.41 (11)	O4—C9—C10	124.81 (12)
O1—C2—C8	100.38 (10)	C8—C9—C10	117.72 (13)
C3—C2—C8	118.92 (11)	C9—C10—C11	121.26 (13)
O1—C2—C4	100.44 (10)	C9—C10—H10A	119.4
C3—C2—C4	115.93 (11)	C11—C10—H10A	119.4
C8—C2—C4	107.14 (10)	C12—C11—C10	120.85 (13)
C2—C3—H3A	109.5	C12—C11—H11A	119.6
C2—C3—H3B	109.5	C10—C11—H11A	119.6
H3A—C3—H3B	109.5	O5—C12—C13	116.53 (12)
C2—C3—H3C	109.5	O5—C12—C11	126.35 (13)
H3A—C3—H3C	109.5	C13—C12—C11	117.12 (13)
H3B—C3—H3C	109.5	C8—C13—C12	122.49 (13)
O2—C4—C2	109.65 (10)	C8—C13—C1	105.01 (11)
O2—C4—C5	111.38 (10)	C12—C13—C1	132.43 (13)
C2—C4—C5	101.19 (10)	O4—C14—H14A	109.5
O2—C4—H4A	111.4	O4—C14—H14B	109.5
C2—C4—H4A	111.4	H14A—C14—H14B	109.5
C5—C4—H4A	111.4	O4—C14—H14C	109.5
C6—C5—C1	112.97 (11)	H14A—C14—H14C	109.5
C6—C5—C4	111.50 (11)	H14B—C14—H14C	109.5
C1—C5—C4	101.12 (10)	O5—C15—H15A	109.5
C6—C5—H5A	110.3	O5—C15—H15B	109.5
C1—C5—H5A	110.3	H15A—C15—H15B	109.5
C4—C5—H5A	110.3	O5—C15—H15C	109.5
O3—C6—C7	121.69 (13)	H15A—C15—H15C	109.5
O3—C6—C5	121.34 (12)	H15B—C15—H15C	109.5
C7—C6—C5	116.90 (12)
C2—O1—C1—C13	52.14 (11)	C3—C2—C8—C9	−27.1 (2)
C2—O1—C1—C5	−58.12 (11)	C4—C2—C8—C9	106.73 (16)
C1—O1—C2—C3	−178.08 (10)	C14—O4—C9—C8	−176.91 (12)
C1—O1—C2—C8	−51.22 (11)	C14—O4—C9—C10	4.67 (19)
C1—O1—C2—C4	58.56 (10)	C13—C8—C9—O4	−179.83 (11)
O1—C2—C4—O2	81.46 (11)	C2—C8—C9—O4	1.0 (2)
C3—C2—C4—O2	−38.70 (15)	C13—C8—C9—C10	−1.29 (19)
C8—C2—C4—O2	−174.15 (10)	C2—C8—C9—C10	179.56 (13)
O1—C2—C4—C5	−36.26 (11)	O4—C9—C10—C11	−179.33 (12)
C3—C2—C4—C5	−156.42 (11)	C8—C9—C10—C11	2.2 (2)
C8—C2—C4—C5	68.13 (12)	C9—C10—C11—C12	−0.4 (2)
O1—C1—C5—C6	−85.45 (12)	C15—O5—C12—C13	−176.80 (12)
C13—C1—C5—C6	168.38 (11)	C15—O5—C12—C11	2.9 (2)
O1—C1—C5—C4	33.82 (12)	C10—C11—C12—O5	177.95 (13)
C13—C1—C5—C4	−72.35 (12)	C10—C11—C12—C13	−2.4 (2)
O2—C4—C5—C6	5.64 (15)	C9—C8—C13—C12	−1.6 (2)
C2—C4—C5—C6	122.10 (11)	C2—C8—C13—C12	177.80 (12)
O2—C4—C5—C1	−114.69 (11)	C9—C8—C13—C1	−178.95 (11)
C2—C4—C5—C1	1.77 (12)	C2—C8—C13—C1	0.42 (13)
C1—C5—C6—O3	10.24 (18)	O5—C12—C13—C8	−176.91 (12)
C4—C5—C6—O3	−102.85 (14)	C11—C12—C13—C8	3.4 (2)
C1—C5—C6—C7	−166.79 (12)	O5—C12—C13—C1	−0.3 (2)
C4—C5—C6—C7	80.12 (15)	C11—C12—C13—C1	179.95 (13)
O1—C2—C8—C13	31.93 (12)	O1—C1—C13—C8	−33.15 (13)
C3—C2—C8—C13	153.61 (12)	C5—C1—C13—C8	73.48 (13)
C4—C2—C8—C13	−72.51 (12)	O1—C1—C13—C12	149.85 (14)
O1—C2—C8—C9	−148.83 (14)	C5—C1—C13—C12	−103.52 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3i	0.97 (3)	1.89 (2)	2.8295 (15)	162 (2)
C7—H7C···O3i	0.98	2.42	3.3936 (19)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3i	0.97 (3)	1.89 (2)	2.8295 (15)	162 (2)
C7—H7C⋯O3i	0.98	2.42	3.3936 (19)	173

Symmetry code: (i) .