10a-Hy-droxy-9-(4-meth-oxy-phen-yl)-3,4,5,6,7,8a,9,10a-octa-hydro-1H-xanthene-1,8(2H)-dione.

In the title compound, C(20)H(22)O(5), the tetra-hydro-pyran, cyclo-hexene and cyclo-hexane rings of the xanthene ring system adopt half-chair, half-boat and chair conformations, respectively. The mean plane of the four roughly planar atoms of the tetra-hydro-pyran ring (r.m.s. deviation = 0.111 Å) forms a dihedral angle of 82.91 (4)° with the meth-oxy-benzene group. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal is further consolidated by weak C-H⋯π inter-actions.

Related literature

For background to the applications of xanthene, see: Menchen et al. (2003 ▶); Knight & Stephens (1989 ▶). For our previous studies in this area, see: Palakshi Reddy et al. (2010 ▶); Reddy et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For a related structure, see: Loh et al. (2011 ▶). For bond length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H22O5

M = 342.38

Orthorhombic,

a = 15.7611 (9) Å

b = 18.0089 (11) Å

c = 11.6451 (7) Å

V = 3305.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.48 × 0.23 × 0.11 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.954, T max = 0.990

97212 measured reflections

7190 independent reflections

6068 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.05

7190 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203005X/hb6880sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203005X/hb6880Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203005X/hb6880Isup3.cml

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

C20H22O5	F(000) = 1456
Mr = 342.38	Dx = 1.376 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9871 reflections
a = 15.7611 (9) Å	θ = 2.6–34.8°
b = 18.0089 (11) Å	µ = 0.10 mm−1
c = 11.6451 (7) Å	T = 100 K
V = 3305.3 (3) Å3	Block, colourless
Z = 8	0.48 × 0.23 × 0.11 mm

Bruker APEX DUO CCD diffractometer	7190 independent reflections
Radiation source: fine-focus sealed tube	6068 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 34.8°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→25
Tmin = 0.954, Tmax = 0.990	k = −28→28
97212 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.059P)2 + 0.8159P] where P = (Fo2 + 2Fc2)/3
7190 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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.

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 > σ(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
O1	0.41955 (4)	0.43646 (3)	−0.11953 (4)	0.01606 (10)
O2	0.12092 (4)	0.39264 (4)	0.24042 (6)	0.02378 (13)
O3	0.35506 (4)	0.19277 (3)	0.24263 (5)	0.01785 (11)
O4	0.18491 (3)	0.32355 (3)	0.50833 (5)	0.01370 (10)
O5	0.32107 (3)	0.36949 (3)	0.53699 (4)	0.01306 (10)
C1	0.38478 (5)	0.41214 (5)	−0.22594 (6)	0.01835 (14)
H1A	0.4187	0.4321	−0.2894	0.028*
H1B	0.3262	0.4299	−0.2328	0.028*
H1C	0.3855	0.3578	−0.2289	0.028*
C2	0.38251 (4)	0.40829 (4)	−0.02218 (5)	0.01168 (11)
C3	0.42230 (5)	0.42661 (4)	0.08114 (6)	0.01375 (12)
H3A	0.4718	0.4567	0.0811	0.016*
C4	0.38909 (4)	0.40059 (4)	0.18390 (6)	0.01299 (11)
H4A	0.4165	0.4130	0.2540	0.016*
C5	0.31611 (4)	0.35644 (4)	0.18628 (5)	0.01067 (11)
C6	0.27766 (4)	0.33891 (4)	0.08261 (6)	0.01223 (11)
H6A	0.2279	0.3092	0.0828	0.015*
C7	0.31024 (4)	0.36386 (4)	−0.02199 (6)	0.01273 (11)
H7A	0.2834	0.3507	−0.0921	0.015*
C8	0.27857 (4)	0.33101 (4)	0.30012 (5)	0.01100 (11)
H8A	0.2310	0.2958	0.2841	0.013*
C9	0.34387 (4)	0.29187 (4)	0.37349 (5)	0.01071 (11)
C10	0.37999 (4)	0.22215 (4)	0.33249 (6)	0.01227 (11)
C11	0.44481 (5)	0.18319 (4)	0.40660 (6)	0.01532 (12)
H11A	0.4845	0.1553	0.3568	0.018*
H11B	0.4155	0.1470	0.4568	0.018*
C12	0.49507 (5)	0.23714 (4)	0.48070 (6)	0.01564 (12)
H12A	0.5300	0.2698	0.4312	0.019*
H12B	0.5337	0.2092	0.5320	0.019*
C13	0.43452 (4)	0.28408 (4)	0.55218 (6)	0.01375 (12)
H13A	0.4103	0.2532	0.6144	0.016*
H13B	0.4664	0.3253	0.5882	0.016*
C14	0.36412 (4)	0.31523 (4)	0.48106 (6)	0.01110 (11)
C15	0.23657 (4)	0.38542 (4)	0.49304 (6)	0.01137 (11)
C16	0.20491 (5)	0.45323 (4)	0.55788 (6)	0.01448 (12)
H16A	0.2459	0.4945	0.5488	0.017*
H16B	0.2004	0.4415	0.6407	0.017*
C17	0.11806 (5)	0.47705 (4)	0.51201 (7)	0.01725 (13)
H17A	0.1003	0.5234	0.5509	0.021*
H17B	0.0758	0.4382	0.5303	0.021*
C18	0.11950 (5)	0.48996 (5)	0.38134 (7)	0.02103 (15)
H18A	0.0610	0.4990	0.3537	0.025*
H18B	0.1538	0.5346	0.3640	0.025*
C19	0.15647 (5)	0.42367 (4)	0.31926 (6)	0.01632 (13)
C20	0.24286 (4)	0.39890 (4)	0.36411 (6)	0.01216 (11)
H20A	0.2833	0.4409	0.3521	0.015*
H1O4	0.1773 (11)	0.3167 (9)	0.5830 (15)	0.044 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0198 (2)	0.0200 (2)	0.0083 (2)	−0.00409 (19)	0.00179 (17)	0.00088 (17)
O2	0.0187 (3)	0.0334 (3)	0.0192 (3)	0.0069 (2)	−0.0042 (2)	−0.0018 (2)
O3	0.0242 (3)	0.0162 (2)	0.0131 (2)	0.0013 (2)	−0.00347 (19)	−0.00439 (18)
O4	0.0146 (2)	0.0138 (2)	0.0126 (2)	−0.00304 (16)	0.00192 (16)	0.00182 (17)
O5	0.0119 (2)	0.0149 (2)	0.0124 (2)	0.00174 (16)	−0.00052 (16)	−0.00358 (16)
C1	0.0258 (4)	0.0206 (3)	0.0086 (3)	−0.0017 (3)	0.0007 (2)	−0.0008 (2)
C2	0.0138 (3)	0.0127 (3)	0.0085 (2)	0.0004 (2)	0.00115 (19)	0.00019 (19)
C3	0.0145 (3)	0.0166 (3)	0.0101 (2)	−0.0037 (2)	0.0003 (2)	0.0000 (2)
C4	0.0137 (3)	0.0161 (3)	0.0092 (2)	−0.0031 (2)	−0.0005 (2)	−0.0003 (2)
C5	0.0116 (2)	0.0115 (2)	0.0089 (2)	0.00015 (19)	0.00017 (19)	0.00024 (19)
C6	0.0130 (3)	0.0134 (3)	0.0103 (2)	−0.0016 (2)	−0.00051 (19)	−0.0007 (2)
C7	0.0144 (3)	0.0146 (3)	0.0092 (2)	−0.0012 (2)	−0.0010 (2)	−0.0008 (2)
C8	0.0113 (2)	0.0122 (2)	0.0095 (2)	−0.00026 (19)	0.00045 (19)	0.00068 (19)
C9	0.0119 (2)	0.0110 (2)	0.0093 (2)	0.00007 (19)	0.00030 (19)	−0.00021 (19)
C10	0.0143 (3)	0.0119 (2)	0.0106 (2)	−0.0004 (2)	0.0003 (2)	−0.0001 (2)
C11	0.0182 (3)	0.0133 (3)	0.0145 (3)	0.0032 (2)	−0.0021 (2)	−0.0012 (2)
C12	0.0130 (3)	0.0175 (3)	0.0164 (3)	0.0025 (2)	−0.0017 (2)	−0.0023 (2)
C13	0.0128 (3)	0.0165 (3)	0.0119 (3)	0.0010 (2)	−0.0021 (2)	−0.0016 (2)
C14	0.0110 (2)	0.0116 (2)	0.0107 (2)	−0.00030 (19)	0.00070 (19)	−0.00083 (19)
C15	0.0111 (3)	0.0117 (2)	0.0114 (2)	−0.00005 (19)	0.00047 (19)	−0.0001 (2)
C16	0.0159 (3)	0.0133 (3)	0.0143 (3)	0.0013 (2)	0.0031 (2)	−0.0016 (2)
C17	0.0165 (3)	0.0179 (3)	0.0173 (3)	0.0049 (2)	0.0041 (2)	0.0010 (2)
C18	0.0232 (3)	0.0223 (3)	0.0176 (3)	0.0103 (3)	0.0031 (3)	0.0032 (3)
C19	0.0157 (3)	0.0199 (3)	0.0133 (3)	0.0047 (2)	0.0021 (2)	0.0039 (2)
C20	0.0130 (3)	0.0132 (3)	0.0103 (2)	0.0011 (2)	0.0019 (2)	0.0011 (2)

O1—C2	1.3724 (8)	C9—C14	1.3595 (9)
O1—C1	1.4240 (9)	C9—C10	1.4590 (9)
O2—C19	1.2121 (10)	C10—C11	1.5102 (10)
O3—C10	1.2366 (8)	C11—C12	1.5220 (10)
O4—C15	1.3914 (8)	C11—H11A	0.9900
O4—H1O4	0.887 (17)	C11—H11B	0.9900
O5—C14	1.3561 (8)	C12—C13	1.5225 (10)
O5—C15	1.4552 (8)	C12—H12A	0.9900
C1—H1A	0.9800	C12—H12B	0.9900
C1—H1B	0.9800	C13—C14	1.4940 (10)
C1—H1C	0.9800	C13—H13A	0.9900
C2—C7	1.3919 (10)	C13—H13B	0.9900
C2—C3	1.3963 (9)	C15—C16	1.5201 (10)
C3—C4	1.3876 (9)	C15—C20	1.5241 (9)
C3—H3A	0.9500	C16—C17	1.5306 (11)
C4—C5	1.3986 (9)	C16—H16A	0.9900
C4—H4A	0.9500	C16—H16B	0.9900
C5—C6	1.3872 (9)	C17—C18	1.5395 (11)
C5—C8	1.5223 (9)	C17—H17A	0.9900
C6—C7	1.3961 (9)	C17—H17B	0.9900
C6—H6A	0.9500	C18—C19	1.5124 (11)
C7—H7A	0.9500	C18—H18A	0.9900
C8—C9	1.5120 (9)	C18—H18B	0.9900
C8—C20	1.5383 (9)	C19—C20	1.5250 (10)
C8—H8A	1.0000	C20—H20A	1.0000
C2—O1—C1	116.20 (6)	C13—C12—H12A	109.7
C15—O4—H1O4	108.5 (11)	C11—C12—H12B	109.7
C14—O5—C15	115.53 (5)	C13—C12—H12B	109.7
O1—C1—H1A	109.5	H12A—C12—H12B	108.2
O1—C1—H1B	109.5	C14—C13—C12	111.78 (6)
H1A—C1—H1B	109.5	C14—C13—H13A	109.3
O1—C1—H1C	109.5	C12—C13—H13A	109.3
H1A—C1—H1C	109.5	C14—C13—H13B	109.3
H1B—C1—H1C	109.5	C12—C13—H13B	109.3
O1—C2—C7	124.19 (6)	H13A—C13—H13B	107.9
O1—C2—C3	115.68 (6)	O5—C14—C9	123.23 (6)
C7—C2—C3	120.13 (6)	O5—C14—C13	112.08 (6)
C4—C3—C2	119.60 (6)	C9—C14—C13	124.67 (6)
C4—C3—H3A	120.2	O4—C15—O5	109.43 (5)
C2—C3—H3A	120.2	O4—C15—C16	112.80 (6)
C3—C4—C5	121.28 (6)	O5—C15—C16	106.51 (5)
C3—C4—H4A	119.4	O4—C15—C20	106.96 (5)
C5—C4—H4A	119.4	O5—C15—C20	108.57 (5)
C6—C5—C4	118.13 (6)	C16—C15—C20	112.50 (6)
C6—C5—C8	121.31 (6)	C15—C16—C17	110.21 (6)
C4—C5—C8	120.53 (6)	C15—C16—H16A	109.6
C5—C6—C7	121.69 (6)	C17—C16—H16A	109.6
C5—C6—H6A	119.2	C15—C16—H16B	109.6
C7—C6—H6A	119.2	C17—C16—H16B	109.6
C2—C7—C6	119.17 (6)	H16A—C16—H16B	108.1
C2—C7—H7A	120.4	C16—C17—C18	111.97 (6)
C6—C7—H7A	120.4	C16—C17—H17A	109.2
C9—C8—C5	111.58 (5)	C18—C17—H17A	109.2
C9—C8—C20	110.23 (5)	C16—C17—H17B	109.2
C5—C8—C20	108.97 (5)	C18—C17—H17B	109.2
C9—C8—H8A	108.7	H17A—C17—H17B	107.9
C5—C8—H8A	108.7	C19—C18—C17	111.03 (6)
C20—C8—H8A	108.7	C19—C18—H18A	109.4
C14—C9—C10	118.45 (6)	C17—C18—H18A	109.4
C14—C9—C8	122.42 (6)	C19—C18—H18B	109.4
C10—C9—C8	118.81 (6)	C17—C18—H18B	109.4
O3—C10—C9	121.41 (6)	H18A—C18—H18B	108.0
O3—C10—C11	119.98 (6)	O2—C19—C18	123.23 (7)
C9—C10—C11	118.47 (6)	O2—C19—C20	122.49 (7)
C10—C11—C12	112.31 (6)	C18—C19—C20	114.28 (6)
C10—C11—H11A	109.1	C15—C20—C19	109.02 (5)
C12—C11—H11A	109.1	C15—C20—C8	111.99 (5)
C10—C11—H11B	109.1	C19—C20—C8	113.16 (6)
C12—C11—H11B	109.1	C15—C20—H20A	107.5
H11A—C11—H11B	107.9	C19—C20—H20A	107.5
C11—C12—C13	109.76 (6)	C8—C20—H20A	107.5
C11—C12—H12A	109.7
C1—O1—C2—C7	−5.83 (10)	C10—C9—C14—O5	−165.29 (6)
C1—O1—C2—C3	173.89 (6)	C8—C9—C14—O5	8.13 (10)
O1—C2—C3—C4	179.92 (6)	C10—C9—C14—C13	13.68 (10)
C7—C2—C3—C4	−0.35 (11)	C8—C9—C14—C13	−172.89 (6)
C2—C3—C4—C5	−0.24 (11)	C12—C13—C14—O5	−166.48 (6)
C3—C4—C5—C6	0.28 (10)	C12—C13—C14—C9	14.45 (10)
C3—C4—C5—C8	−177.51 (6)	C14—O5—C15—O4	64.53 (7)
C4—C5—C6—C7	0.28 (10)	C14—O5—C15—C16	−173.25 (6)
C8—C5—C6—C7	178.05 (6)	C14—O5—C15—C20	−51.88 (7)
O1—C2—C7—C6	−179.41 (6)	O4—C15—C16—C17	−63.35 (7)
C3—C2—C7—C6	0.89 (10)	O5—C15—C16—C17	176.59 (5)
C5—C6—C7—C2	−0.86 (10)	C20—C15—C16—C17	57.76 (8)
C6—C5—C8—C9	128.25 (7)	C15—C16—C17—C18	−54.64 (8)
C4—C5—C8—C9	−54.04 (8)	C16—C17—C18—C19	51.97 (9)
C6—C5—C8—C20	−109.80 (7)	C17—C18—C19—O2	127.53 (8)
C4—C5—C8—C20	67.91 (8)	C17—C18—C19—C20	−52.57 (9)
C5—C8—C9—C14	122.43 (7)	O4—C15—C20—C19	67.95 (7)
C20—C8—C9—C14	1.21 (9)	O5—C15—C20—C19	−174.06 (5)
C5—C8—C9—C10	−64.17 (8)	C16—C15—C20—C19	−56.44 (7)
C20—C8—C9—C10	174.62 (6)	O4—C15—C20—C8	−58.05 (7)
C14—C9—C10—O3	169.77 (7)	O5—C15—C20—C8	59.94 (7)
C8—C9—C10—O3	−3.90 (10)	C16—C15—C20—C8	177.56 (6)
C14—C9—C10—C11	−6.00 (9)	O2—C19—C20—C15	−125.90 (8)
C8—C9—C10—C11	−179.66 (6)	C18—C19—C20—C15	54.19 (8)
O3—C10—C11—C12	155.40 (7)	O2—C19—C20—C8	−0.58 (10)
C9—C10—C11—C12	−28.78 (9)	C18—C19—C20—C8	179.51 (6)
C10—C11—C12—C13	55.12 (8)	C9—C8—C20—C15	−34.60 (7)
C11—C12—C13—C14	−47.83 (8)	C5—C8—C20—C15	−157.37 (5)
C15—O5—C14—C9	18.89 (9)	C9—C8—C20—C19	−158.31 (6)
C15—O5—C14—C13	−160.19 (6)	C5—C8—C20—C19	78.92 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3i	0.886 (17)	1.935 (17)	2.8156 (8)	172.0 (16)
C12—H12B···O4ii	0.99	2.50	3.1879 (9)	126
C12—H12A···Cg1iii	0.99	2.78	3.6557 (8)	147
C16—H16A···Cg1iv	0.99	2.78	3.7467 (8)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3i	0.886 (17)	1.935 (17)	2.8156 (8)	172.0 (16)
C12—H12B⋯O4ii	0.99	2.50	3.1879 (9)	126
C12—H12A⋯Cg1iii	0.99	2.78	3.6557 (8)	147
C16—H16A⋯Cg1iv	0.99	2.78	3.7467 (8)	165

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