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

In the title compound, C(20)H(22)O(5), an S(6) ring motif is formed by an intra-molecular C-H⋯O hydrogen bond, which contributes to the stabilization of the mol-ecule. In the xanthene system, the cyclo-hexane ring adopts a chair conformation, the cyclo-hexene ring adopts a half-boat conformation and the tetra-hydro-pyran ring adopts a half-chair conformation. The mean plane of the four essentially planar atoms of the tetra-hydro-pyran ring [r.m.s deviation = 0.092 (1) Å] forms a dihedral angle of 64.13 (6)° with the mean plane of the meth-oxy-phenyl group. In the crystal, inter-molecular O-H⋯O and weak C-H⋯O hydrogen bonds link mol-ecules into chains along the a axis, which are further stabilized by C-H⋯π inter-actions.

Related literature

For background to and the biological activity of xanthenes and their derivatives, see: Menchen et al. (2003 ▶); Saint-Ruf et al. (1972 ▶); Ion et al. (1998 ▶); Knight & Stephens (1989 ▶); Jonathan et al. (1988 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Reddy et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H22O5

M = 342.38

Triclinic,

a = 7.1060 (1) Å

b = 7.8897 (1) Å

c = 15.1001 (2) Å

α = 91.285 (1)°

β = 101.251 (1)°

γ = 101.129 (1)°

V = 813.10 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.44 × 0.23 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.957, T max = 0.990

21213 measured reflections

4715 independent reflections

4132 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.05

4715 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.25 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 datablocks global, I. DOI: 10.1107/S1600536810050191/lh5179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050191/lh5179Isup2.hkl

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

C20H22O5	Z = 2
Mr = 342.38	F(000) = 364
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1060 (1) Å	Cell parameters from 9956 reflections
b = 7.8897 (1) Å	θ = 2.6–37.2°
c = 15.1001 (2) Å	µ = 0.10 mm−1
α = 91.285 (1)°	T = 100 K
β = 101.251 (1)°	Block, colourless
γ = 101.129 (1)°	0.44 × 0.23 × 0.10 mm
V = 813.10 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4715 independent reflections
Radiation source: fine-focus sealed tube	4132 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.957, Tmax = 0.990	k = −11→11
21213 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.057P)2 + 0.3385P] where P = (Fo2 + 2Fc2)/3
4715 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.25 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 100.0 (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	0.99328 (11)	0.05712 (9)	0.14023 (5)	0.01184 (15)
O2	0.70333 (12)	0.35590 (10)	0.19525 (6)	0.01849 (17)
O3	0.34225 (11)	−0.15228 (10)	0.17249 (5)	0.01475 (16)
O4	0.74431 (12)	0.15152 (9)	0.43898 (5)	0.01407 (16)
O5	1.11520 (11)	−0.03057 (9)	0.28104 (5)	0.01311 (15)
C1	1.06767 (15)	0.11229 (12)	0.23546 (6)	0.01072 (18)
C2	1.24660 (15)	0.25412 (13)	0.23649 (7)	0.01350 (19)
H2A	1.3340	0.2104	0.2039	0.016*
H2B	1.3158	0.2835	0.2986	0.016*
C3	1.19583 (16)	0.41749 (13)	0.19413 (7)	0.0163 (2)
H3A	1.1438	0.3927	0.1298	0.020*
H3B	1.3137	0.5066	0.2015	0.020*
C4	1.04414 (17)	0.48393 (13)	0.23831 (8)	0.0172 (2)
H4A	1.1005	0.5208	0.3012	0.021*
H4B	1.0064	0.5825	0.2075	0.021*
C5	0.86650 (16)	0.34065 (13)	0.23232 (7)	0.01310 (19)
C6	0.90683 (15)	0.17311 (12)	0.27485 (6)	0.01074 (18)
H6A	0.9570	0.2001	0.3398	0.013*
C7	0.71877 (15)	0.03250 (12)	0.26338 (6)	0.01037 (18)
H7A	0.6112	0.0933	0.2644	0.012*
C8	0.67731 (15)	−0.05984 (12)	0.17062 (6)	0.01066 (18)
C9	0.47820 (15)	−0.15295 (12)	0.13264 (6)	0.01103 (18)
C10	0.43704 (15)	−0.24679 (13)	0.04013 (7)	0.01356 (19)
H10A	0.3871	−0.1725	−0.0052	0.016*
H10B	0.3363	−0.3499	0.0383	0.016*
C11	0.61838 (16)	−0.29864 (13)	0.01678 (7)	0.01432 (19)
H11A	0.6579	−0.3863	0.0563	0.017*
H11B	0.5882	−0.3473	−0.0451	0.017*
C12	0.78507 (16)	−0.14125 (13)	0.02780 (7)	0.01329 (19)
H12A	0.9051	−0.1781	0.0224	0.016*
H12B	0.7561	−0.0643	−0.0200	0.016*
C13	0.81329 (15)	−0.04614 (12)	0.11791 (6)	0.01064 (18)
C14	0.71718 (14)	−0.09100 (12)	0.33983 (6)	0.01062 (18)
C15	0.72872 (15)	−0.02412 (12)	0.42848 (7)	0.01140 (18)
C16	0.72200 (16)	−0.13289 (13)	0.49996 (7)	0.01399 (19)
H16A	0.7337	−0.0869	0.5585	0.017*
C17	0.69757 (16)	−0.31127 (13)	0.48290 (7)	0.0150 (2)
H17A	0.6903	−0.3844	0.5301	0.018*
C18	0.68398 (16)	−0.38035 (13)	0.39597 (7)	0.0146 (2)
H18A	0.6674	−0.4992	0.3847	0.018*
C19	0.69553 (15)	−0.26938 (13)	0.32551 (7)	0.01285 (19)
H19A	0.6886	−0.3158	0.2675	0.015*
C20	0.79471 (17)	0.22709 (13)	0.52994 (7)	0.0154 (2)
H20A	0.8251	0.3509	0.5289	0.023*
H20B	0.9066	0.1875	0.5625	0.023*
H20C	0.6861	0.1934	0.5593	0.023*
H1O5	1.201 (3)	−0.067 (2)	0.2552 (12)	0.027 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0112 (3)	0.0143 (3)	0.0096 (3)	−0.0001 (3)	0.0038 (3)	−0.0002 (2)
O2	0.0168 (4)	0.0169 (4)	0.0226 (4)	0.0053 (3)	0.0039 (3)	0.0048 (3)
O3	0.0130 (4)	0.0158 (3)	0.0160 (3)	0.0021 (3)	0.0054 (3)	−0.0011 (3)
O4	0.0207 (4)	0.0119 (3)	0.0100 (3)	0.0039 (3)	0.0036 (3)	−0.0005 (2)
O5	0.0144 (4)	0.0141 (3)	0.0132 (3)	0.0058 (3)	0.0053 (3)	0.0034 (3)
C1	0.0112 (4)	0.0117 (4)	0.0091 (4)	0.0014 (3)	0.0027 (3)	0.0007 (3)
C2	0.0111 (4)	0.0148 (4)	0.0141 (4)	−0.0001 (4)	0.0041 (3)	0.0004 (3)
C3	0.0160 (5)	0.0134 (4)	0.0194 (5)	−0.0004 (4)	0.0065 (4)	0.0020 (3)
C4	0.0175 (5)	0.0116 (4)	0.0229 (5)	0.0006 (4)	0.0076 (4)	0.0002 (4)
C5	0.0158 (5)	0.0115 (4)	0.0129 (4)	0.0022 (4)	0.0058 (4)	0.0000 (3)
C6	0.0114 (4)	0.0110 (4)	0.0098 (4)	0.0015 (3)	0.0030 (3)	0.0000 (3)
C7	0.0110 (4)	0.0109 (4)	0.0093 (4)	0.0018 (3)	0.0026 (3)	0.0003 (3)
C8	0.0119 (4)	0.0099 (4)	0.0099 (4)	0.0019 (3)	0.0021 (3)	0.0003 (3)
C9	0.0125 (4)	0.0097 (4)	0.0112 (4)	0.0026 (3)	0.0029 (3)	0.0014 (3)
C10	0.0132 (5)	0.0143 (4)	0.0122 (4)	0.0009 (4)	0.0025 (4)	−0.0024 (3)
C11	0.0161 (5)	0.0126 (4)	0.0140 (4)	0.0012 (4)	0.0044 (4)	−0.0025 (3)
C12	0.0156 (5)	0.0137 (4)	0.0108 (4)	0.0014 (4)	0.0052 (4)	−0.0016 (3)
C13	0.0119 (4)	0.0098 (4)	0.0099 (4)	0.0016 (3)	0.0021 (3)	0.0010 (3)
C14	0.0098 (4)	0.0121 (4)	0.0100 (4)	0.0017 (3)	0.0027 (3)	0.0014 (3)
C15	0.0106 (4)	0.0121 (4)	0.0118 (4)	0.0021 (3)	0.0032 (3)	0.0004 (3)
C16	0.0155 (5)	0.0157 (4)	0.0109 (4)	0.0028 (4)	0.0035 (4)	0.0014 (3)
C17	0.0162 (5)	0.0153 (4)	0.0139 (4)	0.0025 (4)	0.0039 (4)	0.0046 (3)
C18	0.0159 (5)	0.0119 (4)	0.0155 (4)	0.0020 (4)	0.0026 (4)	0.0017 (3)
C19	0.0130 (5)	0.0130 (4)	0.0122 (4)	0.0022 (4)	0.0022 (3)	−0.0003 (3)
C20	0.0189 (5)	0.0158 (4)	0.0112 (4)	0.0043 (4)	0.0020 (4)	−0.0025 (3)

O1—C13	1.3529 (12)	C8—C13	1.3574 (14)
O1—C1	1.4570 (11)	C8—C9	1.4607 (14)
O2—C5	1.2148 (13)	C9—C10	1.5151 (13)
O3—C9	1.2345 (12)	C10—C11	1.5253 (15)
O4—C15	1.3718 (12)	C10—H10A	0.9700
O4—C20	1.4350 (12)	C10—H10B	0.9700
O5—C1	1.3962 (11)	C11—C12	1.5227 (14)
O5—H1O5	0.874 (18)	C11—H11A	0.9700
C1—C2	1.5203 (14)	C11—H11B	0.9700
C1—C6	1.5345 (14)	C12—C13	1.4982 (13)
C2—C3	1.5255 (14)	C12—H12A	0.9700
C2—H2A	0.9700	C12—H12B	0.9700
C2—H2B	0.9700	C14—C19	1.3931 (13)
C3—C4	1.5378 (16)	C14—C15	1.4091 (13)
C3—H3A	0.9700	C15—C16	1.3964 (13)
C3—H3B	0.9700	C16—C17	1.3961 (14)
C4—C5	1.5098 (15)	C16—H16A	0.9300
C4—H4A	0.9700	C17—C18	1.3884 (14)
C4—H4B	0.9700	C17—H17A	0.9300
C5—C6	1.5344 (13)	C18—C19	1.3976 (14)
C6—C7	1.5412 (14)	C18—H18A	0.9300
C6—H6A	0.9800	C19—H19A	0.9300
C7—C8	1.5133 (13)	C20—H20A	0.9600
C7—C14	1.5276 (13)	C20—H20B	0.9600
C7—H7A	0.9800	C20—H20C	0.9600
C13—O1—C1	117.22 (7)	C8—C9—C10	118.74 (9)
C15—O4—C20	116.87 (8)	C9—C10—C11	112.70 (8)
C1—O5—H1O5	106.7 (11)	C9—C10—H10A	109.1
O5—C1—O1	107.99 (7)	C11—C10—H10A	109.1
O5—C1—C2	112.32 (8)	C9—C10—H10B	109.1
O1—C1—C2	104.81 (7)	C11—C10—H10B	109.1
O5—C1—C6	108.38 (8)	H10A—C10—H10B	107.8
O1—C1—C6	109.47 (8)	C12—C11—C10	110.02 (8)
C2—C1—C6	113.68 (8)	C12—C11—H11A	109.7
C1—C2—C3	113.12 (9)	C10—C11—H11A	109.7
C1—C2—H2A	109.0	C12—C11—H11B	109.7
C3—C2—H2A	109.0	C10—C11—H11B	109.7
C1—C2—H2B	109.0	H11A—C11—H11B	108.2
C3—C2—H2B	109.0	C13—C12—C11	110.92 (8)
H2A—C2—H2B	107.8	C13—C12—H12A	109.5
C2—C3—C4	111.06 (9)	C11—C12—H12A	109.5
C2—C3—H3A	109.4	C13—C12—H12B	109.5
C4—C3—H3A	109.4	C11—C12—H12B	109.5
C2—C3—H3B	109.4	H12A—C12—H12B	108.0
C4—C3—H3B	109.4	O1—C13—C8	123.96 (9)
H3A—C3—H3B	108.0	O1—C13—C12	111.00 (8)
C5—C4—C3	109.20 (8)	C8—C13—C12	125.03 (9)
C5—C4—H4A	109.8	C19—C14—C15	117.89 (9)
C3—C4—H4A	109.8	C19—C14—C7	122.94 (8)
C5—C4—H4B	109.8	C15—C14—C7	119.10 (8)
C3—C4—H4B	109.8	O4—C15—C16	123.04 (9)
H4A—C4—H4B	108.3	O4—C15—C14	115.90 (8)
O2—C5—C4	122.38 (9)	C16—C15—C14	121.05 (9)
O2—C5—C6	122.26 (9)	C17—C16—C15	119.48 (9)
C4—C5—C6	115.35 (9)	C17—C16—H16A	120.3
C5—C6—C1	109.28 (8)	C15—C16—H16A	120.3
C5—C6—C7	111.86 (8)	C18—C17—C16	120.50 (9)
C1—C6—C7	112.48 (8)	C18—C17—H17A	119.8
C5—C6—H6A	107.7	C16—C17—H17A	119.8
C1—C6—H6A	107.7	C17—C18—C19	119.31 (9)
C7—C6—H6A	107.7	C17—C18—H18A	120.3
C8—C7—C14	113.17 (8)	C19—C18—H18A	120.3
C8—C7—C6	109.55 (8)	C14—C19—C18	121.74 (9)
C14—C7—C6	114.28 (8)	C14—C19—H19A	119.1
C8—C7—H7A	106.4	C18—C19—H19A	119.1
C14—C7—H7A	106.4	O4—C20—H20A	109.5
C6—C7—H7A	106.4	O4—C20—H20B	109.5
C13—C8—C9	118.53 (9)	H20A—C20—H20B	109.5
C13—C8—C7	122.45 (9)	O4—C20—H20C	109.5
C9—C8—C7	118.73 (8)	H20A—C20—H20C	109.5
O3—C9—C8	121.80 (9)	H20B—C20—H20C	109.5
O3—C9—C10	119.41 (9)
C13—O1—C1—O5	71.99 (10)	C7—C8—C9—C10	−179.45 (8)
C13—O1—C1—C2	−168.09 (8)	O3—C9—C10—C11	−156.92 (9)
C13—O1—C1—C6	−45.81 (10)	C8—C9—C10—C11	25.45 (12)
O5—C1—C2—C3	−175.06 (8)	C9—C10—C11—C12	−53.49 (11)
O1—C1—C2—C3	67.95 (10)	C10—C11—C12—C13	50.03 (11)
C6—C1—C2—C3	−51.54 (11)	C1—O1—C13—C8	20.22 (13)
C1—C2—C3—C4	54.04 (11)	C1—O1—C13—C12	−160.09 (8)
C2—C3—C4—C5	−55.21 (12)	C9—C8—C13—O1	169.98 (8)
C3—C4—C5—O2	−122.06 (11)	C7—C8—C13—O1	−3.74 (15)
C3—C4—C5—C6	56.91 (11)	C9—C8—C13—C12	−9.66 (14)
O2—C5—C6—C1	125.76 (10)	C7—C8—C13—C12	176.62 (9)
C4—C5—C6—C1	−53.20 (11)	C11—C12—C13—O1	160.59 (8)
O2—C5—C6—C7	0.54 (13)	C11—C12—C13—C8	−19.73 (13)
C4—C5—C6—C7	−178.43 (8)	C8—C7—C14—C19	4.92 (14)
O5—C1—C6—C5	174.47 (8)	C6—C7—C14—C19	−121.40 (10)
O1—C1—C6—C5	−67.98 (10)	C8—C7—C14—C15	−171.98 (9)
C2—C1—C6—C5	48.83 (11)	C6—C7—C14—C15	61.70 (12)
O5—C1—C6—C7	−60.66 (10)	C20—O4—C15—C16	12.66 (14)
O1—C1—C6—C7	56.89 (10)	C20—O4—C15—C14	−168.10 (9)
C2—C1—C6—C7	173.70 (8)	C19—C14—C15—O4	−178.20 (9)
C5—C6—C7—C8	82.61 (9)	C7—C14—C15—O4	−1.14 (14)
C1—C6—C7—C8	−40.82 (10)	C19—C14—C15—C16	1.06 (15)
C5—C6—C7—C14	−149.21 (8)	C7—C14—C15—C16	178.12 (9)
C1—C6—C7—C14	87.36 (10)	O4—C15—C16—C17	177.27 (10)
C14—C7—C8—C13	−114.03 (10)	C14—C15—C16—C17	−1.94 (16)
C6—C7—C8—C13	14.77 (12)	C15—C16—C17—C18	1.30 (16)
C14—C7—C8—C9	72.27 (11)	C16—C17—C18—C19	0.17 (16)
C6—C7—C8—C9	−158.94 (8)	C15—C14—C19—C18	0.46 (15)
C13—C8—C9—O3	−170.97 (9)	C7—C14—C19—C18	−176.48 (9)
C7—C8—C9—O3	2.98 (14)	C17—C18—C19—C14	−1.07 (16)
C13—C8—C9—C10	6.60 (13)

Cg1 is the centroid of the C14–C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O3i	0.87 (2)	1.93 (2)	2.7877 (11)	166.3 (18)
C6—H6A···O4	0.98	2.32	2.9266 (12)	120
C16—H16A···O5ii	0.93	2.53	3.4172 (13)	160
C20—H20B···Cg1ii	0.96	2.67	3.5206 (13)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O3i	0.87 (2)	1.93 (2)	2.7877 (11)	166.3 (18)
C6—H6A⋯O4	0.98	2.32	2.9266 (12)	120
C16—H16A⋯O5ii	0.93	2.53	3.4172 (13)	160
C20—H20B⋯Cg1ii	0.96	2.67	3.5206 (13)	147

Symmetry codes: (i) ; (ii) .