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

In the title compound, C(24)H(28)O(5), the two cyclo-hexene rings adopt envelope conformations, and the planes through the coplanar atoms makes dihedral angles of 82.86 (6) and 77.90 (6)° with the benzene ring. The two cyclo-hexene rings make a dihedral angle of 5.33 (6)° between their least-squares planes. The pyran ring adopts a flattened boat conformation. In the crystal packing, mol-ecules are linked into two-dimensional networks parallel to the ab plane via O-H⋯O and C-H⋯O inter-actions.

Related literature

For the synthesis of the title compound, see: Venkatesan et al. (2008 ▶). For general background to and the biological activity of xanthene derivatives, see: Hafez et al. (2008 ▶); Ashry et al. (2006 ▶); Sill & Sweet (1977 ▶); Ion (1997 ▶); Chibale et al. (2003 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H28O5

M = 396.46

Orthorhombic,

a = 11.4861 (10) Å

b = 11.8659 (11) Å

c = 30.087 (3) Å

V = 4100.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.30 × 0.24 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.970, T max = 0.979

26584 measured reflections

5972 independent reflections

4634 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.06

5972 reflections

271 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.38 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/S1600536810020258/rz2454sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020258/rz2454Isup2.hkl

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

C24H28O5	F(000) = 1696
Mr = 396.46	Dx = 1.284 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5544 reflections
a = 11.4861 (10) Å	θ = 2.2–31.4°
b = 11.8659 (11) Å	µ = 0.09 mm−1
c = 30.087 (3) Å	T = 100 K
V = 4100.6 (6) Å3	Block, colourless
Z = 8	0.35 × 0.30 × 0.24 mm

Bruker APEXII DUO CCD area-detector diffractometer	5972 independent reflections
Radiation source: fine-focus sealed tube	4634 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→12
Tmin = 0.970, Tmax = 0.979	k = −16→16
26584 measured reflections	l = −20→42

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.8139P] where P = (Fo2 + 2Fc2)/3
5972 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−0.28861 (7)	0.40281 (8)	0.37337 (3)	0.01617 (19)
O2	0.01386 (8)	0.44676 (8)	0.26832 (3)	0.0228 (2)
O3	−0.01627 (8)	0.68315 (9)	0.41472 (4)	0.0257 (2)
O4	0.35090 (8)	0.35573 (8)	0.36534 (3)	0.0207 (2)
O5	0.27890 (8)	0.17322 (8)	0.41056 (4)	0.0225 (2)
C1	−0.23302 (10)	0.38185 (10)	0.33355 (4)	0.0146 (2)
C2	−0.30172 (10)	0.30335 (11)	0.30502 (4)	0.0170 (2)
H2A	−0.3616	0.3454	0.2895	0.020*
H2B	−0.3398	0.2477	0.3236	0.020*
C3	−0.22358 (11)	0.24318 (11)	0.27099 (4)	0.0190 (3)
C4	−0.15068 (12)	0.33410 (12)	0.24770 (5)	0.0215 (3)
H4A	−0.0983	0.2979	0.2268	0.026*
H4B	−0.2023	0.3826	0.2308	0.026*
C5	−0.08000 (11)	0.40592 (10)	0.27917 (4)	0.0171 (2)
C6	−0.12984 (10)	0.42841 (10)	0.32340 (4)	0.0142 (2)
C7	−0.05937 (10)	0.49443 (10)	0.35702 (4)	0.0142 (2)
H7A	−0.0228	0.5590	0.3423	0.017*
C8	−0.14118 (10)	0.53630 (10)	0.39271 (4)	0.0143 (2)
C9	−0.10776 (11)	0.63245 (11)	0.42079 (4)	0.0172 (2)
C10	−0.19236 (11)	0.67093 (11)	0.45628 (5)	0.0195 (3)
H10A	−0.2428	0.7283	0.4438	0.023*
H10B	−0.1487	0.7054	0.4803	0.023*
C11	−0.26798 (11)	0.57635 (11)	0.47544 (4)	0.0185 (3)
C12	−0.32808 (11)	0.51647 (11)	0.43638 (4)	0.0182 (3)
H12A	−0.3646	0.4479	0.4471	0.022*
H12B	−0.3888	0.5649	0.4247	0.022*
C13	−0.24524 (10)	0.48756 (10)	0.39991 (4)	0.0145 (2)
C14	0.03504 (10)	0.41644 (10)	0.37528 (4)	0.0144 (2)
C15	0.15186 (10)	0.43068 (10)	0.36324 (4)	0.0150 (2)
H15A	0.1742	0.4937	0.3470	0.018*
C16	0.23459 (10)	0.35118 (11)	0.37548 (4)	0.0154 (2)
C17	0.20159 (11)	0.25532 (10)	0.39955 (4)	0.0163 (2)
C18	0.08671 (11)	0.24362 (11)	0.41294 (5)	0.0192 (3)
H18A	0.0648	0.1820	0.4301	0.023*
C19	0.00419 (11)	0.32338 (11)	0.40088 (5)	0.0186 (3)
H19A	−0.0726	0.3146	0.4100	0.022*
C20	−0.14395 (12)	0.15751 (11)	0.29401 (5)	0.0253 (3)
H20A	−0.1906	0.1025	0.3092	0.038*
H20B	−0.0951	0.1957	0.3151	0.038*
H20C	−0.0963	0.1207	0.2722	0.038*
C21	−0.29993 (13)	0.18345 (13)	0.23661 (5)	0.0291 (3)
H21A	−0.3498	0.1304	0.2514	0.044*
H21B	−0.2513	0.1444	0.2157	0.044*
H21C	−0.3465	0.2381	0.2212	0.044*
C22	−0.36133 (12)	0.62585 (14)	0.50611 (5)	0.0282 (3)
H22A	−0.3246	0.6625	0.5308	0.042*
H22B	−0.4107	0.5664	0.5168	0.042*
H22C	−0.4072	0.6796	0.4899	0.042*
C23	−0.19191 (13)	0.49357 (13)	0.50166 (5)	0.0280 (3)
H23A	−0.1551	0.5324	0.5259	0.042*
H23B	−0.1334	0.4626	0.4824	0.042*
H23C	−0.2396	0.4338	0.5131	0.042*
C24	0.39966 (11)	0.46439 (12)	0.35714 (5)	0.0238 (3)
H24A	0.4831	0.4594	0.3577	0.036*
H24B	0.3739	0.5160	0.3797	0.036*
H24C	0.3748	0.4908	0.3285	0.036*
H14O	0.3488 (19)	0.1956 (19)	0.4055 (8)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0129 (4)	0.0191 (4)	0.0165 (4)	−0.0030 (3)	0.0024 (3)	−0.0032 (3)
O2	0.0224 (5)	0.0237 (5)	0.0223 (5)	−0.0030 (4)	0.0075 (4)	0.0022 (4)
O3	0.0185 (5)	0.0247 (5)	0.0339 (6)	−0.0067 (4)	0.0031 (4)	−0.0047 (4)
O4	0.0105 (4)	0.0246 (5)	0.0272 (5)	0.0030 (3)	0.0023 (3)	0.0053 (4)
O5	0.0165 (5)	0.0195 (5)	0.0315 (5)	0.0044 (4)	−0.0038 (4)	0.0044 (4)
C1	0.0140 (5)	0.0146 (5)	0.0152 (5)	0.0022 (4)	0.0005 (4)	0.0006 (4)
C2	0.0153 (5)	0.0179 (5)	0.0179 (6)	−0.0010 (4)	−0.0009 (4)	−0.0017 (5)
C3	0.0214 (6)	0.0169 (6)	0.0187 (6)	−0.0027 (5)	0.0022 (5)	−0.0026 (5)
C4	0.0263 (7)	0.0216 (6)	0.0166 (6)	−0.0029 (5)	0.0036 (5)	−0.0008 (5)
C5	0.0205 (6)	0.0143 (5)	0.0166 (6)	0.0021 (4)	0.0024 (5)	0.0028 (5)
C6	0.0132 (5)	0.0135 (5)	0.0159 (5)	0.0021 (4)	0.0003 (4)	0.0024 (4)
C7	0.0106 (5)	0.0146 (5)	0.0173 (6)	0.0004 (4)	0.0012 (4)	0.0017 (4)
C8	0.0114 (5)	0.0148 (5)	0.0166 (5)	0.0015 (4)	−0.0001 (4)	0.0015 (4)
C9	0.0144 (5)	0.0166 (5)	0.0206 (6)	0.0004 (4)	−0.0021 (5)	0.0007 (5)
C10	0.0165 (6)	0.0202 (6)	0.0219 (6)	−0.0002 (5)	−0.0008 (5)	−0.0049 (5)
C11	0.0155 (5)	0.0237 (6)	0.0163 (6)	−0.0008 (5)	0.0010 (5)	−0.0023 (5)
C12	0.0127 (5)	0.0229 (6)	0.0191 (6)	−0.0005 (4)	0.0017 (4)	−0.0036 (5)
C13	0.0119 (5)	0.0161 (5)	0.0156 (5)	0.0006 (4)	−0.0011 (4)	−0.0001 (5)
C14	0.0116 (5)	0.0152 (5)	0.0164 (5)	0.0014 (4)	−0.0005 (4)	−0.0004 (4)
C15	0.0129 (5)	0.0156 (5)	0.0164 (5)	−0.0004 (4)	0.0002 (4)	0.0008 (4)
C16	0.0112 (5)	0.0199 (6)	0.0151 (5)	0.0013 (4)	−0.0007 (4)	−0.0016 (5)
C17	0.0141 (5)	0.0177 (6)	0.0171 (6)	0.0026 (4)	−0.0031 (4)	−0.0001 (5)
C18	0.0169 (6)	0.0173 (6)	0.0235 (6)	−0.0005 (4)	−0.0003 (5)	0.0043 (5)
C19	0.0130 (5)	0.0193 (6)	0.0235 (6)	−0.0002 (4)	0.0016 (5)	0.0028 (5)
C20	0.0260 (7)	0.0145 (6)	0.0354 (8)	0.0013 (5)	0.0065 (6)	0.0001 (6)
C21	0.0334 (8)	0.0288 (7)	0.0252 (7)	−0.0090 (6)	0.0034 (6)	−0.0102 (6)
C22	0.0221 (7)	0.0409 (8)	0.0216 (7)	−0.0028 (6)	0.0033 (5)	−0.0115 (6)
C23	0.0301 (7)	0.0339 (8)	0.0200 (7)	0.0016 (6)	−0.0021 (6)	0.0045 (6)
C24	0.0143 (6)	0.0272 (7)	0.0298 (7)	−0.0045 (5)	0.0002 (5)	−0.0047 (6)

O1—C13	1.3772 (15)	C11—C22	1.5317 (18)
O1—C1	1.3802 (14)	C11—C23	1.5333 (19)
O2—C5	1.2263 (15)	C11—C12	1.5370 (18)
O3—C9	1.2246 (15)	C12—C13	1.4922 (17)
O4—C16	1.3714 (15)	C12—H12A	0.9700
O4—C24	1.4272 (17)	C12—H12B	0.9700
O5—C17	1.3591 (15)	C14—C19	1.3922 (18)
O5—H14O	0.86 (2)	C14—C15	1.4001 (16)
C1—C6	1.3427 (17)	C15—C16	1.3886 (17)
C1—C2	1.4924 (17)	C15—H15A	0.9300
C2—C3	1.5372 (18)	C16—C17	1.4007 (18)
C2—H2A	0.9700	C17—C18	1.3867 (18)
C2—H2B	0.9700	C18—C19	1.3877 (18)
C3—C21	1.5301 (19)	C18—H18A	0.9300
C3—C20	1.5329 (19)	C19—H19A	0.9300
C3—C4	1.5350 (18)	C20—H20A	0.9600
C4—C5	1.5106 (19)	C20—H20B	0.9600
C4—H4A	0.9700	C20—H20C	0.9600
C4—H4B	0.9700	C21—H21A	0.9600
C5—C6	1.4730 (17)	C21—H21B	0.9600
C6—C7	1.5140 (17)	C21—H21C	0.9600
C7—C8	1.5108 (17)	C22—H22A	0.9600
C7—C14	1.5278 (16)	C22—H22B	0.9600
C7—H7A	0.9800	C22—H22C	0.9600
C8—C13	1.3454 (16)	C23—H23A	0.9600
C8—C9	1.4706 (17)	C23—H23B	0.9600
C9—C10	1.5143 (18)	C23—H23C	0.9600
C10—C11	1.5317 (18)	C24—H24A	0.9600
C10—H10A	0.9700	C24—H24B	0.9600
C10—H10B	0.9700	C24—H24C	0.9600
C13—O1—C1	117.88 (9)	C11—C12—H12A	109.1
C16—O4—C24	117.15 (10)	C13—C12—H12B	109.1
C17—O5—H14O	110.3 (15)	C11—C12—H12B	109.1
C6—C1—O1	122.11 (11)	H12A—C12—H12B	107.8
C6—C1—C2	126.34 (11)	C8—C13—O1	122.80 (11)
O1—C1—C2	111.55 (10)	C8—C13—C12	125.88 (11)
C1—C2—C3	111.36 (10)	O1—C13—C12	111.32 (10)
C1—C2—H2A	109.4	C19—C14—C15	118.86 (11)
C3—C2—H2A	109.4	C19—C14—C7	119.92 (10)
C1—C2—H2B	109.4	C15—C14—C7	120.94 (11)
C3—C2—H2B	109.4	C16—C15—C14	120.35 (12)
H2A—C2—H2B	108.0	C16—C15—H15A	119.8
C21—C3—C20	109.88 (12)	C14—C15—H15A	119.8
C21—C3—C4	109.24 (11)	O4—C16—C15	125.52 (12)
C20—C3—C4	110.30 (11)	O4—C16—C17	114.24 (11)
C21—C3—C2	109.31 (11)	C15—C16—C17	120.23 (11)
C20—C3—C2	110.83 (11)	O5—C17—C18	118.62 (12)
C4—C3—C2	107.22 (10)	O5—C17—C16	122.09 (11)
C5—C4—C3	113.79 (11)	C18—C17—C16	119.28 (11)
C5—C4—H4A	108.8	C17—C18—C19	120.37 (12)
C3—C4—H4A	108.8	C17—C18—H18A	119.8
C5—C4—H4B	108.8	C19—C18—H18A	119.8
C3—C4—H4B	108.8	C18—C19—C14	120.78 (12)
H4A—C4—H4B	107.7	C18—C19—H19A	119.6
O2—C5—C6	120.71 (12)	C14—C19—H19A	119.6
O2—C5—C4	121.91 (12)	C3—C20—H20A	109.5
C6—C5—C4	117.36 (11)	C3—C20—H20B	109.5
C1—C6—C5	118.29 (11)	H20A—C20—H20B	109.5
C1—C6—C7	122.20 (11)	C3—C20—H20C	109.5
C5—C6—C7	119.31 (10)	H20A—C20—H20C	109.5
C8—C7—C6	108.21 (10)	H20B—C20—H20C	109.5
C8—C7—C14	112.65 (10)	C3—C21—H21A	109.5
C6—C7—C14	107.84 (10)	C3—C21—H21B	109.5
C8—C7—H7A	109.4	H21A—C21—H21B	109.5
C6—C7—H7A	109.4	C3—C21—H21C	109.5
C14—C7—H7A	109.4	H21A—C21—H21C	109.5
C13—C8—C9	118.22 (11)	H21B—C21—H21C	109.5
C13—C8—C7	121.72 (11)	C11—C22—H22A	109.5
C9—C8—C7	120.07 (10)	C11—C22—H22B	109.5
O3—C9—C8	121.30 (12)	H22A—C22—H22B	109.5
O3—C9—C10	120.51 (12)	C11—C22—H22C	109.5
C8—C9—C10	118.14 (11)	H22A—C22—H22C	109.5
C9—C10—C11	114.09 (11)	H22B—C22—H22C	109.5
C9—C10—H10A	108.7	C11—C23—H23A	109.5
C11—C10—H10A	108.7	C11—C23—H23B	109.5
C9—C10—H10B	108.7	H23A—C23—H23B	109.5
C11—C10—H10B	108.7	C11—C23—H23C	109.5
H10A—C10—H10B	107.6	H23A—C23—H23C	109.5
C22—C11—C10	110.04 (11)	H23B—C23—H23C	109.5
C22—C11—C23	109.54 (12)	O4—C24—H24A	109.5
C10—C11—C23	109.87 (11)	O4—C24—H24B	109.5
C22—C11—C12	108.88 (10)	H24A—C24—H24B	109.5
C10—C11—C12	107.80 (11)	O4—C24—H24C	109.5
C23—C11—C12	110.68 (11)	H24A—C24—H24C	109.5
C13—C12—C11	112.46 (10)	H24B—C24—H24C	109.5
C13—C12—H12A	109.1
C13—O1—C1—C6	10.47 (17)	C9—C10—C11—C22	−172.25 (11)
C13—O1—C1—C2	−169.61 (10)	C9—C10—C11—C23	67.06 (14)
C6—C1—C2—C3	22.80 (18)	C9—C10—C11—C12	−53.64 (14)
O1—C1—C2—C3	−157.11 (10)	C22—C11—C12—C13	167.54 (12)
C1—C2—C3—C21	−168.27 (11)	C10—C11—C12—C13	48.19 (14)
C1—C2—C3—C20	70.47 (13)	C23—C11—C12—C13	−71.99 (14)
C1—C2—C3—C4	−49.96 (14)	C9—C8—C13—O1	174.91 (11)
C21—C3—C4—C5	174.64 (12)	C7—C8—C13—O1	−5.31 (18)
C20—C3—C4—C5	−64.49 (15)	C9—C8—C13—C12	−4.82 (19)
C2—C3—C4—C5	56.29 (14)	C7—C8—C13—C12	174.95 (12)
C3—C4—C5—O2	148.98 (12)	C1—O1—C13—C8	−12.05 (17)
C3—C4—C5—C6	−32.87 (16)	C1—O1—C13—C12	167.72 (10)
O1—C1—C6—C5	−176.84 (10)	C11—C12—C13—C8	−21.12 (18)
C2—C1—C6—C5	3.25 (18)	C11—C12—C13—O1	159.11 (10)
O1—C1—C6—C7	8.37 (18)	C8—C7—C14—C19	52.88 (15)
C2—C1—C6—C7	−171.54 (11)	C6—C7—C14—C19	−66.46 (15)
O2—C5—C6—C1	179.82 (11)	C8—C7—C14—C15	−133.24 (12)
C4—C5—C6—C1	1.65 (17)	C6—C7—C14—C15	107.43 (13)
O2—C5—C6—C7	−5.23 (17)	C19—C14—C15—C16	2.08 (19)
C4—C5—C6—C7	176.59 (11)	C7—C14—C15—C16	−171.87 (11)
C1—C6—C7—C8	−22.67 (15)	C24—O4—C16—C15	25.08 (18)
C5—C6—C7—C8	162.59 (10)	C24—O4—C16—C17	−156.10 (12)
C1—C6—C7—C14	99.45 (13)	C14—C15—C16—O4	179.50 (12)
C5—C6—C7—C14	−75.29 (13)	C14—C15—C16—C17	0.74 (19)
C6—C7—C8—C13	21.08 (15)	O4—C16—C17—O5	−1.71 (18)
C14—C7—C8—C13	−98.04 (13)	C15—C16—C17—O5	177.18 (12)
C6—C7—C8—C9	−159.15 (11)	O4—C16—C17—C18	177.85 (12)
C14—C7—C8—C9	81.73 (14)	C15—C16—C17—C18	−3.26 (19)
C13—C8—C9—O3	−177.09 (12)	O5—C17—C18—C19	−177.48 (12)
C7—C8—C9—O3	3.13 (18)	C16—C17—C18—C19	3.0 (2)
C13—C8—C9—C10	0.12 (17)	C17—C18—C19—C14	−0.1 (2)
C7—C8—C9—C10	−179.65 (11)	C15—C14—C19—C18	−2.4 (2)
O3—C9—C10—C11	−152.16 (12)	C7—C14—C19—C18	171.61 (12)
C8—C9—C10—C11	30.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H14O···O3i	0.86 (2)	1.95 (2)	2.7319 (13)	151 (2)
C2—H2A···O2ii	0.97	2.55	3.5003 (16)	165
C20—H20C···O2iii	0.96	2.58	3.4646 (17)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H14O⋯O3i	0.86 (2)	1.95 (2)	2.7319 (13)	151 (2)
C2—H2A⋯O2ii	0.97	2.55	3.5003 (16)	165
C20—H20C⋯O2iii	0.96	2.58	3.4646 (17)	154

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