12-Acetyl-6-hy­droxy-3,3,9,9-tetra­methyl­furo[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione

Ee, G.C.L.; Teo, S.H.; Kwong, H.C.; Mohamed Tahir, M.I.; Silong, S.

doi:10.1107/S1600536810048592

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3331-o3332

https://doi.org/10.1107/S1600536810048592

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12-Acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione

Gwendoline Cheng Lian Ee,^a ^* Siow Hwa Teo,^a Huey Chong Kwong,^a Mohamed Ibrahim Mohamed Tahir ^a and Sidik Silong ^a

^aDepartment of Chemistry, Faculty of Science, University Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
^*Correspondence e-mail: gwen@science.upm.edu.my

(Received 6 October 2010; accepted 22 November 2010; online 27 November 2010)

The title compound, Artonol B, C₂₄H₂₀O₇, isolated from the stem bark of Artocarpus kemando, consists of four six-membered rings and one five-membered ring. The tricyclic xanthone ring system is almost planar [maximum deviation 0.115 (5) Å], whereas the pyranoid ring is in a distorted boat conformation·The furan ring is almost coplanar with the fused aromatic ring, making a dihedral angle of 3.76 (9)°. The phenol ring serves as a intramolecular hydrogen-bond donor to the adjacent carbonyl group and also acts as an intermolecular hydrogen-bond acceptor for the methyl groups of adjacent molecules, forming a three-dimensional network in the crystal.

Related literature

For bond-length data, see Allen et al. (1987 ). For related structures, see: Doriguetto et al. (2001 ); Marek et al. (2003 ); Boonnak et al. (2007 ). For the biological activity of flavonoids from Artocarpus kemando and other species of Artocarpus, see: Burkill (1935 ); Makmur et al. (1999 ); Wei et al. (2005 ); Toshio et al. (2003 ); Lin et al. (1996 ); Shimizu et al. (2000 ); Patil et al. (2002 ); Tati et al. (2001 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₂₄H₂₀O₇
M_r = 420.42
Monoclinic, C 2/c
a = 36.511 (2) Å
b = 5.3275 (2) Å
c = 20.0218 (8) Å
β = 96.318 (5)°
V = 3870.8 (3) Å³
Z = 8
Cu Kα radiation
μ = 0.89 mm⁻¹
T = 150 K
0.30 × 0.28 × 0.04 mm

Data collection

Oxford Diffraction Gemini E diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.780, T_max = 0.965
17338 measured reflections
3813 independent reflections
3383 reflections with I > 2.0σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 0.99
3813 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H161⋯O15ⁱ	0.96	2.55	3.4062 (19)	148
C20—H202⋯O13ⁱ	0.97	2.53	3.4918 (19)	171
O22—H221⋯O5	0.88	1.78	2.5922 (19)	153
C31—H313⋯O22ⁱⁱ	0.97	2.57	3.5170 (19)	165
C27—H271⋯O5ⁱⁱⁱ	0.94	2.58	3.4923 (19)	163
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048592/kp2279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048592/kp2279Isup2.hkl

checkCIF report

Comment top

Flavonoids are polyphenolic compounds which are important for human health. Previous studies on flavonoids from this plant and other species of Artocarpus have revealed their wide range of pharmacological activities (Wei, et al., 2005; Toshio, et al., 2003; Lin et al., 1996; Shimizu et al., 2000; Patil et al., 2002; Tati et al., 2001). Artocarpus kemando, a tree of the forests and swamps is distributed in Thailand, Peninsular Malaysia, Sumatra and Borneo island (Burkill, 1935). In our continuing search for anti-cancer hit compounds we decided to look at Artocarpus kemando. We found that the chloroform extract of the stem bark of Artocarpus kemando displayed significant growth inhibition activities towards HL-60 cell lines and obtained Artonol B (I).

The molecular structure of (I) (Fig. 1) with the xanthone skeleton (ring B, C and D) is nearly planar with the exception of the atom C8 with the deviation from planarity of 0.115 Å. Rings A, B, C and D are individually almost planar, including the O5, O15 abd O22 atoms that are linked to them. The largest deviations from the individiual least-squares planes are 0.030 Å, 0.023 Å, 0.037 Å and 0.019 Å for ring A, B, C and D, respectively. Rings A and B form a dihedral angle of 3.06°, those of B and C ring form an angle of 4.23° and rings C and D form an dihedral angle of 3.42°. The planes of rings B and D intersect on a line which is approximately through the middle of ring C and gives rise to a dihedral angle of 7.65°. The mean torsion angle of ring D is 16.26° and it adopts a conformation half way between an envolope and a half-boat. The major pucking is in ring D at C28, owing to the constraint of the double bond between C26 and C27.

Bond distances and angles in the titled compound are in normal range (Allen et al., 1987). The average value of C—O1 bond lengths in pyranoid ring C is 1.368 Å and the observed geometries of pyranoid ring C are comparable to other reported pyranoxanthone geometries (Doriguetto et al., 2001; Marek et al.,2003; Boonnak et al., 2007). The crystal structure is stabilised by intra- and intermolecular O—H···O and C—H···O hydrogen bonding. The titled molecules exhibit a moderate intramolecular hydrogen bond O22—H221···O5, with O···O = 2.5922 (19) Å. Meanwhile, the H atom of the C31 methyl group forms a hydrogen bond with O22 at (-x, -y + 2, -z) [the C···O distance is 3.5170 (19) Å]. The H atom at C27 forms a hydrogen bond with O5 at (x, -y + 1, z - 1/2)[the C···O distance is 3.4923 (19) Å](Table 1).

The cystallographic data of this crystal structure has been deposited at Cambridge Crystallographic Data Center with deposition number CCDC 796169 (Allen, 2002).

Related literature top

For bond-length data, see Allen et al. (1987). For related structures, see: Doriguetto et al. (2001); Marek et al. (2003); Boonnak et al. (2007). For the biological activity of flavonoids from Artocarpus kemando and other species of Artocarpus, see: Burkill (1935); Makmur et al. (1999); Wei et al. (2005); Toshio et al. (2003); Lin et al. (1996); Shimizu et al. (2000); Patil et al. (2002); Tati et al. (2001).

For related literature, see: Allen (2002).

Experimental top

The powdered stem bark (4.7 kg) of Artocarpus kemando were defatted with n-hexane and sequentially extracted using methanol at room temperature for more than 48 h. This resulted in 198.5 g of methanol extract. The methanol extract was dissolved in a water-acetone mixture (1: 3, 500 mL) and the soluble portion was partitioned using chloroform (CHCl₃) (3 × 400 mL) to afford a crude chloroform extract (20 g). Repeated silica gel column chromatographic separation on the chloroform extract (20 g) (hexane, hexane-chloroform, chloroform-ethyl acetate, ethyl acetate-methanol and methanol in order of increasing polarity) followed by radial chromatography yielded pure artonol B (I), fine yellow solid with melting point 462-467 K. Good single crystals for X-ray diffraction were prepared by slow evaporation and diffusion of diethyl ether into a solution of (I) in chloroform at room temperature.

Structure description top

The cystallographic data of this crystal structure has been deposited at Cambridge Crystallographic Data Center with deposition number CCDC 796169 (Allen, 2002).

For bond-length data, see Allen et al. (1987). For related structures, see: Doriguetto et al. (2001); Marek et al. (2003); Boonnak et al. (2007). For the biological activity of flavonoids from Artocarpus kemando and other species of Artocarpus, see: Burkill (1935); Makmur et al. (1999); Wei et al. (2005); Toshio et al. (2003); Lin et al. (1996); Shimizu et al. (2000); Patil et al. (2002); Tati et al. (2001).

For related literature, see: Allen (2002).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

Fig. 1. Structure and the labeling scheme for 12-acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione. Displacement ellipsoids are drawn at the 50% probability level.

12-Acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2- h]xanthene-7,11(3H,9H)-dione top

Crystal data top

C₂₄H₂₀O₇	F(000) = 1760
M_r = 420.42	D_x = 1.443 Mg m⁻³
Monoclinic, C2/c	Melting point: 189 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54184 Å
a = 36.511 (2) Å	Cell parameters from 8995 reflections
b = 5.3275 (2) Å	θ = 72.0–3.5°
c = 20.0218 (8) Å	µ = 0.89 mm⁻¹
β = 96.318 (5)°	T = 150 K
V = 3870.8 (3) Å³	Plate, yellow
Z = 8	0.30 × 0.28 × 0.04 mm

Data collection top

Oxford Diffraction Gemini E diffractometer	3813 independent reflections
Radiation source: sealed x-ray tube	3383 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.018
ω/2θ scans	θ_max = 72.1°, θ_min = 4.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −44→41
T_min = 0.780, T_max = 0.965	k = −6→6
17338 measured reflections	l = −15→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F²) + (0.07P)² + 3.68P], where P = [max(F_o²,0) + 2F_c²]/3
S = 0.99	(Δ/σ)_max = 0.0002873
3813 reflections	Δρ_max = 0.32 e Å⁻³
280 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Crystal data top

C₂₄H₂₀O₇	V = 3870.8 (3) Å³
M_r = 420.42	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 36.511 (2) Å	µ = 0.89 mm⁻¹
b = 5.3275 (2) Å	T = 150 K
c = 20.0218 (8) Å	0.30 × 0.28 × 0.04 mm
β = 96.318 (5)°

Data collection top

Oxford Diffraction Gemini E diffractometer	3813 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	3383 reflections with I > 2.0σ(I)
T_min = 0.780, T_max = 0.965	R_int = 0.018
17338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 0.99	Δρ_max = 0.32 e Å⁻³
3813 reflections	Δρ_min = −0.21 e Å⁻³
280 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.12808 (2)	0.38440 (18)	0.09348 (4)	0.0198
C2	0.10246 (3)	0.5702 (2)	0.07942 (6)	0.0185
C3	0.09197 (4)	0.7295 (2)	0.12975 (6)	0.0191
C4	0.10576 (4)	0.6903 (3)	0.19901 (6)	0.0202
O5	0.09659 (3)	0.82336 (19)	0.24578 (5)	0.0261
C6	0.13177 (3)	0.4810 (2)	0.21237 (6)	0.0195
C7	0.14301 (4)	0.3455 (3)	0.15819 (6)	0.0190
C8	0.16981 (4)	0.1566 (3)	0.16701 (7)	0.0197
C9	0.18272 (4)	0.0989 (2)	0.23308 (7)	0.0201
C10	0.17096 (4)	0.2259 (3)	0.28733 (6)	0.0204
C11	0.14611 (4)	0.4195 (3)	0.27803 (7)	0.0205
H111	0.1386	0.5096	0.3144	0.0256*
C12	0.18915 (4)	0.1142 (3)	0.35190 (7)	0.0224
O13	0.21047 (3)	−0.09518 (18)	0.32781 (5)	0.0251
C14	0.20880 (4)	−0.1013 (3)	0.25958 (7)	0.0223
O15	0.22540 (3)	−0.2519 (2)	0.23027 (5)	0.0287
C16	0.21617 (4)	0.2917 (3)	0.39064 (7)	0.0288
H163	0.2033	0.4353	0.4063	0.0429*
H162	0.2289	0.2059	0.4301	0.0439*
H161	0.2342	0.3494	0.3624	0.0428*
C17	0.16119 (4)	0.0067 (3)	0.39501 (7)	0.0277
H171	0.1481	0.1395	0.4145	0.0409*
H172	0.1737	−0.0925	0.4316	0.0407*
H173	0.1438	−0.0978	0.3681	0.0410*
C18	0.18478 (4)	0.0411 (3)	0.10628 (7)	0.0213
O19	0.17671 (3)	−0.1689 (2)	0.08765 (6)	0.0334
C20	0.20997 (4)	0.2106 (3)	0.07285 (7)	0.0271
H203	0.2185	0.1277	0.0339	0.0398*
H202	0.2306	0.2608	0.1047	0.0413*
H201	0.1967	0.3604	0.0575	0.0414*
C21	0.06673 (4)	0.9261 (2)	0.11022 (7)	0.0208
O22	0.05637 (3)	1.08580 (19)	0.15665 (5)	0.0275
H221	0.0674	1.0316	0.1953	0.0432*
C23	0.05232 (4)	0.9535 (3)	0.04379 (7)	0.0221
C24	0.06218 (4)	0.7823 (2)	−0.00367 (6)	0.0198
C25	0.08781 (4)	0.5891 (2)	0.01261 (6)	0.0194
C26	0.09776 (4)	0.4252 (3)	−0.04086 (7)	0.0215
C27	0.07852 (4)	0.4357 (3)	−0.10100 (7)	0.0225
C28	0.04539 (4)	0.6033 (3)	−0.11489 (6)	0.0220
O29	0.04714 (3)	0.81622 (18)	−0.06783 (5)	0.0252
C30	0.04382 (5)	0.7261 (3)	−0.18347 (7)	0.0318
H301	0.0229	0.8361	−0.1902	0.0461*
H302	0.0663	0.8214	−0.1864	0.0468*
H303	0.0418	0.6015	−0.2176	0.0477*
C31	0.01040 (4)	0.4563 (3)	−0.10626 (8)	0.0307
H311	0.0115	0.3962	−0.0603	0.0455*
H313	−0.0111	0.5621	−0.1161	0.0455*
H312	0.0084	0.3170	−0.1366	0.0447*
H271	0.0845	0.3337	−0.1366	0.0260*
H261	0.1176	0.3146	−0.0317	0.0269*
H231	0.0354	1.0844	0.0313	0.0277*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0208 (5)	0.0204 (5)	0.0177 (4)	0.0048 (4)	−0.0006 (3)	−0.0008 (3)
C2	0.0172 (6)	0.0169 (6)	0.0212 (6)	0.0004 (5)	0.0018 (5)	0.0013 (5)
C3	0.0189 (6)	0.0175 (6)	0.0208 (6)	−0.0001 (5)	0.0021 (5)	0.0000 (5)
C4	0.0210 (6)	0.0188 (6)	0.0209 (6)	0.0001 (5)	0.0029 (5)	−0.0002 (5)
O5	0.0325 (5)	0.0262 (5)	0.0197 (5)	0.0085 (4)	0.0024 (4)	−0.0030 (4)
C6	0.0189 (6)	0.0183 (6)	0.0212 (6)	−0.0004 (5)	0.0016 (5)	0.0001 (5)
C7	0.0196 (6)	0.0184 (6)	0.0184 (6)	−0.0014 (5)	−0.0003 (5)	0.0008 (5)
C8	0.0188 (6)	0.0177 (6)	0.0224 (6)	−0.0007 (5)	0.0012 (5)	−0.0005 (5)
C9	0.0183 (6)	0.0179 (6)	0.0239 (6)	−0.0017 (5)	0.0007 (5)	0.0016 (5)
C10	0.0197 (6)	0.0202 (6)	0.0208 (6)	−0.0036 (5)	−0.0001 (5)	0.0019 (5)
C11	0.0223 (6)	0.0197 (6)	0.0194 (6)	−0.0015 (5)	0.0024 (5)	−0.0011 (5)
C12	0.0235 (7)	0.0204 (7)	0.0225 (6)	0.0008 (5)	−0.0003 (5)	0.0025 (5)
O13	0.0259 (5)	0.0233 (5)	0.0252 (5)	0.0044 (4)	−0.0011 (4)	0.0042 (4)
C14	0.0204 (6)	0.0206 (7)	0.0254 (7)	−0.0017 (5)	−0.0008 (5)	0.0028 (5)
O15	0.0273 (5)	0.0257 (5)	0.0332 (5)	0.0074 (4)	0.0034 (4)	0.0004 (4)
C16	0.0289 (7)	0.0285 (8)	0.0274 (7)	−0.0030 (6)	−0.0047 (6)	0.0012 (6)
C17	0.0302 (7)	0.0287 (7)	0.0242 (7)	−0.0029 (6)	0.0023 (6)	0.0047 (6)
C18	0.0184 (6)	0.0217 (7)	0.0227 (6)	0.0049 (5)	−0.0027 (5)	−0.0015 (5)
O19	0.0353 (6)	0.0259 (6)	0.0398 (6)	−0.0016 (5)	0.0080 (5)	−0.0107 (5)
C20	0.0250 (7)	0.0298 (8)	0.0269 (7)	0.0021 (6)	0.0044 (5)	−0.0014 (6)
C21	0.0221 (6)	0.0178 (6)	0.0227 (6)	0.0005 (5)	0.0029 (5)	−0.0008 (5)
O22	0.0335 (5)	0.0253 (5)	0.0229 (5)	0.0117 (4)	−0.0007 (4)	−0.0034 (4)
C23	0.0225 (6)	0.0179 (6)	0.0254 (7)	0.0036 (5)	−0.0001 (5)	0.0024 (5)
C24	0.0210 (6)	0.0189 (6)	0.0189 (6)	−0.0017 (5)	−0.0001 (5)	0.0028 (5)
C25	0.0191 (6)	0.0187 (6)	0.0203 (6)	−0.0007 (5)	0.0020 (5)	0.0005 (5)
C26	0.0202 (6)	0.0229 (7)	0.0217 (6)	0.0023 (5)	0.0032 (5)	0.0002 (5)
C27	0.0241 (7)	0.0236 (7)	0.0203 (6)	−0.0002 (5)	0.0047 (5)	−0.0009 (5)
C28	0.0248 (7)	0.0223 (7)	0.0183 (6)	−0.0003 (5)	−0.0005 (5)	0.0001 (5)
O29	0.0325 (5)	0.0213 (5)	0.0203 (5)	0.0048 (4)	−0.0042 (4)	0.0008 (4)
C30	0.0414 (9)	0.0323 (8)	0.0207 (7)	0.0030 (7)	−0.0013 (6)	0.0039 (6)
C31	0.0237 (7)	0.0268 (8)	0.0415 (8)	0.0009 (6)	0.0024 (6)	0.0010 (6)

Geometric parameters (Å, º) top

O1—C2	1.3696 (16)	C17—H173	0.962
O1—C7	1.3651 (15)	C18—O19	1.2052 (18)
C2—C3	1.4025 (18)	C18—C20	1.4982 (19)
C2—C25	1.3886 (18)	C20—H203	0.976
C3—C4	1.4375 (18)	C20—H202	0.968
C3—C21	1.4213 (18)	C20—H201	0.967
C4—O5	1.2490 (16)	C21—O22	1.3449 (16)
C4—C6	1.4700 (18)	C21—C23	1.3833 (19)
C6—C7	1.4016 (18)	O22—H221	0.880
C6—C11	1.3996 (18)	C23—C24	1.3926 (19)
C7—C8	1.4009 (19)	C23—H231	0.947
C8—C9	1.3891 (18)	C24—C25	1.4050 (19)
C8—C18	1.5175 (18)	C24—O29	1.3524 (15)
C9—C10	1.3875 (19)	C25—C26	1.4582 (18)
C9—C14	1.4879 (18)	C26—C27	1.3269 (19)
C10—C11	1.3727 (19)	C26—H261	0.937
C10—C12	1.5093 (18)	C27—C28	1.5048 (19)
C11—H111	0.938	C27—H271	0.941
C12—O13	1.4715 (17)	C28—O29	1.4714 (16)
C12—C16	1.5166 (19)	C28—C30	1.5162 (18)
C12—C17	1.5196 (19)	C28—C31	1.524 (2)
O13—C14	1.3610 (17)	C30—H301	0.960
C14—O15	1.1973 (17)	C30—H302	0.972
C16—H163	0.969	C30—H303	0.950
C16—H162	0.984	C31—H311	0.972
C16—H161	0.962	C31—H313	0.970
C17—H171	0.961	C31—H312	0.957
C17—H172	0.975

C2—O1—C7	119.81 (10)	H172—C17—H173	109.4
O1—C2—C3	121.60 (11)	C8—C18—O19	121.81 (13)
O1—C2—C25	115.63 (11)	C8—C18—C20	113.98 (11)
C3—C2—C25	122.77 (12)	O19—C18—C20	124.21 (13)
C2—C3—C4	120.74 (12)	C18—C20—H203	110.5
C2—C3—C21	117.93 (12)	C18—C20—H202	110.0
C4—C3—C21	121.32 (12)	H203—C20—H202	111.0
C3—C4—O5	123.14 (12)	C18—C20—H201	109.1
C3—C4—C6	115.85 (11)	H203—C20—H201	108.3
O5—C4—C6	121.01 (12)	H202—C20—H201	107.9
C4—C6—C7	119.24 (12)	C3—C21—O22	119.96 (12)
C4—C6—C11	121.07 (12)	C3—C21—C23	120.59 (12)
C7—C6—C11	119.68 (12)	O22—C21—C23	119.44 (12)
C6—C7—O1	122.41 (12)	C21—O22—H221	105.3
C6—C7—C8	122.17 (12)	C21—C23—C24	119.16 (12)
O1—C7—C8	115.41 (11)	C21—C23—H231	120.0
C7—C8—C9	116.00 (12)	C24—C23—H231	120.8
C7—C8—C18	119.90 (11)	C23—C24—C25	122.48 (12)
C9—C8—C18	123.96 (12)	C23—C24—O29	116.88 (12)
C8—C9—C10	122.38 (12)	C25—C24—O29	120.57 (12)
C8—C9—C14	129.44 (12)	C24—C25—C2	116.94 (12)
C10—C9—C14	108.15 (12)	C24—C25—C26	118.80 (12)
C9—C10—C11	121.15 (12)	C2—C25—C26	124.25 (12)
C9—C10—C12	109.47 (12)	C25—C26—C27	119.42 (12)
C11—C10—C12	129.38 (12)	C25—C26—H261	118.9
C6—C11—C10	118.48 (12)	C27—C26—H261	121.7
C6—C11—H111	120.0	C26—C27—C28	121.82 (12)
C10—C11—H111	121.6	C26—C27—H271	121.3
C10—C12—O13	102.52 (10)	C28—C27—H271	116.8
C10—C12—C16	113.10 (12)	C27—C28—O29	111.21 (11)
O13—C12—C16	107.61 (11)	C27—C28—C30	111.89 (12)
C10—C12—C17	112.04 (11)	O29—C28—C30	104.02 (11)
O13—C12—C17	108.25 (11)	C27—C28—C31	109.92 (12)
C16—C12—C17	112.61 (12)	O29—C28—C31	107.55 (11)
C12—O13—C14	112.35 (10)	C30—C28—C31	112.06 (12)
C9—C14—O13	107.28 (11)	C28—O29—C24	119.33 (10)
C9—C14—O15	130.08 (13)	C28—C30—H301	110.0
O13—C14—O15	122.60 (12)	C28—C30—H302	109.4
C12—C16—H163	110.2	H301—C30—H302	109.6
C12—C16—H162	110.1	C28—C30—H303	110.0
H163—C16—H162	108.0	H301—C30—H303	109.1
C12—C16—H161	110.3	H302—C30—H303	108.8
H163—C16—H161	109.0	C28—C31—H311	109.2
H162—C16—H161	109.1	C28—C31—H313	110.4
C12—C17—H171	110.4	H311—C31—H313	109.4
C12—C17—H172	110.0	C28—C31—H312	109.4
H171—C17—H172	107.9	H311—C31—H312	109.8
C12—C17—H173	110.0	H313—C31—H312	108.6
H171—C17—H173	109.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H161···O15ⁱ	0.96	2.55	3.4062 (19)	148
C20—H202···O13ⁱ	0.97	2.53	3.4918 (19)	171
O22—H221···O5	0.88	1.78	2.5922 (19)	153
C31—H313···O22ⁱⁱ	0.97	2.57	3.5170 (19)	165
C27—H271···O5ⁱⁱⁱ	0.94	2.58	3.4923 (19)	163

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀O₇
M_r	420.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	36.511 (2), 5.3275 (2), 20.0218 (8)
β (°)	96.318 (5)
V (Å³)	3870.8 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.30 × 0.28 × 0.04

Data collection
Diffractometer	Oxford Diffraction Gemini E
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.780, 0.965
No. of measured, independent and observed [I > 2.0σ(I)] reflections	17338, 3813, 3383
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 0.99
No. of reflections	3813
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H161···O15ⁱ	0.96	2.55	3.4062 (19)	148
C20—H202···O13ⁱ	0.97	2.53	3.4918 (19)	171
O22—H221···O5	0.88	1.78	2.5922 (19)	153
C31—H313···O22ⁱⁱ	0.97	2.57	3.5170 (19)	165
C27—H271···O5ⁱⁱⁱ	0.94	2.58	3.4923 (19)	163

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

Acknowledgements

The authors would like to acknowledge Ministry of Science, Technology and Innovation (MOSTI) for the e-science funding provided.

References

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Volume 66| Part 12| December 2010| Pages o3331-o3332

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

12-Acetyl-6-hy­dr­oxy-3,3,9,9-tetra­methyl­furo[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

12-Acetyl-6-hydroxy-3,3,9,9-tetramethylfuro[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione