12-Acetyl-6-hy-droxy-3,3,9,9-tetra-methyl-furo[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione.

The title compound, Artonol B, C(24)H(20)O(7), 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 pyran-oid 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 intra-molecular hydrogen-bond donor to the adjacent carbonyl group and also acts as an inter-molecular hydrogen-bond acceptor for the methyl groups of adjacent mol-ecules, 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 = 420.42

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 0.99

3813 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; 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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048592/kp2279Isup2.hkl

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

C24H20O7	F(000) = 1760
Mr = 420.42	Dx = 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

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

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(Fo2,0) + 2Fc2]/3
S = 0.99	(Δ/σ)max = 0.0003
3813 reflections	Δρmax = 0.32 e Å−3
280 parameters	Δρmin = −0.21 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) ; (ii) ; (iii) .