1,3,6-Trihy-droxy-7-meth-oxy-2,8-bis-(3-methyl-but-2-en-yl)-9H-xanthen-9-one.

The title compound (trivial name α-mangostin), C(24)H(26)O(6), isolated from Cratoxylum glaucum, is characterized by a xanthone skeleton of three fused six-membered rings and two 3-methyl-but-2-enyl side chains. The three rings in the structure are nearly coplanar, with an r.m.s. deviation for the tricyclic ring system of 0.0014 Å. The two 3-methyl-but-2-enyl side chains are in (+)-synclinal and (-)-anti-clinal conformations. Intra-molecular O-H⋯O and C-H⋯O inter-actions occur. The crystal structure is stabilized by inter-molecular O-H⋯O, C-H⋯O and C-H⋯π inter-actions.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For related structures, see: Marek et al. (2003 ▶); Ndjakou et al. (2007 ▶); Boonnak et al. (2007 ▶). For the biological activity of Cratoxylum species, see: Boonnak et al. (2006 ▶); Bennett et al. (1993 ▶); Nguyen & Harrison (1998 ▶); Boonsri et al. (2006 ▶); Reutrakul et al. (2006 ▶).

Experimental

Crystal data

C24H26O6

M = 410.47

Orthorhombic,

a = 14.6818 (3) Å

b = 9.53505 (19) Å

c = 29.8893 (6) Å

V = 4184.24 (14) Å3

Z = 8

Cu Kα radiation

μ = 0.77 mm−1

T = 150 K

0.11 × 0.10 × 0.04 mm

Data collection

Oxford Diffraction Gemini E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.926, T max = 0.970

13773 measured reflections

4032 independent reflections

2812 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 0.88

4018 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.27 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/S1600536810049123/kp2293sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049123/kp2293Isup2.hkl

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

C24H26O6	Dx = 1.303 Mg m−3
Mr = 410.47	Melting point: 452 K
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5947 reflections
a = 14.6818 (3) Å	θ = 3.0–71.2°
b = 9.53505 (19) Å	µ = 0.77 mm−1
c = 29.8893 (6) Å	T = 150 K
V = 4184.24 (14) Å3	Plate, yellow
Z = 8	0.11 × 0.10 × 0.04 mm
F(000) = 1744

Oxford Diffraction Gemini E diffractometer	4032 independent reflections
Radiation source: sealed x-ray tube	2812 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω/2θ scans	θmax = 71.4°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −17→17
Tmin = 0.926, Tmax = 0.970	k = −11→11
13773 measured reflections	l = −36→29

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.113	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.08P)2 + 0.0P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.88	(Δ/σ)max = 0.0003
4018 reflections	Δρmax = 0.34 e Å−3
271 parameters	Δρmin = −0.27 e Å−3
0 restraints

Refinement. (sinθ X)2 was set to > 0.01 to eliminate reflection measured near the vicinity of the beam stop.

	x	y	z	Uiso*/Ueq
O1	0.87635 (7)	0.30339 (12)	0.25523 (4)	0.0309
C2	0.82099 (10)	0.22222 (17)	0.28118 (5)	0.0276
C3	0.72644 (10)	0.23373 (17)	0.27827 (5)	0.0279
C4	0.68351 (10)	0.32642 (17)	0.24630 (5)	0.0285
O5	0.59844 (7)	0.32795 (13)	0.24258 (4)	0.0368
C6	0.74439 (10)	0.41346 (17)	0.21923 (5)	0.0274
C7	0.83874 (10)	0.39435 (17)	0.22495 (5)	0.0274
C8	0.90312 (10)	0.46582 (18)	0.19999 (6)	0.0307
C9	0.87454 (10)	0.55982 (17)	0.16816 (6)	0.0307
O10	0.93348 (7)	0.63408 (13)	0.14256 (4)	0.0361
C11	0.78053 (10)	0.58382 (17)	0.16158 (5)	0.0292
C12	0.71573 (10)	0.51369 (18)	0.18686 (5)	0.0286
C13	0.61617 (10)	0.55256 (18)	0.17851 (6)	0.0305
C14	0.58048 (10)	0.47960 (19)	0.13754 (6)	0.0329
C15	0.54434 (11)	0.5383 (2)	0.10128 (6)	0.0416
C16	0.52901 (15)	0.6929 (3)	0.09490 (8)	0.0574
C17	0.51697 (14)	0.4474 (3)	0.06219 (7)	0.0634
O18	0.75300 (8)	0.68622 (13)	0.13202 (4)	0.0356
C19	0.76973 (12)	0.6541 (2)	0.08604 (6)	0.0444
C20	0.67452 (10)	0.14669 (17)	0.30706 (5)	0.0291
O21	0.58222 (7)	0.15647 (13)	0.30532 (4)	0.0349
C22	0.71415 (10)	0.05261 (18)	0.33651 (5)	0.0302
C23	0.65776 (11)	−0.03859 (19)	0.36731 (6)	0.0337
C24	0.63628 (11)	0.0336 (2)	0.41077 (6)	0.0370
C25	0.65495 (12)	−0.0099 (2)	0.45188 (7)	0.0441
C26	0.62764 (17)	0.0757 (3)	0.49190 (8)	0.0589
C27	0.7041 (2)	−0.1435 (3)	0.46259 (9)	0.0688
C28	0.81001 (11)	0.04585 (18)	0.33691 (6)	0.0309
C29	0.86367 (10)	0.12942 (18)	0.30953 (6)	0.0311
O30	0.84808 (8)	−0.04872 (13)	0.36537 (4)	0.0388
H81	0.9656	0.4502	0.2049	0.0363*
H131	0.6130	0.6516	0.1755	0.0361*
H132	0.5811	0.5267	0.2037	0.0360*
H141	0.5857	0.3795	0.1381	0.0387*
H161	0.5550	0.7236	0.0664	0.0850*
H163	0.5558	0.7469	0.1192	0.0852*
H162	0.4643	0.7120	0.0934	0.0857*
H171	0.4551	0.4673	0.0536	0.0945*
H173	0.5552	0.4712	0.0368	0.0938*
H172	0.5250	0.3454	0.0687	0.0952*
H191	0.7492	0.7303	0.0678	0.0666*
H193	0.8329	0.6388	0.0802	0.0658*
H192	0.7357	0.5710	0.0777	0.0666*
H231	0.6891	−0.1275	0.3725	0.0390*
H232	0.6016	−0.0609	0.3524	0.0393*
H241	0.6065	0.1214	0.4085	0.0447*
H261	0.6799	0.1001	0.5095	0.0886*
H263	0.5951	0.1616	0.4833	0.0880*
H262	0.5893	0.0198	0.5113	0.0878*
H271	0.7562	−0.1207	0.4801	0.1025*
H273	0.7216	−0.1943	0.4357	0.1020*
H272	0.6645	−0.2019	0.4808	0.1027*
H291	0.9267	0.1242	0.3103	0.0351*
H211	0.5707	0.2133	0.2842	0.0526*
H101	0.9842	0.6299	0.1553	0.0544*
H301	0.9064	−0.0397	0.3648	0.0578*

	U11	U22	U33	U12	U13	U23
O1	0.0172 (5)	0.0397 (6)	0.0357 (6)	0.0002 (4)	0.0001 (4)	0.0033 (5)
C2	0.0216 (7)	0.0330 (9)	0.0283 (8)	−0.0023 (6)	0.0008 (6)	−0.0033 (7)
C3	0.0220 (7)	0.0323 (8)	0.0295 (8)	−0.0012 (6)	−0.0005 (6)	−0.0042 (7)
C4	0.0207 (7)	0.0344 (8)	0.0303 (8)	−0.0001 (6)	0.0005 (6)	−0.0060 (7)
O5	0.0177 (5)	0.0478 (7)	0.0447 (7)	−0.0010 (5)	−0.0011 (5)	0.0055 (6)
C6	0.0213 (7)	0.0333 (8)	0.0277 (8)	−0.0005 (6)	0.0000 (6)	−0.0045 (6)
C7	0.0215 (7)	0.0320 (8)	0.0288 (8)	0.0007 (6)	−0.0009 (6)	−0.0023 (7)
C8	0.0171 (6)	0.0392 (9)	0.0357 (9)	−0.0008 (6)	−0.0007 (6)	−0.0030 (7)
C9	0.0242 (7)	0.0370 (9)	0.0309 (8)	−0.0037 (6)	0.0018 (6)	−0.0036 (7)
O10	0.0231 (5)	0.0468 (7)	0.0385 (7)	−0.0043 (5)	−0.0014 (5)	0.0069 (5)
C11	0.0255 (7)	0.0330 (8)	0.0290 (8)	0.0002 (6)	−0.0016 (6)	−0.0030 (7)
C12	0.0215 (7)	0.0351 (9)	0.0292 (8)	0.0012 (6)	−0.0009 (6)	−0.0053 (7)
C13	0.0209 (7)	0.0373 (9)	0.0335 (8)	0.0041 (6)	−0.0001 (6)	0.0011 (7)
C14	0.0191 (7)	0.0415 (9)	0.0381 (9)	0.0006 (6)	0.0003 (6)	−0.0012 (8)
C15	0.0220 (7)	0.0669 (13)	0.0358 (9)	0.0017 (7)	−0.0005 (7)	0.0024 (9)
C16	0.0424 (10)	0.0754 (15)	0.0545 (13)	0.0110 (10)	−0.0030 (9)	0.0238 (12)
C17	0.0384 (10)	0.111 (2)	0.0411 (12)	−0.0001 (11)	−0.0084 (9)	−0.0129 (13)
O18	0.0296 (5)	0.0420 (6)	0.0351 (6)	0.0015 (5)	−0.0008 (5)	0.0037 (5)
C19	0.0322 (9)	0.0691 (13)	0.0319 (9)	−0.0004 (8)	−0.0003 (7)	0.0081 (9)
C20	0.0205 (7)	0.0361 (8)	0.0309 (8)	−0.0021 (6)	0.0009 (6)	−0.0076 (7)
O21	0.0185 (5)	0.0470 (7)	0.0391 (7)	−0.0024 (4)	0.0005 (4)	0.0046 (5)
C22	0.0272 (7)	0.0342 (9)	0.0292 (8)	−0.0025 (6)	0.0003 (6)	−0.0042 (7)
C23	0.0267 (7)	0.0386 (9)	0.0357 (9)	−0.0044 (6)	−0.0003 (6)	0.0009 (8)
C24	0.0295 (8)	0.0401 (10)	0.0413 (10)	−0.0016 (7)	0.0025 (7)	0.0018 (8)
C25	0.0381 (9)	0.0531 (11)	0.0410 (10)	−0.0053 (8)	0.0000 (8)	−0.0002 (9)
C26	0.0679 (14)	0.0683 (15)	0.0405 (11)	−0.0041 (11)	0.0055 (10)	−0.0038 (11)
C27	0.0864 (18)	0.0722 (17)	0.0479 (13)	0.0185 (13)	−0.0092 (12)	0.0084 (12)
C28	0.0278 (7)	0.0343 (9)	0.0305 (8)	0.0011 (6)	−0.0035 (6)	−0.0018 (7)
C29	0.0190 (7)	0.0389 (9)	0.0354 (9)	0.0008 (6)	−0.0015 (6)	−0.0028 (7)
O30	0.0273 (5)	0.0451 (7)	0.0439 (7)	0.0007 (5)	−0.0033 (5)	0.0092 (6)

O1—C2	1.3644 (19)	C17—H171	0.962
O1—C7	1.370 (2)	C17—H173	0.972
C2—C3	1.395 (2)	C17—H172	0.999
C2—C29	1.376 (2)	O18—C19	1.429 (2)
C3—C4	1.446 (2)	C19—H191	0.957
C3—C20	1.418 (2)	C19—H193	0.954
C4—O5	1.2540 (19)	C19—H192	0.969
C4—C6	1.464 (2)	C20—O21	1.3594 (17)
C6—C7	1.408 (2)	C20—C22	1.385 (2)
C6—C12	1.424 (2)	O21—H211	0.849
C7—C8	1.384 (2)	C22—C23	1.513 (2)
C8—C9	1.373 (2)	C22—C28	1.409 (2)
C8—H81	0.941	C23—C24	1.503 (3)
C9—O10	1.3550 (19)	C23—H231	0.977
C9—C11	1.413 (2)	C23—H232	0.961
O10—H101	0.837	C24—C25	1.326 (3)
C11—C12	1.387 (2)	C24—H241	0.947
C11—O18	1.377 (2)	C25—C26	1.503 (3)
C12—C13	1.5284 (19)	C25—C27	1.499 (3)
C13—C14	1.503 (2)	C26—H261	0.959
C13—H131	0.950	C26—H263	0.982
C13—H132	0.944	C26—H262	0.969
C14—C15	1.330 (3)	C27—H271	0.952
C14—H141	0.957	C27—H273	0.974
C15—C16	1.503 (3)	C27—H272	0.972
C15—C17	1.509 (3)	C28—C29	1.388 (2)
C16—H161	0.979	C28—O30	1.360 (2)
C16—H163	0.972	C29—H291	0.928
C16—H162	0.968	O30—H301	0.860
C2—O1—C7	119.65 (12)	H171—C17—H173	107.0
O1—C2—C3	120.84 (14)	C15—C17—H172	112.2
O1—C2—C29	116.34 (13)	H171—C17—H172	110.8
C3—C2—C29	122.82 (15)	H173—C17—H172	108.1
C2—C3—C4	121.52 (14)	C11—O18—C19	114.47 (14)
C2—C3—C20	116.82 (14)	O18—C19—H191	109.2
C4—C3—C20	121.63 (13)	O18—C19—H193	112.0
C3—C4—O5	119.99 (14)	H191—C19—H193	108.6
C3—C4—C6	116.46 (13)	O18—C19—H192	109.6
O5—C4—C6	123.55 (15)	H191—C19—H192	108.1
C4—C6—C7	117.42 (14)	H193—C19—H192	109.2
C4—C6—C12	125.15 (13)	C3—C20—O21	118.21 (14)
C7—C6—C12	117.41 (14)	C3—C20—C22	122.61 (14)
C6—C7—O1	123.98 (14)	O21—C20—C22	119.18 (14)
C6—C7—C8	122.89 (15)	C20—O21—H211	105.7
O1—C7—C8	113.13 (13)	C20—C22—C23	121.94 (14)
C7—C8—C9	119.11 (14)	C20—C22—C28	117.05 (15)
C7—C8—H81	120.3	C23—C22—C28	121.00 (15)
C9—C8—H81	120.6	C22—C23—C24	112.16 (14)
C8—C9—O10	122.51 (14)	C22—C23—H231	109.8
C8—C9—C11	120.06 (14)	C24—C23—H231	111.0
O10—C9—C11	117.42 (15)	C22—C23—H232	108.3
C9—O10—H101	106.6	C24—C23—H232	108.8
C9—C11—C12	121.07 (15)	H231—C23—H232	106.7
C9—C11—O18	119.40 (14)	C23—C24—C25	127.89 (18)
C12—C11—O18	119.33 (13)	C23—C24—H241	116.0
C6—C12—C11	119.42 (13)	C25—C24—H241	116.1
C6—C12—C13	123.81 (14)	C24—C25—C26	120.8 (2)
C11—C12—C13	116.76 (14)	C24—C25—C27	124.3 (2)
C12—C13—C14	110.75 (13)	C26—C25—C27	114.9 (2)
C12—C13—H131	107.6	C25—C26—H261	110.8
C14—C13—H131	111.4	C25—C26—H263	112.1
C12—C13—H132	109.2	H261—C26—H263	109.3
C14—C13—H132	109.7	C25—C26—H262	109.4
H131—C13—H132	108.1	H261—C26—H262	105.7
C13—C14—C15	127.45 (17)	H263—C26—H262	109.4
C13—C14—H141	114.8	C25—C27—H271	108.1
C15—C14—H141	117.7	C25—C27—H273	111.9
C14—C15—C16	125.16 (19)	H271—C27—H273	110.9
C14—C15—C17	119.7 (2)	C25—C27—H272	108.6
C16—C15—C17	115.16 (19)	H271—C27—H272	107.7
C15—C16—H161	110.2	H273—C27—H272	109.6
C15—C16—H163	111.4	C22—C28—C29	122.40 (15)
H161—C16—H163	109.5	C22—C28—O30	116.51 (15)
C15—C16—H162	109.7	C29—C28—O30	121.09 (14)
H161—C16—H162	106.6	C28—C29—C2	118.29 (13)
H163—C16—H162	109.4	C28—C29—H291	121.4
C15—C17—H171	110.1	C2—C29—H291	120.3
C15—C17—H173	108.5	C28—O30—H301	109.3

CgA is the mid-point of the C14═C15 double bond.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H132···O5	0.94	2.24	2.885 (3)	125
C14—H141···O10i	0.96	2.36	3.304 (3)	168
O21—H211···C4	0.85	2.28	2.820 (3)	122
O21—H211···O5	0.85	1.71	2.499 (3)	155
O10—H101···O21ii	0.84	1.88	2.691 (3)	164
O30—H301···C14iii	0.86	2.56	3.424 (3)	178
O30—H301···C15iii	0.86	2.38	3.160 (3)	150
O30—H301···CgA	0.86	2.38	3.227 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

CgA is the mid-point of the C14=C15 double bond.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H132⋯O5	0.94	2.24	2.885 (3)	125
C14—H141⋯O10i	0.96	2.36	3.304 (3)	168
O21—H211⋯O5	0.85	1.71	2.499 (3)	155
O10—H101⋯O21ii	0.84	1.88	2.691 (3)	164
O30—H301⋯CgA	0.86	2.38	3.227 (3)	166

Symmetry codes: (i) ; (ii) .