6-Butyryl-5-hy­droxy-4-phenyl­seselin

Aree, T.; Tip-pyang, S.; Sowanthip, P.

doi:10.1107/S160053681003415X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2464-o2465

https://doi.org/10.1107/S160053681003415X

Open

access

6-Butyryl-5-hydroxy-4-phenylseselin

Thammarat Aree,^a ^* Santi Tip-pyang ^a and Preecha Sowanthip ^a

^aDepartment of Chemistry, Faculty of Science, Chulalongkorn University, Phyathai Road, Pathumwan, Bangkok 10330, Thailand
^*Correspondence e-mail: thammarat.aree@gmail.com

(Received 12 August 2010; accepted 24 August 2010; online 28 August 2010)

In the title coumarin compound (systematic name: 6-butyryl-5-hydroxy-8,8-dimethyl-4-phenyl-2H,8H-benzo[1,2-b;3,4-b′]dipyran-2-one), C₂₄H₂₂O₅, also known as mammea A/AC cyclo D, the chromene and pyran rings are almost coplanar with a maximum deviation from the mean plane of 0.295 (2) Å. The attached phenyl group is inclined at 53.49 (8)° with respect to the chromene ring. The molecular structure is stabilized by an intramolecular O—H⋯O hydrogen bond. In the crystal, molecules are linked into sheets parallel to (101) by intermolecular C—H⋯O hydrogen bonds. Adjacent sheets are sustained by intermolecular C—H⋯π and π–π [centroid–centroid distance = 4.471 (2) Å] interactions.

Related literature

For the structural characterization of mammea A/AC cyclo D, see: Thebtaranonth et al. (1981 ); Morel et al. (1999 ); Kaweetripob et al. (2000 ). For its anti-HIV activity, see: Márquez et al. (2005 ); Bedoya et al. (2005 ) and for its anticancer activity, see: Reyes-Chilpa et al. (2004 ). For related coumarins, see: Mahidol et al. (2002 ). For a review on the cytotoxic activity of coumarins, see: Kostova (2005 ).

Experimental

Crystal data

C₂₄H₂₂O₅
M_r = 390.42
Monoclinic, C c
a = 17.0746 (4) Å
b = 13.4170 (4) Å
c = 8.7607 (3) Å
β = 90.341 (1)°
V = 2006.95 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.32 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.986
5484 measured reflections
2115 independent reflections
1714 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.03
2115 reflections
265 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1′–C6′ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O1"′	0.82	1.73	2.464 (3)	149
C3"′—H32⋯O2ⁱ	0.97	2.71	3.522 (5)	142
C4′—H4′⋯O2ⁱⁱ	0.93	2.70	3.396 (4)	132
C6"—H61"⋯Cg1ⁱⁱⁱ	0.96	2.75	3.646 (4)	156
Symmetry codes: (i) x, y+1, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al. 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681003415X/ds2051sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003415X/ds2051Isup2.hkl

checkCIF report

Comment top

The title coumarin compound, 6-butyryl-5-hydroxy-4-phenylseselin or mammea A/AC cyclo D (Fig. 1) was isolated from the hexane crude extract of the flowers of Mammea siamensis (Sarapee in Thai). Several coumarins derived from the same flowers have been reported, see for example Mahidol et al. 2002 and other references cited therein. In this work, we report the crystal structure of mammea A/AC cyclo D.

The molecular structure consists of one chromene ring, one pyran ring and one phenyl ring (Fig. 1). The chromene and pyran rings are almost coplanar. Atoms C2, C2", C4" and O1" most deviate from the mean plane by 0.133 (3), 0.295 (2), –0.154 (3) and –0.172 (2) Å, respectively. The butyraldehyde group, hydroxy group and atom O2 displace from the chromene plane to greater extents: 0.326 (3) Å, O3; 0.307 (4) Å, O1"'; and –0.303 (7) Å, C3"'. The methyl C4"', C5" and C6" atoms point upwards and downwards the chromene ring with torsion angles of –73.8 (6)° for C1"'—C2"'—C3"'—C4"', –142.8 (3)° for C4"—C3"—C2"—C5" and 91.7 (4)° for C4"—C3"—C2"—C6". The attached phenyl group inclines by 53.49 (8)° against the chromene ring. The molecular structure is stabilized by intramolecular O3—H···O1"' hydrogen bond.

In the crystal, the molecules are linked into sheets parallel to (101) by intermolecular, bifurcated C3"'—H32···O2(x, y + 1, z) and C4'—H4'···O2(x – 0.5, –y + 0.5, z + 0.5) hydrogen bonds (Fig. 2 and Table 1). The adjacent sheets are sustained by intermolecular C6"—H61"···π (ring C1'—C2'—C3'—C4'—C5'—C6') and π–π (two adjacent rings of C4a—C5—C6—C7—C8—C8a) interactions (Fig. 3). The corresponding distance from atom H to the phenyl-ring center is 2.75 Å and the interplanar spacing is 3.54 Å.

Related literature top

For the structural characterization of mammea A/AC cyclo D, see: Thebtaranonth et al. (1981); Morel et al. (1999); Kaweetripob et al. (2000). For its anti-HIV activity, see: Márquez et al. (2005); Bedoya et al. (2005) and for its anticancer activity, see: Reyes-Chilpa et al. (2004). For related coumarins, see: Mahidol et al. (2002). For a review on the cytotoxic activity of coumarins, see: Kostova (2005).

Experimental top

The title coumarin compound was isolated from the hexane crude extract of the flowers of Mammea siamensis, which is a Thai medicinal plant, locally known as Sarapee. This coumarin mammea A/AC cyclo D was known for almost 30 years. Its structure was ambigously characterized by spectroscopic techniques (Thebtaranonth et al., 1981; Morel et al., 1999; and Kaweetripob et al., 2000). Other coumarins were also isolated from the same flower (Mahidol et al., 2002 and other references cited therein).

The light yellow, block-like single crystals were obtained by slow evaporation of a hexane–dichloromethane solution at room temperature.

Structure description top

For the structural characterization of mammea A/AC cyclo D, see: Thebtaranonth et al. (1981); Morel et al. (1999); Kaweetripob et al. (2000). For its anti-HIV activity, see: Márquez et al. (2005); Bedoya et al. (2005) and for its anticancer activity, see: Reyes-Chilpa et al. (2004). For related coumarins, see: Mahidol et al. (2002). For a review on the cytotoxic activity of coumarins, see: Kostova (2005).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al. 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atomic numbering scheme and 40% probability displacement ellipsoids.
	Fig. 2. An infinite sheet parallel to (101) formed by intermolecular C—H···O hydrogen bonds (dotted lines).
	Fig. 3. Parallel, infinite sheets are sustained by intermolecular C—H···π and π–π interactions.

6-Butyryl-5-hydroxy-8,8-dimethyl-4-phenyl-2H,8H- benzo[1,2-b;3,4-b']dipyran-2-one top

Crystal data top

C₂₄H₂₂O₅	F(000) = 824
M_r = 390.42	D_x = 1.292 Mg m⁻³
Monoclinic, Cc	Melting point = 412–413 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.0746 (4) Å	Cell parameters from 2083 reflections
b = 13.4170 (4) Å	θ = 2.4–24.3°
c = 8.7607 (3) Å	µ = 0.09 mm⁻¹
β = 90.341 (1)°	T = 298 K
V = 2006.95 (10) Å³	Block, light yellow
Z = 4	0.40 × 0.32 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2115 independent reflections
Radiation source: fine-focus sealed tube	1714 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 26.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
T_min = 0.965, T_max = 0.986	k = −16→12
5484 measured reflections	l = −11→10

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0539P)² + 0.3001P] where P = (F_o² + 2F_c²)/3
2115 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.13 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₄H₂₂O₅	V = 2006.95 (10) Å³
M_r = 390.42	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 17.0746 (4) Å	µ = 0.09 mm⁻¹
b = 13.4170 (4) Å	T = 298 K
c = 8.7607 (3) Å	0.40 × 0.32 × 0.16 mm
β = 90.341 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2115 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1714 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.986	R_int = 0.023
5484 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
2115 reflections	Δρ_min = −0.14 e Å⁻³
265 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.37812 (12)	0.33800 (15)	0.0704 (2)	0.0539 (5)
C2	0.33746 (18)	0.2581 (2)	0.1325 (4)	0.0585 (8)
C3	0.26471 (17)	0.2825 (2)	0.2042 (4)	0.0527 (7)
H3	0.2335	0.2304	0.2382	0.063*
C4	0.23882 (15)	0.3763 (2)	0.2253 (3)	0.0417 (6)
C4A	0.28947 (13)	0.4585 (2)	0.1797 (3)	0.0381 (6)
C5	0.27705 (14)	0.5596 (2)	0.2138 (3)	0.0401 (6)
C6	0.32418 (15)	0.6360 (2)	0.1496 (3)	0.0418 (6)
C7	0.38818 (14)	0.6053 (2)	0.0584 (3)	0.0430 (6)
C8	0.40587 (14)	0.5060 (2)	0.0336 (3)	0.0426 (6)
C8A	0.35629 (14)	0.4350 (2)	0.0958 (3)	0.0413 (6)
O2	0.36629 (16)	0.17743 (18)	0.1167 (4)	0.0866 (8)
O3	0.22095 (11)	0.58102 (16)	0.3131 (2)	0.0545 (5)
H3O	0.2187	0.6415	0.3254	0.065*
C1'	0.15739 (15)	0.3906 (2)	0.2792 (3)	0.0423 (6)
C2'	0.12989 (18)	0.3393 (2)	0.4053 (3)	0.0517 (7)
H2'	0.1639	0.2998	0.4623	0.062*
C3'	0.0518 (2)	0.3467 (3)	0.4467 (3)	0.0634 (9)
H3'	0.0335	0.3115	0.5307	0.076*
C4'	0.00155 (18)	0.4058 (3)	0.3643 (4)	0.0651 (9)
H4'	−0.0505	0.4115	0.3936	0.078*
C5'	0.02778 (17)	0.4563 (2)	0.2394 (4)	0.0613 (8)
H5'	−0.0066	0.4958	0.1831	0.074*
C6'	0.10527 (16)	0.4491 (2)	0.1961 (3)	0.0518 (7)
H6'	0.1227	0.4836	0.1107	0.062*
O1"	0.43245 (11)	0.67654 (16)	−0.0081 (2)	0.0583 (6)
C2"	0.51443 (16)	0.6551 (2)	−0.0456 (3)	0.0512 (7)
C3"	0.52184 (19)	0.5511 (3)	−0.1026 (4)	0.0659 (9)
H3"	0.5624	0.5355	−0.1689	0.079*
C4"	0.47252 (17)	0.4806 (3)	−0.0619 (3)	0.0590 (8)
H4"	0.4802	0.4152	−0.0938	0.071*
C5"	0.5349 (2)	0.7323 (4)	−0.1653 (5)	0.0883 (13)
H51"	0.5019	0.7234	−0.2533	0.132*
H53"	0.5887	0.7246	−0.1941	0.132*
H52"	0.5271	0.7979	−0.1242	0.132*
C6"	0.56228 (19)	0.6696 (3)	0.0983 (4)	0.0650 (9)
H61"	0.5531	0.7352	0.1383	0.098*
H62"	0.6169	0.6621	0.0754	0.098*
H63"	0.5473	0.6207	0.1726	0.098*
O1"'	0.25223 (16)	0.75871 (17)	0.2771 (3)	0.0754 (7)
C1"'	0.30374 (18)	0.7407 (2)	0.1820 (4)	0.0534 (7)
C2"'	0.3419 (2)	0.8263 (2)	0.1013 (5)	0.0707 (9)
H21	0.3395	0.8142	−0.0078	0.085*
H22	0.3968	0.8285	0.1306	0.085*
C3"'	0.3056 (3)	0.9268 (3)	0.1337 (8)	0.1047 (16)
H31	0.2988	0.9338	0.2430	0.126*
H32	0.3413	0.9786	0.1007	0.126*
C4"'	0.2279 (3)	0.9421 (4)	0.0562 (8)	0.131 (2)
H41	0.2350	0.9428	−0.0524	0.197*
H42	0.2059	1.0045	0.0882	0.197*
H43	0.1931	0.8889	0.0832	0.197*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0436 (10)	0.0447 (11)	0.0734 (13)	−0.0010 (8)	0.0108 (9)	−0.0126 (9)
C2	0.0485 (16)	0.0413 (17)	0.086 (2)	−0.0067 (13)	0.0061 (16)	−0.0075 (15)
C3	0.0431 (15)	0.0435 (15)	0.0716 (19)	−0.0084 (12)	0.0022 (13)	0.0007 (14)
C4	0.0370 (13)	0.0426 (14)	0.0456 (15)	−0.0053 (11)	−0.0006 (11)	0.0026 (11)
C4A	0.0330 (13)	0.0428 (14)	0.0386 (13)	−0.0045 (11)	−0.0004 (10)	−0.0006 (11)
C5	0.0347 (12)	0.0447 (15)	0.0410 (13)	−0.0012 (11)	−0.0023 (10)	−0.0002 (12)
C6	0.0329 (12)	0.0441 (15)	0.0482 (14)	−0.0034 (11)	−0.0063 (10)	0.0018 (11)
C7	0.0322 (12)	0.0518 (16)	0.0450 (14)	−0.0107 (11)	−0.0031 (10)	0.0063 (12)
C8	0.0368 (12)	0.0485 (15)	0.0426 (13)	−0.0060 (11)	0.0001 (10)	−0.0046 (12)
C8A	0.0357 (14)	0.0437 (15)	0.0444 (14)	−0.0024 (11)	0.0000 (11)	−0.0062 (11)
O2	0.0718 (15)	0.0470 (14)	0.141 (2)	0.0045 (12)	0.0231 (15)	−0.0142 (15)
O3	0.0476 (11)	0.0509 (12)	0.0652 (13)	−0.0020 (9)	0.0161 (9)	−0.0061 (10)
C1'	0.0368 (13)	0.0457 (15)	0.0445 (13)	−0.0097 (11)	0.0020 (10)	−0.0001 (12)
C2'	0.0556 (17)	0.0551 (18)	0.0443 (15)	−0.0095 (14)	−0.0012 (12)	0.0048 (13)
C3'	0.0620 (19)	0.082 (2)	0.0466 (17)	−0.0215 (17)	0.0152 (14)	0.0053 (16)
C4'	0.0436 (16)	0.083 (2)	0.069 (2)	−0.0096 (15)	0.0154 (14)	−0.0080 (18)
C5'	0.0419 (15)	0.071 (2)	0.071 (2)	0.0020 (14)	−0.0005 (14)	0.0055 (16)
C6'	0.0408 (14)	0.0583 (18)	0.0564 (16)	−0.0082 (12)	0.0040 (11)	0.0115 (13)
O1"	0.0438 (11)	0.0547 (13)	0.0765 (14)	−0.0081 (9)	0.0076 (10)	0.0172 (10)
C2"	0.0376 (14)	0.0625 (18)	0.0537 (17)	−0.0125 (12)	0.0047 (11)	0.0103 (14)
C3"	0.0513 (17)	0.086 (3)	0.0604 (18)	−0.0193 (16)	0.0220 (14)	−0.0193 (17)
C4"	0.0473 (16)	0.066 (2)	0.0637 (19)	−0.0107 (15)	0.0178 (13)	−0.0189 (16)
C5"	0.059 (2)	0.117 (3)	0.089 (3)	−0.016 (2)	0.0098 (18)	0.045 (2)
C6"	0.0623 (19)	0.066 (2)	0.067 (2)	−0.0040 (15)	−0.0097 (15)	−0.0067 (16)
O1"'	0.0721 (15)	0.0505 (13)	0.1036 (19)	0.0059 (11)	0.0179 (14)	−0.0090 (12)
C1"'	0.0393 (14)	0.0468 (16)	0.0739 (19)	−0.0003 (12)	−0.0069 (14)	0.0006 (15)
C2"'	0.0588 (19)	0.0437 (18)	0.110 (3)	−0.0058 (14)	−0.0009 (18)	0.0087 (18)
C3"'	0.089 (3)	0.047 (2)	0.178 (5)	0.001 (2)	0.006 (3)	0.011 (3)
C4"'	0.107 (4)	0.086 (4)	0.200 (6)	0.037 (3)	−0.002 (4)	0.023 (4)

Geometric parameters (Å, º) top

O1—C8A	1.372 (3)	C5'—C6'	1.382 (4)
O1—C2	1.389 (4)	C5'—H5'	0.9300
C2—O2	1.198 (4)	C6'—H6'	0.9300
C2—C3	1.433 (4)	O1"—C2"	1.468 (3)
C3—C4	1.347 (4)	C2"—C3"	1.488 (5)
C3—H3	0.9300	C2"—C6"	1.510 (4)
C4—C4A	1.458 (3)	C2"—C5"	1.516 (5)
C4—C1'	1.483 (4)	C3"—C4"	1.317 (4)
C4A—C8A	1.397 (3)	C3"—H3"	0.9300
C4A—C5	1.406 (3)	C4"—H4"	0.9300
C5—O3	1.329 (3)	C5"—H51"	0.9600
C5—C6	1.421 (4)	C5"—H53"	0.9600
C6—C7	1.418 (4)	C5"—H52"	0.9600
C6—C1"'	1.476 (4)	C6"—H61"	0.9600
C7—O1"	1.353 (3)	C6"—H62"	0.9600
C7—C8	1.385 (4)	C6"—H63"	0.9600
C8—C8A	1.388 (4)	O1"'—C1"'	1.239 (4)
C8—C4"	1.457 (4)	C1"'—C2"'	1.500 (5)
O3—H3O	0.8200	C2"'—C3"'	1.511 (6)
C1'—C2'	1.385 (4)	C2"'—H21	0.9700
C1'—C6'	1.389 (4)	C2"'—H22	0.9700
C2'—C3'	1.387 (4)	C3"'—C4"'	1.501 (7)
C2'—H2'	0.9300	C3"'—H31	0.9700
C3'—C4'	1.371 (5)	C3"'—H32	0.9700
C3'—H3'	0.9300	C4"'—H41	0.9600
C4'—C5'	1.365 (4)	C4"'—H42	0.9600
C4'—H4'	0.9300	C4"'—H43	0.9600

C8A—O1—C2	122.1 (2)	C7—O1"—C2"	119.6 (2)
O2—C2—O1	116.5 (3)	O1"—C2"—C3"	110.0 (2)
O2—C2—C3	127.9 (3)	O1"—C2"—C6"	107.5 (2)
O1—C2—C3	115.6 (3)	C3"—C2"—C6"	110.7 (3)
C4—C3—C2	124.1 (3)	O1"—C2"—C5"	104.2 (3)
C4—C3—H3	118.0	C3"—C2"—C5"	112.8 (3)
C2—C3—H3	118.0	C6"—C2"—C5"	111.3 (3)
C3—C4—C4A	118.2 (2)	C4"—C3"—C2"	121.8 (3)
C3—C4—C1'	118.3 (2)	C4"—C3"—H3"	119.1
C4A—C4—C1'	123.2 (2)	C2"—C3"—H3"	119.1
C8A—C4A—C5	117.0 (2)	C3"—C4"—C8	119.4 (3)
C8A—C4A—C4	117.5 (2)	C3"—C4"—H4"	120.3
C5—C4A—C4	125.5 (2)	C8—C4"—H4"	120.3
O3—C5—C4A	117.2 (2)	C2"—C5"—H51"	109.5
O3—C5—C6	121.0 (2)	C2"—C5"—H53"	109.5
C4A—C5—C6	121.7 (2)	H51"—C5"—H53"	109.5
C7—C6—C5	117.0 (2)	C2"—C5"—H52"	109.5
C7—C6—C1"'	124.6 (3)	H51"—C5"—H52"	109.5
C5—C6—C1"'	118.4 (3)	H53"—C5"—H52"	109.5
O1"—C7—C8	119.3 (2)	C2"—C6"—H61"	109.5
O1"—C7—C6	118.2 (2)	C2"—C6"—H62"	109.5
C8—C7—C6	122.5 (2)	H61"—C6"—H62"	109.5
C7—C8—C8A	117.7 (2)	C2"—C6"—H63"	109.5
C7—C8—C4"	119.1 (3)	H61"—C6"—H63"	109.5
C8A—C8—C4"	123.1 (3)	H62"—C6"—H63"	109.5
O1—C8A—C8	114.8 (2)	O1"'—C1"'—C6	119.0 (3)
O1—C8A—C4A	121.5 (2)	O1"'—C1"'—C2"'	118.7 (3)
C8—C8A—C4A	123.7 (2)	C6—C1"'—C2"'	122.3 (3)
C5—O3—H3O	109.5	C1"'—C2"'—C3"'	114.5 (3)
C2'—C1'—C6'	118.6 (2)	C1"'—C2"'—H21	108.6
C2'—C1'—C4	120.8 (3)	C3"'—C2"'—H21	108.6
C6'—C1'—C4	120.3 (2)	C1"'—C2"'—H22	108.6
C1'—C2'—C3'	120.2 (3)	C3"'—C2"'—H22	108.6
C1'—C2'—H2'	119.9	H21—C2"'—H22	107.6
C3'—C2'—H2'	119.9	C4"'—C3"'—C2"'	113.6 (4)
C4'—C3'—C2'	120.2 (3)	C4"'—C3"'—H31	108.9
C4'—C3'—H3'	119.9	C2"'—C3"'—H31	108.9
C2'—C3'—H3'	119.9	C4"'—C3"'—H32	108.9
C5'—C4'—C3'	120.1 (3)	C2"'—C3"'—H32	108.9
C5'—C4'—H4'	119.9	H31—C3"'—H32	107.7
C3'—C4'—H4'	119.9	C3"'—C4"'—H41	109.5
C4'—C5'—C6'	120.3 (3)	C3"'—C4"'—H42	109.5
C4'—C5'—H5'	119.9	H41—C4"'—H42	109.5
C6'—C5'—H5'	119.9	C3"'—C4"'—H43	109.5
C5'—C6'—C1'	120.5 (3)	H41—C4"'—H43	109.5
C5'—C6'—H6'	119.8	H42—C4"'—H43	109.5
C1'—C6'—H6'	119.8

C8A—O1—C2—O2	−172.2 (3)	C4—C4A—C8A—O1	−6.5 (3)
C8A—O1—C2—C3	9.4 (4)	C5—C4A—C8A—C8	−6.3 (3)
O2—C2—C3—C4	175.7 (4)	C4—C4A—C8A—C8	174.1 (2)
O1—C2—C3—C4	−6.1 (5)	C3—C4—C1'—C2'	50.3 (4)
C2—C3—C4—C4A	−3.2 (4)	C4A—C4—C1'—C2'	−136.1 (3)
C2—C3—C4—C1'	170.7 (3)	C3—C4—C1'—C6'	−124.1 (3)
C3—C4—C4A—C8A	9.5 (3)	C4A—C4—C1'—C6'	49.6 (4)
C1'—C4—C4A—C8A	−164.1 (2)	C6'—C1'—C2'—C3'	0.0 (4)
C3—C4—C4A—C5	−170.0 (2)	C4—C1'—C2'—C3'	−174.5 (3)
C1'—C4—C4A—C5	16.3 (4)	C1'—C2'—C3'—C4'	−0.8 (5)
C8A—C4A—C5—O3	−169.6 (2)	C2'—C3'—C4'—C5'	1.1 (5)
C4—C4A—C5—O3	9.9 (3)	C3'—C4'—C5'—C6'	−0.7 (5)
C8A—C4A—C5—C6	8.1 (3)	C4'—C5'—C6'—C1'	−0.2 (5)
C4—C4A—C5—C6	−172.4 (2)	C2'—C1'—C6'—C5'	0.5 (4)
O3—C5—C6—C7	173.0 (2)	C4—C1'—C6'—C5'	175.0 (3)
C4A—C5—C6—C7	−4.6 (3)	C8—C7—O1"—C2"	−27.2 (3)
O3—C5—C6—C1"'	−6.8 (3)	C6—C7—O1"—C2"	153.9 (2)
C4A—C5—C6—C1"'	175.5 (2)	C7—O1"—C2"—C3"	38.7 (3)
C5—C6—C7—O1"	177.9 (2)	C7—O1"—C2"—C6"	−81.9 (3)
C1"'—C6—C7—O1"	−2.3 (4)	C7—O1"—C2"—C5"	159.9 (3)
C5—C6—C7—C8	−1.1 (3)	O1"—C2"—C3"—C4"	−27.0 (4)
C1"'—C6—C7—C8	178.8 (2)	C6"—C2"—C3"—C4"	91.7 (4)
O1"—C7—C8—C8A	−176.1 (2)	C5"—C2"—C3"—C4"	−142.8 (3)
C6—C7—C8—C8A	2.9 (4)	C2"—C3"—C4"—C8	4.1 (5)
O1"—C7—C8—C4"	0.9 (4)	C7—C8—C4"—C3"	10.7 (4)
C6—C7—C8—C4"	179.8 (2)	C8A—C8—C4"—C3"	−172.5 (3)
C2—O1—C8A—C8	176.2 (3)	C7—C6—C1"'—O1"'	−171.8 (3)
C2—O1—C8A—C4A	−3.2 (4)	C5—C6—C1"'—O1"'	8.1 (4)
C7—C8—C8A—O1	−178.4 (2)	C7—C6—C1"'—C2"'	9.6 (4)
C4"—C8—C8A—O1	4.7 (3)	C5—C6—C1"'—C2"'	−170.5 (3)
C7—C8—C8A—C4A	0.9 (4)	O1"'—C1"'—C2"'—C3"'	−6.7 (5)
C4"—C8—C8A—C4A	−175.9 (2)	C6—C1"'—C2"'—C3"'	171.9 (3)
C5—C4A—C8A—O1	173.1 (2)	C1"'—C2"'—C3"'—C4"'	−73.8 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1'–C6'ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1"′	0.82	1.73	2.464 (3)	149
C3"′—H32···O2ⁱ	0.97	2.71	3.522 (5)	142
C4′—H4′···O2ⁱⁱ	0.93	2.70	3.396 (4)	132
C6"—H61"···Cg1ⁱⁱⁱ	0.96	2.75	3.646 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂O₅
M_r	390.42
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	17.0746 (4), 13.4170 (4), 8.7607 (3)
β (°)	90.341 (1)
V (Å³)	2006.95 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.32 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5484, 2115, 1714
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.03
No. of reflections	2115
No. of parameters	265
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al. 2006).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1'–C6'ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1"'	0.82	1.73	2.464 (3)	148.7
C3"'—H32···O2ⁱ	0.97	2.71	3.522 (5)	142.2
C4'—H4'···O2ⁱⁱ	0.93	2.70	3.396 (4)	132.1
C6"—H61"···Cg1ⁱⁱⁱ	0.96	2.75	3.646 (4)	156

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

Acknowledgements

This work was supported by the Thai Government Stimulus Package 2 (TKK2555), under the Project for the Establishment of a Comprehensive Center for Innovative Food, Health Products and Agriculture (PERFECTA), the Center for Petroleum, Petrochemicals and Advanced Materials, Chulalongkorn University (to TA), the National Research University Project of CHE and the Ratchadaphiseksomphot Endowment Fund (FW001A) (to ST).

References

Bedoya, L. M., Beltrán, M., Sancho, R., Olmedo, D. A., Sánchez-Palomino, S., Del Olmo, E., López-Pérez, J. L., Muñoz, E. & San Feliciano, A. (2005). Bioorg. Med. Chem. Lett. 15, 4447–4450. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kaweetripob, W., Mahidol, C., Prawat, H. & Ruchirawat, S. (2000). Pharm. Biol. 38, 55–57. Web of Science CrossRef CAS PubMed Google Scholar
Kostova, I. (2005). Curr. Med. Chem. Anti-Cancer Agents, 5, 29–46. CrossRef PubMed CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mahidol, C., Kaweetripob, W., Prawat, H. & Ruchirawat, S. (2002). J. Nat. Prod. 65, 757–760. Web of Science CrossRef PubMed CAS Google Scholar
Márquez, N., Sancho, R., Bedoya, L. M., Alcamí, J., López-Pérez, J. L., San Feliciano, A., Fiebich, B. L. & Muñoz, E. (2005). Antivir. Res. 66, 137–145. Web of Science PubMed Google Scholar
Morel, C., Guilet, D., Oger, J.-M., Séraphin, D., Sévenet, T., Wiart, C., Hadi, A. H. A., Richomme, P. & Bruneton, J. (1999). Phytochemistry, 50, 1243–1247. Web of Science CrossRef CAS Google Scholar
Reyes-Chilpa, R., Estrada-Muñiz, E., Ramírez Apan, T., Amekraz, B., Aumelas, A., Jankowski, C. K. & Vázquez-Torres, M. (2004). Life Sci. 75, 1635–1647. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thebtaranonth, C., Imraporn, S. & Padungkul, N. (1981). Phytochemistry, 20, 2305–2306. CrossRef CAS Web of Science Google Scholar