Arctigenin: a lignan from Arctium lappa

Gao, H.; Li, G.; Zhang, J.; Zeng, J.

doi:10.1107/S1600536808021752

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1538

doi:10.1107/S1600536808021752

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Arctigenin: a lignan from Arctium lappa

Haiyan Gao,^a Guanglei Li,^a Junhe Zhang ^a and Jie Zeng ^a ^*

^aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China
^*Correspondence e-mail: j_zeng@yahoo.cn

(Received 2 July 2008; accepted 13 July 2008; online 19 July 2008)

The title compound {systematic name: (3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one}, C₂₁H₂₄O₆, has a dibenzylbutyrolactone skeleton. The two aromatic rings are inclined at a dihedral angle of 68.75 (7)° with respect to each other. The lactone ring adopts an envelope conformation. A series of O—H⋯O and C—H⋯O hydrogen bonds contribute to the stabilization of the crystal packing. The absolute configuration was assigned on the basis of the published literature.

Related literature

For related literature, see: Awale et al. (2006 ). For a similar structure, see: Bruno-Colmenárez et al. (2007 ).

Experimental

Crystal data

C₂₁H₂₄O₆
M_r = 372.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.4845 (19) Å
b = 10.065 (2) Å
c = 19.915 (4) Å
V = 1901.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.987, T_max = 0.991
13910 measured reflections
2581 independent reflections
2449 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.079
S = 1.06
2581 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.90 (2)	2.04 (2)	2.8280 (17)	146 (2)
O5—H5⋯O6	0.90 (2)	2.22 (2)	2.6799 (18)	111.7 (17)
O5—H5⋯O1ⁱ	0.90 (2)	2.58 (2)	3.2406 (18)	130.8 (16)
C3—H3⋯O5ⁱⁱ	0.95	2.34	3.278 (2)	168
C14—H14A⋯O4ⁱⁱⁱ	0.99	2.86	3.687 (2)	142
C14—H14B⋯O5^iv	0.99	2.42	3.373 (2)	162
C20—H20⋯O4ⁱⁱⁱ	0.95	2.53	3.446 (2)	162
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021752/bt2739sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021752/bt2739Isup2.hkl

checkCIF report

Comment top

Arctigenin has been identified as an antitumor agent with the ability to eliminate the tolerance of cancer cells to nutrient strarvation (Awale et al., 2006).

The title compound has a dibenzylbutyrolactone skeleton (Fig. 1). The two aromatic rings have a dihedral angle of 68.75 (7)°. The lactone ring adopts an envelope conformation. A series of O—H···O and C—H···O hydrogen bonds contribute to the stabilization of the crystal packing (Table 1).

Related literature top

For related literature, see: Awale et al. (2006). For a similar structure, see: Bruno-Colmenárez et al. (2007).

Experimental top

Arctigenin was isolated from Chinese medicine Arctium lappa. Crystal blocks were obtained by natural evaporation of a methanolic solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids.

(3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy- 3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one top

Crystal data top

C₂₁H₂₄O₆	F(000) = 792
M_r = 372.40	D_x = 1.301 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5995 reflections
a = 9.4845 (19) Å	θ = 2.3–27.9°
b = 10.065 (2) Å	µ = 0.10 mm⁻¹
c = 19.915 (4) Å	T = 113 K
V = 1901.2 (7) Å³	Block, colourless
Z = 4	0.14 × 0.12 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2581 independent reflections
Radiation source: rotating anode	2449 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.037
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.8°, θ_min = 2.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→13
T_min = 0.987, T_max = 0.991	l = −26→16
13910 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0475P)² + 0.1518P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2581 reflections	Δρ_max = 0.20 e Å⁻³
251 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (3)

Crystal data top

C₂₁H₂₄O₆	V = 1901.2 (7) Å³
M_r = 372.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.4845 (19) Å	µ = 0.10 mm⁻¹
b = 10.065 (2) Å	T = 113 K
c = 19.915 (4) Å	0.14 × 0.12 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2581 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2449 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.037
13910 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.20 e Å⁻³
2581 reflections	Δρ_min = −0.15 e Å⁻³
251 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	0.07380 (13)	0.28900 (13)	0.73971 (6)	0.0287 (3)
O2	0.23820 (12)	0.17843 (12)	0.82576 (5)	0.0228 (3)
O3	0.38552 (14)	0.79457 (13)	0.92594 (6)	0.0329 (3)
O4	0.34335 (15)	0.69713 (14)	1.02429 (6)	0.0362 (3)
O5	0.96166 (13)	0.15373 (12)	0.87738 (6)	0.0226 (3)
H5	1.036 (2)	0.195 (2)	0.8592 (10)	0.034*
O6	1.04322 (12)	0.40766 (12)	0.88872 (6)	0.0241 (3)
C1	0.44649 (17)	0.48348 (17)	0.79244 (7)	0.0196 (3)
C2	0.35798 (18)	0.53926 (18)	0.74441 (8)	0.0230 (3)
H2	0.3827	0.6219	0.7246	0.028*
C3	0.23339 (18)	0.47622 (18)	0.72471 (8)	0.0247 (4)
H3	0.1747	0.5159	0.6917	0.030*
C4	0.19554 (17)	0.35649 (18)	0.75310 (8)	0.0226 (3)
C5	0.28519 (17)	0.29699 (17)	0.80056 (7)	0.0196 (3)
C6	0.40879 (17)	0.35955 (17)	0.81937 (7)	0.0192 (3)
H6	0.4693	0.3180	0.8511	0.023*
C7	−0.0319 (2)	0.3594 (2)	0.70329 (11)	0.0412 (5)
H7A	−0.0003	0.3730	0.6569	0.062*
H7B	−0.0485	0.4458	0.7246	0.062*
H7C	−0.1196	0.3079	0.7033	0.062*
C8	0.32263 (19)	0.11735 (19)	0.87673 (9)	0.0276 (4)
H8A	0.3305	0.1774	0.9153	0.041*
H8B	0.4168	0.0988	0.8588	0.041*
H8C	0.2784	0.0340	0.8910	0.041*
C9	0.57710 (16)	0.55340 (17)	0.81719 (7)	0.0209 (3)
H9A	0.6165	0.6068	0.7799	0.025*
H9B	0.6482	0.4855	0.8294	0.025*
C10	0.55425 (17)	0.64553 (16)	0.87818 (8)	0.0213 (3)
H10	0.6479	0.6827	0.8916	0.026*
C11	0.4557 (2)	0.76166 (18)	0.86314 (9)	0.0287 (4)
H11A	0.5100	0.8389	0.8464	0.034*
H11B	0.3856	0.7361	0.8286	0.034*
C12	0.39834 (18)	0.69247 (18)	0.96988 (8)	0.0257 (4)
C13	0.48662 (16)	0.58224 (16)	0.94058 (8)	0.0192 (3)
H13	0.4229	0.5086	0.9259	0.023*
C14	0.58852 (17)	0.52865 (17)	0.99399 (7)	0.0211 (3)
H14A	0.6435	0.6035	1.0129	0.025*
H14B	0.5334	0.4884	1.0310	0.025*
C15	0.68864 (17)	0.42650 (16)	0.96613 (8)	0.0194 (3)
C16	0.65324 (16)	0.29296 (17)	0.96147 (7)	0.0205 (3)
H16	0.5651	0.2633	0.9785	0.025*
C17	0.74541 (16)	0.20166 (17)	0.93208 (7)	0.0206 (3)
H17	0.7201	0.1105	0.9295	0.025*
C18	0.87370 (16)	0.24419 (16)	0.90675 (7)	0.0188 (3)
C19	0.91196 (16)	0.37751 (17)	0.91323 (7)	0.0187 (3)
C20	0.82073 (16)	0.46753 (17)	0.94260 (7)	0.0192 (3)
H20	0.8479	0.5580	0.9469	0.023*
C21	1.08409 (19)	0.54337 (18)	0.89079 (10)	0.0329 (4)
H21A	1.0905	0.5726	0.9376	0.049*
H21B	1.0139	0.5973	0.8671	0.049*
H21C	1.1761	0.5538	0.8691	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0263 (6)	0.0277 (7)	0.0322 (6)	−0.0037 (6)	−0.0070 (5)	0.0021 (5)
O2	0.0269 (6)	0.0178 (6)	0.0237 (5)	0.0014 (5)	0.0016 (5)	0.0025 (4)
O3	0.0430 (7)	0.0206 (6)	0.0353 (7)	0.0115 (6)	0.0054 (6)	0.0006 (5)
O4	0.0416 (7)	0.0322 (8)	0.0349 (7)	0.0107 (7)	0.0139 (6)	−0.0030 (6)
O5	0.0210 (5)	0.0180 (6)	0.0288 (6)	0.0004 (5)	0.0004 (5)	−0.0031 (5)
O6	0.0187 (5)	0.0194 (6)	0.0342 (6)	−0.0017 (5)	0.0050 (5)	−0.0041 (5)
C1	0.0205 (7)	0.0212 (8)	0.0171 (7)	0.0035 (7)	0.0033 (6)	0.0004 (6)
C2	0.0258 (8)	0.0209 (8)	0.0222 (8)	0.0017 (7)	0.0033 (6)	0.0036 (6)
C3	0.0247 (8)	0.0270 (9)	0.0222 (8)	0.0030 (7)	−0.0030 (6)	0.0041 (7)
C4	0.0225 (7)	0.0241 (9)	0.0214 (7)	0.0008 (7)	−0.0002 (6)	−0.0028 (6)
C5	0.0250 (8)	0.0159 (7)	0.0179 (7)	0.0034 (7)	0.0053 (6)	0.0007 (6)
C6	0.0218 (7)	0.0200 (8)	0.0158 (7)	0.0060 (7)	0.0023 (6)	−0.0002 (6)
C7	0.0310 (10)	0.0340 (11)	0.0584 (12)	−0.0034 (10)	−0.0192 (9)	0.0041 (10)
C8	0.0271 (8)	0.0259 (9)	0.0297 (9)	0.0047 (8)	0.0052 (7)	0.0108 (7)
C9	0.0193 (7)	0.0229 (8)	0.0206 (7)	0.0009 (7)	0.0030 (6)	0.0030 (6)
C10	0.0223 (7)	0.0177 (8)	0.0237 (7)	−0.0003 (7)	0.0015 (6)	0.0014 (6)
C11	0.0358 (9)	0.0193 (8)	0.0308 (9)	0.0049 (8)	0.0032 (7)	0.0029 (7)
C12	0.0250 (8)	0.0215 (8)	0.0307 (8)	0.0035 (7)	0.0022 (7)	−0.0025 (7)
C13	0.0187 (7)	0.0162 (8)	0.0227 (8)	0.0006 (6)	0.0017 (6)	−0.0015 (6)
C14	0.0213 (7)	0.0222 (8)	0.0198 (7)	0.0007 (7)	0.0028 (6)	0.0000 (6)
C15	0.0208 (7)	0.0223 (8)	0.0149 (7)	0.0024 (7)	−0.0018 (6)	0.0008 (6)
C16	0.0192 (7)	0.0220 (8)	0.0204 (7)	−0.0012 (7)	0.0001 (6)	0.0027 (6)
C17	0.0218 (7)	0.0182 (8)	0.0218 (7)	−0.0020 (7)	−0.0035 (6)	0.0019 (6)
C18	0.0193 (7)	0.0182 (8)	0.0190 (7)	0.0037 (6)	−0.0036 (6)	−0.0017 (6)
C19	0.0163 (7)	0.0217 (8)	0.0183 (7)	−0.0010 (6)	−0.0018 (6)	0.0009 (6)
C20	0.0204 (7)	0.0186 (8)	0.0188 (7)	−0.0003 (7)	−0.0023 (6)	−0.0009 (6)
C21	0.0260 (9)	0.0208 (9)	0.0519 (11)	−0.0064 (8)	0.0114 (8)	−0.0055 (8)

Geometric parameters (Å, º) top

O1—C4	1.366 (2)	C9—C10	1.543 (2)
O1—C7	1.426 (2)	C9—H9A	0.9900
O2—C5	1.369 (2)	C9—H9B	0.9900
O2—C8	1.432 (2)	C10—C11	1.526 (2)
O3—C12	1.355 (2)	C10—C13	1.537 (2)
O3—C11	1.455 (2)	C10—H10	1.0000
O4—C12	1.203 (2)	C11—H11A	0.9900
O5—C18	1.3665 (19)	C11—H11B	0.9900
O5—H5	0.90 (2)	C12—C13	1.507 (2)
O6—C19	1.3712 (19)	C13—C14	1.535 (2)
O6—C21	1.421 (2)	C13—H13	1.0000
C1—C2	1.391 (2)	C14—C15	1.506 (2)
C1—C6	1.404 (2)	C14—H14A	0.9900
C1—C9	1.508 (2)	C14—H14B	0.9900
C2—C3	1.398 (2)	C15—C16	1.389 (2)
C2—H2	0.9500	C15—C20	1.400 (2)
C3—C4	1.379 (2)	C16—C17	1.397 (2)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.405 (2)	C17—C18	1.385 (2)
C5—C6	1.383 (2)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.396 (2)
C7—H7A	0.9800	C19—C20	1.383 (2)
C7—H7B	0.9800	C20—H20	0.9500
C7—H7C	0.9800	C21—H21A	0.9800
C8—H8A	0.9800	C21—H21B	0.9800
C8—H8B	0.9800	C21—H21C	0.9800
C8—H8C	0.9800

C4—O1—C7	116.50 (15)	C9—C10—H10	108.1
C5—O2—C8	116.88 (13)	O3—C11—C10	106.62 (13)
C12—O3—C11	109.96 (13)	O3—C11—H11A	110.4
C18—O5—H5	109.9 (15)	C10—C11—H11A	110.4
C19—O6—C21	116.75 (13)	O3—C11—H11B	110.4
C2—C1—C6	117.88 (16)	C10—C11—H11B	110.4
C2—C1—C9	122.16 (15)	H11A—C11—H11B	108.6
C6—C1—C9	119.94 (14)	O4—C12—O3	120.85 (17)
C1—C2—C3	121.34 (16)	O4—C12—C13	128.17 (17)
C1—C2—H2	119.3	O3—C12—C13	110.98 (13)
C3—C2—H2	119.3	C12—C13—C14	109.88 (13)
C4—C3—C2	120.12 (15)	C12—C13—C10	103.87 (13)
C4—C3—H3	119.9	C14—C13—C10	116.31 (13)
C2—C3—H3	119.9	C12—C13—H13	108.8
O1—C4—C3	125.08 (15)	C14—C13—H13	108.8
O1—C4—C5	115.51 (16)	C10—C13—H13	108.8
C3—C4—C5	119.40 (16)	C15—C14—C13	112.45 (12)
O2—C5—C6	125.01 (14)	C15—C14—H14A	109.1
O2—C5—C4	114.90 (15)	C13—C14—H14A	109.1
C6—C5—C4	120.07 (15)	C15—C14—H14B	109.1
C5—C6—C1	121.14 (15)	C13—C14—H14B	109.1
C5—C6—H6	119.4	H14A—C14—H14B	107.8
C1—C6—H6	119.4	C16—C15—C20	118.66 (15)
O1—C7—H7A	109.5	C16—C15—C14	122.23 (15)
O1—C7—H7B	109.5	C20—C15—C14	119.10 (15)
H7A—C7—H7B	109.5	C15—C16—C17	120.90 (15)
O1—C7—H7C	109.5	C15—C16—H16	119.6
H7A—C7—H7C	109.5	C17—C16—H16	119.6
H7B—C7—H7C	109.5	C18—C17—C16	119.94 (15)
O2—C8—H8A	109.5	C18—C17—H17	120.0
O2—C8—H8B	109.5	C16—C17—H17	120.0
H8A—C8—H8B	109.5	O5—C18—C17	119.10 (15)
O2—C8—H8C	109.5	O5—C18—C19	121.42 (15)
H8A—C8—H8C	109.5	C17—C18—C19	119.46 (15)
H8B—C8—H8C	109.5	O6—C19—C20	125.01 (15)
C1—C9—C10	114.99 (13)	O6—C19—C18	114.57 (14)
C1—C9—H9A	108.5	C20—C19—C18	120.42 (15)
C10—C9—H9A	108.5	C19—C20—C15	120.55 (15)
C1—C9—H9B	108.5	C19—C20—H20	119.7
C10—C9—H9B	108.5	C15—C20—H20	119.7
H9A—C9—H9B	107.5	O6—C21—H21A	109.5
C11—C10—C13	102.73 (13)	O6—C21—H21B	109.5
C11—C10—C9	113.07 (13)	H21A—C21—H21B	109.5
C13—C10—C9	116.48 (13)	O6—C21—H21C	109.5
C11—C10—H10	108.1	H21A—C21—H21C	109.5
C13—C10—H10	108.1	H21B—C21—H21C	109.5

C6—C1—C2—C3	1.7 (2)	O3—C12—C13—C14	137.62 (14)
C9—C1—C2—C3	−176.52 (14)	O4—C12—C13—C10	−167.32 (18)
C1—C2—C3—C4	0.2 (2)	O3—C12—C13—C10	12.54 (18)
C7—O1—C4—C3	−11.9 (2)	C11—C10—C13—C12	−21.56 (16)
C7—O1—C4—C5	167.03 (16)	C9—C10—C13—C12	−145.71 (14)
C2—C3—C4—O1	177.18 (15)	C11—C10—C13—C14	−142.41 (14)
C2—C3—C4—C5	−1.7 (2)	C9—C10—C13—C14	93.44 (17)
C8—O2—C5—C6	1.7 (2)	C12—C13—C14—C15	−174.92 (14)
C8—O2—C5—C4	−176.99 (13)	C10—C13—C14—C15	−57.32 (19)
O1—C4—C5—O2	1.0 (2)	C13—C14—C15—C16	−85.45 (19)
C3—C4—C5—O2	179.99 (14)	C13—C14—C15—C20	93.00 (17)
O1—C4—C5—C6	−177.79 (13)	C20—C15—C16—C17	−1.9 (2)
C3—C4—C5—C6	1.2 (2)	C14—C15—C16—C17	176.52 (14)
O2—C5—C6—C1	−177.86 (14)	C15—C16—C17—C18	−0.4 (2)
C4—C5—C6—C1	0.8 (2)	C16—C17—C18—O5	−179.14 (13)
C2—C1—C6—C5	−2.2 (2)	C16—C17—C18—C19	2.5 (2)
C9—C1—C6—C5	176.05 (13)	C21—O6—C19—C20	−3.5 (2)
C2—C1—C9—C10	89.17 (18)	C21—O6—C19—C18	176.67 (15)
C6—C1—C9—C10	−89.02 (18)	O5—C18—C19—O6	−0.7 (2)
C1—C9—C10—C11	−63.25 (19)	C17—C18—C19—O6	177.63 (13)
C1—C9—C10—C13	55.42 (19)	O5—C18—C19—C20	179.43 (14)
C12—O3—C11—C10	−17.30 (19)	C17—C18—C19—C20	−2.2 (2)
C13—C10—C11—O3	23.87 (17)	O6—C19—C20—C15	−179.96 (14)
C9—C10—C11—O3	150.24 (14)	C18—C19—C20—C15	−0.1 (2)
C11—O3—C12—O4	−177.32 (17)	C16—C15—C20—C19	2.2 (2)
C11—O3—C12—C13	2.8 (2)	C14—C15—C20—C19	−176.31 (14)
O4—C12—C13—C14	−42.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.90 (2)	2.04 (2)	2.8280 (17)	146 (2)
O5—H5···O6	0.90 (2)	2.22 (2)	2.6799 (18)	111.7 (17)
O5—H5···O1ⁱ	0.90 (2)	2.58 (2)	3.2406 (18)	130.8 (16)
C3—H3···O5ⁱⁱ	0.95	2.34	3.278 (2)	168
C14—H14A···O4ⁱⁱⁱ	0.99	2.86	3.687 (2)	142
C14—H14B···O5^iv	0.99	2.42	3.373 (2)	162
C20—H20···O4ⁱⁱⁱ	0.95	2.53	3.446 (2)	162

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+2; (iv) x−1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄O₆
M_r	372.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	9.4845 (19), 10.065 (2), 19.915 (4)
V (Å³)	1901.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	13910, 2581, 2449
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.079, 1.06
No. of reflections	2581
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Selected torsion angles (º) top

C12—O3—C11—C10	−17.30 (19)	O3—C12—C13—C10	12.54 (18)
C13—C10—C11—O3	23.87 (17)	C11—C10—C13—C12	−21.56 (16)
C11—O3—C12—C13	2.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.90 (2)	2.04 (2)	2.8280 (17)	146 (2)
O5—H5···O6	0.90 (2)	2.22 (2)	2.6799 (18)	111.7 (17)
O5—H5···O1ⁱ	0.90 (2)	2.58 (2)	3.2406 (18)	130.8 (16)
C3—H3···O5ⁱⁱ	0.95	2.34	3.278 (2)	168
C14—H14A···O4ⁱⁱⁱ	0.99	2.86	3.687 (2)	142
C14—H14B···O5^iv	0.99	2.42	3.373 (2)	162
C20—H20···O4ⁱⁱⁱ	0.95	2.53	3.446 (2)	162

Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+2; (iv) x−1/2, −y+1/2, −z+2.

References

Awale, S., Lu, J., Kalaumi, S. K., Kurashima, Y., Tezuka, Y., Kadaota, S. & Esumi, H. (2006). Cancer Res. 66, 1751–1757. Web of Science CrossRef PubMed CAS Google Scholar
Bruno-Colmenárez, J., Usubillaga, A., Khouri, N. & Díaz de Delgado, G. (2007). Acta Cryst. E63, o2046–o2047. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1538

doi:10.1107/S1600536808021752

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