Dihydro­myricetin hexa­acetate

Li, W.; Bhadbhade, M.; Hook, J.; Zhao, J.

doi:10.1107/S1600536810037578

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2627

doi:10.1107/S1600536810037578

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Dihydromyricetin hexaacetate

Wei Li,^a Mohan Bhadbhade,^b James Hook ^b and Jian Zhao ^c ^*

^aCollege of Biological Engineering, Hubei University of Technology, Wuhan 430068, People's Republic of China, ^bMark Wainwright Analytical Centre, The University of New South Wales, Sydney, NSW 2052, Australia, and ^cSchool of Chemical Engineering, The University of New South Wales, Sydney, NSW 2052, Australia
^*Correspondence e-mail: jian.zhao@unsw.edu.au

(Received 6 August 2010; accepted 20 September 2010; online 25 September 2010)

In the title compound, C₂₇H₂₄O₁₄, also known as 2,3-diacetoxy-5-[(2RS,3RS)-3,5,7-triacetoxy-4-oxochromen-2-yl]phenyl acetate, the heterocyclic ring adopts a distorted half-chair conformation, with two C atoms displaced by 0.1775 (16) and −0.5950 (16) Å from the mean plane of the other four atoms. The dihedral angle between the aromatic rings is 57.81 (8)°. In the crystal, the molecules interact by C—H⋯O bonds, aromatic π–π stacking [centroid–centroid separation = 3.6206 (9) Å] and C—H⋯π interactions.

Related literature

For the crystal structure of dihydromyricetin, see: Xu et al. (2007 ). For the properties of dihydromyricetin, see: Li et al. (2006 ); Liu et al. (2009 ), Gao et al. (2009 ).

Experimental

Crystal data

C₂₇H₂₄O₁₄
M_r = 572.46
Triclinic, $[P \overline 1]$
a = 7.7979 (2) Å
b = 11.6652 (3) Å
c = 16.2083 (4) Å
α = 96.889 (1)°
β = 97.600 (1)°
γ = 109.085 (1)°
V = 1359.97 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 K
0.21 × 0.21 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.976, T_max = 0.989
16120 measured reflections
5856 independent reflections
4761 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.03
5856 reflections
377 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O6ⁱ	0.95	2.53	3.2847 (19)	136
C8—H8⋯O3ⁱ	1.00	2.33	3.2833 (18)	158
C11—H11A⋯O2ⁱⁱ	0.98	2.40	3.347 (2)	161
C13—H13A⋯O4ⁱⁱⁱ	0.98	2.44	3.417 (2)	176
C15—H15B⋯O4^iv	0.98	2.59	3.232 (2)	124
C23—H23B⋯Cg3^v	0.98	2.86	3.7598 (18)	153
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z; (iii) -x+2, -y+1, -z; (iv) x, y-1, z; (v) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037578/hb5603sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037578/hb5603Isup2.hkl

checkCIF report

Comment top

Dihydromyricetin is the principal flavonoid of Ampelopsis grossedentata, a vine which grows abundantly in southern China. The compound is a strong anti-oxidant with many reported health-promoting properties and, therefore, is emerging as a promising functional ingredient for use in a number of pharmaceutical and food applications (Li et al., 2006). However, the compound is poorly soluble in both water and fat, which limits its applications (Gao et al., 2009). Acetylation could be one way how to improve its lipid solubility. Although the single-crystal structure of dihydromyricetin itself is known (Xu et al., 2007), none of its derivatives have to date been structurally characterized. Herein we report the structure of the hexaacetate of dihydromyricetin (Fig. 1).

Though the title structure is of the biological origin, it crystallizes in a structure where both enantiomers are present. Fig. 1 shows the view of the (R, R) enantiomer. The torsion angle between the benzopyrone and the phenyl ring (O1—C8—C16—C17) is -36.2 (2)°. The crystal packing (Tab. 1, Fig. 2) contains a network of C—H···O interactions. Moreover, there are also present π-electron ring - π-electron ring interactions between the adjacent rings C1//C2//C3//C4//C5//C9 [symmetry code: 1-x,1-y, -z] as indicates the distance between the centroids that equals to 3.6206 (9)Å.

Related literature top

For the crystal structure of dihydromyricetin, see: Xu et al. (2007). For the properties of dihydromyricetin, see: Li et al. (2006); Liu et al. (2009), Gao et al. (2009).

Experimental top

The crystals of dihydromyricetin (1 g), prepared as described by Xu et al. (2007), were added by parts to a mixture of acetic anhydride (6 ml) and pyridine (1 ml) maintained at 75°C in the water bath. Each addition was done after the crystals of dihydromyricetin that had been added previously completely dissolved. The mixture was stirred for 30 min and upon addition of chilled water (120 ml), yielded an oily precipitate, which solidified in 15 min. After decanting the supernatant and washing the precipitate with water, the precipitate was collected and dried at 55°C for 24 h to afford a light yellow solid. A portion (50 mg) was dissolved in warm methanol, and yielded, on standing for several days at ambient temperature, colourless plates of (I) (m.p. 436 - 440 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

	Fig. 1. View of the (R,R) enantiomer of (I). The displacement ellipsoids shown at 50% probability level.
	Fig. 2. Packing of the molecules viewed down the a axis showing the C—H···O interactions.

2,3-diacetoxy-5-[(2RS,3RS)-3,5,7-triacetoxy- 4-oxochromen-2-yl]phenyl acetate top

Crystal data top

C₂₇H₂₄O₁₄	Z = 2
M_r = 572.46	F(000) = 596
Triclinic, P1	D_x = 1.398 Mg m⁻³
Hall symbol: -P 1	Melting point = 436–440 K
a = 7.7979 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6652 (3) Å	Cell parameters from 7407 reflections
c = 16.2083 (4) Å	θ = 2.5–30.4°
α = 96.889 (1)°	µ = 0.12 mm⁻¹
β = 97.600 (1)°	T = 150 K
γ = 109.085 (1)°	Plate, colourless
V = 1359.97 (6) Å³	0.21 × 0.21 × 0.09 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5856 independent reflections
Radiation source: fine-focus sealed tube	4761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ scans and ω scans with κ offsets	θ_max = 27.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.976, T_max = 0.989	k = −14→14
16120 measured reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0452P)² + 0.5506P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5856 reflections	Δρ_max = 0.30 e Å⁻³
377 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
90 constraints	Extinction coefficient: 0.0070 (16)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₇H₂₄O₁₄	γ = 109.085 (1)°
M_r = 572.46	V = 1359.97 (6) Å³
Triclinic, P1	Z = 2
a = 7.7979 (2) Å	Mo Kα radiation
b = 11.6652 (3) Å	µ = 0.12 mm⁻¹
c = 16.2083 (4) Å	T = 150 K
α = 96.889 (1)°	0.21 × 0.21 × 0.09 mm
β = 97.600 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5856 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4761 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.989	R_int = 0.041
16120 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
5856 reflections	Δρ_min = −0.32 e Å⁻³
377 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	0.72782 (15)	0.50439 (9)	0.17597 (6)	0.0248 (2)
O2	0.82930 (16)	0.23522 (10)	0.02789 (7)	0.0285 (3)
O3	0.69164 (15)	0.73102 (9)	−0.04552 (6)	0.0249 (2)
O4	0.88884 (16)	0.87775 (10)	0.06016 (7)	0.0332 (3)
O5	0.81318 (15)	0.36393 (9)	−0.10513 (6)	0.0243 (2)
O6	0.53693 (17)	0.21507 (11)	−0.11517 (8)	0.0395 (3)
O7	0.77402 (16)	0.20741 (10)	0.18599 (7)	0.0276 (3)
O8	1.0734 (2)	0.22913 (14)	0.20952 (9)	0.0503 (4)
O9	0.86595 (16)	0.57686 (10)	0.49672 (6)	0.0275 (3)
O10	0.84901 (17)	0.73527 (11)	0.43165 (7)	0.0320 (3)
O11	0.57423 (16)	0.40577 (11)	0.53218 (6)	0.0275 (3)
O12	0.7581 (2)	0.30683 (15)	0.57861 (8)	0.0540 (4)
O13	0.36896 (15)	0.19986 (10)	0.41469 (7)	0.0294 (3)
O14	0.50639 (19)	0.06354 (12)	0.37879 (10)	0.0475 (4)
C1	0.7183 (2)	0.61969 (13)	0.06911 (9)	0.0220 (3)
H1	0.6996	0.6799	0.1083	0.026*
C2	0.7256 (2)	0.63424 (13)	−0.01355 (9)	0.0206 (3)
C3	0.7503 (2)	0.54634 (13)	−0.07242 (9)	0.0213 (3)
H3	0.7523	0.5575	−0.1294	0.026*
C4	0.77163 (19)	0.44346 (13)	−0.04645 (9)	0.0200 (3)
C5	0.76921 (19)	0.42384 (13)	0.03763 (9)	0.0193 (3)
C6	0.8072 (2)	0.32072 (13)	0.07019 (9)	0.0210 (3)
C7	0.8197 (2)	0.32839 (14)	0.16601 (9)	0.0240 (3)
H7	0.9469	0.3811	0.1961	0.029*
C8	0.6793 (2)	0.38156 (13)	0.19367 (9)	0.0226 (3)
H8	0.5555	0.3313	0.1589	0.027*
C9	0.7390 (2)	0.51454 (13)	0.09333 (9)	0.0203 (3)
C10	0.7732 (2)	0.84986 (14)	−0.00181 (10)	0.0256 (3)
C11	0.6960 (3)	0.93267 (16)	−0.04461 (13)	0.0430 (5)
H11A	0.7555	1.0174	−0.0139	0.064*
H11B	0.5628	0.9064	−0.0454	0.064*
H11C	0.7187	0.9288	−0.1027	0.064*
C12	0.6877 (2)	0.24719 (15)	−0.13283 (10)	0.0281 (3)
C13	0.7670 (3)	0.17287 (17)	−0.18755 (11)	0.0388 (4)
H13A	0.8635	0.1541	−0.1526	0.058*
H13B	0.8201	0.2199	−0.2299	0.058*
H13C	0.6693	0.0959	−0.2161	0.058*
C14	0.9157 (3)	0.16750 (17)	0.20681 (10)	0.0327 (4)
C15	0.8447 (3)	0.04084 (18)	0.22644 (12)	0.0477 (5)
H15A	0.9488	0.0144	0.2444	0.072*
H15B	0.7653	−0.0158	0.1759	0.072*
H15C	0.7735	0.0405	0.2719	0.072*
C16	0.6647 (2)	0.38600 (14)	0.28534 (9)	0.0216 (3)
C17	0.7826 (2)	0.48387 (14)	0.34725 (9)	0.0227 (3)
H17	0.8803	0.5474	0.3329	0.027*
C18	0.7543 (2)	0.48648 (14)	0.42975 (9)	0.0226 (3)
C19	0.6149 (2)	0.39279 (14)	0.45148 (9)	0.0221 (3)
C20	0.5068 (2)	0.29293 (14)	0.39022 (10)	0.0231 (3)
C21	0.5276 (2)	0.29052 (14)	0.30684 (9)	0.0235 (3)
H21	0.4484	0.2239	0.2645	0.028*
C22	0.9069 (2)	0.69928 (14)	0.49122 (10)	0.0253 (3)
C23	1.0292 (2)	0.77456 (15)	0.57159 (10)	0.0307 (4)
H23A	1.0586	0.8623	0.5690	0.046*
H23B	1.1436	0.7560	0.5794	0.046*
H23C	0.9659	0.7549	0.6192	0.046*
C24	0.6593 (2)	0.36239 (15)	0.59285 (10)	0.0282 (3)
C25	0.6109 (3)	0.3970 (2)	0.67600 (11)	0.0462 (5)
H25A	0.4802	0.3516	0.6751	0.069*
H25B	0.6337	0.4857	0.6866	0.069*
H25C	0.6870	0.3765	0.7209	0.069*
C26	0.3857 (2)	0.08583 (15)	0.40763 (11)	0.0316 (4)
C27	0.2336 (3)	−0.00180 (19)	0.43981 (16)	0.0515 (5)
H27A	0.1167	−0.0205	0.4009	0.077*
H27B	0.2249	0.0355	0.4959	0.077*
H27C	0.2592	−0.0780	0.4438	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0379 (6)	0.0226 (5)	0.0161 (5)	0.0125 (5)	0.0074 (4)	0.0032 (4)
O2	0.0397 (7)	0.0246 (6)	0.0242 (6)	0.0152 (5)	0.0085 (5)	0.0015 (4)
O3	0.0302 (6)	0.0191 (5)	0.0229 (5)	0.0072 (5)	−0.0005 (4)	0.0036 (4)
O4	0.0340 (7)	0.0263 (6)	0.0326 (7)	0.0069 (5)	−0.0023 (5)	−0.0008 (5)
O5	0.0308 (6)	0.0244 (5)	0.0187 (5)	0.0108 (5)	0.0084 (4)	0.0007 (4)
O6	0.0308 (7)	0.0324 (7)	0.0467 (8)	0.0069 (5)	0.0025 (6)	−0.0089 (5)
O7	0.0357 (6)	0.0257 (6)	0.0263 (6)	0.0140 (5)	0.0094 (5)	0.0092 (4)
O8	0.0437 (9)	0.0627 (9)	0.0511 (9)	0.0285 (8)	0.0027 (7)	0.0131 (7)
O9	0.0353 (6)	0.0261 (6)	0.0176 (5)	0.0098 (5)	−0.0010 (4)	−0.0006 (4)
O10	0.0376 (7)	0.0310 (6)	0.0267 (6)	0.0121 (5)	0.0029 (5)	0.0047 (5)
O11	0.0372 (6)	0.0392 (6)	0.0167 (5)	0.0239 (5)	0.0100 (5)	0.0093 (4)
O12	0.0768 (11)	0.0851 (11)	0.0371 (7)	0.0652 (9)	0.0248 (7)	0.0286 (7)
O13	0.0290 (6)	0.0289 (6)	0.0343 (6)	0.0101 (5)	0.0145 (5)	0.0107 (5)
O14	0.0421 (8)	0.0320 (7)	0.0747 (10)	0.0152 (6)	0.0248 (7)	0.0116 (6)
C1	0.0232 (8)	0.0208 (7)	0.0206 (7)	0.0068 (6)	0.0041 (6)	0.0002 (6)
C2	0.0179 (7)	0.0176 (7)	0.0237 (7)	0.0033 (6)	0.0021 (6)	0.0041 (6)
C3	0.0203 (7)	0.0243 (7)	0.0167 (7)	0.0041 (6)	0.0035 (6)	0.0036 (6)
C4	0.0181 (7)	0.0198 (7)	0.0192 (7)	0.0038 (6)	0.0043 (5)	−0.0008 (5)
C5	0.0177 (7)	0.0198 (7)	0.0187 (7)	0.0044 (6)	0.0041 (5)	0.0021 (5)
C6	0.0191 (7)	0.0216 (7)	0.0212 (7)	0.0053 (6)	0.0049 (6)	0.0025 (6)
C7	0.0274 (8)	0.0230 (7)	0.0227 (8)	0.0096 (6)	0.0056 (6)	0.0049 (6)
C8	0.0266 (8)	0.0217 (7)	0.0180 (7)	0.0070 (6)	0.0042 (6)	0.0021 (6)
C9	0.0199 (7)	0.0215 (7)	0.0171 (7)	0.0049 (6)	0.0028 (5)	0.0015 (5)
C10	0.0258 (8)	0.0209 (7)	0.0280 (8)	0.0051 (6)	0.0059 (7)	0.0036 (6)
C11	0.0446 (11)	0.0235 (9)	0.0547 (12)	0.0092 (8)	−0.0057 (9)	0.0075 (8)
C12	0.0339 (9)	0.0277 (8)	0.0218 (8)	0.0137 (7)	−0.0016 (7)	0.0001 (6)
C13	0.0530 (12)	0.0361 (10)	0.0305 (9)	0.0241 (9)	0.0042 (8)	−0.0031 (7)
C14	0.0432 (11)	0.0413 (10)	0.0187 (8)	0.0229 (9)	0.0040 (7)	0.0033 (7)
C15	0.0823 (16)	0.0368 (10)	0.0304 (10)	0.0338 (11)	0.0007 (10)	0.0037 (8)
C16	0.0247 (8)	0.0247 (7)	0.0170 (7)	0.0109 (6)	0.0039 (6)	0.0032 (6)
C17	0.0236 (8)	0.0238 (7)	0.0210 (7)	0.0083 (6)	0.0044 (6)	0.0039 (6)
C18	0.0253 (8)	0.0247 (7)	0.0179 (7)	0.0113 (6)	0.0007 (6)	0.0006 (6)
C19	0.0284 (8)	0.0284 (8)	0.0166 (7)	0.0172 (7)	0.0068 (6)	0.0060 (6)
C20	0.0216 (7)	0.0255 (8)	0.0261 (8)	0.0110 (6)	0.0078 (6)	0.0075 (6)
C21	0.0245 (8)	0.0243 (7)	0.0204 (7)	0.0083 (6)	0.0025 (6)	0.0013 (6)
C22	0.0247 (8)	0.0284 (8)	0.0228 (8)	0.0089 (7)	0.0083 (6)	0.0015 (6)
C23	0.0298 (9)	0.0314 (9)	0.0264 (8)	0.0081 (7)	0.0035 (7)	−0.0023 (7)
C24	0.0311 (9)	0.0351 (9)	0.0240 (8)	0.0166 (7)	0.0064 (7)	0.0106 (7)
C25	0.0596 (13)	0.0746 (14)	0.0213 (9)	0.0421 (12)	0.0116 (8)	0.0148 (9)
C26	0.0300 (9)	0.0291 (9)	0.0346 (9)	0.0084 (7)	0.0059 (7)	0.0073 (7)
C27	0.0491 (12)	0.0397 (11)	0.0755 (15)	0.0144 (10)	0.0306 (11)	0.0288 (10)

Geometric parameters (Å, º) top

O1—C9	1.3704 (17)	C8—H8	1.0000
O1—C8	1.4322 (18)	C10—C11	1.486 (2)
O2—C6	1.2143 (17)	C11—H11A	0.9800
O3—C10	1.3773 (18)	C11—H11B	0.9800
O3—C2	1.3830 (17)	C11—H11C	0.9800
O4—C10	1.1911 (19)	C12—C13	1.494 (2)
O5—C12	1.3709 (19)	C13—H13A	0.9800
O5—C4	1.3916 (16)	C13—H13B	0.9800
O6—C12	1.196 (2)	C13—H13C	0.9800
O7—C14	1.351 (2)	C14—C15	1.488 (3)
O7—C7	1.4265 (18)	C15—H15A	0.9800
O8—C14	1.197 (2)	C15—H15B	0.9800
O9—C22	1.3743 (19)	C15—H15C	0.9800
O9—C18	1.3867 (18)	C16—C21	1.385 (2)
O10—C22	1.1910 (19)	C16—C17	1.397 (2)
O11—C24	1.3525 (19)	C17—C18	1.382 (2)
O11—C19	1.3886 (17)	C17—H17	0.9500
O12—C24	1.185 (2)	C18—C19	1.385 (2)
O13—C26	1.371 (2)	C19—C20	1.383 (2)
O13—C20	1.3941 (18)	C20—C21	1.380 (2)
O14—C26	1.191 (2)	C21—H21	0.9500
C1—C2	1.377 (2)	C22—C23	1.492 (2)
C1—C9	1.383 (2)	C23—H23A	0.9800
C1—H1	0.9500	C23—H23B	0.9800
C2—C3	1.394 (2)	C23—H23C	0.9800
C3—C4	1.370 (2)	C24—C25	1.492 (2)
C3—H3	0.9500	C25—H25A	0.9800
C4—C5	1.410 (2)	C25—H25B	0.9800
C5—C9	1.4072 (19)	C25—H25C	0.9800
C5—C6	1.469 (2)	C26—C27	1.491 (2)
C6—C7	1.533 (2)	C27—H27A	0.9800
C7—C8	1.514 (2)	C27—H27B	0.9800
C7—H7	1.0000	C27—H27C	0.9800
C8—C16	1.5013 (19)

C9—O1—C8	115.21 (11)	H13A—C13—H13C	109.5
C10—O3—C2	120.74 (12)	H13B—C13—H13C	109.5
C12—O5—C4	118.54 (12)	O8—C14—O7	122.91 (17)
C14—O7—C7	116.89 (13)	O8—C14—C15	127.04 (17)
C22—O9—C18	120.25 (12)	O7—C14—C15	110.04 (17)
C24—O11—C19	118.70 (12)	C14—C15—H15A	109.5
C26—O13—C20	116.82 (12)	C14—C15—H15B	109.5
C2—C1—C9	117.87 (13)	H15A—C15—H15B	109.5
C2—C1—H1	121.1	C14—C15—H15C	109.5
C9—C1—H1	121.1	H15A—C15—H15C	109.5
C1—C2—O3	122.15 (13)	H15B—C15—H15C	109.5
C1—C2—C3	122.11 (13)	C21—C16—C17	120.62 (13)
O3—C2—C3	115.47 (13)	C21—C16—C8	117.82 (13)
C4—C3—C2	118.70 (13)	C17—C16—C8	121.54 (14)
C4—C3—H3	120.6	C18—C17—C16	118.70 (14)
C2—C3—H3	120.6	C18—C17—H17	120.7
C3—C4—O5	116.72 (13)	C16—C17—H17	120.7
C3—C4—C5	122.16 (13)	C17—C18—C19	121.01 (14)
O5—C4—C5	120.86 (13)	C17—C18—O9	123.72 (14)
C9—C5—C4	116.26 (13)	C19—C18—O9	115.19 (13)
C9—C5—C6	119.47 (13)	C20—C19—C18	119.42 (13)
C4—C5—C6	124.15 (12)	C20—C19—O11	120.74 (14)
O2—C6—C5	125.38 (13)	C18—C19—O11	119.56 (13)
O2—C6—C7	120.45 (13)	C21—C20—C19	120.55 (14)
C5—C6—C7	114.16 (12)	C21—C20—O13	121.56 (14)
O7—C7—C8	107.60 (12)	C19—C20—O13	117.75 (13)
O7—C7—C6	109.39 (12)	C20—C21—C16	119.51 (14)
C8—C7—C6	108.99 (12)	C20—C21—H21	120.2
O7—C7—H7	110.3	C16—C21—H21	120.2
C8—C7—H7	110.3	O10—C22—O9	123.93 (14)
C6—C7—H7	110.3	O10—C22—C23	127.63 (15)
O1—C8—C16	108.45 (11)	O9—C22—C23	108.43 (13)
O1—C8—C7	107.80 (12)	C22—C23—H23A	109.5
C16—C8—C7	115.37 (12)	C22—C23—H23B	109.5
O1—C8—H8	108.3	H23A—C23—H23B	109.5
C16—C8—H8	108.3	C22—C23—H23C	109.5
C7—C8—H8	108.3	H23A—C23—H23C	109.5
O1—C9—C1	115.19 (12)	H23B—C23—H23C	109.5
O1—C9—C5	121.95 (13)	O12—C24—O11	122.55 (15)
C1—C9—C5	122.86 (13)	O12—C24—C25	127.56 (16)
O4—C10—O3	123.10 (14)	O11—C24—C25	109.88 (14)
O4—C10—C11	127.33 (15)	C24—C25—H25A	109.5
O3—C10—C11	109.57 (13)	C24—C25—H25B	109.5
C10—C11—H11A	109.5	H25A—C25—H25B	109.5
C10—C11—H11B	109.5	C24—C25—H25C	109.5
H11A—C11—H11B	109.5	H25A—C25—H25C	109.5
C10—C11—H11C	109.5	H25B—C25—H25C	109.5
H11A—C11—H11C	109.5	O14—C26—O13	122.89 (16)
H11B—C11—H11C	109.5	O14—C26—C27	126.64 (17)
O6—C12—O5	122.57 (14)	O13—C26—C27	110.47 (15)
O6—C12—C13	127.38 (16)	C26—C27—H27A	109.5
O5—C12—C13	110.04 (15)	C26—C27—H27B	109.5
C12—C13—H13A	109.5	H27A—C27—H27B	109.5
C12—C13—H13B	109.5	C26—C27—H27C	109.5
H13A—C13—H13B	109.5	H27A—C27—H27C	109.5
C12—C13—H13C	109.5	H27B—C27—H27C	109.5

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O6ⁱ	0.95	2.53	3.2847 (19)	136
C8—H8···O3ⁱ	1.00	2.33	3.2833 (18)	158
C11—H11A···O2ⁱⁱ	0.98	2.40	3.347 (2)	161
C13—H13A···O4ⁱⁱⁱ	0.98	2.44	3.417 (2)	176
C15—H15B···O4^iv	0.98	2.59	3.232 (2)	124
C23—H23B···Cg3^v	0.98	2.86	3.7598 (18)	153

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄O₁₄
M_r	572.46
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.7979 (2), 11.6652 (3), 16.2083 (4)
α, β, γ (°)	96.889 (1), 97.600 (1), 109.085 (1)
V (Å³)	1359.97 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.21 × 0.21 × 0.09

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.976, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	16120, 5856, 4761
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.03
No. of reflections	5856
No. of parameters	377
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O6ⁱ	0.95	2.53	3.2847 (19)	136
C8—H8···O3ⁱ	1.00	2.33	3.2833 (18)	158
C11—H11A···O2ⁱⁱ	0.98	2.40	3.347 (2)	161
C13—H13A···O4ⁱⁱⁱ	0.98	2.44	3.417 (2)	176
C15—H15B···O4^iv	0.98	2.59	3.232 (2)	124
C23—H23B···Cg3^v	0.98	2.86	3.7598 (18)	153

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

Acknowledgements

WL is the recipient of an Endeavour Postdoctoral Fellowship of the Australian Government. This work was partly supported by the Hubei Bureau of Education Key Projects (D20091401), the Hubei Province Natural Science Foundation (2008CDZ001) and the Hubei University of Technology Key Researchers Start-up Fund (BSQD0814).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, USA. Google Scholar
Gao, J., Liu, B., Ning, Z., Zhao, R., Zhang, A. & Wu, Q. (2009). J. Food Biochem. 33, 808–820. Web of Science CrossRef CAS Google Scholar
Li, Y., Tan, Z., Li, T., Xiao, B. & Dai, Q. (2006). Acta Nutr. Sin. 28, 506–509. CAS Google Scholar
Liu, B., Du, J., Zeng, J., Chen, C. & Niu, S. (2009). Eur. Food Res. Technol. 230, 325–331. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, Z., Liu, B., Ning, Z. & Zhang, Y. (2007). Acta Cryst. E63, o4384. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2627

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