2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxy­cinnamo­yl)-β-d-glucopyran­ose

Liu, Y.-Y.; Liu, S.; Chu, Q.-Y.; Zhu, H.-J.

doi:10.1107/S1600536808004698

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o616

doi:10.1107/S1600536808004698

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2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-β-D-glucopyranose

Yuan-Yuan Liu,^a Shan Liu,^a Qing-Yan Chu ^a and Hong-Jun Zhu ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 22 January 2008; accepted 18 February 2008; online 22 February 2008)

Molecules of the title compound, C₂₄H₂₈O₁₂, are linked by intermolecular C—H⋯O hydrogen bonds. Bond lengths and angles are normal.

Related literature

For related literature, see: Loganathan & Trivedi (1987 ); Yu et al. (1991 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₂₈O₁₂
M_r = 508.46
Monoclinic, P 2₁
a = 9.972 (2) Å
b = 6.0580 (12) Å
c = 21.680 (4) Å
β = 97.19 (3)°
V = 1299.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.40 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.959, T_max = 0.990
2955 measured reflections
2790 independent reflections
1578 reflections with I > 2σ(I)
R_int = 0.062
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.189
S = 1.02
2790 reflections
319 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3ⁱ	0.96	2.45	3.164 (12)	131
C10—H10A⋯O5ⁱⁱ	0.98	2.48	3.423 (9)	160
C13—H13A⋯O11ⁱⁱⁱ	0.98	2.55	3.371 (8)	142
C24—H24A⋯O8^iv	0.96	2.51	3.457 (10)	171
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) x, y+1, z; (iii) x, y-1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004698/ez2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004698/ez2118Isup2.hkl

checkCIF report

Comment top

1-O-(p-methoxycinnamoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose is a type of glycolipid derivative (Loganathan et al., 1987) that plays an important role in medical applications, such as anti-tumor and antibacterial applications. We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal, molecules are linked to each other to form a three dimensional framework via intermolecular C—H···O hydrogen bonds.

Related literature top

For related literature, see: Loganathan & Trivedi (1987); Yu et al. (1991). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I), was prepared by a method similar to that reported previously (Yu et al., 1991). The crystals were obtained by dissolving compound I (1.5 g) in methanol (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines.

2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-β-D-glucopyranose top

Crystal data top

C₂₄H₂₈O₁₂	F(000) = 536
M_r = 508.46	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.972 (2) Å	θ = 9–12°
b = 6.0580 (12) Å	µ = 0.11 mm⁻¹
c = 21.680 (4) Å	T = 298 K
β = 97.19 (3)°	Needle, colourless
V = 1299.4 (4) Å³	0.40 × 0.10 × 0.10 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.959, T_max = 0.990	l = 0→26
2955 measured reflections	3 standard reflections every 200 reflections
2790 independent reflections	intensity decay: none

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.09P)²] where P = (F_o² + 2F_c²)/3
2790 reflections	(Δ/σ)_max < 0.001
319 parameters	Δρ_max = 0.43 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₄H₂₈O₁₂	V = 1299.4 (4) Å³
M_r = 508.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.972 (2) Å	µ = 0.11 mm⁻¹
b = 6.0580 (12) Å	T = 298 K
c = 21.680 (4) Å	0.40 × 0.10 × 0.10 mm
β = 97.19 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1578 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.062
T_min = 0.959, T_max = 0.990	3 standard reflections every 200 reflections
2955 measured reflections	intensity decay: none
2790 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	1 restraint
wR(F²) = 0.189	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
2790 reflections	Δρ_min = −0.40 e Å⁻³
319 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	0.5843 (6)	0.1875 (12)	0.2849 (3)	0.089
C1	0.6777 (7)	0.468 (2)	0.3547 (4)	0.099 (3)
H1A	0.7643	0.4270	0.3433	0.148*
H1B	0.6804	0.4617	0.3990	0.148*
H1C	0.6559	0.6153	0.3405	0.148*
O2	0.4512 (4)	0.3681 (9)	0.3422 (2)	0.0591 (13)
C2	0.5738 (7)	0.3138 (18)	0.3256 (4)	0.084 (3)
O3	0.2760 (6)	0.0744 (11)	0.4807 (2)	0.0799 (17)
C3	0.3974 (9)	−0.2530 (17)	0.4674 (4)	0.090 (3)
H3A	0.3975	−0.2727	0.5113	0.135*
H3B	0.4888	−0.2445	0.4580	0.135*
H3C	0.3526	−0.3758	0.4457	0.135*
O4	0.3228 (5)	−0.0182 (9)	0.38543 (19)	0.0567 (12)
C4	0.3267 (7)	−0.0507 (14)	0.4480 (3)	0.0567 (18)
O5	0.0717 (7)	−0.2870 (10)	0.3886 (3)	0.0846 (18)
C5	−0.0937 (9)	−0.123 (2)	0.4448 (4)	0.116 (4)
H5A	−0.1026	−0.2675	0.4619	0.174*
H5B	−0.1795	−0.0758	0.4239	0.174*
H5C	−0.0641	−0.0212	0.4776	0.174*
O6	0.0213 (4)	0.0758 (8)	0.3744 (2)	0.0512 (12)
C6	0.0086 (8)	−0.1292 (15)	0.3991 (3)	0.061 (2)
O7	−0.1160 (7)	−0.2286 (11)	0.2512 (3)	0.095 (2)
C7	−0.0606 (8)	−0.2633 (14)	0.1464 (3)	0.070 (2)
H7A	−0.0739	−0.4181	0.1528	0.106*
H7B	0.0305	−0.2382	0.1381	0.106*
H7C	−0.1224	−0.2137	0.1116	0.106*
O8	−0.0694 (5)	0.0730 (8)	0.1983 (2)	0.0547 (12)
C8	−0.0852 (7)	−0.1400 (14)	0.2026 (4)	0.0600 (19)
O9	0.1321 (4)	0.3455 (8)	0.24191 (19)	0.0492 (11)
C9	−0.0883 (6)	0.2144 (13)	0.2493 (3)	0.0539 (18)
H9A	−0.1431	0.1388	0.2767	0.065*
H9B	−0.1368	0.3458	0.2337	0.065*
O10	0.3339 (4)	0.4790 (8)	0.2226 (2)	0.0546 (12)
C10	0.0445 (6)	0.2813 (12)	0.2859 (3)	0.0521 (18)
H10A	0.0288	0.4098	0.3115	0.062*
C11	0.1097 (6)	0.1011 (11)	0.3280 (3)	0.0482 (17)
H11A	0.1150	−0.0366	0.3047	0.058*
O11	0.2593 (5)	0.8310 (8)	0.2125 (2)	0.0652 (14)
O12	0.8530 (5)	0.5383 (9)	−0.0491 (2)	0.0678 (15)
C12	0.2491 (6)	0.1706 (11)	0.3578 (3)	0.0436 (15)
H12A	0.2408	0.2826	0.3897	0.052*
C13	0.3322 (6)	0.2602 (11)	0.3099 (3)	0.0455 (16)
H13A	0.3588	0.1408	0.2835	0.055*
C14	0.2546 (6)	0.4380 (12)	0.2704 (3)	0.0523 (18)
H14A	0.2400	0.5710	0.2944	0.063*
C15	0.3289 (7)	0.6851 (15)	0.1968 (3)	0.058 (2)
C16	0.4170 (7)	0.7047 (14)	0.1476 (3)	0.0594 (19)
H16A	0.4147	0.8349	0.1248	0.071*
C17	0.4991 (7)	0.5466 (15)	0.1343 (3)	0.062 (2)
H17A	0.4999	0.4189	0.1582	0.074*
C18	0.5902 (6)	0.5500 (11)	0.0855 (3)	0.0448 (15)
C19	0.6731 (7)	0.3730 (13)	0.0785 (3)	0.0558 (18)
H19A	0.6720	0.2524	0.1049	0.067*
C20	0.7586 (6)	0.3706 (13)	0.0325 (3)	0.0527 (17)
H20A	0.8118	0.2474	0.0275	0.063*
C21	0.7641 (6)	0.5531 (13)	−0.0059 (3)	0.0499 (17)
C22	0.6811 (6)	0.7313 (13)	0.0001 (3)	0.0547 (18)
H22A	0.6826	0.8520	−0.0263	0.066*
C23	0.5952 (6)	0.7300 (13)	0.0457 (3)	0.0534 (18)
H23A	0.5399	0.8513	0.0498	0.064*
C24	0.8593 (8)	0.7190 (19)	−0.0897 (4)	0.088 (3)
H24A	0.9251	0.6896	−0.1174	0.132*
H24B	0.8848	0.8495	−0.0659	0.132*
H24C	0.7723	0.7410	−0.1134	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.089	0.089	0.089	0.000	0.011	0.000
C1	0.062 (5)	0.131 (8)	0.109 (7)	−0.030 (6)	0.033 (5)	−0.042 (7)
O2	0.049 (3)	0.071 (3)	0.061 (3)	−0.011 (3)	0.019 (2)	−0.012 (3)
C2	0.051 (4)	0.126 (8)	0.079 (5)	−0.008 (5)	0.027 (4)	−0.054 (6)
O3	0.088 (4)	0.104 (5)	0.049 (3)	0.037 (4)	0.014 (3)	−0.006 (3)
C3	0.113 (7)	0.090 (7)	0.066 (5)	0.025 (7)	0.006 (5)	−0.001 (5)
O4	0.067 (3)	0.060 (3)	0.046 (3)	0.009 (3)	0.017 (2)	−0.005 (3)
C4	0.055 (4)	0.060 (5)	0.055 (4)	0.001 (4)	0.007 (3)	−0.009 (4)
O5	0.119 (5)	0.050 (4)	0.086 (4)	−0.014 (4)	0.016 (3)	0.008 (3)
C5	0.118 (8)	0.143 (10)	0.095 (7)	−0.048 (8)	0.050 (6)	0.023 (7)
O6	0.051 (3)	0.052 (3)	0.054 (3)	−0.008 (2)	0.021 (2)	−0.010 (2)
C6	0.075 (5)	0.052 (5)	0.058 (4)	−0.030 (5)	0.011 (4)	0.001 (4)
O7	0.132 (5)	0.074 (4)	0.084 (4)	−0.025 (4)	0.033 (4)	0.005 (4)
C7	0.077 (5)	0.069 (6)	0.061 (4)	−0.003 (5)	−0.006 (4)	−0.010 (5)
O8	0.056 (3)	0.046 (3)	0.061 (3)	−0.005 (2)	0.004 (2)	0.000 (3)
C8	0.052 (4)	0.059 (5)	0.068 (5)	0.002 (4)	0.003 (4)	−0.005 (5)
O9	0.044 (2)	0.049 (3)	0.058 (3)	−0.005 (2)	0.020 (2)	0.009 (2)
C9	0.042 (4)	0.051 (4)	0.070 (5)	0.000 (4)	0.011 (3)	0.000 (4)
O10	0.060 (3)	0.042 (2)	0.069 (3)	−0.009 (2)	0.038 (2)	0.006 (3)
C10	0.046 (4)	0.058 (5)	0.057 (4)	−0.002 (3)	0.023 (3)	0.001 (4)
C11	0.054 (4)	0.042 (4)	0.054 (4)	0.001 (3)	0.029 (3)	0.000 (3)
O11	0.086 (4)	0.044 (3)	0.073 (3)	0.012 (3)	0.037 (3)	−0.003 (3)
O12	0.073 (3)	0.074 (4)	0.063 (3)	0.023 (3)	0.033 (3)	0.015 (3)
C12	0.050 (4)	0.033 (3)	0.048 (3)	0.002 (3)	0.010 (3)	−0.005 (3)
C13	0.048 (4)	0.043 (4)	0.046 (3)	−0.006 (3)	0.012 (3)	−0.011 (3)
C14	0.054 (4)	0.047 (4)	0.061 (4)	−0.011 (3)	0.028 (3)	−0.021 (4)
C15	0.049 (4)	0.073 (5)	0.056 (4)	−0.018 (4)	0.026 (3)	−0.010 (4)
C16	0.061 (4)	0.063 (5)	0.059 (4)	−0.016 (4)	0.025 (3)	0.002 (4)
C17	0.052 (4)	0.089 (6)	0.047 (4)	0.001 (4)	0.013 (3)	0.005 (4)
C18	0.042 (3)	0.049 (4)	0.045 (3)	−0.006 (3)	0.012 (3)	0.002 (3)
C19	0.055 (4)	0.060 (5)	0.051 (4)	−0.006 (4)	0.003 (3)	0.003 (4)
C20	0.048 (4)	0.058 (4)	0.053 (4)	0.004 (4)	0.013 (3)	−0.004 (4)
C21	0.044 (3)	0.062 (4)	0.045 (4)	0.002 (4)	0.012 (3)	−0.005 (4)
C22	0.059 (4)	0.053 (4)	0.054 (4)	0.002 (4)	0.016 (3)	0.010 (4)
C23	0.043 (4)	0.066 (5)	0.054 (4)	0.001 (4)	0.015 (3)	0.001 (4)
C24	0.083 (5)	0.127 (8)	0.064 (5)	−0.001 (7)	0.048 (4)	−0.002 (6)

Geometric parameters (Å, º) top

O1—C2	1.183 (9)	O10—C15	1.366 (9)
C1—C2	1.475 (12)	O10—C14	1.403 (7)
C1—H1A	0.9600	C10—C11	1.516 (9)
C1—H1B	0.9600	C10—H10A	0.9800
C1—H1C	0.9600	C11—C12	1.518 (9)
O2—C2	1.358 (8)	C11—H11A	0.9800
O2—C13	1.456 (7)	O11—C15	1.199 (8)
O3—C4	1.193 (8)	O12—C21	1.372 (7)
C3—C4	1.450 (12)	O12—C24	1.411 (11)
C3—H3A	0.9600	C12—C13	1.509 (8)
C3—H3B	0.9600	C12—H12A	0.9800
C3—H3C	0.9600	C13—C14	1.525 (9)
O4—C4	1.367 (8)	C13—H13A	0.9800
O4—C12	1.448 (8)	C14—H14A	0.9800
O5—C6	1.182 (10)	C15—C16	1.469 (8)
C5—C6	1.509 (10)	C16—C17	1.315 (10)
C5—H5A	0.9600	C16—H16A	0.9300
C5—H5B	0.9600	C17—C18	1.479 (8)
C5—H5C	0.9600	C17—H17A	0.9300
O6—C6	1.365 (9)	C18—C19	1.375 (9)
O6—C11	1.425 (7)	C18—C23	1.396 (9)
O7—C8	1.253 (9)	C19—C20	1.390 (8)
C7—C8	1.477 (10)	C19—H19A	0.9300
C7—H7A	0.9600	C20—C21	1.389 (10)
C7—H7B	0.9600	C20—H20A	0.9300
C7—H7C	0.9600	C21—C22	1.376 (9)
O8—C8	1.305 (9)	C22—C23	1.386 (8)
O8—C9	1.431 (8)	C22—H22A	0.9300
O9—C14	1.413 (7)	C23—H23A	0.9300
O9—C10	1.426 (7)	C24—H24A	0.9600
C9—C10	1.512 (9)	C24—H24B	0.9600
C9—H9A	0.9700	C24—H24C	0.9600
C9—H9B	0.9700

C2—C1—H1A	109.5	C10—C11—C12	110.9 (5)
C2—C1—H1B	109.5	O6—C11—H11A	110.5
H1A—C1—H1B	109.5	C10—C11—H11A	110.5
C2—C1—H1C	109.5	C12—C11—H11A	110.5
H1A—C1—H1C	109.5	C21—O12—C24	117.3 (6)
H1B—C1—H1C	109.5	O4—C12—C13	106.0 (5)
C2—O2—C13	118.1 (5)	O4—C12—C11	110.3 (5)
O1—C2—O2	121.4 (7)	C13—C12—C11	111.0 (5)
O1—C2—C1	127.2 (7)	O4—C12—H12A	109.8
O2—C2—C1	109.9 (7)	C13—C12—H12A	109.8
C4—C3—H3A	109.5	C11—C12—H12A	109.8
C4—C3—H3B	109.5	O2—C13—C12	108.3 (5)
H3A—C3—H3B	109.5	O2—C13—C14	106.2 (5)
C4—C3—H3C	109.5	C12—C13—C14	110.9 (5)
H3A—C3—H3C	109.5	O2—C13—H13A	110.4
H3B—C3—H3C	109.5	C12—C13—H13A	110.4
C4—O4—C12	118.3 (5)	C14—C13—H13A	110.4
O3—C4—O4	122.5 (7)	O10—C14—O9	106.4 (5)
O3—C4—C3	126.3 (7)	O10—C14—C13	104.3 (5)
O4—C4—C3	111.2 (7)	O9—C14—C13	108.4 (5)
C6—C5—H5A	109.5	O10—C14—H14A	112.4
C6—C5—H5B	109.5	O9—C14—H14A	112.4
H5A—C5—H5B	109.5	C13—C14—H14A	112.4
C6—C5—H5C	109.5	O11—C15—O10	123.4 (5)
H5A—C5—H5C	109.5	O11—C15—C16	124.5 (7)
H5B—C5—H5C	109.5	O10—C15—C16	112.1 (7)
C6—O6—C11	118.1 (5)	C17—C16—C15	123.1 (7)
O5—C6—O6	125.7 (6)	C17—C16—H16A	118.5
O5—C6—C5	124.5 (9)	C15—C16—H16A	118.5
O6—C6—C5	109.8 (8)	C16—C17—C18	127.0 (7)
C8—C7—H7A	109.5	C16—C17—H17A	116.5
C8—C7—H7B	109.5	C18—C17—H17A	116.5
H7A—C7—H7B	109.5	C19—C18—C23	118.2 (6)
C8—C7—H7C	109.5	C19—C18—C17	120.1 (7)
H7A—C7—H7C	109.5	C23—C18—C17	121.8 (6)
H7B—C7—H7C	109.5	C18—C19—C20	121.3 (7)
C8—O8—C9	120.5 (6)	C18—C19—H19A	119.4
O7—C8—O8	121.9 (7)	C20—C19—H19A	119.4
O7—C8—C7	124.1 (8)	C19—C20—C21	119.6 (7)
O8—C8—C7	113.9 (7)	C19—C20—H20A	120.2
C14—O9—C10	112.6 (5)	C21—C20—H20A	120.2
O8—C9—C10	112.0 (5)	O12—C21—C22	124.3 (6)
O8—C9—H9A	109.2	O12—C21—C20	115.7 (6)
C10—C9—H9A	109.2	C22—C21—C20	119.9 (6)
O8—C9—H9B	109.2	C21—C22—C23	119.7 (7)
C10—C9—H9B	109.2	C21—C22—H22A	120.2
H9A—C9—H9B	107.9	C23—C22—H22A	120.2
C15—O10—C14	117.9 (5)	C22—C23—C18	121.3 (7)
O9—C10—C9	107.0 (5)	C22—C23—H23A	119.4
O9—C10—C11	110.3 (5)	C18—C23—H23A	119.4
C9—C10—C11	113.8 (6)	O12—C24—H24A	109.5
O9—C10—H10A	108.5	O12—C24—H24B	109.5
C9—C10—H10A	108.5	H24A—C24—H24B	109.5
C11—C10—H10A	108.5	O12—C24—H24C	109.5
O6—C11—C10	104.2 (5)	H24A—C24—H24C	109.5
O6—C11—C12	110.1 (5)	H24B—C24—H24C	109.5

C13—O2—C2—O1	2.2 (13)	O4—C12—C13—C14	171.1 (5)
C13—O2—C2—C1	169.5 (7)	C11—C12—C13—C14	51.3 (7)
C12—O4—C4—O3	−2.7 (10)	C15—O10—C14—O9	94.4 (7)
C12—O4—C4—C3	176.6 (6)	C15—O10—C14—C13	−151.1 (5)
C11—O6—C6—O5	5.5 (11)	C10—O9—C14—O10	176.0 (5)
C11—O6—C6—C5	−177.4 (6)	C10—O9—C14—C13	64.4 (6)
C9—O8—C8—O7	−0.6 (11)	O2—C13—C14—O10	71.6 (5)
C9—O8—C8—C7	−179.3 (5)	C12—C13—C14—O10	−170.9 (5)
C8—O8—C9—C10	100.3 (8)	O2—C13—C14—O9	−175.3 (4)
C14—O9—C10—C9	172.6 (6)	C12—C13—C14—O9	−57.8 (6)
C14—O9—C10—C11	−63.1 (7)	C14—O10—C15—O11	−0.9 (10)
O8—C9—C10—O9	46.1 (8)	C14—O10—C15—C16	179.8 (6)
O8—C9—C10—C11	−76.0 (7)	O11—C15—C16—C17	175.3 (7)
C6—O6—C11—C10	147.6 (6)	O10—C15—C16—C17	−5.5 (10)
C6—O6—C11—C12	−93.3 (7)	C15—C16—C17—C18	179.4 (7)
O9—C10—C11—O6	172.1 (5)	C16—C17—C18—C19	178.2 (7)
C9—C10—C11—O6	−67.7 (7)	C16—C17—C18—C23	−1.7 (11)
O9—C10—C11—C12	53.6 (7)	C23—C18—C19—C20	−0.8 (10)
C9—C10—C11—C12	173.9 (5)	C17—C18—C19—C20	179.2 (6)
C4—O4—C12—C13	140.7 (6)	C18—C19—C20—C21	2.1 (10)
C4—O4—C12—C11	−99.0 (6)	C24—O12—C21—C22	0.3 (10)
O6—C11—C12—O4	78.9 (6)	C24—O12—C21—C20	178.8 (7)
C10—C11—C12—O4	−166.2 (5)	C19—C20—C21—O12	178.8 (6)
O6—C11—C12—C13	−163.9 (5)	C19—C20—C21—C22	−2.7 (10)
C10—C11—C12—C13	−49.0 (7)	O12—C21—C22—C23	−179.7 (6)
C2—O2—C13—C12	129.9 (7)	C20—C21—C22—C23	1.9 (10)
C2—O2—C13—C14	−110.9 (7)	C21—C22—C23—C18	−0.6 (10)
O4—C12—C13—O2	−72.7 (6)	C19—C18—C23—C22	0.1 (10)
C11—C12—C13—O2	167.5 (5)	C17—C18—C23—C22	180.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.96	2.45	3.164 (12)	131
C10—H10A···O5ⁱⁱ	0.98	2.48	3.423 (9)	160
C13—H13A···O11ⁱⁱⁱ	0.98	2.55	3.371 (8)	142
C24—H24A···O8^iv	0.96	2.51	3.457 (10)	171

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈O₁₂
M_r	508.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	9.972 (2), 6.0580 (12), 21.680 (4)
β (°)	97.19 (3)
V (Å³)	1299.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.959, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2955, 2790, 1578
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.189, 1.02
No. of reflections	2790
No. of parameters	319
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.40

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3ⁱ	0.9600	2.4500	3.164 (12)	131.00
C10—H10A···O5ⁱⁱ	0.9800	2.4800	3.423 (9)	160.00
C13—H13A···O11ⁱⁱⁱ	0.9800	2.5500	3.371 (8)	142.00
C24—H24A···O8^iv	0.9600	2.5100	3.457 (10)	171.00

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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