3,5-Di-O-benzoyl-1,2-O-isopropyl­idene-α-d-ribo-hexos-3-ulo-1,4:3,6-difuran­ose

Zhang, Q.; Chen, X.; Zhu, N.; Jiang, T.; Liu, H.

doi:10.1107/S1600536811024317

3,5-Di-O-benzoyl-1,2-O-isopropylidene-α-D-ribo-hexos-3-ulo-1,4:3,6-difuranose

Q. Zhang, X. Chen, N. Zhu, T. Jiang and H. Liu

The title compound, C₂₃H₂₂O₈, is a binary benzoyl ester whose nucleus consists of a fused system made up of a methylenedioxy ring and two tetrahydrofuran rings. One of the benzoyl ester groups is attached at the junction of the two tetrahydrofuran rings. The other is attached to the outer tetrafuran ring. Both the benzoyl ester groups are in an axial conformation with respect to the outer tetrhydrofuran ring. In the crystal, molecules are linked by two weak C—H

O hydrogen bonds, forming a chain running parallel to the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811024317/lw2067sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811024317/lw2067Isup2.hkl Contains datablock I

CCDC reference: 827958

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R factor = 0.036
wR factor = 0.094
Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          4
PLAT920_ALERT_1_C Theta(Max)  in CIF and FCF Differ by ...........       0.14 Deg.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           72.26
           From the CIF: _reflns_number_total               2421
           Count of symmetry unique reflns         2421
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_4_G Note: The Model has Chirality at C1     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C2     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C3     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C4     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C5     (Verify)          R

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

C₂₃H₂₂O₈, (I), is an important intermediate in the synthesis of bicyclo-glycosyls (Zhang et al., 2011), whose nucleoside derivatives play a vital role as anti-tumour and antivirus agents have been synthesised (Xavier et al. 2009; Rajwanshi et al. 1999).

The nucleus of molecule (I),Figure 1, consists of three fused rings, a methylenedioxy ring which is linked to two fused tetrahydrofuran rings. The methylenedioxy ring and a tetrahydrofuran ring are oriented in opposite directions with respect to the central tetrahydrofuran. One of the benzoyl ester groups is attached at the junction of the two tetrahydrofuran rings. The other is attached to the outer tetrafuran ring. Both the benzoyl ester groups are in an axial conformation with respect to the outer tetrhydrofuran ring.

The molecules are linked by two weak C-H···O hydrogen bonds, Table 1, to form a chain which runs parallel to the a-axis, Figure 2.

Related literature top

For details of the synthesis of the nucleus, see: Tronchet & Bourgeois (1971). For applications of the nucleus, see: Xavier et al. (2009); Rajwanshi et al. (1999). For structure of a bicyclo-glcosyl compound, see: Zhang et al. (2011).

Experimental top

The title compound (I) was synthesized from 1,2;5,6-di-O-isopropylidene-α- D-ribo-hexofuranosid-3-ulose as described previously by Tronchet, (Tronchet & Bourgeois, 1971), whose starting material was D-glucose. A solution of 1,2;5,6-di-O-isopropylidene-α- D-ribo-hexofuranosid-3-ulose (1.01 g, 3.87 mmol) in aq. AcOH (60%,15 ml) was stirred at room temperature overnight. The solvent was co-evaporated with toluene and the residue was purified by column chromatography (EtOAc) to pruduce the difuranose compound 1,2-O-Isopropylidene-α-D-ribo-hexos-3-ulo-1,4:3,6-difuranose(0.79 g). Benzoyl chloride (0.05 ml,9 mmol) was then added to a solution of this difuranose compound in dry pyridine (3 ml). This solution was stirred at room temperature for 2 h. Water (10 ml) was added to the solution, and the mixture was extracted with EtOAc. The combined organic layers were washed with water and dried with anhydrous Na₂SO₄. After filtration and evaporation of the solvent, the residue was recrystallised in EtOAc to obtain the title compound as white solid. Crystals suitable for X-ray analysis were grown by slow evaporation from acetone at room temperature for two weeks. mp: 459-460K; R_f = 0.35 (petroleum ether/EtOAc, 5:1); ¹H NMR (400 MHz, CDCl₃) σ: 8.10(4H, m), 7.62(m, 2H), 7.49(m, 4H), 6.06(1H, d, J=3.8 Hz), 5.68(1H, dd, J=6.1 Hz), 5.23(1H, d, J=3.8 Hz), 5.12(1H, d, J=4.7,6.0 Hz), 4.58(1H, dd, J=9.4,7.0 Hz), 4.27(1H, dd, J=9.4,6.0 Hz), 1.52(3H, s), 1.37 (3H, s). ¹³C NMR (100 MHz, CDCl₃) σ: 165.9, 164.4, 133.6, 133.5, 130.0, 129.9, 129.5, 129.1, 128.5, 128.5, 113.8, 113.2, 107.4, 82.9, 81.8, 72.6, 72.2, 27.2, 27.2.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. H atoms omitted clarity.
	Fig. 2. Stereoview of the chain formed by C-H···O hydrogen bonds. Hydrogen atoms not involved in the motifs are not included.

3,5-Di-O-benzoyl-1,2-O-isopropylidene- α-D-ribo-hexos-3-ulo-1,4:3,6-difuranose top

Crystal data top

C₂₃H₂₂O₈	D_x = 1.367 Mg m⁻³
M_r = 426.41	Melting point = 459–460 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.5418 Å
a = 6.05837 (10) Å	Cell parameters from 5890 reflections
b = 8.33827 (14) Å	θ = 3.2–72.3°
c = 40.9992 (7) Å	µ = 0.87 mm⁻¹
V = 2071.13 (6) Å³	T = 291 K
Z = 4	Prism, colourless
F(000) = 896	0.30 × 0.30 × 0.25 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	2421 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2335 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 16.2312 pixels mm^-1	θ_max = 72.3°, θ_min = 4.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
T_min = 0.780, T_max = 0.812	l = −21→50
10556 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0643P)² + 0.1182P] where P = (F_o² + 2F_c²)/3
2421 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₃H₂₂O₈	V = 2071.13 (6) Å³
M_r = 426.41	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.05837 (10) Å	µ = 0.87 mm⁻¹
b = 8.33827 (14) Å	T = 291 K
c = 40.9992 (7) Å	0.30 × 0.30 × 0.25 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	2421 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2335 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.812	R_int = 0.026
10556 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
2421 reflections	Δρ_min = −0.26 e Å⁻³
282 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.7379 (3)	1.23548 (17)	0.88731 (3)	0.0556 (4)
O2	0.8454 (3)	1.07286 (15)	0.84526 (3)	0.0553 (4)
O3	0.7285 (2)	0.70109 (16)	0.88507 (3)	0.0458 (3)
O4	0.4603 (2)	1.04625 (17)	0.88971 (3)	0.0460 (3)
O5	0.4346 (2)	0.82295 (17)	0.93608 (3)	0.0462 (3)
O6	0.1023 (3)	0.9393 (3)	0.94092 (4)	0.0694 (5)
O7	0.6458 (2)	0.78758 (16)	0.83253 (3)	0.0396 (3)
O8	1.0139 (2)	0.75343 (19)	0.82694 (3)	0.0477 (3)
C1	0.6881 (4)	1.0796 (2)	0.89615 (4)	0.0436 (4)
H1	0.7261	1.0586	0.9190	0.052*
C2	0.8210 (3)	0.9737 (2)	0.87294 (4)	0.0388 (3)
H2	0.9629	0.9401	0.8822	0.047*
C3	0.6676 (3)	0.8329 (2)	0.86608 (4)	0.0359 (3)
C4	0.4365 (3)	0.8886 (2)	0.87778 (4)	0.0395 (4)
H4	0.3302	0.8855	0.8598	0.047*
C5	0.3748 (4)	0.7633 (2)	0.90435 (4)	0.0469 (4)
H5	0.2192	0.7316	0.9032	0.056*
C6	0.5277 (4)	0.6267 (2)	0.89661 (5)	0.0576 (6)
H6B	0.5562	0.5628	0.9159	0.069*
H6A	0.4647	0.5581	0.8799	0.069*
C7	0.8226 (4)	1.2368 (2)	0.85457 (4)	0.0457 (4)
C8	0.6599 (5)	1.3136 (4)	0.83165 (6)	0.0666 (6)
H8C	0.6363	1.4231	0.8380	0.100*
H8B	0.5225	1.2564	0.8325	0.100*
H8A	0.7170	1.3102	0.8098	0.100*
C9	1.0429 (4)	1.3199 (3)	0.85511 (7)	0.0701 (6)
H9B	1.1420	1.2623	0.8691	0.105*
H9C	1.0248	1.4273	0.8631	0.105*
H9A	1.1025	1.3232	0.8334	0.105*
C10	0.8314 (3)	0.7426 (2)	0.81616 (4)	0.0361 (3)
C11	0.7740 (3)	0.6775 (2)	0.78333 (4)	0.0369 (3)
C12	0.9415 (4)	0.6641 (3)	0.76038 (4)	0.0491 (4)
H12	1.0828	0.7009	0.7652	0.059*
C13	0.8968 (4)	0.5954 (3)	0.73032 (5)	0.0582 (5)
H13	1.0080	0.5875	0.7148	0.070*
C14	0.6894 (5)	0.5390 (3)	0.72342 (5)	0.0623 (6)
H14	0.6609	0.4922	0.7033	0.075*
C15	0.5228 (4)	0.5511 (3)	0.74619 (6)	0.0621 (6)
H15	0.3831	0.5112	0.7415	0.075*
C16	0.5637 (3)	0.6229 (3)	0.77623 (5)	0.0479 (4)
H16	0.4507	0.6341	0.7914	0.057*
C17	0.2826 (3)	0.9126 (3)	0.95157 (4)	0.0477 (4)
C18	0.3653 (4)	0.9719 (2)	0.98356 (4)	0.0475 (4)
C19	0.5728 (5)	0.9336 (3)	0.99530 (5)	0.0605 (5)
H19	0.6685	0.8707	0.9830	0.073*
C20	0.6362 (6)	0.9909 (4)	1.02587 (6)	0.0791 (8)
H20	0.7746	0.9653	1.0342	0.095*
C21	0.4942 (7)	1.0852 (4)	1.04379 (6)	0.0831 (9)
H21	0.5379	1.1235	1.0641	0.100*
C22	0.2893 (6)	1.1233 (4)	1.03201 (6)	0.0788 (8)
H22	0.1942	1.1865	1.0443	0.095*
C23	0.2242 (5)	1.0674 (3)	1.00179 (5)	0.0606 (6)
H23	0.0856	1.0939	0.9936	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0844 (11)	0.0392 (6)	0.0433 (7)	−0.0017 (7)	0.0146 (7)	−0.0098 (5)
O2	0.0874 (11)	0.0392 (6)	0.0392 (6)	−0.0010 (7)	0.0204 (7)	−0.0044 (5)
O3	0.0562 (8)	0.0416 (6)	0.0396 (6)	0.0110 (6)	0.0062 (6)	0.0031 (5)
O4	0.0521 (7)	0.0434 (6)	0.0424 (6)	0.0123 (6)	0.0078 (6)	−0.0030 (5)
O5	0.0523 (7)	0.0552 (7)	0.0311 (5)	0.0076 (6)	0.0072 (5)	−0.0005 (5)
O6	0.0528 (8)	0.1047 (14)	0.0508 (8)	0.0200 (10)	−0.0035 (7)	−0.0178 (9)
O7	0.0390 (6)	0.0500 (6)	0.0298 (5)	0.0027 (5)	0.0007 (4)	−0.0102 (5)
O8	0.0401 (6)	0.0607 (8)	0.0424 (6)	0.0043 (6)	−0.0024 (5)	−0.0143 (6)
C1	0.0598 (10)	0.0410 (8)	0.0299 (7)	0.0052 (8)	0.0020 (8)	−0.0058 (7)
C2	0.0439 (8)	0.0417 (8)	0.0307 (7)	0.0037 (7)	0.0010 (7)	−0.0056 (6)
C3	0.0413 (8)	0.0388 (8)	0.0275 (7)	0.0060 (7)	−0.0009 (6)	−0.0032 (6)
C4	0.0408 (8)	0.0491 (9)	0.0286 (7)	0.0049 (8)	0.0027 (6)	−0.0056 (7)
C5	0.0541 (10)	0.0506 (9)	0.0360 (8)	−0.0012 (9)	0.0097 (7)	−0.0050 (7)
C6	0.0780 (15)	0.0425 (9)	0.0523 (10)	0.0011 (10)	0.0217 (11)	−0.0001 (8)
C7	0.0545 (10)	0.0393 (8)	0.0435 (9)	0.0008 (9)	0.0076 (8)	−0.0036 (7)
C8	0.0701 (15)	0.0739 (14)	0.0559 (12)	0.0172 (13)	−0.0006 (12)	−0.0003 (11)
C9	0.0634 (14)	0.0671 (14)	0.0800 (15)	−0.0100 (13)	0.0069 (12)	−0.0134 (13)
C10	0.0408 (8)	0.0361 (7)	0.0315 (7)	0.0021 (7)	0.0025 (7)	−0.0039 (6)
C11	0.0454 (9)	0.0364 (7)	0.0290 (6)	0.0051 (7)	0.0004 (6)	−0.0020 (6)
C12	0.0515 (10)	0.0567 (10)	0.0391 (8)	0.0000 (9)	0.0066 (8)	−0.0065 (8)
C13	0.0734 (14)	0.0667 (12)	0.0346 (8)	0.0088 (12)	0.0122 (9)	−0.0097 (9)
C14	0.0805 (15)	0.0693 (13)	0.0370 (8)	0.0155 (13)	−0.0122 (10)	−0.0208 (9)
C15	0.0572 (12)	0.0734 (14)	0.0558 (11)	0.0064 (12)	−0.0127 (10)	−0.0247 (11)
C16	0.0473 (10)	0.0549 (10)	0.0414 (8)	0.0027 (9)	−0.0010 (8)	−0.0117 (8)
C17	0.0512 (11)	0.0564 (10)	0.0355 (8)	0.0069 (9)	0.0068 (8)	0.0003 (8)
C18	0.0607 (11)	0.0502 (9)	0.0315 (7)	0.0008 (9)	0.0058 (8)	0.0047 (7)
C19	0.0694 (13)	0.0703 (13)	0.0420 (9)	0.0067 (13)	−0.0031 (10)	0.0033 (9)
C20	0.091 (2)	0.0973 (19)	0.0493 (11)	−0.0043 (17)	−0.0210 (13)	0.0079 (13)
C21	0.123 (3)	0.0871 (18)	0.0391 (10)	−0.017 (2)	−0.0067 (14)	−0.0085 (12)
C22	0.114 (2)	0.0735 (15)	0.0488 (11)	−0.0001 (17)	0.0131 (15)	−0.0166 (12)
C23	0.0725 (14)	0.0620 (12)	0.0473 (10)	0.0087 (12)	0.0082 (10)	−0.0061 (9)

Geometric parameters (Å, º) top

O1—C1	1.382 (2)	C8—H8A	0.9600
O1—C7	1.437 (2)	C9—H9B	0.9600
O2—C2	1.412 (2)	C9—H9C	0.9600
O2—C7	1.426 (2)	C9—H9A	0.9600
O3—C3	1.397 (2)	C10—C11	1.492 (2)
O3—C6	1.445 (3)	C11—C16	1.384 (3)
O4—C4	1.410 (2)	C11—C12	1.389 (3)
O4—C1	1.432 (3)	C12—C13	1.386 (3)
O5—C17	1.346 (2)	C12—H12	0.9300
O5—C5	1.439 (2)	C13—C14	1.371 (4)
O6—C17	1.197 (3)	C13—H13	0.9300
O7—C10	1.362 (2)	C14—C15	1.378 (4)
O7—C3	1.4328 (17)	C14—H14	0.9300
O8—C10	1.194 (2)	C15—C16	1.392 (3)
C1—C2	1.528 (2)	C15—H15	0.9300
C1—H1	0.9800	C16—H16	0.9300
C2—C3	1.523 (3)	C17—C18	1.489 (3)
C2—H2	0.9800	C18—C19	1.383 (3)
C3—C4	1.551 (2)	C18—C23	1.387 (3)
C4—C5	1.555 (3)	C19—C20	1.395 (3)
C4—H4	0.9800	C19—H19	0.9300
C5—C6	1.502 (3)	C20—C21	1.378 (5)
C5—H5	0.9800	C20—H20	0.9300
C6—H6B	0.9700	C21—C22	1.369 (5)
C6—H6A	0.9700	C21—H21	0.9300
C7—C9	1.503 (3)	C22—C23	1.381 (3)
C7—C8	1.505 (3)	C22—H22	0.9300
C8—H8C	0.9600	C23—H23	0.9300
C8—H8B	0.9600

C1—O1—C7	109.27 (13)	C7—C8—H8A	109.5
C2—O2—C7	109.65 (13)	H8C—C8—H8A	109.5
C3—O3—C6	107.35 (16)	H8B—C8—H8A	109.5
C4—O4—C1	110.09 (14)	C7—C9—H9B	109.5
C17—O5—C5	116.50 (16)	C7—C9—H9C	109.5
C10—O7—C3	118.02 (13)	H9B—C9—H9C	109.5
O1—C1—O4	110.15 (17)	C7—C9—H9A	109.5
O1—C1—C2	105.39 (15)	H9B—C9—H9A	109.5
O4—C1—C2	106.30 (14)	H9C—C9—H9A	109.5
O1—C1—H1	111.6	O8—C10—O7	124.12 (14)
O4—C1—H1	111.6	O8—C10—C11	125.24 (15)
C2—C1—H1	111.6	O7—C10—C11	110.64 (14)
O2—C2—C3	111.52 (14)	C16—C11—C12	120.26 (16)
O2—C2—C1	102.53 (14)	C16—C11—C10	121.59 (15)
C3—C2—C1	103.82 (16)	C12—C11—C10	118.05 (17)
O2—C2—H2	112.7	C13—C12—C11	119.6 (2)
C3—C2—H2	112.7	C13—C12—H12	120.2
C1—C2—H2	112.7	C11—C12—H12	120.2
O3—C3—O7	110.60 (13)	C14—C13—C12	120.3 (2)
O3—C3—C2	110.03 (14)	C14—C13—H13	119.9
O7—C3—C2	115.89 (13)	C12—C13—H13	119.9
O3—C3—C4	107.55 (14)	C13—C14—C15	120.39 (18)
O7—C3—C4	107.02 (13)	C13—C14—H14	119.8
C2—C3—C4	105.26 (13)	C15—C14—H14	119.8
O4—C4—C3	107.09 (15)	C14—C15—C16	120.0 (2)
O4—C4—C5	114.09 (13)	C14—C15—H15	120.0
C3—C4—C5	103.45 (14)	C16—C15—H15	120.0
O4—C4—H4	110.6	C11—C16—C15	119.44 (19)
C3—C4—H4	110.6	C11—C16—H16	120.3
C5—C4—H4	110.6	C15—C16—H16	120.3
O5—C5—C6	107.33 (18)	O6—C17—O5	123.76 (18)
O5—C5—C4	109.90 (15)	O6—C17—C18	124.54 (19)
C6—C5—C4	102.30 (15)	O5—C17—C18	111.69 (17)
O5—C5—H5	112.3	C19—C18—C23	120.3 (2)
C6—C5—H5	112.3	C19—C18—C17	122.40 (19)
C4—C5—H5	112.3	C23—C18—C17	117.3 (2)
O3—C6—C5	105.23 (16)	C18—C19—C20	118.9 (3)
O3—C6—H6B	110.7	C18—C19—H19	120.5
C5—C6—H6B	110.7	C20—C19—H19	120.5
O3—C6—H6A	110.7	C21—C20—C19	120.2 (3)
C5—C6—H6A	110.7	C21—C20—H20	119.9
H6B—C6—H6A	108.8	C19—C20—H20	119.9
O2—C7—O1	106.09 (14)	C22—C21—C20	120.7 (2)
O2—C7—C9	111.09 (19)	C22—C21—H21	119.7
O1—C7—C9	107.87 (18)	C20—C21—H21	119.7
O2—C7—C8	107.70 (18)	C21—C22—C23	119.8 (3)
O1—C7—C8	110.62 (18)	C21—C22—H22	120.1
C9—C7—C8	113.3 (2)	C23—C22—H22	120.1
C7—C8—H8C	109.5	C22—C23—C18	120.1 (3)
C7—C8—H8B	109.5	C22—C23—H23	120.0
H8C—C8—H8B	109.5	C18—C23—H23	120.0

C7—O1—C1—O4	−93.88 (18)	O5—C5—C6—O3	−81.08 (19)
C7—O1—C1—C2	20.4 (2)	C4—C5—C6—O3	34.6 (2)
C4—O4—C1—O1	141.46 (13)	C2—O2—C7—O1	−11.8 (2)
C4—O4—C1—C2	27.76 (18)	C2—O2—C7—C9	105.2 (2)
C7—O2—C2—C3	133.74 (17)	C2—O2—C7—C8	−130.29 (19)
C7—O2—C2—C1	23.2 (2)	C1—O1—C7—O2	−6.4 (2)
O1—C1—C2—O2	−26.6 (2)	C1—O1—C7—C9	−125.5 (2)
O4—C1—C2—O2	90.33 (18)	C1—O1—C7—C8	110.2 (2)
O1—C1—C2—C3	−142.79 (15)	C3—O7—C10—O8	−7.7 (3)
O4—C1—C2—C3	−25.87 (18)	C3—O7—C10—C11	171.87 (13)
C6—O3—C3—O7	−91.18 (17)	O8—C10—C11—C16	159.8 (2)
C6—O3—C3—C2	139.50 (15)	O7—C10—C11—C16	−19.8 (2)
C6—O3—C3—C4	25.35 (17)	O8—C10—C11—C12	−16.5 (3)
C10—O7—C3—O3	−66.81 (19)	O7—C10—C11—C12	163.94 (17)
C10—O7—C3—C2	59.3 (2)	C16—C11—C12—C13	−0.1 (3)
C10—O7—C3—C4	176.32 (14)	C10—C11—C12—C13	176.24 (18)
O2—C2—C3—O3	149.85 (14)	C11—C12—C13—C14	−0.9 (3)
C1—C2—C3—O3	−100.44 (16)	C12—C13—C14—C15	0.5 (4)
O2—C2—C3—O7	23.5 (2)	C13—C14—C15—C16	0.9 (4)
C1—C2—C3—O7	133.17 (15)	C12—C11—C16—C15	1.5 (3)
O2—C2—C3—C4	−94.54 (16)	C10—C11—C16—C15	−174.7 (2)
C1—C2—C3—C4	15.16 (17)	C14—C15—C16—C11	−1.9 (4)
C1—O4—C4—C3	−17.61 (17)	C5—O5—C17—O6	2.7 (3)
C1—O4—C4—C5	96.22 (18)	C5—O5—C17—C18	−178.13 (16)
O3—C3—C4—O4	117.80 (14)	O6—C17—C18—C19	177.9 (2)
O7—C3—C4—O4	−123.34 (14)	O5—C17—C18—C19	−1.3 (3)
C2—C3—C4—O4	0.50 (16)	O6—C17—C18—C23	−1.5 (3)
O3—C3—C4—C5	−3.04 (17)	O5—C17—C18—C23	179.36 (19)
O7—C3—C4—C5	115.82 (15)	C23—C18—C19—C20	0.8 (4)
C2—C3—C4—C5	−120.34 (15)	C17—C18—C19—C20	−178.5 (2)
C17—O5—C5—C6	−161.55 (18)	C18—C19—C20—C21	−0.6 (4)
C17—O5—C5—C4	87.9 (2)	C19—C20—C21—C22	0.4 (5)
O4—C4—C5—O5	−21.2 (2)	C20—C21—C22—C23	−0.4 (5)
C3—C4—C5—O5	94.79 (16)	C21—C22—C23—C18	0.6 (4)
O4—C4—C5—C6	−134.95 (18)	C19—C18—C23—C22	−0.8 (4)
C3—C4—C5—C6	−18.98 (19)	C17—C18—C23—C22	178.6 (2)
C3—O3—C6—C5	−38.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.98	2.55	3.2793 (17)	131
C4—H4···O8ⁱⁱ	0.98	2.59	3.4882 (16)	153

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂O₈
M_r	426.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	6.05837 (10), 8.33827 (14), 40.9992 (7)
V (Å³)	2071.13 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.780, 0.812
No. of measured, independent and observed [I > 2σ(I)] reflections	10556, 2421, 2335
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.094, 1.06
No. of reflections	2421
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXL97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009), OLEX2 (Dolomanov et al., 2009).