(5aR,8aR,9R)-9-(3,4,5-Tri­methoxy­phenyl)-5a,6,8a,9-tetra­hydro­furo­[3′,4′:6,7]­naphtho­[2,3-d][1,3]­dioxole-5,8-dione

Shi, J.-F.; Wang, Y.-G.

doi:10.1107/S1600536803008948

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(5aR,8aR,9R)-9-(3,4,5-Trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

J.-F. Shi and Y.-G. Wang

The title compound, C₂₂H₂₀O₈, a product of oxidation of podophyllotoxin, a lignan of the phenyltetralin type, represents a synthon for potential antitumour agents. It has the same configuration of three chiral centres as the starting material, podophyllotoxin, and, as well as the latter, contains a γ-lactone ring trans-fused to the tricylic system. Non-classical C—H

O hydrogen bonds link the molecules in the crystal structure into infinite chains along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008948/ya6159sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008948/ya6159Isup2.hkl Contains datablock I

CCDC reference: 214809

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.033
wR factor = 0.112
Data-to-parameter ratio = 9.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.106
          Value of mu given      =     0.110

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               2610
         Count of symmetry unique reflns         2621
         Completeness (_total/calc)             99.58%
         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
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Podophyllotoxin is a lignan of phenyltetralin type, which is widespread in higher plants. The discovery of the antitumour activity of etoposide (VP-16) and teniposide (VM-26), semisynthetic analogues of the naturally occurring podophyllotoxin, has stirred up the renewed interest in this field in the recent years (Damayanthi & Lown, 1998; Silverberg et al., 2000; Van Vliet et al., 2001). In a continuation of our previous work (Xu et al., 2002; Ma et al., 2000; Cao et al., 1999), we have synthesized potential antitumour agents with the structure of 4-heterocyclespiropodophyllotoxins using the title compound, podophyllotoxone, (I), as a starting material. Herein we report the crystal structure of (I).

The molecular structure of (I) is shown in Fig. 1. Selected molecular parameters and hydrogen-bond geometric characteristics are listed in Tables 1 and 2, respectively. The relative configuration of the chiral centres at atoms C5a, C8a and C9 is the same as in the starting compound, podophyllotoxin, which was not unexpected, as the chiral centres were not affected by the reaction. The absolute configuration was chosen in accordance with the known configuration of podophyllotoxin (Gordaliza et al., 2001). Atom H8a in (I) is cis relative to H9 and trans relative to H5a. The observed trans-fusion of the γ-lactone was proved essential to the bioactivity of podophyllotoxin derivatives (Brewer et al., 1979). The loss of activity of picropodophyllotoxin, which contains a cis-fused γ-lactone, has been attributed to differences in the conformation (Gensler et al., 1977).

In the crystal structure, non-classical C—H···O hydrogen bonds play an important role, resulting in the formation of polymeric chains of the molecules of the title compounds running along the crystallographic a axis.

Experimental top

Pyridinium dichromate (PDC; 0.89 g, 2.40 mmol) was added to a solution of podophyllotoxin (0.69 g, 1.65 mmol) in dry dichloromethane (20 ml) and stirred at room temperature for 4 h. The excess of PDC was removed by filtration followed by column chromatography of the residue on silica gel to give 520 mg (78%) of podophyllotoxone (Gordaliza et al., 2001). Colorless crystals were obtained from an ethyl acetate solution after it was left to stand for 4 d. C and H were analysed using a Carlo-Erba 1160 instrument. Analysis calculated for C₂₂H₂₀O₈: C 64.07, H 4.89%; found: C 63.83, H 4.92%. ¹H NMR (CDCl₃, 500 MHz): δ 7.55 (s, 1H), 6.71 (s, 1H), 6.39 (s, 2H), 6.10 (ss, 2H), 4.85 (d, 1H), 4.55 and 4.36 (dd, 2H), 3.82 (s, 3H), 3.75 (s, 6H), 3.51 (m, 1H), 3.27 (dd, 1H).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1993); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of podophyllotoxone, (I). Displacement ellipsoids are drawn at the 30% probablility level.
	Fig. 2. Polymeric chains formed due to the C—H···O hydrogen bonds in the crystal packing of the title compound (see Table 2 for symmetry codes).

(I) top

Crystal data top

C₂₂H₂₀O₈	F(000) = 864
M_r = 412.38	D_x = 1.386 Mg m⁻³ D_m = 1.379 Mg m⁻³ D_m measured by flotation in a mixture of hexane and carbontetrachloride
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.4927 (9) Å	θ = 3.0–26.5°
b = 12.1940 (11) Å	µ = 0.11 mm⁻¹
c = 24.9681 (18) Å	T = 293 K
V = 1976.8 (4) Å³	Prism, colorless
Z = 4	0.45 × 0.3 × 0.25 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1817 reflections with I > 2σ(I)
ω/2θ scans	R_int = 0.015
Absorption correction: ψ scan (North et al., 1968)	θ_max = 27.5°, θ_min = 1.6°
T_min = 0.963, T_max = 0.974	h = −8→8
4509 measured reflections	k = −15→15
2610 independent reflections	l = −32→32

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0667P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.033	(Δ/σ)_max < 0.001
wR(F²) = 0.112	Δρ_max = 0.23 e Å⁻³
S = 0.98	Δρ_min = −0.25 e Å⁻³
2610 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
272 parameters	Extinction coefficient: 0.0133 (17)
0 restraints

Crystal data top

C₂₂H₂₀O₈	V = 1976.8 (4) Å³
M_r = 412.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.4927 (9) Å	µ = 0.11 mm⁻¹
b = 12.1940 (11) Å	T = 293 K
c = 24.9681 (18) Å	0.45 × 0.3 × 0.25 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2610 independent reflections
Absorption correction: ψ scan (North et al., 1968)	1817 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.974	R_int = 0.015
4509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.98	Δρ_max = 0.23 e Å⁻³
2610 reflections	Δρ_min = −0.25 e Å⁻³
272 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.

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

	x	y	z	U_iso*/U_eq
C2	0.3339 (7)	−0.2267 (3)	0.06118 (18)	0.0853 (12)
H2A	0.2786	−0.276	0.0343	0.102*
H2B	0.3792	−0.2699	0.0916	0.102*
C3A	0.4716 (6)	−0.0592 (2)	0.05652 (11)	0.0527 (8)
C4	0.5954 (5)	0.0284 (2)	0.05157 (11)	0.0506 (7)
H4	0.7248	0.0222	0.0359	0.061*
C4A	0.5225 (5)	0.1307 (2)	0.07098 (10)	0.0426 (6)
C5	0.6568 (5)	0.2269 (2)	0.06469 (10)	0.0451 (6)
C5A	0.5788 (4)	0.3315 (2)	0.08826 (11)	0.0458 (7)
H5A	0.6144	0.3326	0.1264	0.055*
C6	0.6426 (6)	0.4404 (3)	0.06363 (14)	0.0668 (9)
H6A	0.7728	0.4653	0.0783	0.08*
H6B	0.6551	0.4344	0.025	0.08*
C8	0.3044 (6)	0.4577 (3)	0.09154 (12)	0.0552 (8)
C8A	0.3467 (5)	0.3369 (2)	0.08316 (10)	0.0447 (7)
H8A	0.3161	0.3221	0.0454	0.054*
C9	0.2392 (4)	0.2475 (2)	0.11477 (10)	0.0419 (6)
H9	0.0927	0.25	0.1054	0.05*
C9A	0.3252 (5)	0.1386 (2)	0.09408 (10)	0.0422 (6)
C10	0.2017 (5)	0.0453 (3)	0.09833 (11)	0.0518 (7)
H10	0.0713	0.0489	0.1136	0.062*
C10A	0.2784 (5)	−0.0513 (3)	0.07935 (12)	0.0548 (8)
C11	0.2552 (4)	0.2596 (2)	0.17518 (10)	0.0398 (6)
C12	0.1103 (4)	0.3232 (2)	0.20177 (10)	0.0435 (6)
H12	0.0054	0.3569	0.1825	0.052*
C13	0.1204 (5)	0.3368 (2)	0.25649 (11)	0.0470 (7)
C13A	−0.1912 (6)	0.4404 (3)	0.25986 (15)	0.0718 (10)
H13A	−0.2721	0.4813	0.2851	0.108*
H13B	−0.2719	0.381	0.2458	0.108*
H13C	−0.1493	0.4876	0.2311	0.108*
C14	0.2758 (4)	0.2861 (2)	0.28575 (10)	0.0463 (7)
C14A	0.1794 (6)	0.2143 (3)	0.36825 (13)	0.0753 (10)
H14A	0.1906	0.2261	0.4062	0.113*
H14B	0.2388	0.1447	0.3592	0.113*
H14C	0.0368	0.215	0.358	0.113*
C15	0.4209 (4)	0.2224 (2)	0.25943 (10)	0.0453 (7)
C15A	0.7144 (6)	0.1063 (3)	0.26739 (14)	0.0691 (10)
H15A	0.8075	0.0798	0.2943	0.104*
H15B	0.7899	0.147	0.241	0.104*
H15C	0.6466	0.0454	0.2506	0.104*
C16	0.4108 (4)	0.2090 (2)	0.20434 (10)	0.0427 (6)
H16	0.5084	0.1661	0.1869	0.051*
O1	0.1811 (5)	−0.15024 (19)	0.07740 (11)	0.0808 (8)
O3	0.5046 (5)	−0.16511 (18)	0.03935 (9)	0.0726 (7)
O5	0.8250 (3)	0.22234 (18)	0.04240 (8)	0.0567 (5)
O7	0.4771 (5)	0.51390 (17)	0.07818 (10)	0.0722 (7)
O8	0.1495 (4)	0.50262 (19)	0.10486 (9)	0.0713 (7)
O13	−0.0150 (4)	0.39790 (19)	0.28581 (8)	0.0664 (6)
O14	0.2866 (4)	0.29970 (18)	0.34039 (7)	0.0615 (6)
O15	0.5659 (4)	0.1752 (2)	0.29143 (8)	0.0647 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.105 (3)	0.0383 (18)	0.113 (3)	−0.008 (2)	−0.010 (3)	−0.015 (2)
C3A	0.076 (2)	0.0333 (15)	0.0491 (15)	0.0050 (17)	−0.0024 (15)	−0.0062 (12)
C4	0.0602 (19)	0.0469 (17)	0.0446 (14)	0.0085 (16)	0.0030 (14)	−0.0045 (13)
C4A	0.0513 (16)	0.0384 (15)	0.0380 (12)	0.0023 (13)	−0.0010 (12)	−0.0027 (11)
C5	0.0517 (16)	0.0466 (16)	0.0371 (13)	−0.0010 (15)	−0.0023 (12)	−0.0027 (12)
C5A	0.0575 (17)	0.0391 (15)	0.0408 (13)	−0.0051 (14)	0.0006 (12)	−0.0034 (12)
C6	0.082 (2)	0.0472 (19)	0.071 (2)	−0.0079 (19)	0.012 (2)	0.0003 (16)
C8	0.079 (2)	0.0388 (17)	0.0477 (16)	0.0044 (19)	−0.0054 (16)	−0.0037 (13)
C8A	0.0617 (18)	0.0375 (15)	0.0349 (12)	0.0029 (14)	−0.0054 (12)	−0.0031 (11)
C9	0.0434 (14)	0.0375 (15)	0.0449 (13)	0.0012 (13)	−0.0032 (11)	−0.0045 (11)
C9A	0.0495 (16)	0.0370 (15)	0.0400 (13)	0.0015 (14)	−0.0056 (12)	−0.0023 (11)
C10	0.0555 (17)	0.0432 (17)	0.0568 (16)	−0.0026 (15)	0.0023 (14)	−0.0047 (13)
C10A	0.070 (2)	0.0367 (16)	0.0575 (17)	−0.0091 (16)	−0.0045 (16)	−0.0023 (13)
C11	0.0431 (13)	0.0322 (14)	0.0441 (13)	−0.0034 (12)	0.0022 (11)	−0.0010 (11)
C12	0.0450 (14)	0.0373 (15)	0.0481 (14)	0.0017 (13)	−0.0007 (12)	−0.0005 (12)
C13	0.0521 (16)	0.0363 (16)	0.0526 (15)	−0.0006 (14)	0.0082 (13)	−0.0076 (12)
C13A	0.060 (2)	0.071 (2)	0.083 (2)	0.018 (2)	0.0100 (19)	−0.0140 (19)
C14	0.0565 (17)	0.0400 (15)	0.0423 (13)	−0.0055 (14)	0.0022 (12)	−0.0032 (12)
C14A	0.092 (2)	0.081 (3)	0.0531 (17)	0.009 (3)	0.0121 (19)	0.0118 (18)
C15	0.0498 (16)	0.0404 (16)	0.0458 (14)	0.0011 (14)	−0.0017 (12)	0.0046 (12)
C15A	0.065 (2)	0.072 (2)	0.069 (2)	0.023 (2)	−0.0089 (18)	0.0082 (18)
C16	0.0449 (14)	0.0386 (15)	0.0447 (13)	0.0065 (13)	0.0039 (11)	0.0000 (12)
O1	0.0935 (18)	0.0400 (13)	0.1090 (19)	−0.0135 (14)	0.0064 (16)	−0.0126 (13)
O3	0.1007 (19)	0.0381 (12)	0.0792 (15)	0.0078 (14)	0.0064 (15)	−0.0140 (11)
O5	0.0533 (11)	0.0637 (14)	0.0532 (10)	−0.0043 (12)	0.0059 (10)	−0.0082 (10)
O7	0.0936 (18)	0.0359 (12)	0.0870 (16)	−0.0020 (13)	0.0085 (16)	−0.0005 (11)
O8	0.0914 (18)	0.0474 (14)	0.0753 (15)	0.0230 (15)	−0.0043 (14)	−0.0062 (11)
O13	0.0717 (15)	0.0680 (15)	0.0596 (12)	0.0249 (14)	0.0089 (12)	−0.0127 (11)
O14	0.0795 (15)	0.0624 (14)	0.0427 (10)	−0.0008 (13)	−0.0014 (10)	−0.0089 (10)
O15	0.0703 (14)	0.0737 (16)	0.0501 (11)	0.0218 (13)	−0.0076 (10)	0.0026 (11)

Geometric parameters (Å, º) top

C2—O1	1.420 (5)	C9A—C10	1.396 (4)
C2—O3	1.445 (5)	C10—C10A	1.364 (4)
C2—H2A	0.97	C10—H10	0.93
C2—H2B	0.97	C10A—O1	1.363 (4)
C3A—C4	1.343 (4)	C11—C12	1.388 (4)
C3A—O3	1.377 (4)	C11—C16	1.390 (4)
C3A—C10A	1.381 (5)	C12—C13	1.378 (4)
C4—C4A	1.420 (4)	C12—H12	0.93
C4—H4	0.93	C13—O13	1.365 (3)
C4A—C9A	1.408 (4)	C13—C14	1.391 (4)
C4A—C5	1.471 (4)	C13A—O13	1.413 (4)
C5—O5	1.227 (4)	C13A—H13A	0.96
C5—C5A	1.492 (4)	C13A—H13B	0.96
C5A—C8A	1.514 (4)	C13A—H13C	0.96
C5A—C6	1.521 (4)	C14—O14	1.376 (3)
C5A—H5A	0.98	C14—C15	1.386 (4)
C6—O7	1.446 (4)	C14A—O14	1.433 (4)
C6—H6A	0.97	C14A—H14A	0.96
C6—H6B	0.97	C14A—H14B	0.96
C8—O8	1.193 (4)	C14A—H14C	0.96
C8—O7	1.356 (4)	C15—O15	1.362 (3)
C8—C8A	1.513 (4)	C15—C16	1.387 (4)
C8A—C9	1.516 (4)	C15A—O15	1.413 (4)
C8A—H8A	0.98	C15A—H15A	0.96
C9—C11	1.519 (3)	C15A—H15B	0.96
C9—C9A	1.530 (4)	C15A—H15C	0.96
C9—H9	0.98	C16—H16	0.93

O1—C2—O3	107.6 (3)	C10A—C10—C9A	117.9 (3)
O1—C2—H2A	110.2	C10A—C10—H10	121
O3—C2—H2A	110.2	C9A—C10—H10	121
O1—C2—H2B	110.2	O1—C10A—C10	127.5 (3)
O3—C2—H2B	110.2	O1—C10A—C3A	110.1 (3)
H2A—C2—H2B	108.5	C10—C10A—C3A	122.4 (3)
C4—C3A—O3	128.6 (3)	C12—C11—C16	119.4 (2)
C4—C3A—C10A	121.7 (3)	C12—C11—C9	118.9 (2)
O3—C3A—C10A	109.6 (3)	C16—C11—C9	121.8 (2)
C3A—C4—C4A	117.9 (3)	C13—C12—C11	120.6 (3)
C3A—C4—H4	121	C13—C12—H12	119.7
C4A—C4—H4	121	C11—C12—H12	119.7
C9A—C4A—C4	120.2 (3)	O13—C13—C12	124.5 (3)
C9A—C4A—C5	121.9 (2)	O13—C13—C14	115.4 (2)
C4—C4A—C5	117.8 (3)	C12—C13—C14	120.1 (3)
O5—C5—C4A	122.7 (3)	O13—C13A—H13A	109.5
O5—C5—C5A	121.3 (3)	O13—C13A—H13B	109.5
C4A—C5—C5A	116.0 (2)	H13A—C13A—H13B	109.5
C5—C5A—C8A	110.0 (2)	O13—C13A—H13C	109.5
C5—C5A—C6	119.6 (2)	H13A—C13A—H13C	109.5
C8A—C5A—C6	101.5 (3)	H13B—C13A—H13C	109.5
C5—C5A—H5A	108.4	O14—C14—C15	120.2 (2)
C8A—C5A—H5A	108.4	O14—C14—C13	120.3 (3)
C6—C5A—H5A	108.4	C15—C14—C13	119.6 (2)
O7—C6—C5A	103.7 (3)	O14—C14A—H14A	109.5
O7—C6—H6A	111	O14—C14A—H14B	109.5
C5A—C6—H6A	111	H14A—C14A—H14B	109.5
O7—C6—H6B	111	O14—C14A—H14C	109.5
C5A—C6—H6B	111	H14A—C14A—H14C	109.5
H6A—C6—H6B	109	H14B—C14A—H14C	109.5
O8—C8—O7	122.3 (3)	O15—C15—C14	115.4 (2)
O8—C8—C8A	129.7 (3)	O15—C15—C16	124.4 (3)
O7—C8—C8A	107.9 (3)	C14—C15—C16	120.3 (3)
C8—C8A—C5A	102.3 (3)	O15—C15A—H15A	109.5
C8—C8A—C9	123.0 (3)	O15—C15A—H15B	109.5
C5A—C8A—C9	112.5 (2)	H15A—C15A—H15B	109.5
C8—C8A—H8A	106	O15—C15A—H15C	109.5
C5A—C8A—H8A	106	H15A—C15A—H15C	109.5
C9—C8A—H8A	106	H15B—C15A—H15C	109.5
C8A—C9—C11	114.6 (2)	C15—C16—C11	120.1 (3)
C8A—C9—C9A	106.3 (2)	C15—C16—H16	119.9
C11—C9—C9A	113.2 (2)	C11—C16—H16	119.9
C8A—C9—H9	107.5	C10A—O1—C2	105.5 (3)
C11—C9—H9	107.5	C3A—O3—C2	104.5 (3)
C9A—C9—H9	107.5	C8—O7—C6	111.3 (2)
C10—C9A—C4A	119.8 (3)	C13—O13—C13A	118.4 (2)
C10—C9A—C9	118.2 (2)	C14—O14—C14A	111.6 (2)
C4A—C9A—C9	122.0 (2)	C15—O15—C15A	118.3 (2)

O3—C3A—C4—C4A	177.6 (3)	O3—C3A—C10A—O1	−0.4 (4)
C10A—C3A—C4—C4A	0.4 (4)	C4—C3A—C10A—C10	−0.2 (5)
C3A—C4—C4A—C9A	−0.6 (4)	O3—C3A—C10A—C10	−177.8 (3)
C3A—C4—C4A—C5	−179.0 (3)	C8A—C9—C11—C12	87.0 (3)
C9A—C4A—C5—O5	−176.5 (2)	C9A—C9—C11—C12	−150.9 (2)
C4—C4A—C5—O5	1.8 (4)	C8A—C9—C11—C16	−92.8 (3)
C9A—C4A—C5—C5A	4.9 (4)	C9A—C9—C11—C16	29.3 (3)
C4—C4A—C5—C5A	−176.8 (2)	C16—C11—C12—C13	0.3 (4)
O5—C5—C5A—C8A	146.8 (3)	C9—C11—C12—C13	−179.5 (2)
C4A—C5—C5A—C8A	−34.5 (3)	C11—C12—C13—O13	179.9 (3)
O5—C5—C5A—C6	30.1 (4)	C11—C12—C13—C14	−0.5 (4)
C4A—C5—C5A—C6	−151.2 (3)	O13—C13—C14—O14	−0.5 (4)
C5—C5A—C6—O7	154.7 (3)	C12—C13—C14—O14	179.8 (3)
C8A—C5A—C6—O7	33.6 (3)	O13—C13—C14—C15	−179.9 (3)
O8—C8—C8A—C5A	−158.8 (3)	C12—C13—C14—C15	0.4 (4)
O7—C8—C8A—C5A	24.6 (3)	O14—C14—C15—O15	1.1 (4)
O8—C8—C8A—C9	−31.3 (5)	C13—C14—C15—O15	−179.5 (3)
O7—C8—C8A—C9	152.0 (3)	O14—C14—C15—C16	−179.7 (3)
C5—C5A—C8A—C8	−162.4 (2)	C13—C14—C15—C16	−0.2 (4)
C6—C5A—C8A—C8	−34.8 (3)	O15—C15—C16—C11	179.2 (2)
C5—C5A—C8A—C9	63.8 (3)	C14—C15—C16—C11	0.1 (4)
C6—C5A—C8A—C9	−168.6 (2)	C12—C11—C16—C15	−0.1 (4)
C8—C8A—C9—C11	−54.3 (4)	C9—C11—C16—C15	179.7 (3)
C5A—C8A—C9—C11	68.6 (3)	C10—C10A—O1—C2	−172.4 (3)
C8—C8A—C9—C9A	179.9 (3)	C3A—C10A—O1—C2	10.3 (4)
C5A—C8A—C9—C9A	−57.2 (3)	O3—C2—O1—C10A	−16.1 (4)
C4—C4A—C9A—C10	0.6 (4)	C4—C3A—O3—C2	173.0 (3)
C5—C4A—C9A—C10	178.8 (2)	C10A—C3A—O3—C2	−9.5 (4)
C4—C4A—C9A—C9	−179.1 (2)	O1—C2—O3—C3A	15.7 (4)
C5—C4A—C9A—C9	−0.8 (4)	O8—C8—O7—C6	180.0 (3)
C8A—C9—C9A—C10	−153.6 (3)	C8A—C8—O7—C6	−3.1 (3)
C11—C9—C9A—C10	79.8 (3)	C5A—C6—O7—C8	−19.7 (3)
C8A—C9—C9A—C4A	26.1 (3)	C12—C13—O13—C13A	7.5 (5)
C11—C9—C9A—C4A	−100.5 (3)	C14—C13—O13—C13A	−172.1 (3)
C4A—C9A—C10—C10A	−0.3 (4)	C15—C14—O14—C14A	−87.7 (3)
C9—C9A—C10—C10A	179.4 (2)	C13—C14—O14—C14A	92.9 (3)
C9A—C10—C10A—O1	−176.9 (3)	C14—C15—O15—C15A	178.0 (3)
C9A—C10—C10A—C3A	0.1 (4)	C16—C15—O15—C15A	−1.2 (4)
C4—C3A—C10A—O1	177.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O8ⁱ	0.97	2.57	3.531 (5)	169
C9—H9···O5ⁱⁱ	0.98	2.37	3.254 (3)	150
C8A—H8A···O5ⁱⁱⁱ	0.98	2.26	3.220 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀O₈
M_r	412.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.4927 (9), 12.1940 (11), 24.9681 (18)
V (Å³)	1976.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.3 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.963, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4509, 2610, 1817
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.112, 0.98
No. of reflections	2610
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure corporation, 1992), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1993), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993), WinGX (Farrugia, 1999).

Selected torsion angles (º) top

C6—C5A—C8A—C8

−34.8 (3)

C5—C5A—C8A—C9

63.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O8ⁱ	0.97	2.57	3.531 (5)	169
C9—H9···O5ⁱⁱ	0.98	2.37	3.254 (3)	150
C8A—H8A···O5ⁱⁱⁱ	0.98	2.26	3.220 (3)	167

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

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