3,7-Dideacetyl­khivorin

Zhang, H.; VanDerveer, D.; Chen, F.; Wang, X.; Wargovich, M.J.

doi:10.1107/S1600536807046363

3,7-Dideacetylkhivorin

H. Zhang, D. VanDerveer, F. Chen, X. Wang and M. J. Wargovich

The title compound, a D-seco limonoid (systematic name: 1α-acetyloxy-14,15β:21,23-diepoxy-3α,7α-dihydroxy-4,4,8-trimethyl-D-homo-24-nor-17-oxochola-20,22-dien-16-one), C₂₈H₃₈O₈, was isolated from the stem bark of African mahogany Khaya senegalensis (Meliaceae). The six-membered rings show chair, boat and half-chair conformations, while the furan ring is planar. The crystal packing is stabilized by both intra- and intermolecular O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046363/fl2161sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046363/fl2161Isup2.hkl Contains datablock I

CCDC reference: 663837

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.041
wR factor = 0.108
Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O8     -   C23     ..      10.77 su
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H9     ..  H18C    ..       1.79 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.98 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.35 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31

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           25.10
           From the CIF: _reflns_number_total               2711
           Count of symmetry unique reflns         2718
           Completeness (_total/calc)             99.74%
           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_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
  12 ALERT level G = General alerts; check

  13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

African mahogany Khaya senegalensis is a large evergreen tree growing mainly in the sub-Saharan savannah forests from Senegal to Uganda (Adesida et al., 1971). The plant is one of the most popular medicinal meliaceous plants used in African traditional remedies. It is used as a bitter tonic, folk and popular medicine against malaria, fever, mucous diarrhea, and venereal diseases as well as an anthelmintic and a taeniacide remedy (Olayinka et al., 1992; Iwu, 1993). Our earlier study showed that its stem bark extract displayed anti-proliferative, anti-inflammatory and pro-apoptotic effects on HT-29, HCT-15, HCA-7 cells (Androulakis et al., 2006). In the course of our chemical investigation of the plant bark, the title compound, was isolated as a major product from the CHCl₃ extract. This D-seco limonoid was originally isolated from the seeds of Khaya nyasica in Tanzania (Adesida et al., 1971) and was also found to be present in the fresh seeds of Khaya senegalensis (Govindachari & Kumari, 1998) in India and in the stem bark of khaya ivorensis in the Democratic Republic of Congo (Abdelgaleil et al., 2005). It was reported that this tetranortriterpenoid displayed moderate antifungal and antibacterial activities (Abdelgaleil et al., 2005). Also, the title compound showed growth inhibitory activities against different cell lines in our preliminary anti-cancer bioassay (Zhang et al., 2007). Although its structure was tentatively identified, no spectral data were presented in previous publications. Considering its biological importanc, we have undertaken the X-ray crystal analysis of this limonoid in order to firmly establish its structure and relative stereochemistry.

The title compound (Fig.1) contains four six-membered rings A—D, one three-membered ring E (C14/C15/O5), and one furan ring F linked to atom C17 of ring D through a C—C bond in an equatorial position, known as a D-seco type limonoid. The ring junctions A/B, B/C and C/D are all trans, while D/E is cis. The six-membered rings A—D adopt chair, chair, twist boat and half-chair conformations, while rings E and F are fairly planar moieties. The bond lengths and angles are with normal ranges (Allen et al., 1987), fairly close to their expected values and the data are comparable with the corresponding values in those of two similar D-seco limonoids: gedunin (Toscano et al., 1996) and 7-oxogedunin (Waratchareeyakul et al., 2004). The strong classical intra-molecular hydrogen bond, O3—H3···O1 and inter-molecular hydrogen-bonding interactions O4—H4···O3 (Table 1) connect the molecules together to form a network.

Related literature top

Geometry: Allen et al. (1987); Background: Androulakis et al. (2006); Iwu (1993); Olayinka et al. (1992). Isolation, NMR and MS data, and biological activity of the title compound: Abdelgaleil et al. (2005); Adesida et al. (1971); Govindachari & Kumari (1998); Zhang et al. (2007). Similar D-seco limonoids (gedunin and 7-oxogedunin): Toscano et al. (1996); Waratchareeyakul et al. (2004).

Experimental top

The plant stem bark was collected from the martime plains near Conakry, Republic of Guinea (west Africa) in November 2005. Air-dried and powdered raw material (495 g) were extracted by 5L methanol using a Soxhlet extrator. The MeOH extract was dried under reduced pressure to yield a crude extract (51 g). The crude extract was suspended in 300 ml water and partitioned with 400 ml trichloromethane three times to yield CHCl₃ fraction (5 g). This part was separated by conventional chromatography on silica gel, eluting with mixtures of hexane and acetone (increasing polarity). The purified powder (32 mg) of the title compound was obtained from the hexane:acetone = 4:1 fractions. Transparent rod shaped crystals of the title compound were suitable for X-ray diffraction after recrystallization from a solution of 5% CHCl₃ in MeOH by slow evaporation at room temperature.

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: PLATON (Spek,2003).

Figures top

Fig. 1. view of the title compound, showing 50% probability displacement and the atom-numbering scheme

1α-acetyloxy-14,15β:21,23-diepoxy-3α,7α-dihydroxy-4,4,8-trimethyl-D-homo-24-nor-17-oxochola-20,22-dien-16-one top

Crystal data top

C₂₈H₃₈O₈	D_x = 1.239 Mg m⁻³
M_r = 502.58	Melting point: _audit_update_record _audit_creation_method 'SHELXL-97' _chemical_name_systematic K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
a = 10.907 (2) Å	Cell parameters from 12261 reflections
b = 14.200 (3) Å	θ = 1.9–25.7°
c = 17.391 (4) Å	µ = 0.09 mm⁻¹
V = 2693.5 (9) Å³	T = 298 K
Z = 4	Rod, colourless
F(000) = 1080	0.48 × 0.46 × 0.29 mm

Data collection top

Rigaku Mercury CCD (2x2 bin mode) diffractometer	2711 independent reflections
Radiation source: Sealed Tube	2485 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.030
Detector resolution: 14.6199 pixels mm^-1	θ_max = 25.1°, θ_min = 2.2°
ω scans	h = −12→13
Absorption correction: multi-scan (REQAB; Rigaku/MSC, 2006)	k = −16→16
T_min = 0.958, T_max = 0.974	l = −20→20
23488 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[s²(F_o²) + (0.063P)² + 0.4442P]
2711 reflections	(Δ/σ)_max < 0.001
333 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₃₈O₈	V = 2693.5 (9) Å³
M_r = 502.58	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.907 (2) Å	µ = 0.09 mm⁻¹
b = 14.200 (3) Å	T = 298 K
c = 17.391 (4) Å	0.48 × 0.46 × 0.29 mm

Data collection top

Rigaku Mercury CCD (2x2 bin mode) diffractometer	2711 independent reflections
Absorption correction: multi-scan (REQAB; Rigaku/MSC, 2006)	2485 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.974	R_int = 0.030
23488 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.07	Δρ_max = 0.15 e Å⁻³
2711 reflections	Δρ_min = −0.18 e Å⁻³
333 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	−0.24761 (17)	0.03344 (13)	0.00185 (10)	0.0417 (4)
O2	−0.4201 (3)	−0.0522 (2)	0.00453 (17)	0.0943 (10)
O3	−0.2722 (3)	0.22356 (16)	−0.04014 (13)	0.0752 (8)
H3	−0.2628	0.1805	−0.0084	0.090*
O4	0.1384 (2)	0.09520 (13)	0.03037 (11)	0.0482 (5)
H4	0.1596	0.1513	0.0307	0.058*
O5	0.27970 (17)	−0.15088 (15)	0.01582 (12)	0.0533 (5)
O6	0.25238 (19)	−0.16923 (15)	0.17687 (12)	0.0583 (5)
O7	0.3671 (2)	−0.0430 (2)	0.18949 (16)	0.0853 (8)
O8	−0.0200 (3)	−0.3910 (3)	0.2456 (2)	0.1073 (11)
C1	−0.2334 (2)	0.0143 (2)	−0.08101 (13)	0.0390 (6)
H1	−0.2682	−0.0462	−0.0926	0.047*
C2	−0.3041 (3)	0.0904 (2)	−0.12480 (17)	0.0533 (7)
H2A	−0.3063	0.0739	−0.1783	0.064*
H2B	−0.3871	0.0916	−0.1064	0.064*
C3	−0.2496 (3)	0.1879 (2)	−0.11678 (17)	0.0593 (8)
H3A	−0.2930	0.2281	−0.1518	0.071*
C4	−0.1123 (3)	0.1934 (2)	−0.13845 (16)	0.0535 (7)
C5	−0.0427 (3)	0.11459 (17)	−0.09381 (15)	0.0402 (6)
H5	−0.0529	0.1310	−0.0407	0.048*
C6	0.0963 (3)	0.11405 (18)	−0.10582 (16)	0.0441 (6)
H6A	0.1147	0.0883	−0.1555	0.053*
H6B	0.1266	0.1775	−0.1044	0.053*
C7	0.1605 (2)	0.05603 (18)	−0.04411 (15)	0.0409 (6)
H7	0.2471	0.0569	−0.0539	0.049*
C8	0.1167 (2)	−0.04691 (16)	−0.04239 (13)	0.0327 (5)
C9	−0.0258 (2)	−0.04659 (15)	−0.03695 (13)	0.0305 (5)
H9	−0.0433	−0.0148	0.0105	0.037*
C10	−0.0948 (2)	0.01254 (16)	−0.09987 (13)	0.0327 (5)
C11	−0.0774 (2)	−0.14678 (17)	−0.02572 (16)	0.0401 (6)
H11A	−0.1611	−0.1420	−0.0091	0.048*
H11B	−0.0772	−0.1785	−0.0745	0.048*
C12	−0.0064 (3)	−0.20695 (17)	0.03248 (16)	0.0446 (6)
H12A	−0.0642	−0.2399	0.0643	0.053*
H12B	0.0404	−0.2532	0.0050	0.053*
C13	0.0805 (2)	−0.15048 (17)	0.08430 (13)	0.0346 (5)
C14	0.1681 (2)	−0.09790 (16)	0.03037 (14)	0.0346 (5)
C15	0.2863 (3)	−0.0707 (2)	0.06512 (18)	0.0507 (7)
H15	0.3256	−0.0155	0.0449	0.061*
C16	0.3058 (3)	−0.0916 (3)	0.14789 (19)	0.0581 (8)
C17	0.1596 (2)	−0.21977 (19)	0.13252 (16)	0.0449 (6)
H17	0.2003	−0.2623	0.0980	0.054*
C18	0.0126 (3)	−0.0847 (2)	0.14002 (15)	0.0453 (6)
H18A	0.0710	−0.0529	0.1721	0.068*
H18B	−0.0421	−0.1210	0.1715	0.068*
H18C	−0.0336	−0.0392	0.1113	0.068*
C19	−0.0872 (3)	−0.03207 (19)	−0.18109 (14)	0.0437 (6)
H19A	−0.0809	−0.0993	−0.1765	0.066*
H19B	−0.0163	−0.0082	−0.2074	0.066*
H19C	−0.1596	−0.0164	−0.2097	0.066*
C20	0.0914 (3)	−0.2766 (2)	0.19140 (18)	0.0543 (7)
C21	0.0267 (4)	−0.3566 (3)	0.1786 (2)	0.0758 (10)
H21	0.0153	−0.3851	0.1290	0.091*
C22	0.0852 (4)	−0.2612 (3)	0.2719 (2)	0.0794 (11)
H22	0.1235	−0.2106	0.2996	0.095*
C23	0.0167 (5)	−0.3296 (3)	0.3024 (3)	0.0912 (14)
H23	−0.0040	−0.3351	0.3558	0.109*
C28	−0.1018 (4)	0.1874 (3)	−0.22687 (18)	0.0718 (10)
H28A	−0.1493	0.1350	−0.2452	0.108*
H28B	−0.0175	0.1788	−0.2410	0.108*
H28C	−0.1322	0.2445	−0.2494	0.108*
C29	−0.0636 (4)	0.2901 (2)	−0.1140 (3)	0.0825 (12)
H29A	−0.1159	0.3385	−0.1342	0.124*
H29B	0.0180	0.2984	−0.1336	0.124*
H29C	−0.0623	0.2940	−0.0589	0.124*
C30	0.1665 (3)	−0.0979 (2)	−0.11413 (16)	0.0493 (7)
H30A	0.1459	−0.0624	−0.1593	0.074*
H30B	0.1307	−0.1595	−0.1175	0.074*
H30C	0.2540	−0.1035	−0.1103	0.074*
C31	−0.3440 (3)	−0.0070 (2)	0.03741 (18)	0.0533 (7)
C32	−0.3406 (3)	0.0131 (3)	0.12206 (19)	0.0743 (11)
H32A	−0.4218	0.0076	0.1429	0.112*
H32B	−0.3104	0.0757	0.1304	0.112*
H32C	−0.2875	−0.0314	0.1470	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (9)	0.0501 (10)	0.0347 (8)	0.0061 (8)	0.0047 (8)	0.0034 (8)
O2	0.0707 (16)	0.131 (3)	0.0810 (18)	−0.0390 (18)	0.0204 (15)	−0.0125 (18)
O3	0.114 (2)	0.0517 (12)	0.0600 (13)	0.0383 (14)	0.0212 (14)	0.0016 (11)
O4	0.0665 (12)	0.0353 (9)	0.0427 (10)	−0.0147 (9)	−0.0038 (9)	−0.0048 (8)
O5	0.0383 (10)	0.0660 (13)	0.0555 (11)	0.0188 (9)	0.0077 (9)	0.0045 (10)
O6	0.0500 (11)	0.0700 (13)	0.0549 (11)	−0.0003 (10)	−0.0148 (10)	0.0165 (11)
O7	0.0725 (16)	0.108 (2)	0.0753 (16)	−0.0286 (16)	−0.0363 (14)	0.0087 (16)
O8	0.104 (2)	0.095 (2)	0.123 (3)	0.0002 (19)	0.026 (2)	0.061 (2)
C1	0.0392 (14)	0.0467 (14)	0.0312 (12)	0.0056 (11)	−0.0009 (10)	0.0004 (10)
C2	0.0527 (16)	0.0635 (18)	0.0438 (15)	0.0192 (15)	−0.0016 (13)	0.0097 (14)
C3	0.080 (2)	0.0537 (16)	0.0441 (15)	0.0302 (16)	0.0029 (15)	0.0086 (13)
C4	0.078 (2)	0.0381 (14)	0.0449 (15)	0.0115 (14)	0.0049 (15)	0.0105 (12)
C5	0.0540 (15)	0.0334 (12)	0.0330 (12)	0.0024 (11)	0.0043 (12)	0.0007 (10)
C6	0.0564 (16)	0.0353 (13)	0.0405 (14)	−0.0098 (12)	0.0065 (12)	0.0044 (11)
C7	0.0410 (13)	0.0412 (13)	0.0404 (13)	−0.0087 (11)	0.0057 (11)	0.0012 (11)
C8	0.0337 (11)	0.0320 (11)	0.0325 (11)	−0.0017 (10)	0.0035 (10)	−0.0029 (10)
C9	0.0353 (11)	0.0276 (11)	0.0286 (11)	−0.0011 (9)	−0.0006 (9)	−0.0025 (9)
C10	0.0373 (12)	0.0324 (12)	0.0285 (11)	0.0010 (10)	0.0009 (10)	0.0001 (9)
C11	0.0430 (13)	0.0310 (11)	0.0464 (14)	−0.0070 (10)	−0.0102 (11)	0.0009 (11)
C12	0.0486 (14)	0.0288 (12)	0.0563 (15)	−0.0069 (11)	−0.0076 (13)	0.0050 (11)
C13	0.0360 (12)	0.0314 (11)	0.0364 (12)	0.0026 (10)	0.0007 (10)	0.0019 (10)
C14	0.0307 (11)	0.0331 (11)	0.0400 (13)	0.0042 (10)	0.0025 (10)	−0.0043 (10)
C15	0.0364 (13)	0.0583 (17)	0.0575 (17)	−0.0052 (13)	−0.0058 (12)	0.0104 (15)
C16	0.0426 (15)	0.071 (2)	0.0601 (18)	−0.0019 (15)	−0.0149 (14)	0.0086 (16)
C17	0.0429 (13)	0.0433 (13)	0.0486 (15)	0.0090 (12)	−0.0014 (12)	0.0045 (12)
C18	0.0501 (15)	0.0463 (14)	0.0395 (13)	0.0143 (13)	0.0052 (12)	0.0036 (11)
C19	0.0525 (15)	0.0477 (14)	0.0310 (12)	0.0035 (12)	−0.0020 (12)	−0.0058 (11)
C20	0.0543 (16)	0.0491 (16)	0.0596 (18)	0.0119 (13)	0.0040 (14)	0.0208 (14)
C21	0.089 (3)	0.062 (2)	0.076 (2)	−0.0034 (19)	0.007 (2)	0.0257 (19)
C22	0.100 (3)	0.079 (2)	0.059 (2)	0.013 (2)	0.010 (2)	0.0194 (19)
C23	0.112 (3)	0.091 (3)	0.070 (2)	0.023 (3)	0.031 (3)	0.039 (2)
C28	0.098 (3)	0.068 (2)	0.0496 (17)	0.017 (2)	0.0084 (18)	0.0247 (16)
C29	0.115 (3)	0.0352 (15)	0.097 (3)	0.0076 (19)	0.006 (3)	0.0101 (17)
C30	0.0500 (16)	0.0561 (16)	0.0418 (14)	0.0093 (14)	0.0078 (12)	−0.0101 (13)
C31	0.0432 (15)	0.0650 (18)	0.0519 (16)	0.0034 (14)	0.0122 (14)	0.0070 (15)
C32	0.066 (2)	0.107 (3)	0.0494 (17)	0.013 (2)	0.0184 (16)	0.0155 (19)

Geometric parameters (Å, º) top

O1—C31	1.348 (3)	C11—C12	1.534 (4)
O1—C1	1.475 (3)	C11—H11A	0.9600
O2—C31	1.195 (4)	C11—H11B	0.9600
O3—C3	1.447 (4)	C12—C13	1.534 (4)
O3—H3	0.8299	C12—H12A	0.9600
O4—C7	1.430 (3)	C12—H12B	0.9600
O4—H4	0.8299	C13—C14	1.534 (3)
O5—C15	1.427 (4)	C13—C18	1.536 (3)
O5—C14	1.453 (3)	C13—C17	1.554 (3)
O6—C16	1.345 (4)	C14—C15	1.475 (4)
O6—C17	1.461 (3)	C15—C16	1.485 (4)
O7—C16	1.203 (4)	C15—H15	0.9600
O8—C21	1.363 (5)	C17—C20	1.501 (4)
O8—C23	1.376 (6)	C17—H17	0.9600
C1—C2	1.530 (4)	C18—H18A	0.9599
C1—C10	1.547 (3)	C18—H18B	0.9599
C1—H1	0.9600	C18—H18C	0.9599
C2—C3	1.513 (5)	C19—H19A	0.9599
C2—H2A	0.9600	C19—H19B	0.9599
C2—H2B	0.9600	C19—H19C	0.9599
C3—C4	1.546 (5)	C20—C21	1.356 (5)
C3—H3A	0.9600	C20—C22	1.419 (5)
C4—C29	1.533 (5)	C21—H21	0.9600
C4—C28	1.544 (4)	C22—C23	1.335 (6)
C4—C5	1.560 (4)	C22—H22	0.9600
C5—C6	1.530 (4)	C23—H23	0.9600
C5—C10	1.560 (3)	C28—H28A	0.9599
C5—H5	0.9600	C28—H28B	0.9599
C6—C7	1.523 (4)	C28—H28C	0.9599
C6—H6A	0.9600	C29—H29A	0.9599
C6—H6B	0.9600	C29—H29B	0.9599
C7—C8	1.538 (3)	C29—H29C	0.9599
C7—H7	0.9600	C30—H30A	0.9599
C8—C30	1.541 (3)	C30—H30B	0.9599
C8—C9	1.558 (3)	C30—H30C	0.9599
C8—C14	1.562 (3)	C31—C32	1.500 (5)
C9—C11	1.542 (3)	C32—H32A	0.9599
C9—C10	1.571 (3)	C32—H32B	0.9599
C9—H9	0.9600	C32—H32C	0.9599
C10—C19	1.550 (3)

C31—O1—C1	116.9 (2)	C14—C13—C12	106.3 (2)
C3—O3—H3	109.5	C14—C13—C18	113.0 (2)
C7—O4—H4	109.5	C12—C13—C18	113.0 (2)
C15—O5—C14	61.59 (16)	C14—C13—C17	107.0 (2)
C16—O6—C17	120.3 (2)	C12—C13—C17	109.2 (2)
C21—O8—C23	106.2 (3)	C18—C13—C17	108.2 (2)
O1—C1—C2	107.6 (2)	O5—C14—C15	58.35 (18)
O1—C1—C10	108.2 (2)	O5—C14—C13	112.13 (19)
C2—C1—C10	113.5 (2)	C15—C14—C13	114.9 (2)
O1—C1—H1	109.1	O5—C14—C8	113.55 (19)
C2—C1—H1	109.1	C15—C14—C8	121.6 (2)
C10—C1—H1	109.1	C13—C14—C8	119.83 (19)
C3—C2—C1	113.7 (2)	O5—C15—C14	60.06 (16)
C3—C2—H2A	108.8	O5—C15—C16	115.5 (3)
C1—C2—H2A	108.8	C14—C15—C16	118.0 (3)
C3—C2—H2B	108.8	O5—C15—H15	117.0
C1—C2—H2B	108.8	C14—C15—H15	117.0
H2A—C2—H2B	107.7	C16—C15—H15	117.0
O3—C3—C2	109.8 (3)	O7—C16—O6	119.0 (3)
O3—C3—C4	111.8 (3)	O7—C16—C15	123.2 (3)
C2—C3—C4	113.9 (2)	O6—C16—C15	117.7 (3)
O3—C3—H3A	107.0	O6—C17—C20	104.3 (2)
C2—C3—H3A	107.0	O6—C17—C13	111.0 (2)
C4—C3—H3A	107.0	C20—C17—C13	115.7 (2)
C29—C4—C28	107.5 (3)	O6—C17—H17	108.5
C29—C4—C3	108.3 (3)	C20—C17—H17	108.5
C28—C4—C3	108.2 (3)	C13—C17—H17	108.5
C29—C4—C5	109.6 (3)	C13—C18—H18A	109.5
C28—C4—C5	114.8 (3)	C13—C18—H18B	109.5
C3—C4—C5	108.3 (2)	H18A—C18—H18B	109.5
C6—C5—C4	114.7 (2)	C13—C18—H18C	109.5
C6—C5—C10	110.3 (2)	H18A—C18—H18C	109.5
C4—C5—C10	117.1 (2)	H18B—C18—H18C	109.5
C6—C5—H5	104.4	C10—C19—H19A	109.5
C4—C5—H5	104.4	C10—C19—H19B	109.5
C10—C5—H5	104.4	H19A—C19—H19B	109.5
C7—C6—C5	111.2 (2)	C10—C19—H19C	109.5
C7—C6—H6A	109.4	H19A—C19—H19C	109.5
C5—C6—H6A	109.4	H19B—C19—H19C	109.5
C7—C6—H6B	109.4	C21—C20—C22	105.5 (3)
C5—C6—H6B	109.4	C21—C20—C17	126.6 (3)
H6A—C6—H6B	108.0	C22—C20—C17	127.8 (3)
O4—C7—C6	110.5 (2)	C20—C21—O8	110.7 (4)
O4—C7—C8	107.44 (19)	C20—C21—H21	124.7
C6—C7—C8	112.6 (2)	O8—C21—H21	124.7
O4—C7—H7	108.7	C23—C22—C20	107.8 (4)
C6—C7—H7	108.7	C23—C22—H22	126.1
C8—C7—H7	108.7	C20—C22—H22	126.1
C7—C8—C30	108.7 (2)	C22—C23—O8	109.8 (4)
C7—C8—C9	108.0 (2)	C22—C23—H23	125.1
C30—C8—C9	113.7 (2)	O8—C23—H23	125.1
C7—C8—C14	110.2 (2)	C4—C28—H28A	109.5
C30—C8—C14	108.2 (2)	C4—C28—H28B	109.5
C9—C8—C14	108.09 (19)	H28A—C28—H28B	109.5
C11—C9—C8	111.68 (19)	C4—C28—H28C	109.5
C11—C9—C10	113.97 (19)	H28A—C28—H28C	109.5
C8—C9—C10	115.93 (19)	H28B—C28—H28C	109.5
C11—C9—H9	104.6	C4—C29—H29A	109.5
C8—C9—H9	104.6	C4—C29—H29B	109.5
C10—C9—H9	104.6	H29A—C29—H29B	109.5
C1—C10—C19	104.6 (2)	C4—C29—H29C	109.5
C1—C10—C5	109.1 (2)	H29A—C29—H29C	109.5
C19—C10—C5	114.9 (2)	H29B—C29—H29C	109.5
C1—C10—C9	109.20 (19)	C8—C30—H30A	109.5
C19—C10—C9	113.00 (19)	C8—C30—H30B	109.5
C5—C10—C9	105.96 (19)	H30A—C30—H30B	109.5
C12—C11—C9	114.4 (2)	C8—C30—H30C	109.5
C12—C11—H11A	108.7	H30A—C30—H30C	109.5
C9—C11—H11A	108.7	H30B—C30—H30C	109.5
C12—C11—H11B	108.7	O2—C31—O1	123.4 (3)
C9—C11—H11B	108.7	O2—C31—C32	126.1 (3)
H11A—C11—H11B	107.6	O1—C31—C32	110.5 (3)
C13—C12—C11	114.10 (19)	C31—C32—H32A	109.5
C13—C12—H12A	108.7	C31—C32—H32B	109.5
C11—C12—H12A	108.7	H32A—C32—H32B	109.5
C13—C12—H12B	108.7	C31—C32—H32C	109.5
C11—C12—H12B	108.7	H32A—C32—H32C	109.5
H12A—C12—H12B	107.6	H32B—C32—H32C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.83	2.10	2.810 (2)	143
O4—H4···O3ⁱ	0.83	1.93	2.758 (2)	171

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₈O₈
M_r	502.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	10.907 (2), 14.200 (3), 17.391 (4)
V (Å³)	2693.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.46 × 0.29

Data collection
Diffractometer	Rigaku Mercury CCD (2x2 bin mode)
Absorption correction	Multi-scan (REQAB; Rigaku/MSC, 2006)
T_min, T_max	0.958, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	23488, 2711, 2485
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.07
No. of reflections	2711
No. of parameters	333
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: CrystalClear (Rigaku/MSC, 2006), SHELXTL (Bruker, 2000), PLATON (Spek,2003).