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Acta Cryst. (2007). E63, o4162    [ doi:10.1107/S1600536807046363 ]

3,7-Dideacetylkhivorin

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

Abstract top

The title compound, a D-seco limonoid (systematic name: 1[alpha]-acetyloxy-14,15[beta]:21,23-diepoxy-3[alpha],7[alpha]-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.

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.

Refinement top

Since the most electron-rich atom is oxygen it was not possible to determine the absolute configuration. Therefore, Friedel reflections were merged before final refinement because of the absence of significant anomalous scattering effects. All H atoms were geometrically fixed and allowed to ride on the corresponding non-H atom with C—H = 0.96 Å, O—H = 0.83 Å, and Uiso(H) = 1.5Ueq(C) of the attached C atom for methyl H atoms and 1.2Ueq(C) for other H atoms.

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
[Figure 1] 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
C28H38O8Dx = 1.239 Mg m−3
Mr = 502.58Melting point: _audit_update_record _audit_creation_method 'SHELXL-97' _chemical_name_systematic K
Orthorhombic, P212121Mo Kα radiation
λ = 0.7107 Å
a = 10.907 (2) ÅCell parameters from 12261 reflections
b = 14.200 (3) Åθ = 1.9–25.7º
c = 17.391 (4) ŵ = 0.09 mm−1
V = 2693.5 (9) Å3T = 298 (2) K
Z = 4Rod, colourless
F000 = 10800.48 × 0.46 × 0.29 mm
Data collection top
Rigaku Mercury CCD (2x2 bin mode) diffractometer2711 independent reflections
Radiation source: Sealed Tube2485 reflections with I > 2σ(I)
Monochromator: Graphite MonochromatorRint = 0.030
Detector resolution: 14.6199 pixels mm-1θmax = 25.1º
T = 298(2) Kθmin = 2.2º
ω scansh = −12→13
Absorption correction: multi-scan
(REQAB; Rigaku/MSC, 2006)		k = −16→16
Tmin = 0.958, Tmax = 0.974l = −20→20
23488 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[s2(Fo2) + (0.063P)2 + 0.4442P]
R[F2 > 2σ(F2)] = 0.041(Δ/σ)max < 0.001
wR(F2) = 0.109Δρmax = 0.15 e Å−3
S = 1.07Δρmin = −0.18 e Å−3
2711 reflectionsExtinction correction: none
333 parameters
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
Crystal data top
C28H38O8V = 2693.5 (9) Å3
Mr = 502.58Z = 4
Orthorhombic, P212121Mo Kα
a = 10.907 (2) ŵ = 0.09 mm−1
b = 14.200 (3) ÅT = 298 (2) K
c = 17.391 (4) Å0.48 × 0.46 × 0.29 mm
Data collection top
Rigaku Mercury CCD (2x2 bin mode) diffractometer2711 independent reflections
Absorption correction: multi-scan
(REQAB; Rigaku/MSC, 2006)		2485 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.974Rint = 0.030
23488 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041Δρmax = 0.15 e Å−3
wR(F2) = 0.109Δρmin = −0.18 e Å−3
S = 1.07Absolute structure: ?
2711 reflectionsFlack parameter: ?
333 parametersRogers parameter: ?
H-atom parameters constrained
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^ > 2sigma(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
xyzUiso*/Ueq
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)
H3−0.26280.1805−0.00840.090*
O40.1384 (2)0.09520 (13)0.03037 (11)0.0482 (5)
H40.15960.15130.03070.058*
O50.27970 (17)−0.15088 (15)0.01582 (12)0.0533 (5)
O60.25238 (19)−0.16923 (15)0.17687 (12)0.0583 (5)
O70.3671 (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)
H1−0.2682−0.0462−0.09260.047*
C2−0.3041 (3)0.0904 (2)−0.12480 (17)0.0533 (7)
H2A−0.30630.0739−0.17830.064*
H2B−0.38710.0916−0.10640.064*
C3−0.2496 (3)0.1879 (2)−0.11678 (17)0.0593 (8)
H3A−0.29300.2281−0.15180.071*
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)
H5−0.05290.1310−0.04070.048*
C60.0963 (3)0.11405 (18)−0.10582 (16)0.0441 (6)
H6A0.11470.0883−0.15550.053*
H6B0.12660.1775−0.10440.053*
C70.1605 (2)0.05603 (18)−0.04411 (15)0.0409 (6)
H70.24710.0569−0.05390.049*
C80.1167 (2)−0.04691 (16)−0.04239 (13)0.0327 (5)
C9−0.0258 (2)−0.04659 (15)−0.03695 (13)0.0305 (5)
H9−0.0433−0.01480.01050.037*
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−0.1611−0.1420−0.00910.048*
H11B−0.0772−0.1785−0.07450.048*
C12−0.0064 (3)−0.20695 (17)0.03248 (16)0.0446 (6)
H12A−0.0642−0.23990.06430.053*
H12B0.0404−0.25320.00500.053*
C130.0805 (2)−0.15048 (17)0.08430 (13)0.0346 (5)
C140.1681 (2)−0.09790 (16)0.03037 (14)0.0346 (5)
C150.2863 (3)−0.0707 (2)0.06512 (18)0.0507 (7)
H150.3256−0.01550.04490.061*
C160.3058 (3)−0.0916 (3)0.14789 (19)0.0581 (8)
C170.1596 (2)−0.21977 (19)0.13252 (16)0.0449 (6)
H170.2003−0.26230.09800.054*
C180.0126 (3)−0.0847 (2)0.14002 (15)0.0453 (6)
H18A0.0710−0.05290.17210.068*
H18B−0.0421−0.12100.17150.068*
H18C−0.0336−0.03920.11130.068*
C19−0.0872 (3)−0.03207 (19)−0.18109 (14)0.0437 (6)
H19A−0.0809−0.0993−0.17650.066*
H19B−0.0163−0.0082−0.20740.066*
H19C−0.1596−0.0164−0.20970.066*
C200.0914 (3)−0.2766 (2)0.19140 (18)0.0543 (7)
C210.0267 (4)−0.3566 (3)0.1786 (2)0.0758 (10)
H210.0153−0.38510.12900.091*
C220.0852 (4)−0.2612 (3)0.2719 (2)0.0794 (11)
H220.1235−0.21060.29960.095*
C230.0167 (5)−0.3296 (3)0.3024 (3)0.0912 (14)
H23−0.0040−0.33510.35580.109*
C28−0.1018 (4)0.1874 (3)−0.22687 (18)0.0718 (10)
H28A−0.14930.1350−0.24520.108*
H28B−0.01750.1788−0.24100.108*
H28C−0.13220.2445−0.24940.108*
C29−0.0636 (4)0.2901 (2)−0.1140 (3)0.0825 (12)
H29A−0.11590.3385−0.13420.124*
H29B0.01800.2984−0.13360.124*
H29C−0.06230.2940−0.05890.124*
C300.1665 (3)−0.0979 (2)−0.11413 (16)0.0493 (7)
H30A0.1459−0.0624−0.15930.074*
H30B0.1307−0.1595−0.11750.074*
H30C0.2540−0.1035−0.11030.074*
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−0.42180.00760.14290.112*
H32B−0.31040.07570.13040.112*
H32C−0.2875−0.03140.14700.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0403 (9)0.0501 (10)0.0347 (8)0.0061 (8)0.0047 (8)0.0034 (8)
O20.0707 (16)0.131 (3)0.0810 (18)−0.0390 (18)0.0204 (15)−0.0125 (18)
O30.114 (2)0.0517 (12)0.0600 (13)0.0383 (14)0.0212 (14)0.0016 (11)
O40.0665 (12)0.0353 (9)0.0427 (10)−0.0147 (9)−0.0038 (9)−0.0048 (8)
O50.0383 (10)0.0660 (13)0.0555 (11)0.0188 (9)0.0077 (9)0.0045 (10)
O60.0500 (11)0.0700 (13)0.0549 (11)−0.0003 (10)−0.0148 (10)0.0165 (11)
O70.0725 (16)0.108 (2)0.0753 (16)−0.0286 (16)−0.0363 (14)0.0087 (16)
O80.104 (2)0.095 (2)0.123 (3)0.0002 (19)0.026 (2)0.061 (2)
C10.0392 (14)0.0467 (14)0.0312 (12)0.0056 (11)−0.0009 (10)0.0004 (10)
C20.0527 (16)0.0635 (18)0.0438 (15)0.0192 (15)−0.0016 (13)0.0097 (14)
C30.080 (2)0.0537 (16)0.0441 (15)0.0302 (16)0.0029 (15)0.0086 (13)
C40.078 (2)0.0381 (14)0.0449 (15)0.0115 (14)0.0049 (15)0.0105 (12)
C50.0540 (15)0.0334 (12)0.0330 (12)0.0024 (11)0.0043 (12)0.0007 (10)
C60.0564 (16)0.0353 (13)0.0405 (14)−0.0098 (12)0.0065 (12)0.0044 (11)
C70.0410 (13)0.0412 (13)0.0404 (13)−0.0087 (11)0.0057 (11)0.0012 (11)
C80.0337 (11)0.0320 (11)0.0325 (11)−0.0017 (10)0.0035 (10)−0.0029 (10)
C90.0353 (11)0.0276 (11)0.0286 (11)−0.0011 (9)−0.0006 (9)−0.0025 (9)
C100.0373 (12)0.0324 (12)0.0285 (11)0.0010 (10)0.0009 (10)0.0001 (9)
C110.0430 (13)0.0310 (11)0.0464 (14)−0.0070 (10)−0.0102 (11)0.0009 (11)
C120.0486 (14)0.0288 (12)0.0563 (15)−0.0069 (11)−0.0076 (13)0.0050 (11)
C130.0360 (12)0.0314 (11)0.0364 (12)0.0026 (10)0.0007 (10)0.0019 (10)
C140.0307 (11)0.0331 (11)0.0400 (13)0.0042 (10)0.0025 (10)−0.0043 (10)
C150.0364 (13)0.0583 (17)0.0575 (17)−0.0052 (13)−0.0058 (12)0.0104 (15)
C160.0426 (15)0.071 (2)0.0601 (18)−0.0019 (15)−0.0149 (14)0.0086 (16)
C170.0429 (13)0.0433 (13)0.0486 (15)0.0090 (12)−0.0014 (12)0.0045 (12)
C180.0501 (15)0.0463 (14)0.0395 (13)0.0143 (13)0.0052 (12)0.0036 (11)
C190.0525 (15)0.0477 (14)0.0310 (12)0.0035 (12)−0.0020 (12)−0.0058 (11)
C200.0543 (16)0.0491 (16)0.0596 (18)0.0119 (13)0.0040 (14)0.0208 (14)
C210.089 (3)0.062 (2)0.076 (2)−0.0034 (19)0.007 (2)0.0257 (19)
C220.100 (3)0.079 (2)0.059 (2)0.013 (2)0.010 (2)0.0194 (19)
C230.112 (3)0.091 (3)0.070 (2)0.023 (3)0.031 (3)0.039 (2)
C280.098 (3)0.068 (2)0.0496 (17)0.017 (2)0.0084 (18)0.0247 (16)
C290.115 (3)0.0352 (15)0.097 (3)0.0076 (19)0.006 (3)0.0101 (17)
C300.0500 (16)0.0561 (16)0.0418 (14)0.0093 (14)0.0078 (12)−0.0101 (13)
C310.0432 (15)0.0650 (18)0.0519 (16)0.0034 (14)0.0122 (14)0.0070 (15)
C320.066 (2)0.107 (3)0.0494 (17)0.013 (2)0.0184 (16)0.0155 (19)
Geometric parameters (Å, °) top
O1—C311.348 (3)C11—C121.534 (4)
O1—C11.475 (3)C11—H11A0.9600
O2—C311.195 (4)C11—H11B0.9600
O3—C31.447 (4)C12—C131.534 (4)
O3—H30.8299C12—H12A0.9600
O4—C71.430 (3)C12—H12B0.9600
O4—H40.8299C13—C141.534 (3)
O5—C151.427 (4)C13—C181.536 (3)
O5—C141.453 (3)C13—C171.554 (3)
O6—C161.345 (4)C14—C151.475 (4)
O6—C171.461 (3)C15—C161.485 (4)
O7—C161.203 (4)C15—H150.9600
O8—C211.363 (5)C17—C201.501 (4)
O8—C231.376 (6)C17—H170.9600
C1—C21.530 (4)C18—H18A0.9599
C1—C101.547 (3)C18—H18B0.9599
C1—H10.9600C18—H18C0.9599
C2—C31.513 (5)C19—H19A0.9599
C2—H2A0.9600C19—H19B0.9599
C2—H2B0.9600C19—H19C0.9599
C3—C41.546 (5)C20—C211.356 (5)
C3—H3A0.9600C20—C221.419 (5)
C4—C291.533 (5)C21—H210.9600
C4—C281.544 (4)C22—C231.335 (6)
C4—C51.560 (4)C22—H220.9600
C5—C61.530 (4)C23—H230.9600
C5—C101.560 (3)C28—H28A0.9599
C5—H50.9600C28—H28B0.9599
C6—C71.523 (4)C28—H28C0.9599
C6—H6A0.9600C29—H29A0.9599
C6—H6B0.9600C29—H29B0.9599
C7—C81.538 (3)C29—H29C0.9599
C7—H70.9600C30—H30A0.9599
C8—C301.541 (3)C30—H30B0.9599
C8—C91.558 (3)C30—H30C0.9599
C8—C141.562 (3)C31—C321.500 (5)
C9—C111.542 (3)C32—H32A0.9599
C9—C101.571 (3)C32—H32B0.9599
C9—H90.9600C32—H32C0.9599
C10—C191.550 (3)
C31—O1—C1116.9 (2)C14—C13—C12106.3 (2)
C3—O3—H3109.5C14—C13—C18113.0 (2)
C7—O4—H4109.5C12—C13—C18113.0 (2)
C15—O5—C1461.59 (16)C14—C13—C17107.0 (2)
C16—O6—C17120.3 (2)C12—C13—C17109.2 (2)
C21—O8—C23106.2 (3)C18—C13—C17108.2 (2)
O1—C1—C2107.6 (2)O5—C14—C1558.35 (18)
O1—C1—C10108.2 (2)O5—C14—C13112.13 (19)
C2—C1—C10113.5 (2)C15—C14—C13114.9 (2)
O1—C1—H1109.1O5—C14—C8113.55 (19)
C2—C1—H1109.1C15—C14—C8121.6 (2)
C10—C1—H1109.1C13—C14—C8119.83 (19)
C3—C2—C1113.7 (2)O5—C15—C1460.06 (16)
C3—C2—H2A108.8O5—C15—C16115.5 (3)
C1—C2—H2A108.8C14—C15—C16118.0 (3)
C3—C2—H2B108.8O5—C15—H15117.0
C1—C2—H2B108.8C14—C15—H15117.0
H2A—C2—H2B107.7C16—C15—H15117.0
O3—C3—C2109.8 (3)O7—C16—O6119.0 (3)
O3—C3—C4111.8 (3)O7—C16—C15123.2 (3)
C2—C3—C4113.9 (2)O6—C16—C15117.7 (3)
O3—C3—H3A107.0O6—C17—C20104.3 (2)
C2—C3—H3A107.0O6—C17—C13111.0 (2)
C4—C3—H3A107.0C20—C17—C13115.7 (2)
C29—C4—C28107.5 (3)O6—C17—H17108.5
C29—C4—C3108.3 (3)C20—C17—H17108.5
C28—C4—C3108.2 (3)C13—C17—H17108.5
C29—C4—C5109.6 (3)C13—C18—H18A109.5
C28—C4—C5114.8 (3)C13—C18—H18B109.5
C3—C4—C5108.3 (2)H18A—C18—H18B109.5
C6—C5—C4114.7 (2)C13—C18—H18C109.5
C6—C5—C10110.3 (2)H18A—C18—H18C109.5
C4—C5—C10117.1 (2)H18B—C18—H18C109.5
C6—C5—H5104.4C10—C19—H19A109.5
C4—C5—H5104.4C10—C19—H19B109.5
C10—C5—H5104.4H19A—C19—H19B109.5
C7—C6—C5111.2 (2)C10—C19—H19C109.5
C7—C6—H6A109.4H19A—C19—H19C109.5
C5—C6—H6A109.4H19B—C19—H19C109.5
C7—C6—H6B109.4C21—C20—C22105.5 (3)
C5—C6—H6B109.4C21—C20—C17126.6 (3)
H6A—C6—H6B108.0C22—C20—C17127.8 (3)
O4—C7—C6110.5 (2)C20—C21—O8110.7 (4)
O4—C7—C8107.44 (19)C20—C21—H21124.7
C6—C7—C8112.6 (2)O8—C21—H21124.7
O4—C7—H7108.7C23—C22—C20107.8 (4)
C6—C7—H7108.7C23—C22—H22126.1
C8—C7—H7108.7C20—C22—H22126.1
C7—C8—C30108.7 (2)C22—C23—O8109.8 (4)
C7—C8—C9108.0 (2)C22—C23—H23125.1
C30—C8—C9113.7 (2)O8—C23—H23125.1
C7—C8—C14110.2 (2)C4—C28—H28A109.5
C30—C8—C14108.2 (2)C4—C28—H28B109.5
C9—C8—C14108.09 (19)H28A—C28—H28B109.5
C11—C9—C8111.68 (19)C4—C28—H28C109.5
C11—C9—C10113.97 (19)H28A—C28—H28C109.5
C8—C9—C10115.93 (19)H28B—C28—H28C109.5
C11—C9—H9104.6C4—C29—H29A109.5
C8—C9—H9104.6C4—C29—H29B109.5
C10—C9—H9104.6H29A—C29—H29B109.5
C1—C10—C19104.6 (2)C4—C29—H29C109.5
C1—C10—C5109.1 (2)H29A—C29—H29C109.5
C19—C10—C5114.9 (2)H29B—C29—H29C109.5
C1—C10—C9109.20 (19)C8—C30—H30A109.5
C19—C10—C9113.00 (19)C8—C30—H30B109.5
C5—C10—C9105.96 (19)H30A—C30—H30B109.5
C12—C11—C9114.4 (2)C8—C30—H30C109.5
C12—C11—H11A108.7H30A—C30—H30C109.5
C9—C11—H11A108.7H30B—C30—H30C109.5
C12—C11—H11B108.7O2—C31—O1123.4 (3)
C9—C11—H11B108.7O2—C31—C32126.1 (3)
H11A—C11—H11B107.6O1—C31—C32110.5 (3)
C13—C12—C11114.10 (19)C31—C32—H32A109.5
C13—C12—H12A108.7C31—C32—H32B109.5
C11—C12—H12A108.7H32A—C32—H32B109.5
C13—C12—H12B108.7C31—C32—H32C109.5
C11—C12—H12B108.7H32A—C32—H32C109.5
H12A—C12—H12B107.6H32B—C32—H32C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.832.102.810 (2)143
O4—H4···O3i0.831.932.758 (2)171
Symmetry codes: (i) x+1/2, −y+1/2, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O10.832.102.810 (2)143
O4—H4···O3i0.831.932.758 (2)171
Symmetry codes: (i) x+1/2, −y+1/2, −z.
Acknowledgements top

The authors thank the National Institutes of Health (Bethedsa, MD, USA) and South Carolina Nutrition Research Consortium (Columbia, SC, USA) for financial research support (grant No. NIH R21CA107138).

references
References top

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