Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C40H48O8, is a derivative of gambogic acid, which is an effective telomerase inhibitor and displays potent anti­cancer activity both in vitro and in vivo. The three fused rings, A, B and C. are almost coplanar, with a mean deviation of 0.0670 (3) Å from their least-squares plane. The bridged structural unit including rings D, E and G forms a conformation like that of triethyl­enediamine. The structure is assembled via C—H...O hydrogen bonds. One methyl group is disordered over two positions; the site occupancy factors are ca 0.7 and 0.3.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049537/bq2036sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049537/bq2036Isup2.hkl
Contains datablock I

CCDC reference: 667358

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.153
  • Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.49 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34 PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C25 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H31A .. H26F .. 2.12 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.60 Deg. C26 -C24 -C26' 1.555 1.555 1.555
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 25.01 From the CIF: _reflns_number_total 3235 Count of symmetry unique reflns 3246 Completeness (_total/calc) 99.66% 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 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 125
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 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

Garcinia L. Planch (e.g. Garcinia hanburyi Hook. and Garcinia morella Gesv.), is used in traditional Chinese medicine for detoxification, maintaining hemostasis, and as an anthelmintic. Gambogic acid (GBA), the primary component of Gamboge, is a prenylated xanthonoid that has the bridged structural moiety of tricyclo-4-oxa[4.3.1.0]decan-2-one. GBA is an effective telomerase inhibitor and displays potent anticancer activity both in vitro and in vivo. Moreover, GBA has been shown to induce apoptosis in a cell cycle independent manner. In order to study the structure–activity relationship of GBA, several derivates were synthesized and showed potential antitumor activity. The title compound, 6-methoxy-methyl-gambogate, is a derivative of them (Liu et al., 2004). We report here the crystal structure of (I).

The crystal structure of the title compound is shown in Fig. 1. The three fused rings A(O1/C1–C4/C9), B(C4–C9) and C(O2/C6/C7/C10–C12) is almost coplanar with mean deviation being 0.0670 (3) Å from their least square plane. Rings D(C10/C11/C13–C16), E(C13–C15/C17–C19) and G(C10/C13–C15/C18/C19) formed a conformation like triethylenediamine. Three chains including H(C34–C39/O7/O8), I(C27–C31) and J(C21–C26) exists in the compound. Chain H is almost planar indicated by the mean deviations being 0.0436 (2) Å from their least square plane, and it have a dihedral angle of 12.1 (6)° with the plane of the fused rings A, B and C. The double bond C35C36 has a syn conformation with torision angle C38—C35—C36—C37 being -177.1 (5)°.

The title compound is assembled via hydrogen bonds C2—H2···O8i and C31—H31C···O6ii [Symmetry code: (i) 1 - x, 0.5 + y, 1 - z; (ii) 1 - x, 0.5 + y, -z] as shown in Fig. 2. Details of the hydrogen bonds geometry is shown in Table 1.

Related literature top

For related literature, see Liu et al. (2004).

Experimental top

Gambogic acid (100 mg) dissolved in acetone (10 ml), anhydride K2CO3 (300 mg) and iodomethane (1 ml) was added and stirred at room temperature for a week. Inpoured the reagent into water (10 ml), and extracted with ether (60 ml) for 3 times. The ether layer was evaporated afrer being washed by water and dryed with anhydride Na2SO4. The residue was separated by silica chromatography, 6-methoxyl-methyl-gambogate (30 mg) was isolated as yellow needles. The title compound was dissolved in ethanol to get saturated solution, the cube crystals were obtained after a week's standing.

Refinement top

The positions of the H atoms of the hydroxyl groups were located initially in a difference Fourier map and then constrained to ride on the parent O atom with O—H = 0.82–0.85, Uiso(H) = 1.5Ueq(O). The methyl H atoms were constrained to an ideal geometry with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.93–0.97 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). Friedel pairs were averaged before the final refinement as the absolute could not be determined unambiguously.

Structure description top

Garcinia L. Planch (e.g. Garcinia hanburyi Hook. and Garcinia morella Gesv.), is used in traditional Chinese medicine for detoxification, maintaining hemostasis, and as an anthelmintic. Gambogic acid (GBA), the primary component of Gamboge, is a prenylated xanthonoid that has the bridged structural moiety of tricyclo-4-oxa[4.3.1.0]decan-2-one. GBA is an effective telomerase inhibitor and displays potent anticancer activity both in vitro and in vivo. Moreover, GBA has been shown to induce apoptosis in a cell cycle independent manner. In order to study the structure–activity relationship of GBA, several derivates were synthesized and showed potential antitumor activity. The title compound, 6-methoxy-methyl-gambogate, is a derivative of them (Liu et al., 2004). We report here the crystal structure of (I).

The crystal structure of the title compound is shown in Fig. 1. The three fused rings A(O1/C1–C4/C9), B(C4–C9) and C(O2/C6/C7/C10–C12) is almost coplanar with mean deviation being 0.0670 (3) Å from their least square plane. Rings D(C10/C11/C13–C16), E(C13–C15/C17–C19) and G(C10/C13–C15/C18/C19) formed a conformation like triethylenediamine. Three chains including H(C34–C39/O7/O8), I(C27–C31) and J(C21–C26) exists in the compound. Chain H is almost planar indicated by the mean deviations being 0.0436 (2) Å from their least square plane, and it have a dihedral angle of 12.1 (6)° with the plane of the fused rings A, B and C. The double bond C35C36 has a syn conformation with torision angle C38—C35—C36—C37 being -177.1 (5)°.

The title compound is assembled via hydrogen bonds C2—H2···O8i and C31—H31C···O6ii [Symmetry code: (i) 1 - x, 0.5 + y, 1 - z; (ii) 1 - x, 0.5 + y, -z] as shown in Fig. 2. Details of the hydrogen bonds geometry is shown in Table 1.

For related literature, see Liu et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the packing diagram of the title compound shown the C—H···O hydrogen bonds. Atoms marked with (i) and (ii) are at the symmetric position of (1 - x, 0.5 + y, 1 - z) and (1 - x, 0.5 + y, -z), respectively. Some H atoms are omitted for the sake of clarity.
Methyl 6-methoxygambogate top
Crystal data top
C40H48O8F(000) = 704
Mr = 656.78Dx = 1.232 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2245 reflections
a = 7.865 (3) Åθ = 2.4–21.5°
b = 17.017 (7) ŵ = 0.09 mm1
c = 13.711 (6) ÅT = 298 K
β = 105.322 (6)°Prism, colourless
V = 1769.8 (13) Å30.54 × 0.40 × 0.27 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3235 independent reflections
Radiation source: fine-focus sealed tube2055 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 98
Tmin = 0.955, Tmax = 0.977k = 2017
8951 measured reflectionsl = 1416
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0745P)2 + 0.3642P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3235 reflectionsΔρmax = 0.32 e Å3
432 parametersΔρmin = 0.48 e Å3
125 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods
Crystal data top
C40H48O8V = 1769.8 (13) Å3
Mr = 656.78Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.865 (3) ŵ = 0.09 mm1
b = 17.017 (7) ÅT = 298 K
c = 13.711 (6) Å0.54 × 0.40 × 0.27 mm
β = 105.322 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3235 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2055 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.977Rint = 0.045
8951 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049125 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å3
3235 reflectionsΔρmin = 0.48 e Å3
432 parametersAbsolute structure: Flack (1983), with how many Friedel pairs?
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
xyzUiso*/UeqOcc. (<1)
O10.5187 (6)0.4902 (2)0.2713 (3)0.0607 (11)
O20.7046 (4)0.23511 (19)0.2426 (2)0.0438 (8)
O30.9237 (7)0.2103 (3)0.5463 (3)0.1002 (18)
O40.8083 (6)0.3577 (2)0.5729 (3)0.0662 (12)
O50.5472 (4)0.0946 (2)0.1436 (2)0.0484 (9)
O60.5658 (6)0.0343 (2)0.2965 (3)0.0706 (12)
O70.1983 (6)0.3344 (3)0.3839 (3)0.0737 (12)
O80.3480 (8)0.2268 (3)0.4380 (4)0.1069 (19)
C10.4618 (9)0.5561 (3)0.3239 (4)0.0602 (15)
C20.5470 (10)0.5550 (4)0.4337 (4)0.0739 (19)
H20.54040.59990.47120.089*
C30.6330 (9)0.4927 (4)0.4817 (4)0.0626 (17)
H30.67770.49390.55170.075*
C40.6574 (8)0.4233 (3)0.4258 (4)0.0478 (13)
C50.7372 (7)0.3556 (3)0.4701 (4)0.0462 (13)
C60.7569 (7)0.2895 (3)0.4128 (4)0.0433 (12)
C70.6901 (6)0.2951 (3)0.3070 (3)0.0383 (12)
C80.6127 (6)0.3626 (3)0.2596 (4)0.0389 (11)
C90.5938 (7)0.4244 (3)0.3201 (4)0.0433 (12)
C100.7517 (6)0.1570 (3)0.2772 (4)0.0413 (12)
C110.8407 (7)0.1514 (3)0.3876 (4)0.0504 (14)
C120.8475 (7)0.2180 (4)0.4566 (4)0.0592 (16)
C130.5929 (6)0.1014 (3)0.2509 (4)0.0422 (12)
C140.6617 (8)0.0210 (3)0.2962 (4)0.0512 (14)
C150.8607 (8)0.0173 (3)0.3400 (5)0.0608 (15)
H150.90210.03480.36640.073*
C160.8921 (8)0.0789 (3)0.4205 (5)0.0618 (16)
H160.94340.06770.48830.074*
C170.7047 (7)0.1018 (3)0.1087 (4)0.0498 (13)
C180.8537 (7)0.1191 (3)0.2049 (4)0.0496 (13)
H180.93770.15670.19000.060*
C190.9515 (7)0.0471 (4)0.2605 (5)0.0621 (16)
H19A1.07260.06120.29340.074*
H19B0.95290.00570.21220.074*
C200.2619 (10)0.5505 (5)0.3030 (6)0.095 (2)
H20A0.20940.55300.23140.143*
H20B0.21940.59330.33560.143*
H20C0.23120.50160.32880.143*
C210.5154 (9)0.6285 (4)0.2739 (5)0.0726 (16)
H21A0.47260.67490.30110.087*
H21B0.45800.62660.20200.087*
C220.7133 (10)0.6369 (4)0.2884 (6)0.090 (2)
H22A0.77160.63620.36020.109*
H22B0.75540.59200.25790.109*
C230.7639 (11)0.7107 (5)0.2432 (6)0.101 (2)
H230.74580.75700.27520.121*
C240.8284 (12)0.7198 (6)0.1670 (7)0.1156 (18)
C250.8507 (13)0.6514 (6)0.1007 (7)0.1156 (18)
H25A0.90120.66980.04840.173*
H25B0.73780.62810.07060.173*
H25C0.92720.61280.14100.173*
C260.888 (2)0.7909 (10)0.1209 (14)0.111 (3)0.66 (2)
H26A0.80230.80370.05880.166*0.66 (2)
H26B0.99930.78030.10720.166*0.66 (2)
H26C0.90030.83430.16690.166*0.66 (2)
C26'0.858 (5)0.8123 (12)0.167 (3)0.111 (3)0.34 (2)
H26D0.90770.82630.11270.166*0.34 (2)
H26E0.93770.82780.23040.166*0.34 (2)
H26F0.74750.83870.15900.166*0.34 (2)
C270.5530 (7)0.3704 (3)0.1460 (3)0.0426 (12)
H27A0.44520.40100.12750.051*
H27B0.52730.31860.11620.051*
C280.6908 (7)0.4095 (3)0.1038 (4)0.0527 (14)
H280.77240.44060.14890.063*
C290.7106 (8)0.4053 (4)0.0109 (5)0.0641 (17)
C300.8509 (11)0.4509 (5)0.0172 (6)0.101 (3)
H30A0.92610.47460.04230.151*
H30B0.79840.49130.06460.151*
H30C0.91920.41650.04750.151*
C310.5965 (11)0.3570 (4)0.0713 (5)0.085 (2)
H31A0.49920.33650.04920.128*
H31B0.66400.31430.08750.128*
H31C0.55270.38910.13020.128*
C320.7212 (10)0.0255 (4)0.0523 (5)0.0759 (19)
H32A0.73030.01830.09750.114*
H32B0.82470.02790.02780.114*
H32C0.61900.01920.00370.114*
C330.6785 (9)0.1691 (4)0.0333 (4)0.0640 (16)
H33A0.56620.16360.01530.096*
H33B0.77050.16810.00080.096*
H33C0.68220.21820.06840.096*
C340.2699 (8)0.2663 (4)0.3681 (5)0.0580 (15)
C350.2475 (6)0.2510 (3)0.2599 (4)0.0500 (13)
C360.3255 (6)0.1904 (3)0.2271 (4)0.0493 (13)
H360.31110.18860.15760.059*
C370.4320 (7)0.1257 (3)0.2856 (4)0.0508 (13)
H37A0.35650.08010.28210.061*
H37B0.47100.14150.35600.061*
C380.1371 (8)0.3088 (4)0.1866 (4)0.0674 (17)
H38A0.12860.29210.11860.101*
H38B0.19120.35980.19740.101*
H38C0.02130.31150.19700.101*
C390.2139 (10)0.3574 (5)0.4855 (5)0.088 (2)
H39A0.18790.31330.52290.131*
H39B0.13250.39920.48650.131*
H39C0.33200.37510.51570.131*
C400.7167 (10)0.3145 (6)0.6312 (5)0.096 (3)
H40A0.63550.34850.65210.144*
H40B0.79940.29330.68980.144*
H40C0.65290.27230.59120.144*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.096 (3)0.043 (2)0.043 (2)0.015 (2)0.019 (2)0.0018 (18)
O20.054 (2)0.0374 (19)0.0374 (17)0.0000 (16)0.0084 (15)0.0019 (16)
O30.127 (4)0.087 (4)0.054 (3)0.029 (3)0.035 (3)0.004 (2)
O40.086 (3)0.068 (3)0.037 (2)0.010 (2)0.003 (2)0.0025 (18)
O50.0404 (19)0.062 (2)0.046 (2)0.0083 (17)0.0171 (15)0.0095 (17)
O60.079 (3)0.055 (2)0.084 (3)0.013 (2)0.031 (2)0.001 (2)
O70.078 (3)0.076 (3)0.071 (3)0.014 (2)0.026 (2)0.014 (2)
O80.179 (6)0.087 (3)0.061 (3)0.048 (4)0.045 (3)0.012 (3)
C10.087 (5)0.041 (3)0.057 (4)0.007 (3)0.026 (3)0.002 (3)
C20.128 (6)0.046 (4)0.053 (3)0.006 (4)0.033 (4)0.005 (3)
C30.097 (5)0.052 (4)0.043 (3)0.010 (3)0.027 (3)0.009 (3)
C40.061 (3)0.048 (3)0.034 (3)0.014 (3)0.012 (2)0.005 (2)
C50.047 (3)0.053 (3)0.033 (3)0.013 (3)0.001 (2)0.000 (2)
C60.045 (3)0.044 (3)0.036 (3)0.003 (2)0.001 (2)0.000 (2)
C70.038 (3)0.037 (3)0.040 (3)0.008 (2)0.010 (2)0.004 (2)
C80.042 (3)0.036 (3)0.038 (3)0.006 (2)0.010 (2)0.000 (2)
C90.054 (3)0.040 (3)0.037 (3)0.004 (2)0.013 (2)0.003 (2)
C100.038 (3)0.034 (3)0.050 (3)0.002 (2)0.008 (2)0.004 (2)
C110.046 (3)0.050 (3)0.049 (3)0.002 (3)0.002 (3)0.005 (3)
C120.060 (4)0.057 (4)0.051 (3)0.003 (3)0.004 (3)0.005 (3)
C130.040 (3)0.045 (3)0.043 (3)0.006 (2)0.013 (2)0.004 (2)
C140.062 (4)0.041 (3)0.057 (3)0.005 (3)0.028 (3)0.002 (3)
C150.065 (4)0.050 (3)0.069 (4)0.011 (3)0.021 (3)0.006 (3)
C160.057 (4)0.057 (4)0.062 (4)0.009 (3)0.001 (3)0.010 (3)
C170.055 (3)0.049 (3)0.054 (3)0.002 (3)0.030 (3)0.005 (3)
C180.038 (3)0.047 (3)0.071 (4)0.000 (2)0.027 (3)0.003 (3)
C190.046 (3)0.062 (4)0.079 (4)0.009 (3)0.018 (3)0.004 (3)
C200.098 (6)0.097 (6)0.101 (6)0.006 (5)0.044 (4)0.007 (5)
C210.101 (4)0.055 (3)0.063 (3)0.005 (3)0.024 (3)0.005 (3)
C220.107 (4)0.083 (4)0.079 (4)0.011 (4)0.020 (3)0.019 (3)
C230.117 (4)0.096 (4)0.083 (4)0.012 (4)0.015 (4)0.014 (4)
C240.113 (3)0.125 (4)0.102 (4)0.002 (3)0.016 (3)0.025 (3)
C250.113 (3)0.125 (4)0.102 (4)0.002 (3)0.016 (3)0.025 (3)
C260.120 (6)0.121 (6)0.094 (6)0.016 (5)0.035 (5)0.035 (5)
C26'0.120 (6)0.121 (6)0.094 (6)0.016 (5)0.035 (5)0.035 (5)
C270.049 (3)0.040 (3)0.038 (3)0.000 (2)0.010 (2)0.000 (2)
C280.052 (3)0.055 (4)0.052 (3)0.003 (3)0.015 (3)0.005 (3)
C290.070 (4)0.069 (4)0.062 (4)0.014 (3)0.032 (3)0.018 (3)
C300.107 (6)0.108 (6)0.113 (6)0.002 (5)0.076 (5)0.024 (5)
C310.116 (6)0.093 (5)0.049 (4)0.015 (5)0.026 (4)0.007 (4)
C320.086 (5)0.064 (4)0.089 (5)0.006 (4)0.043 (4)0.015 (4)
C330.080 (4)0.066 (4)0.053 (3)0.005 (3)0.030 (3)0.000 (3)
C340.057 (4)0.056 (4)0.068 (4)0.002 (3)0.029 (3)0.006 (3)
C350.030 (3)0.061 (4)0.058 (3)0.002 (3)0.011 (2)0.001 (3)
C360.035 (3)0.063 (4)0.047 (3)0.004 (3)0.007 (2)0.002 (3)
C370.045 (3)0.056 (3)0.058 (3)0.001 (3)0.026 (3)0.004 (3)
C380.057 (4)0.075 (4)0.072 (4)0.017 (3)0.018 (3)0.007 (3)
C390.091 (5)0.100 (6)0.086 (5)0.001 (4)0.046 (4)0.035 (4)
C400.094 (6)0.149 (8)0.044 (3)0.008 (5)0.019 (3)0.020 (4)
Geometric parameters (Å, º) top
O1—C91.357 (6)C22—C231.499 (11)
O1—C11.467 (7)C22—H22A0.9700
O2—C71.374 (6)C22—H22B0.9700
O2—C101.427 (6)C23—C241.286 (10)
O3—C121.225 (6)C23—H230.9300
O4—C51.372 (6)C24—C261.497 (13)
O4—C401.416 (8)C24—C251.516 (11)
O5—C131.424 (6)C24—C26'1.592 (18)
O5—C171.446 (6)C25—H25A0.9600
O6—C141.207 (6)C25—H25B0.9600
O7—C341.332 (7)C25—H25C0.9600
O7—C391.421 (8)C26—H26A0.9600
O8—C341.198 (7)C26—H26B0.9600
C1—C21.478 (8)C26—H26C0.9600
C1—C211.522 (9)C26'—H26D0.9600
C1—C201.524 (10)C26'—H26E0.9600
C2—C31.333 (8)C26'—H26F0.9600
C2—H20.9300C27—C281.512 (8)
C3—C41.448 (8)C27—H27A0.9700
C3—H30.9300C27—H27B0.9700
C4—C51.374 (7)C28—C291.326 (8)
C4—C91.403 (7)C28—H280.9300
C5—C61.404 (7)C29—C301.481 (10)
C6—C71.410 (6)C29—C311.488 (9)
C6—C121.457 (7)C30—H30A0.9600
C7—C81.379 (6)C30—H30B0.9600
C8—C91.372 (7)C30—H30C0.9600
C8—C271.508 (7)C31—H31A0.9600
C10—C111.493 (7)C31—H31B0.9600
C10—C131.532 (7)C31—H31C0.9600
C10—C181.570 (7)C32—H32A0.9600
C11—C161.338 (7)C32—H32B0.9600
C11—C121.468 (8)C32—H32C0.9600
C13—C371.522 (7)C33—H33A0.9600
C13—C141.541 (8)C33—H33B0.9600
C14—C151.523 (8)C33—H33C0.9600
C15—C161.494 (8)C34—C351.470 (8)
C15—C191.539 (9)C35—C361.337 (7)
C15—H150.9800C35—C381.508 (8)
C16—H160.9300C36—C371.484 (7)
C17—C331.521 (8)C36—H360.9300
C17—C321.534 (8)C37—H37A0.9700
C17—C181.543 (8)C37—H37B0.9700
C18—C191.537 (8)C38—H38A0.9600
C18—H180.9800C38—H38B0.9600
C19—H19A0.9700C38—H38C0.9600
C19—H19B0.9700C39—H39A0.9600
C20—H20A0.9600C39—H39B0.9600
C20—H20B0.9600C39—H39C0.9600
C20—H20C0.9600C40—H40A0.9600
C21—C221.524 (10)C40—H40B0.9600
C21—H21A0.9700C40—H40C0.9600
C21—H21B0.9700
C9—O1—C1122.6 (4)C21—C22—H22A108.9
C7—O2—C10122.5 (3)C23—C22—H22B108.9
C5—O4—C40115.9 (5)C21—C22—H22B108.9
C13—O5—C17109.3 (4)H22A—C22—H22B107.7
C34—O7—C39117.9 (5)C24—C23—C22129.9 (9)
O1—C1—C2112.1 (5)C24—C23—H23115.1
O1—C1—C21104.0 (5)C22—C23—H23115.1
C2—C1—C21111.4 (5)C23—C24—C26132.5 (13)
O1—C1—C20107.0 (5)C23—C24—C25121.9 (9)
C2—C1—C20111.0 (6)C26—C24—C25105.6 (12)
C21—C1—C20111.2 (6)C23—C24—C26'101.9 (16)
C3—C2—C1123.2 (5)C26—C24—C26'30.6 (11)
C3—C2—H2118.4C25—C24—C26'136.1 (17)
C1—C2—H2118.4C24—C25—H25A109.5
C2—C3—C4120.5 (5)C24—C25—H25B109.5
C2—C3—H3119.7H25A—C25—H25B109.5
C4—C3—H3119.7C24—C25—H25C109.5
C5—C4—C9117.7 (5)H25A—C25—H25C109.5
C5—C4—C3124.0 (5)H25B—C25—H25C109.5
C9—C4—C3118.3 (5)C24—C26—H26A109.5
O4—C5—C4116.6 (5)C24—C26—H26B109.5
O4—C5—C6121.3 (5)C24—C26—H26C109.5
C4—C5—C6122.0 (4)C24—C26'—H26D109.5
C5—C6—C7117.1 (4)C24—C26'—H26E109.5
C5—C6—C12123.6 (4)H26D—C26'—H26E109.5
C7—C6—C12119.2 (5)C24—C26'—H26F109.5
O2—C7—C8114.6 (4)H26D—C26'—H26F109.5
O2—C7—C6122.7 (4)H26E—C26'—H26F109.5
C8—C7—C6122.6 (4)C8—C27—C28112.0 (4)
C9—C8—C7117.2 (4)C8—C27—H27A109.2
C9—C8—C27120.2 (4)C28—C27—H27A109.2
C7—C8—C27122.6 (4)C8—C27—H27B109.2
O1—C9—C8115.9 (4)C28—C27—H27B109.2
O1—C9—C4120.7 (5)H27A—C27—H27B107.9
C8—C9—C4123.3 (5)C29—C28—C27128.5 (5)
O2—C10—C11114.1 (4)C29—C28—H28115.7
O2—C10—C13111.9 (4)C27—C28—H28115.7
C11—C10—C13109.5 (4)C28—C29—C30120.4 (7)
O2—C10—C18107.7 (4)C28—C29—C31123.8 (6)
C11—C10—C18115.6 (4)C30—C29—C31115.7 (6)
C13—C10—C1896.8 (4)C29—C30—H30A109.5
C16—C11—C12122.6 (5)C29—C30—H30B109.5
C16—C11—C10114.8 (5)H30A—C30—H30B109.5
C12—C11—C10122.0 (5)C29—C30—H30C109.5
O3—C12—C6123.9 (5)H30A—C30—H30C109.5
O3—C12—C11119.3 (5)H30B—C30—H30C109.5
C6—C12—C11116.7 (4)C29—C31—H31A109.5
O5—C13—C37110.0 (4)C29—C31—H31B109.5
O5—C13—C10105.1 (4)H31A—C31—H31B109.5
C37—C13—C10116.9 (4)C29—C31—H31C109.5
O5—C13—C14108.1 (4)H31A—C31—H31C109.5
C37—C13—C14110.3 (4)H31B—C31—H31C109.5
C10—C13—C14106.0 (4)C17—C32—H32A109.5
O6—C14—C15123.0 (5)C17—C32—H32B109.5
O6—C14—C13122.8 (5)H32A—C32—H32B109.5
C15—C14—C13114.3 (5)C17—C32—H32C109.5
C16—C15—C14102.4 (5)H32A—C32—H32C109.5
C16—C15—C19105.9 (5)H32B—C32—H32C109.5
C14—C15—C19109.1 (5)C17—C33—H33A109.5
C16—C15—H15112.9C17—C33—H33B109.5
C14—C15—H15112.9H33A—C33—H33B109.5
C19—C15—H15112.9C17—C33—H33C109.5
C11—C16—C15115.0 (5)H33A—C33—H33C109.5
C11—C16—H16122.5H33B—C33—H33C109.5
C15—C16—H16122.5O8—C34—O7120.5 (6)
O5—C17—C33108.3 (4)O8—C34—C35127.4 (6)
O5—C17—C32106.8 (5)O7—C34—C35112.0 (6)
C33—C17—C32108.0 (5)C36—C35—C34122.2 (5)
O5—C17—C18104.9 (4)C36—C35—C38120.9 (5)
C33—C17—C18111.9 (5)C34—C35—C38116.9 (5)
C32—C17—C18116.5 (5)C35—C36—C37129.3 (5)
C19—C18—C17116.1 (5)C35—C36—H36115.3
C19—C18—C10106.6 (4)C37—C36—H36115.3
C17—C18—C10102.6 (4)C36—C37—C13115.4 (4)
C19—C18—H18110.4C36—C37—H37A108.4
C17—C18—H18110.4C13—C37—H37A108.4
C10—C18—H18110.4C36—C37—H37B108.4
C18—C19—C15110.4 (5)C13—C37—H37B108.4
C18—C19—H19A109.6H37A—C37—H37B107.5
C15—C19—H19A109.6C35—C38—H38A109.5
C18—C19—H19B109.6C35—C38—H38B109.5
C15—C19—H19B109.6H38A—C38—H38B109.5
H19A—C19—H19B108.1C35—C38—H38C109.5
C1—C20—H20A109.5H38A—C38—H38C109.5
C1—C20—H20B109.5H38B—C38—H38C109.5
H20A—C20—H20B109.5O7—C39—H39A109.5
C1—C20—H20C109.5O7—C39—H39B109.5
H20A—C20—H20C109.5H39A—C39—H39B109.5
H20B—C20—H20C109.5O7—C39—H39C109.5
C1—C21—C22114.3 (6)H39A—C39—H39C109.5
C1—C21—H21A108.7H39B—C39—H39C109.5
C22—C21—H21A108.7O4—C40—H40A109.5
C1—C21—H21B108.7O4—C40—H40B109.5
C22—C21—H21B108.7H40A—C40—H40B109.5
H21A—C21—H21B107.6O4—C40—H40C109.5
C23—C22—C21113.5 (6)H40A—C40—H40C109.5
C23—C22—H22A108.9H40B—C40—H40C109.5
C9—O1—C1—C219.3 (8)C11—C10—C13—C3773.1 (5)
C9—O1—C1—C21139.7 (5)C18—C10—C13—C37166.6 (4)
C9—O1—C1—C20102.6 (6)O2—C10—C13—C14177.8 (4)
O1—C1—C2—C314.1 (9)C11—C10—C13—C1450.3 (5)
C21—C1—C2—C3130.0 (7)C18—C10—C13—C1470.0 (4)
C20—C1—C2—C3105.5 (8)O5—C13—C14—O674.4 (6)
C1—C2—C3—C44.2 (10)C37—C13—C14—O645.8 (7)
C2—C3—C4—C5176.9 (6)C10—C13—C14—O6173.3 (5)
C2—C3—C4—C92.2 (9)O5—C13—C14—C15105.3 (5)
C40—O4—C5—C4108.0 (6)C37—C13—C14—C15134.4 (5)
C40—O4—C5—C676.5 (7)C10—C13—C14—C156.9 (6)
C9—C4—C5—O4176.0 (5)O6—C14—C15—C16120.0 (6)
C3—C4—C5—O45.0 (8)C13—C14—C15—C1660.2 (6)
C9—C4—C5—C60.5 (8)O6—C14—C15—C19128.1 (6)
C3—C4—C5—C6179.6 (5)C13—C14—C15—C1951.7 (6)
O4—C5—C6—C7175.6 (5)C12—C11—C16—C15174.8 (5)
C4—C5—C6—C70.3 (8)C10—C11—C16—C153.4 (8)
O4—C5—C6—C122.0 (8)C14—C15—C16—C1159.6 (7)
C4—C5—C6—C12177.2 (5)C19—C15—C16—C1154.7 (7)
C10—O2—C7—C8168.6 (4)C13—O5—C17—C33123.1 (5)
C10—O2—C7—C614.4 (7)C13—O5—C17—C32120.8 (5)
C5—C6—C7—O2178.6 (5)C13—O5—C17—C183.4 (5)
C12—C6—C7—O20.9 (7)O5—C17—C18—C1991.1 (5)
C5—C6—C7—C81.8 (7)C33—C17—C18—C19151.7 (5)
C12—C6—C7—C8175.9 (5)C32—C17—C18—C1926.8 (7)
O2—C7—C8—C9179.7 (4)O5—C17—C18—C1024.8 (5)
C6—C7—C8—C93.3 (7)C33—C17—C18—C1092.4 (5)
O2—C7—C8—C271.5 (7)C32—C17—C18—C10142.7 (5)
C6—C7—C8—C27175.6 (5)O2—C10—C18—C19162.8 (4)
C1—O1—C9—C8169.3 (5)C11—C10—C18—C1933.8 (6)
C1—O1—C9—C414.7 (8)C13—C10—C18—C1981.6 (5)
C7—C8—C9—O1179.4 (4)O2—C10—C18—C1774.7 (5)
C27—C8—C9—O10.5 (7)C11—C10—C18—C17156.4 (4)
C7—C8—C9—C43.5 (8)C13—C10—C18—C1740.9 (4)
C27—C8—C9—C4175.4 (5)C17—C18—C19—C1589.9 (6)
C5—C4—C9—O1177.9 (5)C10—C18—C19—C1523.7 (6)
C3—C4—C9—O13.0 (8)C16—C15—C19—C1868.9 (6)
C5—C4—C9—C82.2 (8)C14—C15—C19—C1840.7 (6)
C3—C4—C9—C8178.7 (5)O1—C1—C21—C2263.2 (7)
C7—O2—C10—C1119.5 (6)C2—C1—C21—C2257.6 (8)
C7—O2—C10—C13105.5 (5)C20—C1—C21—C22178.1 (6)
C7—O2—C10—C18149.3 (4)C1—C21—C22—C23177.0 (6)
O2—C10—C11—C16177.5 (5)C21—C22—C23—C24111.6 (10)
C13—C10—C11—C1656.3 (6)C22—C23—C24—C26177.2 (11)
C18—C10—C11—C1651.7 (7)C22—C23—C24—C255.6 (15)
O2—C10—C11—C1211.1 (7)C22—C23—C24—C26'176.9 (15)
C13—C10—C11—C12115.1 (5)C9—C8—C27—C2883.4 (6)
C18—C10—C11—C12136.8 (5)C7—C8—C27—C2895.4 (6)
C5—C6—C12—O34.4 (9)C8—C27—C28—C29157.5 (6)
C7—C6—C12—O3173.1 (6)C27—C28—C29—C30177.5 (6)
C5—C6—C12—C11173.9 (5)C27—C28—C29—C311.7 (10)
C7—C6—C12—C118.6 (7)C39—O7—C34—O81.5 (9)
C16—C11—C12—O39.9 (9)C39—O7—C34—C35178.6 (5)
C10—C11—C12—O3179.3 (6)O8—C34—C35—C364.4 (10)
C16—C11—C12—C6168.5 (6)O7—C34—C35—C36172.5 (5)
C10—C11—C12—C62.3 (8)O8—C34—C35—C38177.9 (6)
C17—O5—C13—C37158.2 (4)O7—C34—C35—C385.2 (7)
C17—O5—C13—C1031.5 (5)C34—C35—C36—C375.3 (8)
C17—O5—C13—C1481.3 (5)C38—C35—C36—C37177.1 (5)
O2—C10—C13—O567.9 (5)C35—C36—C37—C13140.1 (6)
C11—C10—C13—O5164.6 (4)O5—C13—C37—C3645.3 (6)
C18—C10—C13—O544.3 (4)C10—C13—C37—C3674.4 (6)
O2—C10—C13—C3754.4 (6)C14—C13—C37—C36164.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O8i0.932.533.400 (8)156
C31—H31C···O6ii0.962.583.535 (8)176
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC40H48O8
Mr656.78
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)7.865 (3), 17.017 (7), 13.711 (6)
β (°) 105.322 (6)
V3)1769.8 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.54 × 0.40 × 0.27
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.955, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
8951, 3235, 2055
Rint0.045
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.153, 1.05
No. of reflections3235
No. of parameters432
No. of restraints125
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.48
Absolute structureFlack (1983), with how many Friedel pairs?

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O8i0.932.533.400 (8)155.5
C31—H31C···O6ii0.962.583.535 (8)175.6
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y+1/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds