Roridin H

Gai, Y.; Zhao, L.-L.; Hu, C.-Q.; Zhang, H.-P.

doi:10.1107/S1600536807024786

Roridin H

Y. Gai, L.-L. Zhao, C.-Q. Hu and H.-P. Zhang

In the molecule of the title compound, C₂₉H₃₆O₈, the five-membered rings adopt envelope conformations, while the six-membered rings have twist and chair conformations. The five-membered rings also have pseudo-mirror planes, while the six-membered rings have pseudo-twofold axes. In the crystal structure, intra- and intermolecular C—H

O hydrogen bonds cause the formation of a network structure. This study establishes the relative configuration of the compound.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024786/hk2249sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024786/hk2249Isup2.hkl Contains datablock I

CCDC reference: 632479

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.051
wR factor = 0.128
Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.24 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30B   ..  O29     ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2'A   ..  O29     ..       2.63 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

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           27.00
           From the CIF: _reflns_number_total               3012
           Count of symmetry unique reflns         3054
           Completeness (_total/calc)             98.62%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24A   = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

Comment top

Macrocyclic trichothecenes have attracted considerable interest mainly due to their potent biological activity, such as cancer prevention (Amagata et al., 2003), cytotoxicity (Namikoshi et al., 2001; Alvi et al., 2002; Xu et al., 2006) and phytotoxicity (Abbas et al., 2002). Knowledge of the three-dimensional structure of these compounds is important in order to establish structure-activity relationships (Kaneko et al., 1982). We herein report the crystal structure of roridin H, (I), a bioactive macrocyclic trichothecene with systematic name Spiro[7,10-epoxy-17,19-methano-1H,3H,9H,24H-[1,6,12]trioxacyclo- nonadecino[3,\4 - d][1]benzopyran-18(19H),2'-oxirane], verrucarin A derivative.

In the molecule of the title compound, (I), the bond lengths and angles are within normal ranges (Allen et al., 1987; Jarvis & Midiwo, 1982). Rings A (O8/O27/C7/C9/C10) and B (C1'/C17A/C17—C19) have envelope conformations with atoms C9 and C18 displaced by -0.556 (3) Å and -0.671 (3) Å from the planes of the other four ring atoms, respectively. Rings C (C20A/C24A/C21—C24) and D (O20/C17A/C18/C19/C20A/C24A) are not planar, having total puckering amplitudes, Q_T, of 0.464 (3) and 0.637 (3) Å, respectively and twist and chair conformations φ = 91.55 (6)°, θ = 131.26 (4)° and φ = 66.76 (3)°, θ = 161.87 (3)° (Cremer & Pople, 1975). The five-membered rings A and B have pseudo mirror planes running through C9 and the mid-point of C7—O27 bond (for ring A) and C18 and the mid-point of C1'-C17 bond (for ring B), while the six-membered rings C and D have pseudo twofold axes passing through the mid-points of C18—C19 and C20A—C24A bonds (for ring C) and C21—C22 and C24—C24A bonds (for ring D), as can be deduced from the torsion angles (Table 1).

There is no significant anomalous dispersion for the determination of the absolute configuration. However, the relative configuration for the molecule was definitely determined and the absolute configurations in the trichothecene moiety were certain (Shen et al., 2006), thus C17R, C17aS, C18S, C19R, C20aR, C24aR were presumed in (I) and the absolute configurations of C9S and C10S would be deduced. This absolute configuration of the molecule needs to be verified.

In the crystal structure, the weak intra- and intermolecular C—H···O hydrogen bonds (Table 2) cause to the formation of a network structure (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general backgroud, see: Amagata et al. (2003); Namikoshi et al. (2001); Alvi et al. (2002); Xu et al. (2006); Abbas et al. (2002); Kaneko et al. (1982); Allen et al. (1987); Jarvis & Midiwo (1982); Cremer & Pople (1975). For related literature, see: Shen et al. (2006).

Experimental top

The title compound, (I), was isolated from 3L culture of the fungal strain S_1–1 (a Myrothecium sp.), affording 3.2 mg by repeated column chromatography on Sephadex LH-20 and Silica gel. Pyricularia oryzae was grown on a slant culture medium consisting of yeast extract 0.2%, soluble starch 1% and agar 2% at 300 K for 12~14 days, using as the indicator organism of the antifungal activity. Single crystals suitable for X-ray analysis were obtained from acetone by slow evaporation at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Figures top

	Fig. 1. The molecular structure of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

(I) top

Crystal data top

C₂₉H₃₆O₈	F(000) = 548
M_r = 512.58	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 940 reflections
a = 10.259 (6) Å	θ = 2.6–23.2°
b = 8.989 (5) Å	µ = 0.09 mm⁻¹
c = 14.290 (8) Å	T = 293 K
β = 96.410 (7)°	Prism, colorless
V = 1309.6 (13) Å³	0.25 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3012 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.977, T_max = 0.981	k = −10→11
6524 measured reflections	l = −12→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0693P)² + 0.0186P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3012 reflections	Δρ_max = 0.23 e Å⁻³
338 parameters	Δρ_min = −0.18 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with no Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₂₉H₃₆O₈	V = 1309.6 (13) Å³
M_r = 512.58	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.259 (6) Å	µ = 0.09 mm⁻¹
b = 8.989 (5) Å	T = 293 K
c = 14.290 (8) Å	0.25 × 0.20 × 0.20 mm
β = 96.410 (7)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3012 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2555 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.044
6524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.128	Δρ_max = 0.23 e Å⁻³
S = 1.09	Δρ_min = −0.18 e Å⁻³
3012 reflections	Absolute structure: Flack (1983), with no Friedel pairs
338 parameters	Absolute structure parameter: 0 (10)
1 restraint

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

	x	y	z	U_iso*/U_eq
C1	0.5453 (3)	0.3762 (3)	0.6923 (2)	0.0384 (6)
H1A	0.6405	0.3773	0.7013	0.046*
H1B	0.5165	0.4447	0.6418	0.046*
O2	0.4955 (2)	0.4239 (2)	0.77738 (14)	0.0419 (5)
C3	0.5125 (3)	0.5676 (4)	0.7996 (2)	0.0483 (7)
C4	0.4303 (4)	0.6080 (4)	0.8736 (2)	0.0500 (8)
H4	0.3609	0.5443	0.8814	0.060*
C5	0.4437 (4)	0.7245 (4)	0.9306 (2)	0.0502 (8)
C6	0.3512 (4)	0.7469 (4)	1.0042 (2)	0.0572 (9)
H6A	0.4028	0.7610	1.0647	0.069*
H6B	0.3003	0.6566	1.0083	0.069*
C7	0.2570 (4)	0.8766 (5)	0.9873 (3)	0.0602 (9)
H7	0.3071	0.9697	0.9901	0.072*
O8	0.1679 (3)	0.8806 (4)	1.05537 (18)	0.0714 (8)
C9	0.0537 (4)	0.8063 (5)	1.0137 (3)	0.0647 (10)
H9	0.0685	0.6986	1.0171	0.078*
C10	0.0486 (4)	0.8563 (5)	0.9119 (3)	0.0619 (10)
H10	0.0105	0.9563	0.9061	0.074*
C11	−0.0257 (4)	0.7571 (5)	0.8415 (3)	0.0616 (10)
H11	−0.1158	0.7491	0.8433	0.074*
C12	0.0264 (4)	0.6798 (4)	0.7767 (2)	0.0539 (8)
H12	0.1159	0.6887	0.7727	0.065*
C13	−0.0495 (3)	0.5820 (5)	0.7119 (2)	0.0564 (9)
H13	−0.1394	0.5805	0.7153	0.068*
C14	−0.0053 (3)	0.4928 (5)	0.6470 (2)	0.0537 (8)
H14	−0.0666	0.4379	0.6085	0.064*
C15	0.1339 (3)	0.4763 (4)	0.6332 (2)	0.0448 (7)
O16	0.1512 (2)	0.3506 (3)	0.58600 (15)	0.0472 (5)
C17	0.2858 (3)	0.3108 (4)	0.5746 (2)	0.0391 (6)
H17	0.3405	0.3999	0.5726	0.047*
C17A	0.3426 (3)	0.2037 (3)	0.6553 (2)	0.0354 (6)
C18	0.3089 (3)	0.0526 (4)	0.6096 (2)	0.0411 (7)
C19	0.3448 (3)	0.0706 (4)	0.5121 (2)	0.0431 (7)
H19	0.3056	−0.0084	0.4709	0.052*
O20	0.4846 (2)	0.0672 (2)	0.51674 (14)	0.0411 (5)
C20A	0.5468 (3)	0.1918 (3)	0.5675 (2)	0.0349 (6)
H20A	0.5295	0.2816	0.5292	0.042*
C21	0.6912 (3)	0.1586 (4)	0.5744 (2)	0.0445 (7)
H21	0.7318	0.1665	0.5196	0.053*
C22	0.7645 (3)	0.1194 (4)	0.6515 (3)	0.0499 (8)
C23	0.7103 (3)	0.1063 (5)	0.7434 (2)	0.0562 (9)
H23A	0.7409	0.1900	0.7828	0.067*
H23B	0.7443	0.0163	0.7747	0.067*
C24	0.5609 (3)	0.1021 (4)	0.7350 (2)	0.0427 (7)
H24A	0.5324	0.1199	0.7965	0.051*
H24B	0.5311	0.0037	0.7145	0.051*
C24A	0.4972 (3)	0.2185 (3)	0.66494 (18)	0.0331 (6)
O25	0.5840 (4)	0.6482 (3)	0.7619 (2)	0.0807 (10)
C26	0.5507 (5)	0.8364 (6)	0.9300 (3)	0.0880 (16)
H26A	0.6065	0.8317	0.9885	0.132*
H26B	0.5132	0.9341	0.9222	0.132*
H26C	0.6012	0.8155	0.8789	0.132*
O27	0.1828 (3)	0.8649 (4)	0.89813 (17)	0.0668 (7)
C28	−0.0622 (5)	0.8447 (7)	1.0651 (3)	0.0907 (16)
H28A	−0.0418	0.8231	1.1309	0.136*
H28B	−0.1367	0.7868	1.0401	0.136*
H28C	−0.0821	0.9485	1.0571	0.136*
O29	0.2216 (3)	0.5599 (3)	0.66110 (19)	0.0610 (7)
C30	0.2802 (3)	0.2202 (4)	0.7473 (2)	0.0437 (7)
H30A	0.1910	0.1864	0.7380	0.066*
H30B	0.2822	0.3229	0.7659	0.066*
H30C	0.3284	0.1618	0.7956	0.066*
O31	0.1813 (2)	−0.0075 (3)	0.6160 (2)	0.0624 (7)
C32	0.9084 (3)	0.0833 (6)	0.6520 (3)	0.0743 (12)
H32A	0.9217	−0.0214	0.6621	0.111*
H32B	0.9582	0.1377	0.7016	0.111*
H32C	0.9368	0.1108	0.5926	0.111*
C1'	0.2847 (3)	0.2206 (4)	0.4835 (2)	0.0504 (8)
H1'A	0.1957	0.2083	0.4537	0.061*
H1'B	0.3359	0.2704	0.4397	0.061*
C2'	0.2946 (4)	−0.0883 (4)	0.6567 (3)	0.0586 (9)
H2'A	0.3185	−0.1781	0.6250	0.070*
H2'B	0.3121	−0.0906	0.7248	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0381 (15)	0.0391 (15)	0.0392 (14)	−0.0056 (12)	0.0091 (12)	−0.0044 (12)
O2	0.0493 (12)	0.0388 (11)	0.0389 (11)	−0.0044 (9)	0.0111 (9)	−0.0051 (9)
C3	0.059 (2)	0.0400 (17)	0.0468 (17)	−0.0055 (16)	0.0098 (14)	−0.0033 (14)
C4	0.063 (2)	0.0423 (18)	0.0467 (17)	−0.0073 (15)	0.0149 (15)	−0.0019 (14)
C5	0.069 (2)	0.0438 (18)	0.0380 (15)	0.0022 (16)	0.0067 (15)	−0.0003 (14)
C6	0.085 (3)	0.050 (2)	0.0377 (16)	0.0062 (18)	0.0119 (16)	−0.0040 (14)
C7	0.081 (3)	0.049 (2)	0.0531 (19)	0.0025 (19)	0.0179 (18)	−0.0097 (17)
O8	0.087 (2)	0.0735 (19)	0.0569 (14)	0.0052 (16)	0.0204 (14)	−0.0208 (14)
C9	0.086 (3)	0.054 (2)	0.058 (2)	0.006 (2)	0.025 (2)	−0.0090 (18)
C10	0.077 (3)	0.051 (2)	0.060 (2)	0.0157 (19)	0.0180 (19)	−0.0035 (18)
C11	0.065 (2)	0.061 (2)	0.059 (2)	0.0185 (19)	0.0129 (18)	−0.0032 (18)
C12	0.057 (2)	0.057 (2)	0.0486 (18)	0.0120 (17)	0.0098 (15)	0.0035 (15)
C13	0.0445 (18)	0.070 (2)	0.0542 (19)	0.0191 (17)	0.0031 (15)	−0.0016 (18)
C14	0.0450 (18)	0.056 (2)	0.0578 (19)	0.0118 (16)	−0.0030 (15)	−0.0070 (17)
C15	0.0484 (18)	0.0376 (16)	0.0489 (17)	0.0076 (14)	0.0074 (14)	−0.0005 (14)
O16	0.0343 (11)	0.0468 (13)	0.0600 (13)	0.0067 (9)	0.0024 (9)	−0.0108 (11)
C17	0.0328 (14)	0.0404 (16)	0.0443 (15)	0.0054 (12)	0.0054 (12)	−0.0030 (12)
C17A	0.0301 (14)	0.0363 (16)	0.0411 (14)	−0.0011 (11)	0.0105 (11)	−0.0040 (12)
C18	0.0296 (14)	0.0370 (16)	0.0575 (17)	−0.0040 (12)	0.0084 (12)	−0.0109 (13)
C19	0.0379 (15)	0.0452 (17)	0.0458 (16)	0.0007 (13)	0.0022 (12)	−0.0164 (14)
O20	0.0369 (11)	0.0402 (12)	0.0475 (11)	0.0019 (9)	0.0097 (8)	−0.0121 (10)
C20A	0.0335 (14)	0.0331 (14)	0.0393 (14)	−0.0013 (11)	0.0099 (11)	−0.0043 (11)
C21	0.0379 (16)	0.0455 (18)	0.0536 (18)	−0.0036 (13)	0.0203 (14)	−0.0064 (14)
C22	0.0326 (15)	0.0478 (19)	0.070 (2)	−0.0011 (14)	0.0100 (15)	−0.0031 (16)
C23	0.0418 (17)	0.065 (2)	0.060 (2)	0.0035 (16)	−0.0034 (15)	0.0081 (18)
C24	0.0410 (16)	0.0460 (18)	0.0418 (15)	−0.0005 (13)	0.0080 (12)	0.0057 (13)
C24A	0.0326 (13)	0.0334 (15)	0.0344 (13)	−0.0013 (11)	0.0085 (11)	−0.0009 (11)
O25	0.112 (2)	0.0499 (16)	0.090 (2)	−0.0335 (16)	0.0539 (19)	−0.0207 (14)
C26	0.117 (4)	0.074 (3)	0.078 (3)	−0.032 (3)	0.032 (3)	−0.033 (2)
O27	0.0792 (18)	0.0735 (18)	0.0496 (13)	−0.0002 (15)	0.0160 (12)	0.0037 (13)
C28	0.098 (3)	0.103 (4)	0.078 (3)	0.009 (3)	0.037 (3)	−0.019 (3)
O29	0.0579 (15)	0.0452 (14)	0.0838 (17)	−0.0043 (12)	0.0257 (13)	−0.0147 (13)
C30	0.0364 (15)	0.0485 (18)	0.0487 (17)	−0.0028 (13)	0.0164 (13)	−0.0059 (14)
O31	0.0411 (13)	0.0580 (15)	0.0908 (18)	−0.0157 (12)	0.0191 (12)	−0.0186 (14)
C32	0.0348 (18)	0.089 (3)	0.100 (3)	0.010 (2)	0.0119 (19)	0.005 (3)
C1'	0.0440 (17)	0.059 (2)	0.0469 (17)	0.0107 (16)	0.0000 (13)	−0.0079 (15)
C2'	0.056 (2)	0.043 (2)	0.079 (3)	−0.0100 (16)	0.0181 (18)	−0.0061 (18)

Geometric parameters (Å, º) top

C1—O2	1.436 (3)	C17A—C30	1.532 (4)
C1—C24A	1.538 (4)	C17A—C24A	1.582 (4)
C1—H1A	0.9700	C18—O31	1.428 (4)
C1—H1B	0.9700	C18—C2'	1.449 (5)
O2—C3	1.337 (4)	C18—C19	1.489 (4)
C3—O25	1.201 (4)	C19—O20	1.428 (4)
C3—C4	1.470 (5)	C19—C1'	1.520 (5)
C4—C5	1.324 (5)	C19—H19	0.9800
C4—H4	0.9300	O20—C20A	1.444 (3)
C5—C26	1.489 (6)	C20A—C21	1.504 (4)
C5—C6	1.507 (5)	C20A—C24A	1.553 (4)
C6—C7	1.517 (6)	C20A—H20A	0.9800
C6—H6A	0.9700	C21—C22	1.311 (5)
C6—H6B	0.9700	C21—H21	0.9300
C7—O8	1.407 (5)	C22—C23	1.487 (5)
C7—O27	1.414 (5)	C22—C32	1.511 (5)
C7—H7	0.9800	C23—C24	1.524 (5)
O8—C9	1.421 (5)	C23—H23A	0.9700
C9—C28	1.506 (6)	C23—H23B	0.9700
C9—C10	1.518 (5)	C24—C24A	1.542 (4)
C9—H9	0.9800	C24—H24A	0.9700
C10—O27	1.415 (5)	C24—H24B	0.9700
C10—C11	1.489 (6)	C26—H26A	0.9599
C10—H10	0.9800	C26—H26B	0.9599
C11—C12	1.317 (5)	C26—H26C	0.9599
C11—H11	0.9300	C28—H28A	0.9599
C12—C13	1.441 (5)	C28—H28B	0.9599
C12—H12	0.9300	C28—H28C	0.9599
C13—C14	1.341 (5)	C30—H30A	0.9599
C13—H13	0.9300	C30—H30B	0.9599
C14—C15	1.471 (5)	C30—H30C	0.9599
C14—H14	0.9300	O31—C2'	1.437 (5)
C15—O29	1.206 (4)	C32—H32A	0.9599
C15—O16	1.338 (4)	C32—H32B	0.9599
O16—C17	1.453 (3)	C32—H32C	0.9599
C17—C1'	1.533 (4)	C1'—H1'A	0.9700
C17—C17A	1.564 (4)	C1'—H1'B	0.9700
C17—H17	0.9800	C2'—H2'A	0.9700
C17A—C18	1.530 (4)	C2'—H2'B	0.9700

O2—C1—C24A	110.8 (2)	O20—C19—C18	107.8 (2)
O2—C1—H1A	109.5	O20—C19—C1'	114.0 (3)
C24A—C1—H1A	109.5	C18—C19—C1'	102.3 (3)
O2—C1—H1B	109.5	O20—C19—H19	110.8
C24A—C1—H1B	109.5	C18—C19—H19	110.8
H1A—C1—H1B	108.1	C1'—C19—H19	110.8
C3—O2—C1	116.1 (2)	C19—O20—C20A	113.1 (2)
O25—C3—O2	123.1 (3)	O20—C20A—C21	104.8 (2)
O25—C3—C4	127.0 (3)	O20—C20A—C24A	113.6 (2)
O2—C3—C4	109.8 (3)	C21—C20A—C24A	113.0 (2)
C5—C4—C3	127.5 (3)	O20—C20A—H20A	108.4
C5—C4—H4	116.2	C21—C20A—H20A	108.4
C3—C4—H4	116.2	C24A—C20A—H20A	108.4
C4—C5—C26	123.8 (3)	C22—C21—C20A	125.2 (3)
C4—C5—C6	120.3 (3)	C22—C21—H21	117.4
C26—C5—C6	115.8 (3)	C20A—C21—H21	117.4
C5—C6—C7	115.5 (3)	C21—C22—C23	121.9 (3)
C5—C6—H6A	108.4	C21—C22—C32	122.0 (3)
C7—C6—H6A	108.4	C23—C22—C32	116.1 (3)
C5—C6—H6B	108.4	C22—C23—C24	113.8 (3)
C7—C6—H6B	108.4	C22—C23—H23A	108.8
H6A—C6—H6B	107.5	C24—C23—H23A	108.8
O8—C7—O27	107.4 (3)	C22—C23—H23B	108.8
O8—C7—C6	111.1 (3)	C24—C23—H23B	108.8
O27—C7—C6	110.8 (3)	H23A—C23—H23B	107.7
O8—C7—H7	109.2	C23—C24—C24A	112.6 (3)
O27—C7—H7	109.2	C23—C24—H24A	109.1
C6—C7—H7	109.2	C24A—C24—H24A	109.1
C7—O8—C9	105.5 (3)	C23—C24—H24B	109.1
O8—C9—C28	110.3 (3)	C24A—C24—H24B	109.1
O8—C9—C10	101.6 (3)	H24A—C24—H24B	107.8
C28—C9—C10	117.0 (4)	C1—C24A—C24	111.1 (2)
O8—C9—H9	109.2	C1—C24A—C20A	104.0 (2)
C28—C9—H9	109.2	C24—C24A—C20A	108.6 (2)
C10—C9—H9	109.2	C1—C24A—C17A	113.0 (2)
O27—C10—C11	111.8 (3)	C24—C24A—C17A	110.4 (2)
O27—C10—C9	102.7 (3)	C20A—C24A—C17A	109.6 (2)
C11—C10—C9	115.5 (4)	C5—C26—H26A	109.5
O27—C10—H10	108.9	C5—C26—H26B	109.5
C11—C10—H10	108.9	H26A—C26—H26B	109.5
C9—C10—H10	108.9	C5—C26—H26C	109.5
C12—C11—C10	125.0 (4)	H26A—C26—H26C	109.5
C12—C11—H11	117.5	H26B—C26—H26C	109.5
C10—C11—H11	117.5	C7—O27—C10	108.2 (3)
C11—C12—C13	122.8 (4)	C9—C28—H28A	109.5
C11—C12—H12	118.6	C9—C28—H28B	109.5
C13—C12—H12	118.6	H28A—C28—H28B	109.5
C14—C13—C12	127.5 (3)	C9—C28—H28C	109.5
C14—C13—H13	116.2	H28A—C28—H28C	109.5
C12—C13—H13	116.2	H28B—C28—H28C	109.5
C13—C14—C15	124.1 (3)	C17A—C30—H30A	109.5
C13—C14—H14	117.9	C17A—C30—H30B	109.5
C15—C14—H14	117.9	H30A—C30—H30B	109.5
O29—C15—O16	123.8 (3)	C17A—C30—H30C	109.5
O29—C15—C14	126.4 (3)	H30A—C30—H30C	109.5
O16—C15—C14	109.8 (3)	H30B—C30—H30C	109.5
C15—O16—C17	116.5 (2)	C18—O31—C2'	60.8 (2)
O16—C17—C1'	108.0 (2)	C22—C32—H32A	109.5
O16—C17—C17A	110.4 (2)	C22—C32—H32B	109.5
C1'—C17—C17A	105.5 (3)	H32A—C32—H32B	109.5
O16—C17—H17	110.9	C22—C32—H32C	109.5
C1'—C17—H17	110.9	H32A—C32—H32C	109.5
C17A—C17—H17	110.9	H32B—C32—H32C	109.5
C18—C17A—C30	110.9 (2)	C19—C1'—C17	106.0 (3)
C18—C17A—C17	100.6 (2)	C19—C1'—H1'A	110.5
C30—C17A—C17	114.6 (2)	C17—C1'—H1'A	110.5
C18—C17A—C24A	106.7 (2)	C19—C1'—H1'B	110.5
C30—C17A—C24A	115.3 (2)	C17—C1'—H1'B	110.5
C17—C17A—C24A	107.4 (2)	H1'A—C1'—H1'B	108.7
O31—C18—C2'	59.9 (2)	O31—C2'—C18	59.3 (2)
O31—C18—C19	115.2 (3)	O31—C2'—H2'A	117.8
C2'—C18—C19	125.3 (3)	C18—C2'—H2'A	117.8
O31—C18—C17A	118.2 (2)	O31—C2'—H2'B	117.8
C2'—C18—C17A	127.4 (3)	C18—C2'—H2'B	117.8
C19—C18—C17A	103.6 (3)	H2'A—C2'—H2'B	115.0

C24A—C1—O2—C3	−169.2 (3)	O31—C18—C19—C1'	84.4 (3)
C1—O2—C3—O25	−12.7 (5)	C2'—C18—C19—C1'	154.2 (3)
C1—O2—C3—C4	166.3 (3)	C17A—C18—C19—C1'	−46.2 (3)
O25—C3—C4—C5	−20.0 (7)	C18—C19—O20—C20A	−65.4 (3)
O2—C3—C4—C5	161.0 (3)	C1'—C19—O20—C20A	47.4 (3)
C3—C4—C5—C26	−1.4 (6)	C19—O20—C20A—C21	173.5 (2)
C3—C4—C5—C6	−178.8 (4)	C19—O20—C20A—C24A	49.6 (3)
C4—C5—C6—C7	−110.5 (4)	O20—C20A—C21—C22	−108.2 (3)
C26—C5—C6—C7	72.0 (5)	C24A—C20A—C21—C22	16.0 (4)
C5—C6—C7—O8	175.1 (3)	C20A—C21—C22—C23	−1.3 (5)
C5—C6—C7—O27	55.7 (5)	C20A—C21—C22—C32	178.1 (4)
O27—C7—O8—C9	25.6 (4)	C21—C22—C23—C24	15.1 (5)
C6—C7—O8—C9	−95.7 (4)	C32—C22—C23—C24	−164.3 (4)
C7—O8—C9—C28	−161.9 (4)	C22—C23—C24—C24A	−43.9 (4)
C7—O8—C9—C10	−37.1 (4)	O2—C1—C24A—C24	−69.2 (3)
O8—C9—C10—O27	35.1 (4)	O2—C1—C24A—C20A	174.1 (2)
C28—C9—C10—O27	155.3 (4)	O2—C1—C24A—C17A	55.4 (3)
O8—C9—C10—C11	157.1 (3)	C23—C24—C24A—C1	−56.7 (3)
C28—C9—C10—C11	−82.7 (5)	C23—C24—C24A—C20A	57.1 (3)
O27—C10—C11—C12	3.3 (6)	C23—C24—C24A—C17A	177.2 (3)
C9—C10—C11—C12	−113.6 (4)	O20—C20A—C24A—C1	−164.7 (2)
C10—C11—C12—C13	178.2 (4)	C21—C20A—C24A—C1	76.1 (3)
C11—C12—C13—C14	−176.1 (4)	O20—C20A—C24A—C24	77.0 (3)
C12—C13—C14—C15	2.1 (6)	C21—C20A—C24A—C24	−42.3 (3)
C13—C14—C15—O29	−17.4 (6)	O20—C20A—C24A—C17A	−43.6 (3)
C13—C14—C15—O16	161.1 (4)	C21—C20A—C24A—C17A	−162.9 (2)
O29—C15—O16—C17	4.3 (5)	C18—C17A—C24A—C1	169.1 (2)
C14—C15—O16—C17	−174.2 (3)	C30—C17A—C24A—C1	−67.3 (3)
C15—O16—C17—C1'	−151.5 (3)	C17—C17A—C24A—C1	61.9 (3)
C15—O16—C17—C17A	93.6 (3)	C18—C17A—C24A—C24	−65.9 (3)
O16—C17—C17A—C18	91.9 (3)	C30—C17A—C24A—C24	57.7 (3)
C1'—C17—C17A—C18	−24.5 (3)	C17—C17A—C24A—C24	−173.1 (2)
O16—C17—C17A—C30	−27.1 (3)	C18—C17A—C24A—C20A	53.6 (3)
C1'—C17—C17A—C30	−143.6 (3)	C30—C17A—C24A—C20A	177.3 (2)
O16—C17—C17A—C24A	−156.7 (2)	C17—C17A—C24A—C20A	−53.6 (3)
C1'—C17—C17A—C24A	86.9 (3)	O8—C7—O27—C10	−2.0 (4)
C30—C17A—C18—O31	36.7 (4)	C6—C7—O27—C10	119.5 (4)
C17—C17A—C18—O31	−85.0 (3)	C11—C10—O27—C7	−144.9 (3)
C24A—C17A—C18—O31	163.0 (3)	C9—C10—O27—C7	−20.5 (4)
C30—C17A—C18—C2'	−35.5 (4)	C19—C18—O31—C2'	117.8 (3)
C17—C17A—C18—C2'	−157.2 (3)	C17A—C18—O31—C2'	−119.1 (3)
C24A—C17A—C18—C2'	90.8 (4)	O20—C19—C1'—C17	−86.6 (3)
C30—C17A—C18—C19	165.4 (2)	C18—C19—C1'—C17	29.5 (3)
C17—C17A—C18—C19	43.8 (3)	O16—C17—C1'—C19	−120.6 (3)
C24A—C17A—C18—C19	−68.2 (3)	C17A—C17—C1'—C19	−2.5 (3)
O31—C18—C19—O20	−155.1 (3)	C19—C18—C2'—O31	−101.1 (3)
C2'—C18—C19—O20	−85.3 (4)	C17A—C18—C2'—O31	104.2 (3)
C17A—C18—C19—O20	74.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30B···O2	0.96	2.36	2.864 (4)	112
C30—H30B···O29	0.96	2.64	3.322 (5)	129
C12—H12···O29	0.93	2.33	2.940 (4)	123
C26—H26C···O25	0.96	2.24	2.989 (5)	134
C1—H1B···O20ⁱ	0.97	2.52	3.430 (4)	157
C2′—H2′A···O29ⁱⁱ	0.97	2.63	3.252 (5)	122

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

Experimental details

Crystal data
Chemical formula	C₂₉H₃₆O₈
M_r	512.58
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	10.259 (6), 8.989 (5), 14.290 (8)
β (°)	96.410 (7)
V (Å³)	1309.6 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	6524, 3012, 2555
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.128, 1.09
No. of reflections	3012
No. of parameters	338
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18
Absolute structure	Flack (1983), with no Friedel pairs
Absolute structure parameter	0 (10)

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

Selected torsion angles (º) top

O27—C7—O8—C9	25.6 (4)	C20A—C21—C22—C23	−1.3 (5)
C7—O8—C9—C10	−37.1 (4)	C21—C22—C23—C24	15.1 (5)
O8—C9—C10—O27	35.1 (4)	C22—C23—C24—C24A	−43.9 (4)
C1'—C17—C17A—C18	−24.5 (3)	C23—C24—C24A—C20A	57.1 (3)
C17—C17A—C18—C19	43.8 (3)	C21—C20A—C24A—C24	−42.3 (3)
C24A—C17A—C18—C19	−68.2 (3)	O20—C20A—C24A—C17A	−43.6 (3)
C17A—C18—C19—O20	74.3 (3)	C18—C17A—C24A—C20A	53.6 (3)
C17A—C18—C19—C1'	−46.2 (3)	O8—C7—O27—C10	−2.0 (4)
C18—C19—O20—C20A	−65.4 (3)	C9—C10—O27—C7	−20.5 (4)
C19—O20—C20A—C24A	49.6 (3)	C18—C19—C1'—C17	29.5 (3)
C24A—C20A—C21—C22	16.0 (4)	C17A—C17—C1'—C19	−2.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30B···O2	0.96	2.36	2.864 (4)	112.3
C30—H30B···O29	0.96	2.64	3.322 (5)	128.5
C12—H12···O29	0.93	2.33	2.940 (4)	122.5
C26—H26C···O25	0.96	2.24	2.989 (5)	134.0
C1—H1B···O20ⁱ	0.97	2.52	3.430 (4)	156.7
C2'—H2'A···O29ⁱⁱ	0.97	2.63	3.252 (5)	122.2

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

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