1,2-Dihydro­cedrelone

Devi, S.S.; Rajan, S.S.; Kumar, R.M.; Narasimhan, S.

doi:10.1107/S1600536807042535

1,2-Dihydrocedrelone

S. S. Devi, S. S. Rajan, R. M. Kumar and S. Narasimhan

The title compound (systematic name: 7-furan-3-yl-6-hydroxy-4,4,8,10,13-pentamethyl-1,8,9,10,11,12,13,15,16,17-decahydro-2H,4H-20-oxacyclopropa[14,15]cyclopenta[a]phenanthrene-3,7-dione), C₂₆H₃₂O₅, is a semi-synthetic derivative of cedrelone, a natural compound isolated from Toona ciliata. The orientation of the furan ring and the ring conformations are the same as for cedrelone itself, with the exception of ring A. Rings A, B, C and D adopt sofa, half-chair, twist and envelope conformations, respectively. The crystal structure involves intramolecular O—H

O and intermolecular C—H

O and O—H

O hydrogen bonds. All the hydrogen bonds in the crystal structure contribute to the formation of a macrocyclic ring motif R₄⁴(28).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042535/wn2196sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042535/wn2196Isup2.hkl Contains datablock I

CCDC reference: 663693

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.062
wR factor = 0.189
Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.797
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.56
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.30
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H19A   ..  H30C    ..       1.80 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      48.00 A   3 

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           67.45
           From the CIF: _reflns_number_total               2161
           Count of symmetry unique reflns         2172
           Completeness (_total/calc)             99.49%
           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 C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          S
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
   8 ALERT level C = Check and explain
  11 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

A tetranortriterpenoid, cedrelone, has been previously isolated from Toona ciliata and its three dimensional structure was reported earlier (Zeumer et al., 2000). It possesses half the antifeedant activity of the most potent azadirachtin-A from Azadirachta indica. The title compound (Fig. 1), a semisynthetic derivative of cedrelone, differs from the parent molecule simply by having single bond C1—C2 rather than C1═C2. Except for ring A, the ring conformations in the title compound are the same as in cedrelone (Zeumer et al., 2000). The orientation of the furan ring is defined by the torsion angle C16—C17—C20—C22 = 179.8 (4)°; the corresponding value in cedrelone is 168.3 (4)°.

Ring A exists in a sofa conformation (Cremer & Pople, 1975) [Q_T = 0.688 (4) Å, φ₂ = -48 (3)°, q₂ = 0.677 (4) Å], and a mirror plane passes through atoms C3 and C10; in cedrelone itself, ring A adopts a distorted half-chair conformation. Ring B [Q_T =0.522 (4) Å, φ₂=32.3 (5)°,q₂ =0.435 (3) Å] adopts a half-chair conformation. Ring C adopts a twist conformation [Q_T =0.760 (3) Å, φ₂ =88.1 (3) °, q₂ =0.757 (3) Å]. The atoms C8 and C9 deviate from the mean plane of the other four atoms by 0.385 (3) Å and -0.407 (3) Å respectively. Ring D is in an envelope conformation [φ₂ = -145.1 (3)°,q₂ = 0.204 (4) Å] and ring E is planar (Nardelli, 1995). Ring pairs A/B, B/C and C/D are in quasi-trans fusion as evident from the endocyclic torsion angles of ring junction atoms. Thus, for rings A/B C4—C5—C10—C1 = -51.8 (4)° and C6—C5—C10—C9 = 9.8 (5)\5; for rings B/C C7—C8—C9—C10 = 63.5 (4)° and C14—C8—C9—C11 = -37.9 (4)°; for rings C/D C12—C13—C14—C8 = 58.5 (4)° and C17—C13—C14—C15 = -19.0 (4)°.

The packing of the molecules (Fig. 2) reveals that the crystal structure is stabilized by a network of hydrogen bonds (Table 1). The hydrogen bond C12—H12A···O15(-x+2,y+1/2,-z) forms an infinite chain, graph set motif C(9). A ring motif S(5) is formed by the hydrogen bond O6—H6···O7. In addition, R₂²(9) is generated through C2—H2A···O7(1+x,y,z) and O6—H6···O3(-1+x,y,z). All the observed hydrogen bonds in the crystal structure together form a macrocyclic ring motif R₄⁴(28).

Related literature top

Many cedrelone derivatives have been reported (Hodges et al., 1963). The three-dimensional structure of cedrelone itself has previously been reported (Zeumer et al., 2000). For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Narayanan et al. (1980).

Experimental top

Acetic acid (5 ml) was placed in a 25 ml Erylenmeyer flask fitted with microwave and reflux condenser with guard tube. To this cedrelone (141 mg, 0.33 mmol) and activated zinc was added. The mixture was then subjected to microwave radiation. After completion of the reaction, the solution was passed through a celite bed, followed by acetic acid and was removed by vacuum distillation. The title compound was purified by short flash (under nitrogen) column chromatography.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).

Figures top

	Fig. 1. Molecular structure of the title compound, with 30% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen atoms have been omitted.
	Fig. 2. A view of the packing in the crystal structure, showing the R₄⁴(28) ring. Dashed lines indicate hydrogen bonding. H atoms not involved in hydrogen bonding have been omitted.

7-furan-3-yl-6-hydroxy-4,4,8,10,13-pentamethyl-1,8,9,10,11,12,13,15,16,17- decahydro-2H,4H-20-oxacyclopropa[14,15]cyclopenta[a]phenanthrene- 3,7-dione top

Crystal data top

C₂₆H₃₂O₅	F(000) = 456
M_r = 424.52	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 8.302 (4) Å	Cell parameters from 25 reflections
b = 10.150 (2) Å	θ = 15–30°
c = 13.560 (5) Å	µ = 0.68 mm⁻¹
β = 95.330 (3)°	T = 293 K
V = 1137.7 (7) Å³	Rod, colourless
Z = 2	0.30 × 0.23 × 0.21 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.087
Radiation source: fine-focus sealed tube	θ_max = 67.5°, θ_min = 3.3°
Graphite monochromator	h = 0→9
non–profiled ω/2θ scans	k = 0→12
2591 measured reflections	l = −16→16
2161 independent reflections	3 standard reflections every 200 reflections
1974 reflections with I > 2σ(I)	intensity decay: 3%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.189	H-atom parameters constrained
S = 0.80	w = 1/[σ²(F_o²) + (0.199P)² + 0.4014P] where P = (F_o² + 2F_c²)/3
2161 reflections	(Δ/σ)_max < 0.001
286 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₆H₃₂O₅	V = 1137.7 (7) Å³
M_r = 424.52	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 8.302 (4) Å	µ = 0.68 mm⁻¹
b = 10.150 (2) Å	T = 293 K
c = 13.560 (5) Å	0.30 × 0.23 × 0.21 mm
β = 95.330 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.087
2591 measured reflections	3 standard reflections every 200 reflections
2161 independent reflections	intensity decay: 3%
1974 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.189	H-atom parameters constrained
S = 0.80	Δρ_max = 0.25 e Å⁻³
2161 reflections	Δρ_min = −0.34 e Å⁻³
286 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 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
O3	1.5868 (3)	0.4276 (5)	0.4887 (2)	0.0712 (11)
O6	0.9552 (3)	0.3939 (4)	0.4596 (2)	0.0630 (9)
H6	0.8586	0.3758	0.4535	0.095*
O7	0.7759 (3)	0.2519 (4)	0.3276 (2)	0.0597 (8)
O15	0.9023 (4)	−0.0169 (3)	0.1327 (2)	0.0562 (8)
O23	0.4733 (4)	0.2782 (4)	−0.2042 (3)	0.0756 (10)
C1	1.3541 (5)	0.4167 (4)	0.2475 (3)	0.0504 (9)
H1A	1.2753	0.4857	0.2312	0.060*
H1B	1.3997	0.3917	0.1868	0.060*
C2	1.4901 (5)	0.4715 (5)	0.3212 (3)	0.0552 (10)
H2A	1.5929	0.4370	0.3043	0.066*
H2B	1.4933	0.5666	0.3145	0.066*
C3	1.4699 (5)	0.4379 (5)	0.4265 (3)	0.0543 (10)
C4	1.2979 (4)	0.4246 (5)	0.4560 (3)	0.0538 (10)
C5	1.1889 (4)	0.3489 (4)	0.3773 (2)	0.0426 (8)
C6	1.0297 (4)	0.3354 (4)	0.3850 (3)	0.0471 (9)
C7	0.9206 (4)	0.2529 (4)	0.3168 (2)	0.0444 (8)
C8	0.9996 (4)	0.1674 (4)	0.2466 (3)	0.0414 (8)
C9	1.1337 (4)	0.2540 (4)	0.2070 (2)	0.0402 (8)
H9	1.0782	0.3363	0.1871	0.048*
C10	1.2675 (4)	0.2968 (4)	0.2875 (2)	0.0392 (7)
C11	1.1805 (4)	0.1959 (5)	0.1099 (2)	0.0467 (8)
H11A	1.2008	0.1022	0.1182	0.056*
H11B	1.2792	0.2372	0.0923	0.056*
C12	1.0432 (4)	0.2181 (5)	0.0258 (3)	0.0505 (9)
H12A	1.0549	0.3052	−0.0022	0.061*
H12B	1.0538	0.1540	−0.0262	0.061*
C13	0.8738 (4)	0.2059 (4)	0.0624 (3)	0.0444 (8)
C14	0.8874 (4)	0.1230 (4)	0.1566 (3)	0.0439 (8)
C15	0.7478 (5)	0.0347 (5)	0.1551 (3)	0.0548 (10)
H15	0.7027	0.0105	0.2169	0.066*
C16	0.6376 (5)	0.0597 (5)	0.0623 (3)	0.0610 (11)
H16A	0.5500	0.1187	0.0752	0.073*
H16B	0.5924	−0.0219	0.0348	0.073*
C17	0.7501 (4)	0.1237 (4)	−0.0076 (3)	0.0493 (9)
H17	0.8114	0.0522	−0.0351	0.059*
C18	0.7977 (5)	0.3403 (4)	0.0818 (3)	0.0520 (9)
H18A	0.7887	0.3912	0.0218	0.078*
H18B	0.8646	0.3864	0.1320	0.078*
H18C	0.6921	0.3274	0.1036	0.078*
C19	1.3932 (4)	0.1871 (4)	0.3153 (3)	0.0486 (9)
H19A	1.3399	0.1124	0.3410	0.073*
H19B	1.4739	0.2196	0.3646	0.073*
H19C	1.4438	0.1613	0.2574	0.073*
C20	0.6656 (5)	0.1966 (5)	−0.0939 (3)	0.0541 (9)
C21	0.5047 (5)	0.2089 (7)	−0.1179 (3)	0.0687 (13)
H21	0.4257	0.1748	−0.0808	0.082*
C22	0.7396 (6)	0.2648 (5)	−0.1704 (4)	0.0666 (12)
H22	0.8499	0.2757	−0.1747	0.080*
C23	0.6198 (7)	0.3102 (5)	−0.2348 (4)	0.0716 (14)
H23	0.6348	0.3569	−0.2923	0.086*
C28	1.2986 (5)	0.3573 (8)	0.5571 (3)	0.0775 (16)
H28A	1.3600	0.4095	0.6063	0.116*
H28B	1.3467	0.2716	0.5541	0.116*
H28C	1.1895	0.3487	0.5743	0.116*
C29	1.2402 (6)	0.5703 (6)	0.4622 (5)	0.0755 (15)
H29A	1.2370	0.6102	0.3979	0.113*
H29B	1.3140	0.6181	0.5077	0.113*
H29C	1.1341	0.5723	0.4849	0.113*
C30	1.0586 (5)	0.0445 (4)	0.3070 (3)	0.0511 (9)
H30A	1.1104	−0.0153	0.2651	0.077*
H30B	0.9678	0.0016	0.3322	0.077*
H30C	1.1342	0.0709	0.3613	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0370 (14)	0.101 (3)	0.0708 (18)	0.0006 (17)	−0.0225 (13)	−0.0111 (19)
O6	0.0343 (13)	0.091 (2)	0.0628 (16)	−0.0005 (15)	−0.0003 (11)	−0.0290 (16)
O7	0.0232 (12)	0.082 (2)	0.0742 (17)	−0.0001 (14)	0.0049 (10)	−0.0155 (16)
O15	0.0564 (17)	0.0424 (14)	0.0668 (17)	−0.0008 (13)	−0.0096 (13)	−0.0048 (12)
O23	0.0601 (19)	0.075 (2)	0.085 (2)	0.0165 (18)	−0.0323 (16)	−0.0062 (19)
C1	0.0315 (17)	0.058 (2)	0.060 (2)	−0.0098 (17)	−0.0086 (15)	0.0033 (18)
C2	0.0330 (18)	0.058 (2)	0.071 (2)	−0.0062 (18)	−0.0121 (15)	−0.002 (2)
C3	0.0367 (19)	0.062 (2)	0.061 (2)	−0.0051 (18)	−0.0128 (15)	−0.0082 (19)
C4	0.0306 (18)	0.072 (3)	0.055 (2)	0.0025 (19)	−0.0158 (14)	−0.0133 (19)
C5	0.0311 (16)	0.0515 (19)	0.0429 (16)	0.0036 (16)	−0.0091 (12)	−0.0012 (15)
C6	0.0336 (16)	0.061 (2)	0.0448 (16)	−0.0009 (17)	−0.0049 (12)	−0.0070 (16)
C7	0.0284 (16)	0.056 (2)	0.0479 (17)	0.0004 (16)	−0.0008 (12)	0.0012 (16)
C8	0.0255 (14)	0.0461 (19)	0.0511 (17)	−0.0025 (15)	−0.0043 (12)	−0.0021 (15)
C9	0.0243 (15)	0.0468 (18)	0.0481 (16)	−0.0006 (15)	−0.0044 (12)	0.0013 (15)
C10	0.0260 (14)	0.0438 (17)	0.0461 (16)	0.0030 (14)	−0.0062 (12)	0.0007 (14)
C11	0.0301 (15)	0.061 (2)	0.0483 (17)	−0.0009 (17)	−0.0027 (13)	−0.0041 (17)
C12	0.0378 (18)	0.064 (2)	0.0475 (18)	−0.0063 (18)	−0.0073 (13)	0.0010 (17)
C13	0.0336 (17)	0.0467 (18)	0.0504 (17)	−0.0047 (15)	−0.0093 (13)	−0.0034 (16)
C14	0.0288 (16)	0.0430 (19)	0.058 (2)	−0.0015 (15)	−0.0051 (13)	−0.0040 (16)
C15	0.0432 (19)	0.059 (2)	0.060 (2)	−0.021 (2)	−0.0044 (15)	−0.0022 (19)
C16	0.046 (2)	0.065 (3)	0.069 (2)	−0.014 (2)	−0.0117 (17)	−0.009 (2)
C17	0.0391 (19)	0.051 (2)	0.0547 (19)	−0.0077 (17)	−0.0134 (14)	−0.0054 (17)
C18	0.0413 (19)	0.0432 (19)	0.067 (2)	−0.0006 (17)	−0.0164 (15)	−0.0061 (18)
C19	0.0234 (15)	0.056 (2)	0.064 (2)	0.0078 (16)	−0.0068 (13)	0.0006 (18)
C20	0.0399 (19)	0.053 (2)	0.065 (2)	0.0002 (18)	−0.0192 (16)	−0.0077 (19)
C21	0.042 (2)	0.091 (4)	0.069 (2)	0.010 (2)	−0.0145 (17)	−0.009 (3)
C22	0.056 (2)	0.062 (3)	0.076 (3)	−0.009 (2)	−0.025 (2)	0.013 (2)
C23	0.074 (3)	0.054 (2)	0.079 (3)	−0.007 (2)	−0.035 (2)	0.012 (2)
C28	0.047 (2)	0.126 (5)	0.056 (2)	0.001 (3)	−0.0131 (17)	−0.003 (3)
C29	0.049 (2)	0.075 (3)	0.099 (3)	−0.002 (2)	−0.008 (2)	−0.036 (3)
C30	0.0405 (18)	0.050 (2)	0.061 (2)	−0.0072 (18)	−0.0040 (15)	0.0051 (18)

Geometric parameters (Å, º) top

O3—C3	1.230 (5)	C12—H12A	0.9700
O6—C6	1.369 (5)	C12—H12B	0.9700
O6—H6	0.8200	C13—C14	1.525 (5)
O7—C7	1.223 (4)	C13—C18	1.537 (6)
O15—C15	1.444 (6)	C13—C17	1.572 (5)
O15—C14	1.465 (5)	C14—C15	1.464 (5)
O23—C23	1.360 (7)	C15—C16	1.507 (6)
O23—C21	1.370 (6)	C15—H15	0.9800
C1—C10	1.538 (5)	C16—C17	1.535 (6)
C1—C2	1.541 (5)	C16—H16A	0.9700
C1—H1A	0.9700	C16—H16B	0.9700
C1—H1B	0.9700	C17—C20	1.502 (5)
C2—C3	1.491 (6)	C17—H17	0.9800
C2—H2A	0.9700	C18—H18A	0.9600
C2—H2B	0.9700	C18—H18B	0.9600
C3—C4	1.524 (6)	C18—H18C	0.9600
C4—C28	1.531 (7)	C19—H19A	0.9600
C4—C5	1.538 (5)	C19—H19B	0.9600
C4—C29	1.559 (8)	C19—H19C	0.9600
C5—C6	1.343 (5)	C20—C21	1.351 (6)
C5—C10	1.529 (5)	C20—C22	1.433 (7)
C6—C7	1.491 (5)	C21—H21	0.9300
C7—O7	1.223 (4)	C22—C23	1.342 (6)
C7—C8	1.486 (5)	C22—H22	0.9300
C8—C14	1.532 (5)	C23—H23	0.9300
C8—C30	1.548 (5)	C28—H28A	0.9600
C8—C9	1.553 (5)	C28—H28B	0.9600
C9—C11	1.525 (5)	C28—H28C	0.9600
C9—C10	1.546 (4)	C29—H29A	0.9600
C9—H9	0.9800	C29—H29B	0.9600
C10—C19	1.548 (5)	C29—H29C	0.9600
C11—C12	1.552 (5)	C30—H30A	0.9600
C11—H11A	0.9700	C30—H30B	0.9600
C11—H11B	0.9700	C30—H30C	0.9600
C12—C13	1.539 (5)

C6—O6—H6	109.5	C12—C13—C17	114.4 (3)
C15—O15—C14	60.4 (3)	C15—C14—O15	59.1 (3)
C23—O23—C21	106.2 (3)	C15—C14—C13	109.2 (3)
C10—C1—C2	113.3 (3)	O15—C14—C13	110.5 (3)
C10—C1—H1A	108.9	C15—C14—C8	127.9 (3)
C2—C1—H1A	108.9	O15—C14—C8	113.8 (3)
C10—C1—H1B	108.9	C13—C14—C8	119.8 (3)
C2—C1—H1B	108.9	O15—C15—C14	60.5 (2)
H1A—C1—H1B	107.7	O15—C15—C16	111.6 (3)
C3—C2—C1	113.4 (3)	C14—C15—C16	109.1 (4)
C3—C2—H2A	108.9	O15—C15—H15	120.4
C1—C2—H2A	108.9	C14—C15—H15	120.4
C3—C2—H2B	108.9	C16—C15—H15	120.4
C1—C2—H2B	108.9	C15—C16—C17	103.3 (3)
H2A—C2—H2B	107.7	C15—C16—H16A	111.1
O3—C3—C2	121.6 (4)	C17—C16—H16A	111.1
O3—C3—C4	120.7 (4)	C15—C16—H16B	111.1
C2—C3—C4	117.6 (3)	C17—C16—H16B	111.1
C3—C4—C28	110.4 (3)	H16A—C16—H16B	109.1
C3—C4—C5	111.5 (3)	C20—C17—C16	115.0 (3)
C28—C4—C5	110.5 (4)	C20—C17—C13	116.2 (3)
C3—C4—C29	103.3 (4)	C16—C17—C13	104.6 (3)
C28—C4—C29	110.5 (5)	C20—C17—H17	106.8
C5—C4—C29	110.3 (3)	C16—C17—H17	106.8
C6—C5—C10	121.5 (3)	C13—C17—H17	106.8
C6—C5—C4	121.1 (3)	C13—C18—H18A	109.5
C10—C5—C4	117.3 (3)	C13—C18—H18B	109.5
C5—C6—O6	121.9 (3)	H18A—C18—H18B	109.5
C5—C6—C7	123.7 (3)	C13—C18—H18C	109.5
O6—C6—C7	114.3 (3)	H18A—C18—H18C	109.5
O7—C7—C8	124.6 (3)	H18B—C18—H18C	109.5
O7—C7—C6	118.5 (3)	C10—C19—H19A	109.5
C8—C7—C6	116.6 (3)	C10—C19—H19B	109.5
C7—C8—C14	114.2 (3)	H19A—C19—H19B	109.5
C7—C8—C30	105.5 (3)	C10—C19—H19C	109.5
C14—C8—C30	108.9 (3)	H19A—C19—H19C	109.5
C7—C8—C9	105.3 (3)	H19B—C19—H19C	109.5
C14—C8—C9	107.1 (3)	C21—C20—C22	105.1 (4)
C30—C8—C9	115.9 (3)	C21—C20—C17	127.8 (4)
C11—C9—C10	119.6 (3)	C22—C20—C17	127.0 (4)
C11—C9—C8	109.1 (3)	C20—C21—O23	111.0 (5)
C10—C9—C8	114.0 (3)	C20—C21—H21	124.5
C11—C9—H9	104.1	O23—C21—H21	124.5
C10—C9—H9	104.1	C23—C22—C20	107.2 (4)
C8—C9—H9	104.1	C23—C22—H22	126.4
C5—C10—C1	104.8 (3)	C20—C22—H22	126.4
C5—C10—C9	109.1 (2)	C22—C23—O23	110.4 (5)
C1—C10—C9	107.6 (3)	C22—C23—H23	124.8
C5—C10—C19	112.5 (3)	O23—C23—H23	124.8
C1—C10—C19	109.2 (3)	C4—C28—H28A	109.5
C9—C10—C19	113.2 (3)	C4—C28—H28B	109.5
C9—C11—C12	110.5 (3)	H28A—C28—H28B	109.5
C9—C11—H11A	109.6	C4—C28—H28C	109.5
C12—C11—H11A	109.6	H28A—C28—H28C	109.5
C9—C11—H11B	109.6	H28B—C28—H28C	109.5
C12—C11—H11B	109.6	C4—C29—H29A	109.5
H11A—C11—H11B	108.1	C4—C29—H29B	109.5
C13—C12—C11	112.4 (3)	H29A—C29—H29B	109.5
C13—C12—H12A	109.1	C4—C29—H29C	109.5
C11—C12—H12A	109.1	H29A—C29—H29C	109.5
C13—C12—H12B	109.1	H29B—C29—H29C	109.5
C11—C12—H12B	109.1	C8—C30—H30A	109.5
H12A—C12—H12B	107.8	C8—C30—H30B	109.5
C14—C13—C18	110.3 (3)	H30A—C30—H30B	109.5
C14—C13—C12	108.4 (3)	C8—C30—H30C	109.5
C18—C13—C12	112.7 (3)	H30A—C30—H30C	109.5
C14—C13—C17	101.9 (3)	H30B—C30—H30C	109.5
C18—C13—C17	108.6 (3)

C10—C1—C2—C3	−23.4 (5)	C9—C11—C12—C13	−36.7 (5)
C1—C2—C3—O3	152.0 (5)	C11—C12—C13—C14	−22.8 (5)
C1—C2—C3—C4	−31.6 (6)	C11—C12—C13—C18	99.6 (4)
O3—C3—C4—C28	−17.6 (7)	C11—C12—C13—C17	−135.7 (4)
C2—C3—C4—C28	165.9 (5)	C15—O15—C14—C13	−100.7 (3)
O3—C3—C4—C5	−141.0 (5)	C15—O15—C14—C8	121.2 (4)
C2—C3—C4—C5	42.5 (6)	C18—C13—C14—C15	96.1 (4)
O3—C3—C4—C29	100.5 (5)	C12—C13—C14—C15	−140.0 (3)
C2—C3—C4—C29	−76.0 (5)	C17—C13—C14—C15	−19.0 (4)
C3—C4—C5—C6	−174.6 (4)	C18—C13—C14—O15	159.3 (3)
C28—C4—C5—C6	62.1 (5)	C12—C13—C14—O15	−76.8 (4)
C29—C4—C5—C6	−60.4 (6)	C17—C13—C14—O15	44.2 (4)
C3—C4—C5—C10	2.0 (5)	C18—C13—C14—C8	−65.3 (4)
C28—C4—C5—C10	−121.3 (4)	C12—C13—C14—C8	58.5 (4)
C29—C4—C5—C10	116.2 (4)	C17—C13—C14—C8	179.5 (3)
C10—C5—C6—O6	−172.9 (4)	C7—C8—C14—C15	−67.0 (5)
C4—C5—C6—O6	3.6 (6)	C30—C8—C14—C15	50.7 (5)
C10—C5—C6—C7	9.5 (6)	C9—C8—C14—C15	176.8 (4)
C4—C5—C6—C7	−174.0 (4)	C7—C8—C14—O15	−135.4 (4)
C5—C6—C7—O7	−176.8 (4)	C30—C8—C14—O15	−17.7 (4)
O6—C6—C7—O7	5.5 (6)	C9—C8—C14—O15	108.4 (4)
C5—C6—C7—C8	9.0 (6)	C7—C8—C14—C13	90.6 (4)
O6—C6—C7—C8	−168.8 (4)	C30—C8—C14—C13	−151.7 (3)
O7—C7—C8—C14	26.4 (5)	C9—C8—C14—C13	−25.6 (4)
C6—C7—C8—C14	−159.7 (3)	C14—O15—C15—C16	100.4 (4)
O7—C7—C8—C30	−93.2 (4)	C13—C14—C15—O15	103.0 (3)
C6—C7—C8—C30	80.7 (4)	C8—C14—C15—O15	−97.5 (4)
O7—C7—C8—C9	143.6 (4)	O15—C14—C15—C16	−104.6 (4)
C6—C7—C8—C9	−42.5 (4)	C13—C14—C15—C16	−1.6 (5)
C7—C8—C9—C11	−159.9 (3)	C8—C14—C15—C16	157.9 (4)
C14—C8—C9—C11	−37.9 (4)	O15—C15—C16—C17	−42.8 (5)
C30—C8—C9—C11	83.8 (4)	C14—C15—C16—C17	22.2 (5)
C7—C8—C9—C10	63.5 (4)	C15—C16—C17—C20	−162.2 (4)
C14—C8—C9—C10	−174.6 (3)	C15—C16—C17—C13	−33.5 (5)
C30—C8—C9—C10	−52.8 (4)	C14—C13—C17—C20	160.1 (3)
C6—C5—C10—C1	124.8 (4)	C18—C13—C17—C20	43.8 (4)
C4—C5—C10—C1	−51.8 (4)	C12—C13—C17—C20	−83.1 (5)
C6—C5—C10—C9	9.8 (5)	C14—C13—C17—C16	32.2 (4)
C4—C5—C10—C9	−166.8 (3)	C18—C13—C17—C16	−84.1 (4)
C6—C5—C10—C19	−116.7 (4)	C12—C13—C17—C16	149.0 (4)
C4—C5—C10—C19	66.7 (4)	C16—C17—C20—C21	−1.9 (7)
C2—C1—C10—C5	63.1 (4)	C13—C17—C20—C21	−124.5 (5)
C2—C1—C10—C9	179.2 (3)	C16—C17—C20—C22	−179.8 (4)
C2—C1—C10—C19	−57.6 (4)	C13—C17—C20—C22	57.6 (6)
C11—C9—C10—C5	−179.0 (3)	C22—C20—C21—O23	0.8 (6)
C8—C9—C10—C5	−47.3 (4)	C17—C20—C21—O23	−177.5 (4)
C11—C9—C10—C1	67.8 (4)	C23—O23—C21—C20	−0.1 (6)
C8—C9—C10—C1	−160.4 (3)	C21—C20—C22—C23	−1.2 (6)
C11—C9—C10—C19	−52.8 (4)	C17—C20—C22—C23	177.1 (4)
C8—C9—C10—C19	78.9 (4)	C20—C22—C23—O23	1.2 (6)
C10—C9—C11—C12	−154.6 (3)	C21—O23—C23—C22	−0.7 (6)
C8—C9—C11—C12	71.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O3ⁱ	0.82	2.41	3.139 (4)	149
C12—H12A···O15ⁱⁱ	0.97	2.58	3.499 (5)	159
C2—H2A···O7ⁱⁱⁱ	0.97	2.42	3.251 (6)	144
O6—H6···O7	0.82	2.18	2.646 (4)	116

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

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂O₅
M_r	424.52
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	8.302 (4), 10.150 (2), 13.560 (5)
β (°)	95.330 (3)
V (Å³)	1137.7 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.30 × 0.23 × 0.21

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2591, 2161, 1974
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.189, 0.80
No. of reflections	2161
No. of parameters	286
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.34

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and PARST97 (Nardelli, 1995).