A novel diterpene lactone

Doriguetto, A.C.; Vieira, H.S.; Ellena, J.A.; Takahashi, J.A.; Boaventura, M.A.D.; Mascarenhas, Y.P.

doi:10.1107/S160053680202086X

A novel diterpene lactone

A. C. Doriguetto, H. S. Vieira, J. A. Ellena, J. A. Takahashi, M. A. D. Boaventura and Y. P. Mascarenhas

A highly rearranged novel dilactone, ent-5α,15α-epoxy-9,10-friedo-10β,11β-dihydroxy-16,11α:19,10β-diseco-17-norkauran-16,19-dioic acid 16 $\rightarrow$ 11:19 $\rightarrow$ 10-dilactone, C₁₉H₂₄O₅, was synthesized from ent-kaur-9(11)-en,16-nor,19-oic acid, which was obtained by oxidation of grandiflorenic acid, under Baeyer–Villiger rearrangement conditions. The structure of the final product was determined unambiguously by X-ray analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202086X/ac6020sup1.cif Contains datablocks global, 3
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680202086X/ac60203sup2.hkl Contains datablock 3

CCDC reference: 176188

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.122
Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.48
         From the CIF: _reflns_number_total               2074
         Count of symmetry unique reflns         2082
         Completeness (_total/calc)             99.62%
         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
          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.

Comment top

Natural and synthetic diterpene lactones show many important biological activities: anti-HIV (Chen et al., 1992), antitumor (Ghisalberti, 1997) and allelopathic (e.g. the phytohormones gibberellins), among others. In an attempt to synthesize novel diterpene lactones from natural sources, for biological screening, the norketone (2), obtained from grandiflorenic acid (1), isolated from Wedelia paludosa (Asteraceae), was submitted to a Baeyer–Villiger oxidation (Anastasia et al., 1985). The product was the very rearranged dilactone (3), whose structure was unambiguously confirmed by X-ray analysis.

Fig. 1 shows an ORTEP-3 (Farrugia, 1997) view of (3). X-ray crystallographic analysis showed that a rearrangement involving C20 occurred, leading to the formation of a lactone in ring A. This rearrangement is common in natural diterpenoids, such as tetrachirin (Zabel et al., 1980; Vieira et al., 2001) and eupatalbin (Herz et al., 1979). Two other changes on the skeleton of (1) occurred: ring D rearrangement leading to the formation of a second lactone moiety, as well as an ether linkage on ring B between C5 and C15 in (3).

The main bond lengths and angles are given in Table 1. The mean value of the C—C single bond distances is 1.54 (2) Å, in good agreement with the expected value for formal single bonds (Orpen et al., 1992). The C—O single-bond lengths are very similar [mean 1.46 (2) Å], except for O2—C19 and O4—C16 ones, whose bond lengths are 1.364 (2) and 1.367 (2) Å, respectively. This decrease in bond length is a consequence of resonance involving the trio O═C—O localized in the two lactones rings. The O1═C19 and O3═C16 bond lengths of the two carbonyl are 1.202 (3) and 1.205 (3) Å, respectively. The three C—O—C angles are also similar [mean 109 (1)°]. The two lactone rings are in envelope conformations, with atoms C5 and C12 in the flap positions (Cremer & Pople, 1975). No intra- or intermolecular hydrogen bonds occur in the structure of (3).

Experimental top

Grandiflorenic acid, (1), was reacted with NaIO₄ and catalytic amounts of OsO₄ (Castellaro et al., 1990). The product was norketone (2). Under Baeyer–Villiger rearrangement conditions, 2.5 ml of hydrogen peroxide (30%) dissolved in anhydrous dichloromethane (15 ml) and 14 ml of anhydrous t rifluoroacetic acid were added to a solution of 0.66 mmol (200 mg) of ketoacid (2) in anhydrous dicloromethane (10 ml). The reaction was left at room temperature for 1 h. The unexpected novel compound (3) was isolated with 19% yield after column chromatography (hexane–ethyl acetate, 7:3). Colourless well shaped single crystals were obtained by recrystallization from chloroform.

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. ORTEP-3 (Farrugia, 1997) view of the title compound, showing the atom and ring labeling, and 50% probability ellipsoids.

ent-5α,15α-epoxy-9,10-friedo-10β,11β-dihydroxy-16,11α:19,10β-disecco-17- norkauran-16,19-dioic acid 16→11:19→10-dilactone top

Crystal data top

C₁₉H₂₄O₅	D_x = 1.407 Mg m⁻³
M_r = 332.38	Melting point: 503-505 K K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2081 reflections
a = 6.6980 (2) Å	θ = 1.0–27.5°
b = 13.6063 (3) Å	µ = 0.10 mm⁻¹
c = 17.2155 (5) Å	T = 120 K
V = 1568.85 (7) Å³	Prism, colorless
Z = 4	0.25 × 0.05 × 0.05 mm
F(000) = 712

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.023
CCD scans	θ_max = 27.5°, θ_min = 3.0°
3592 measured reflections	h = 0→8
2074 independent reflections	k = 0→17
1857 reflections with I > 2σ(I)	l = −22→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0794P)² + 0.0434P] where P = (F_o² + 2F_c²)/3
2074 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₉H₂₄O₅	V = 1568.85 (7) Å³
M_r = 332.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6980 (2) Å	µ = 0.10 mm⁻¹
b = 13.6063 (3) Å	T = 120 K
c = 17.2155 (5) Å	0.25 × 0.05 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	1857 reflections with I > 2σ(I)
3592 measured reflections	R_int = 0.023
2074 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.19	Δρ_max = 0.43 e Å⁻³
2074 reflections	Δρ_min = −0.52 e Å⁻³
219 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.9371 (3)	0.49131 (13)	0.42067 (9)	0.0297 (4)
O2	0.8328 (3)	0.60085 (11)	0.50859 (9)	0.0214 (4)
O3	0.2973 (3)	0.74070 (13)	0.78964 (10)	0.0304 (4)
O4	0.4551 (3)	0.75071 (11)	0.67530 (9)	0.0228 (4)
O5	0.5882 (3)	0.46932 (11)	0.66243 (9)	0.0218 (4)
C1	0.4906 (4)	0.61206 (16)	0.55131 (13)	0.0214 (5)
H1A	0.399	0.6005	0.5955	0.026*
H1B	0.4717	0.6807	0.5336	0.026*
C2	0.4365 (4)	0.54187 (17)	0.48498 (13)	0.0257 (5)
H2A	0.2899	0.5415	0.4779	0.031*
H2B	0.4976	0.5659	0.4362	0.031*
C3	0.5084 (4)	0.43717 (17)	0.50089 (13)	0.0243 (5)
H3A	0.4984	0.3979	0.4526	0.029*
H3B	0.4212	0.4064	0.5404	0.029*
C4	0.7271 (4)	0.43615 (16)	0.53009 (12)	0.0218 (5)
C5	0.7401 (4)	0.49211 (15)	0.60803 (12)	0.0195 (4)
C6	0.9420 (4)	0.47644 (17)	0.64873 (13)	0.0235 (5)
H6A	1.0522	0.4956	0.6136	0.028*
H6B	0.9587	0.4062	0.6623	0.028*
C7	0.9478 (4)	0.53995 (16)	0.72317 (13)	0.0228 (5)
H7A	0.9384	0.4974	0.7697	0.027*
H7B	1.075	0.5769	0.7257	0.027*
C8	0.7707 (4)	0.61175 (14)	0.72096 (12)	0.0192 (4)
C9	0.7818 (4)	0.67206 (15)	0.64208 (12)	0.0182 (4)
C10	0.7072 (3)	0.59853 (15)	0.57885 (12)	0.0179 (4)
C11	0.6601 (4)	0.76832 (15)	0.64905 (13)	0.0208 (5)
H11	0.66	0.8044	0.5984	0.025*
C12	0.7404 (4)	0.83416 (15)	0.71387 (13)	0.0239 (5)
H12A	0.6855	0.9016	0.711	0.029*
H12B	0.8881	0.8368	0.7141	0.029*
C13	0.6578 (4)	0.77688 (16)	0.78329 (14)	0.0231 (5)
H13	0.6573	0.817	0.8319	0.028*
C14	0.7739 (4)	0.67928 (15)	0.79330 (12)	0.0223 (5)
H14A	0.9145	0.6948	0.8062	0.027*
H14B	0.7165	0.6429	0.8378	0.027*
C15	0.5856 (4)	0.54330 (16)	0.72380 (13)	0.0217 (5)
H15A	0.5812	0.51	0.7749	0.026*
H15B	0.4632	0.5835	0.7187	0.026*
C16	0.4497 (4)	0.75566 (17)	0.75449 (13)	0.0236 (5)
C18	0.8139 (5)	0.33231 (17)	0.52817 (13)	0.0292 (6)
H18A	0.7925	0.3035	0.4767	0.044*
H18B	0.7477	0.2917	0.5675	0.044*
H18C	0.9574	0.3351	0.5391	0.044*
C19	0.8444 (4)	0.50782 (17)	0.47945 (12)	0.0225 (5)
C20	0.9974 (4)	0.70440 (17)	0.62387 (13)	0.0229 (5)
H20A	0.9951	0.7585	0.5863	0.034*
H20B	1.0717	0.6489	0.602	0.034*
H20C	1.0626	0.7264	0.6718	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0297 (10)	0.0369 (9)	0.0224 (7)	−0.0032 (8)	0.0050 (8)	−0.0076 (7)
O2	0.0245 (9)	0.0232 (7)	0.0166 (7)	−0.0025 (7)	0.0026 (7)	−0.0003 (6)
O3	0.0219 (9)	0.0361 (9)	0.0333 (9)	−0.0029 (8)	0.0056 (8)	−0.0097 (8)
O4	0.0190 (8)	0.0240 (8)	0.0255 (8)	0.0012 (7)	−0.0008 (7)	−0.0037 (6)
O5	0.0276 (9)	0.0183 (7)	0.0195 (7)	−0.0052 (7)	0.0040 (7)	−0.0020 (6)
C1	0.0208 (12)	0.0221 (10)	0.0214 (10)	−0.0001 (9)	−0.0027 (9)	−0.0004 (8)
C2	0.0250 (12)	0.0267 (11)	0.0255 (10)	−0.0028 (10)	−0.0049 (10)	−0.0012 (9)
C3	0.0268 (12)	0.0239 (10)	0.0222 (10)	−0.0068 (9)	0.0005 (10)	−0.0028 (9)
C4	0.0257 (12)	0.0201 (9)	0.0196 (10)	−0.0008 (10)	0.0008 (10)	−0.0016 (8)
C5	0.0227 (11)	0.0181 (9)	0.0179 (9)	0.0003 (9)	0.0031 (9)	−0.0002 (8)
C6	0.0282 (13)	0.0212 (10)	0.0212 (10)	0.0047 (10)	−0.0026 (10)	−0.0006 (9)
C7	0.0257 (11)	0.0225 (10)	0.0201 (10)	0.0059 (9)	−0.0027 (10)	−0.0005 (9)
C8	0.0200 (11)	0.0195 (9)	0.0181 (9)	0.0005 (9)	−0.0004 (9)	−0.0002 (8)
C9	0.0188 (11)	0.0169 (9)	0.0188 (9)	0.0018 (9)	−0.0010 (9)	0.0021 (8)
C10	0.0188 (11)	0.0187 (9)	0.0161 (9)	−0.0008 (9)	0.0020 (8)	0.0023 (7)
C11	0.0205 (11)	0.0178 (9)	0.0242 (10)	−0.0010 (10)	0.0006 (9)	0.0003 (8)
C12	0.0233 (11)	0.0185 (9)	0.0297 (11)	−0.0001 (9)	−0.0002 (10)	−0.0033 (9)
C13	0.0220 (11)	0.0218 (10)	0.0255 (10)	−0.0017 (9)	−0.0011 (10)	−0.0053 (9)
C14	0.0236 (12)	0.0230 (9)	0.0202 (10)	−0.0001 (10)	−0.0024 (9)	−0.0019 (8)
C15	0.0264 (11)	0.0199 (9)	0.0188 (9)	−0.0024 (9)	0.0036 (10)	−0.0021 (8)
C16	0.0214 (12)	0.0229 (10)	0.0266 (11)	0.0004 (10)	0.0018 (10)	−0.0071 (9)
C18	0.0403 (15)	0.0232 (10)	0.0241 (10)	0.0023 (11)	0.0001 (11)	−0.0029 (9)
C19	0.0237 (11)	0.0241 (10)	0.0197 (9)	−0.0013 (10)	−0.0012 (9)	−0.0037 (8)
C20	0.0192 (11)	0.0243 (10)	0.0253 (10)	−0.0026 (9)	−0.0012 (10)	−0.0008 (9)

Geometric parameters (Å, º) top

O1—C19	1.208 (3)	C7—H7A	0.99
O2—C19	1.364 (3)	C7—H7B	0.99
O2—C10	1.474 (3)	C8—C14	1.548 (3)
O3—C16	1.204 (3)	C8—C15	1.551 (3)
O4—C16	1.365 (3)	C8—C9	1.588 (3)
O4—C11	1.466 (3)	C9—C20	1.542 (3)
O5—C5	1.417 (3)	C9—C11	1.547 (3)
O5—C15	1.459 (3)	C9—C10	1.561 (3)
C1—C2	1.532 (3)	C11—C12	1.529 (3)
C1—C10	1.538 (3)	C11—H11	1
C1—H1A	0.99	C12—C13	1.530 (3)
C1—H1B	0.99	C12—H12A	0.99
C2—C3	1.529 (3)	C12—H12B	0.99
C2—H2A	0.99	C13—C16	1.507 (3)
C2—H2B	0.99	C13—C14	1.549 (3)
C3—C4	1.548 (4)	C13—H13	1
C3—H3A	0.99	C14—H14A	0.99
C3—H3B	0.99	C14—H14B	0.99
C4—C19	1.526 (3)	C15—H15A	0.99
C4—C18	1.528 (3)	C15—H15B	0.99
C4—C5	1.545 (3)	C18—H18A	0.98
C5—C6	1.538 (3)	C18—H18B	0.98
C5—C10	1.548 (3)	C18—H18C	0.98
C6—C7	1.546 (3)	C20—H20A	0.98
C6—H6A	0.99	C20—H20B	0.98
C6—H6B	0.99	C20—H20C	0.98
C7—C8	1.537 (3)

C19—O2—C10	108.32 (16)	C10—C9—C8	104.49 (15)
C16—O4—C11	108.93 (18)	O2—C10—C1	106.45 (16)
C5—O5—C15	109.62 (16)	O2—C10—C5	101.84 (16)
C2—C1—C10	112.21 (19)	C1—C10—C5	110.25 (19)
C2—C1—H1A	109.2	O2—C10—C9	112.09 (18)
C10—C1—H1A	109.2	C1—C10—C9	116.12 (18)
C2—C1—H1B	109.2	C5—C10—C9	109.13 (16)
C10—C1—H1B	109.2	O4—C11—C12	101.57 (18)
H1A—C1—H1B	107.9	O4—C11—C9	112.28 (17)
C3—C2—C1	111.91 (19)	C12—C11—C9	111.5 (2)
C3—C2—H2A	109.2	O4—C11—H11	110.4
C1—C2—H2A	109.2	C12—C11—H11	110.4
C3—C2—H2B	109.2	C9—C11—H11	110.4
C1—C2—H2B	109.2	C11—C12—C13	98.29 (17)
H2A—C2—H2B	107.9	C11—C12—H12A	112.1
C2—C3—C4	111.37 (19)	C13—C12—H12A	112.1
C2—C3—H3A	109.4	C11—C12—H12B	112.1
C4—C3—H3A	109.4	C13—C12—H12B	112.1
C2—C3—H3B	109.4	H12A—C12—H12B	109.7
C4—C3—H3B	109.4	C16—C13—C12	100.1 (2)
H3A—C3—H3B	108	C16—C13—C14	109.68 (18)
C19—C4—C18	112.5 (2)	C12—C13—C14	110.0 (2)
C19—C4—C5	98.75 (17)	C16—C13—H13	112.2
C18—C4—C5	116.92 (18)	C12—C13—H13	112.2
C19—C4—C3	107.21 (18)	C14—C13—H13	112.2
C18—C4—C3	111.2 (2)	C8—C14—C13	114.37 (18)
C5—C4—C3	109.32 (19)	C8—C14—H14A	108.7
O5—C5—C6	107.46 (17)	C13—C14—H14A	108.7
O5—C5—C4	115.18 (19)	C8—C14—H14B	108.7
C6—C5—C4	112.14 (19)	C13—C14—H14B	108.7
O5—C5—C10	108.48 (18)	H14A—C14—H14B	107.6
C6—C5—C10	113.73 (19)	O5—C15—C8	112.46 (18)
C4—C5—C10	99.85 (16)	O5—C15—H15A	109.1
C5—C6—C7	108.81 (19)	C8—C15—H15A	109.1
C5—C6—H6A	109.9	O5—C15—H15B	109.1
C7—C6—H6A	109.9	C8—C15—H15B	109.1
C5—C6—H6B	109.9	H15A—C15—H15B	107.8
C7—C6—H6B	109.9	O3—C16—O4	121.0 (2)
H6A—C6—H6B	108.3	O3—C16—C13	130.6 (2)
C8—C7—C6	108.37 (18)	O4—C16—C13	108.3 (2)
C8—C7—H7A	110	C4—C18—H18A	109.5
C6—C7—H7A	110	C4—C18—H18B	109.5
C8—C7—H7B	110	H18A—C18—H18B	109.5
C6—C7—H7B	110	C4—C18—H18C	109.5
H7A—C7—H7B	108.4	H18A—C18—H18C	109.5
C7—C8—C14	110.29 (18)	H18B—C18—H18C	109.5
C7—C8—C15	103.55 (17)	O1—C19—O2	120.6 (2)
C14—C8—C15	110.00 (18)	O1—C19—C4	128.6 (2)
C7—C8—C9	108.28 (17)	O2—C19—C4	110.72 (18)
C14—C8—C9	112.37 (16)	C9—C20—H20A	109.5
C15—C8—C9	111.98 (18)	C9—C20—H20B	109.5
C20—C9—C11	105.52 (17)	H20A—C20—H20B	109.5
C20—C9—C10	109.93 (18)	C9—C20—H20C	109.5
C11—C9—C10	115.36 (18)	H20A—C20—H20C	109.5
C20—C9—C8	111.39 (18)	H20B—C20—H20C	109.5
C11—C9—C8	110.27 (17)

C10—C1—C2—C3	45.2 (3)	C6—C5—C10—C9	−42.1 (2)
C1—C2—C3—C4	−46.4 (3)	C4—C5—C10—C9	−161.67 (19)
C2—C3—C4—C19	−43.7 (2)	C20—C9—C10—O2	−16.4 (2)
C2—C3—C4—C18	−166.97 (19)	C11—C9—C10—O2	102.8 (2)
C2—C3—C4—C5	62.4 (2)	C8—C9—C10—O2	−135.99 (18)
C15—O5—C5—C6	68.8 (2)	C20—C9—C10—C1	−139.00 (18)
C15—O5—C5—C4	−165.43 (18)	C11—C9—C10—C1	−19.9 (3)
C15—O5—C5—C10	−54.5 (2)	C8—C9—C10—C1	101.4 (2)
C19—C4—C5—O5	156.8 (2)	C20—C9—C10—C5	95.7 (2)
C18—C4—C5—O5	−82.4 (3)	C11—C9—C10—C5	−145.2 (2)
C3—C4—C5—O5	45.0 (2)	C8—C9—C10—C5	−23.9 (2)
C19—C4—C5—C6	−79.9 (2)	C16—O4—C11—C12	−28.6 (2)
C18—C4—C5—C6	40.9 (3)	C16—O4—C11—C9	90.7 (2)
C3—C4—C5—C6	168.36 (18)	C20—C9—C11—O4	−173.35 (17)
C19—C4—C5—C10	40.9 (2)	C10—C9—C11—O4	65.1 (2)
C18—C4—C5—C10	161.7 (2)	C8—C9—C11—O4	−52.9 (2)
C3—C4—C5—C10	−70.9 (2)	C20—C9—C11—C12	−60.1 (2)
O5—C5—C6—C7	−56.1 (2)	C10—C9—C11—C12	178.37 (18)
C4—C5—C6—C7	176.38 (18)	C8—C9—C11—C12	60.3 (2)
C10—C5—C6—C7	64.0 (2)	O4—C11—C12—C13	44.5 (2)
C5—C6—C7—C8	−11.8 (2)	C9—C11—C12—C13	−75.3 (2)
C6—C7—C8—C14	−178.27 (18)	C11—C12—C13—C16	−43.8 (2)
C6—C7—C8—C15	64.1 (2)	C11—C12—C13—C14	71.6 (2)
C6—C7—C8—C9	−54.9 (2)	C7—C8—C14—C13	158.0 (2)
C7—C8—C9—C20	−42.6 (2)	C15—C8—C14—C13	−88.4 (2)
C14—C8—C9—C20	79.5 (2)	C9—C8—C14—C13	37.1 (3)
C15—C8—C9—C20	−156.15 (18)	C16—C13—C14—C8	51.8 (3)
C7—C8—C9—C11	−159.42 (19)	C12—C13—C14—C8	−57.3 (3)
C14—C8—C9—C11	−37.4 (3)	C5—O5—C15—C8	−11.1 (2)
C15—C8—C9—C11	87.0 (2)	C7—C8—C15—O5	−54.7 (2)
C7—C8—C9—C10	76.0 (2)	C14—C8—C15—O5	−172.58 (17)
C14—C8—C9—C10	−161.90 (19)	C9—C8—C15—O5	61.7 (2)
C15—C8—C9—C10	−37.5 (2)	C11—O4—C16—O3	−177.8 (2)
C19—O2—C10—C1	−87.6 (2)	C11—O4—C16—C13	−0.2 (2)
C19—O2—C10—C5	27.9 (2)	C12—C13—C16—O3	−153.9 (3)
C19—O2—C10—C9	144.41 (18)	C14—C13—C16—O3	90.5 (3)
C2—C1—C10—O2	50.0 (2)	C12—C13—C16—O4	28.8 (2)
C2—C1—C10—C5	−59.7 (2)	C14—C13—C16—O4	−86.8 (2)
C2—C1—C10—C9	175.56 (18)	C10—O2—C19—O1	178.7 (2)
O5—C5—C10—O2	−163.91 (17)	C10—O2—C19—C4	−0.8 (3)
C6—C5—C10—O2	76.6 (2)	C18—C4—C19—O1	30.1 (4)
C4—C5—C10—O2	−43.0 (2)	C5—C4—C19—O1	154.1 (3)
O5—C5—C10—C1	−51.2 (2)	C3—C4—C19—O1	−92.4 (3)
C6—C5—C10—C1	−170.71 (18)	C18—C4—C19—O2	−150.5 (2)
C4—C5—C10—C1	69.7 (2)	C5—C4—C19—O2	−26.5 (2)
O5—C5—C10—C9	77.4 (2)	C3—C4—C19—O2	87.0 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄O₅
M_r	332.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	6.6980 (2), 13.6063 (3), 17.2155 (5)
V (Å³)	1568.85 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.05 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3592, 2074, 1857
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.122, 1.19
No. of reflections	2074
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.52

Computer programs: COLLECT (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—C19	1.208 (3)	C4—C19	1.526 (3)
O2—C19	1.364 (3)	C4—C5	1.545 (3)
O2—C10	1.474 (3)	C5—C10	1.548 (3)
O3—C16	1.204 (3)	C8—C15	1.551 (3)
O4—C16	1.365 (3)	C11—C12	1.529 (3)
O4—C11	1.466 (3)	C12—C13	1.530 (3)
O5—C5	1.417 (3)	C13—C16	1.507 (3)
O5—C15	1.459 (3)

C19—O2—C10	108.32 (16)	O3—C16—O4	121.0 (2)
C16—O4—C11	108.93 (18)	O1—C19—O2	120.6 (2)
C5—O5—C15	109.62 (16)

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