Guidongnin A, a natural diterpenoid

Shi, H.

doi:10.1107/S1600536807060965

Guidongnin A, a natural diterpenoid

The title compound, C₂₀H₂₆O₆, isolated from Rabdosia var lophanthoides Hara, is built up from five fused rings. The cyclohexane ring A adopts a chair conformation, ring B exists in a screw-boat conformation and ring C adopts a boat conformation; the two five-membered rings D and E adopt envelope conformations. The isobenzofuran ring system couples orthogonally to the methanocyclohepta[c]pyran unit through a spiro C atom. The asymmetric unit consists of two unique molecules linked by hydrogen bonds to form a dimer. The dimers are further interconnected through O—H

O hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060965/sj2433sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060965/sj2433Isup2.hkl Contains datablock I

CCDC reference: 673075

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.011 Å
R factor = 0.078
wR factor = 0.237
Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C6A    -   C21A    ..      11.44 su
PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         11

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.53
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       5.37 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5A    -   C9A     ..       6.06 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6A    -   C18A    ..       6.12 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1A    -   C11A    ..       5.88 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4A    -   C10A    ..       5.20 su

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               3556
           Count of symmetry unique reflns         3556
           Completeness (_total/calc)            100.00%
           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 C4     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A    ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5A    ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A    ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9A    ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A   ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11A   ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15A   ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......       1896

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

  16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The diterpenoid Guidongnin A, C₂₀H₂₆O₆, has been previously isolated from Rabdosia rubescens Hara (Sun et al., 1988), its structure was established from the spectral and chemical evidence. Recently we isolated the compound from Rabdosia var lophanthoides Hara for the first time, and its structure is confirmed by an X-ray diffraction study.

Two unique molecules are present in the asymmetric unit, both molecule 1 (Fig.1) and molecule 2 (Fig.2) are built up from five fused rings, three six membered (A,B,C,A',B'and C') and two five membered rings (D,E,D' and E'). The conformations of the different rings extracted from the puckering parameters (Cremer & Pople, 1975) are given in Table 2. Ring A and A' adopt a chair conformation, ring B and B' exist in a screw-boat conformation and rings C and C' adopt a boat conformation. Rings D, D', E and E' adopt an envelope conformation. The isobenzofuran ring system couples orthogonally to the methanocyclohepta[c] pyran moiety through a spiro C atom.

This two molecules are linked by O4—H4···O3A and O4A—H4A···O3 hydrogen bonds to form a dimer. The dimers are further interconnected through O—H···O hydrogen bonds (Fig.3).

Related literature top

For information on ring puckering analysis, see: Cremer & Pople (1975). For previous isolation of the title compound, see: Sun et al. (1988).

Experimental top

2 kg of dried powder from the whole plant, Rabdosia var lophanthoides Hara, was soaked three times with 95% EtOH at room temperature. The ethanolic extracts were evaporated under reduced pressure and the residue was successively fractionated with petroleum ether, EtOAc and n-BuOH. The residue of the petroleum ether fraction was subjected to column chromatography over silica gel. The column was eluted with a petroleum ether-EtOAc mixture and the title compound isolated. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular view of molecule 1 with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres with arbitrary radii.
	Fig. 2. Molecular view of molecule 2 with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres with arbitrary radii.
	Fig. 3. Partial packing view of the title compound showing O—H···O hydrogen bonding interactions. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry operations are assigned as follows: for atoms labelled with primes ('), (-1/2 + x, 3/2 - y, -z), asterisks (*) (1 - x, -1/2 + y, 1/2 - z), hashes (#) (-x + 1, 1/2 + y, 1/2 - z) and dollar signs ($) (1/2 + x, 3/2 - y, -z), respectively.].

(3aR,4R,4'aS,5'R,7'S,7aR,9'R,9'aS)-5',9'-dihydroxy-7a-methyl-8'- methyleneperhydrospiro[isobenzofuran-4(1H),4'(3'H)- [1H-7,9a]methanocyclohepta[c]pyran]-1',3(3aH)-dione top

Crystal data top

C₂₀H₂₆O₆	F(000) = 1552
M_r = 362.41	D_x = 1.340 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2028 reflections
a = 12.2614 (15) Å	θ = 2.2–18.1°
b = 15.6668 (18) Å	µ = 0.10 mm⁻¹
c = 18.697 (2) Å	T = 298 K
V = 3591.7 (8) Å³	Prismatic, colorless
Z = 8	0.41 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3556 independent reflections
Radiation source: fine-focus sealed tube	1970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −13→14
T_min = 0.961, T_max = 0.973	k = −16→18
17440 measured reflections	l = −22→18

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.237	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1062P)² + 2.5318P] where P = (F_o² + 2F_c²)/3
3556 reflections	(Δ/σ)_max = 0.001
472 parameters	Δρ_max = 0.54 e Å⁻³
1896 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₂₀H₂₆O₆	V = 3591.7 (8) Å³
M_r = 362.41	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 12.2614 (15) Å	µ = 0.10 mm⁻¹
b = 15.6668 (18) Å	T = 298 K
c = 18.697 (2) Å	0.41 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3556 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1970 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.973	R_int = 0.084
17440 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	1896 restraints
wR(F²) = 0.237	H-atom parameters constrained
S = 1.10	Δρ_max = 0.54 e Å⁻³
3556 reflections	Δρ_min = −0.56 e Å⁻³
472 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
O1	0.3555 (6)	0.3465 (4)	−0.0342 (3)	0.0854 (18)
O1A	0.1460 (6)	0.4505 (4)	0.0174 (3)	0.0770 (16)
O2	0.2908 (4)	0.4019 (4)	0.1997 (3)	0.0642 (14)
O2A	0.2089 (4)	0.7286 (3)	0.0555 (3)	0.0599 (13)
O3	0.2473 (5)	0.5342 (4)	0.2199 (4)	0.089 (2)
O3A	0.2729 (4)	0.7432 (4)	0.1633 (3)	0.0644 (15)
O4	0.4497 (6)	0.6058 (3)	0.1203 (3)	0.0697 (16)
H4	0.4029	0.6414	0.1108	0.105*
O4A	0.0623 (5)	0.6303 (4)	0.2404 (3)	0.0615 (15)
H4A	0.1224	0.6081	0.2357	0.092*
O5	0.5642 (5)	0.3563 (4)	0.2942 (3)	0.0704 (16)
H5	0.6109	0.3235	0.3092	0.106*
O5A	−0.0730 (4)	0.8390 (3)	0.0395 (3)	0.0554 (14)
H5B	−0.1236	0.8706	0.0284	0.083*
O6	0.2848 (6)	0.2872 (5)	0.0616 (4)	0.105 (2)
O6A	0.2237 (5)	0.5683 (4)	−0.0221 (4)	0.0778 (18)
C1	0.3744 (7)	0.3381 (5)	0.1955 (5)	0.0627 (19)
H1A	0.3433	0.2858	0.1767	0.075*
H1B	0.4017	0.3263	0.2432	0.075*
C1A	0.1156 (6)	0.7223 (5)	0.0093 (4)	0.0555 (18)
H1C	0.1384	0.6989	−0.0364	0.067*
H1D	0.0868	0.7791	0.0007	0.067*
C3	0.3182 (7)	0.4818 (6)	0.2136 (4)	0.0581 (19)
C3A	0.1937 (7)	0.7400 (5)	0.1253 (5)	0.0496 (17)
C4	0.4375 (6)	0.5041 (5)	0.2221 (4)	0.0453 (16)
C4A	0.0797 (6)	0.7523 (5)	0.1533 (4)	0.0445 (15)
C5	0.4566 (7)	0.5961 (5)	0.1943 (4)	0.0566 (18)
H5A	0.4037	0.6343	0.2170	0.068*
C5A	0.0716 (7)	0.7189 (5)	0.2313 (4)	0.0545 (17)
H5C	0.1354	0.7390	0.2581	0.065*
C6	0.5690 (7)	0.6152 (5)	0.2241 (4)	0.0558 (18)
C6A	−0.0275 (7)	0.7649 (5)	0.2585 (4)	0.0578 (19)
C7	0.5801 (8)	0.5631 (5)	0.2931 (4)	0.0617 (19)
H7	0.5992	0.5991	0.3341	0.074*
C7A	−0.0466 (7)	0.8426 (5)	0.2124 (4)	0.0601 (19)
H7A	−0.0576	0.8938	0.2416	0.072*
C8	0.6638 (7)	0.4907 (5)	0.2817 (4)	0.0592 (19)
H8A	0.7243	0.5119	0.2534	0.071*
H8B	0.6923	0.4726	0.3277	0.071*
C8A	−0.1419 (6)	0.8280 (5)	0.1616 (4)	0.0501 (17)
H8C	−0.1726	0.8828	0.1482	0.060*
H8D	−0.1981	0.7959	0.1862	0.060*
C9	0.6122 (6)	0.4138 (5)	0.2436 (4)	0.0544 (18)
H9	0.6700	0.3832	0.2180	0.065*
C9A	−0.1089 (6)	0.7800 (5)	0.0939 (4)	0.0451 (16)
H9A	−0.1730	0.7494	0.0758	0.054*
C10	0.5252 (6)	0.4415 (4)	0.1887 (4)	0.0416 (15)
H10	0.5641	0.4747	0.1523	0.050*
C10A	−0.0175 (5)	0.7145 (4)	0.1078 (3)	0.0364 (14)
H10A	−0.0504	0.6702	0.1380	0.044*
C11	0.4689 (6)	0.3660 (5)	0.1479 (4)	0.0481 (16)
C11A	0.0259 (6)	0.6667 (4)	0.0400 (4)	0.0415 (14)
C12	0.5449 (7)	0.2881 (5)	0.1368 (5)	0.0625 (19)
H12A	0.5762	0.2723	0.1826	0.075*
H12B	0.5016	0.2403	0.1202	0.075*
C12A	−0.0584 (6)	0.6565 (5)	−0.0210 (4)	0.0505 (17)
H12C	−0.0933	0.7112	−0.0293	0.061*
H12D	−0.0203	0.6407	−0.0645	0.061*
C13	0.6370 (7)	0.3038 (6)	0.0839 (5)	0.068 (2)
H13A	0.6829	0.3500	0.1007	0.082*
H13B	0.6816	0.2529	0.0797	0.082*
C13A	−0.1465 (7)	0.5897 (5)	−0.0059 (4)	0.0597 (19)
H13C	−0.1879	0.6060	0.0362	0.072*
H13D	−0.1963	0.5863	−0.0461	0.072*
C14	0.5892 (7)	0.3265 (6)	0.0117 (5)	0.073 (2)
H14A	0.5464	0.2786	−0.0056	0.088*
H14B	0.6482	0.3358	−0.0219	0.088*
C14A	−0.0931 (7)	0.5037 (5)	0.0062 (5)	0.063 (2)
H14C	−0.0528	0.4877	−0.0364	0.076*
H14D	−0.1492	0.4611	0.0141	0.076*
C15	0.5169 (7)	0.4059 (5)	0.0133 (4)	0.0534 (18)
C15A	−0.0155 (6)	0.5047 (5)	0.0704 (4)	0.0508 (17)
C16	0.4396 (8)	0.4081 (6)	−0.0503 (4)	0.074 (2)
H16A	0.4085	0.4647	−0.0560	0.089*
H16B	0.4776	0.3928	−0.0939	0.089*
C16A	0.0601 (8)	0.4272 (5)	0.0665 (5)	0.070 (2)
H16C	0.0899	0.4143	0.1134	0.084*
H16D	0.0208	0.3776	0.0492	0.084*
C18	0.3476 (8)	0.3369 (7)	0.0369 (5)	0.072 (2)
C18A	0.1552 (8)	0.5350 (6)	0.0136 (5)	0.0597 (19)
C19	0.4297 (6)	0.3962 (5)	0.0736 (4)	0.0485 (16)
H19	0.3944	0.4518	0.0799	0.058*
C19A	0.0699 (6)	0.5773 (4)	0.0622 (4)	0.0431 (15)
H19A	0.1043	0.5845	0.1092	0.052*
C20	0.4656 (7)	0.5224 (5)	0.3016 (4)	0.0589 (18)
H20A	0.4142	0.5619	0.3231	0.071*
H20B	0.4683	0.4704	0.3297	0.071*
C20A	0.0601 (7)	0.8482 (5)	0.1686 (4)	0.0578 (18)
H20C	0.1190	0.8730	0.1963	0.069*
H20D	0.0502	0.8806	0.1248	0.069*
C21	0.6457 (8)	0.6594 (6)	0.1925 (6)	0.081 (3)
H21A	0.6335	0.6825	0.1474	0.098*
H21B	0.7123	0.6677	0.2152	0.098*
C21A	−0.0921 (8)	0.7372 (7)	0.3096 (5)	0.091 (3)
H21C	−0.0777	0.6854	0.3319	0.109*
H21D	−0.1521	0.7695	0.3234	0.109*
C22	0.5889 (7)	0.4864 (6)	0.0139 (5)	0.065 (2)
H22A	0.6405	0.4827	0.0524	0.098*
H22B	0.5439	0.5360	0.0204	0.098*
H22C	0.6273	0.4908	−0.0307	0.098*
C22A	−0.0819 (8)	0.5005 (5)	0.1404 (4)	0.066 (2)
H22D	−0.1183	0.4464	0.1434	0.099*
H22E	−0.1350	0.5455	0.1408	0.099*
H22F	−0.0337	0.5069	0.1805	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.076 (4)	0.102 (4)	0.077 (4)	−0.006 (4)	−0.011 (3)	−0.034 (3)
O1A	0.081 (4)	0.056 (3)	0.094 (4)	0.013 (3)	−0.034 (3)	0.002 (3)
O2	0.045 (3)	0.069 (3)	0.079 (3)	0.006 (3)	0.008 (3)	0.010 (3)
O2A	0.038 (3)	0.070 (3)	0.072 (3)	−0.011 (2)	−0.007 (3)	−0.002 (3)
O3	0.057 (4)	0.091 (4)	0.118 (5)	0.034 (4)	0.006 (4)	−0.002 (4)
O3A	0.033 (3)	0.067 (4)	0.094 (4)	−0.005 (3)	0.015 (3)	−0.004 (3)
O4	0.097 (4)	0.061 (3)	0.052 (3)	0.015 (3)	−0.010 (3)	0.012 (3)
O4A	0.059 (3)	0.073 (4)	0.053 (3)	0.020 (3)	−0.004 (3)	−0.010 (3)
O5	0.064 (3)	0.077 (4)	0.070 (3)	0.021 (3)	0.003 (3)	0.031 (3)
O5A	0.055 (3)	0.056 (3)	0.056 (3)	0.006 (3)	−0.006 (3)	−0.017 (3)
O6	0.092 (5)	0.104 (5)	0.119 (5)	−0.047 (4)	−0.003 (4)	−0.014 (4)
O6A	0.060 (4)	0.080 (4)	0.093 (4)	0.002 (3)	−0.037 (4)	0.000 (3)
C1	0.059 (4)	0.054 (4)	0.074 (4)	−0.005 (4)	0.010 (4)	0.009 (4)
C1A	0.049 (4)	0.061 (4)	0.057 (4)	0.005 (3)	−0.008 (3)	−0.008 (3)
C3	0.064 (4)	0.059 (4)	0.051 (4)	0.010 (4)	0.006 (4)	0.010 (3)
C3A	0.042 (4)	0.041 (4)	0.065 (4)	−0.004 (3)	0.005 (3)	−0.002 (3)
C4	0.042 (3)	0.047 (3)	0.047 (3)	0.005 (3)	0.006 (3)	0.001 (3)
C4A	0.038 (3)	0.050 (3)	0.045 (3)	0.004 (3)	0.007 (3)	0.004 (3)
C5	0.070 (4)	0.049 (4)	0.051 (4)	0.018 (3)	−0.005 (4)	−0.003 (3)
C5A	0.047 (3)	0.066 (4)	0.051 (4)	0.015 (3)	0.011 (3)	0.009 (3)
C6	0.067 (4)	0.044 (4)	0.057 (4)	0.009 (4)	−0.002 (4)	−0.009 (3)
C6A	0.056 (4)	0.075 (4)	0.042 (4)	0.012 (4)	0.014 (4)	0.011 (3)
C7	0.080 (4)	0.062 (4)	0.043 (4)	0.003 (4)	−0.004 (4)	−0.013 (3)
C7A	0.058 (4)	0.063 (4)	0.059 (4)	0.012 (4)	0.011 (4)	0.022 (3)
C8	0.050 (4)	0.073 (4)	0.055 (4)	0.008 (4)	−0.007 (4)	0.005 (4)
C8A	0.041 (4)	0.056 (4)	0.053 (4)	0.008 (3)	0.001 (3)	−0.006 (3)
C9	0.049 (4)	0.056 (4)	0.058 (4)	0.014 (3)	0.008 (3)	0.007 (3)
C9A	0.041 (3)	0.046 (4)	0.048 (3)	−0.002 (3)	0.001 (3)	−0.004 (3)
C10	0.040 (3)	0.041 (3)	0.044 (3)	0.010 (3)	0.003 (3)	0.008 (3)
C10A	0.029 (3)	0.041 (3)	0.039 (3)	−0.003 (3)	−0.001 (3)	−0.004 (3)
C11	0.042 (3)	0.042 (3)	0.060 (3)	0.006 (3)	0.010 (3)	0.000 (3)
C11A	0.034 (3)	0.045 (3)	0.045 (3)	−0.007 (3)	−0.003 (3)	−0.004 (3)
C12	0.066 (4)	0.045 (4)	0.076 (4)	0.008 (4)	0.004 (4)	−0.003 (3)
C12A	0.050 (4)	0.062 (4)	0.039 (3)	0.002 (3)	0.002 (3)	0.000 (3)
C13	0.057 (4)	0.066 (4)	0.082 (5)	0.023 (4)	0.009 (4)	−0.005 (4)
C13A	0.053 (4)	0.071 (4)	0.055 (4)	−0.004 (4)	0.008 (4)	0.008 (4)
C14	0.063 (4)	0.081 (5)	0.077 (4)	0.005 (4)	0.009 (4)	−0.021 (4)
C14A	0.063 (4)	0.058 (4)	0.068 (4)	−0.012 (4)	−0.008 (4)	0.009 (4)
C15	0.051 (4)	0.061 (4)	0.047 (4)	0.010 (3)	0.004 (3)	−0.010 (3)
C15A	0.052 (4)	0.043 (4)	0.057 (4)	0.004 (3)	−0.011 (3)	−0.001 (3)
C16	0.066 (5)	0.098 (5)	0.057 (4)	0.015 (5)	0.005 (4)	−0.016 (4)
C16A	0.072 (5)	0.050 (4)	0.089 (5)	0.001 (4)	−0.024 (4)	−0.004 (4)
C18	0.060 (4)	0.078 (4)	0.078 (4)	0.003 (4)	−0.002 (4)	−0.009 (4)
C18A	0.053 (4)	0.061 (4)	0.065 (4)	0.010 (4)	−0.006 (4)	−0.001 (4)
C19	0.043 (3)	0.047 (3)	0.055 (3)	−0.005 (3)	0.002 (3)	−0.008 (3)
C19A	0.037 (3)	0.051 (3)	0.041 (3)	0.000 (3)	−0.005 (3)	0.001 (3)
C20	0.069 (4)	0.061 (4)	0.046 (3)	0.027 (3)	0.009 (3)	0.002 (3)
C20A	0.052 (4)	0.053 (4)	0.069 (4)	−0.002 (3)	0.013 (3)	0.008 (3)
C21	0.088 (6)	0.069 (6)	0.087 (6)	−0.019 (5)	−0.007 (6)	−0.003 (5)
C21A	0.090 (6)	0.123 (7)	0.059 (5)	0.054 (6)	−0.012 (5)	−0.023 (5)
C22	0.059 (5)	0.075 (5)	0.061 (5)	−0.005 (4)	0.012 (4)	0.007 (4)
C22A	0.069 (5)	0.061 (5)	0.069 (5)	−0.004 (4)	−0.022 (4)	−0.009 (4)

Geometric parameters (Å, º) top

O1—C18	1.343 (11)	C9A—C10A	1.543 (9)
O1—C16	1.444 (11)	C9A—H9A	0.9800
O1A—C18A	1.330 (10)	C10—C11	1.568 (10)
O1A—C16A	1.445 (11)	C10—H10	0.9800
O2—C3	1.323 (10)	C10A—C11A	1.566 (9)
O2—C1	1.432 (10)	C10A—H10A	0.9800
O2A—C3A	1.330 (9)	C11—C19	1.544 (10)
O2A—C1A	1.438 (9)	C11—C12	1.549 (10)
O3—C3	1.201 (10)	C11A—C12A	1.548 (10)
O3A—C3A	1.204 (9)	C11A—C19A	1.556 (10)
O4—C5	1.394 (9)	C12—C13	1.522 (12)
O4—H4	0.8200	C12—H12A	0.9700
O4A—C5A	1.404 (9)	C12—H12B	0.9700
O4A—H4A	0.8200	C12A—C13A	1.530 (11)
O5—C9	1.433 (9)	C12A—H12C	0.9700
O5—H5	0.8200	C12A—H12D	0.9700
O5A—C9A	1.443 (8)	C13—C14	1.515 (12)
O5A—H5B	0.8200	C13—H13A	0.9700
O6—C18	1.188 (11)	C13—H13B	0.9700
O6A—C18A	1.192 (10)	C13A—C14A	1.515 (11)
C1—C11	1.526 (10)	C13A—H13C	0.9700
C1—H1A	0.9700	C13A—H13D	0.9700
C1—H1B	0.9700	C14—C15	1.528 (11)
C1A—C11A	1.516 (10)	C14—H14A	0.9700
C1A—H1C	0.9700	C14—H14B	0.9700
C1A—H1D	0.9700	C14A—C15A	1.532 (11)
C3—C4	1.512 (12)	C14A—H14C	0.9700
C3A—C4A	1.504 (10)	C14A—H14D	0.9700
C4—C5	1.551 (11)	C15—C16	1.521 (11)
C4—C20	1.553 (10)	C15—C22	1.539 (11)
C4—C10	1.584 (10)	C15—C19	1.561 (10)
C4A—C20A	1.548 (11)	C15A—C16A	1.529 (11)
C4A—C5A	1.554 (10)	C15A—C22A	1.542 (11)
C4A—C10A	1.579 (10)	C15A—C19A	1.554 (10)
C5—C6	1.516 (12)	C16—H16A	0.9700
C5—H5A	0.9800	C16—H16B	0.9700
C5A—C6A	1.501 (11)	C16A—H16C	0.9700
C5A—H5C	0.9800	C16A—H16D	0.9700
C6—C21	1.308 (12)	C18—C19	1.531 (12)
C6—C7	1.533 (11)	C18A—C19A	1.537 (11)
C6A—C21A	1.314 (12)	C19—H19	0.9800
C6A—C7A	1.510 (11)	C19A—H19A	0.9800
C7—C8	1.544 (11)	C20—H20A	0.9700
C7—C20	1.550 (12)	C20—H20B	0.9700
C7—H7	0.9800	C20A—H20C	0.9700
C7A—C8A	1.523 (11)	C20A—H20D	0.9700
C7A—C20A	1.546 (11)	C21—H21A	0.9300
C7A—H7A	0.9800	C21—H21B	0.9300
C8—C9	1.536 (11)	C21A—H21C	0.9300
C8—H8A	0.9700	C21A—H21D	0.9300
C8—H8B	0.9700	C22—H22A	0.9600
C8A—C9A	1.527 (10)	C22—H22B	0.9600
C8A—H8C	0.9700	C22—H22C	0.9600
C8A—H8D	0.9700	C22A—H22D	0.9600
C9—C10	1.543 (10)	C22A—H22E	0.9600
C9—H9	0.9800	C22A—H22F	0.9600

C18—O1—C16	109.4 (7)	C12A—C11A—C19A	109.6 (6)
C18A—O1A—C16A	110.4 (7)	C1A—C11A—C10A	106.2 (6)
C3—O2—C1	119.3 (7)	C12A—C11A—C10A	114.8 (6)
C3A—O2A—C1A	119.2 (6)	C19A—C11A—C10A	109.3 (5)
C5—O4—H4	109.5	C13—C12—C11	114.0 (7)
C5A—O4A—H4A	109.5	C13—C12—H12A	108.8
C9—O5—H5	109.5	C11—C12—H12A	108.8
C9A—O5A—H5B	109.5	C13—C12—H12B	108.8
O2—C1—C11	112.1 (6)	C11—C12—H12B	108.8
O2—C1—H1A	109.2	H12A—C12—H12B	107.7
C11—C1—H1A	109.2	C13A—C12A—C11A	114.0 (6)
O2—C1—H1B	109.2	C13A—C12A—H12C	108.8
C11—C1—H1B	109.2	C11A—C12A—H12C	108.8
H1A—C1—H1B	107.9	C13A—C12A—H12D	108.8
O2A—C1A—C11A	112.9 (6)	C11A—C12A—H12D	108.8
O2A—C1A—H1C	109.0	H12C—C12A—H12D	107.7
C11A—C1A—H1C	109.0	C14—C13—C12	109.3 (7)
O2A—C1A—H1D	109.0	C14—C13—H13A	109.8
C11A—C1A—H1D	109.0	C12—C13—H13A	109.8
H1C—C1A—H1D	107.8	C14—C13—H13B	109.8
O3—C3—O2	118.9 (8)	C12—C13—H13B	109.8
O3—C3—C4	122.1 (8)	H13A—C13—H13B	108.3
O2—C3—C4	119.0 (7)	C14A—C13A—C12A	109.3 (7)
O3A—C3A—O2A	118.1 (7)	C14A—C13A—H13C	109.8
O3A—C3A—C4A	122.6 (7)	C12A—C13A—H13C	109.8
O2A—C3A—C4A	119.2 (7)	C14A—C13A—H13D	109.8
C3—C4—C5	109.0 (6)	C12A—C13A—H13D	109.8
C3—C4—C20	111.0 (6)	H13C—C13A—H13D	108.3
C5—C4—C20	96.6 (6)	C13—C14—C15	113.4 (7)
C3—C4—C10	118.2 (7)	C13—C14—H14A	108.9
C5—C4—C10	109.9 (6)	C15—C14—H14A	108.9
C20—C4—C10	110.0 (6)	C13—C14—H14B	108.9
C3A—C4A—C20A	109.5 (6)	C15—C14—H14B	108.9
C3A—C4A—C5A	110.0 (6)	H14A—C14—H14B	107.7
C20A—C4A—C5A	98.2 (6)	C13A—C14A—C15A	112.1 (7)
C3A—C4A—C10A	117.8 (6)	C13A—C14A—H14C	109.2
C20A—C4A—C10A	110.3 (6)	C15A—C14A—H14C	109.2
C5A—C4A—C10A	109.3 (6)	C13A—C14A—H14D	109.2
O4—C5—C6	113.5 (7)	C15A—C14A—H14D	109.2
O4—C5—C4	115.1 (6)	H14C—C14A—H14D	107.9
C6—C5—C4	101.4 (6)	C16—C15—C14	111.3 (7)
O4—C5—H5A	108.8	C16—C15—C22	110.1 (7)
C6—C5—H5A	108.8	C14—C15—C22	109.6 (7)
C4—C5—H5A	108.8	C16—C15—C19	98.0 (6)
O4A—C5A—C6A	111.6 (7)	C14—C15—C19	109.4 (7)
O4A—C5A—C4A	116.8 (6)	C22—C15—C19	117.9 (6)
C6A—C5A—C4A	102.0 (6)	C16A—C15A—C14A	109.4 (7)
O4A—C5A—H5C	108.7	C16A—C15A—C22A	109.0 (7)
C6A—C5A—H5C	108.7	C14A—C15A—C22A	109.7 (7)
C4A—C5A—H5C	108.7	C16A—C15A—C19A	99.7 (6)
C21—C6—C5	126.3 (8)	C14A—C15A—C19A	110.4 (6)
C21—C6—C7	126.7 (8)	C22A—C15A—C19A	118.1 (6)
C5—C6—C7	106.6 (7)	O1—C16—C15	105.5 (7)
C21A—C6A—C5A	125.1 (8)	O1—C16—H16A	110.6
C21A—C6A—C7A	126.0 (8)	C15—C16—H16A	110.6
C5A—C6A—C7A	108.6 (6)	O1—C16—H16B	110.6
C6—C7—C8	109.5 (6)	C15—C16—H16B	110.6
C6—C7—C20	103.0 (7)	H16A—C16—H16B	108.8
C8—C7—C20	108.3 (6)	O1A—C16A—C15A	105.8 (7)
C6—C7—H7	111.9	O1A—C16A—H16C	110.6
C8—C7—H7	111.9	C15A—C16A—H16C	110.6
C20—C7—H7	111.9	O1A—C16A—H16D	110.6
C6A—C7A—C8A	110.8 (7)	C15A—C16A—H16D	110.6
C6A—C7A—C20A	102.6 (6)	H16C—C16A—H16D	108.7
C8A—C7A—C20A	109.1 (6)	O6—C18—O1	120.3 (10)
C6A—C7A—H7A	111.4	O6—C18—C19	130.6 (9)
C8A—C7A—H7A	111.4	O1—C18—C19	109.2 (8)
C20A—C7A—H7A	111.4	O6A—C18A—O1A	121.7 (9)
C9—C8—C7	111.5 (7)	O6A—C18A—C19A	128.5 (8)
C9—C8—H8A	109.3	O1A—C18A—C19A	109.8 (8)
C7—C8—H8A	109.3	C18—C19—C11	114.9 (7)
C9—C8—H8B	109.3	C18—C19—C15	100.8 (6)
C7—C8—H8B	109.3	C11—C19—C15	117.7 (6)
H8A—C8—H8B	108.0	C18—C19—H19	107.6
C7A—C8A—C9A	112.8 (6)	C11—C19—H19	107.6
C7A—C8A—H8C	109.0	C15—C19—H19	107.6
C9A—C8A—H8C	109.0	C18A—C19A—C15A	101.6 (6)
C7A—C8A—H8D	109.0	C18A—C19A—C11A	117.7 (6)
C9A—C8A—H8D	109.0	C15A—C19A—C11A	116.8 (6)
H8C—C8A—H8D	107.8	C18A—C19A—H19A	106.6
O5—C9—C8	110.8 (6)	C15A—C19A—H19A	106.6
O5—C9—C10	109.4 (6)	C11A—C19A—H19A	106.6
C8—C9—C10	111.9 (6)	C7—C20—C4	100.3 (6)
O5—C9—H9	108.2	C7—C20—H20A	111.7
C8—C9—H9	108.2	C4—C20—H20A	111.7
C10—C9—H9	108.2	C7—C20—H20B	111.7
O5A—C9A—C8A	110.4 (6)	C4—C20—H20B	111.7
O5A—C9A—C10A	108.9 (5)	H20A—C20—H20B	109.5
C8A—C9A—C10A	112.4 (6)	C7A—C20A—C4A	100.0 (6)
O5A—C9A—H9A	108.4	C7A—C20A—H20C	111.8
C8A—C9A—H9A	108.4	C4A—C20A—H20C	111.8
C10A—C9A—H9A	108.4	C7A—C20A—H20D	111.8
C9—C10—C11	114.6 (6)	C4A—C20A—H20D	111.8
C9—C10—C4	112.4 (6)	H20C—C20A—H20D	109.5
C11—C10—C4	111.1 (6)	C6—C21—H21A	120.0
C9—C10—H10	106.0	C6—C21—H21B	120.0
C11—C10—H10	106.0	H21A—C21—H21B	120.0
C4—C10—H10	106.0	C6A—C21A—H21C	120.0
C9A—C10A—C11A	115.3 (5)	C6A—C21A—H21D	120.0
C9A—C10A—C4A	112.9 (5)	H21C—C21A—H21D	120.0
C11A—C10A—C4A	111.1 (5)	C15—C22—H22A	109.5
C9A—C10A—H10A	105.5	C15—C22—H22B	109.5
C11A—C10A—H10A	105.5	H22A—C22—H22B	109.5
C4A—C10A—H10A	105.5	C15—C22—H22C	109.5
C1—C11—C19	112.1 (6)	H22A—C22—H22C	109.5
C1—C11—C12	108.0 (6)	H22B—C22—H22C	109.5
C19—C11—C12	108.0 (6)	C15A—C22A—H22D	109.5
C1—C11—C10	105.5 (6)	C15A—C22A—H22E	109.5
C19—C11—C10	110.1 (6)	H22D—C22A—H22E	109.5
C12—C11—C10	113.2 (6)	C15A—C22A—H22F	109.5
C1A—C11A—C12A	105.4 (6)	H22D—C22A—H22F	109.5
C1A—C11A—C19A	111.5 (6)	H22E—C22A—H22F	109.5

C3—O2—C1—C11	−48.6 (10)	C9—C10—C11—C12	−31.4 (9)
C3A—O2A—C1A—C11A	−43.2 (9)	C4—C10—C11—C12	−160.1 (6)
C1—O2—C3—O3	−177.0 (7)	O2A—C1A—C11A—C12A	−171.7 (6)
C1—O2—C3—C4	2.0 (10)	O2A—C1A—C11A—C19A	−52.9 (8)
C1A—O2A—C3A—O3A	178.3 (7)	O2A—C1A—C11A—C10A	66.1 (8)
C1A—O2A—C3A—C4A	−4.4 (10)	C9A—C10A—C11A—C1A	87.5 (7)
O3—C3—C4—C5	−33.7 (10)	C4A—C10A—C11A—C1A	−42.6 (7)
O2—C3—C4—C5	147.3 (7)	C9A—C10A—C11A—C12A	−28.5 (8)
O3—C3—C4—C20	71.5 (10)	C4A—C10A—C11A—C12A	−158.6 (6)
O2—C3—C4—C20	−107.5 (8)	C9A—C10A—C11A—C19A	−152.1 (6)
O3—C3—C4—C10	−160.1 (7)	C4A—C10A—C11A—C19A	77.8 (7)
O2—C3—C4—C10	21.0 (10)	C1—C11—C12—C13	173.9 (7)
O3A—C3A—C4A—C20A	75.2 (9)	C19—C11—C12—C13	52.5 (9)
O2A—C3A—C4A—C20A	−102.0 (8)	C10—C11—C12—C13	−69.7 (9)
O3A—C3A—C4A—C5A	−31.7 (10)	C1A—C11A—C12A—C13A	169.9 (6)
O2A—C3A—C4A—C5A	151.2 (7)	C19A—C11A—C12A—C13A	49.8 (8)
O3A—C3A—C4A—C10A	−157.8 (7)	C10A—C11A—C12A—C13A	−73.7 (8)
O2A—C3A—C4A—C10A	25.1 (10)	C11—C12—C13—C14	−59.8 (10)
C3—C4—C5—O4	−71.1 (9)	C11A—C12A—C13A—C14A	−59.2 (9)
C20—C4—C5—O4	174.0 (7)	C12—C13—C14—C15	59.2 (10)
C10—C4—C5—O4	59.9 (9)	C12A—C13A—C14A—C15A	60.9 (9)
C3—C4—C5—C6	165.9 (6)	C13—C14—C15—C16	−159.2 (8)
C20—C4—C5—C6	51.0 (7)	C13—C14—C15—C22	78.7 (9)
C10—C4—C5—C6	−63.1 (7)	C13—C14—C15—C19	−52.0 (9)
C3A—C4A—C5A—O4A	−78.8 (9)	C13A—C14A—C15A—C16A	−163.1 (7)
C20A—C4A—C5A—O4A	167.0 (6)	C13A—C14A—C15A—C22A	77.4 (8)
C10A—C4A—C5A—O4A	52.0 (8)	C13A—C14A—C15A—C19A	−54.4 (9)
C3A—C4A—C5A—C6A	159.4 (6)	C18—O1—C16—C15	25.3 (9)
C20A—C4A—C5A—C6A	45.1 (8)	C14—C15—C16—O1	75.6 (8)
C10A—C4A—C5A—C6A	−69.9 (7)	C22—C15—C16—O1	−162.7 (6)
O4—C5—C6—C21	19.4 (12)	C19—C15—C16—O1	−39.0 (8)
C4—C5—C6—C21	143.5 (9)	C18A—O1A—C16A—C15A	23.0 (9)
O4—C5—C6—C7	−153.2 (6)	C14A—C15A—C16A—O1A	81.6 (8)
C4—C5—C6—C7	−29.1 (7)	C22A—C15A—C16A—O1A	−158.5 (6)
O4A—C5A—C6A—C21A	27.6 (12)	C19A—C15A—C16A—O1A	−34.2 (7)
C4A—C5A—C6A—C21A	153.0 (9)	C16—O1—C18—O6	−178.1 (9)
O4A—C5A—C6A—C7A	−146.7 (7)	C16—O1—C18—C19	1.0 (10)
C4A—C5A—C6A—C7A	−21.2 (9)	C16A—O1A—C18A—O6A	177.5 (8)
C21—C6—C7—C8	−62.3 (11)	C16A—O1A—C18A—C19A	−0.6 (9)
C5—C6—C7—C8	110.3 (7)	O6—C18—C19—C11	25.6 (14)
C21—C6—C7—C20	−177.4 (8)	O1—C18—C19—C11	−153.3 (7)
C5—C6—C7—C20	−4.9 (8)	O6—C18—C19—C15	153.3 (11)
C21A—C6A—C7A—C8A	−69.4 (11)	O1—C18—C19—C15	−25.6 (9)
C5A—C6A—C7A—C8A	104.7 (7)	C1—C11—C19—C18	−47.2 (9)
C21A—C6A—C7A—C20A	174.3 (9)	C12—C11—C19—C18	71.6 (8)
C5A—C6A—C7A—C20A	−11.5 (9)	C10—C11—C19—C18	−164.3 (6)
C6—C7—C8—C9	−81.4 (8)	C1—C11—C19—C15	−165.8 (6)
C20—C7—C8—C9	30.3 (9)	C12—C11—C19—C15	−46.9 (9)
C6A—C7A—C8A—C9A	−83.1 (8)	C10—C11—C19—C15	77.2 (8)
C20A—C7A—C8A—C9A	29.0 (9)	C16—C15—C19—C18	37.5 (8)
C7—C8—C9—O5	−87.8 (7)	C14—C15—C19—C18	−78.5 (8)
C7—C8—C9—C10	34.6 (9)	C22—C15—C19—C18	155.4 (7)
C7A—C8A—C9A—O5A	−88.3 (7)	C16—C15—C19—C11	163.3 (7)
C7A—C8A—C9A—C10A	33.5 (9)	C14—C15—C19—C11	47.3 (9)
O5—C9—C10—C11	−56.6 (8)	C22—C15—C19—C11	−78.8 (9)
C8—C9—C10—C11	−179.8 (6)	O6A—C18A—C19A—C15A	160.9 (8)
O5—C9—C10—C4	71.4 (8)	O1A—C18A—C19A—C15A	−21.2 (8)
C8—C9—C10—C4	−51.8 (8)	O6A—C18A—C19A—C11A	32.0 (12)
C3—C4—C10—C9	−127.3 (7)	O1A—C18A—C19A—C11A	−150.1 (6)
C5—C4—C10—C9	106.8 (7)	C16A—C15A—C19A—C18A	32.2 (7)
C20—C4—C10—C9	1.6 (8)	C14A—C15A—C19A—C18A	−82.8 (7)
C3—C4—C10—C11	2.5 (9)	C22A—C15A—C19A—C18A	150.0 (7)
C5—C4—C10—C11	−123.4 (6)	C16A—C15A—C19A—C11A	161.7 (6)
C20—C4—C10—C11	131.5 (6)	C14A—C15A—C19A—C11A	46.7 (8)
O5A—C9A—C10A—C11A	−53.7 (7)	C22A—C15A—C19A—C11A	−80.5 (8)
C8A—C9A—C10A—C11A	−176.3 (6)	C1A—C11A—C19A—C18A	−38.9 (9)
O5A—C9A—C10A—C4A	75.5 (7)	C12A—C11A—C19A—C18A	77.4 (8)
C8A—C9A—C10A—C4A	−47.1 (8)	C10A—C11A—C19A—C18A	−156.0 (6)
C3A—C4A—C10A—C9A	−129.7 (7)	C1A—C11A—C19A—C15A	−160.3 (6)
C20A—C4A—C10A—C9A	−3.1 (8)	C12A—C11A—C19A—C15A	−44.0 (8)
C5A—C4A—C10A—C9A	103.9 (7)	C10A—C11A—C19A—C15A	82.7 (7)
C3A—C4A—C10A—C11A	1.6 (9)	C6—C7—C20—C4	36.9 (7)
C20A—C4A—C10A—C11A	128.3 (6)	C8—C7—C20—C4	−79.1 (7)
C5A—C4A—C10A—C11A	−124.8 (6)	C3—C4—C20—C7	−167.3 (6)
O2—C1—C11—C19	−52.1 (9)	C5—C4—C20—C7	−54.0 (7)
O2—C1—C11—C12	−170.9 (7)	C10—C4—C20—C7	59.9 (7)
O2—C1—C11—C10	67.8 (8)	C6A—C7A—C20A—C4A	39.8 (8)
C9—C10—C11—C1	86.4 (7)	C8A—C7A—C20A—C4A	−77.7 (7)
C4—C10—C11—C1	−42.3 (7)	C3A—C4A—C20A—C7A	−167.0 (6)
C9—C10—C11—C19	−152.5 (6)	C5A—C4A—C20A—C7A	−52.3 (7)
C4—C10—C11—C19	78.8 (7)	C10A—C4A—C20A—C7A	61.9 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3A	0.82	2.46	3.159 (8)	144
O4A—H4A···O3	0.82	1.94	2.750 (8)	168
O5—H5···O3Aⁱ	0.82	1.97	2.787 (8)	175
O5A—H5B···O6Aⁱⁱ	0.82	2.11	2.903 (9)	164

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆O₆
M_r	362.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	12.2614 (15), 15.6668 (18), 18.697 (2)
V (Å³)	3591.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.961, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	17440, 3556, 1970
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.237, 1.10
No. of reflections	3556
No. of parameters	472
No. of restraints	1896
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.56

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3A	0.82	2.46	3.159 (8)	143.9
O4A—H4A···O3	0.82	1.94	2.750 (8)	168.0
O5—H5···O3Aⁱ	0.82	1.97	2.787 (8)	175.0
O5A—H5B···O6Aⁱⁱ	0.82	2.11	2.903 (9)	163.9

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z.

Comparison of the puckering parameters (Å, °) for the six- and five-membered rings of molecules 1 and 2 top

Molecule	A			B
Puckering parameters	Q	θ	ϕ	Q	θ	ϕ
Ring A, A"	0.545 (9)	171.2 (9)	296 (6)	0.546 (8)	168.9 (8)	315 (5)
Ring B, B"	0.584 (9)	65.6 (8)	91.8 (8)	0.582 (8)	68.4 (8)	95.2 (7)
Ring C, C"	0.861 (8)	80.2 (5)	286.4 (6)	0.837 (8)	78.9 (5)	288.8 (6)

Puckering parameters		Q2	ϕ2		Q2	ϕ2
Ring D, D"		0.561 (9)	174.6 (9)		0.530 (9)	167.1 (9)
Ring E, E"		0.412 (9)	254.0 (13)		0.355 (9)	251.8 (14)

Ring A: C11···C15-C19 Ring A": C11A···C15A-C19A Ring B: O2-C1-C11-C10-C4-C3 Ring B": O2A-C1A-C11A-C10A-C4A-C3A Ring C: C4-C10-C9-C8-C7-C20 Ring C": C4A-C10A-C9A-C8A-C7A-C20A Ring D: C4···C7-C20 Ring D": C4A···C7A-C20A Ring E: O1-C16-C15-C19-C18 Ring E": O1A-C16A-C15A-C19A-C18A

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page