3,6-Di-O-acetyl­swietenolide 0.25-hydrate

Fowles, R.G.; Mootoo, B.S.; Ramsewak, R.; Reynolds, W.; Lough, A.J.

doi:10.1107/S1600536806054432

3,6-Di-O-acetylswietenolide 0.25-hydrate

R. G. Fowles, B. S. Mootoo, R. Ramsewak, W. Reynolds and A. J. Lough

The title compound, C₃₁H₃₈O₁₀·0.25H₂O, was extracted from Swietenia macrophylla, a plant belonging to the Meliaceae family. The crystal structure is stabilized by O—H

O and weak C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054432/hg2158sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054432/hg2158Isup2.hkl Contains datablock I

CCDC reference: 636676

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.039
wR factor = 0.098
Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  O8     ..  C25     ..       2.88 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H7A    ..  H15A    ..       1.98 Ang.
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........

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           27.47
           From the CIF: _reflns_number_total               3660
           Count of symmetry unique reflns         3668
           Completeness (_total/calc)             99.78%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29    = .          R

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

Computing details top

Data collection: COLLECT (Bruker Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

3,6-O,O-Diacetylswietenolide 0.25-hydrate top

Crystal data top

C₃₁H₃₈O₁₀·0.25H₂O	F(000) = 1226
M_r = 575.12	D_x = 1.331 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24546 reflections
a = 12.5030 (2) Å	θ = 2.9–27.5°
b = 13.7366 (2) Å	µ = 0.10 mm⁻¹
c = 16.7164 (4) Å	T = 150 K
V = 2871.02 (9) Å³	Needle, colourless
Z = 4	0.28 × 0.20 × 0.18 mm

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	3660 independent reflections
Radiation source: fine-focus sealed tube	2970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
φ scans, and ω scans with κ offsets	h = −14→16
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −17→17
T_min = 0.905, T_max = 0.988	l = −21→19
24546 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0534P)² + 0.3768P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3660 reflections	Δρ_max = 0.18 e Å⁻³
382 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL/PC (Sheldrick, 2001), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0103 (14)

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	Occ. (<1)
O1	0.26234 (14)	0.14471 (13)	0.54925 (10)	0.0412 (4)
O2	0.23418 (17)	0.07301 (14)	0.66430 (11)	0.0535 (5)
O3	0.34446 (14)	0.17750 (13)	0.29332 (10)	0.0414 (4)
O4	0.02444 (15)	0.65269 (15)	0.68120 (11)	0.0494 (5)
O5	0.32497 (14)	0.44549 (14)	0.69337 (10)	0.0410 (4)
O6	0.4330 (2)	0.4697 (2)	0.79861 (15)	0.0856 (8)
O7	0.28205 (13)	0.70216 (11)	0.46856 (10)	0.0334 (4)
O8	0.24304 (16)	0.69452 (13)	0.33789 (11)	0.0480 (5)
O9	0.38944 (13)	0.46334 (11)	0.43976 (11)	0.0365 (4)
O10	0.45104 (13)	0.61471 (11)	0.41759 (10)	0.0360 (4)
C1	0.13840 (17)	0.27738 (17)	0.50867 (13)	0.0284 (5)
C2	0.13062 (18)	0.36442 (16)	0.45148 (13)	0.0297 (5)
H2A	0.2002	0.3988	0.4502	0.036*
H2B	0.1154	0.3405	0.3968	0.036*
C3	0.04339 (19)	0.43555 (18)	0.47653 (14)	0.0328 (5)
H3A	−0.0268	0.4026	0.4726	0.039*
H3B	0.0429	0.4910	0.4387	0.039*
C4	0.05712 (18)	0.47488 (16)	0.56180 (14)	0.0319 (5)
H4A	−0.0171	0.4869	0.5818	0.038*
C5	0.10451 (18)	0.40047 (18)	0.61844 (13)	0.0317 (5)
C6	0.13541 (18)	0.31132 (17)	0.59544 (13)	0.0296 (5)
C7	0.1698 (2)	0.23551 (19)	0.65587 (14)	0.0402 (6)
H7A	0.2194	0.2670	0.6941	0.048*
H7B	0.1058	0.2152	0.6864	0.048*
C8	0.2232 (2)	0.1454 (2)	0.62445 (15)	0.0388 (6)
C9	0.24956 (18)	0.22997 (17)	0.49757 (14)	0.0313 (5)
H9A	0.3055	0.2789	0.5122	0.038*
C10	0.27362 (18)	0.19230 (16)	0.41549 (14)	0.0320 (5)
C11	0.2368 (2)	0.10369 (18)	0.37960 (17)	0.0437 (6)
H11A	0.1900	0.0573	0.4031	0.052*
C12	0.2808 (2)	0.09846 (19)	0.30682 (17)	0.0452 (6)
H12A	0.2693	0.0471	0.2698	0.054*
C13	0.33851 (19)	0.23301 (18)	0.36070 (14)	0.0358 (5)
H13A	0.3754	0.2928	0.3681	0.043*
C14	0.04822 (19)	0.20452 (17)	0.49362 (15)	0.0344 (5)
H14A	−0.0209	0.2371	0.5001	0.052*
H14B	0.0537	0.1508	0.5320	0.052*
H14C	0.0541	0.1789	0.4391	0.052*
C15	0.1067 (2)	0.4326 (2)	0.70476 (14)	0.0383 (6)
H15A	0.1480	0.3847	0.7364	0.046*
H15B	0.0327	0.4335	0.7258	0.046*
C16	0.1572 (2)	0.5352 (2)	0.71583 (14)	0.0387 (6)
H16A	0.1419	0.5576	0.7716	0.046*
C17	0.0958 (2)	0.59886 (19)	0.65894 (15)	0.0377 (6)
C18	0.11776 (18)	0.57665 (17)	0.57052 (14)	0.0322 (5)
C19	0.0624 (2)	0.65428 (19)	0.51965 (15)	0.0386 (6)
H19A	−0.0146	0.6538	0.5309	0.058*
H19B	0.0742	0.6403	0.4629	0.058*
H19C	0.0919	0.7184	0.5326	0.058*
C20	0.24197 (17)	0.56439 (16)	0.55623 (13)	0.0299 (5)
H20A	0.2543	0.4925	0.5563	0.036*
C21	0.31012 (19)	0.60348 (19)	0.62724 (14)	0.0363 (5)
C22	0.2793 (2)	0.5425 (2)	0.70149 (15)	0.0402 (6)
H22A	0.3121	0.5739	0.7495	0.048*
C23	0.2910 (2)	0.7120 (2)	0.64773 (17)	0.0461 (7)
H23A	0.3206	0.7529	0.6051	0.069*
H23B	0.3262	0.7277	0.6985	0.069*
H23C	0.2140	0.7241	0.6525	0.069*
C24	0.43104 (19)	0.5914 (2)	0.61175 (16)	0.0446 (7)
H24A	0.4453	0.5254	0.5924	0.067*
H24B	0.4705	0.6026	0.6616	0.067*
H24C	0.4541	0.6387	0.5714	0.067*
C25	0.4033 (2)	0.4199 (3)	0.74428 (17)	0.0545 (8)
C26	0.4504 (3)	0.3230 (3)	0.7240 (2)	0.0676 (10)
H26A	0.4411	0.2785	0.7693	0.101*
H26B	0.5268	0.3306	0.7126	0.101*
H26C	0.4142	0.2963	0.6768	0.101*
C27	0.26202 (19)	0.74272 (17)	0.39643 (15)	0.0352 (5)
C28	0.2646 (2)	0.85107 (18)	0.39891 (19)	0.0487 (7)
H28A	0.1974	0.8769	0.3774	0.073*
H28B	0.3246	0.8748	0.3666	0.073*
H28C	0.2734	0.8728	0.4544	0.073*
C29	0.27521 (18)	0.59806 (16)	0.47185 (13)	0.0294 (5)
H29A	0.2170	0.5779	0.4343	0.035*
C30	0.37850 (18)	0.55084 (16)	0.44242 (13)	0.0289 (5)
C31	0.5518 (2)	0.5740 (2)	0.38994 (16)	0.0412 (6)
H31A	0.5925	0.6243	0.3616	0.062*
H31B	0.5376	0.5195	0.3537	0.062*
H31C	0.5932	0.5509	0.4359	0.062*
O1W	0.3507 (8)	−0.0739 (8)	0.6079 (6)	0.077 (3)*	0.25
H1W	0.3137	−0.0277	0.6255	0.116*	0.25
H2W	0.4080	−0.0626	0.6325	0.116*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0400 (9)	0.0471 (10)	0.0364 (9)	0.0104 (8)	0.0006 (8)	0.0107 (8)
O2	0.0631 (12)	0.0517 (11)	0.0457 (11)	0.0062 (10)	−0.0022 (10)	0.0192 (10)
O3	0.0464 (10)	0.0446 (10)	0.0334 (9)	0.0058 (8)	0.0027 (8)	0.0001 (8)
O4	0.0454 (10)	0.0569 (11)	0.0459 (11)	0.0050 (9)	0.0121 (9)	−0.0167 (10)
O5	0.0408 (9)	0.0564 (11)	0.0258 (8)	0.0041 (8)	−0.0023 (7)	0.0005 (8)
O6	0.0927 (19)	0.109 (2)	0.0552 (14)	−0.0016 (16)	−0.0388 (14)	−0.0022 (15)
O7	0.0392 (9)	0.0256 (8)	0.0353 (9)	0.0014 (7)	0.0036 (7)	−0.0017 (7)
O8	0.0637 (12)	0.0437 (10)	0.0365 (10)	0.0017 (9)	0.0000 (9)	0.0041 (9)
O9	0.0348 (9)	0.0296 (9)	0.0451 (10)	0.0026 (7)	0.0063 (8)	−0.0014 (8)
O10	0.0335 (8)	0.0337 (8)	0.0407 (9)	−0.0006 (7)	0.0092 (8)	−0.0003 (7)
C1	0.0259 (11)	0.0329 (12)	0.0264 (11)	−0.0017 (9)	0.0005 (9)	−0.0013 (9)
C2	0.0321 (11)	0.0338 (12)	0.0232 (10)	−0.0011 (9)	−0.0002 (9)	−0.0016 (10)
C3	0.0332 (12)	0.0359 (12)	0.0292 (11)	0.0014 (10)	−0.0023 (10)	−0.0015 (10)
C4	0.0253 (11)	0.0379 (12)	0.0326 (12)	0.0009 (9)	0.0060 (10)	−0.0019 (10)
C5	0.0281 (11)	0.0408 (13)	0.0263 (11)	−0.0050 (10)	0.0035 (9)	0.0000 (10)
C6	0.0266 (11)	0.0375 (12)	0.0247 (10)	−0.0052 (9)	0.0010 (9)	0.0012 (10)
C7	0.0483 (14)	0.0451 (14)	0.0270 (12)	−0.0036 (12)	−0.0016 (11)	0.0056 (11)
C8	0.0347 (12)	0.0486 (15)	0.0331 (12)	−0.0031 (11)	−0.0040 (11)	0.0075 (12)
C9	0.0297 (12)	0.0347 (12)	0.0294 (11)	0.0004 (9)	−0.0008 (9)	0.0048 (10)
C10	0.0281 (11)	0.0321 (12)	0.0358 (12)	0.0042 (9)	0.0008 (10)	0.0020 (10)
C11	0.0510 (15)	0.0304 (12)	0.0497 (15)	−0.0003 (11)	0.0112 (13)	−0.0019 (12)
C12	0.0528 (15)	0.0360 (13)	0.0469 (15)	0.0042 (12)	0.0039 (13)	−0.0069 (12)
C13	0.0387 (13)	0.0389 (13)	0.0298 (12)	0.0014 (10)	−0.0013 (10)	0.0005 (10)
C14	0.0305 (11)	0.0371 (13)	0.0358 (13)	−0.0041 (10)	−0.0001 (11)	−0.0020 (11)
C15	0.0378 (13)	0.0491 (14)	0.0281 (12)	−0.0020 (11)	0.0059 (10)	−0.0015 (11)
C16	0.0431 (14)	0.0495 (15)	0.0236 (11)	−0.0031 (12)	0.0047 (10)	−0.0098 (11)
C17	0.0336 (12)	0.0423 (13)	0.0373 (13)	−0.0036 (11)	0.0069 (11)	−0.0091 (11)
C18	0.0305 (12)	0.0357 (12)	0.0304 (12)	0.0009 (10)	0.0034 (10)	−0.0054 (10)
C19	0.0342 (13)	0.0389 (13)	0.0428 (13)	0.0055 (11)	0.0048 (11)	−0.0048 (12)
C20	0.0302 (11)	0.0309 (11)	0.0285 (11)	−0.0005 (9)	0.0020 (10)	−0.0041 (10)
C21	0.0341 (12)	0.0441 (14)	0.0306 (12)	−0.0052 (10)	0.0031 (10)	−0.0069 (11)
C22	0.0411 (14)	0.0542 (15)	0.0254 (11)	−0.0037 (12)	0.0005 (11)	−0.0095 (11)
C23	0.0475 (15)	0.0505 (15)	0.0402 (14)	−0.0091 (12)	0.0049 (12)	−0.0190 (13)
C24	0.0326 (13)	0.0652 (18)	0.0359 (14)	−0.0075 (12)	−0.0025 (11)	−0.0064 (13)
C25	0.0472 (15)	0.085 (2)	0.0311 (14)	0.0005 (16)	−0.0039 (13)	0.0087 (15)
C26	0.0542 (18)	0.098 (3)	0.0508 (17)	0.0233 (19)	0.0046 (15)	0.0210 (18)
C27	0.0310 (12)	0.0351 (12)	0.0395 (14)	0.0029 (10)	0.0062 (11)	0.0032 (11)
C28	0.0441 (15)	0.0340 (13)	0.0679 (19)	0.0037 (12)	−0.0004 (14)	0.0100 (14)
C29	0.0332 (12)	0.0260 (11)	0.0291 (11)	0.0017 (9)	0.0026 (10)	−0.0007 (9)
C30	0.0312 (11)	0.0316 (13)	0.0240 (10)	−0.0004 (9)	−0.0003 (9)	0.0013 (9)
C31	0.0318 (12)	0.0488 (14)	0.0430 (14)	−0.0001 (11)	0.0117 (11)	−0.0017 (12)

Geometric parameters (Å, º) top

O1—C8	1.349 (3)	C14—H14B	0.9800
O1—C9	1.464 (3)	C14—H14C	0.9800
O2—C8	1.205 (3)	C15—C16	1.555 (4)
O3—C13	1.362 (3)	C15—H15A	0.9900
O3—C12	1.365 (3)	C15—H15B	0.9900
O4—C17	1.217 (3)	C16—C17	1.503 (4)
O5—C25	1.344 (3)	C16—C22	1.548 (3)
O5—C22	1.457 (3)	C16—H16A	1.0000
O6—C25	1.196 (4)	C17—C18	1.534 (3)
O7—C27	1.352 (3)	C18—C19	1.530 (3)
O7—C29	1.434 (3)	C18—C20	1.580 (3)
O8—C27	1.205 (3)	C19—H19A	0.9800
O9—C30	1.210 (3)	C19—H19B	0.9800
O10—C30	1.328 (3)	C19—H19C	0.9800
O10—C31	1.454 (3)	C20—C29	1.541 (3)
C1—C6	1.524 (3)	C20—C21	1.557 (3)
C1—C14	1.528 (3)	C20—H20A	1.0000
C1—C2	1.534 (3)	C21—C24	1.543 (3)
C1—C9	1.546 (3)	C21—C22	1.546 (4)
C2—C3	1.523 (3)	C21—C23	1.548 (4)
C2—H2A	0.9900	C22—H22A	1.0000
C2—H2B	0.9900	C23—H23A	0.9800
C3—C4	1.534 (3)	C23—H23B	0.9800
C3—H3A	0.9900	C23—H23C	0.9800
C3—H3B	0.9900	C24—H24A	0.9800
C4—C5	1.514 (3)	C24—H24B	0.9800
C4—C18	1.597 (3)	C24—H24C	0.9800
C4—H4A	1.0000	C25—C26	1.495 (5)
C5—C6	1.340 (3)	C26—H26A	0.9800
C5—C15	1.509 (3)	C26—H26B	0.9800
C6—C7	1.513 (3)	C26—H26C	0.9800
C7—C8	1.501 (4)	C27—C28	1.489 (3)
C7—H7A	0.9900	C28—H28A	0.9800
C7—H7B	0.9900	C28—H28B	0.9800
C9—C10	1.497 (3)	C28—H28C	0.9800
C9—H9A	1.0000	C29—C30	1.527 (3)
C10—C13	1.345 (3)	C29—H29A	1.0000
C10—C11	1.433 (4)	C31—H31A	0.9800
C11—C12	1.337 (4)	C31—H31B	0.9800
C11—H11A	0.9500	C31—H31C	0.9800
C12—H12A	0.9500	O1W—H1W	0.8401
C13—H13A	0.9500	O1W—H2W	0.8401
C14—H14A	0.9800

C8—O1—C9	120.31 (19)	O4—C17—C16	122.3 (2)
C13—O3—C12	106.06 (19)	O4—C17—C18	123.1 (2)
C25—O5—C22	117.8 (2)	C16—C17—C18	113.7 (2)
C27—O7—C29	115.74 (18)	C19—C18—C17	108.4 (2)
C30—O10—C31	115.91 (18)	C19—C18—C20	115.8 (2)
C6—C1—C14	109.81 (18)	C17—C18—C20	110.04 (19)
C6—C1—C2	110.68 (18)	C19—C18—C4	110.15 (19)
C14—C1—C2	111.17 (18)	C17—C18—C4	100.21 (19)
C6—C1—C9	105.38 (18)	C20—C18—C4	111.07 (18)
C14—C1—C9	111.56 (18)	C18—C19—H19A	109.5
C2—C1—C9	108.09 (17)	C18—C19—H19B	109.5
C3—C2—C1	111.97 (18)	H19A—C19—H19B	109.5
C3—C2—H2A	109.2	C18—C19—H19C	109.5
C1—C2—H2A	109.2	H19A—C19—H19C	109.5
C3—C2—H2B	109.2	H19B—C19—H19C	109.5
C1—C2—H2B	109.2	C29—C20—C21	116.53 (19)
H2A—C2—H2B	107.9	C29—C20—C18	111.80 (19)
C2—C3—C4	113.66 (19)	C21—C20—C18	112.70 (18)
C2—C3—H3A	108.8	C29—C20—H20A	104.8
C4—C3—H3A	108.8	C21—C20—H20A	104.8
C2—C3—H3B	108.8	C18—C20—H20A	104.8
C4—C3—H3B	108.8	C24—C21—C22	108.7 (2)
H3A—C3—H3B	107.7	C24—C21—C23	107.0 (2)
C5—C4—C3	112.77 (19)	C22—C21—C23	107.8 (2)
C5—C4—C18	110.37 (18)	C24—C21—C20	111.8 (2)
C3—C4—C18	116.51 (19)	C22—C21—C20	106.79 (19)
C5—C4—H4A	105.4	C23—C21—C20	114.6 (2)
C3—C4—H4A	105.4	O5—C22—C21	108.84 (19)
C18—C4—H4A	105.4	O5—C22—C16	110.0 (2)
C6—C5—C15	122.4 (2)	C21—C22—C16	113.9 (2)
C6—C5—C4	123.4 (2)	O5—C22—H22A	108.0
C15—C5—C4	114.1 (2)	C21—C22—H22A	108.0
C5—C6—C7	121.3 (2)	C16—C22—H22A	108.0
C5—C6—C1	124.0 (2)	C21—C23—H23A	109.5
C7—C6—C1	114.7 (2)	C21—C23—H23B	109.5
C8—C7—C6	117.4 (2)	H23A—C23—H23B	109.5
C8—C7—H7A	107.9	C21—C23—H23C	109.5
C6—C7—H7A	107.9	H23A—C23—H23C	109.5
C8—C7—H7B	107.9	H23B—C23—H23C	109.5
C6—C7—H7B	107.9	C21—C24—H24A	109.5
H7A—C7—H7B	107.2	C21—C24—H24B	109.5
O2—C8—O1	117.9 (2)	H24A—C24—H24B	109.5
O2—C8—C7	122.5 (2)	C21—C24—H24C	109.5
O1—C8—C7	119.5 (2)	H24A—C24—H24C	109.5
O1—C9—C10	104.03 (18)	H24B—C24—H24C	109.5
O1—C9—C1	111.36 (17)	O6—C25—O5	123.9 (3)
C10—C9—C1	115.87 (18)	O6—C25—C26	124.0 (3)
O1—C9—H9A	108.4	O5—C25—C26	112.1 (3)
C10—C9—H9A	108.4	C25—C26—H26A	109.5
C1—C9—H9A	108.4	C25—C26—H26B	109.5
C13—C10—C11	105.2 (2)	H26A—C26—H26B	109.5
C13—C10—C9	127.0 (2)	C25—C26—H26C	109.5
C11—C10—C9	127.8 (2)	H26A—C26—H26C	109.5
C12—C11—C10	107.1 (2)	H26B—C26—H26C	109.5
C12—C11—H11A	126.4	O8—C27—O7	122.3 (2)
C10—C11—H11A	126.4	O8—C27—C28	125.2 (2)
C11—C12—O3	110.3 (2)	O7—C27—C28	112.5 (2)
C11—C12—H12A	124.8	C27—C28—H28A	109.5
O3—C12—H12A	124.8	C27—C28—H28B	109.5
C10—C13—O3	111.3 (2)	H28A—C28—H28B	109.5
C10—C13—H13A	124.4	C27—C28—H28C	109.5
O3—C13—H13A	124.4	H28A—C28—H28C	109.5
C1—C14—H14A	109.5	H28B—C28—H28C	109.5
C1—C14—H14B	109.5	O7—C29—C30	111.16 (18)
H14A—C14—H14B	109.5	O7—C29—C20	110.51 (18)
C1—C14—H14C	109.5	C30—C29—C20	113.30 (18)
H14A—C14—H14C	109.5	O7—C29—H29A	107.2
H14B—C14—H14C	109.5	C30—C29—H29A	107.2
C5—C15—C16	112.7 (2)	C20—C29—H29A	107.2
C5—C15—H15A	109.1	O9—C30—O10	124.5 (2)
C16—C15—H15A	109.1	O9—C30—C29	122.0 (2)
C5—C15—H15B	109.1	O10—C30—C29	113.43 (18)
C16—C15—H15B	109.1	O10—C31—H31A	109.5
H15A—C15—H15B	107.8	O10—C31—H31B	109.5
C17—C16—C22	111.6 (2)	H31A—C31—H31B	109.5
C17—C16—C15	104.2 (2)	O10—C31—H31C	109.5
C22—C16—C15	116.2 (2)	H31A—C31—H31C	109.5
C17—C16—H16A	108.2	H31B—C31—H31C	109.5
C22—C16—H16A	108.2	H1W—O1W—H2W	99.1
C15—C16—H16A	108.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.84	1.82	2.662 (11)	180
O1W—H2W···O6ⁱ	0.84	2.34	3.180 (11)	180
C2—H2A···O9	0.99	2.53	3.515 (3)	172
C3—H3B···O6ⁱⁱ	0.99	2.42	3.260 (3)	142
C7—H7A···O8ⁱⁱⁱ	0.99	2.51	3.372 (3)	146
C12—H12A···O2^iv	0.95	2.42	3.355 (3)	170
C15—H15A···O8ⁱⁱⁱ	0.99	2.43	3.396 (3)	164
C20—H20A···O5	1.00	2.54	3.000 (3)	108
C22—H22A···O6	1.00	2.24	2.707 (4)	107
C23—H23A···07	0.98	2.43	3.000 (3)	116
C24—H24C···O10	0.98	2.59	3.271 (3)	126
C26—H26A···O8ⁱⁱⁱ	0.98	2.60	3.087 (4)	111

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

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3,6-Di-O-acetyl­swietenolide 0.25-hydrate

Supporting information

Key indicators

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3,6-Di-O-acetylswietenolide 0.25-hydrate