Redetermination of 3,3,6,6-tetra­methyl-4a-hydroxy-9-(ortho-methoxy­phenyl)-2,3,4,4a,5,6,7,8,9,9a-deca­hydro-1H-xanthene-1,8-dione at 173 K

Bolte, M.; Degen, A.; Rühl, S.

doi:10.1107/S160053680100160X

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Redetermination of 3,3,6,6-tetramethyl-4a-hydroxy-9-(ortho-methoxyphenyl)-2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthene-1,8-dione at 173 K

M. Bolte, A. Degen and S. Rühl

The title compound, C₂₄H₃₀O₅, has been redetermined at 173 K. In contrast to the structure determination of Tu et al. [Chin. J. Struct. Chem. (Jiegou Huaxue) (1998), 17, 409-412] at room temperature, we were able to locate all H atoms. There is an intermolecular hydrogen bond between the hydroxyl group and the carbonyl O atom of the cyclohexenone ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100160X/na6041sup1.cif Contains datablocks rd8, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680100160X/na6041Isup2.hkl Contains datablock I

CCDC reference: 159758

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.111
Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_601  Alert C Structure contains solvent accessible VOIDS of      34.00 A   3


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The title compound, (I), was synthesized in the course of a search for twinned crystal structures (Bolte et al., 1997, 2001b; Bolte & Scholtyssik, 1997). These compounds can easily be prepared (Hünig et al., 1979). We hoped to find more twinned crystal structures in order to understand why some of these simple compounds containing the common bis-dimedone skeleton are twinned. Unfortunately, neither any of these nor the title compound turned out to be twinned. Whereas the reaction of dimedone with 2,6-dichlorobenzaldehyde leads to four stereoisomers (two enantiomeric pairs of diastereomers) of 3,3,6,6-tetramethyl-4a-hydroxy-9-(2,6-dichlorophenyl)-1,8-dioxo- 2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthene which can all be found in the same crystal (Bolte et al., 2001a), the crystals of the title compound just contain two stereomers. The conformation of the cyclohexane ring can be described as a chair. The other two rings display an approximate sofa conformation with five atoms in a common plane and one atom [C14 0.653 (2) Å; C21 0.592 (2) Å] deviating from this plane. The crystal packing is stabilized by a hydrogen bond between the hydroxyl group and the carbonyl group attached to the cyclohexene ring of an adjacent molecule translated along y. The crystal structure of the title compound agrees well with the structure of Tu et al. (1998) recently determined at room temperature, however, we have also determined the positions of the H atoms, including the hydroxyl group.

Experimental top

The title compound was synthesized according to Cremlyn & Saunders (1993).

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level; Only tertiary and hydroxyl H atoms have been shown.

(rd8) top

Crystal data top

C₂₄H₃₀O₅	F(000) = 1712
M_r = 398.48	D_x = 1.231 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 33.845 (4) Å	Cell parameters from 7436 reflections
b = 7.214 (1) Å	θ = 0–25°
c = 22.605 (3) Å	µ = 0.09 mm⁻¹
β = 128.82 (1)°	T = 173 K
V = 4300.1 (10) Å³	Block, colourless
Z = 8	0.60 × 0.50 × 0.50 mm

Data collection top

Siemens CCD three-circle diffractometer	4750 independent reflections
Radiation source: fine-focus sealed tube	4193 reflections with I > 2σs(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.1°, θ_min = 1.5°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −43→43
T_min = 0.951, T_max = 0.959	k = −9→9
39326 measured reflections	l = −28→28

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0558P)² + 3.6403P] where P = (F_o² + 2F_c²)/3
4750 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₃₀O₅	V = 4300.1 (10) Å³
M_r = 398.48	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.845 (4) Å	µ = 0.09 mm⁻¹
b = 7.214 (1) Å	T = 173 K
c = 22.605 (3) Å	0.60 × 0.50 × 0.50 mm
β = 128.82 (1)°

Data collection top

Siemens CCD three-circle diffractometer	4750 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	4193 reflections with I > 2σs(I)
T_min = 0.951, T_max = 0.959	R_int = 0.024
39326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.34 e Å⁻³
4750 reflections	Δρ_min = −0.23 e Å⁻³
264 parameters

Special details top

Experimental. ;

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	0.12122 (4)	0.66923 (16)	0.04378 (6)	0.0188 (2)
H1	0.1138	0.7884	0.0159	0.023*
C11	0.17833 (4)	0.65689 (16)	0.10174 (6)	0.0200 (2)
C12	0.20475 (4)	0.51162 (17)	0.10450 (6)	0.0201 (2)
O12	0.18343 (3)	0.35659 (12)	0.06152 (5)	0.02137 (19)
C13	0.26153 (4)	0.50279 (18)	0.15320 (7)	0.0246 (3)
H13A	0.2708	0.4369	0.1251	0.030*
H13B	0.2749	0.4301	0.1995	0.030*
C14	0.28656 (5)	0.69446 (19)	0.17659 (7)	0.0263 (3)
C17	0.27656 (6)	0.7943 (2)	0.10856 (9)	0.0406 (4)
H17A	0.2928	0.9164	0.1245	0.061*
H17B	0.2399	0.8095	0.0686	0.061*
H17C	0.2905	0.7210	0.0890	0.061*
C18	0.34396 (5)	0.6714 (2)	0.23959 (9)	0.0366 (3)
H18A	0.3602	0.7936	0.2548	0.055*
H18B	0.3580	0.5959	0.2207	0.055*
H18C	0.3503	0.6100	0.2835	0.055*
C15	0.26359 (5)	0.80402 (19)	0.20666 (8)	0.0281 (3)
H15A	0.2730	0.7429	0.2531	0.034*
H15B	0.2782	0.9304	0.2207	0.034*
C16	0.20637 (4)	0.81829 (17)	0.14927 (7)	0.0212 (2)
O16	0.18464 (3)	0.96186 (12)	0.14399 (5)	0.0268 (2)
C21	0.10176 (4)	0.51451 (16)	−0.01524 (6)	0.0193 (2)
H21	0.0649	0.4953	−0.0414	0.023*
C22	0.12931 (4)	0.32929 (16)	0.02023 (6)	0.0187 (2)
O22	0.12165 (3)	0.27385 (12)	0.07151 (5)	0.02163 (19)
H22	0.1380	0.1760	0.0934	0.026*
C23	0.11263 (5)	0.17950 (17)	−0.03909 (7)	0.0216 (2)
H23A	0.0783	0.1374	−0.0598	0.026*
H23B	0.1358	0.0723	−0.0129	0.026*
C24	0.11117 (5)	0.23308 (18)	−0.10672 (7)	0.0256 (3)
C27	0.16458 (6)	0.2393 (2)	−0.08351 (9)	0.0346 (3)
H27A	0.1850	0.3319	−0.0434	0.052*
H27B	0.1623	0.2727	−0.1276	0.052*
H27C	0.1806	0.1172	−0.0647	0.052*
C28	0.07951 (6)	0.0878 (2)	−0.16954 (8)	0.0363 (3)
H28A	0.0453	0.0831	−0.1847	0.054*
H28B	0.0956	−0.0340	−0.1506	0.054*
H28C	0.0774	0.1216	−0.2135	0.054*
C25	0.08516 (5)	0.42429 (19)	−0.13828 (7)	0.0297 (3)
H25A	0.0895	0.4683	−0.1754	0.036*
H25B	0.0484	0.4115	−0.1651	0.036*
C26	0.10745 (5)	0.56471 (18)	−0.07526 (7)	0.0243 (3)
O26	0.12935 (4)	0.70318 (14)	−0.07108 (6)	0.0354 (2)
C31	0.09319 (4)	0.67912 (16)	0.07631 (7)	0.0200 (2)
C32	0.04118 (4)	0.72515 (17)	0.02731 (7)	0.0223 (2)
O321	0.02079 (3)	0.75913 (13)	−0.04656 (5)	0.0274 (2)
C321	−0.03313 (5)	0.7844 (2)	−0.10058 (8)	0.0314 (3)
H32A	−0.0432	0.7984	−0.1515	0.047*
H32B	−0.0428	0.8958	−0.0875	0.047*
H32C	−0.0502	0.6762	−0.0996	0.047*
C33	0.01372 (5)	0.73613 (18)	0.05401 (8)	0.0274 (3)
H33	−0.0215	0.7629	0.0201	0.033*
C34	0.03847 (5)	0.7076 (2)	0.13078 (8)	0.0304 (3)
H34	0.0200	0.7164	0.1494	0.036*
C35	0.08967 (5)	0.66640 (19)	0.18022 (8)	0.0290 (3)
H35	0.1065	0.6485	0.2327	0.035*
C36	0.11644 (5)	0.65137 (17)	0.15230 (7)	0.0242 (3)
H36	0.1515	0.6213	0.1863	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0164 (5)	0.0183 (5)	0.0206 (5)	0.0020 (4)	0.0110 (5)	0.0019 (4)
C11	0.0173 (5)	0.0219 (6)	0.0210 (5)	0.0005 (4)	0.0122 (5)	0.0015 (4)
C12	0.0186 (5)	0.0227 (6)	0.0195 (5)	−0.0002 (4)	0.0121 (5)	0.0007 (4)
O12	0.0167 (4)	0.0210 (4)	0.0254 (4)	0.0014 (3)	0.0128 (4)	−0.0011 (3)
C13	0.0171 (5)	0.0272 (6)	0.0279 (6)	0.0026 (5)	0.0133 (5)	−0.0009 (5)
C14	0.0180 (6)	0.0301 (7)	0.0296 (6)	−0.0024 (5)	0.0143 (5)	−0.0038 (5)
C17	0.0353 (8)	0.0478 (9)	0.0471 (9)	−0.0042 (7)	0.0299 (7)	0.0063 (7)
C18	0.0181 (6)	0.0434 (8)	0.0398 (8)	−0.0029 (6)	0.0140 (6)	−0.0114 (6)
C15	0.0185 (6)	0.0304 (7)	0.0277 (6)	−0.0010 (5)	0.0108 (5)	−0.0071 (5)
C16	0.0203 (6)	0.0230 (6)	0.0212 (5)	0.0003 (5)	0.0134 (5)	0.0009 (5)
O16	0.0254 (4)	0.0223 (4)	0.0286 (5)	0.0029 (3)	0.0149 (4)	−0.0006 (4)
C21	0.0171 (5)	0.0209 (6)	0.0193 (5)	0.0025 (4)	0.0111 (4)	0.0020 (4)
C22	0.0171 (5)	0.0201 (5)	0.0200 (5)	0.0006 (4)	0.0122 (5)	0.0014 (4)
O22	0.0242 (4)	0.0228 (4)	0.0220 (4)	0.0037 (3)	0.0165 (4)	0.0048 (3)
C23	0.0230 (6)	0.0203 (6)	0.0224 (6)	−0.0008 (4)	0.0147 (5)	−0.0002 (5)
C24	0.0315 (6)	0.0260 (6)	0.0232 (6)	0.0030 (5)	0.0190 (6)	0.0013 (5)
C27	0.0402 (8)	0.0406 (8)	0.0383 (8)	0.0061 (6)	0.0319 (7)	0.0037 (6)
C28	0.0499 (9)	0.0307 (7)	0.0267 (7)	0.0017 (6)	0.0232 (7)	−0.0021 (6)
C25	0.0389 (7)	0.0296 (7)	0.0233 (6)	0.0061 (6)	0.0208 (6)	0.0042 (5)
C26	0.0272 (6)	0.0233 (6)	0.0245 (6)	0.0084 (5)	0.0171 (5)	0.0076 (5)
O26	0.0504 (6)	0.0276 (5)	0.0419 (6)	0.0003 (4)	0.0355 (5)	0.0055 (4)
C31	0.0186 (5)	0.0175 (5)	0.0251 (6)	0.0000 (4)	0.0142 (5)	−0.0019 (4)
C32	0.0196 (6)	0.0204 (6)	0.0245 (6)	−0.0003 (4)	0.0127 (5)	−0.0020 (4)
O321	0.0164 (4)	0.0352 (5)	0.0243 (4)	0.0052 (4)	0.0097 (4)	0.0033 (4)
C321	0.0167 (6)	0.0320 (7)	0.0302 (7)	0.0036 (5)	0.0072 (5)	0.0012 (5)
C33	0.0204 (6)	0.0268 (6)	0.0367 (7)	−0.0003 (5)	0.0187 (6)	−0.0047 (5)
C34	0.0331 (7)	0.0310 (7)	0.0401 (7)	−0.0035 (5)	0.0292 (6)	−0.0068 (6)
C35	0.0345 (7)	0.0307 (7)	0.0274 (6)	−0.0024 (5)	0.0220 (6)	−0.0034 (5)
C36	0.0218 (6)	0.0249 (6)	0.0245 (6)	0.0005 (5)	0.0138 (5)	−0.0001 (5)

Geometric parameters (Å, º) top

C1—C11	1.5118 (15)	C23—C24	1.5474 (17)
C1—C31	1.5233 (16)	C23—H23A	0.9900
C1—C21	1.5356 (16)	C23—H23B	0.9900
C1—H1	1.0000	C24—C28	1.5346 (19)
C11—C12	1.3533 (17)	C24—C27	1.5347 (19)
C11—C16	1.4602 (17)	C24—C25	1.5490 (18)
C12—O12	1.3551 (14)	C27—H27A	0.9800
C12—C13	1.5021 (16)	C27—H27B	0.9800
O12—C22	1.4567 (13)	C27—H27C	0.9800
C13—C14	1.5322 (18)	C28—H28A	0.9800
C13—H13A	0.9900	C28—H28B	0.9800
C13—H13B	0.9900	C28—H28C	0.9800
C14—C17	1.531 (2)	C25—C26	1.5091 (19)
C14—C15	1.5342 (18)	C25—H25A	0.9900
C14—C18	1.5366 (18)	C25—H25B	0.9900
C17—H17A	0.9800	C26—O26	1.2118 (16)
C17—H17B	0.9800	C31—C36	1.3840 (17)
C17—H17C	0.9800	C31—C32	1.4111 (16)
C18—H18A	0.9800	C32—O321	1.3712 (15)
C18—H18B	0.9800	C32—C33	1.3918 (17)
C18—H18C	0.9800	O321—C321	1.4356 (15)
C15—C16	1.5145 (16)	C321—H32A	0.9800
C15—H15A	0.9900	C321—H32B	0.9800
C15—H15B	0.9900	C321—H32C	0.9800
C16—O16	1.2322 (15)	C33—C34	1.390 (2)
C21—C26	1.5284 (16)	C33—H33	0.9500
C21—C22	1.5363 (16)	C34—C35	1.382 (2)
C21—H21	1.0000	C34—H34	0.9500
C22—O22	1.3956 (14)	C35—C36	1.3957 (18)
C22—C23	1.5281 (16)	C35—H35	0.9500
O22—H22	0.8400	C36—H36	0.9500

C11—C1—C31	115.42 (10)	C22—C23—C24	117.11 (10)
C11—C1—C21	109.22 (9)	C22—C23—H23A	108.0
C31—C1—C21	113.31 (9)	C24—C23—H23A	108.0
C11—C1—H1	106.1	C22—C23—H23B	108.0
C31—C1—H1	106.1	C24—C23—H23B	108.0
C21—C1—H1	106.1	H23A—C23—H23B	107.3
C12—C11—C16	118.53 (10)	C28—C24—C27	109.02 (11)
C12—C11—C1	122.30 (11)	C28—C24—C23	108.36 (11)
C16—C11—C1	118.61 (10)	C27—C24—C23	111.60 (11)
C11—C12—O12	124.51 (10)	C28—C24—C25	108.44 (11)
C11—C12—C13	124.84 (11)	C27—C24—C25	109.82 (11)
O12—C12—C13	110.61 (10)	C23—C24—C25	109.53 (10)
C12—O12—C22	117.48 (9)	C24—C27—H27A	109.5
C12—C13—C14	113.03 (10)	C24—C27—H27B	109.5
C12—C13—H13A	109.0	H27A—C27—H27B	109.5
C14—C13—H13A	109.0	C24—C27—H27C	109.5
C12—C13—H13B	109.0	H27A—C27—H27C	109.5
C14—C13—H13B	109.0	H27B—C27—H27C	109.5
H13A—C13—H13B	107.8	C24—C28—H28A	109.5
C17—C14—C13	110.59 (11)	C24—C28—H28B	109.5
C17—C14—C15	110.37 (12)	H28A—C28—H28B	109.5
C13—C14—C15	107.07 (10)	C24—C28—H28C	109.5
C17—C14—C18	109.68 (12)	H28A—C28—H28C	109.5
C13—C14—C18	109.06 (11)	H28B—C28—H28C	109.5
C15—C14—C18	110.03 (11)	C26—C25—C24	111.08 (10)
C14—C17—H17A	109.5	C26—C25—H25A	109.4
C14—C17—H17B	109.5	C24—C25—H25A	109.4
H17A—C17—H17B	109.5	C26—C25—H25B	109.4
C14—C17—H17C	109.5	C24—C25—H25B	109.4
H17A—C17—H17C	109.5	H25A—C25—H25B	108.0
H17B—C17—H17C	109.5	O26—C26—C25	123.11 (12)
C14—C18—H18A	109.5	O26—C26—C21	122.51 (12)
C14—C18—H18B	109.5	C25—C26—C21	114.35 (11)
H18A—C18—H18B	109.5	C36—C31—C32	117.85 (11)
C14—C18—H18C	109.5	C36—C31—C1	123.42 (10)
H18A—C18—H18C	109.5	C32—C31—C1	118.70 (10)
H18B—C18—H18C	109.5	O321—C32—C33	123.70 (11)
C16—C15—C14	112.73 (10)	O321—C32—C31	115.20 (10)
C16—C15—H15A	109.0	C33—C32—C31	121.10 (12)
C14—C15—H15A	109.0	C32—O321—C321	117.35 (10)
C16—C15—H15B	109.0	O321—C321—H32A	109.5
C14—C15—H15B	109.0	O321—C321—H32B	109.5
H15A—C15—H15B	107.8	H32A—C321—H32B	109.5
O16—C16—C11	121.72 (11)	O321—C321—H32C	109.5
O16—C16—C15	120.35 (11)	H32A—C321—H32C	109.5
C11—C16—C15	117.93 (10)	H32B—C321—H32C	109.5
C26—C21—C1	112.02 (10)	C34—C33—C32	119.28 (12)
C26—C21—C22	107.24 (9)	C34—C33—H33	120.4
C1—C21—C22	112.91 (9)	C32—C33—H33	120.4
C26—C21—H21	108.2	C35—C34—C33	120.67 (12)
C1—C21—H21	108.2	C35—C34—H34	119.7
C22—C21—H21	108.2	C33—C34—H34	119.7
O22—C22—O12	108.68 (9)	C34—C35—C36	119.41 (12)
O22—C22—C23	111.56 (9)	C34—C35—H35	120.3
O12—C22—C23	106.39 (9)	C36—C35—H35	120.3
O22—C22—C21	108.35 (9)	C31—C36—C35	121.66 (12)
O12—C22—C21	108.95 (9)	C31—C36—H36	119.2
C23—C22—C21	112.81 (9)	C35—C36—H36	119.2
C22—O22—H22	109.5

C31—C1—C11—C12	119.68 (12)	C26—C21—C22—C23	−51.88 (12)
C21—C1—C11—C12	−9.34 (15)	C1—C21—C22—C23	−175.76 (9)
C31—C1—C11—C16	−69.03 (14)	O22—C22—C23—C24	170.82 (10)
C21—C1—C11—C16	161.95 (10)	O12—C22—C23—C24	−70.80 (12)
C16—C11—C12—O12	−177.59 (10)	C21—C22—C23—C24	48.60 (14)
C1—C11—C12—O12	−6.29 (18)	C22—C23—C24—C28	−163.68 (11)
C16—C11—C12—C13	−0.09 (18)	C22—C23—C24—C27	76.27 (14)
C1—C11—C12—C13	171.21 (11)	C22—C23—C24—C25	−45.56 (15)
C11—C12—O12—C22	−11.87 (16)	C28—C24—C25—C26	167.44 (11)
C13—C12—O12—C22	170.33 (9)	C27—C24—C25—C26	−73.52 (13)
C11—C12—C13—C14	−22.08 (17)	C23—C24—C25—C26	49.37 (14)
O12—C12—C13—C14	155.71 (10)	C24—C25—C26—O26	117.29 (14)
C12—C13—C14—C17	−71.77 (14)	C24—C25—C26—C21	−60.66 (14)
C12—C13—C14—C15	48.52 (14)	C1—C21—C26—O26	6.63 (16)
C12—C13—C14—C18	167.54 (11)	C22—C21—C26—O26	−117.79 (13)
C17—C14—C15—C16	63.51 (15)	C1—C21—C26—C25	−175.40 (10)
C13—C14—C15—C16	−56.92 (14)	C22—C21—C26—C25	60.18 (13)
C18—C14—C15—C16	−175.32 (11)	C11—C1—C31—C36	−9.33 (16)
C12—C11—C16—O16	172.75 (11)	C21—C1—C31—C36	117.66 (12)
C1—C11—C16—O16	1.12 (17)	C11—C1—C31—C32	168.41 (11)
C12—C11—C16—C15	−7.96 (17)	C21—C1—C31—C32	−64.60 (14)
C1—C11—C16—C15	−179.58 (10)	C36—C31—C32—O321	177.19 (11)
C14—C15—C16—O16	−142.63 (12)	C1—C31—C32—O321	−0.68 (16)
C14—C15—C16—C11	38.06 (16)	C36—C31—C32—C33	−2.13 (18)
C11—C1—C21—C26	−80.52 (11)	C1—C31—C32—C33	180.00 (11)
C31—C1—C21—C26	149.30 (10)	C33—C32—O321—C321	−8.05 (18)
C11—C1—C21—C22	40.68 (12)	C31—C32—O321—C321	172.64 (11)
C31—C1—C21—C22	−89.50 (11)	O321—C32—C33—C34	−177.00 (12)
C12—O12—C22—O22	−75.24 (12)	C31—C32—C33—C34	2.27 (19)
C12—O12—C22—C23	164.51 (9)	C32—C33—C34—C35	−0.8 (2)
C12—O12—C22—C21	42.63 (13)	C33—C34—C35—C36	−0.8 (2)
C26—C21—C22—O22	−175.90 (9)	C32—C31—C36—C35	0.54 (18)
C1—C21—C22—O22	60.23 (12)	C1—C31—C36—C35	178.30 (12)
C26—C21—C22—O12	66.03 (11)	C34—C35—C36—C31	0.9 (2)
C1—C21—C22—O12	−57.84 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···O16ⁱ	0.84	1.98	2.814 (1)	171

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀O₅
M_r	398.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	33.845 (4), 7.214 (1), 22.605 (3)
β (°)	128.82 (1)
V (Å³)	4300.1 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.50 × 0.50

Data collection
Diffractometer	Siemens CCD three-circle diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.959
No. of measured, independent and observed [I > 2σs(I)] reflections	39326, 4750, 4193
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.04
No. of reflections	4750
No. of parameters	264
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.23

Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···O16ⁱ	0.84	1.98	2.814 (1)	171

Symmetry code: (i) x, y−1, z.

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Redetermination of 3,3,6,6-tetra­methyl-4a-hydroxy-9-(ortho-methoxy­phenyl)-2,3,4,4a,5,6,7,8,9,9a-deca­hydro-1H-xanthene-1,8-dione at 173 K