7-Glycoloyl-2-hydr­oxy-1,4b,7,10a-tetra­methyl-4a,4b,5,6,7,8,8a,9,10,10a-deca­hydro­phenanthren-3(4H)-one

Chantrapromma, S.; Fun, H.-K.; Pakhathirathien, C.; Karalai, C.; Chantrapromma, K.

doi:10.1107/S1600536806054717

7-Glycoloyl-2-hydroxy-1,4b,7,10a-tetramethyl-4a,4b,5,6,7,8,8a,9,10,10a-decahydrophenanthren-3(4H)-one

S. Chantrapromma, H.-K. Fun, C. Pakhathirathien, C. Karalai and K. Chantrapromma

The title compound, C₂₀H₃₀O₄, is a diterpenoid which was isolated from the roots of Ceriops tagal (Perr.). The asymmetric unit consists of three crystallographically independent molecules, which are conformationally almost identical. The molecule has three fused rings in the structure; the cyclohexene ring A adopts a half chair conformation and the two cyclohexane rings B and C are in standard chair conformations. The molecular structure is stabilized by intra- and intermolecular O—H

O hydrogen bonds and weak C—H

O interactions. In the crystal structure, molecules are linked into infinite one-dimensional chains along the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054717/is2118sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054717/is2118Isup2.hkl Contains datablock I

CCDC reference: 638507

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.134
Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.81 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.00 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C16A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C15A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       1.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         33

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           27.50
           From the CIF: _reflns_number_total               6724
           Count of symmetry unique reflns         6769
           Completeness (_total/calc)             99.34%
           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 C5A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5C    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6C    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9C    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10C   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13B   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13C   = .          S

   0 ALERT level A = In general: serious problem
   3 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
   6 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

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

7-Glycoloyl-2-hydroxy-1,4 b,7,10a-tetramethyl-4a,4 b,5,6,7,8,8a,9,10,10a- decahydrophenanthren-3(4H)-one top

Crystal data top

C₂₀H₃₀O₄	D_x = 1.261 Mg m⁻³
M_r = 334.44	Melting point = 425–429 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5787 reflections
a = 7.8316 (4) Å	θ = 1.2–27.5°
b = 21.0250 (9) Å	µ = 0.09 mm⁻¹
c = 32.0885 (13) Å	T = 100 K
V = 5283.7 (4) Å³	Plate, colorless
Z = 12	0.44 × 0.40 × 0.08 mm
F(000) = 2184

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	6724 independent reflections
Radiation source: fine-focus sealed tube	5787 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.2°
ω scans	h = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −27→27
T_min = 0.963, T_max = 0.994	l = −41→41
56698 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.068P)² + 2.2807P] where P = (F_o² + 2F_c²)/3
6724 reflections	(Δ/σ)_max < 0.001
665 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Special details top

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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)
O2A	0.5883 (3)	0.23347 (10)	0.10447 (6)	0.0230 (5)
O1A	0.2430 (3)	0.23853 (10)	0.10598 (6)	0.0209 (4)
H1AA	0.3105	0.2599	0.0923	0.031*
O3A	0.5444 (5)	−0.15983 (13)	0.11823 (8)	0.0538 (9)
O4AA	0.7861 (7)	−0.24725 (19)	0.13027 (14)	0.0336 (15)*	0.641 (14)
H4AA	0.7069	−0.2471	0.1136	0.050*	0.641 (14)
O4AB	0.7093 (16)	−0.2578 (4)	0.1425 (3)	0.048 (3)*	0.359 (14)
H4AB	0.6728	−0.2505	0.1191	0.071*	0.359 (14)
C1A	0.2455 (4)	0.17682 (13)	0.16754 (9)	0.0173 (6)
C2A	0.3296 (4)	0.20656 (13)	0.13677 (8)	0.0166 (6)
C3A	0.5166 (4)	0.20584 (13)	0.13354 (9)	0.0176 (6)
C4A	0.6155 (4)	0.17255 (13)	0.16691 (9)	0.0179 (6)
H4AC	0.6519	0.2039	0.1872	0.021*
H4AD	0.7175	0.1545	0.1545	0.021*
C5A	0.5196 (4)	0.11935 (13)	0.18991 (8)	0.0174 (6)
H5AA	0.5824	0.1125	0.2159	0.021*
C6A	0.3398 (4)	0.14390 (13)	0.20305 (8)	0.0180 (6)
C7A	0.2341 (4)	0.08895 (13)	0.22193 (9)	0.0207 (6)
H7AA	0.2794	0.0789	0.2493	0.025*
H7AB	0.1172	0.1032	0.2256	0.025*
C8A	0.2337 (4)	0.02851 (14)	0.19544 (9)	0.0218 (6)
H8AA	0.1653	−0.0040	0.2088	0.026*
H8AB	0.1848	0.0373	0.1683	0.026*
C9A	0.4161 (4)	0.00551 (13)	0.19060 (9)	0.0201 (6)
H9AA	0.4642	0.0040	0.2188	0.024*
C10A	0.5261 (4)	0.05400 (13)	0.16601 (8)	0.0160 (6)
C11A	0.7120 (4)	0.02927 (14)	0.16707 (9)	0.0220 (6)
H11A	0.7825	0.0570	0.1501	0.026*
H11B	0.7539	0.0317	0.1955	0.026*
C12A	0.7326 (4)	−0.03968 (13)	0.15134 (9)	0.0225 (6)
H12A	0.8505	−0.0527	0.1550	0.027*
H12B	0.7072	−0.0410	0.1218	0.027*
C13A	0.6156 (4)	−0.08743 (14)	0.17417 (8)	0.0209 (6)
C14A	0.4307 (4)	−0.06237 (13)	0.17317 (9)	0.0196 (6)
H14A	0.3896	−0.0628	0.1447	0.024*
H14B	0.3585	−0.0905	0.1894	0.024*
C15A	0.6264 (4)	−0.14977 (14)	0.14954 (9)	0.0224 (6)
C16A	0.7556 (8)	−0.19936 (17)	0.16219 (14)	0.0611 (15)
H16A	0.8616	−0.1785	0.1683	0.073*	0.641 (14)
H16F	0.7175	−0.2200	0.1872	0.073*	0.641 (14)
H16G	0.7568	−0.2043	0.1919	0.073*	0.359 (14)
H16H	0.8675	−0.1866	0.1533	0.073*	0.359 (14)
C17A	0.6752 (5)	−0.09804 (15)	0.21930 (9)	0.0308 (8)
H17A	0.6005	−0.1278	0.2328	0.046*
H17B	0.6730	−0.0583	0.2341	0.046*
H17C	0.7895	−0.1146	0.2192	0.046*
C18A	0.0546 (4)	0.18073 (14)	0.16929 (9)	0.0185 (6)
H18A	0.0149	0.2106	0.1488	0.028*
H18B	0.0199	0.1945	0.1965	0.028*
H18C	0.0067	0.1396	0.1636	0.028*
C19A	0.3599 (4)	0.19442 (14)	0.23793 (9)	0.0220 (6)
H19A	0.2491	0.2088	0.2466	0.033*
H19B	0.4246	0.2298	0.2275	0.033*
H19C	0.4184	0.1759	0.2613	0.033*
C20A	0.4690 (4)	0.05950 (13)	0.12018 (8)	0.0187 (6)
H20A	0.4840	0.0192	0.1065	0.028*
H20B	0.5366	0.0912	0.1063	0.028*
H20C	0.3508	0.0715	0.1191	0.028*
O1B	0.5647 (3)	0.71999 (10)	0.05717 (6)	0.0272 (5)
H1BA	0.4717	0.7315	0.0662	0.033*
O2B	0.2510 (3)	0.69817 (10)	0.03291 (7)	0.0301 (5)
O3B	0.3652 (3)	0.32110 (10)	0.04544 (6)	0.0234 (5)
O4B	0.4949 (5)	0.20840 (10)	0.02083 (7)	0.0465 (8)
H4BA	0.5236	0.2221	0.0437	0.070*
C1B	0.6723 (4)	0.65606 (13)	0.00190 (9)	0.0202 (6)
C2B	0.5408 (4)	0.68273 (14)	0.02244 (9)	0.0213 (6)
C3B	0.3621 (4)	0.67367 (13)	0.01111 (9)	0.0213 (6)
C4B	0.3204 (4)	0.63487 (13)	−0.02675 (9)	0.0220 (6)
H4BB	0.3035	0.6633	−0.0502	0.026*
H4BC	0.2139	0.6125	−0.0220	0.026*
C5B	0.4594 (4)	0.58620 (13)	−0.03803 (8)	0.0170 (6)
H5BA	0.4368	0.5743	−0.0670	0.020*
C6B	0.6386 (4)	0.61906 (13)	−0.03847 (9)	0.0196 (6)
C7B	0.7786 (4)	0.56959 (13)	−0.04731 (9)	0.0211 (6)
H7BA	0.7713	0.5569	−0.0763	0.025*
H7BB	0.8892	0.5894	−0.0432	0.025*
C8B	0.7680 (4)	0.51030 (13)	−0.02015 (9)	0.0202 (6)
H8BA	0.8580	0.4808	−0.0277	0.024*
H8BB	0.7827	0.5218	0.0089	0.024*
C9B	0.5947 (4)	0.47913 (13)	−0.02642 (8)	0.0164 (6)
H9BA	0.5814	0.4734	−0.0566	0.020*
C10B	0.4463 (4)	0.52278 (13)	−0.01249 (8)	0.0165 (6)
C11B	0.2781 (4)	0.48871 (13)	−0.02454 (9)	0.0186 (6)
H11C	0.1825	0.5139	−0.0146	0.022*
H11D	0.2704	0.4866	−0.0547	0.022*
C12B	0.2629 (4)	0.42142 (13)	−0.00683 (9)	0.0191 (6)
H12C	0.1587	0.4021	−0.0172	0.023*
H12D	0.2541	0.4240	0.0233	0.023*
C13B	0.4148 (4)	0.37861 (13)	−0.01824 (8)	0.0171 (6)
C14B	0.5851 (4)	0.41269 (12)	−0.00726 (8)	0.0172 (6)
H14C	0.5953	0.4160	0.0228	0.021*
H14D	0.6800	0.3874	−0.0173	0.021*
C15B	0.4144 (4)	0.31927 (13)	0.00929 (8)	0.0183 (6)
C16B	0.4896 (6)	0.25872 (14)	−0.00806 (9)	0.0315 (8)
H16B	0.4227	0.2455	−0.0320	0.038*
H16C	0.6047	0.2673	−0.0177	0.038*
C17B	0.4119 (4)	0.36082 (13)	−0.06485 (8)	0.0210 (6)
H17D	0.3161	0.3336	−0.0703	0.032*
H17E	0.5157	0.3390	−0.0719	0.032*
H17F	0.4022	0.3988	−0.0813	0.032*
C18B	0.8519 (4)	0.66642 (15)	0.01615 (11)	0.0271 (7)
H18D	0.8526	0.6959	0.0390	0.041*
H18E	0.9183	0.6834	−0.0064	0.041*
H18F	0.9000	0.6267	0.0250	0.041*
C19B	0.6442 (5)	0.66741 (14)	−0.07511 (9)	0.0257 (7)
H19D	0.7576	0.6843	−0.0777	0.039*
H19E	0.5657	0.7015	−0.0697	0.039*
H19F	0.6128	0.6463	−0.1005	0.039*
C20B	0.4456 (4)	0.53355 (13)	0.03508 (8)	0.0185 (6)
H20D	0.4373	0.4933	0.0491	0.028*
H20E	0.3496	0.5596	0.0425	0.028*
H20F	0.5493	0.5544	0.0432	0.028*
O1C	−0.3125 (3)	0.32455 (13)	0.21195 (8)	0.0389 (6)
H1CA	−0.2708	0.3189	0.2351	0.058*
O2C	0.0236 (3)	0.31244 (10)	0.23046 (6)	0.0289 (5)
O3C	0.1746 (4)	0.68446 (12)	0.23222 (7)	0.0421 (7)
O4C	0.1774 (5)	0.80035 (11)	0.19976 (9)	0.0521 (9)
H4CA	0.094 (9)	0.790 (3)	0.2159 (19)	0.11 (2)*
C1C	−0.2366 (4)	0.38024 (15)	0.15071 (10)	0.0249 (7)
C2C	−0.1903 (4)	0.35018 (15)	0.18565 (9)	0.0252 (7)
C3C	−0.0130 (4)	0.34130 (14)	0.19825 (9)	0.0216 (6)
C4C	0.1234 (4)	0.36643 (13)	0.16996 (9)	0.0189 (6)
H4CB	0.1611	0.3323	0.1518	0.023*
H4CC	0.2203	0.3793	0.1868	0.023*
C5C	0.0681 (4)	0.42308 (13)	0.14279 (9)	0.0185 (6)
H5CA	0.1538	0.4263	0.1206	0.022*
C6C	−0.1031 (4)	0.40656 (13)	0.12060 (9)	0.0220 (6)
C7C	−0.1661 (5)	0.46524 (14)	0.09621 (10)	0.0316 (8)
H7CA	−0.0927	0.4713	0.0722	0.038*
H7CB	−0.2804	0.4567	0.0860	0.038*
C8C	−0.1698 (5)	0.52687 (15)	0.12134 (11)	0.0332 (8)
H8CA	−0.2096	0.5616	0.1039	0.040*
H8CB	−0.2476	0.5225	0.1447	0.040*
C9C	0.0083 (5)	0.54100 (13)	0.13704 (9)	0.0234 (7)
H9CA	0.0834	0.5407	0.1126	0.028*
C10C	0.0737 (4)	0.48810 (13)	0.16655 (8)	0.0186 (6)
C11C	0.2618 (4)	0.50503 (14)	0.17610 (9)	0.0216 (6)
H11E	0.3082	0.4733	0.1949	0.026*
H11F	0.3267	0.5031	0.1504	0.026*
C12C	0.2860 (5)	0.57090 (14)	0.19569 (9)	0.0246 (7)
H12E	0.4070	0.5788	0.1994	0.030*
H12F	0.2328	0.5714	0.2230	0.030*
C13C	0.2091 (5)	0.62451 (14)	0.16909 (9)	0.0246 (7)
C14C	0.0236 (5)	0.60755 (14)	0.15661 (9)	0.0266 (7)
H14E	−0.0485	0.6096	0.1812	0.032*
H14F	−0.0178	0.6389	0.1369	0.032*
C15C	0.1956 (5)	0.68507 (15)	0.19522 (9)	0.0254 (7)
C16C	0.2021 (7)	0.74803 (15)	0.17313 (11)	0.0474 (12)
H16D	0.3122	0.7523	0.1595	0.057*
H16E	0.1150	0.7487	0.1517	0.057*
C17C	0.3211 (6)	0.63609 (16)	0.13064 (10)	0.0361 (9)
H17G	0.4283	0.6540	0.1392	0.054*
H17H	0.2643	0.6650	0.1121	0.054*
H17I	0.3409	0.5965	0.1166	0.054*
C18C	−0.4211 (5)	0.38397 (19)	0.13851 (12)	0.0387 (9)
H18G	−0.4878	0.3582	0.1570	0.058*
H18H	−0.4346	0.3688	0.1105	0.058*
H18I	−0.4590	0.4273	0.1402	0.058*
C19C	−0.0716 (5)	0.35364 (14)	0.08779 (9)	0.0245 (7)
H19G	−0.1754	0.3455	0.0728	0.037*
H19H	−0.0351	0.3155	0.1016	0.037*
H19I	0.0153	0.3672	0.0687	0.037*
C20C	−0.0262 (4)	0.48634 (14)	0.20775 (9)	0.0223 (6)
H20I	−0.0119	0.5260	0.2221	0.033*
H20J	0.0160	0.4523	0.2248	0.033*
H20G	−0.1452	0.4796	0.2020	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0187 (11)	0.0238 (10)	0.0267 (11)	−0.0001 (9)	0.0048 (10)	0.0072 (8)
O1A	0.0174 (10)	0.0252 (10)	0.0203 (10)	0.0004 (9)	0.0007 (9)	0.0077 (8)
O3A	0.074 (2)	0.0510 (16)	0.0360 (14)	0.0292 (17)	−0.0239 (15)	−0.0222 (12)
C1A	0.0172 (14)	0.0165 (13)	0.0183 (13)	−0.0001 (12)	−0.0012 (12)	−0.0018 (10)
C2A	0.0168 (14)	0.0165 (12)	0.0166 (12)	0.0032 (12)	−0.0016 (12)	−0.0007 (10)
C3A	0.0169 (14)	0.0151 (12)	0.0207 (13)	0.0002 (12)	0.0007 (12)	−0.0019 (10)
C4A	0.0131 (14)	0.0171 (13)	0.0236 (14)	−0.0005 (12)	0.0008 (12)	−0.0006 (11)
C5A	0.0148 (14)	0.0207 (13)	0.0167 (12)	0.0015 (12)	−0.0018 (12)	−0.0004 (10)
C6A	0.0188 (14)	0.0188 (13)	0.0164 (12)	0.0009 (12)	0.0003 (12)	0.0013 (10)
C7A	0.0228 (16)	0.0196 (13)	0.0197 (13)	−0.0001 (13)	0.0045 (13)	0.0043 (11)
C8A	0.0228 (16)	0.0205 (13)	0.0222 (14)	−0.0016 (13)	0.0042 (13)	0.0030 (11)
C9A	0.0249 (16)	0.0200 (13)	0.0155 (12)	−0.0009 (13)	−0.0001 (13)	0.0030 (10)
C10A	0.0145 (14)	0.0172 (12)	0.0164 (12)	0.0006 (11)	0.0018 (12)	0.0000 (10)
C11A	0.0216 (16)	0.0217 (14)	0.0228 (14)	0.0036 (13)	−0.0017 (13)	−0.0005 (11)
C12A	0.0230 (16)	0.0218 (14)	0.0226 (14)	0.0054 (13)	−0.0010 (13)	−0.0009 (11)
C13A	0.0274 (17)	0.0210 (13)	0.0144 (12)	0.0046 (13)	−0.0036 (13)	0.0003 (11)
C14A	0.0217 (15)	0.0180 (13)	0.0192 (13)	−0.0014 (13)	0.0009 (13)	0.0037 (10)
C15A	0.0229 (16)	0.0227 (14)	0.0216 (14)	0.0007 (13)	0.0014 (13)	0.0013 (11)
C16A	0.101 (4)	0.0268 (18)	0.055 (2)	0.023 (2)	−0.036 (3)	−0.0136 (17)
C17A	0.045 (2)	0.0268 (15)	0.0206 (14)	0.0083 (16)	−0.0070 (16)	−0.0012 (12)
C18A	0.0161 (14)	0.0213 (13)	0.0181 (13)	−0.0017 (12)	0.0024 (12)	0.0018 (11)
C19A	0.0237 (16)	0.0253 (14)	0.0171 (13)	0.0035 (13)	−0.0014 (12)	−0.0020 (11)
C20A	0.0210 (15)	0.0179 (13)	0.0172 (13)	−0.0013 (12)	0.0005 (12)	0.0008 (10)
O1B	0.0311 (13)	0.0264 (11)	0.0240 (10)	−0.0014 (10)	0.0007 (10)	−0.0083 (9)
O2B	0.0271 (13)	0.0256 (11)	0.0376 (12)	0.0049 (11)	0.0041 (11)	−0.0009 (10)
O3B	0.0282 (12)	0.0224 (10)	0.0196 (10)	0.0014 (10)	0.0011 (9)	0.0032 (8)
O4B	0.094 (2)	0.0180 (10)	0.0269 (11)	0.0176 (14)	0.0029 (14)	0.0030 (9)
C1B	0.0231 (16)	0.0143 (12)	0.0231 (14)	−0.0024 (13)	−0.0011 (13)	−0.0001 (11)
C2B	0.0273 (17)	0.0161 (12)	0.0205 (13)	−0.0012 (13)	−0.0014 (13)	0.0004 (11)
C3B	0.0284 (17)	0.0121 (12)	0.0234 (14)	0.0010 (13)	0.0020 (13)	0.0015 (11)
C4B	0.0213 (15)	0.0155 (12)	0.0293 (15)	−0.0007 (13)	−0.0052 (13)	0.0024 (11)
C5B	0.0205 (15)	0.0155 (12)	0.0150 (12)	−0.0001 (12)	−0.0019 (12)	0.0006 (10)
C6B	0.0237 (16)	0.0166 (12)	0.0186 (13)	−0.0007 (13)	0.0013 (13)	0.0012 (11)
C7B	0.0208 (16)	0.0188 (13)	0.0237 (14)	−0.0028 (13)	0.0022 (13)	0.0000 (11)
C8B	0.0219 (16)	0.0177 (13)	0.0209 (14)	−0.0003 (13)	0.0014 (13)	0.0000 (11)
C9B	0.0160 (14)	0.0171 (12)	0.0161 (12)	0.0002 (12)	0.0003 (11)	−0.0002 (10)
C10B	0.0181 (14)	0.0143 (12)	0.0171 (12)	−0.0003 (12)	0.0011 (12)	−0.0004 (10)
C11B	0.0187 (15)	0.0145 (12)	0.0227 (14)	−0.0016 (12)	−0.0042 (12)	0.0012 (10)
C12B	0.0183 (15)	0.0165 (12)	0.0226 (14)	−0.0011 (12)	0.0007 (12)	0.0019 (11)
C13B	0.0196 (15)	0.0148 (12)	0.0171 (12)	0.0001 (12)	−0.0018 (12)	0.0003 (10)
C14B	0.0200 (14)	0.0144 (12)	0.0172 (12)	0.0010 (12)	−0.0011 (12)	−0.0005 (10)
C15B	0.0194 (14)	0.0167 (12)	0.0189 (13)	−0.0014 (12)	−0.0025 (12)	0.0007 (10)
C16B	0.053 (2)	0.0184 (14)	0.0232 (15)	0.0088 (16)	0.0026 (17)	0.0005 (12)
C17B	0.0284 (17)	0.0176 (13)	0.0171 (13)	−0.0024 (13)	−0.0040 (13)	0.0003 (10)
C18B	0.0221 (16)	0.0231 (15)	0.0359 (17)	−0.0031 (14)	−0.0032 (15)	−0.0033 (13)
C19B	0.0356 (19)	0.0183 (13)	0.0233 (14)	−0.0038 (14)	−0.0007 (14)	0.0030 (11)
C20B	0.0228 (15)	0.0161 (12)	0.0165 (12)	0.0008 (12)	0.0014 (12)	0.0024 (10)
O1C	0.0287 (13)	0.0535 (16)	0.0347 (13)	−0.0156 (13)	0.0105 (11)	−0.0120 (12)
O2C	0.0396 (14)	0.0226 (10)	0.0245 (11)	−0.0058 (11)	0.0001 (11)	0.0003 (9)
O3C	0.066 (2)	0.0375 (13)	0.0224 (11)	0.0150 (15)	0.0019 (13)	−0.0066 (10)
O4C	0.085 (2)	0.0215 (12)	0.0493 (16)	−0.0135 (15)	0.0284 (18)	−0.0132 (11)
C1C	0.0187 (16)	0.0258 (15)	0.0301 (16)	0.0031 (13)	−0.0010 (14)	−0.0137 (13)
C2C	0.0238 (16)	0.0281 (15)	0.0237 (15)	−0.0065 (14)	0.0058 (14)	−0.0103 (12)
C3C	0.0280 (17)	0.0179 (13)	0.0190 (13)	−0.0046 (13)	0.0002 (13)	−0.0057 (11)
C4C	0.0170 (14)	0.0195 (13)	0.0202 (13)	0.0016 (12)	−0.0005 (12)	−0.0014 (11)
C5C	0.0188 (15)	0.0198 (13)	0.0168 (12)	0.0026 (13)	0.0002 (12)	−0.0015 (10)
C6C	0.0249 (16)	0.0197 (13)	0.0214 (13)	0.0046 (13)	−0.0060 (13)	−0.0056 (11)
C7C	0.039 (2)	0.0253 (15)	0.0308 (16)	0.0076 (16)	−0.0162 (16)	−0.0083 (13)
C8C	0.041 (2)	0.0220 (15)	0.0364 (18)	0.0101 (16)	−0.0197 (17)	−0.0067 (13)
C9C	0.0319 (18)	0.0190 (13)	0.0191 (13)	0.0022 (14)	−0.0055 (14)	−0.0030 (11)
C10C	0.0233 (15)	0.0167 (12)	0.0159 (12)	0.0042 (13)	−0.0017 (13)	−0.0015 (10)
C11C	0.0240 (16)	0.0198 (13)	0.0209 (14)	−0.0018 (13)	−0.0010 (13)	0.0001 (11)
C12C	0.0279 (17)	0.0254 (14)	0.0204 (14)	−0.0045 (14)	0.0006 (13)	−0.0030 (12)
C13C	0.0372 (19)	0.0197 (14)	0.0168 (13)	−0.0039 (14)	0.0046 (14)	−0.0023 (11)
C14C	0.038 (2)	0.0187 (13)	0.0227 (14)	0.0012 (15)	−0.0067 (15)	−0.0019 (11)
C15C	0.0289 (17)	0.0244 (14)	0.0228 (14)	−0.0040 (14)	0.0025 (14)	−0.0012 (12)
C16C	0.090 (4)	0.0200 (15)	0.0325 (18)	−0.009 (2)	0.021 (2)	−0.0030 (13)
C17C	0.059 (3)	0.0264 (15)	0.0231 (15)	−0.0016 (18)	0.0130 (17)	−0.0009 (12)
C18C	0.0197 (17)	0.044 (2)	0.052 (2)	0.0043 (17)	−0.0064 (17)	−0.0177 (18)
C19C	0.0295 (17)	0.0236 (14)	0.0203 (14)	0.0057 (14)	−0.0034 (14)	−0.0063 (11)
C20C	0.0248 (16)	0.0206 (13)	0.0215 (14)	−0.0002 (13)	0.0007 (13)	−0.0070 (11)

Geometric parameters (Å, º) top

O2A—C3A	1.234 (3)	C9B—C10B	1.546 (4)
O1A—C2A	1.374 (3)	C9B—H9BA	0.9800
O1A—H1AA	0.8200	C10B—C20B	1.543 (4)
O3A—C15A	1.211 (4)	C10B—C11B	1.549 (4)
O4AA—C16A	1.456 (5)	C11B—C12B	1.529 (4)
O4AA—H4AA	0.8200	C11B—H11C	0.9700
O4AB—C16A	1.428 (9)	C11B—H11D	0.9700
O4AB—H4AB	0.8200	C12B—C13B	1.536 (4)
C1A—C2A	1.341 (4)	C12B—H12C	0.9700
C1A—C18A	1.499 (4)	C12B—H12D	0.9700
C1A—C6A	1.524 (4)	C13B—C15B	1.529 (4)
C2A—C3A	1.468 (4)	C13B—C17B	1.542 (4)
C3A—C4A	1.495 (4)	C13B—C14B	1.555 (4)
C4A—C5A	1.536 (4)	C14B—H14C	0.9700
C4A—H4AC	0.9700	C14B—H14D	0.9700
C4A—H4AD	0.9700	C15B—C16B	1.509 (4)
C5A—C6A	1.558 (4)	C16B—H16B	0.9700
C5A—C10A	1.574 (4)	C16B—H16C	0.9700
C5A—H5AA	0.9800	C17B—H17D	0.9600
C6A—C7A	1.545 (4)	C17B—H17E	0.9600
C6A—C19A	1.551 (4)	C17B—H17F	0.9600
C7A—C8A	1.529 (4)	C18B—H18D	0.9600
C7A—H7AA	0.9700	C18B—H18E	0.9600
C7A—H7AB	0.9700	C18B—H18F	0.9600
C8A—C9A	1.516 (4)	C19B—H19D	0.9600
C8A—H8AA	0.9700	C19B—H19E	0.9600
C8A—H8AB	0.9700	C19B—H19F	0.9600
C9A—C14A	1.537 (4)	C20B—H20D	0.9600
C9A—C10A	1.550 (4)	C20B—H20E	0.9600
C9A—H9AA	0.9800	C20B—H20F	0.9600
C10A—C20A	1.541 (4)	O1C—C2C	1.385 (4)
C10A—C11A	1.547 (4)	O1C—H1CA	0.8200
C11A—C12A	1.543 (4)	O2C—C3C	1.232 (4)
C11A—H11A	0.9700	O3C—C15C	1.199 (4)
C11A—H11B	0.9700	O4C—C16C	1.407 (4)
C12A—C13A	1.544 (4)	O4C—H4CA	0.86 (7)
C12A—H12A	0.9700	C1C—C2C	1.337 (5)
C12A—H12B	0.9700	C1C—C18C	1.499 (5)
C13A—C15A	1.533 (4)	C1C—C6C	1.527 (5)
C13A—C17A	1.538 (4)	C2C—C3C	1.459 (5)
C13A—C14A	1.541 (4)	C3C—C4C	1.498 (4)
C14A—H14A	0.9700	C4C—C5C	1.538 (4)
C14A—H14B	0.9700	C4C—H4CB	0.9700
C15A—C16A	1.509 (5)	C4C—H4CC	0.9700
C16A—H16A	0.9600	C5C—C6C	1.558 (4)
C16A—H16F	0.9601	C5C—C10C	1.566 (4)
C16A—H16G	0.9601	C5C—H5CA	0.9800
C16A—H16H	0.9600	C6C—C7C	1.542 (4)
C17A—H17A	0.9600	C6C—C19C	1.552 (4)
C17A—H17B	0.9600	C7C—C8C	1.526 (4)
C17A—H17C	0.9600	C7C—H7CA	0.9700
C18A—H18A	0.9600	C7C—H7CB	0.9700
C18A—H18B	0.9600	C8C—C9C	1.513 (5)
C18A—H18C	0.9600	C8C—H8CA	0.9700
C19A—H19A	0.9600	C8C—H8CB	0.9700
C19A—H19B	0.9600	C9C—C14C	1.538 (4)
C19A—H19C	0.9600	C9C—C10C	1.548 (4)
C20A—H20A	0.9600	C9C—H9CA	0.9800
C20A—H20B	0.9600	C10C—C20C	1.537 (4)
C20A—H20C	0.9600	C10C—C11C	1.546 (4)
O1B—C2B	1.375 (3)	C11C—C12C	1.533 (4)
O1B—H1BA	0.8200	C11C—H11E	0.9700
O2B—C3B	1.230 (4)	C11C—H11F	0.9700
O3B—C15B	1.223 (3)	C12C—C13C	1.537 (4)
O4B—C16B	1.407 (4)	C12C—H12E	0.9700
O4B—H4BA	0.8200	C12C—H12F	0.9700
C1B—C2B	1.345 (4)	C13C—C15C	1.528 (4)
C1B—C18B	1.495 (5)	C13C—C17C	1.533 (5)
C1B—C6B	1.534 (4)	C13C—C14C	1.548 (5)
C2B—C3B	1.458 (5)	C14C—H14E	0.9700
C3B—C4B	1.499 (4)	C14C—H14F	0.9700
C4B—C5B	1.537 (4)	C15C—C16C	1.502 (4)
C4B—H4BB	0.9700	C16C—H16D	0.9700
C4B—H4BC	0.9700	C16C—H16E	0.9700
C5B—C6B	1.565 (4)	C17C—H17G	0.9600
C5B—C10B	1.569 (4)	C17C—H17H	0.9600
C5B—H5BA	0.9800	C17C—H17I	0.9600
C6B—C7B	1.538 (4)	C18C—H18G	0.9600
C6B—C19B	1.555 (4)	C18C—H18H	0.9600
C7B—C8B	1.523 (4)	C18C—H18I	0.9600
C7B—H7BA	0.9700	C19C—H19G	0.9600
C7B—H7BB	0.9700	C19C—H19H	0.9600
C8B—C9B	1.521 (4)	C19C—H19I	0.9600
C8B—H8BA	0.9700	C20C—H20I	0.9600
C8B—H8BB	0.9700	C20C—H20J	0.9600
C9B—C14B	1.528 (4)	C20C—H20G	0.9600

C2A—O1A—H1AA	109.5	C9B—C10B—C11B	107.0 (2)
C16A—O4AA—H4AA	109.5	C20B—C10B—C5B	113.1 (2)
C16A—O4AB—H4AB	109.5	C9B—C10B—C5B	107.7 (2)
C2A—C1A—C18A	119.5 (3)	C11B—C10B—C5B	108.5 (2)
C2A—C1A—C6A	121.6 (3)	C12B—C11B—C10B	113.6 (2)
C18A—C1A—C6A	118.7 (3)	C12B—C11B—H11C	108.8
C1A—C2A—O1A	121.0 (3)	C10B—C11B—H11C	108.8
C1A—C2A—C3A	122.5 (3)	C12B—C11B—H11D	108.8
O1A—C2A—C3A	116.5 (3)	C10B—C11B—H11D	108.8
O2A—C3A—C2A	120.1 (3)	H11C—C11B—H11D	107.7
O2A—C3A—C4A	121.7 (3)	C11B—C12B—C13B	113.2 (2)
C2A—C3A—C4A	118.1 (3)	C11B—C12B—H12C	108.9
C3A—C4A—C5A	115.6 (2)	C13B—C12B—H12C	108.9
C3A—C4A—H4AC	108.4	C11B—C12B—H12D	108.9
C5A—C4A—H4AC	108.4	C13B—C12B—H12D	108.9
C3A—C4A—H4AD	108.4	H12C—C12B—H12D	107.8
C5A—C4A—H4AD	108.4	C15B—C13B—C12B	109.8 (2)
H4AC—C4A—H4AD	107.4	C15B—C13B—C17B	111.3 (2)
C4A—C5A—C6A	109.3 (2)	C12B—C13B—C17B	111.2 (2)
C4A—C5A—C10A	112.7 (2)	C15B—C13B—C14B	104.3 (2)
C6A—C5A—C10A	116.8 (2)	C12B—C13B—C14B	109.9 (2)
C4A—C5A—H5AA	105.7	C17B—C13B—C14B	110.1 (2)
C6A—C5A—H5AA	105.7	C9B—C14B—C13B	111.9 (2)
C10A—C5A—H5AA	105.7	C9B—C14B—H14C	109.2
C1A—C6A—C7A	111.9 (2)	C13B—C14B—H14C	109.2
C1A—C6A—C19A	106.1 (2)	C9B—C14B—H14D	109.2
C7A—C6A—C19A	106.5 (2)	C13B—C14B—H14D	109.2
C1A—C6A—C5A	112.7 (2)	H14C—C14B—H14D	107.9
C7A—C6A—C5A	110.0 (2)	O3B—C15B—C16B	120.0 (2)
C19A—C6A—C5A	109.3 (2)	O3B—C15B—C13B	121.5 (2)
C8A—C7A—C6A	113.8 (2)	C16B—C15B—C13B	118.3 (2)
C8A—C7A—H7AA	108.8	O4B—C16B—C15B	113.8 (2)
C6A—C7A—H7AA	108.8	O4B—C16B—H16B	108.8
C8A—C7A—H7AB	108.8	C15B—C16B—H16B	108.8
C6A—C7A—H7AB	108.8	O4B—C16B—H16C	108.8
H7AA—C7A—H7AB	107.7	C15B—C16B—H16C	108.8
C9A—C8A—C7A	108.7 (3)	H16B—C16B—H16C	107.7
C9A—C8A—H8AA	110.0	C13B—C17B—H17D	109.5
C7A—C8A—H8AA	110.0	C13B—C17B—H17E	109.5
C9A—C8A—H8AB	110.0	H17D—C17B—H17E	109.5
C7A—C8A—H8AB	110.0	C13B—C17B—H17F	109.5
H8AA—C8A—H8AB	108.3	H17D—C17B—H17F	109.5
C8A—C9A—C14A	113.8 (3)	H17E—C17B—H17F	109.5
C8A—C9A—C10A	111.5 (2)	C1B—C18B—H18D	109.5
C14A—C9A—C10A	112.6 (2)	C1B—C18B—H18E	109.5
C8A—C9A—H9AA	106.1	H18D—C18B—H18E	109.5
C14A—C9A—H9AA	106.1	C1B—C18B—H18F	109.5
C10A—C9A—H9AA	106.1	H18D—C18B—H18F	109.5
C20A—C10A—C11A	108.6 (2)	H18E—C18B—H18F	109.5
C20A—C10A—C9A	112.0 (2)	C6B—C19B—H19D	109.5
C11A—C10A—C9A	106.9 (2)	C6B—C19B—H19E	109.5
C20A—C10A—C5A	112.9 (2)	H19D—C19B—H19E	109.5
C11A—C10A—C5A	108.2 (2)	C6B—C19B—H19F	109.5
C9A—C10A—C5A	107.9 (2)	H19D—C19B—H19F	109.5
C12A—C11A—C10A	114.0 (2)	H19E—C19B—H19F	109.5
C12A—C11A—H11A	108.8	C10B—C20B—H20D	109.5
C10A—C11A—H11A	108.8	C10B—C20B—H20E	109.5
C12A—C11A—H11B	108.8	H20D—C20B—H20E	109.5
C10A—C11A—H11B	108.8	C10B—C20B—H20F	109.5
H11A—C11A—H11B	107.6	H20D—C20B—H20F	109.5
C11A—C12A—C13A	113.2 (2)	H20E—C20B—H20F	109.5
C11A—C12A—H12A	108.9	C2C—O1C—H1CA	109.5
C13A—C12A—H12A	108.9	C16C—O4C—H4CA	106 (4)
C11A—C12A—H12B	108.9	C2C—C1C—C18C	120.3 (3)
C13A—C12A—H12B	108.9	C2C—C1C—C6C	121.1 (3)
H12A—C12A—H12B	107.8	C18C—C1C—C6C	118.4 (3)
C15A—C13A—C17A	110.2 (2)	C1C—C2C—O1C	120.5 (3)
C15A—C13A—C14A	109.5 (2)	C1C—C2C—C3C	123.4 (3)
C17A—C13A—C14A	110.8 (3)	O1C—C2C—C3C	116.0 (3)
C15A—C13A—C12A	106.2 (2)	O2C—C3C—C2C	121.1 (3)
C17A—C13A—C12A	111.1 (3)	O2C—C3C—C4C	121.1 (3)
C14A—C13A—C12A	109.0 (2)	C2C—C3C—C4C	117.8 (3)
C9A—C14A—C13A	112.3 (2)	C3C—C4C—C5C	114.6 (3)
C9A—C14A—H14A	109.1	C3C—C4C—H4CB	108.6
C13A—C14A—H14A	109.1	C5C—C4C—H4CB	108.6
C9A—C14A—H14B	109.1	C3C—C4C—H4CC	108.6
C13A—C14A—H14B	109.1	C5C—C4C—H4CC	108.6
H14A—C14A—H14B	107.9	H4CB—C4C—H4CC	107.6
O3A—C15A—C16A	117.3 (3)	C4C—C5C—C6C	109.2 (2)
O3A—C15A—C13A	123.2 (3)	C4C—C5C—C10C	113.1 (2)
C16A—C15A—C13A	119.3 (3)	C6C—C5C—C10C	116.2 (2)
O4AB—C16A—C15A	107.8 (5)	C4C—C5C—H5CA	105.9
O4AA—C16A—C15A	113.5 (3)	C6C—C5C—H5CA	105.9
O4AB—C16A—H16A	134.8	C10C—C5C—H5CA	105.9
O4AA—C16A—H16A	108.6	C1C—C6C—C7C	113.1 (3)
C15A—C16A—H16A	108.6	C1C—C6C—C19C	106.2 (2)
O4AB—C16A—H16F	84.4	C7C—C6C—C19C	106.3 (2)
O4AA—C16A—H16F	109.1	C1C—C6C—C5C	112.4 (2)
C15A—C16A—H16F	109.2	C7C—C6C—C5C	109.2 (3)
H16A—C16A—H16F	107.7	C19C—C6C—C5C	109.4 (3)
O4AB—C16A—H16G	110.4	C8C—C7C—C6C	114.7 (3)
O4AA—C16A—H16G	128.5	C8C—C7C—H7CA	108.6
C15A—C16A—H16G	110.4	C6C—C7C—H7CA	108.6
H16A—C16A—H16G	80.6	C8C—C7C—H7CB	108.6
O4AB—C16A—H16H	110.0	C6C—C7C—H7CB	108.6
O4AA—C16A—H16H	80.5	H7CA—C7C—H7CB	107.6
C15A—C16A—H16H	109.8	C9C—C8C—C7C	109.0 (3)
H16F—C16A—H16H	131.2	C9C—C8C—H8CA	109.9
H16G—C16A—H16H	108.5	C7C—C8C—H8CA	109.9
C13A—C17A—H17A	109.5	C9C—C8C—H8CB	109.9
C13A—C17A—H17B	109.5	C7C—C8C—H8CB	109.9
H17A—C17A—H17B	109.5	H8CA—C8C—H8CB	108.3
C13A—C17A—H17C	109.5	C8C—C9C—C14C	112.7 (3)
H17A—C17A—H17C	109.5	C8C—C9C—C10C	111.6 (3)
H17B—C17A—H17C	109.5	C14C—C9C—C10C	112.2 (2)
C1A—C18A—H18A	109.5	C8C—C9C—H9CA	106.6
C1A—C18A—H18B	109.5	C14C—C9C—H9CA	106.6
H18A—C18A—H18B	109.5	C10C—C9C—H9CA	106.6
C1A—C18A—H18C	109.5	C20C—C10C—C11C	108.7 (2)
H18A—C18A—H18C	109.5	C20C—C10C—C9C	112.0 (2)
H18B—C18A—H18C	109.5	C11C—C10C—C9C	105.7 (2)
C6A—C19A—H19A	109.5	C20C—C10C—C5C	112.6 (2)
C6A—C19A—H19B	109.5	C11C—C10C—C5C	108.9 (2)
H19A—C19A—H19B	109.5	C9C—C10C—C5C	108.7 (2)
C6A—C19A—H19C	109.5	C12C—C11C—C10C	114.0 (3)
H19A—C19A—H19C	109.5	C12C—C11C—H11E	108.7
H19B—C19A—H19C	109.5	C10C—C11C—H11E	108.7
C10A—C20A—H20A	109.5	C12C—C11C—H11F	108.7
C10A—C20A—H20B	109.5	C10C—C11C—H11F	108.7
H20A—C20A—H20B	109.5	H11E—C11C—H11F	107.6
C10A—C20A—H20C	109.5	C11C—C12C—C13C	112.7 (2)
H20A—C20A—H20C	109.5	C11C—C12C—H12E	109.0
H20B—C20A—H20C	109.5	C13C—C12C—H12E	109.0
C2B—O1B—H1BA	109.5	C11C—C12C—H12F	109.0
C16B—O4B—H4BA	109.5	C13C—C12C—H12F	109.0
C2B—C1B—C18B	120.7 (3)	H12E—C12C—H12F	107.8
C2B—C1B—C6B	119.6 (3)	C15C—C13C—C17C	110.4 (2)
C18B—C1B—C6B	119.6 (3)	C15C—C13C—C12C	109.5 (2)
C1B—C2B—O1B	122.0 (3)	C17C—C13C—C12C	109.8 (3)
C1B—C2B—C3B	123.9 (3)	C15C—C13C—C14C	105.6 (3)
O1B—C2B—C3B	114.0 (3)	C17C—C13C—C14C	111.4 (3)
O2B—C3B—C2B	118.8 (3)	C12C—C13C—C14C	110.0 (3)
O2B—C3B—C4B	122.3 (3)	C9C—C14C—C13C	112.8 (3)
C2B—C3B—C4B	118.8 (3)	C9C—C14C—H14E	109.0
C3B—C4B—C5B	113.5 (3)	C13C—C14C—H14E	109.0
C3B—C4B—H4BB	108.9	C9C—C14C—H14F	109.0
C5B—C4B—H4BB	108.9	C13C—C14C—H14F	109.0
C3B—C4B—H4BC	108.9	H14E—C14C—H14F	107.8
C5B—C4B—H4BC	108.9	O3C—C15C—C16C	118.8 (3)
H4BB—C4B—H4BC	107.7	O3C—C15C—C13C	122.9 (3)
C4B—C5B—C6B	110.1 (2)	C16C—C15C—C13C	118.2 (3)
C4B—C5B—C10B	113.4 (2)	O4C—C16C—C15C	113.4 (3)
C6B—C5B—C10B	116.0 (2)	O4C—C16C—H16D	108.9
C4B—C5B—H5BA	105.5	C15C—C16C—H16D	108.9
C6B—C5B—H5BA	105.5	O4C—C16C—H16E	108.9
C10B—C5B—H5BA	105.5	C15C—C16C—H16E	108.9
C1B—C6B—C7B	112.1 (3)	H16D—C16C—H16E	107.7
C1B—C6B—C19B	107.6 (2)	C13C—C17C—H17G	109.5
C7B—C6B—C19B	106.4 (2)	C13C—C17C—H17H	109.5
C1B—C6B—C5B	111.7 (2)	H17G—C17C—H17H	109.5
C7B—C6B—C5B	110.0 (2)	C13C—C17C—H17I	109.5
C19B—C6B—C5B	108.7 (2)	H17G—C17C—H17I	109.5
C8B—C7B—C6B	114.1 (2)	H17H—C17C—H17I	109.5
C8B—C7B—H7BA	108.7	C1C—C18C—H18G	109.5
C6B—C7B—H7BA	108.7	C1C—C18C—H18H	109.5
C8B—C7B—H7BB	108.7	H18G—C18C—H18H	109.5
C6B—C7B—H7BB	108.7	C1C—C18C—H18I	109.5
H7BA—C7B—H7BB	107.6	H18G—C18C—H18I	109.5
C9B—C8B—C7B	109.0 (2)	H18H—C18C—H18I	109.5
C9B—C8B—H8BA	109.9	C6C—C19C—H19G	109.5
C7B—C8B—H8BA	109.9	C6C—C19C—H19H	109.5
C9B—C8B—H8BB	109.9	H19G—C19C—H19H	109.5
C7B—C8B—H8BB	109.9	C6C—C19C—H19I	109.5
H8BA—C8B—H8BB	108.3	H19G—C19C—H19I	109.5
C8B—C9B—C14B	112.6 (2)	H19H—C19C—H19I	109.5
C8B—C9B—C10B	112.1 (2)	C10C—C20C—H20I	109.5
C14B—C9B—C10B	112.9 (2)	C10C—C20C—H20J	109.5
C8B—C9B—H9BA	106.2	H20I—C20C—H20J	109.5
C14B—C9B—H9BA	106.2	C10C—C20C—H20G	109.5
C10B—C9B—H9BA	106.2	H20I—C20C—H20G	109.5
C20B—C10B—C9B	112.1 (2)	H20J—C20C—H20G	109.5
C20B—C10B—C11B	108.1 (2)

C18A—C1A—C2A—O1A	−2.5 (4)	C8B—C9B—C10B—C20B	−67.2 (3)
C6A—C1A—C2A—O1A	−177.0 (2)	C14B—C9B—C10B—C20B	61.3 (3)
C18A—C1A—C2A—C3A	178.8 (3)	C8B—C9B—C10B—C11B	174.4 (2)
C6A—C1A—C2A—C3A	4.3 (4)	C14B—C9B—C10B—C11B	−57.1 (3)
C1A—C2A—C3A—O2A	179.4 (3)	C8B—C9B—C10B—C5B	57.8 (3)
O1A—C2A—C3A—O2A	0.6 (4)	C14B—C9B—C10B—C5B	−173.7 (2)
C1A—C2A—C3A—C4A	−2.3 (4)	C4B—C5B—C10B—C20B	−54.6 (3)
O1A—C2A—C3A—C4A	178.9 (2)	C6B—C5B—C10B—C20B	74.3 (3)
O2A—C3A—C4A—C5A	−156.1 (3)	C4B—C5B—C10B—C9B	−179.0 (2)
C2A—C3A—C4A—C5A	25.6 (4)	C6B—C5B—C10B—C9B	−50.2 (3)
C3A—C4A—C5A—C6A	−47.8 (3)	C4B—C5B—C10B—C11B	65.4 (3)
C3A—C4A—C5A—C10A	83.8 (3)	C6B—C5B—C10B—C11B	−165.7 (2)
C2A—C1A—C6A—C7A	−153.1 (3)	C20B—C10B—C11B—C12B	−65.8 (3)
C18A—C1A—C6A—C7A	32.3 (3)	C9B—C10B—C11B—C12B	55.1 (3)
C2A—C1A—C6A—C19A	91.2 (3)	C5B—C10B—C11B—C12B	171.1 (2)
C18A—C1A—C6A—C19A	−83.4 (3)	C10B—C11B—C12B—C13B	−54.7 (3)
C2A—C1A—C6A—C5A	−28.4 (4)	C11B—C12B—C13B—C15B	165.3 (2)
C18A—C1A—C6A—C5A	157.0 (2)	C11B—C12B—C13B—C17B	−71.1 (3)
C4A—C5A—C6A—C1A	48.2 (3)	C11B—C12B—C13B—C14B	51.1 (3)
C10A—C5A—C6A—C1A	−81.2 (3)	C8B—C9B—C14B—C13B	−173.6 (2)
C4A—C5A—C6A—C7A	173.8 (2)	C10B—C9B—C14B—C13B	58.2 (3)
C10A—C5A—C6A—C7A	44.5 (3)	C15B—C13B—C14B—C9B	−170.4 (2)
C4A—C5A—C6A—C19A	−69.6 (3)	C12B—C13B—C14B—C9B	−52.7 (3)
C10A—C5A—C6A—C19A	161.1 (2)	C17B—C13B—C14B—C9B	70.1 (3)
C1A—C6A—C7A—C8A	77.1 (3)	C12B—C13B—C15B—O3B	−33.8 (4)
C19A—C6A—C7A—C8A	−167.4 (2)	C17B—C13B—C15B—O3B	−157.4 (3)
C5A—C6A—C7A—C8A	−49.1 (3)	C14B—C13B—C15B—O3B	83.9 (3)
C6A—C7A—C8A—C9A	59.8 (3)	C12B—C13B—C15B—C16B	150.9 (3)
C7A—C8A—C9A—C14A	167.0 (2)	C17B—C13B—C15B—C16B	27.3 (4)
C7A—C8A—C9A—C10A	−64.4 (3)	C14B—C13B—C15B—C16B	−91.4 (3)
C8A—C9A—C10A—C20A	−67.1 (3)	O3B—C15B—C16B—O4B	0.0 (5)
C14A—C9A—C10A—C20A	62.2 (3)	C13B—C15B—C16B—O4B	175.4 (3)
C8A—C9A—C10A—C11A	174.1 (2)	C18C—C1C—C2C—O1C	−2.9 (5)
C14A—C9A—C10A—C11A	−56.6 (3)	C6C—C1C—C2C—O1C	−177.7 (3)
C8A—C9A—C10A—C5A	57.8 (3)	C18C—C1C—C2C—C3C	176.2 (3)
C14A—C9A—C10A—C5A	−172.9 (2)	C6C—C1C—C2C—C3C	1.4 (5)
C4A—C5A—C10A—C20A	−52.1 (3)	C1C—C2C—C3C—O2C	−178.9 (3)
C6A—C5A—C10A—C20A	75.6 (3)	O1C—C2C—C3C—O2C	0.2 (4)
C4A—C5A—C10A—C11A	68.2 (3)	C1C—C2C—C3C—C4C	−1.1 (4)
C6A—C5A—C10A—C11A	−164.1 (2)	O1C—C2C—C3C—C4C	178.0 (3)
C4A—C5A—C10A—C9A	−176.4 (2)	O2C—C3C—C4C—C5C	−155.3 (3)
C6A—C5A—C10A—C9A	−48.7 (3)	C2C—C3C—C4C—C5C	26.8 (4)
C20A—C10A—C11A—C12A	−66.8 (3)	C3C—C4C—C5C—C6C	−50.0 (3)
C9A—C10A—C11A—C12A	54.2 (3)	C3C—C4C—C5C—C10C	81.0 (3)
C5A—C10A—C11A—C12A	170.2 (2)	C2C—C1C—C6C—C7C	−150.9 (3)
C10A—C11A—C12A—C13A	−54.3 (3)	C18C—C1C—C6C—C7C	34.2 (4)
C11A—C12A—C13A—C15A	169.4 (2)	C2C—C1C—C6C—C19C	93.0 (3)
C11A—C12A—C13A—C17A	−70.8 (3)	C18C—C1C—C6C—C19C	−81.9 (3)
C11A—C12A—C13A—C14A	51.6 (3)	C2C—C1C—C6C—C5C	−26.6 (4)
C8A—C9A—C14A—C13A	−172.4 (2)	C18C—C1C—C6C—C5C	158.5 (3)
C10A—C9A—C14A—C13A	59.6 (3)	C4C—C5C—C6C—C1C	49.1 (3)
C15A—C13A—C14A—C9A	−170.0 (2)	C10C—C5C—C6C—C1C	−80.2 (3)
C17A—C13A—C14A—C9A	68.3 (3)	C4C—C5C—C6C—C7C	175.4 (2)
C12A—C13A—C14A—C9A	−54.3 (3)	C10C—C5C—C6C—C7C	46.1 (3)
C17A—C13A—C15A—O3A	158.0 (4)	C4C—C5C—C6C—C19C	−68.6 (3)
C14A—C13A—C15A—O3A	36.0 (4)	C10C—C5C—C6C—C19C	162.1 (2)
C12A—C13A—C15A—O3A	−81.5 (4)	C1C—C6C—C7C—C8C	75.9 (4)
C17A—C13A—C15A—C16A	−27.5 (5)	C19C—C6C—C7C—C8C	−168.0 (3)
C14A—C13A—C15A—C16A	−149.6 (3)	C5C—C6C—C7C—C8C	−50.0 (4)
C12A—C13A—C15A—C16A	92.9 (4)	C6C—C7C—C8C—C9C	59.0 (4)
O3A—C15A—C16A—O4AB	−20.8 (8)	C7C—C8C—C9C—C14C	170.6 (3)
C13A—C15A—C16A—O4AB	164.5 (6)	C7C—C8C—C9C—C10C	−62.0 (3)
O3A—C15A—C16A—O4AA	11.0 (6)	C8C—C9C—C10C—C20C	−67.8 (3)
C13A—C15A—C16A—O4AA	−163.8 (4)	C14C—C9C—C10C—C20C	59.8 (4)
C18B—C1B—C2B—O1B	−0.3 (4)	C8C—C9C—C10C—C11C	174.0 (2)
C6B—C1B—C2B—O1B	−175.5 (2)	C14C—C9C—C10C—C11C	−58.4 (3)
C18B—C1B—C2B—C3B	−178.5 (3)	C8C—C9C—C10C—C5C	57.2 (3)
C6B—C1B—C2B—C3B	6.4 (4)	C14C—C9C—C10C—C5C	−175.2 (3)
C1B—C2B—C3B—O2B	177.2 (3)	C4C—C5C—C10C—C20C	−52.8 (3)
O1B—C2B—C3B—O2B	−1.1 (4)	C6C—C5C—C10C—C20C	74.6 (3)
C1B—C2B—C3B—C4B	−2.9 (4)	C4C—C5C—C10C—C11C	67.8 (3)
O1B—C2B—C3B—C4B	178.9 (2)	C6C—C5C—C10C—C11C	−164.8 (2)
O2B—C3B—C4B—C5B	−154.7 (3)	C4C—C5C—C10C—C9C	−177.5 (3)
C2B—C3B—C4B—C5B	25.3 (4)	C6C—C5C—C10C—C9C	−50.1 (3)
C3B—C4B—C5B—C6B	−49.0 (3)	C20C—C10C—C11C—C12C	−62.6 (3)
C3B—C4B—C5B—C10B	82.9 (3)	C9C—C10C—C11C—C12C	57.9 (3)
C2B—C1B—C6B—C7B	−155.4 (3)	C5C—C10C—C11C—C12C	174.5 (2)
C18B—C1B—C6B—C7B	29.4 (4)	C10C—C11C—C12C—C13C	−55.9 (4)
C2B—C1B—C6B—C19B	87.9 (3)	C11C—C12C—C13C—C15C	165.1 (3)
C18B—C1B—C6B—C19B	−87.3 (3)	C11C—C12C—C13C—C17C	−73.5 (4)
C2B—C1B—C6B—C5B	−31.3 (3)	C11C—C12C—C13C—C14C	49.5 (3)
C18B—C1B—C6B—C5B	153.5 (3)	C8C—C9C—C14C—C13C	−174.8 (3)
C4B—C5B—C6B—C1B	51.6 (3)	C10C—C9C—C14C—C13C	58.2 (4)
C10B—C5B—C6B—C1B	−78.8 (3)	C15C—C13C—C14C—C9C	−169.2 (2)
C4B—C5B—C6B—C7B	176.8 (2)	C17C—C13C—C14C—C9C	70.9 (3)
C10B—C5B—C6B—C7B	46.4 (3)	C12C—C13C—C14C—C9C	−51.2 (3)
C4B—C5B—C6B—C19B	−67.0 (3)	C17C—C13C—C15C—O3C	−150.9 (4)
C10B—C5B—C6B—C19B	162.6 (2)	C12C—C13C—C15C—O3C	−29.9 (5)
C1B—C6B—C7B—C8B	75.4 (3)	C14C—C13C—C15C—O3C	88.5 (4)
C19B—C6B—C7B—C8B	−167.2 (2)	C17C—C13C—C15C—C16C	31.5 (5)
C5B—C6B—C7B—C8B	−49.6 (3)	C12C—C13C—C15C—C16C	152.6 (4)
C6B—C7B—C8B—C9B	58.3 (3)	C14C—C13C—C15C—C16C	−89.0 (4)
C7B—C8B—C9B—C14B	168.7 (2)	O3C—C15C—C16C—O4C	−1.6 (6)
C7B—C8B—C9B—C10B	−62.7 (3)	C13C—C15C—C16C—O4C	176.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AA···O2A	0.82	2.28	2.707 (3)	113
O1A—H1AA···O3B	0.82	2.02	2.776 (3)	152
O4AA—H4AA···O1Bⁱ	0.82	2.24	2.997 (5)	155
O4AA—H4AA···O3A	0.82	2.24	2.667 (6)	113
O1B—H1BA···O2B	0.82	2.15	2.618 (3)	116
O4B—H4BA···O2A	0.82	2.03	2.831 (3)	166
O4B—H4BA···O3B	0.82	2.42	2.696 (3)	100
O1C—H1CA···O2C	0.82	2.31	2.710 (3)	110
O1C—H1CA···O4Cⁱⁱ	0.82	2.25	3.067 (4)	175
O4C—H4CA···O3C	0.86 (7)	2.37 (6)	2.650 (4)	100 (5)
O4C—H4CA···O2Cⁱⁱⁱ	0.86 (7)	2.01 (6)	2.749 (4)	143 (6)
C12B—H12D···O3B	0.97	2.44	2.811 (3)	103
C12C—H12F···O3C	0.97	2.45	2.799 (4)	102
C17B—H17D···O2A^iv	0.96	2.52	3.460 (4)	165
C18A—H18A···O1A	0.96	2.33	2.789 (4)	109
C18B—H18D···O1B	0.96	2.38	2.839 (4)	109
C18C—H18G···O1C	0.96	2.34	2.800 (5)	109
C4C—H4CB···O1A	0.97	2.54	3.510 (3)	176

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

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		CIF
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7-Glycoloyl-2-hydr­oxy-1,4b,7,10a-tetra­methyl-4a,4b,5,6,7,8,8a,9,10,10a-deca­hydro­phenanthren-3(4H)-one

Supporting information

Key indicators

checkCIF/PLATON results

7-Glycoloyl-2-hydroxy-1,4b,7,10a-tetramethyl-4a,4b,5,6,7,8,8a,9,10,10a-decahydrophenanthren-3(4H)-one