ent-Kaur-16-ene-13,19-diol

Salae, A.W.; Chantrapromma, S.; Fun, H.-K.; Ponglimanont, C.

doi:10.1107/S1600536807012834

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ent-Kaur-16-ene-13,19-diol

A. W. Salae, S. Chantrapromma, H.-K. Fun and C. Ponglimanont

The title compound, C₂₀H₃₂O₂, a diterpenoid, was isolated from the roots of Bruguiera cylindrica (Rhizophoraceae). There are two crystallographically independent molecules in the asymmetric unit. In both molecules, the cyclohexane rings adopt chair conformations and the cyclopentane ring has an envelope conformation. In the crystal structure, molecules are linked into a two-dimensional network by intermolecular O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012834/ci2312sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012834/ci2312Isup2.hkl Contains datablock I

CCDC reference: 643639

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.108
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         26

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           29.55
           From the CIF: _reflns_number_total               5031
           Count of symmetry unique reflns         5037
           Completeness (_total/calc)             99.88%
           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 C1A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1B    = .          S
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 C6A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13B   = .          S

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

  13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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: 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).

ent-Kaur-16-ene-13,19-diol top

Crystal data top

C₂₀H₃₂O₂	F(000) = 672
M_r = 304.46	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁	Melting point = 528–530 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.6496 (4) Å	Cell parameters from 4787 reflections
b = 7.8597 (3) Å	θ = 1.0–29.0°
c = 20.3159 (7) Å	µ = 0.08 mm⁻¹
β = 97.907 (2)°	T = 100 K
V = 1684.33 (11) Å³	Needle, colourless
Z = 4	0.56 × 0.24 × 0.12 mm

Data collection top

Bruker SMART APEX II CCD area-detector diffractometer	5031 independent reflections
Radiation source: fine-focus sealed tube	4395 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.6°, θ_min = 1.0°
ω scans	h = −11→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.960, T_max = 0.991	l = −28→24
19242 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0583P)² + 0.1985P] where P = (F_o² + 2F_c²)/3
5031 reflections	(Δ/σ)_max = 0.001
417 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.19 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
O1A	0.64178 (15)	0.1975 (2)	0.27673 (7)	0.0252 (3)
O2A	0.56408 (14)	0.2230 (2)	0.71930 (7)	0.0243 (3)
C1A	0.71855 (18)	0.0051 (3)	0.49586 (9)	0.0188 (4)
C2A	0.7384 (2)	−0.1775 (3)	0.47064 (10)	0.0245 (4)
H2AB	0.8256	−0.2111	0.4846	0.029*
H2AC	0.6843	−0.2550	0.4911	0.029*
C3A	0.7092 (2)	−0.1946 (3)	0.39523 (10)	0.0282 (5)
H3AA	0.7267	−0.3102	0.3825	0.034*
H3AB	0.6198	−0.1724	0.3814	0.034*
C4A	0.7876 (2)	−0.0717 (3)	0.35991 (10)	0.0272 (5)
H4AA	0.7618	−0.0820	0.3124	0.033*
H4AB	0.8759	−0.1053	0.3690	0.033*
C5A	0.77639 (19)	0.1157 (3)	0.37974 (9)	0.0215 (4)
C6A	0.79664 (18)	0.1295 (3)	0.45731 (9)	0.0185 (4)
H6AA	0.8847	0.0936	0.4702	0.022*
C7A	0.7930 (2)	0.3104 (3)	0.48440 (9)	0.0214 (4)
H7AA	0.7058	0.3479	0.4825	0.026*
H7AB	0.8361	0.3872	0.4576	0.026*
C8A	0.85853 (19)	0.3139 (3)	0.55675 (9)	0.0228 (4)
H8AA	0.9468	0.2825	0.5577	0.027*
H8AB	0.8559	0.4289	0.5738	0.027*
C9A	0.79720 (18)	0.1939 (3)	0.60212 (9)	0.0182 (4)
C10A	0.77826 (18)	0.0143 (3)	0.57104 (9)	0.0189 (4)
H10A	0.8644	−0.0299	0.5717	0.023*
C11A	0.7173 (2)	−0.1050 (3)	0.61833 (10)	0.0216 (4)
H11A	0.6794	−0.2005	0.5926	0.026*
H11B	0.7841	−0.1498	0.6510	0.026*
C12A	0.6157 (2)	−0.0244 (3)	0.65542 (10)	0.0224 (4)
H12A	0.5366	−0.0160	0.6255	0.027*
H12B	0.6014	−0.0973	0.6922	0.027*
C13A	0.65476 (18)	0.1520 (3)	0.68184 (9)	0.0199 (4)
C14A	0.67345 (18)	0.2646 (3)	0.62293 (9)	0.0193 (4)
H14A	0.6827	0.3832	0.6360	0.023*
H14B	0.6033	0.2535	0.5873	0.023*
C15A	0.87961 (18)	0.1803 (3)	0.67138 (9)	0.0225 (4)
H15A	0.9406	0.0885	0.6717	0.027*
H15B	0.9251	0.2857	0.6824	0.027*
C16A	0.78785 (19)	0.1451 (3)	0.72028 (10)	0.0205 (4)
C17A	0.57506 (18)	0.0422 (3)	0.48618 (10)	0.0208 (4)
H17A	0.5378	0.0025	0.4432	0.031*
H17B	0.5615	0.1625	0.4893	0.031*
H17C	0.5365	−0.0154	0.5200	0.031*
C18A	0.8833 (2)	0.2151 (4)	0.35268 (10)	0.0286 (5)
H18A	0.8828	0.1887	0.3065	0.043*
H18B	0.9636	0.1835	0.3771	0.043*
H18C	0.8700	0.3350	0.3576	0.043*
C19A	0.65014 (19)	0.1916 (3)	0.34806 (9)	0.0243 (5)
H19A	0.5810	0.1235	0.3603	0.029*
H19B	0.6416	0.3058	0.3650	0.029*
C20A	0.8130 (2)	0.1195 (3)	0.78496 (10)	0.0235 (4)
H20A	0.8964	0.1220	0.8058	0.028*
H20B	0.7474	0.0989	0.8097	0.028*
O1B	0.39586 (16)	0.0197 (3)	0.77040 (8)	0.0302 (4)
O2B	0.42173 (16)	0.0349 (2)	1.22463 (8)	0.0264 (3)
C1B	0.27791 (18)	0.1997 (3)	0.97099 (9)	0.0176 (4)
C2B	0.2448 (2)	0.3767 (3)	0.93981 (11)	0.0235 (4)
H2BB	0.1553	0.3982	0.9403	0.028*
H2BC	0.2918	0.4627	0.9672	0.028*
C3B	0.2741 (2)	0.3949 (3)	0.86863 (11)	0.0277 (5)
H3BA	0.2461	0.5059	0.8516	0.033*
H3BB	0.3650	0.3879	0.8686	0.033*
C4B	0.2091 (2)	0.2576 (3)	0.82328 (10)	0.0264 (5)
H4BA	0.2336	0.2710	0.7793	0.032*
H4BB	0.1181	0.2737	0.8194	0.032*
C5B	0.24126 (19)	0.0758 (3)	0.84777 (10)	0.0205 (4)
C6B	0.21579 (18)	0.0623 (3)	0.92142 (9)	0.0178 (4)
H6BA	0.1248	0.0851	0.9188	0.021*
C7B	0.23072 (19)	−0.1156 (3)	0.95164 (10)	0.0195 (4)
H7BA	0.3198	−0.1397	0.9653	0.023*
H7BB	0.1976	−0.1995	0.9188	0.023*
C8B	0.15885 (19)	−0.1265 (3)	1.01184 (10)	0.0200 (4)
H8BA	0.0692	−0.1093	0.9972	0.024*
H8BB	0.1694	−0.2397	1.0308	0.024*
C9B	0.20387 (18)	0.0039 (3)	1.06539 (9)	0.0174 (4)
C10B	0.21090 (18)	0.1844 (3)	1.03498 (9)	0.0175 (4)
H10B	0.1224	0.2149	1.0200	0.021*
C11B	0.2555 (2)	0.3148 (3)	1.09064 (10)	0.0229 (4)
H11C	0.2888	0.4138	1.0704	0.027*
H11D	0.1821	0.3514	1.1104	0.027*
C12B	0.3564 (2)	0.2517 (3)	1.14638 (10)	0.0234 (4)
H12C	0.4385	0.2529	1.1308	0.028*
H12D	0.3602	0.3288	1.1839	0.028*
C13B	0.3288 (2)	0.0720 (3)	1.16926 (10)	0.0205 (4)
C14B	0.32863 (18)	−0.0466 (3)	1.10936 (9)	0.0181 (4)
H14C	0.3275	−0.1652	1.1225	0.022*
H14D	0.4016	−0.0264	1.0867	0.022*
C15B	0.11238 (19)	0.0094 (3)	1.11891 (9)	0.0230 (4)
H15C	0.0449	0.0909	1.1066	0.028*
H15D	0.0750	−0.1017	1.1237	0.028*
C16B	0.1920 (2)	0.0620 (3)	1.18283 (10)	0.0228 (4)
C17B	0.42266 (18)	0.1852 (3)	0.98662 (10)	0.0219 (4)
H17D	0.4609	0.2301	0.9502	0.033*
H17E	0.4460	0.0679	0.9933	0.033*
H17F	0.4517	0.2486	1.0262	0.033*
C18B	0.1541 (2)	−0.0497 (3)	0.80514 (10)	0.0262 (5)
H18D	0.1470	−0.0164	0.7593	0.039*
H18E	0.0717	−0.0488	0.8192	0.039*
H18F	0.1893	−0.1621	0.8103	0.039*
C19B	0.3788 (2)	0.0310 (3)	0.83892 (10)	0.0263 (5)
H19C	0.4353	0.1173	0.8605	0.032*
H19D	0.4014	−0.0769	0.8605	0.032*
C20B	0.1534 (3)	0.0917 (3)	1.24102 (11)	0.0318 (5)
H20C	0.0680	0.0806	1.2456	0.038*
H20D	0.2116	0.1237	1.2773	0.038*
H1AA	0.581 (3)	0.139 (5)	0.2623 (17)	0.057 (11)*
H2AA	0.510 (3)	0.154 (5)	0.7321 (17)	0.062 (11)*
H1BA	0.376 (3)	−0.083 (5)	0.7555 (15)	0.044 (9)*
H2BA	0.408 (3)	−0.059 (5)	1.2357 (14)	0.037 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0237 (7)	0.0356 (10)	0.0154 (6)	−0.0012 (7)	−0.0002 (6)	0.0002 (7)
O2A	0.0218 (7)	0.0285 (9)	0.0243 (7)	−0.0006 (7)	0.0094 (6)	−0.0061 (7)
C1A	0.0190 (9)	0.0209 (11)	0.0165 (8)	0.0003 (8)	0.0019 (7)	−0.0032 (8)
C2A	0.0281 (11)	0.0237 (11)	0.0219 (10)	0.0012 (9)	0.0039 (8)	−0.0033 (9)
C3A	0.0325 (11)	0.0276 (12)	0.0239 (10)	0.0038 (10)	0.0025 (9)	−0.0106 (9)
C4A	0.0279 (11)	0.0368 (14)	0.0172 (9)	0.0088 (10)	0.0036 (8)	−0.0045 (9)
C5A	0.0179 (9)	0.0331 (12)	0.0132 (8)	0.0040 (9)	0.0011 (7)	0.0002 (8)
C6A	0.0154 (9)	0.0257 (11)	0.0139 (8)	0.0011 (8)	0.0003 (7)	0.0010 (8)
C7A	0.0222 (10)	0.0262 (11)	0.0159 (9)	−0.0029 (9)	0.0028 (7)	0.0011 (8)
C8A	0.0225 (10)	0.0282 (12)	0.0182 (9)	−0.0074 (9)	0.0041 (7)	−0.0010 (9)
C9A	0.0169 (8)	0.0240 (11)	0.0136 (8)	−0.0017 (8)	0.0015 (7)	0.0007 (8)
C10A	0.0185 (9)	0.0228 (11)	0.0158 (8)	0.0012 (8)	0.0034 (7)	0.0006 (8)
C11A	0.0268 (10)	0.0194 (10)	0.0191 (9)	0.0007 (9)	0.0049 (8)	−0.0001 (8)
C12A	0.0240 (10)	0.0253 (11)	0.0186 (9)	−0.0041 (9)	0.0058 (7)	−0.0013 (8)
C13A	0.0179 (9)	0.0260 (11)	0.0167 (8)	−0.0006 (8)	0.0050 (7)	−0.0021 (8)
C14A	0.0208 (9)	0.0202 (10)	0.0171 (8)	−0.0009 (8)	0.0028 (7)	−0.0013 (8)
C15A	0.0191 (9)	0.0314 (12)	0.0165 (8)	−0.0013 (9)	0.0005 (7)	−0.0007 (8)
C16A	0.0224 (9)	0.0206 (10)	0.0182 (9)	−0.0005 (8)	0.0023 (7)	−0.0021 (8)
C17A	0.0180 (9)	0.0262 (11)	0.0183 (8)	−0.0027 (8)	0.0031 (7)	−0.0042 (8)
C18A	0.0223 (10)	0.0464 (15)	0.0177 (9)	0.0025 (10)	0.0045 (8)	0.0032 (10)
C19A	0.0209 (9)	0.0368 (13)	0.0148 (8)	0.0044 (9)	0.0010 (7)	−0.0009 (9)
C20A	0.0250 (10)	0.0267 (12)	0.0189 (9)	0.0026 (9)	0.0033 (8)	0.0010 (8)
O1B	0.0367 (9)	0.0330 (10)	0.0243 (7)	−0.0005 (8)	0.0164 (7)	−0.0006 (7)
O2B	0.0304 (8)	0.0242 (9)	0.0216 (7)	−0.0046 (7)	−0.0070 (6)	0.0028 (7)
C1B	0.0167 (9)	0.0191 (10)	0.0171 (8)	−0.0003 (8)	0.0024 (7)	0.0014 (8)
C2B	0.0267 (10)	0.0199 (11)	0.0234 (10)	0.0029 (9)	0.0012 (8)	0.0035 (8)
C3B	0.0342 (12)	0.0245 (12)	0.0240 (10)	0.0019 (10)	0.0031 (9)	0.0088 (9)
C4B	0.0298 (11)	0.0313 (12)	0.0187 (9)	0.0070 (10)	0.0051 (8)	0.0064 (9)
C5B	0.0207 (9)	0.0253 (11)	0.0157 (8)	0.0045 (8)	0.0036 (7)	0.0024 (8)
C6B	0.0154 (9)	0.0217 (11)	0.0170 (8)	0.0024 (8)	0.0044 (7)	0.0001 (8)
C7B	0.0212 (9)	0.0202 (10)	0.0175 (9)	−0.0006 (8)	0.0042 (7)	−0.0027 (8)
C8B	0.0227 (9)	0.0198 (11)	0.0180 (9)	−0.0057 (8)	0.0044 (7)	−0.0019 (8)
C9B	0.0174 (9)	0.0190 (10)	0.0159 (8)	−0.0019 (8)	0.0031 (7)	−0.0021 (8)
C10B	0.0180 (9)	0.0175 (10)	0.0171 (8)	0.0023 (8)	0.0030 (7)	−0.0010 (7)
C11B	0.0291 (11)	0.0191 (10)	0.0195 (9)	−0.0005 (9)	0.0000 (8)	−0.0023 (8)
C12B	0.0283 (10)	0.0200 (11)	0.0203 (9)	−0.0055 (9)	−0.0021 (8)	−0.0010 (8)
C13B	0.0233 (10)	0.0208 (10)	0.0163 (8)	−0.0016 (8)	−0.0011 (7)	−0.0013 (8)
C14B	0.0181 (9)	0.0175 (10)	0.0182 (9)	−0.0010 (8)	0.0007 (7)	0.0006 (8)
C15B	0.0199 (9)	0.0297 (12)	0.0204 (9)	−0.0016 (9)	0.0066 (7)	−0.0011 (9)
C16B	0.0286 (10)	0.0203 (11)	0.0199 (9)	0.0006 (9)	0.0043 (8)	0.0003 (8)
C17B	0.0181 (9)	0.0234 (11)	0.0242 (9)	−0.0026 (8)	0.0026 (7)	0.0045 (9)
C18B	0.0268 (11)	0.0324 (13)	0.0188 (9)	0.0049 (9)	0.0011 (8)	−0.0020 (9)
C19B	0.0248 (10)	0.0360 (13)	0.0195 (9)	0.0064 (10)	0.0083 (8)	0.0025 (9)
C20B	0.0433 (13)	0.0313 (13)	0.0223 (10)	0.0022 (11)	0.0095 (9)	−0.0041 (9)

Geometric parameters (Å, º) top

O1A—C19A	1.440 (2)	O1B—C19B	1.431 (2)
O1A—H1AA	0.81 (4)	O1B—H1BA	0.88 (4)
O2A—C13A	1.423 (2)	O2B—C13B	1.422 (3)
O2A—H2AA	0.85 (4)	O2B—H2BA	0.79 (3)
C1A—C17A	1.541 (3)	C1B—C17B	1.535 (3)
C1A—C2A	1.548 (3)	C1B—C2B	1.548 (3)
C1A—C6A	1.562 (3)	C1B—C6B	1.561 (3)
C1A—C10A	1.573 (3)	C1B—C10B	1.571 (3)
C2A—C3A	1.527 (3)	C2B—C3B	1.527 (3)
C2A—H2AB	0.97	C2B—H2BB	0.97
C2A—H2AC	0.97	C2B—H2BC	0.97
C3A—C4A	1.519 (3)	C3B—C4B	1.522 (4)
C3A—H3AA	0.97	C3B—H3BA	0.97
C3A—H3AB	0.97	C3B—H3BB	0.97
C4A—C5A	1.536 (4)	C4B—C5B	1.536 (3)
C4A—H4AA	0.97	C4B—H4BA	0.97
C4A—H4AB	0.97	C4B—H4BB	0.97
C5A—C19A	1.530 (3)	C5B—C18B	1.537 (3)
C5A—C18A	1.543 (3)	C5B—C19B	1.541 (3)
C5A—C6A	1.565 (3)	C5B—C6B	1.561 (3)
C6A—C7A	1.527 (3)	C6B—C7B	1.526 (3)
C6A—H6AA	0.98	C6B—H6BA	0.98
C7A—C8A	1.538 (3)	C7B—C8B	1.532 (3)
C7A—H7AA	0.97	C7B—H7BA	0.97
C7A—H7AB	0.97	C7B—H7BB	0.97
C8A—C9A	1.527 (3)	C8B—C9B	1.523 (3)
C8A—H8AA	0.97	C8B—H8BA	0.97
C8A—H8AB	0.97	C8B—H8BB	0.97
C9A—C14A	1.542 (3)	C9B—C14B	1.547 (3)
C9A—C10A	1.548 (3)	C9B—C10B	1.553 (3)
C9A—C15A	1.556 (3)	C9B—C15B	1.557 (3)
C10A—C11A	1.548 (3)	C10B—C11B	1.551 (3)
C10A—H10A	0.98	C10B—H10B	0.98
C11A—C12A	1.538 (3)	C11B—C12B	1.532 (3)
C11A—H11A	0.97	C11B—H11C	0.97
C11A—H11B	0.97	C11B—H11D	0.97
C12A—C13A	1.524 (3)	C12B—C13B	1.528 (3)
C12A—H12A	0.97	C12B—H12C	0.97
C12A—H12B	0.97	C12B—H12D	0.97
C13A—C16A	1.522 (3)	C13B—C16B	1.522 (3)
C13A—C14A	1.523 (3)	C13B—C14B	1.533 (3)
C14A—H14A	0.97	C14B—H14C	0.97
C14A—H14B	0.97	C14B—H14D	0.97
C15A—C16A	1.512 (3)	C15B—C16B	1.508 (3)
C15A—H15A	0.97	C15B—H15C	0.97
C15A—H15B	0.97	C15B—H15D	0.97
C16A—C20A	1.320 (3)	C16B—C20B	1.325 (3)
C17A—H17A	0.96	C17B—H17D	0.96
C17A—H17B	0.96	C17B—H17E	0.96
C17A—H17C	0.96	C17B—H17F	0.96
C18A—H18A	0.96	C18B—H18D	0.96
C18A—H18B	0.96	C18B—H18E	0.96
C18A—H18C	0.96	C18B—H18F	0.96
C19A—H19A	0.97	C19B—H19C	0.97
C19A—H19B	0.97	C19B—H19D	0.97
C20A—H20A	0.93	C20B—H20C	0.93
C20A—H20B	0.93	C20B—H20D	0.93

C19A—O1A—H1AA	106 (2)	C19B—O1B—H1BA	110 (2)
C13A—O2A—H2AA	116 (2)	C13B—O2B—H2BA	107 (2)
C17A—C1A—C2A	108.10 (17)	C17B—C1B—C2B	108.47 (17)
C17A—C1A—C6A	113.87 (17)	C17B—C1B—C6B	114.00 (17)
C2A—C1A—C6A	107.94 (15)	C2B—C1B—C6B	107.78 (16)
C17A—C1A—C10A	112.12 (15)	C17B—C1B—C10B	112.37 (16)
C2A—C1A—C10A	107.96 (17)	C2B—C1B—C10B	107.68 (16)
C6A—C1A—C10A	106.63 (15)	C6B—C1B—C10B	106.28 (15)
C3A—C2A—C1A	113.28 (19)	C3B—C2B—C1B	114.02 (18)
C3A—C2A—H2AB	108.9	C3B—C2B—H2BB	108.7
C1A—C2A—H2AB	108.9	C1B—C2B—H2BB	108.7
C3A—C2A—H2AC	108.9	C3B—C2B—H2BC	108.7
C1A—C2A—H2AC	108.9	C1B—C2B—H2BC	108.7
H2AB—C2A—H2AC	107.7	H2BB—C2B—H2BC	107.6
C4A—C3A—C2A	111.65 (19)	C4B—C3B—C2B	111.82 (19)
C4A—C3A—H3AA	109.3	C4B—C3B—H3BA	109.3
C2A—C3A—H3AA	109.3	C2B—C3B—H3BA	109.3
C4A—C3A—H3AB	109.3	C4B—C3B—H3BB	109.3
C2A—C3A—H3AB	109.3	C2B—C3B—H3BB	109.3
H3AA—C3A—H3AB	108.0	H3BA—C3B—H3BB	107.9
C3A—C4A—C5A	114.71 (17)	C3B—C4B—C5B	113.62 (17)
C3A—C4A—H4AA	108.6	C3B—C4B—H4BA	108.8
C5A—C4A—H4AA	108.6	C5B—C4B—H4BA	108.8
C3A—C4A—H4AB	108.6	C3B—C4B—H4BB	108.8
C5A—C4A—H4AB	108.6	C5B—C4B—H4BB	108.8
H4AA—C4A—H4AB	107.6	H4BA—C4B—H4BB	107.7
C19A—C5A—C4A	111.05 (19)	C4B—C5B—C18B	108.90 (17)
C19A—C5A—C18A	107.55 (18)	C4B—C5B—C19B	110.36 (19)
C4A—C5A—C18A	107.74 (18)	C18B—C5B—C19B	107.29 (18)
C19A—C5A—C6A	112.83 (16)	C4B—C5B—C6B	108.28 (17)
C4A—C5A—C6A	109.01 (18)	C18B—C5B—C6B	108.99 (17)
C18A—C5A—C6A	108.51 (17)	C19B—C5B—C6B	112.94 (16)
C7A—C6A—C1A	111.13 (15)	C7B—C6B—C5B	115.21 (17)
C7A—C6A—C5A	114.88 (17)	C7B—C6B—C1B	111.29 (16)
C1A—C6A—C5A	116.91 (17)	C5B—C6B—C1B	117.21 (17)
C7A—C6A—H6AA	104.0	C7B—C6B—H6BA	103.7
C1A—C6A—H6AA	104.0	C5B—C6B—H6BA	103.7
C5A—C6A—H6AA	104.0	C1B—C6B—H6BA	103.7
C6A—C7A—C8A	109.27 (18)	C6B—C7B—C8B	109.67 (16)
C6A—C7A—H7AA	109.8	C6B—C7B—H7BA	109.7
C8A—C7A—H7AA	109.8	C8B—C7B—H7BA	109.7
C6A—C7A—H7AB	109.8	C6B—C7B—H7BB	109.7
C8A—C7A—H7AB	109.8	C8B—C7B—H7BB	109.7
H7AA—C7A—H7AB	108.3	H7BA—C7B—H7BB	108.2
C9A—C8A—C7A	113.00 (17)	C9B—C8B—C7B	112.94 (16)
C9A—C8A—H8AA	109.0	C9B—C8B—H8BA	109.0
C7A—C8A—H8AA	109.0	C7B—C8B—H8BA	109.0
C9A—C8A—H8AB	109.0	C9B—C8B—H8BB	109.0
C7A—C8A—H8AB	109.0	C7B—C8B—H8BB	109.0
H8AA—C8A—H8AB	107.8	H8BA—C8B—H8BB	107.8
C8A—C9A—C14A	113.29 (18)	C8B—C9B—C14B	113.59 (17)
C8A—C9A—C10A	111.07 (15)	C8B—C9B—C10B	110.99 (15)
C14A—C9A—C10A	111.86 (16)	C14B—C9B—C10B	112.32 (16)
C8A—C9A—C15A	110.69 (16)	C8B—C9B—C15B	110.58 (16)
C14A—C9A—C15A	100.00 (15)	C14B—C9B—C15B	100.02 (15)
C10A—C9A—C15A	109.38 (17)	C10B—C9B—C15B	108.76 (16)
C11A—C10A—C9A	109.97 (15)	C11B—C10B—C9B	109.87 (16)
C11A—C10A—C1A	115.27 (17)	C11B—C10B—C1B	115.08 (17)
C9A—C10A—C1A	116.76 (17)	C9B—C10B—C1B	116.84 (16)
C11A—C10A—H10A	104.4	C11B—C10B—H10B	104.5
C9A—C10A—H10A	104.4	C9B—C10B—H10B	104.5
C1A—C10A—H10A	104.4	C1B—C10B—H10B	104.5
C12A—C11A—C10A	115.99 (18)	C12B—C11B—C10B	116.00 (19)
C12A—C11A—H11A	108.3	C12B—C11B—H11C	108.3
C10A—C11A—H11A	108.3	C10B—C11B—H11C	108.3
C12A—C11A—H11B	108.3	C12B—C11B—H11D	108.3
C10A—C11A—H11B	108.3	C10B—C11B—H11D	108.3
H11A—C11A—H11B	107.4	H11C—C11B—H11D	107.4
C13A—C12A—C11A	111.75 (17)	C13B—C12B—C11B	112.33 (18)
C13A—C12A—H12A	109.3	C13B—C12B—H12C	109.1
C11A—C12A—H12A	109.3	C11B—C12B—H12C	109.1
C13A—C12A—H12B	109.3	C13B—C12B—H12D	109.1
C11A—C12A—H12B	109.3	C11B—C12B—H12D	109.1
H12A—C12A—H12B	107.9	H12C—C12B—H12D	107.9
O2A—C13A—C16A	113.08 (16)	O2B—C13B—C16B	115.17 (17)
O2A—C13A—C14A	111.33 (18)	O2B—C13B—C12B	106.76 (17)
C16A—C13A—C14A	102.17 (16)	C16B—C13B—C12B	109.34 (18)
O2A—C13A—C12A	111.87 (17)	O2B—C13B—C14B	115.36 (18)
C16A—C13A—C12A	109.76 (18)	C16B—C13B—C14B	102.45 (16)
C14A—C13A—C12A	108.12 (16)	C12B—C13B—C14B	107.46 (16)
C13A—C14A—C9A	102.40 (16)	C13B—C14B—C9B	102.09 (16)
C13A—C14A—H14A	111.3	C13B—C14B—H14C	111.4
C9A—C14A—H14A	111.3	C9B—C14B—H14C	111.4
C13A—C14A—H14B	111.3	C13B—C14B—H14D	111.4
C9A—C14A—H14B	111.3	C9B—C14B—H14D	111.4
H14A—C14A—H14B	109.2	H14C—C14B—H14D	109.2
C16A—C15A—C9A	105.76 (16)	C16B—C15B—C9B	106.11 (16)
C16A—C15A—H15A	110.6	C16B—C15B—H15C	110.5
C9A—C15A—H15A	110.6	C9B—C15B—H15C	110.5
C16A—C15A—H15B	110.6	C16B—C15B—H15D	110.5
C9A—C15A—H15B	110.6	C9B—C15B—H15D	110.5
H15A—C15A—H15B	108.7	H15C—C15B—H15D	108.7
C20A—C16A—C15A	128.39 (19)	C20B—C16B—C15B	127.6 (2)
C20A—C16A—C13A	124.30 (18)	C20B—C16B—C13B	125.1 (2)
C15A—C16A—C13A	107.26 (16)	C15B—C16B—C13B	107.28 (16)
C1A—C17A—H17A	109.5	C1B—C17B—H17D	109.5
C1A—C17A—H17B	109.5	C1B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C1A—C17A—H17C	109.5	C1B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
C5A—C18A—H18A	109.5	C5B—C18B—H18D	109.5
C5A—C18A—H18B	109.5	C5B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
C5A—C18A—H18C	109.5	C5B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
O1A—C19A—C5A	111.40 (16)	O1B—C19B—C5B	112.21 (17)
O1A—C19A—H19A	109.3	O1B—C19B—H19C	109.2
C5A—C19A—H19A	109.3	C5B—C19B—H19C	109.2
O1A—C19A—H19B	109.3	O1B—C19B—H19D	109.2
C5A—C19A—H19B	109.3	C5B—C19B—H19D	109.2
H19A—C19A—H19B	108.0	H19C—C19B—H19D	107.9
C16A—C20A—H20A	120.0	C16B—C20B—H20C	120.0
C16A—C20A—H20B	120.0	C16B—C20B—H20D	120.0
H20A—C20A—H20B	120.0	H20C—C20B—H20D	120.0

C17A—C1A—C2A—C3A	70.2 (2)	C17B—C1B—C2B—C3B	72.8 (2)
C6A—C1A—C2A—C3A	−53.4 (2)	C6B—C1B—C2B—C3B	−51.1 (2)
C10A—C1A—C2A—C3A	−168.31 (17)	C10B—C1B—C2B—C3B	−165.33 (18)
C1A—C2A—C3A—C4A	56.6 (3)	C1B—C2B—C3B—C4B	55.4 (2)
C2A—C3A—C4A—C5A	−54.6 (3)	C2B—C3B—C4B—C5B	−55.8 (2)
C3A—C4A—C5A—C19A	−75.5 (2)	C3B—C4B—C5B—C18B	170.59 (18)
C3A—C4A—C5A—C18A	166.94 (18)	C3B—C4B—C5B—C19B	−71.9 (2)
C3A—C4A—C5A—C6A	49.4 (2)	C3B—C4B—C5B—C6B	52.2 (2)
C17A—C1A—C6A—C7A	65.8 (2)	C4B—C5B—C6B—C7B	174.33 (17)
C2A—C1A—C6A—C7A	−174.15 (17)	C18B—C5B—C6B—C7B	56.0 (2)
C10A—C1A—C6A—C7A	−58.4 (2)	C19B—C5B—C6B—C7B	−63.1 (2)
C17A—C1A—C6A—C5A	−68.8 (2)	C4B—C5B—C6B—C1B	−51.8 (2)
C2A—C1A—C6A—C5A	51.3 (2)	C18B—C5B—C6B—C1B	−170.11 (17)
C10A—C1A—C6A—C5A	167.06 (17)	C19B—C5B—C6B—C1B	70.8 (2)
C19A—C5A—C6A—C7A	−58.3 (2)	C17B—C1B—C6B—C7B	66.1 (2)
C4A—C5A—C6A—C7A	177.81 (17)	C2B—C1B—C6B—C7B	−173.44 (16)
C18A—C5A—C6A—C7A	60.7 (2)	C10B—C1B—C6B—C7B	−58.2 (2)
C19A—C5A—C6A—C1A	74.6 (2)	C17B—C1B—C6B—C5B	−69.5 (2)
C4A—C5A—C6A—C1A	−49.3 (2)	C2B—C1B—C6B—C5B	51.0 (2)
C18A—C5A—C6A—C1A	−166.34 (18)	C10B—C1B—C6B—C5B	166.16 (16)
C1A—C6A—C7A—C8A	64.1 (2)	C5B—C6B—C7B—C8B	−159.46 (16)
C5A—C6A—C7A—C8A	−160.33 (16)	C1B—C6B—C7B—C8B	64.0 (2)
C6A—C7A—C8A—C9A	−58.6 (2)	C6B—C7B—C8B—C9B	−58.3 (2)
C7A—C8A—C9A—C14A	−77.8 (2)	C7B—C8B—C9B—C14B	−78.8 (2)
C7A—C8A—C9A—C10A	49.1 (2)	C7B—C8B—C9B—C10B	48.9 (2)
C7A—C8A—C9A—C15A	170.79 (18)	C7B—C8B—C9B—C15B	169.71 (17)
C8A—C9A—C10A—C11A	179.42 (16)	C8B—C9B—C10B—C11B	179.39 (16)
C14A—C9A—C10A—C11A	−52.9 (2)	C14B—C9B—C10B—C11B	−52.2 (2)
C15A—C9A—C10A—C11A	56.9 (2)	C15B—C9B—C10B—C11B	57.5 (2)
C8A—C9A—C10A—C1A	−46.8 (2)	C8B—C9B—C10B—C1B	−47.1 (2)
C14A—C9A—C10A—C1A	80.9 (2)	C14B—C9B—C10B—C1B	81.2 (2)
C15A—C9A—C10A—C1A	−169.28 (15)	C15B—C9B—C10B—C1B	−169.00 (16)
C17A—C1A—C10A—C11A	56.7 (2)	C17B—C1B—C10B—C11B	56.6 (2)
C2A—C1A—C10A—C11A	−62.3 (2)	C2B—C1B—C10B—C11B	−62.8 (2)
C6A—C1A—C10A—C11A	−178.05 (17)	C6B—C1B—C10B—C11B	−178.11 (16)
C17A—C1A—C10A—C9A	−74.7 (2)	C17B—C1B—C10B—C9B	−74.5 (2)
C2A—C1A—C10A—C9A	166.34 (16)	C2B—C1B—C10B—C9B	166.07 (16)
C6A—C1A—C10A—C9A	50.6 (2)	C6B—C1B—C10B—C9B	50.8 (2)
C9A—C10A—C11A—C12A	38.2 (2)	C9B—C10B—C11B—C12B	37.4 (2)
C1A—C10A—C11A—C12A	−96.3 (2)	C1B—C10B—C11B—C12B	−97.0 (2)
C10A—C11A—C12A—C13A	−42.8 (2)	C10B—C11B—C12B—C13B	−43.0 (2)
C11A—C12A—C13A—O2A	−176.78 (17)	C11B—C12B—C13B—O2B	−174.73 (17)
C11A—C12A—C13A—C16A	−50.4 (2)	C11B—C12B—C13B—C16B	−49.5 (2)
C11A—C12A—C13A—C14A	60.3 (2)	C11B—C12B—C13B—C14B	61.0 (2)
O2A—C13A—C14A—C9A	164.88 (16)	O2B—C13B—C14B—C9B	169.23 (17)
C16A—C13A—C14A—C9A	43.90 (19)	C16B—C13B—C14B—C9B	43.30 (19)
C12A—C13A—C14A—C9A	−71.85 (19)	C12B—C13B—C14B—C9B	−71.85 (19)
C8A—C9A—C14A—C13A	−163.74 (16)	C8B—C9B—C14B—C13B	−163.31 (16)
C10A—C9A—C14A—C13A	69.79 (19)	C10B—C9B—C14B—C13B	69.69 (19)
C15A—C9A—C14A—C13A	−45.92 (19)	C15B—C9B—C14B—C13B	−45.50 (19)
C8A—C9A—C15A—C16A	150.37 (19)	C8B—C9B—C15B—C16B	150.98 (18)
C14A—C9A—C15A—C16A	30.6 (2)	C14B—C9B—C15B—C16B	31.0 (2)
C10A—C9A—C15A—C16A	−86.92 (19)	C10B—C9B—C15B—C16B	−86.9 (2)
C9A—C15A—C16A—C20A	178.2 (2)	C9B—C15B—C16B—C20B	176.3 (2)
C9A—C15A—C16A—C13A	−4.4 (2)	C9B—C15B—C16B—C13B	−4.9 (2)
O2A—C13A—C16A—C20A	33.5 (3)	O2B—C13B—C16B—C20B	29.1 (3)
C14A—C13A—C16A—C20A	153.3 (2)	C12B—C13B—C16B—C20B	−91.0 (3)
C12A—C13A—C16A—C20A	−92.2 (3)	C14B—C13B—C16B—C20B	155.2 (2)
O2A—C13A—C16A—C15A	−144.01 (19)	O2B—C13B—C16B—C15B	−149.72 (19)
C14A—C13A—C16A—C15A	−24.2 (2)	C12B—C13B—C16B—C15B	90.1 (2)
C12A—C13A—C16A—C15A	90.3 (2)	C14B—C13B—C16B—C15B	−23.7 (2)
C4A—C5A—C19A—O1A	−65.0 (2)	C4B—C5B—C19B—O1B	−67.2 (2)
C18A—C5A—C19A—O1A	52.7 (2)	C18B—C5B—C19B—O1B	51.3 (3)
C6A—C5A—C19A—O1A	172.30 (19)	C6B—C5B—C19B—O1B	171.42 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AA···O2Bⁱ	0.81 (3)	1.94 (3)	2.750 (2)	171 (4)
O2A—H2AA···O1B	0.86 (4)	1.86 (4)	2.711 (2)	172 (3)
O1B—H1BA···O1Aⁱⁱ	0.88 (4)	1.85 (4)	2.718 (3)	172 (3)
O2B—H2BA···O2Aⁱⁱⁱ	0.79 (4)	1.95 (4)	2.699 (2)	159 (3)

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

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