The absolute configuration of heliespirone B, from sunflower Helianthus annuus

Macías, F.A.; Fronczek, F.R.

doi:10.1107/S160053680701478X

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The absolute configuration of heliespirone B, from sunflower Helianthus annuus

F. A. Macías and F. R. Fronczek

The absolute configuration of the title compound [systematic name: 5-hydroxy-8-(1-hydroxyisopropyl)-3,11-dimethyl-7-oxaspiro[5.5]undec-3-en-2-one], C₁₅H₂₄O₄, has been determined using Cu Kα data at 100 K. The configurations at its four asymmetric C centers are 1R, 2S, 7R and 10S. There are two independent molecules in the asymmetric unit, and they form hydrogen-bonded chains in the [100] direction using only the OH groups.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701478X/fj2010sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680701478X/fj2010Isup2.hkl Contains datablock I

CCDC reference: 647204

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.087
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      66.18 Deg.

Author Response: This was the physical limit of the diffractometer. The structure had already been determined to theta=32.6 deg. (MoK\a). Cu radiation was necessary here for maximum anomalous scattering, and collection of many Friedel pairs was more important than high resolution.


Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .         40 Ang.

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           66.20
           From the CIF: _reflns_number_total               4578
           Count of symmetry unique reflns         2650
           Completeness (_total/calc)            172.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1928
           Fraction of Friedel pairs measured     0.728
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10B   = .          S

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

   9 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: XPREP (Sheldrick, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(1R,2S,7R,10S)-5-hydroxy-8-(1-hydroxyisopropyl)-3,11-dimethyl- 7-oxaspiro[5.5]undec-3-en-2-one top

Crystal data top

C₁₅H₂₄O₄	F(000) = 584
M_r = 268.34	D_x = 1.243 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 13509 reflections
a = 10.3142 (4) Å	θ = 3.7–66.2°
b = 11.9229 (4) Å	µ = 0.72 mm⁻¹
c = 12.2124 (4) Å	T = 100 K
β = 107.223 (2)°	Fragment, colorless
V = 1434.48 (9) Å³	0.38 × 0.35 × 0.32 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4578 independent reflections
Radiation source: fine-focus sealed tube	4573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 66.2°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
T_min = 0.772, T_max = 0.802	k = −14→14
13509 measured reflections	l = −13→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0552P)² + 0.437P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.087	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.37 e Å⁻³
4578 reflections	Δρ_min = −0.17 e Å⁻³
365 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0011 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 2065 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (12)

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
O1A	0.37515 (14)	0.53484 (12)	0.36518 (10)	0.0280 (3)
H1A	0.458 (3)	0.556 (2)	0.400 (2)	0.042*
O2A	0.18743 (13)	0.42089 (12)	−0.07966 (11)	0.0322 (3)
O3A	0.57468 (11)	0.52825 (10)	0.23064 (9)	0.0193 (3)
O4A	0.82814 (13)	0.60106 (11)	0.34936 (10)	0.0229 (3)
H4A	0.904 (3)	0.580 (2)	0.384 (2)	0.034*
C1A	0.42994 (17)	0.53526 (16)	0.17974 (14)	0.0211 (4)
C2A	0.37714 (18)	0.47032 (16)	0.26744 (15)	0.0236 (4)
H2A	0.4423	0.4073	0.2964	0.028*
C3A	0.24010 (18)	0.41802 (15)	0.21931 (16)	0.0243 (4)
H3A	0.1920	0.3994	0.2722	0.029*
C4A	0.17902 (19)	0.39503 (15)	0.10895 (16)	0.0250 (4)
C5A	0.24537 (19)	0.42989 (15)	0.02272 (15)	0.0243 (4)
C6A	0.39038 (18)	0.47051 (16)	0.06518 (14)	0.0228 (4)
H61A	0.4077	0.5196	0.0057	0.027*
H62A	0.4511	0.4047	0.0736	0.027*
C7A	0.38676 (18)	0.65993 (16)	0.16741 (15)	0.0245 (4)
H7A	0.4082	0.6911	0.2468	0.029*
C8A	0.47183 (19)	0.72584 (15)	0.10632 (15)	0.0257 (4)
H81A	0.4478	0.7017	0.0252	0.031*
H82A	0.4504	0.8067	0.1076	0.031*
C9A	0.62338 (19)	0.70849 (15)	0.16231 (15)	0.0258 (4)
H91A	0.6750	0.7464	0.1163	0.031*
H92A	0.6505	0.7422	0.2399	0.031*
C10A	0.65676 (17)	0.58440 (14)	0.17090 (14)	0.0193 (4)
H10A	0.6350	0.5528	0.0916	0.023*
C11A	0.80390 (17)	0.55500 (15)	0.23579 (14)	0.0202 (4)
C12A	0.90242 (18)	0.60775 (17)	0.17930 (15)	0.0265 (4)
H12A	0.8907	0.6894	0.1766	0.040*
H12B	0.8842	0.5786	0.1012	0.040*
H12C	0.9957	0.5892	0.2238	0.040*
C13A	0.82226 (19)	0.42787 (16)	0.24304 (16)	0.0261 (4)
H13A	0.9165	0.4100	0.2855	0.039*
H13B	0.8007	0.3966	0.1655	0.039*
H13C	0.7613	0.3955	0.2828	0.039*
C14A	0.2359 (2)	0.68034 (16)	0.11006 (18)	0.0300 (4)
H14A	0.2118	0.6559	0.0299	0.045*
H14B	0.2161	0.7605	0.1130	0.045*
H14C	0.1827	0.6378	0.1504	0.045*
C15A	0.04603 (19)	0.33593 (17)	0.06709 (17)	0.0296 (4)
H15A	0.0177	0.3103	0.1328	0.044*
H15B	0.0553	0.2712	0.0205	0.044*
H15C	−0.0223	0.3874	0.0205	0.044*
O1B	0.64494 (13)	0.60681 (12)	0.46888 (11)	0.0271 (3)
H1B	0.699 (3)	0.602 (2)	0.425 (2)	0.041*
O2B	0.76635 (14)	0.50804 (12)	0.90985 (11)	0.0339 (3)
O3B	0.94388 (11)	0.55635 (10)	0.59198 (9)	0.0197 (3)
O4B	1.12071 (13)	0.52886 (11)	0.46070 (10)	0.0244 (3)
H4B	1.187 (3)	0.535 (2)	0.437 (2)	0.037*
C1B	0.82902 (17)	0.53099 (15)	0.63331 (14)	0.0218 (4)
C2B	0.72830 (18)	0.62646 (15)	0.58271 (14)	0.0232 (4)
H2B	0.7835	0.6949	0.5804	0.028*
C3B	0.63344 (19)	0.65640 (15)	0.65125 (16)	0.0247 (4)
H3B	0.5573	0.7017	0.6142	0.030*
C4B	0.64592 (19)	0.62555 (15)	0.75885 (16)	0.0257 (4)
C5B	0.76093 (19)	0.55310 (16)	0.81915 (15)	0.0270 (4)
C6B	0.87516 (18)	0.54200 (16)	0.76585 (14)	0.0236 (4)
H61B	0.9299	0.4752	0.7989	0.028*
H62B	0.9348	0.6085	0.7873	0.028*
C7B	0.77627 (18)	0.41350 (16)	0.58971 (14)	0.0234 (4)
H7B	0.7508	0.4166	0.5041	0.028*
C8B	0.89005 (19)	0.32811 (15)	0.62767 (16)	0.0262 (4)
H81B	0.8567	0.2537	0.5953	0.031*
H82B	0.9185	0.3218	0.7123	0.031*
C9B	1.01156 (18)	0.36201 (15)	0.58823 (15)	0.0244 (4)
H91B	1.0873	0.3089	0.6198	0.029*
H92B	0.9866	0.3586	0.5035	0.029*
C10B	1.05672 (17)	0.47962 (15)	0.62812 (14)	0.0201 (3)
H10B	1.0892	0.4795	0.7138	0.024*
C11B	1.16975 (17)	0.52799 (16)	0.58451 (14)	0.0213 (4)
C12B	1.29663 (19)	0.45570 (17)	0.62368 (17)	0.0291 (4)
H12D	1.2780	0.3816	0.5877	0.044*
H12E	1.3231	0.4474	0.7072	0.044*
H12F	1.3705	0.4915	0.6013	0.044*
C13B	1.20162 (19)	0.64798 (16)	0.62810 (16)	0.0276 (4)
H13D	1.2764	0.6775	0.6024	0.041*
H13E	1.2279	0.6484	0.7121	0.041*
H13F	1.1210	0.6950	0.5978	0.041*
C14B	0.6496 (2)	0.37501 (16)	0.61981 (17)	0.0292 (4)
H14D	0.6228	0.3005	0.5872	0.044*
H14E	0.5755	0.4282	0.5882	0.044*
H14F	0.6694	0.3717	0.7033	0.044*
C15B	0.5517 (2)	0.65897 (17)	0.82510 (16)	0.0276 (4)
H15D	0.4856	0.7133	0.7806	0.041*
H15E	0.6036	0.6930	0.8979	0.041*
H15F	0.5038	0.5925	0.8403	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0259 (7)	0.0396 (7)	0.0207 (6)	−0.0057 (6)	0.0102 (5)	−0.0065 (6)
O2A	0.0261 (7)	0.0430 (8)	0.0248 (7)	−0.0010 (6)	0.0036 (5)	−0.0070 (6)
O3A	0.0166 (6)	0.0236 (6)	0.0182 (5)	−0.0013 (5)	0.0059 (5)	0.0001 (5)
O4A	0.0185 (6)	0.0310 (7)	0.0174 (6)	−0.0010 (5)	0.0024 (5)	−0.0005 (5)
C1A	0.0149 (8)	0.0287 (9)	0.0203 (8)	0.0004 (7)	0.0062 (7)	−0.0017 (7)
C2A	0.0228 (9)	0.0263 (8)	0.0227 (8)	0.0000 (7)	0.0081 (7)	−0.0009 (7)
C3A	0.0231 (9)	0.0240 (9)	0.0277 (9)	0.0023 (7)	0.0106 (7)	0.0026 (7)
C4A	0.0216 (9)	0.0218 (8)	0.0311 (9)	0.0036 (7)	0.0072 (8)	−0.0014 (7)
C5A	0.0240 (9)	0.0237 (8)	0.0243 (9)	0.0030 (7)	0.0057 (7)	−0.0041 (7)
C6A	0.0217 (9)	0.0264 (8)	0.0214 (8)	0.0011 (7)	0.0080 (7)	−0.0030 (7)
C7A	0.0250 (10)	0.0290 (9)	0.0201 (8)	0.0028 (8)	0.0077 (7)	−0.0041 (7)
C8A	0.0296 (10)	0.0238 (9)	0.0229 (8)	0.0042 (8)	0.0066 (8)	−0.0002 (7)
C9A	0.0266 (9)	0.0250 (9)	0.0256 (9)	−0.0005 (8)	0.0073 (8)	0.0021 (8)
C10A	0.0194 (8)	0.0242 (8)	0.0155 (8)	−0.0034 (7)	0.0071 (7)	0.0002 (6)
C11A	0.0190 (8)	0.0254 (9)	0.0168 (7)	−0.0009 (7)	0.0060 (7)	−0.0020 (7)
C12A	0.0207 (9)	0.0358 (10)	0.0233 (9)	−0.0045 (8)	0.0069 (7)	−0.0008 (8)
C13A	0.0208 (9)	0.0279 (9)	0.0285 (9)	0.0023 (8)	0.0057 (7)	0.0009 (8)
C14A	0.0266 (10)	0.0286 (10)	0.0350 (10)	0.0064 (8)	0.0094 (8)	0.0022 (8)
C15A	0.0242 (9)	0.0300 (9)	0.0361 (10)	−0.0018 (8)	0.0115 (8)	−0.0059 (8)
O1B	0.0238 (6)	0.0387 (7)	0.0184 (6)	0.0055 (6)	0.0057 (5)	0.0003 (5)
O2B	0.0406 (8)	0.0432 (8)	0.0195 (6)	0.0077 (6)	0.0114 (6)	0.0045 (6)
O3B	0.0168 (6)	0.0230 (6)	0.0200 (6)	0.0028 (5)	0.0066 (5)	0.0025 (5)
O4B	0.0218 (6)	0.0313 (7)	0.0209 (6)	0.0000 (5)	0.0075 (5)	0.0015 (5)
C1B	0.0199 (8)	0.0274 (9)	0.0188 (8)	0.0017 (7)	0.0069 (7)	0.0013 (7)
C2B	0.0238 (9)	0.0258 (9)	0.0204 (8)	0.0017 (7)	0.0070 (7)	0.0006 (7)
C3B	0.0232 (9)	0.0245 (9)	0.0241 (9)	−0.0001 (7)	0.0036 (7)	−0.0024 (7)
C4B	0.0255 (9)	0.0267 (9)	0.0239 (9)	−0.0045 (8)	0.0059 (7)	−0.0050 (7)
C5B	0.0309 (10)	0.0284 (9)	0.0210 (9)	0.0002 (8)	0.0068 (8)	−0.0028 (7)
C6B	0.0248 (9)	0.0259 (8)	0.0190 (8)	0.0040 (7)	0.0049 (7)	0.0006 (7)
C7B	0.0245 (9)	0.0289 (9)	0.0172 (8)	−0.0027 (8)	0.0070 (7)	0.0002 (7)
C8B	0.0320 (10)	0.0227 (9)	0.0253 (9)	−0.0029 (7)	0.0108 (8)	−0.0010 (7)
C9B	0.0257 (9)	0.0234 (9)	0.0257 (9)	0.0025 (7)	0.0100 (8)	0.0008 (7)
C10B	0.0196 (9)	0.0222 (8)	0.0166 (8)	0.0049 (7)	0.0023 (7)	0.0028 (7)
C11B	0.0190 (8)	0.0248 (9)	0.0187 (8)	0.0022 (7)	0.0036 (7)	0.0025 (7)
C12B	0.0215 (9)	0.0354 (11)	0.0311 (10)	0.0033 (8)	0.0087 (8)	0.0057 (8)
C13B	0.0230 (9)	0.0292 (9)	0.0274 (9)	−0.0024 (8)	0.0023 (8)	0.0020 (8)
C14B	0.0295 (10)	0.0297 (10)	0.0298 (10)	−0.0053 (8)	0.0111 (8)	−0.0010 (8)
C15B	0.0306 (10)	0.0303 (9)	0.0228 (9)	−0.0010 (8)	0.0093 (8)	−0.0038 (7)

Geometric parameters (Å, º) top

O1A—C2A	1.425 (2)	O1B—C2B	1.421 (2)
O1A—H1A	0.87 (3)	O1B—H1B	0.89 (3)
O2A—C5A	1.220 (2)	O2B—C5B	1.217 (2)
O3A—C10A	1.4363 (19)	O3B—C10B	1.443 (2)
O3A—C1A	1.440 (2)	O3B—C1B	1.450 (2)
O4A—C11A	1.443 (2)	O4B—C11B	1.445 (2)
O4A—H4A	0.81 (3)	O4B—H4B	0.82 (3)
C1A—C6A	1.543 (2)	C1B—C7B	1.540 (2)
C1A—C2A	1.546 (2)	C1B—C2B	1.542 (2)
C1A—C7A	1.546 (3)	C1B—C6B	1.552 (2)
C2A—C3A	1.497 (3)	C2B—C3B	1.507 (2)
C2A—H2A	1.0000	C2B—H2B	1.0000
C3A—C4A	1.336 (3)	C3B—C4B	1.334 (3)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.475 (3)	C4B—C5B	1.476 (3)
C4A—C15A	1.491 (3)	C4B—C15B	1.491 (3)
C5A—C6A	1.510 (3)	C5B—C6B	1.511 (3)
C6A—H61A	0.9900	C6B—H61B	0.9900
C6A—H62A	0.9900	C6B—H62B	0.9900
C7A—C14A	1.525 (3)	C7B—C8B	1.519 (3)
C7A—C8A	1.527 (3)	C7B—C14B	1.529 (2)
C7A—H7A	1.0000	C7B—H7B	1.0000
C8A—C9A	1.523 (3)	C8B—C9B	1.524 (2)
C8A—H81A	0.9900	C8B—H81B	0.9900
C8A—H82A	0.9900	C8B—H82B	0.9900
C9A—C10A	1.516 (2)	C9B—C10B	1.512 (2)
C9A—H91A	0.9900	C9B—H91B	0.9900
C9A—H92A	0.9900	C9B—H92B	0.9900
C10A—C11A	1.530 (2)	C10B—C11B	1.531 (2)
C10A—H10A	1.0000	C10B—H10B	1.0000
C11A—C12A	1.523 (2)	C11B—C12B	1.521 (3)
C11A—C13A	1.527 (3)	C11B—C13B	1.528 (3)
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
C13A—H13A	0.9800	C13B—H13D	0.9800
C13A—H13B	0.9800	C13B—H13E	0.9800
C13A—H13C	0.9800	C13B—H13F	0.9800
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800

C2A—O1A—H1A	107.6 (16)	C2B—O1B—H1B	107.3 (16)
C10A—O3A—C1A	116.45 (12)	C10B—O3B—C1B	115.43 (12)
C11A—O4A—H4A	104.8 (17)	C11B—O4B—H4B	107.0 (16)
O3A—C1A—C6A	108.93 (13)	O3B—C1B—C7B	108.10 (13)
O3A—C1A—C2A	101.82 (13)	O3B—C1B—C2B	103.27 (13)
C6A—C1A—C2A	108.95 (14)	C7B—C1B—C2B	113.95 (14)
O3A—C1A—C7A	109.26 (14)	O3B—C1B—C6B	108.40 (13)
C6A—C1A—C7A	113.66 (14)	C7B—C1B—C6B	113.92 (14)
C2A—C1A—C7A	113.49 (14)	C2B—C1B—C6B	108.53 (14)
O1A—C2A—C3A	107.92 (14)	O1B—C2B—C3B	106.16 (14)
O1A—C2A—C1A	113.91 (15)	O1B—C2B—C1B	114.28 (14)
C3A—C2A—C1A	114.97 (14)	C3B—C2B—C1B	115.07 (14)
O1A—C2A—H2A	106.5	O1B—C2B—H2B	106.9
C3A—C2A—H2A	106.5	C3B—C2B—H2B	106.9
C1A—C2A—H2A	106.5	C1B—C2B—H2B	106.9
C4A—C3A—C2A	126.15 (16)	C4B—C3B—C2B	126.37 (17)
C4A—C3A—H3A	116.9	C4B—C3B—H3B	116.8
C2A—C3A—H3A	116.9	C2B—C3B—H3B	116.8
C3A—C4A—C5A	118.84 (17)	C3B—C4B—C5B	118.81 (17)
C3A—C4A—C15A	123.63 (17)	C3B—C4B—C15B	124.93 (17)
C5A—C4A—C15A	117.54 (16)	C5B—C4B—C15B	116.26 (16)
O2A—C5A—C4A	121.11 (17)	O2B—C5B—C4B	121.72 (17)
O2A—C5A—C6A	120.97 (16)	O2B—C5B—C6B	121.44 (17)
C4A—C5A—C6A	117.82 (15)	C4B—C5B—C6B	116.77 (15)
C5A—C6A—C1A	116.15 (14)	C5B—C6B—C1B	114.79 (14)
C5A—C6A—H61A	108.2	C5B—C6B—H61B	108.6
C1A—C6A—H61A	108.2	C1B—C6B—H61B	108.6
C5A—C6A—H62A	108.2	C5B—C6B—H62B	108.6
C1A—C6A—H62A	108.2	C1B—C6B—H62B	108.6
H61A—C6A—H62A	107.4	H61B—C6B—H62B	107.5
C14A—C7A—C8A	110.45 (15)	C8B—C7B—C14B	111.31 (15)
C14A—C7A—C1A	115.05 (15)	C8B—C7B—C1B	110.02 (14)
C8A—C7A—C1A	110.59 (14)	C14B—C7B—C1B	115.45 (14)
C14A—C7A—H7A	106.8	C8B—C7B—H7B	106.5
C8A—C7A—H7A	106.8	C14B—C7B—H7B	106.5
C1A—C7A—H7A	106.8	C1B—C7B—H7B	106.5
C9A—C8A—C7A	111.87 (15)	C7B—C8B—C9B	111.04 (15)
C9A—C8A—H81A	109.2	C7B—C8B—H81B	109.4
C7A—C8A—H81A	109.2	C9B—C8B—H81B	109.4
C9A—C8A—H82A	109.2	C7B—C8B—H82B	109.4
C7A—C8A—H82A	109.2	C9B—C8B—H82B	109.4
H81A—C8A—H82A	107.9	H81B—C8B—H82B	108.0
C10A—C9A—C8A	110.21 (15)	C10B—C9B—C8B	110.36 (15)
C10A—C9A—H91A	109.6	C10B—C9B—H91B	109.6
C8A—C9A—H91A	109.6	C8B—C9B—H91B	109.6
C10A—C9A—H92A	109.6	C10B—C9B—H92B	109.6
C8A—C9A—H92A	109.6	C8B—C9B—H92B	109.6
H91A—C9A—H92A	108.1	H91B—C9B—H92B	108.1
O3A—C10A—C9A	109.52 (13)	O3B—C10B—C9B	110.23 (13)
O3A—C10A—C11A	105.87 (13)	O3B—C10B—C11B	106.45 (13)
C9A—C10A—C11A	115.44 (14)	C9B—C10B—C11B	115.54 (14)
O3A—C10A—H10A	108.6	O3B—C10B—H10B	108.1
C9A—C10A—H10A	108.6	C9B—C10B—H10B	108.1
C11A—C10A—H10A	108.6	C11B—C10B—H10B	108.1
O4A—C11A—C12A	109.22 (14)	O4B—C11B—C12B	109.58 (14)
O4A—C11A—C13A	109.80 (14)	O4B—C11B—C13B	109.29 (14)
C12A—C11A—C13A	110.39 (15)	C12B—C11B—C13B	110.17 (15)
O4A—C11A—C10A	105.88 (13)	O4B—C11B—C10B	107.46 (13)
C12A—C11A—C10A	111.30 (14)	C12B—C11B—C10B	110.49 (14)
C13A—C11A—C10A	110.14 (14)	C13B—C11B—C10B	109.81 (14)
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C7A—C14A—H14A	109.5	C7B—C14B—H14D	109.5
C7A—C14A—H14B	109.5	C7B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C7A—C14A—H14C	109.5	C7B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C4A—C15A—H15A	109.5	C4B—C15B—H15D	109.5
C4A—C15A—H15B	109.5	C4B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C4A—C15A—H15C	109.5	C4B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5

C10A—O3A—C1A—C6A	66.74 (18)	C10B—O3B—C1B—C7B	−59.63 (16)
C10A—O3A—C1A—C2A	−178.27 (12)	C10B—O3B—C1B—C2B	179.31 (13)
C10A—O3A—C1A—C7A	−57.96 (16)	C10B—O3B—C1B—C6B	64.31 (18)
O3A—C1A—C2A—O1A	80.80 (17)	O3B—C1B—C2B—O1B	84.79 (17)
C6A—C1A—C2A—O1A	−164.22 (14)	C7B—C1B—C2B—O1B	−32.2 (2)
C7A—C1A—C2A—O1A	−36.5 (2)	C6B—C1B—C2B—O1B	−160.31 (14)
O3A—C1A—C2A—C3A	−153.91 (15)	O3B—C1B—C2B—C3B	−151.98 (14)
C6A—C1A—C2A—C3A	−38.9 (2)	C7B—C1B—C2B—C3B	91.01 (18)
C7A—C1A—C2A—C3A	88.81 (18)	C6B—C1B—C2B—C3B	−37.1 (2)
O1A—C2A—C3A—C4A	148.41 (18)	O1B—C2B—C3B—C4B	141.76 (19)
C1A—C2A—C3A—C4A	20.1 (3)	C1B—C2B—C3B—C4B	14.3 (3)
C2A—C3A—C4A—C5A	−4.4 (3)	C2B—C3B—C4B—C5B	−1.3 (3)
C2A—C3A—C4A—C15A	175.84 (18)	C2B—C3B—C4B—C15B	178.51 (17)
C3A—C4A—C5A—O2A	−172.57 (17)	C3B—C4B—C5B—O2B	−168.34 (18)
C15A—C4A—C5A—O2A	7.2 (3)	C15B—C4B—C5B—O2B	11.8 (3)
C3A—C4A—C5A—C6A	11.0 (2)	C3B—C4B—C5B—C6B	14.6 (3)
C15A—C4A—C5A—C6A	−169.16 (16)	C15B—C4B—C5B—C6B	−165.29 (16)
O2A—C5A—C6A—C1A	149.58 (17)	O2B—C5B—C6B—C1B	142.01 (18)
C4A—C5A—C6A—C1A	−34.0 (2)	C4B—C5B—C6B—C1B	−40.9 (2)
O3A—C1A—C6A—C5A	156.99 (14)	O3B—C1B—C6B—C5B	162.29 (14)
C2A—C1A—C6A—C5A	46.7 (2)	C7B—C1B—C6B—C5B	−77.32 (19)
C7A—C1A—C6A—C5A	−80.94 (19)	C2B—C1B—C6B—C5B	50.8 (2)
O3A—C1A—C7A—C14A	177.70 (14)	O3B—C1B—C7B—C8B	56.16 (17)
C6A—C1A—C7A—C14A	55.8 (2)	C2B—C1B—C7B—C8B	170.33 (14)
C2A—C1A—C7A—C14A	−69.44 (19)	C6B—C1B—C7B—C8B	−64.40 (18)
O3A—C1A—C7A—C8A	51.71 (18)	O3B—C1B—C7B—C14B	−176.85 (14)
C6A—C1A—C7A—C8A	−70.18 (18)	C2B—C1B—C7B—C14B	−62.67 (19)
C2A—C1A—C7A—C8A	164.57 (14)	C6B—C1B—C7B—C14B	62.6 (2)
C14A—C7A—C8A—C9A	179.31 (15)	C14B—C7B—C8B—C9B	175.04 (15)
C1A—C7A—C8A—C9A	−52.16 (19)	C1B—C7B—C8B—C9B	−55.68 (18)
C7A—C8A—C9A—C10A	53.89 (19)	C7B—C8B—C9B—C10B	54.21 (19)
C1A—O3A—C10A—C9A	60.10 (17)	C1B—O3B—C10B—C9B	59.11 (17)
C1A—O3A—C10A—C11A	−174.82 (13)	C1B—O3B—C10B—C11B	−174.89 (13)
C8A—C9A—C10A—O3A	−55.19 (18)	C8B—C9B—C10B—O3B	−53.79 (18)
C8A—C9A—C10A—C11A	−174.53 (13)	C8B—C9B—C10B—C11B	−174.49 (14)
O3A—C10A—C11A—O4A	−62.64 (16)	O3B—C10B—C11B—O4B	−63.36 (16)
C9A—C10A—C11A—O4A	58.69 (18)	C9B—C10B—C11B—O4B	59.36 (18)
O3A—C10A—C11A—C12A	178.79 (13)	O3B—C10B—C11B—C12B	177.13 (13)
C9A—C10A—C11A—C12A	−59.88 (19)	C9B—C10B—C11B—C12B	−60.14 (19)
O3A—C10A—C11A—C13A	56.02 (17)	O3B—C10B—C11B—C13B	55.41 (16)
C9A—C10A—C11A—C13A	177.35 (15)	C9B—C10B—C11B—C13B	178.13 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1B	0.87 (3)	1.96 (3)	2.8278 (19)	177 (2)
O4A—H4A···O4B	0.81 (3)	2.24 (3)	3.0440 (19)	173 (2)
O1B—H1B···O4A	0.89 (3)	1.83 (3)	2.7091 (18)	172 (2)
O4B—H4B···O1Aⁱ	0.82 (3)	2.36 (3)	3.1726 (18)	174 (2)

Symmetry code: (i) x+1, y, z.

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