Unravelling the chemical basis of the bathochromic shift in the lobster carapace; new crystal structures of unbound astaxanthin, canthaxanthin and zeaxanthin

The crystal structures of the unbound carotenoids, synthetic astaxanthin (3S,3′S:3R,3′S:3R,3′R in a 1:2:1 ratio), canthaxanthin and (3R,3′S, meso)-zeaxanthin are compared with each other and the protein bound astaxanthin molecule in the carotenoprotein, β-crustacyanin. Three new crystal forms of astaxanthin have been obtained, using different crystallization conditions, comprising a chloroform solvate, a pyridine solvate and an unsolvated form. In each structure, the astaxanthin molecules, which are similar to one another, are centrosymmetric and adopt the 6-s-cis conformation; the end rings are bent out of the plane of the polyene chain by angles of −42.6 (5), −48.9 (5) and −50.4 (3)°, respectively, and are disordered, showing the presence of both R and S configurations (in a 1:1 ratio). In the crystal packing of the chloroform and pyridine solvates, the astaxanthin molecules show pair-wise end-to-end intermolecular hydrogen bonding of the adjacent 3-hydroxyl and 4-keto oxygens, whereas in the unsolvated crystal form, the hydrogen-bonding interaction is intermolecular. In addition, there are intermolecular C—H hydrogen bonds in all three structures. The canthaxanthin structure, measured at 100 and 293 K, also adopts the 6-s-cis conformation, but with disorder of one end ring only. The rotation of the end rings out of the plane of the polyene chains (ca −50 ° for each structure) is similar to that of astaxanthin. A number of possible C—H hydrogen bonds to the keto O atoms are also observed. (3R,3′S, meso)-zeaxanthin is centrosymmetric with a C5—C6—C7—C8 torsion angle of −74.9 (3)°; the molecules show pair-wise hydrogen bonding between the hydroxyl O atoms. In addition, for all the crystal structures the polyene chains were arranged one above the other, with intermolecular distances of 3.61–3.79 Å, indicating the presence of π-stacking interactions. Overall, these six crystal structures provide an ensemble of experimentally derived results that allow several key parameters, thought to influence colour tuning of the bathochromic shift of astaxanthin in crustacyanin, to be varied. The fact that the colour of each of the six crystals remains red, rather than turning blue, is therefore especially significant.

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures

(axt-CL)

Crystal data

C40H52O4·2(CHCl3)	Z = 1
Mr = 835.55	F(000) = 440
Triclinic, P1	Dx = 1.303 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9588 (8) Å	Cell parameters from 1032 reflections
b = 11.8583 (16) Å	θ = 2.4–21.9°
c = 15.647 (2) Å	µ = 0.44 mm^−1
α = 79.036 (2)°	T = 100 K
β = 80.499 (3)°	Needle, red
γ = 82.506 (2)°	0.65 × 0.05 × 0.02 mm
V = 1065.0 (3) Å^3

Data collection

CCD area detector diffractometer	1776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
phi and ω scans	h = −7→7
7182 measured reflections	k = −14→14
3634 independent reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 0.80	w = 1/[σ^2(Fo^2) + (0.0281P)^2] where P = (Fo^2 + 2Fc^2)/3
3634 reflections	(Δ/σ)max = 0.005
259 parameters	Δρmax = 0.54 e Å^−3
2 restraints	Δρmin = −0.57 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	1.4708 (4)	−0.17695 (19)	0.98503 (15)	0.0380 (7)
H3O	1.519 (6)	−0.119 (2)	0.997 (2)	0.057*
O4	1.2603 (4)	0.03925 (19)	0.95696 (15)	0.0375 (7)
C1	1.1646 (6)	−0.1841 (3)	0.7949 (2)	0.0334 (10)
C2A	1.2522 (13)	−0.2224 (6)	0.8912 (5)	0.024 (2)	0.508 (8)
H2A	1.1188	−0.2327	0.9379	0.029*	0.508 (8)
H2B	1.3495	−0.2970	0.8932	0.029*	0.508 (8)
C3A	1.3848 (13)	−0.1323 (6)	0.9069 (5)	0.018 (2)	0.508 (8)
H3A	1.5128	−0.1168	0.8575	0.021*	0.508 (8)
C2B	1.3610 (10)	−0.2017 (5)	0.8464 (4)	0.024 (2)	0.492 (8)
H2C	1.4195	−0.2845	0.8571	0.029*	0.492 (8)
H2D	1.4868	−0.1572	0.8134	0.029*	0.492 (8)
C3B	1.2757 (10)	−0.1611 (5)	0.9320 (4)	0.025 (3)	0.492 (8)
H3B	1.1412	−0.2007	0.9652	0.030*	0.492 (8)
C4	1.2184 (6)	−0.0258 (3)	0.9112 (2)	0.0325 (9)
C5	1.0661 (5)	0.0102 (3)	0.8442 (2)	0.0227 (8)
C6	1.0446 (5)	−0.0602 (3)	0.7884 (2)	0.0241 (8)
C7	0.9169 (5)	−0.0221 (3)	0.7136 (2)	0.0271 (9)
H7	0.9863	−0.0462	0.6599	0.033*
C8	0.7147 (5)	0.0423 (3)	0.7113 (2)	0.0227 (8)
H8	0.6356	0.0610	0.7655	0.027*
C9	0.6068 (5)	0.0856 (3)	0.6337 (2)	0.0213 (8)
C10	0.4047 (5)	0.1530 (3)	0.6400 (2)	0.0208 (8)
H10	0.3342	0.1613	0.6978	0.025*
C11	0.2852 (5)	0.2130 (3)	0.5699 (2)	0.0223 (8)
H11	0.3531	0.2074	0.5113	0.027*
C12	0.0828 (5)	0.2768 (2)	0.5818 (2)	0.0217 (8)
H12	0.0157	0.2785	0.6411	0.026*
C13	−0.0445 (5)	0.3431 (3)	0.5147 (2)	0.0206 (8)
C14	−0.2506 (5)	0.3999 (3)	0.5391 (2)	0.0231 (8)
H14	−0.3030	0.3898	0.6005	0.028*
C15	−0.3988 (5)	0.4730 (3)	0.4844 (2)	0.0252 (8)
H15	−0.3527	0.4845	0.4225	0.030*
C16	0.9822 (6)	−0.2684 (3)	0.8116 (2)	0.0321 (9)
H16A	1.0559	−0.3478	0.8187	0.048*
H16B	0.8967	−0.2542	0.7615	0.048*
H16C	0.8770	−0.2572	0.8651	0.048*
C17	1.3226 (6)	−0.2024 (3)	0.7107 (3)	0.0604 (14)
H17A	1.4333	−0.1449	0.6962	0.091*
H17B	1.2321	−0.1940	0.6625	0.091*
H17C	1.4043	−0.2800	0.7191	0.091*
C18	0.9535 (6)	0.1329 (2)	0.8413 (2)	0.0286 (9)
H18A	0.9135	0.1634	0.7824	0.043*
H18B	1.0597	0.1812	0.8551	0.043*
H18C	0.8146	0.1335	0.8847	0.043*
C19	0.7298 (5)	0.0573 (3)	0.5475 (2)	0.0309 (9)
H19A	0.6353	0.0887	0.5011	0.046*
H19B	0.7589	−0.0267	0.5518	0.046*
H19C	0.8755	0.0914	0.5334	0.046*
C20	0.0634 (6)	0.3457 (3)	0.4203 (2)	0.0298 (9)
H20A	−0.0391	0.3928	0.3814	0.045*
H20B	0.0898	0.2668	0.4075	0.045*
H20C	0.2095	0.3790	0.4106	0.045*
C1S	0.4638 (6)	0.3863 (3)	0.8698 (2)	0.0372 (10)
H1S	0.5068	0.3049	0.8978	0.045*
Cl1S	0.26261 (17)	0.45298 (8)	0.94431 (6)	0.0479 (3)
Cl2S	0.3449 (2)	0.38433 (11)	0.77444 (7)	0.0714 (4)
Cl3S	0.70928 (18)	0.45829 (11)	0.84040 (8)	0.0687 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0517 (19)	0.0321 (16)	0.0325 (15)	0.0125 (14)	−0.0241 (14)	−0.0068 (13)
O4	0.0426 (17)	0.0325 (15)	0.0398 (16)	0.0089 (13)	−0.0187 (14)	−0.0101 (13)
C1	0.028 (2)	0.020 (2)	0.056 (3)	0.0015 (18)	−0.022 (2)	−0.0064 (19)
C2A	0.021 (5)	0.014 (4)	0.038 (6)	0.004 (4)	−0.016 (4)	−0.003 (4)
C3A	0.017 (5)	0.017 (5)	0.020 (5)	−0.002 (4)	−0.004 (4)	−0.004 (4)
C2B	0.023 (5)	0.021 (5)	0.023 (5)	0.003 (4)	0.005 (4)	−0.003 (4)
C3B	0.014 (6)	0.028 (6)	0.029 (5)	−0.003 (4)	−0.004 (4)	0.006 (4)
C4	0.037 (2)	0.036 (2)	0.022 (2)	0.005 (2)	−0.0028 (19)	−0.0064 (19)
C5	0.017 (2)	0.023 (2)	0.0233 (19)	0.0049 (16)	−0.0010 (16)	0.0003 (16)
C6	0.0131 (19)	0.019 (2)	0.038 (2)	0.0014 (16)	−0.0051 (18)	−0.0020 (17)
C7	0.023 (2)	0.023 (2)	0.038 (2)	0.0025 (17)	−0.0080 (18)	−0.0098 (17)
C8	0.021 (2)	0.0194 (19)	0.027 (2)	−0.0046 (16)	−0.0010 (17)	−0.0039 (16)
C9	0.017 (2)	0.0168 (19)	0.031 (2)	−0.0019 (16)	−0.0056 (17)	−0.0030 (16)
C10	0.017 (2)	0.0198 (19)	0.025 (2)	−0.0013 (16)	−0.0016 (16)	−0.0048 (16)
C11	0.022 (2)	0.0189 (19)	0.028 (2)	−0.0017 (16)	−0.0053 (17)	−0.0068 (16)
C12	0.021 (2)	0.0193 (19)	0.0248 (19)	−0.0024 (16)	−0.0042 (17)	−0.0020 (16)
C13	0.021 (2)	0.0164 (19)	0.025 (2)	−0.0025 (16)	−0.0084 (17)	−0.0013 (16)
C14	0.022 (2)	0.0197 (19)	0.027 (2)	−0.0020 (16)	−0.0057 (17)	−0.0021 (16)
C15	0.023 (2)	0.023 (2)	0.029 (2)	−0.0032 (16)	−0.0086 (18)	0.0012 (16)
C16	0.036 (2)	0.023 (2)	0.034 (2)	0.0011 (18)	−0.0039 (19)	−0.0025 (17)
C17	0.033 (3)	0.021 (2)	0.115 (4)	0.0016 (19)	0.021 (3)	−0.012 (2)
C18	0.033 (2)	0.024 (2)	0.027 (2)	0.0060 (17)	−0.0053 (18)	−0.0036 (16)
C19	0.022 (2)	0.032 (2)	0.041 (2)	0.0061 (17)	−0.0094 (18)	−0.0143 (18)
C20	0.030 (2)	0.029 (2)	0.033 (2)	0.0034 (17)	−0.0119 (19)	−0.0086 (17)
C1S	0.038 (3)	0.030 (2)	0.037 (2)	0.0056 (19)	0.000 (2)	−0.0012 (18)
Cl1S	0.0488 (7)	0.0465 (7)	0.0408 (6)	0.0145 (5)	0.0004 (5)	−0.0076 (5)
Cl2S	0.0767 (9)	0.1042 (10)	0.0465 (7)	−0.0446 (8)	0.0001 (7)	−0.0294 (7)
Cl3S	0.0407 (7)	0.1008 (10)	0.0723 (8)	−0.0212 (7)	−0.0011 (6)	−0.0311 (7)

Geometric parameters (Å, º)

O3—C3A	1.389 (8)	C10—H10	0.9500
O3—C3B	1.509 (6)	C11—C12	1.342 (4)
O3—H3O	0.834 (17)	C11—H11	0.9500
O4—C4	1.220 (4)	C12—C13	1.446 (4)
C1—C2B	1.499 (7)	C12—H12	0.9500
C1—C17	1.522 (5)	C13—C14	1.355 (4)
C1—C16	1.530 (4)	C13—C20	1.507 (4)
C1—C6	1.540 (4)	C14—C15	1.425 (4)
C1—C2A	1.640 (8)	C14—H14	0.9500
C2A—C3A	1.487 (9)	C15—C15^i	1.351 (6)
C2A—H2A	0.9900	C15—H15	0.9500
C2A—H2B	0.9900	C16—H16A	0.9800
C3A—C4	1.505 (8)	C16—H16B	0.9800
C3A—H3A	1.0000	C16—H16C	0.9800
C2B—C3B	1.4971	C17—H17A	0.9800
C2B—H2C	0.9900	C17—H17B	0.9800
C2B—H2D	0.9900	C17—H17C	0.9800
C3B—C4	1.579 (7)	C18—H18A	0.9800
C3B—H3B	1.0000	C18—H18B	0.9800
C4—C5	1.466 (4)	C18—H18C	0.9800
C5—C6	1.349 (4)	C19—H19A	0.9800
C5—C18	1.517 (4)	C19—H19B	0.9800
C6—C7	1.469 (4)	C19—H19C	0.9800
C7—C8	1.341 (4)	C20—H20A	0.9800
C7—H7	0.9500	C20—H20B	0.9800
C8—C9	1.445 (4)	C20—H20C	0.9800
C8—H8	0.9500	C1S—Cl3S	1.742 (4)
C9—C10	1.356 (4)	C1S—Cl1S	1.751 (3)
C9—C19	1.499 (4)	C1S—Cl2S	1.759 (3)
C10—C11	1.430 (4)	C1S—H1S	1.0000
C3A—O3—H3O	102 (2)	C9—C10—C11	127.7 (3)
C3B—O3—H3O	120 (2)	C9—C10—H10	116.2
C2B—C1—C17	92.1 (3)	C11—C10—H10	116.2
C2B—C1—C16	122.5 (3)	C12—C11—C10	124.0 (3)
C17—C1—C16	108.2 (3)	C12—C11—H11	118.0
C2B—C1—C6	112.1 (3)	C10—C11—H11	118.0
C17—C1—C6	112.1 (3)	C11—C12—C13	127.3 (3)
C16—C1—C6	108.6 (3)	C11—C12—H12	116.3
C17—C1—C2A	121.2 (4)	C13—C12—H12	116.3
C16—C1—C2A	96.4 (4)	C14—C13—C12	119.2 (3)
C6—C1—C2A	108.7 (4)	C14—C13—C20	123.6 (3)
C3A—C2A—C1	109.7 (6)	C12—C13—C20	117.3 (3)
C3A—C2A—H2A	109.7	C13—C14—C15	128.3 (3)
C1—C2A—H2A	109.7	C13—C14—H14	115.8
C3A—C2A—H2B	109.7	C15—C14—H14	115.8
C1—C2A—H2B	109.7	C15^i—C15—C14	123.7 (4)
H2A—C2A—H2B	108.2	C15^i—C15—H15	118.2
O3—C3A—C2A	105.7 (6)	C14—C15—H15	118.2
O3—C3A—C4	113.9 (5)	C1—C16—H16A	109.5
C2A—C3A—C4	106.0 (5)	C1—C16—H16B	109.5
O3—C3A—H3A	110.3	H16A—C16—H16B	109.5
C2A—C3A—H3A	110.3	C1—C16—H16C	109.5
C4—C3A—H3A	110.3	H16A—C16—H16C	109.5
C3B—C2B—C1	107.8 (3)	H16B—C16—H16C	109.5
C3B—C2B—H2C	110.2	C1—C17—H17A	109.5
C1—C2B—H2C	110.2	C1—C17—H17B	109.5
C3B—C2B—H2D	110.2	H17A—C17—H17B	109.5
C1—C2B—H2D	110.2	C1—C17—H17C	109.5
H2C—C2B—H2D	108.5	H17A—C17—H17C	109.5
C2B—C3B—O3	108.9 (2)	H17B—C17—H17C	109.5
C2B—C3B—C4	107.6 (2)	C5—C18—H18A	109.5
O3—C3B—C4	103.6 (4)	C5—C18—H18B	109.5
C2B—C3B—H3B	112.1	H18A—C18—H18B	109.5
O3—C3B—H3B	112.1	C5—C18—H18C	109.5
C4—C3B—H3B	112.1	H18A—C18—H18C	109.5
O4—C4—C5	122.9 (3)	H18B—C18—H18C	109.5
O4—C4—C3A	115.3 (4)	C9—C19—H19A	109.5
C5—C4—C3A	119.3 (4)	C9—C19—H19B	109.5
O4—C4—C3B	123.2 (3)	H19A—C19—H19B	109.5
C5—C4—C3B	112.6 (3)	C9—C19—H19C	109.5
C6—C5—C4	120.9 (3)	H19A—C19—H19C	109.5
C6—C5—C18	125.2 (3)	H19B—C19—H19C	109.5
C4—C5—C18	113.8 (3)	C13—C20—H20A	109.5
C5—C6—C7	122.5 (3)	C13—C20—H20B	109.5
C5—C6—C1	122.5 (3)	H20A—C20—H20B	109.5
C7—C6—C1	114.9 (3)	C13—C20—H20C	109.5
C8—C7—C6	128.2 (3)	H20A—C20—H20C	109.5
C8—C7—H7	115.9	H20B—C20—H20C	109.5
C6—C7—H7	115.9	Cl3S—C1S—Cl1S	111.22 (19)
C7—C8—C9	125.7 (3)	Cl3S—C1S—Cl2S	109.04 (19)
C7—C8—H8	117.2	Cl1S—C1S—Cl2S	109.92 (19)
C9—C8—H8	117.2	Cl3S—C1S—H1S	108.9
C10—C9—C8	119.8 (3)	Cl1S—C1S—H1S	108.9
C10—C9—C19	122.3 (3)	Cl2S—C1S—H1S	108.9
C8—C9—C19	117.9 (3)
C2B—C1—C2A—C3A	51.0 (8)	C3B—C4—C5—C6	−20.4 (5)
C17—C1—C2A—C3A	81.1 (6)	O4—C4—C5—C18	−3.9 (5)
C16—C1—C2A—C3A	−163.2 (5)	C3A—C4—C5—C18	−164.8 (4)
C6—C1—C2A—C3A	−51.0 (6)	C3B—C4—C5—C18	163.3 (3)
C3B—O3—C3A—C2A	−39.7 (7)	C4—C5—C6—C7	−172.1 (3)
C3B—O3—C3A—C4	76.3 (8)	C18—C5—C6—C7	3.8 (5)
C1—C2A—C3A—O3	−174.2 (5)	C4—C5—C6—C1	3.9 (5)
C1—C2A—C3A—C4	64.6 (7)	C18—C5—C6—C1	179.8 (3)
C17—C1—C2B—C3B	166.22 (17)	C2B—C1—C6—C5	−19.3 (5)
C16—C1—C2B—C3B	−80.6 (3)	C17—C1—C6—C5	−121.3 (4)
C6—C1—C2B—C3B	51.3 (3)	C16—C1—C6—C5	119.2 (3)
C2A—C1—C2B—C3B	−39.1 (6)	C2A—C1—C6—C5	15.4 (5)
C1—C2B—C3B—O3	−179.5 (5)	C2B—C1—C6—C7	156.9 (3)
C1—C2B—C3B—C4	−67.8 (3)	C17—C1—C6—C7	54.9 (4)
C3A—O3—C3B—C2B	53.7 (8)	C16—C1—C6—C7	−64.5 (4)
C3A—O3—C3B—C4	−60.6 (8)	C2A—C1—C6—C7	−168.3 (4)
O3—C3A—C4—O4	35.5 (7)	C5—C6—C7—C8	−42.6 (5)
C2A—C3A—C4—O4	151.3 (5)	C1—C6—C7—C8	141.1 (3)
O3—C3A—C4—C5	−162.2 (4)	C6—C7—C8—C9	174.2 (3)
C2A—C3A—C4—C5	−46.5 (7)	C7—C8—C9—C10	−178.0 (3)
O3—C3A—C4—C3B	−77.8 (9)	C7—C8—C9—C19	−0.3 (5)
C2A—C3A—C4—C3B	38.0 (6)	C8—C9—C10—C11	173.0 (3)
C2B—C3B—C4—O4	−140.4 (3)	C19—C9—C10—C11	−4.6 (5)
O3—C3B—C4—O4	−25.2 (5)	C9—C10—C11—C12	178.9 (3)
C2B—C3B—C4—C5	52.4 (3)	C10—C11—C12—C13	177.6 (3)
O3—C3B—C4—C5	167.6 (3)	C11—C12—C13—C14	178.1 (3)
C2B—C3B—C4—C3A	−57.4 (8)	C11—C12—C13—C20	−2.5 (5)
O3—C3B—C4—C3A	57.8 (7)	C12—C13—C14—C15	177.4 (3)
O4—C4—C5—C6	172.4 (3)	C20—C13—C14—C15	−2.0 (5)
C3A—C4—C5—C6	11.6 (6)	C13—C14—C15—C15^i	−179.3 (4)

Symmetry code: (i) −x−1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···O3^ii	0.98	2.52	3.460 (4)	161
C18—H18C···O4^ii	0.98	2.91	3.557 (4)	124
C1S—H1S···O3^ii	1.00	2.16	3.061 (4)	149
O3—H3O···O4^iii	0.83 (2)	2.02 (2)	2.790 (3)	154 (3)

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

(axt-PY)

Crystal data

C40H52O4·2(C5H5N)	F(000) = 816
Mr = 755.02	Dx = 1.156 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1008 reflections
a = 18.568 (4) Å	θ = 2.2–19.6°
b = 6.1926 (13) Å	µ = 0.07 mm^−1
c = 19.803 (4) Å	T = 100 K
β = 107.746 (4)°	Plate, red
V = 2168.7 (8) Å^3	0.60 × 0.15 × 0.05 mm
Z = 2

Data collection

CCD area detector diffractometer	1400 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.148
Graphite monochromator	θmax = 23.3°, θmin = 1.3°
phi and ω scans	h = −20→20
12345 measured reflections	k = −6→6
3104 independent reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0351P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.77	(Δ/σ)max < 0.001
3103 reflections	Δρmax = 0.26 e Å^−3
292 parameters	Δρmin = −0.17 e Å^−3
7 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.57811 (14)	0.8999 (5)	0.60122 (15)	0.0528 (8)
H3O	0.558 (3)	0.989 (7)	0.570 (2)	0.18 (3)*
O4	0.45807 (13)	0.7535 (4)	0.49578 (13)	0.0482 (7)
C1	0.48894 (17)	0.5126 (5)	0.69853 (16)	0.0327 (9)
C2A	0.5522 (6)	0.6276 (17)	0.6678 (6)	0.025 (3)	0.508 (16)
H2A	0.5919	0.6941	0.7077	0.030*	0.508 (16)
H2B	0.5766	0.5158	0.6464	0.030*	0.508 (16)
C3A	0.5178 (8)	0.801 (2)	0.6122 (7)	0.036 (3)	0.508 (16)
H3A	0.4883	0.9067	0.6314	0.044*	0.508 (16)
C2B	0.5248 (7)	0.713 (2)	0.6869 (5)	0.034 (3)	0.492 (16)
H2C	0.4908	0.8361	0.6867	0.040*	0.492 (16)
H2D	0.5723	0.7350	0.7261	0.040*	0.492 (16)
C3B	0.5413 (8)	0.705 (3)	0.6198 (7)	0.032 (3)	0.492 (16)
H3B	0.5749	0.5778	0.6209	0.039*	0.492 (16)
C4	0.46642 (19)	0.6753 (6)	0.5545 (2)	0.0366 (9)
C5	0.41454 (17)	0.5161 (5)	0.56773 (17)	0.0312 (8)
C6	0.42262 (17)	0.4456 (5)	0.63385 (16)	0.0290 (8)
C7	0.36648 (18)	0.3087 (5)	0.65139 (16)	0.0323 (9)
H7	0.3515	0.3543	0.6909	0.039*
C8	0.33352 (17)	0.1286 (5)	0.61948 (17)	0.0310 (9)
H8	0.3510	0.0719	0.5827	0.037*
C9	0.27369 (17)	0.0130 (5)	0.63610 (15)	0.0279 (8)
C10	0.24396 (17)	−0.1670 (5)	0.59864 (16)	0.0324 (9)
H10	0.2678	−0.2171	0.5654	0.039*
C11	0.18050 (17)	−0.2889 (5)	0.60406 (16)	0.0291 (8)
H11	0.1548	−0.2383	0.6358	0.035*
C12	0.15466 (17)	−0.4716 (5)	0.56696 (16)	0.0316 (9)
H12	0.1820	−0.5239	0.5368	0.038*
C13	0.08999 (17)	−0.5921 (5)	0.56925 (16)	0.0286 (8)
C14	0.07096 (18)	−0.7735 (5)	0.52928 (17)	0.0330 (9)
H14	0.1042	−0.8131	0.5031	0.040*
C15	0.00756 (18)	−0.9129 (5)	0.52135 (16)	0.0337 (9)
H15	−0.0260	−0.8807	0.5478	0.040*
C16	0.53545 (19)	0.3179 (5)	0.72941 (19)	0.0558 (12)
H16A	0.5803	0.3630	0.7676	0.084*
H16B	0.5512	0.2445	0.6924	0.084*
H16C	0.5052	0.2189	0.7484	0.084*
C17B	0.4597 (7)	0.566 (2)	0.7660 (6)	0.043 (3)	0.492 (16)
H17D	0.4992	0.6442	0.8019	0.064*	0.492 (16)
H17E	0.4481	0.4308	0.7863	0.064*	0.492 (16)
H17F	0.4140	0.6553	0.7505	0.064*	0.492 (16)
C17A	0.4655 (6)	0.662 (2)	0.7422 (6)	0.037 (3)	0.508 (16)
H17A	0.5101	0.7299	0.7753	0.055*	0.508 (16)
H17B	0.4366	0.5865	0.7688	0.055*	0.508 (16)
H17C	0.4338	0.7739	0.7124	0.055*	0.508 (16)
C18	0.34977 (17)	0.4544 (5)	0.50338 (16)	0.0402 (10)
H18A	0.3077	0.3995	0.5186	0.060*
H18B	0.3665	0.3422	0.4766	0.060*
H18C	0.3331	0.5816	0.4732	0.060*
C19	0.24443 (18)	0.1028 (5)	0.69328 (16)	0.0354 (9)
H19A	0.2009	0.0174	0.6959	0.053*
H19B	0.2289	0.2533	0.6823	0.053*
H19C	0.2844	0.0964	0.7389	0.053*
C20	0.04498 (18)	−0.5103 (5)	0.61525 (16)	0.0369 (9)
H20A	0.0001	−0.6011	0.6086	0.055*
H20B	0.0293	−0.3611	0.6021	0.055*
H20C	0.0761	−0.5153	0.6650	0.055*
N1S	0.8447 (2)	1.2338 (7)	0.60132 (18)	0.0753 (11)
C1S	0.8400 (2)	1.4178 (7)	0.6339 (2)	0.0493 (11)
H1S	0.8734	1.5317	0.6315	0.059*
C2S	0.7904 (3)	1.4516 (8)	0.6701 (2)	0.0700 (14)
H2S	0.7896	1.5857	0.6931	0.084*
C3S	0.7421 (3)	1.2933 (12)	0.6732 (3)	0.106 (3)
H3S	0.7068	1.3160	0.6985	0.127*
C4S	0.7433 (3)	1.1008 (11)	0.6405 (4)	0.116 (3)
H4S	0.7097	0.9870	0.6426	0.139*
C5S	0.7947 (4)	1.0789 (8)	0.6046 (2)	0.0905 (19)
H5S	0.7954	0.9469	0.5803	0.109*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0412 (17)	0.0558 (19)	0.0609 (19)	−0.0266 (16)	0.0150 (15)	−0.0020 (16)
O4	0.0456 (16)	0.0490 (17)	0.0486 (18)	−0.0101 (13)	0.0121 (14)	0.0072 (14)
C1	0.033 (2)	0.025 (2)	0.034 (2)	−0.0012 (18)	0.0014 (18)	−0.0067 (18)
C2A	0.021 (5)	0.020 (5)	0.033 (6)	−0.003 (4)	0.005 (4)	−0.004 (4)
C3A	0.037 (8)	0.030 (8)	0.033 (6)	−0.001 (5)	−0.004 (5)	0.016 (6)
C2B	0.035 (6)	0.038 (7)	0.032 (5)	−0.006 (5)	0.015 (4)	−0.003 (5)
C3B	0.026 (7)	0.033 (9)	0.030 (6)	−0.015 (5)	−0.003 (6)	0.016 (7)
C4	0.035 (2)	0.036 (2)	0.040 (2)	−0.0065 (19)	0.013 (2)	−0.0054 (19)
C5	0.0262 (19)	0.032 (2)	0.035 (2)	−0.0069 (18)	0.0085 (17)	−0.0086 (18)
C6	0.032 (2)	0.022 (2)	0.032 (2)	−0.0024 (16)	0.0075 (16)	0.0001 (16)
C7	0.040 (2)	0.028 (2)	0.025 (2)	−0.0039 (18)	0.0041 (17)	−0.0013 (16)
C8	0.029 (2)	0.029 (2)	0.032 (2)	0.0035 (18)	0.0059 (16)	0.0004 (17)
C9	0.0325 (19)	0.023 (2)	0.0253 (19)	−0.0005 (18)	0.0051 (16)	0.0029 (16)
C10	0.033 (2)	0.031 (2)	0.031 (2)	0.0004 (18)	0.0075 (17)	0.0019 (17)
C11	0.027 (2)	0.030 (2)	0.029 (2)	−0.0012 (17)	0.0059 (16)	0.0057 (16)
C12	0.032 (2)	0.032 (2)	0.030 (2)	−0.0031 (18)	0.0085 (16)	−0.0036 (17)
C13	0.027 (2)	0.031 (2)	0.0242 (19)	−0.0053 (18)	0.0028 (15)	0.0035 (16)
C14	0.031 (2)	0.035 (2)	0.031 (2)	−0.0076 (18)	0.0080 (17)	0.0011 (17)
C15	0.031 (2)	0.037 (2)	0.031 (2)	−0.0049 (19)	0.0079 (17)	0.0034 (15)
C16	0.052 (2)	0.040 (2)	0.054 (3)	−0.005 (2)	−0.016 (2)	−0.003 (2)
C17B	0.049 (6)	0.059 (9)	0.023 (6)	−0.016 (6)	0.015 (5)	−0.013 (5)
C17A	0.037 (5)	0.045 (7)	0.032 (6)	−0.011 (5)	0.017 (5)	0.005 (5)
C18	0.035 (2)	0.048 (2)	0.034 (2)	−0.0042 (19)	0.0050 (18)	0.0006 (18)
C19	0.044 (2)	0.031 (2)	0.030 (2)	−0.0047 (18)	0.0085 (17)	0.0005 (16)
C20	0.038 (2)	0.038 (2)	0.031 (2)	−0.0050 (19)	0.0058 (17)	0.0015 (17)
N1S	0.098 (3)	0.070 (3)	0.062 (3)	0.016 (3)	0.030 (2)	0.013 (2)
C1S	0.037 (2)	0.052 (3)	0.049 (3)	−0.007 (2)	0.000 (2)	0.000 (2)
C2S	0.084 (4)	0.089 (4)	0.033 (3)	0.043 (3)	0.012 (3)	0.004 (2)
C3S	0.060 (4)	0.174 (7)	0.098 (5)	0.050 (5)	0.046 (4)	0.103 (5)
C4S	0.049 (4)	0.127 (6)	0.128 (6)	−0.045 (4)	−0.037 (4)	0.096 (5)
C5S	0.137 (6)	0.042 (3)	0.056 (3)	−0.025 (4)	−0.026 (3)	0.002 (3)

Geometric parameters (Å, º)

O3—C3A	1.351 (14)	C13—C14	1.358 (4)
O3—C3B	1.489 (13)	C13—C20	1.500 (4)
O3—H3O	0.82 (2)	C14—C15	1.429 (4)
O4—C4	1.225 (4)	C14—H14	0.9500
C1—C17A	1.423 (11)	C15—C15^i	1.346 (6)
C1—C2B	1.458 (9)	C15—H15	0.9500
C1—C16	1.501 (4)	C16—H16A	0.9800
C1—C6	1.539 (4)	C16—H16B	0.9800
C1—C17B	1.622 (11)	C16—H16C	0.9800
C1—C2A	1.641 (11)	C17B—H17D	0.9800
C2A—C3A	1.532 (19)	C17B—H17E	0.9800
C2A—H2A	0.9900	C17B—H17F	0.9800
C2A—H2B	0.9900	C17A—H17A	0.9800
C3A—C4	1.468 (13)	C17A—H17B	0.9800
C3A—H3A	1.0000	C17A—H17C	0.9800
C2B—C3B	1.45 (2)	C18—H18A	0.9800
C2B—H2C	0.9900	C18—H18B	0.9800
C2B—H2D	0.9900	C18—H18C	0.9800
C3B—C4	1.594 (13)	C19—H19A	0.9800
C3B—H3B	1.0000	C19—H19B	0.9800
C4—C5	1.457 (4)	C19—H19C	0.9800
C5—C6	1.345 (4)	C20—H20A	0.9800
C5—C18	1.511 (4)	C20—H20B	0.9800
C6—C7	1.465 (4)	C20—H20C	0.9800
C7—C8	1.335 (4)	N1S—C1S	1.325 (4)
C7—H7	0.9500	N1S—C5S	1.351 (5)
C8—C9	1.442 (4)	C1S—C2S	1.345 (5)
C8—H8	0.9500	C1S—H1S	0.9500
C9—C10	1.359 (4)	C2S—C3S	1.343 (6)
C9—C19	1.504 (4)	C2S—H2S	0.9500
C10—C11	1.431 (4)	C3S—C4S	1.360 (6)
C10—H10	0.9500	C3S—H3S	0.9500
C11—C12	1.355 (4)	C4S—C5S	1.359 (6)
C11—H11	0.9500	C4S—H4S	0.9500
C12—C13	1.426 (4)	C5S—H5S	0.9500
C12—H12	0.9500
C3A—O3—H3O	102 (5)	C12—C11—H11	117.9
C3B—O3—H3O	126 (4)	C10—C11—H11	117.9
C17A—C1—C2B	77.3 (5)	C11—C12—C13	125.6 (3)
C17A—C1—C16	121.4 (6)	C11—C12—H12	117.2
C2B—C1—C16	120.9 (6)	C13—C12—H12	117.2
C17A—C1—C6	111.5 (5)	C14—C13—C12	119.1 (3)
C2B—C1—C6	112.7 (4)	C14—C13—C20	122.6 (3)
C16—C1—C6	109.7 (3)	C12—C13—C20	118.2 (3)
C2B—C1—C17B	103.9 (5)	C13—C14—C15	128.5 (3)
C16—C1—C17B	97.1 (6)	C13—C14—H14	115.7
C6—C1—C17B	110.9 (5)	C15—C14—H14	115.7
C17A—C1—C2A	109.1 (5)	C15^i—C15—C14	124.1 (4)
C16—C1—C2A	96.4 (5)	C15^i—C15—H15	118.0
C6—C1—C2A	106.9 (4)	C14—C15—H15	118.0
C17B—C1—C2A	132.4 (5)	C1—C16—H16A	109.5
C3A—C2A—C1	112.5 (10)	C1—C16—H16B	109.5
C3A—C2A—H2A	109.1	H16A—C16—H16B	109.5
C1—C2A—H2A	109.1	C1—C16—H16C	109.5
C3A—C2A—H2B	109.1	H16A—C16—H16C	109.5
C1—C2A—H2B	109.1	H16B—C16—H16C	109.5
H2A—C2A—H2B	107.8	C1—C17B—H17D	109.5
O3—C3A—C4	119.3 (10)	C1—C17B—H17E	109.5
O3—C3A—C2A	104.4 (12)	H17D—C17B—H17E	109.5
C4—C3A—C2A	102.6 (11)	C1—C17B—H17F	109.5
O3—C3A—H3A	110.0	H17D—C17B—H17F	109.5
C4—C3A—H3A	110.0	H17E—C17B—H17F	109.5
C2A—C3A—H3A	110.0	C1—C17A—H17A	109.5
C3B—C2B—C1	110.4 (13)	C1—C17A—H17B	109.5
C3B—C2B—H2C	109.6	C1—C17A—H17C	109.5
C1—C2B—H2C	109.6	C5—C18—H18A	109.5
C3B—C2B—H2D	109.6	C5—C18—H18B	109.5
C1—C2B—H2D	109.6	H18A—C18—H18B	109.5
H2C—C2B—H2D	108.1	C5—C18—H18C	109.5
C2B—C3B—O3	116.0 (12)	H18A—C18—H18C	109.5
C2B—C3B—C4	111.8 (11)	H18B—C18—H18C	109.5
O3—C3B—C4	104.2 (9)	C9—C19—H19A	109.5
C2B—C3B—H3B	108.2	C9—C19—H19B	109.5
O3—C3B—H3B	108.2	H19A—C19—H19B	109.5
C4—C3B—H3B	108.2	C9—C19—H19C	109.5
O4—C4—C5	122.6 (3)	H19A—C19—H19C	109.5
O4—C4—C3A	113.2 (6)	H19B—C19—H19C	109.5
C5—C4—C3A	121.8 (6)	C13—C20—H20A	109.5
O4—C4—C3B	123.5 (6)	C13—C20—H20B	109.5
C5—C4—C3B	113.1 (5)	H20A—C20—H20B	109.5
C6—C5—C4	120.7 (3)	C13—C20—H20C	109.5
C6—C5—C18	124.3 (3)	H20A—C20—H20C	109.5
C4—C5—C18	114.8 (3)	H20B—C20—H20C	109.5
C5—C6—C7	122.9 (3)	C1S—N1S—C5S	116.1 (4)
C5—C6—C1	123.1 (3)	N1S—C1S—C2S	123.4 (4)
C7—C6—C1	113.9 (3)	N1S—C1S—H1S	118.3
C8—C7—C6	128.9 (3)	C2S—C1S—H1S	118.3
C8—C7—H7	115.6	C3S—C2S—C1S	119.1 (5)
C6—C7—H7	115.6	C3S—C2S—H2S	120.5
C7—C8—C9	125.5 (3)	C1S—C2S—H2S	120.5
C7—C8—H8	117.2	C2S—C3S—C4S	120.7 (6)
C9—C8—H8	117.2	C2S—C3S—H3S	119.7
C10—C9—C8	119.7 (3)	C4S—C3S—H3S	119.7
C10—C9—C19	122.3 (3)	C5S—C4S—C3S	116.9 (6)
C8—C9—C19	117.9 (3)	C5S—C4S—H4S	121.6
C9—C10—C11	126.8 (3)	C3S—C4S—H4S	121.6
C9—C10—H10	116.6	N1S—C5S—C4S	123.8 (5)
C11—C10—H10	116.6	N1S—C5S—H5S	118.1
C12—C11—C10	124.3 (3)	C4S—C5S—H5S	118.1
C17A—C1—C2A—C3A	−71.1 (14)	C3B—C4—C5—C18	−169.7 (8)
C2B—C1—C2A—C3A	−56.3 (12)	C4—C5—C6—C7	171.5 (3)
C16—C1—C2A—C3A	162.5 (10)	C18—C5—C6—C7	−3.5 (5)
C6—C1—C2A—C3A	49.6 (12)	C4—C5—C6—C1	−4.6 (5)
C17B—C1—C2A—C3A	−91.7 (14)	C18—C5—C6—C1	−179.5 (3)
C3B—O3—C3A—C4	−83 (2)	C17A—C1—C6—C5	106.0 (7)
C3B—O3—C3A—C2A	30.3 (17)	C2B—C1—C6—C5	21.3 (9)
C1—C2A—C3A—O3	170.8 (7)	C16—C1—C6—C5	−116.6 (4)
C1—C2A—C3A—C4	−64.2 (14)	C17B—C1—C6—C5	137.3 (7)
C17A—C1—C2B—C3B	−157.3 (16)	C2A—C1—C6—C5	−13.1 (6)
C16—C1—C2B—C3B	83.6 (12)	C17A—C1—C6—C7	−70.3 (7)
C6—C1—C2B—C3B	−49.0 (16)	C2B—C1—C6—C7	−155.1 (8)
C17B—C1—C2B—C3B	−169.1 (15)	C16—C1—C6—C7	67.0 (4)
C2A—C1—C2B—C3B	37.0 (13)	C17B—C1—C6—C7	−39.1 (7)
C1—C2B—C3B—O3	180.0 (6)	C2A—C1—C6—C7	170.5 (6)
C1—C2B—C3B—C4	60.8 (19)	C5—C6—C7—C8	48.9 (5)
C3A—O3—C3B—C2B	−68 (2)	C1—C6—C7—C8	−134.6 (3)
C3A—O3—C3B—C4	55.4 (17)	C6—C7—C8—C9	−174.2 (3)
O3—C3A—C4—O4	−35.5 (14)	C7—C8—C9—C10	178.8 (3)
C2A—C3A—C4—O4	−150.2 (9)	C7—C8—C9—C19	1.1 (5)
O3—C3A—C4—C5	161.8 (8)	C8—C9—C10—C11	−174.1 (3)
C2A—C3A—C4—C5	47.1 (15)	C19—C9—C10—C11	3.5 (5)
O3—C3A—C4—C3B	83 (2)	C9—C10—C11—C12	−177.8 (3)
C2A—C3A—C4—C3B	−31.4 (18)	C10—C11—C12—C13	−177.6 (3)
C2B—C3B—C4—O4	146.9 (11)	C11—C12—C13—C14	−179.7 (3)
O3—C3B—C4—O4	20.9 (14)	C11—C12—C13—C20	1.3 (5)
C2B—C3B—C4—C5	−43.3 (17)	C12—C13—C14—C15	−177.4 (3)
O3—C3B—C4—C5	−169.3 (7)	C20—C13—C14—C15	1.7 (5)
C2B—C3B—C4—C3A	72 (2)	C13—C14—C15—C15^i	178.1 (4)
O3—C3B—C4—C3A	−54.1 (17)	C5S—N1S—C1S—C2S	1.8 (6)
O4—C4—C5—C6	−175.3 (3)	N1S—C1S—C2S—C3S	−0.9 (6)
C3A—C4—C5—C6	−14.2 (9)	C1S—C2S—C3S—C4S	0.2 (7)
C3B—C4—C5—C6	14.8 (8)	C2S—C3S—C4S—C5S	−0.6 (8)
O4—C4—C5—C18	0.2 (5)	C1S—N1S—C5S—C4S	−2.2 (7)
C3A—C4—C5—C18	161.3 (8)	C3S—C4S—C5S—N1S	1.6 (8)

Symmetry code: (i) −x, −y−2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4^ii	0.82 (2)	2.03 (3)	2.822 (4)	161 (6)
C4S—H4S···O3	0.95	2.39	3.179 (6)	140

Symmetry code: (ii) −x+1, −y+2, −z+1.

(AXT-un)

Crystal data

C40H52O4	Z = 1
Mr = 596.82	F(000) = 324
Triclinic, P1	Dx = 1.080 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5371 (10) Å	Cell parameters from 1583 reflections
b = 8.6632 (11) Å	θ = 2.4–23.8°
c = 13.2984 (16) Å	µ = 0.07 mm^−1
α = 95.145 (2)°	T = 100 K
β = 107.409 (2)°	Plate, red
γ = 98.765 (2)°	0.60 × 0.30 × 0.05 mm
V = 917.93 (19) Å^3

Data collection

CCD area detector diffractometer	1991 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 25.0°, θmin = 1.6°
phi and ω scans	h = −9→10
4780 measured reflections	k = −10→10
3188 independent reflections	l = −15→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 0.84	w = 1/[σ^2(Fo^2) + (0.1154P)^2] where P = (Fo^2 + 2Fc^2)/3
3188 reflections	(Δ/σ)max = 0.007
245 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.7363 (3)	−0.4422 (3)	−0.12625 (14)	0.1312 (8)
H3	0.6345	−0.4531	−0.1611	0.197*
O4	0.4814 (2)	−0.3426 (2)	−0.08299 (14)	0.1174 (7)
C1	0.9415 (2)	−0.2241 (2)	0.15184 (17)	0.0658 (6)
C2	0.9276 (10)	−0.2806 (12)	0.0390 (6)	0.0825 (19)	0.601 (14)
H2A	1.0191	−0.3383	0.0384	0.099*	0.601 (14)
H2B	0.9398	−0.1887	0.0008	0.099*	0.601 (14)
C2B	0.8855 (14)	−0.3571 (16)	0.0537 (9)	0.075 (3)	0.399 (14)
H2C	0.9858	−0.3781	0.0361	0.091*	0.399 (14)
H2D	0.8342	−0.4551	0.0736	0.091*	0.399 (14)
C3	0.7613 (11)	−0.3878 (12)	−0.0177 (7)	0.0791 (19)	0.601 (14)
H3A	0.7544	−0.4821	0.0201	0.095*	0.601 (14)
C3B	0.7639 (18)	−0.3190 (19)	−0.0435 (10)	0.083 (3)	0.399 (14)
H3B	0.8106	−0.2170	−0.0628	0.099*	0.399 (14)
C4	0.6155 (3)	−0.3033 (3)	−0.01260 (18)	0.0775 (6)
C5	0.6364 (2)	−0.2023 (2)	0.08680 (16)	0.0636 (5)
C6	0.7885 (2)	−0.1593 (2)	0.16157 (15)	0.0542 (5)
C7	0.8173 (2)	−0.0504 (2)	0.25864 (15)	0.0559 (5)
H7	0.8734	−0.0821	0.3244	0.067*
C8	0.7712 (2)	0.0903 (2)	0.26249 (15)	0.0564 (5)
H8	0.7143	0.1200	0.1962	0.068*
C9	0.7982 (2)	0.20208 (19)	0.35634 (14)	0.0516 (5)
C10	0.7351 (2)	0.3359 (2)	0.34562 (15)	0.0568 (5)
H10	0.6836	0.3538	0.2749	0.068*
C11	0.7373 (2)	0.4529 (2)	0.42864 (16)	0.0571 (5)
H11	0.7927	0.4404	0.5001	0.069*
C12	0.6654 (2)	0.58045 (19)	0.41173 (16)	0.0565 (5)
H12	0.6203	0.5953	0.3395	0.068*
C13	0.6493 (2)	0.69649 (19)	0.49042 (15)	0.0553 (5)
C14	0.5691 (2)	0.8153 (2)	0.45675 (16)	0.0598 (5)
H14	0.5296	0.8148	0.3819	0.072*
C15	0.5372 (2)	0.94110 (19)	0.52032 (17)	0.0615 (5)
H15	0.5700	0.9420	0.5953	0.074*
C16	1.1033 (8)	−0.0958 (10)	0.1987 (9)	0.107 (3)	0.601 (14)
H16A	1.1955	−0.1331	0.1804	0.161*	0.601 (14)
H16B	1.1315	−0.0755	0.2763	0.161*	0.601 (14)
H16C	1.0849	0.0017	0.1688	0.161*	0.601 (14)
C16B	1.0580 (15)	−0.0836 (14)	0.1310 (14)	0.108 (4)	0.399 (14)
H16D	1.1541	−0.1202	0.1178	0.163*	0.399 (14)
H16E	1.0972	−0.0015	0.1933	0.163*	0.399 (14)
H16F	0.9963	−0.0402	0.0687	0.163*	0.399 (14)
C17	0.9633 (11)	−0.3615 (10)	0.2214 (7)	0.088 (2)	0.601 (14)
H17A	0.9731	−0.3218	0.2948	0.131*	0.601 (14)
H17B	1.0645	−0.4011	0.2204	0.131*	0.601 (14)
H17C	0.8659	−0.4472	0.1923	0.131*	0.601 (14)
C17B	1.0301 (16)	−0.2869 (17)	0.2475 (10)	0.098 (3)	0.399 (14)
H17D	0.9490	−0.3541	0.2714	0.147*	0.399 (14)
H17E	1.0922	−0.1993	0.3042	0.147*	0.399 (14)
H17F	1.1081	−0.3493	0.2309	0.147*	0.399 (14)
C18	0.4767 (3)	−0.1584 (3)	0.0981 (2)	0.0916 (8)
H18A	0.4923	−0.1252	0.1735	0.137*
H18B	0.3854	−0.2500	0.0705	0.137*
H18C	0.4492	−0.0715	0.0578	0.137*
C19	0.8918 (2)	0.1632 (2)	0.46263 (15)	0.0626 (5)
H19A	0.8292	0.0680	0.4773	0.094*
H19B	0.9054	0.2514	0.5180	0.094*
H19C	1.0021	0.1448	0.4622	0.094*
C20	0.7194 (3)	0.6800 (2)	0.60621 (16)	0.0679 (6)
H20A	0.6872	0.7593	0.6495	0.102*
H20B	0.8416	0.6958	0.6268	0.102*
H20C	0.6751	0.5742	0.6177	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.1568 (18)	0.1489 (17)	0.0791 (12)	0.0517 (15)	0.0280 (12)	−0.0362 (12)
O4	0.1048 (13)	0.1320 (15)	0.0840 (12)	0.0324 (12)	−0.0108 (11)	−0.0218 (11)
C1	0.0601 (12)	0.0645 (12)	0.0738 (13)	0.0226 (10)	0.0223 (10)	−0.0076 (10)
C2	0.089 (4)	0.082 (5)	0.086 (3)	0.029 (4)	0.039 (3)	−0.002 (3)
C2B	0.076 (5)	0.073 (6)	0.080 (5)	0.028 (5)	0.027 (4)	−0.008 (5)
C3	0.090 (4)	0.080 (5)	0.063 (4)	0.023 (4)	0.021 (3)	−0.015 (3)
C3B	0.104 (6)	0.082 (7)	0.061 (6)	0.013 (6)	0.031 (5)	−0.006 (5)
C4	0.0812 (15)	0.0741 (14)	0.0661 (14)	0.0163 (12)	0.0094 (12)	−0.0019 (11)
C5	0.0632 (12)	0.0555 (11)	0.0696 (13)	0.0171 (9)	0.0166 (10)	0.0012 (10)
C6	0.0582 (11)	0.0458 (10)	0.0609 (11)	0.0182 (8)	0.0196 (9)	0.0038 (8)
C7	0.0556 (10)	0.0510 (10)	0.0621 (11)	0.0188 (8)	0.0174 (9)	0.0028 (9)
C8	0.0566 (11)	0.0526 (11)	0.0596 (11)	0.0200 (8)	0.0147 (9)	0.0017 (9)
C9	0.0484 (9)	0.0461 (10)	0.0610 (11)	0.0173 (8)	0.0153 (8)	0.0040 (8)
C10	0.0572 (10)	0.0496 (10)	0.0605 (11)	0.0190 (8)	0.0117 (9)	0.0016 (9)
C11	0.0507 (10)	0.0505 (10)	0.0663 (12)	0.0168 (8)	0.0117 (9)	0.0005 (9)
C12	0.0522 (10)	0.0463 (10)	0.0678 (12)	0.0151 (8)	0.0134 (9)	0.0019 (9)
C13	0.0476 (9)	0.0430 (10)	0.0741 (13)	0.0101 (8)	0.0188 (9)	0.0016 (9)
C14	0.0567 (11)	0.0481 (10)	0.0782 (13)	0.0172 (8)	0.0244 (10)	0.0042 (9)
C15	0.0564 (11)	0.0476 (11)	0.0820 (14)	0.0150 (8)	0.0238 (10)	0.0014 (10)
C16	0.064 (3)	0.116 (4)	0.132 (6)	0.006 (3)	0.037 (4)	−0.034 (5)
C16B	0.074 (6)	0.129 (6)	0.120 (9)	0.003 (5)	0.044 (6)	−0.013 (8)
C17	0.102 (5)	0.083 (5)	0.085 (4)	0.053 (3)	0.024 (3)	0.009 (3)
C17B	0.086 (7)	0.096 (8)	0.108 (7)	0.059 (6)	0.011 (5)	−0.005 (6)
C18	0.0608 (13)	0.0954 (17)	0.1093 (19)	0.0247 (12)	0.0148 (13)	−0.0083 (15)
C19	0.0645 (12)	0.0547 (11)	0.0668 (12)	0.0238 (9)	0.0135 (10)	0.0029 (9)
C20	0.0674 (12)	0.0597 (12)	0.0766 (14)	0.0200 (10)	0.0214 (11)	0.0020 (10)

Geometric parameters (Å, º)

O3—C3B	1.401 (12)	C10—H10	0.9500
O3—C3	1.419 (8)	C11—C12	1.348 (2)
O3—H3	0.8400	C11—H11	0.9500
O4—C4	1.219 (3)	C12—C13	1.437 (2)
C1—C17B	1.470 (12)	C12—H12	0.9500
C1—C2	1.500 (7)	C13—C14	1.357 (2)
C1—C6	1.533 (2)	C13—C20	1.505 (3)
C1—C16B	1.551 (11)	C14—C15	1.428 (2)
C1—C16	1.557 (7)	C14—H14	0.9500
C1—C2B	1.565 (10)	C15—C15^i	1.352 (3)
C1—C17	1.571 (8)	C15—H15	0.9500
C2—C3	1.509 (16)	C16—H16A	0.9800
C2—H2A	0.9900	C16—H16B	0.9800
C2—H2B	0.9900	C16—H16C	0.9800
C2B—C3B	1.49 (2)	C16B—H16D	0.9800
C2B—H2C	0.9900	C16B—H16E	0.9800
C2B—H2D	0.9900	C16B—H16F	0.9800
C3—C4	1.552 (9)	C17—H17A	0.9800
C3—H3A	1.0000	C17—H17B	0.9800
C3B—C4	1.465 (14)	C17—H17C	0.9800
C3B—H3B	1.0000	C17B—H17D	0.9800
C4—C5	1.466 (3)	C17B—H17E	0.9800
C5—C6	1.351 (2)	C17B—H17F	0.9800
C5—C18	1.516 (3)	C18—H18A	0.9800
C6—C7	1.462 (2)	C18—H18B	0.9800
C7—C8	1.338 (2)	C18—H18C	0.9800
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.446 (2)	C19—H19B	0.9800
C8—H8	0.9500	C19—H19C	0.9800
C9—C10	1.352 (2)	C20—H20A	0.9800
C9—C19	1.497 (3)	C20—H20B	0.9800
C10—C11	1.424 (2)	C20—H20C	0.9800
C3B—O3—H3	104.7	C7—C8—H8	116.4
C3—O3—H3	109.5	C9—C8—H8	116.4
C17B—C1—C2	126.7 (5)	C10—C9—C8	119.16 (17)
C17B—C1—C6	113.3 (5)	C10—C9—C19	122.26 (16)
C2—C1—C6	113.1 (3)	C8—C9—C19	118.57 (15)
C17B—C1—C16B	110.3 (6)	C9—C10—C11	127.21 (18)
C2—C1—C16B	80.4 (4)	C9—C10—H10	116.4
C6—C1—C16B	105.7 (5)	C11—C10—H10	116.4
C17B—C1—C16	78.5 (5)	C12—C11—C10	123.77 (18)
C2—C1—C16	107.4 (4)	C12—C11—H11	118.1
C6—C1—C16	110.9 (3)	C10—C11—H11	118.1
C17B—C1—C2B	109.2 (5)	C11—C12—C13	127.41 (19)
C6—C1—C2B	109.3 (4)	C11—C12—H12	116.3
C16B—C1—C2B	109.0 (5)	C13—C12—H12	116.3
C16—C1—C2B	131.3 (5)	C14—C13—C12	118.37 (18)
C2—C1—C17	110.8 (4)	C14—C13—C20	122.84 (17)
C6—C1—C17	107.5 (3)	C12—C13—C20	118.78 (16)
C16B—C1—C17	136.4 (5)	C13—C14—C15	127.81 (19)
C16—C1—C17	106.9 (4)	C13—C14—H14	116.1
C2B—C1—C17	85.7 (4)	C15—C14—H14	116.1
C1—C2—C3	110.9 (8)	C15^i—C15—C14	123.6 (2)
C1—C2—H2A	109.5	C15^i—C15—H15	118.2
C3—C2—H2A	109.5	C14—C15—H15	118.2
C1—C2—H2B	109.5	C1—C16—H16A	109.5
C3—C2—H2B	109.5	C1—C16—H16B	109.5
H2A—C2—H2B	108.0	C1—C16—H16C	109.5
C3B—C2B—C1	114.2 (11)	C1—C16B—H16D	109.5
C3B—C2B—H2C	108.7	C1—C16B—H16E	109.5
C1—C2B—H2C	108.7	H16D—C16B—H16E	109.5
C3B—C2B—H2D	108.7	C1—C16B—H16F	109.5
C1—C2B—H2D	108.7	H16D—C16B—H16F	109.5
H2C—C2B—H2D	107.6	H16E—C16B—H16F	109.5
O3—C3—C2	114.3 (8)	C1—C17—H17A	109.5
O3—C3—C4	107.9 (6)	C1—C17—H17B	109.5
C2—C3—C4	110.5 (7)	C1—C17—H17C	109.5
O3—C3—H3A	107.9	C1—C17B—H17D	109.5
C2—C3—H3A	107.9	C1—C17B—H17E	109.5
C4—C3—H3A	107.9	H17D—C17B—H17E	109.5
O3—C3B—C4	114.0 (10)	C1—C17B—H17F	109.5
O3—C3B—C2B	107.6 (13)	H17D—C17B—H17F	109.5
C4—C3B—C2B	104.7 (11)	H17E—C17B—H17F	109.5
O3—C3B—H3B	110.1	C5—C18—H18A	109.5
C4—C3B—H3B	110.1	C5—C18—H18B	109.5
C2B—C3B—H3B	110.1	H18A—C18—H18B	109.5
O4—C4—C3B	116.2 (5)	C5—C18—H18C	109.5
O4—C4—C5	122.6 (2)	H18A—C18—H18C	109.5
C3B—C4—C5	118.7 (5)	H18B—C18—H18C	109.5
O4—C4—C3	118.9 (3)	C9—C19—H19A	109.5
C5—C4—C3	117.5 (3)	C9—C19—H19B	109.5
C6—C5—C4	120.33 (18)	H19A—C19—H19B	109.5
C6—C5—C18	124.77 (18)	C9—C19—H19C	109.5
C4—C5—C18	114.86 (19)	H19A—C19—H19C	109.5
C5—C6—C7	122.15 (16)	H19B—C19—H19C	109.5
C5—C6—C1	122.43 (16)	C13—C20—H20A	109.5
C7—C6—C1	115.41 (16)	C13—C20—H20B	109.5
C8—C7—C6	125.40 (18)	H20A—C20—H20B	109.5
C8—C7—H7	117.3	C13—C20—H20C	109.5
C6—C7—H7	117.3	H20A—C20—H20C	109.5
C7—C8—C9	127.25 (18)	H20B—C20—H20C	109.5
C17B—C1—C2—C3	99.8 (12)	C3—C4—C5—C6	13.4 (6)
C6—C1—C2—C3	−49.0 (10)	O4—C4—C5—C18	3.5 (3)
C16B—C1—C2—C3	−152.0 (11)	C3B—C4—C5—C18	164.6 (8)
C16—C1—C2—C3	−171.7 (10)	C3—C4—C5—C18	−164.6 (5)
C2B—C1—C2—C3	39.5 (11)	C4—C5—C6—C7	175.87 (18)
C17—C1—C2—C3	71.8 (10)	C18—C5—C6—C7	−6.4 (3)
C17B—C1—C2B—C3B	167.8 (15)	C4—C5—C6—C1	−5.6 (3)
C2—C1—C2B—C3B	−59.8 (14)	C18—C5—C6—C1	172.1 (2)
C6—C1—C2B—C3B	43.3 (14)	C17B—C1—C6—C5	−129.2 (7)
C16B—C1—C2B—C3B	−71.7 (15)	C2—C1—C6—C5	23.9 (5)
C16—C1—C2B—C3B	−100.8 (14)	C16B—C1—C6—C5	109.9 (7)
C17—C1—C2B—C3B	150.4 (14)	C16—C1—C6—C5	144.6 (5)
C3B—O3—C3—C2	−61.8 (19)	C2B—C1—C6—C5	−7.2 (7)
C3B—O3—C3—C4	61.7 (16)	C17—C1—C6—C5	−98.8 (4)
C1—C2—C3—O3	178.0 (4)	C17B—C1—C6—C7	49.4 (7)
C1—C2—C3—C4	56.0 (12)	C2—C1—C6—C7	−157.5 (5)
C3—O3—C3B—C4	−76.3 (17)	C16B—C1—C6—C7	−71.4 (7)
C3—O3—C3B—C2B	39.4 (17)	C16—C1—C6—C7	−36.8 (6)
C1—C2B—C3B—O3	175.3 (7)	C2B—C1—C6—C7	171.4 (6)
C1—C2B—C3B—C4	−63.1 (17)	C17—C1—C6—C7	79.8 (4)
O3—C3B—C4—O4	−30.5 (14)	C5—C6—C7—C8	−50.4 (3)
C2B—C3B—C4—O4	−147.9 (9)	C1—C6—C7—C8	131.0 (2)
O3—C3B—C4—C5	167.1 (7)	C6—C7—C8—C9	−179.43 (17)
C2B—C3B—C4—C5	49.8 (15)	C7—C8—C9—C10	−176.63 (18)
O3—C3B—C4—C3	72.2 (16)	C7—C8—C9—C19	1.8 (3)
C2B—C3B—C4—C3	−45.2 (15)	C8—C9—C10—C11	174.64 (17)
O3—C3—C4—O4	27.2 (9)	C19—C9—C10—C11	−3.7 (3)
C2—C3—C4—O4	152.9 (7)	C9—C10—C11—C12	−177.12 (17)
O3—C3—C4—C3B	−64.5 (15)	C10—C11—C12—C13	174.24 (17)
C2—C3—C4—C3B	61.2 (16)	C11—C12—C13—C14	−178.72 (17)
O3—C3—C4—C5	−164.4 (4)	C11—C12—C13—C20	0.4 (3)
C2—C3—C4—C5	−38.6 (11)	C12—C13—C14—C15	179.16 (16)
O4—C4—C5—C6	−178.6 (2)	C20—C13—C14—C15	0.1 (3)
C3B—C4—C5—C6	−17.5 (8)	C13—C14—C15—C15^i	176.8 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	2.17	2.653 (3)	116
C10—H10···O4^ii	0.95	2.50	3.439 (3)	168

Symmetry code: (ii) −x+1, −y, −z.

(canth-100K)

Crystal data

C40H52O2	Z = 2
Mr = 564.82	F(000) = 616
Triclinic, P1	Dx = 1.102 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5068 (9) Å	Cell parameters from 1827 reflections
b = 14.2208 (16) Å	θ = 2.5–25.9°
c = 15.5262 (17) Å	µ = 0.07 mm^−1
α = 105.870 (2)°	T = 100 K
β = 95.227 (2)°	Block, dark red
γ = 106.512 (2)°	0.50 × 0.35 × 0.30 mm
V = 1702.9 (3) Å^3

Data collection

CCD area detector diffractometer	3448 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 26.4°, θmin = 1.4°
phi and ω scans	h = −9→10
9834 measured reflections	k = −17→15
6781 independent reflections	l = −19→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0443P)^2] where P = (Fo^2 + 2Fc^2)/3
6779 reflections	(Δ/σ)max < 0.001
419 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	−0.8012 (2)	−0.26005 (11)	−0.13973 (10)	0.0726 (5)
O4A	1.1199 (2)	1.70202 (11)	0.63776 (10)	0.0799 (6)
C1	−1.0614 (2)	−0.06461 (16)	−0.18228 (15)	0.0479 (6)
C2	−1.1363 (3)	−0.15226 (18)	−0.14428 (16)	0.0625 (7)
H2A	−1.1174	−0.1243	−0.0770	0.075*
H2B	−1.2583	−0.1802	−0.1668	0.075*
C3	−1.0634 (3)	−0.23881 (17)	−0.17056 (16)	0.0667 (7)
H3A	−1.1058	−0.2885	−0.1375	0.080*
H3B	−1.1014	−0.2758	−0.2366	0.080*
C4	−0.8778 (3)	−0.20167 (17)	−0.14990 (14)	0.0540 (6)
C5	−0.7878 (2)	−0.09463 (15)	−0.14542 (13)	0.0410 (5)
C6	−0.8708 (2)	−0.02990 (14)	−0.15827 (12)	0.0358 (5)
C7	−0.7841 (2)	0.07667 (14)	−0.15583 (12)	0.0347 (5)
H7	−0.8213	0.0979	−0.2047	0.042*
C8	−0.6578 (2)	0.14661 (14)	−0.09121 (12)	0.0332 (5)
H8	−0.6198	0.1247	−0.0430	0.040*
C9	−0.5736 (2)	0.25147 (14)	−0.08747 (12)	0.0312 (4)
C10	−0.4425 (2)	0.31095 (14)	−0.01932 (12)	0.0323 (5)
H10	−0.4166	0.2804	0.0251	0.039*
C11	−0.3382 (2)	0.41443 (13)	−0.00627 (12)	0.0316 (5)
H11	−0.3618	0.4480	−0.0486	0.038*
C12	−0.2078 (2)	0.46637 (13)	0.06347 (12)	0.0305 (4)
H12	−0.1911	0.4320	0.1064	0.037*
C13	−0.0911 (2)	0.56834 (13)	0.07995 (12)	0.0291 (4)
C14	0.0305 (2)	0.60802 (13)	0.15524 (12)	0.0305 (4)
H14	0.0293	0.5651	0.1927	0.037*
C15	0.1602 (2)	0.70548 (13)	0.18581 (13)	0.0330 (5)
H15	0.1700	0.7486	0.1481	0.040*
C16	−1.1275 (3)	0.02439 (18)	−0.14175 (18)	0.0742 (8)
H16A	−1.0921	0.0497	−0.0754	0.111*
H16B	−1.2496	−0.0002	−0.1569	0.111*
H16C	−1.0831	0.0806	−0.1670	0.111*
C17	−1.1139 (3)	−0.10177 (16)	−0.28701 (15)	0.0636 (7)
H17A	−1.0567	−0.0472	−0.3113	0.095*
H17B	−1.2348	−0.1179	−0.3032	0.095*
H17C	−1.0836	−0.1638	−0.3130	0.095*
C18	−0.6019 (2)	−0.06910 (16)	−0.13239 (15)	0.0592 (7)
H18A	−0.5540	−0.0102	−0.1537	0.089*
H18B	−0.5740	−0.1289	−0.1673	0.089*
H18C	−0.5563	−0.0515	−0.0676	0.089*
C19	−0.6332 (2)	0.28977 (14)	−0.16094 (12)	0.0382 (5)
H19A	−0.5733	0.3637	−0.1465	0.057*
H19B	−0.7530	0.2787	−0.1650	0.057*
H19C	−0.6120	0.2520	−0.2193	0.057*
C20	−0.1085 (2)	0.62449 (14)	0.01252 (12)	0.0362 (5)
H20A	−0.0224	0.6925	0.0328	0.054*
H20B	−0.2190	0.6331	0.0079	0.054*
H20C	−0.0956	0.5846	−0.0472	0.054*
C1A	1.4247 (3)	1.53115 (16)	0.67936 (14)	0.0441 (5)
C2A	1.5006 (4)	1.6155 (3)	0.6402 (3)	0.0464 (11)	0.610 (3)
H2E	1.4970	1.5859	0.5741	0.056*	0.610 (3)
H2F	1.6186	1.6520	0.6703	0.056*	0.610 (3)
C3A	1.3948 (3)	1.69507 (16)	0.65704 (17)	0.0683 (7)	0.610 (3)
H3E	1.4363	1.7432	0.7199	0.082*	0.610 (3)
H3F	1.4192	1.7365	0.6151	0.082*	0.610 (3)
C16A	1.5184 (4)	1.4463 (3)	0.6481 (3)	0.0493 (11)	0.610 (3)
H16D	1.6394	1.4805	0.6643	0.074*	0.610 (3)
H16E	1.4865	1.4130	0.5820	0.074*	0.610 (3)
H16F	1.4859	1.3941	0.6790	0.074*	0.610 (3)
C17A	1.4757 (4)	1.5686 (3)	0.7839 (2)	0.0445 (10)	0.610 (3)
H17D	1.4263	1.5119	0.8077	0.067*	0.610 (3)
H17E	1.4358	1.6266	0.8098	0.067*	0.610 (3)
H17F	1.5975	1.5909	0.8007	0.067*	0.610 (3)
C2B	1.4601 (7)	1.6548 (4)	0.7119 (4)	0.0507 (18)	0.390 (3)
H2G	1.4202	1.6735	0.7702	0.061*	0.390 (3)
H2H	1.5824	1.6888	0.7248	0.061*	0.390 (3)
C3B	1.3948 (3)	1.69507 (16)	0.65704 (17)	0.0683 (7)	0.390 (3)
H3G	1.4315	1.6782	0.5976	0.082*	0.390 (3)
H3H	1.4299	1.7711	0.6839	0.082*	0.390 (3)
C16B	1.4692 (6)	1.4996 (5)	0.5887 (4)	0.058 (2)	0.390 (3)
H16G	1.5906	1.5256	0.5941	0.087*	0.390 (3)
H16H	1.4166	1.5283	0.5479	0.087*	0.390 (3)
H16I	1.4301	1.4241	0.5638	0.087*	0.390 (3)
C17B	1.4986 (7)	1.5040 (5)	0.7492 (4)	0.0482 (17)	0.390 (3)
H17G	1.4814	1.4297	0.7288	0.072*	0.390 (3)
H17H	1.4476	1.5213	0.8030	0.072*	0.390 (3)
H17I	1.6184	1.5421	0.7648	0.072*	0.390 (3)
C4A	1.2116 (4)	1.65008 (17)	0.64499 (14)	0.0633 (7)
C5A	1.1370 (3)	1.54047 (15)	0.63926 (13)	0.0504 (6)
C6A	1.2354 (2)	1.48430 (15)	0.65311 (12)	0.0410 (5)
C7A	1.1655 (2)	1.37372 (14)	0.64427 (13)	0.0365 (5)
H7A	1.2004	1.3516	0.6930	0.044*
C8A	1.0566 (2)	1.30270 (14)	0.57259 (13)	0.0374 (5)
H8A	1.0267	1.3256	0.5234	0.045*
C9A	0.9792 (2)	1.19409 (14)	0.56191 (12)	0.0342 (5)
C10A	0.8587 (2)	1.13568 (14)	0.48766 (12)	0.0359 (5)
H10A	0.8424	1.1675	0.4427	0.043*
C11A	0.7536 (2)	1.03137 (14)	0.46974 (13)	0.0352 (5)
H11A	0.7710	0.9961	0.5118	0.042*
C12A	0.6308 (2)	0.98059 (14)	0.39571 (13)	0.0358 (5)
H12A	0.6214	1.0155	0.3523	0.043*
C13A	0.5129 (2)	0.87881 (14)	0.37642 (13)	0.0348 (5)
C14A	0.3971 (2)	0.83829 (14)	0.29755 (13)	0.0358 (5)
H14A	0.4023	0.8810	0.2596	0.043*
C15A	0.2696 (2)	0.74004 (14)	0.26506 (13)	0.0351 (5)
H15A	0.2612	0.6958	0.3018	0.042*
C18A	0.9494 (3)	1.50239 (17)	0.62192 (15)	0.0669 (7)
H18D	0.9068	1.4948	0.5587	0.100*
H18E	0.9091	1.5522	0.6633	0.100*
H18F	0.9101	1.4354	0.6325	0.100*
C19A	1.0299 (2)	1.15310 (14)	0.63478 (12)	0.0387 (5)
H19D	0.9738	1.0783	0.6164	0.058*
H19E	0.9983	1.1865	0.6915	0.058*
H19F	1.1510	1.1675	0.6443	0.058*
C20A	0.5221 (2)	0.82230 (14)	0.44446 (13)	0.0428 (5)
H20D	0.4281	0.7578	0.4260	0.064*
H20E	0.5171	0.8656	0.5046	0.064*
H20F	0.6271	0.8067	0.4472	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0933 (13)	0.0418 (10)	0.0737 (12)	0.0191 (10)	−0.0270 (9)	0.0204 (9)
O4A	0.1325 (16)	0.0372 (10)	0.0579 (11)	0.0249 (11)	−0.0244 (10)	0.0120 (8)
C1	0.0338 (12)	0.0367 (13)	0.0616 (16)	−0.0006 (10)	−0.0100 (10)	0.0159 (11)
C2	0.0413 (13)	0.0634 (17)	0.0697 (18)	−0.0076 (13)	−0.0051 (12)	0.0306 (14)
C3	0.0640 (16)	0.0423 (15)	0.0791 (19)	−0.0106 (13)	−0.0219 (13)	0.0362 (13)
C4	0.0671 (16)	0.0366 (13)	0.0461 (14)	0.0089 (12)	−0.0200 (11)	0.0119 (11)
C5	0.0403 (12)	0.0284 (12)	0.0425 (13)	0.0051 (10)	−0.0110 (9)	0.0050 (10)
C6	0.0334 (11)	0.0284 (11)	0.0355 (12)	0.0034 (9)	−0.0059 (9)	0.0050 (9)
C7	0.0287 (11)	0.0319 (12)	0.0401 (12)	0.0094 (9)	−0.0028 (9)	0.0093 (9)
C8	0.0276 (11)	0.0302 (11)	0.0392 (12)	0.0101 (9)	−0.0008 (9)	0.0081 (9)
C9	0.0244 (10)	0.0286 (11)	0.0354 (12)	0.0083 (9)	−0.0018 (9)	0.0046 (9)
C10	0.0288 (10)	0.0295 (11)	0.0365 (12)	0.0104 (9)	−0.0005 (9)	0.0080 (9)
C11	0.0288 (11)	0.0285 (11)	0.0344 (12)	0.0111 (9)	−0.0012 (9)	0.0052 (9)
C12	0.0291 (11)	0.0264 (11)	0.0333 (12)	0.0097 (9)	0.0021 (9)	0.0054 (9)
C13	0.0282 (10)	0.0234 (10)	0.0336 (12)	0.0103 (9)	0.0034 (9)	0.0045 (9)
C14	0.0294 (10)	0.0240 (11)	0.0359 (12)	0.0088 (9)	0.0032 (9)	0.0065 (9)
C15	0.0296 (11)	0.0253 (11)	0.0388 (12)	0.0068 (9)	0.0030 (9)	0.0052 (9)
C16	0.0312 (13)	0.0602 (17)	0.123 (2)	0.0119 (12)	0.0080 (14)	0.0215 (16)
C17	0.0545 (15)	0.0450 (15)	0.0753 (18)	−0.0095 (12)	−0.0243 (12)	0.0319 (13)
C18	0.0451 (14)	0.0394 (14)	0.0803 (18)	0.0177 (12)	−0.0129 (12)	0.0020 (12)
C19	0.0336 (11)	0.0285 (11)	0.0428 (13)	0.0066 (9)	−0.0069 (9)	0.0042 (9)
C20	0.0370 (11)	0.0281 (11)	0.0396 (12)	0.0109 (9)	0.0021 (9)	0.0057 (9)
C1A	0.0460 (13)	0.0328 (12)	0.0386 (13)	−0.0049 (10)	0.0031 (11)	0.0075 (10)
C2A	0.048 (2)	0.038 (2)	0.045 (3)	0.0007 (18)	0.0066 (19)	0.0144 (19)
C3A	0.095 (2)	0.0250 (13)	0.0630 (18)	−0.0088 (14)	0.0120 (15)	0.0100 (12)
C16A	0.039 (2)	0.042 (2)	0.067 (3)	0.0107 (18)	0.0140 (18)	0.018 (2)
C17A	0.036 (2)	0.039 (2)	0.042 (2)	−0.0013 (19)	−0.0073 (17)	0.005 (2)
C2B	0.041 (3)	0.044 (4)	0.052 (4)	−0.006 (3)	−0.008 (3)	0.017 (3)
C3B	0.095 (2)	0.0250 (13)	0.0630 (18)	−0.0088 (14)	0.0120 (15)	0.0100 (12)
C16B	0.038 (3)	0.059 (4)	0.069 (5)	0.001 (3)	0.004 (3)	0.025 (4)
C17B	0.038 (3)	0.041 (4)	0.051 (4)	0.001 (3)	−0.006 (3)	0.007 (3)
C4A	0.110 (2)	0.0294 (13)	0.0371 (14)	0.0141 (15)	−0.0208 (13)	0.0091 (11)
C5A	0.0617 (15)	0.0275 (12)	0.0466 (14)	0.0034 (11)	−0.0224 (11)	0.0093 (10)
C6A	0.0475 (13)	0.0296 (12)	0.0321 (12)	−0.0021 (10)	−0.0096 (9)	0.0086 (9)
C7A	0.0346 (11)	0.0275 (11)	0.0392 (13)	0.0022 (9)	−0.0058 (9)	0.0097 (10)
C8A	0.0393 (12)	0.0284 (12)	0.0384 (13)	0.0057 (10)	−0.0051 (10)	0.0107 (10)
C9A	0.0328 (11)	0.0249 (11)	0.0367 (12)	0.0038 (9)	−0.0016 (9)	0.0051 (9)
C10A	0.0388 (12)	0.0250 (11)	0.0382 (12)	0.0056 (10)	−0.0028 (9)	0.0091 (9)
C11A	0.0344 (11)	0.0238 (11)	0.0427 (13)	0.0077 (9)	−0.0003 (9)	0.0072 (9)
C12A	0.0343 (11)	0.0254 (11)	0.0390 (12)	0.0052 (9)	−0.0035 (9)	0.0046 (9)
C13A	0.0313 (11)	0.0251 (11)	0.0410 (13)	0.0062 (9)	0.0006 (9)	0.0041 (9)
C14A	0.0324 (11)	0.0274 (11)	0.0404 (13)	0.0065 (9)	0.0012 (9)	0.0044 (9)
C15A	0.0293 (11)	0.0260 (11)	0.0435 (13)	0.0053 (9)	0.0011 (9)	0.0062 (9)
C18A	0.0643 (16)	0.0425 (14)	0.0789 (19)	0.0169 (13)	−0.0281 (13)	0.0090 (13)
C19A	0.0356 (11)	0.0271 (11)	0.0434 (13)	0.0036 (9)	−0.0073 (9)	0.0069 (9)
C20A	0.0360 (12)	0.0308 (12)	0.0505 (14)	0.0007 (10)	−0.0044 (10)	0.0099 (10)

Geometric parameters (Å, º)

O4—C4	1.225 (2)	C1A—C17A	1.541 (4)
O4A—C4A	1.235 (3)	C1A—C2B	1.620 (6)
C1—C2	1.526 (3)	C1A—C16A	1.620 (4)
C1—C16	1.532 (3)	C2A—C3A	1.619 (4)
C1—C6	1.532 (3)	C2A—H2E	0.9900
C1—C17	1.545 (3)	C2A—H2F	0.9900
C2—C3	1.507 (3)	C3A—C4A	1.479 (3)
C2—H2A	0.9900	C3A—H3E	0.9900
C2—H2B	0.9900	C3A—H3F	0.9900
C3—C4	1.489 (3)	C16A—H16D	0.9800
C3—H3A	0.9900	C16A—H16E	0.9800
C3—H3B	0.9900	C16A—H16F	0.9800
C4—C5	1.476 (3)	C17A—H17D	0.9800
C5—C6	1.352 (2)	C17A—H17E	0.9800
C5—C18	1.500 (3)	C17A—H17F	0.9800
C6—C7	1.473 (2)	C2B—H2G	0.9900
C7—C8	1.342 (2)	C2B—H2H	0.9900
C7—H7	0.9500	C16B—H16G	0.9800
C8—C9	1.441 (2)	C16B—H16H	0.9800
C8—H8	0.9500	C16B—H16I	0.9800
C9—C10	1.356 (2)	C17B—H17G	0.9800
C9—C19	1.499 (2)	C17B—H17H	0.9800
C10—C11	1.434 (2)	C17B—H17I	0.9800
C10—H10	0.9500	C4A—C5A	1.481 (3)
C11—C12	1.351 (2)	C5A—C6A	1.351 (3)
C11—H11	0.9500	C5A—C18A	1.505 (3)
C12—C13	1.444 (2)	C6A—C7A	1.477 (2)
C12—H12	0.9500	C7A—C8A	1.335 (2)
C13—C14	1.358 (2)	C7A—H7A	0.9500
C13—C20	1.501 (2)	C8A—C9A	1.452 (2)
C14—C15	1.428 (2)	C8A—H8A	0.9500
C14—H14	0.9500	C9A—C10A	1.359 (2)
C15—C15A	1.350 (2)	C9A—C19A	1.490 (2)
C15—H15	0.9500	C10A—C11A	1.432 (2)
C16—H16A	0.9800	C10A—H10A	0.9500
C16—H16B	0.9800	C11A—C12A	1.354 (2)
C16—H16C	0.9800	C11A—H11A	0.9500
C17—H17A	0.9800	C12A—C13A	1.440 (2)
C17—H17B	0.9800	C12A—H12A	0.9500
C17—H17C	0.9800	C13A—C14A	1.369 (2)
C18—H18A	0.9800	C13A—C20A	1.501 (2)
C18—H18B	0.9800	C14A—C15A	1.427 (2)
C18—H18C	0.9800	C14A—H14A	0.9500
C19—H19A	0.9800	C15A—H15A	0.9500
C19—H19B	0.9800	C18A—H18D	0.9800
C19—H19C	0.9800	C18A—H18E	0.9800
C20—H20A	0.9800	C18A—H18F	0.9800
C20—H20B	0.9800	C19A—H19D	0.9800
C20—H20C	0.9800	C19A—H19E	0.9800
C1A—C17B	1.401 (6)	C19A—H19F	0.9800
C1A—C16B	1.475 (6)	C20A—H20D	0.9800
C1A—C2A	1.502 (4)	C20A—H20E	0.9800
C1A—C6A	1.525 (3)	C20A—H20F	0.9800
C2—C1—C16	108.47 (19)	C6A—C1A—C2B	104.7 (3)
C2—C1—C6	109.58 (16)	C17A—C1A—C2B	73.6 (3)
C16—C1—C6	111.10 (17)	C17B—C1A—C16A	63.9 (3)
C2—C1—C17	110.09 (17)	C16B—C1A—C16A	55.5 (2)
C16—C1—C17	108.96 (18)	C2A—C1A—C16A	105.6 (2)
C6—C1—C17	108.64 (17)	C6A—C1A—C16A	112.6 (2)
C3—C2—C1	112.97 (19)	C17A—C1A—C16A	102.7 (2)
C3—C2—H2A	109.0	C2B—C1A—C16A	141.2 (3)
C1—C2—H2A	109.0	C1A—C2A—C3A	108.0 (3)
C3—C2—H2B	109.0	C1A—C2A—H2E	110.1
C1—C2—H2B	109.0	C3A—C2A—H2E	110.1
H2A—C2—H2B	107.8	C1A—C2A—H2F	110.1
C4—C3—C2	112.67 (19)	C3A—C2A—H2F	110.1
C4—C3—H3A	109.1	H2E—C2A—H2F	108.4
C2—C3—H3A	109.1	C4A—C3A—C2A	117.2 (2)
C4—C3—H3B	109.1	C4A—C3A—H3E	108.0
C2—C3—H3B	109.1	C2A—C3A—H3E	108.0
H3A—C3—H3B	107.8	C4A—C3A—H3F	108.0
O4—C4—C5	120.6 (2)	C2A—C3A—H3F	108.0
O4—C4—C3	120.5 (2)	H3E—C3A—H3F	107.2
C5—C4—C3	118.87 (19)	C1A—C16A—H16D	109.5
C6—C5—C4	121.29 (18)	C1A—C16A—H16E	109.5
C6—C5—C18	124.62 (18)	C1A—C16A—H16F	109.5
C4—C5—C18	113.96 (18)	C1A—C17A—H17D	109.5
C5—C6—C7	122.41 (17)	C1A—C17A—H17E	109.5
C5—C6—C1	122.16 (18)	C1A—C17A—H17F	109.5
C7—C6—C1	115.32 (16)	C1A—C2B—H2G	107.7
C8—C7—C6	126.25 (17)	C1A—C2B—H2H	107.7
C8—C7—H7	116.9	H2G—C2B—H2H	107.1
C6—C7—H7	116.9	C1A—C16B—H16G	109.5
C7—C8—C9	126.72 (17)	C1A—C16B—H16H	109.5
C7—C8—H8	116.6	H16G—C16B—H16H	109.5
C9—C8—H8	116.6	C1A—C16B—H16I	109.5
C10—C9—C8	119.30 (16)	H16G—C16B—H16I	109.5
C10—C9—C19	122.47 (17)	H16H—C16B—H16I	109.5
C8—C9—C19	118.21 (16)	C1A—C17B—H17G	109.5
C9—C10—C11	127.76 (17)	C1A—C17B—H17H	109.5
C9—C10—H10	116.1	H17G—C17B—H17H	109.5
C11—C10—H10	116.1	C1A—C17B—H17I	109.5
C12—C11—C10	123.02 (17)	H17G—C17B—H17I	109.5
C12—C11—H11	118.5	H17H—C17B—H17I	109.5
C10—C11—H11	118.5	O4A—C4A—C3A	120.9 (2)
C11—C12—C13	127.16 (17)	O4A—C4A—C5A	119.5 (2)
C11—C12—H12	116.4	C3A—C4A—C5A	119.5 (2)
C13—C12—H12	116.4	C6A—C5A—C4A	120.4 (2)
C14—C13—C12	118.19 (16)	C6A—C5A—C18A	125.12 (19)
C14—C13—C20	123.24 (16)	C4A—C5A—C18A	114.4 (2)
C12—C13—C20	118.56 (16)	C5A—C6A—C7A	121.85 (18)
C13—C14—C15	128.83 (17)	C5A—C6A—C1A	122.18 (19)
C13—C14—H14	115.6	C7A—C6A—C1A	115.97 (17)
C15—C14—H14	115.6	C8A—C7A—C6A	124.57 (17)
C15A—C15—C14	123.97 (17)	C8A—C7A—H7A	117.7
C15A—C15—H15	118.0	C6A—C7A—H7A	117.7
C14—C15—H15	118.0	C7A—C8A—C9A	126.84 (17)
C1—C16—H16A	109.5	C7A—C8A—H8A	116.6
C1—C16—H16B	109.5	C9A—C8A—H8A	116.6
H16A—C16—H16B	109.5	C10A—C9A—C8A	118.27 (16)
C1—C16—H16C	109.5	C10A—C9A—C19A	123.10 (17)
H16A—C16—H16C	109.5	C8A—C9A—C19A	118.56 (16)
H16B—C16—H16C	109.5	C9A—C10A—C11A	127.14 (17)
C1—C17—H17A	109.5	C9A—C10A—H10A	116.4
C1—C17—H17B	109.5	C11A—C10A—H10A	116.4
H17A—C17—H17B	109.5	C12A—C11A—C10A	123.13 (18)
C1—C17—H17C	109.5	C12A—C11A—H11A	118.4
H17A—C17—H17C	109.5	C10A—C11A—H11A	118.4
H17B—C17—H17C	109.5	C11A—C12A—C13A	126.30 (18)
C5—C18—H18A	109.5	C11A—C12A—H12A	116.9
C5—C18—H18B	109.5	C13A—C12A—H12A	116.9
H18A—C18—H18B	109.5	C14A—C13A—C12A	118.76 (17)
C5—C18—H18C	109.5	C14A—C13A—C20A	123.00 (17)
H18A—C18—H18C	109.5	C12A—C13A—C20A	118.24 (16)
H18B—C18—H18C	109.5	C13A—C14A—C15A	128.23 (18)
C9—C19—H19A	109.5	C13A—C14A—H14A	115.9
C9—C19—H19B	109.5	C15A—C14A—H14A	115.9
H19A—C19—H19B	109.5	C15—C15A—C14A	124.59 (18)
C9—C19—H19C	109.5	C15—C15A—H15A	117.7
H19A—C19—H19C	109.5	C14A—C15A—H15A	117.7
H19B—C19—H19C	109.5	C5A—C18A—H18D	109.5
C13—C20—H20A	109.5	C5A—C18A—H18E	109.5
C13—C20—H20B	109.5	H18D—C18A—H18E	109.5
H20A—C20—H20B	109.5	C5A—C18A—H18F	109.5
C13—C20—H20C	109.5	H18D—C18A—H18F	109.5
H20A—C20—H20C	109.5	H18E—C18A—H18F	109.5
H20B—C20—H20C	109.5	C9A—C19A—H19D	109.5
C17B—C1A—C16B	117.9 (4)	C9A—C19A—H19E	109.5
C17B—C1A—C2A	128.5 (3)	H19D—C19A—H19E	109.5
C16B—C1A—C2A	62.9 (3)	C9A—C19A—H19F	109.5
C17B—C1A—C6A	115.4 (3)	H19D—C19A—H19F	109.5
C16B—C1A—C6A	99.5 (3)	H19E—C19A—H19F	109.5
C2A—C1A—C6A	114.8 (2)	C13A—C20A—H20D	109.5
C16B—C1A—C17A	149.5 (3)	C13A—C20A—H20E	109.5
C2A—C1A—C17A	111.0 (2)	H20D—C20A—H20E	109.5
C6A—C1A—C17A	109.4 (2)	C13A—C20A—H20F	109.5
C17B—C1A—C2B	109.3 (4)	H20D—C20A—H20F	109.5
C16B—C1A—C2B	108.9 (3)	H20E—C20A—H20F	109.5
C16—C1—C2—C3	−172.90 (18)	C16A—C1A—C2A—C3A	172.2 (2)
C6—C1—C2—C3	−51.5 (2)	C1A—C2A—C3A—C4A	−39.7 (4)
C17—C1—C2—C3	68.0 (2)	C2A—C3A—C4A—O4A	−164.8 (2)
C1—C2—C3—C4	51.4 (3)	C2A—C3A—C4A—C5A	13.7 (3)
C2—C3—C4—O4	157.0 (2)	O4A—C4A—C5A—C6A	−175.5 (2)
C2—C3—C4—C5	−25.3 (3)	C3A—C4A—C5A—C6A	6.0 (3)
O4—C4—C5—C6	178.69 (19)	O4A—C4A—C5A—C18A	1.7 (3)
C3—C4—C5—C6	1.0 (3)	C3A—C4A—C5A—C18A	−176.8 (2)
O4—C4—C5—C18	2.8 (3)	C4A—C5A—C6A—C7A	−177.49 (18)
C3—C4—C5—C18	−174.9 (2)	C18A—C5A—C6A—C7A	5.6 (3)
C4—C5—C6—C7	−178.86 (18)	C4A—C5A—C6A—C1A	2.9 (3)
C18—C5—C6—C7	−3.4 (3)	C18A—C5A—C6A—C1A	−174.0 (2)
C4—C5—C6—C1	−2.8 (3)	C17B—C1A—C6A—C5A	135.6 (4)
C18—C5—C6—C1	172.68 (19)	C16B—C1A—C6A—C5A	−97.2 (3)
C2—C1—C6—C5	27.7 (3)	C2A—C1A—C6A—C5A	−32.7 (3)
C16—C1—C6—C5	147.54 (19)	C17A—C1A—C6A—C5A	92.8 (3)
C17—C1—C6—C5	−92.6 (2)	C2B—C1A—C6A—C5A	15.4 (3)
C2—C1—C6—C7	−155.95 (18)	C16A—C1A—C6A—C5A	−153.7 (2)
C16—C1—C6—C7	−36.1 (2)	C17B—C1A—C6A—C7A	−44.1 (4)
C17—C1—C6—C7	83.7 (2)	C16B—C1A—C6A—C7A	83.2 (3)
C5—C6—C7—C8	−48.8 (3)	C2A—C1A—C6A—C7A	147.6 (2)
C1—C6—C7—C8	134.9 (2)	C17A—C1A—C6A—C7A	−86.8 (3)
C6—C7—C8—C9	−179.07 (17)	C2B—C1A—C6A—C7A	−164.2 (3)
C7—C8—C9—C10	−176.95 (18)	C16A—C1A—C6A—C7A	26.7 (3)
C7—C8—C9—C19	1.7 (3)	C5A—C6A—C7A—C8A	50.8 (3)
C8—C9—C10—C11	176.70 (17)	C1A—C6A—C7A—C8A	−129.6 (2)
C19—C9—C10—C11	−1.9 (3)	C6A—C7A—C8A—C9A	−177.41 (18)
C9—C10—C11—C12	−178.68 (18)	C7A—C8A—C9A—C10A	173.64 (19)
C10—C11—C12—C13	176.77 (16)	C7A—C8A—C9A—C19A	−3.6 (3)
C11—C12—C13—C14	178.91 (18)	C8A—C9A—C10A—C11A	−171.97 (18)
C11—C12—C13—C20	−2.0 (3)	C19A—C9A—C10A—C11A	5.2 (3)
C12—C13—C14—C15	179.39 (16)	C9A—C10A—C11A—C12A	176.7 (2)
C20—C13—C14—C15	0.4 (3)	C10A—C11A—C12A—C13A	−175.28 (18)
C13—C14—C15—C15A	175.93 (19)	C11A—C12A—C13A—C14A	−179.34 (19)
C17B—C1A—C2A—C3A	−118.9 (4)	C11A—C12A—C13A—C20A	1.1 (3)
C16B—C1A—C2A—C3A	135.7 (4)	C12A—C13A—C14A—C15A	−179.90 (18)
C6A—C1A—C2A—C3A	47.6 (3)	C20A—C13A—C14A—C15A	−0.4 (3)
C17A—C1A—C2A—C3A	−77.2 (3)	C14—C15—C15A—C14A	−178.35 (17)
C2B—C1A—C2A—C3A	−39.2 (3)	C13A—C14A—C15A—C15	−179.69 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O4^i	0.95	2.58	3.438 (2)	150

Symmetry code: (i) −x−1, −y, −z.

(canth-293)

Crystal data

C40H52O2	Z = 2
Mr = 564.82	F(000) = 616
Triclinic, P1	Dx = 1.060 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5919 (11) Å	Cell parameters from 1488 reflections
b = 14.3168 (18) Å	θ = 2.5–21.4°
c = 15.9405 (19) Å	µ = 0.06 mm^−1
α = 105.569 (2)°	T = 293 K
β = 96.118 (3)°	Block, dark red
γ = 107.024 (2)°	0.50 × 0.35 × 0.30 mm
V = 1769.2 (4) Å^3

Data collection

CCD area detector diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
phi and ω scans	h = −10→10
9285 measured reflections	k = −16→17
6162 independent reflections	l = −13→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 0.82	w = 1/[σ^2(Fo^2) + (0.0587P)^2] where P = (Fo^2 + 2Fc^2)/3
6162 reflections	(Δ/σ)max = 0.001
419 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.09 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O4	−0.7883 (3)	−0.24981 (16)	−0.13741 (15)	0.1373 (9)
O4A	1.1282 (3)	1.70598 (15)	0.63877 (14)	0.1228 (8)
C1	−1.0470 (3)	−0.0592 (2)	−0.1824 (2)	0.0852 (8)
C2	−1.1216 (4)	−0.1462 (3)	−0.1470 (2)	0.1199 (11)
H2A	−1.1068	−0.1180	−0.0817	0.144*
H2B	−1.2424	−0.1757	−0.1720	0.144*
C3	−1.0495 (4)	−0.2300 (2)	−0.1676 (2)	0.1192 (12)
H3A	−1.0899	−0.2705	−0.2313	0.143*
H3B	−1.0899	−0.2766	−0.1327	0.143*
C4	−0.8644 (4)	−0.1929 (2)	−0.14804 (19)	0.0969 (10)
C5	−0.7750 (3)	−0.0862 (2)	−0.14470 (16)	0.0759 (7)
C6	−0.8580 (3)	−0.02363 (18)	−0.15774 (15)	0.0659 (7)
C7	−0.7722 (3)	0.08266 (18)	−0.15511 (16)	0.0661 (7)
H7	−0.8082	0.1028	−0.2038	0.079*
C8	−0.6487 (3)	0.15360 (18)	−0.09098 (15)	0.0637 (7)
H8	−0.6129	0.1323	−0.0430	0.076*
C9	−0.5630 (3)	0.25871 (18)	−0.08576 (15)	0.0576 (6)
C10	−0.4352 (3)	0.31776 (17)	−0.01676 (15)	0.0613 (6)
H10	−0.4130	0.2874	0.0273	0.074*
C11	−0.3297 (3)	0.42098 (17)	−0.00270 (15)	0.0601 (6)
H11	−0.3515	0.4547	−0.0441	0.072*
C12	−0.2009 (3)	0.47230 (17)	0.06669 (15)	0.0579 (6)
H12	−0.1866	0.4374	0.1084	0.070*
C13	−0.0820 (3)	0.57396 (17)	0.08527 (15)	0.0559 (6)
C14	0.0377 (3)	0.61242 (17)	0.16005 (15)	0.0595 (6)
H14	0.0340	0.5691	0.1962	0.071*
C15	0.1687 (3)	0.70950 (17)	0.19157 (17)	0.0660 (7)
H15	0.1802	0.7528	0.1551	0.079*
C16	−1.1133 (4)	0.0278 (2)	−0.1437 (3)	0.1471 (14)
H16A	−1.0778	0.0530	−0.0789	0.221*
H16B	−1.2349	0.0021	−0.1596	0.221*
H16C	−1.0695	0.0842	−0.1679	0.221*
C17	−1.0985 (4)	−0.0953 (2)	−0.2844 (2)	0.1277 (12)
H17A	−1.0342	−0.0425	−0.3075	0.191*
H17B	−1.2172	−0.1068	−0.3014	0.191*
H17C	−1.0767	−0.1596	−0.3092	0.191*
C18	−0.5894 (3)	−0.0596 (2)	−0.1325 (2)	0.1129 (11)
H18A	−0.5432	−0.0011	−0.1538	0.169*
H18B	−0.5630	−0.1190	−0.1665	0.169*
H18C	−0.5412	−0.0414	−0.0694	0.169*
C19	−0.6170 (3)	0.29690 (17)	−0.15875 (15)	0.0703 (7)
H19A	−0.5568	0.3708	−0.1436	0.106*
H19B	−0.7367	0.2849	−0.1660	0.106*
H19C	−0.5928	0.2600	−0.2144	0.106*
C20	−0.0940 (3)	0.63200 (18)	0.02075 (15)	0.0732 (7)
H20A	−0.0090	0.7005	0.0436	0.110*
H20B	−0.2043	0.6389	0.0131	0.110*
H20C	−0.0766	0.5945	−0.0367	0.110*
C1A	1.4272 (3)	1.5346 (2)	0.67757 (19)	0.0706 (7)
C2A	1.4929 (7)	1.6216 (4)	0.6392 (5)	0.094 (2)	0.682 (9)
H2E	1.4788	1.5928	0.5740	0.113*	0.682 (9)
H2F	1.6131	1.6570	0.6644	0.113*	0.682 (9)
C3A	1.4008 (5)	1.6992 (2)	0.6604 (3)	0.1113 (11)	0.682 (9)
H3E	1.4430	1.7423	0.7235	0.134*	0.682 (9)
H3F	1.4282	1.7451	0.6235	0.134*	0.682 (9)
C16A	1.5112 (6)	1.4526 (4)	0.6447 (5)	0.103 (3)	0.682 (9)
H16D	1.6316	1.4866	0.6547	0.155*	0.682 (9)
H16E	1.4673	1.4167	0.5811	0.155*	0.682 (9)
H16F	1.4876	1.4029	0.6776	0.155*	0.682 (9)
C17A	1.4787 (6)	1.5730 (5)	0.7803 (4)	0.0867 (19)	0.682 (9)
H17D	1.4283	1.5170	0.8036	0.130*	0.682 (9)
H17E	1.4403	1.6309	0.8045	0.130*	0.682 (9)
H17F	1.6000	1.5954	0.7977	0.130*	0.682 (9)
C2B	1.4756 (16)	1.6527 (11)	0.7048 (13)	0.114 (6)	0.318 (9)
H2G	1.4631	1.6763	0.7672	0.136*	0.318 (9)
H2H	1.5957	1.6801	0.7049	0.136*	0.318 (9)
C3B	1.4008 (5)	1.6992 (2)	0.6604 (3)	0.1113 (11)	0.318 (9)
H3G	1.4350	1.6927	0.6024	0.134*	0.318 (9)
H3H	1.4361	1.7734	0.6943	0.134*	0.318 (9)
C16B	1.4764 (12)	1.4952 (11)	0.5887 (8)	0.110 (5)	0.318 (9)
H16G	1.5976	1.5209	0.5962	0.165*	0.318 (9)
H16H	1.4265	1.5197	0.5445	0.165*	0.318 (9)
H16I	1.4365	1.4198	0.5685	0.165*	0.318 (9)
C17B	1.5050 (13)	1.5056 (12)	0.7471 (10)	0.100 (5)	0.318 (9)
H17G	1.4852	1.4314	0.7265	0.150*	0.318 (9)
H17H	1.4575	1.5227	0.8000	0.150*	0.318 (9)
H17I	1.6248	1.5431	0.7618	0.150*	0.318 (9)
C4A	1.2176 (5)	1.6540 (2)	0.64563 (18)	0.0906 (9)
C5A	1.1424 (3)	1.54437 (19)	0.63916 (16)	0.0717 (7)
C6A	1.2389 (3)	1.48816 (18)	0.65204 (14)	0.0605 (6)
C7A	1.1673 (3)	1.37861 (17)	0.64433 (15)	0.0615 (6)
H7A	1.2009	1.3579	0.6932	0.074*
C8A	1.0597 (3)	1.30650 (17)	0.57479 (15)	0.0637 (7)
H8A	1.0299	1.3282	0.5259	0.076*
C9A	0.9822 (3)	1.19858 (17)	0.56451 (16)	0.0607 (6)
C10A	0.8635 (3)	1.13892 (18)	0.49124 (16)	0.0679 (7)
H10A	0.8475	1.1700	0.4468	0.081*
C11A	0.7596 (3)	1.03461 (18)	0.47310 (16)	0.0674 (7)
H11A	0.7772	0.9998	0.5143	0.081*
C12A	0.6379 (3)	0.98347 (17)	0.40030 (16)	0.0677 (7)
H12A	0.6288	1.0184	0.3580	0.081*
C13A	0.5199 (3)	0.88129 (18)	0.37977 (16)	0.0632 (7)
C14A	0.4060 (3)	0.84179 (18)	0.30252 (16)	0.0681 (7)
H14A	0.4128	0.8846	0.2657	0.082*
C15A	0.2766 (3)	0.74353 (17)	0.26950 (16)	0.0670 (7)
H15A	0.2665	0.6994	0.3052	0.080*
C18A	0.9547 (3)	1.5063 (2)	0.62221 (18)	0.0987 (9)
H18D	0.9104	1.4977	0.5603	0.148*
H18E	0.9167	1.5564	0.6621	0.148*
H18F	0.9151	1.4400	0.6332	0.148*
C19A	1.0313 (3)	1.15832 (17)	0.63675 (15)	0.0725 (7)
H19D	0.9728	1.0840	0.6193	0.109*
H19E	1.0017	1.1927	0.6916	0.109*
H19F	1.1515	1.1719	0.6467	0.109*
C20A	0.5282 (3)	0.82449 (18)	0.44586 (16)	0.0807 (8)
H20D	0.4333	0.7603	0.4273	0.121*
H20E	0.5250	0.8674	0.5045	0.121*
H20F	0.6318	0.8087	0.4489	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.160 (2)	0.0962 (17)	0.159 (2)	0.0501 (16)	−0.0196 (16)	0.0566 (15)
O4A	0.161 (2)	0.0803 (16)	0.1271 (18)	0.0460 (16)	−0.0067 (15)	0.0412 (13)
C1	0.0585 (18)	0.062 (2)	0.116 (3)	0.0020 (15)	−0.0073 (16)	0.0272 (17)
C2	0.078 (2)	0.106 (3)	0.160 (3)	−0.001 (2)	0.007 (2)	0.058 (3)
C3	0.104 (3)	0.081 (3)	0.158 (3)	0.001 (2)	−0.008 (2)	0.062 (2)
C4	0.110 (3)	0.078 (2)	0.099 (2)	0.029 (2)	−0.0132 (18)	0.0361 (19)
C5	0.0700 (19)	0.0564 (18)	0.084 (2)	0.0128 (15)	−0.0129 (14)	0.0143 (14)
C6	0.0571 (17)	0.0513 (17)	0.0715 (18)	0.0050 (14)	−0.0082 (12)	0.0136 (13)
C7	0.0535 (16)	0.0572 (17)	0.0706 (18)	0.0078 (14)	−0.0083 (13)	0.0127 (14)
C8	0.0523 (15)	0.0554 (17)	0.0739 (18)	0.0111 (14)	−0.0019 (13)	0.0183 (14)
C9	0.0439 (14)	0.0560 (17)	0.0612 (17)	0.0113 (13)	−0.0028 (12)	0.0108 (13)
C10	0.0497 (15)	0.0543 (17)	0.0695 (18)	0.0096 (13)	0.0016 (12)	0.0154 (13)
C11	0.0552 (15)	0.0536 (17)	0.0613 (17)	0.0142 (13)	−0.0009 (12)	0.0112 (13)
C12	0.0478 (14)	0.0504 (16)	0.0639 (17)	0.0100 (13)	0.0035 (12)	0.0094 (13)
C13	0.0496 (15)	0.0497 (16)	0.0592 (17)	0.0142 (13)	0.0068 (12)	0.0069 (13)
C14	0.0497 (15)	0.0496 (16)	0.0661 (17)	0.0082 (13)	0.0080 (13)	0.0081 (13)
C15	0.0590 (16)	0.0510 (17)	0.0708 (18)	0.0075 (14)	0.0059 (14)	0.0067 (13)
C16	0.063 (2)	0.098 (3)	0.257 (4)	0.025 (2)	0.023 (2)	0.024 (3)
C17	0.097 (2)	0.113 (3)	0.130 (3)	−0.015 (2)	−0.044 (2)	0.051 (2)
C18	0.081 (2)	0.089 (2)	0.144 (3)	0.0347 (19)	−0.0216 (19)	0.0081 (19)
C19	0.0612 (16)	0.0627 (17)	0.0740 (18)	0.0132 (13)	−0.0048 (13)	0.0160 (14)
C20	0.0735 (18)	0.0602 (18)	0.0781 (19)	0.0178 (14)	0.0084 (14)	0.0169 (14)
C1A	0.0596 (18)	0.0556 (19)	0.078 (2)	0.0001 (15)	0.0102 (15)	0.0140 (16)
C2A	0.095 (4)	0.071 (4)	0.087 (4)	−0.009 (3)	0.020 (4)	0.017 (3)
C3A	0.114 (3)	0.062 (2)	0.136 (3)	−0.004 (2)	0.017 (2)	0.036 (2)
C16A	0.072 (3)	0.089 (4)	0.143 (7)	0.024 (3)	0.034 (3)	0.025 (4)
C17A	0.068 (3)	0.082 (4)	0.079 (4)	−0.003 (3)	−0.009 (2)	0.015 (3)
C2B	0.073 (8)	0.087 (10)	0.142 (15)	−0.014 (6)	−0.029 (9)	0.039 (10)
C3B	0.114 (3)	0.062 (2)	0.136 (3)	−0.004 (2)	0.017 (2)	0.036 (2)
C16B	0.076 (7)	0.139 (13)	0.106 (10)	0.020 (7)	0.027 (6)	0.040 (8)
C17B	0.057 (6)	0.104 (11)	0.113 (12)	0.008 (7)	−0.009 (7)	0.024 (10)
C4A	0.118 (3)	0.063 (2)	0.080 (2)	0.021 (2)	−0.0061 (18)	0.0249 (16)
C5A	0.0706 (19)	0.0526 (18)	0.0767 (19)	0.0080 (15)	−0.0051 (14)	0.0174 (14)
C6A	0.0594 (16)	0.0497 (16)	0.0570 (16)	0.0055 (14)	0.0008 (12)	0.0104 (12)
C7A	0.0583 (16)	0.0470 (16)	0.0651 (17)	0.0048 (13)	0.0005 (13)	0.0137 (13)
C8A	0.0610 (16)	0.0502 (17)	0.0628 (17)	0.0032 (13)	−0.0048 (13)	0.0138 (13)
C9A	0.0556 (15)	0.0460 (16)	0.0664 (17)	0.0064 (13)	−0.0005 (13)	0.0119 (13)
C10A	0.0680 (17)	0.0474 (17)	0.0710 (19)	0.0053 (14)	−0.0062 (14)	0.0142 (13)
C11A	0.0640 (16)	0.0443 (16)	0.0775 (19)	0.0088 (14)	−0.0016 (14)	0.0093 (13)
C12A	0.0635 (17)	0.0454 (16)	0.0741 (19)	0.0066 (14)	−0.0027 (14)	0.0061 (13)
C13A	0.0524 (16)	0.0437 (16)	0.0763 (19)	0.0072 (13)	0.0042 (13)	0.0049 (14)
C14A	0.0581 (16)	0.0515 (17)	0.0765 (19)	0.0084 (14)	0.0036 (14)	0.0059 (14)
C15A	0.0528 (15)	0.0497 (17)	0.0774 (19)	0.0045 (13)	0.0047 (14)	0.0036 (13)
C18A	0.074 (2)	0.085 (2)	0.126 (3)	0.0244 (17)	−0.0067 (17)	0.0275 (18)
C19A	0.0695 (17)	0.0553 (17)	0.0766 (18)	0.0098 (14)	−0.0086 (13)	0.0164 (14)
C20A	0.0759 (19)	0.0544 (17)	0.090 (2)	0.0045 (14)	0.0002 (15)	0.0128 (15)

Geometric parameters (Å, º)

O4—C4	1.218 (3)	C1A—C2B	1.542 (15)
O4A—C4A	1.231 (3)	C1A—C17A	1.548 (6)
C1—C2	1.505 (3)	C1A—C16A	1.555 (5)
C1—C6	1.524 (3)	C2A—C3A	1.532 (7)
C1—C16	1.528 (4)	C2A—H2E	0.9900
C1—C17	1.539 (4)	C2A—H2F	0.9900
C2—C3	1.483 (4)	C3A—C4A	1.481 (4)
C2—H2A	0.9900	C3A—H3E	0.9900
C2—H2B	0.9900	C3A—H3F	0.9900
C3—C4	1.489 (4)	C16A—H16D	0.9800
C3—H3A	0.9900	C16A—H16E	0.9800
C3—H3B	0.9900	C16A—H16F	0.9800
C4—C5	1.480 (4)	C17A—H17D	0.9800
C5—C6	1.340 (3)	C17A—H17E	0.9800
C5—C18	1.504 (3)	C17A—H17F	0.9800
C6—C7	1.471 (3)	C2B—H2G	0.9900
C7—C8	1.335 (3)	C2B—H2H	0.9900
C7—H7	0.9500	C16B—H16G	0.9800
C8—C9	1.444 (3)	C16B—H16H	0.9800
C8—H8	0.9500	C16B—H16I	0.9800
C9—C10	1.353 (3)	C17B—H17G	0.9800
C9—C19	1.498 (3)	C17B—H17H	0.9800
C10—C11	1.432 (3)	C17B—H17I	0.9800
C10—H10	0.9500	C4A—C5A	1.482 (3)
C11—C12	1.347 (3)	C5A—C6A	1.349 (3)
C11—H11	0.9500	C5A—C18A	1.511 (3)
C12—C13	1.443 (3)	C6A—C7A	1.473 (3)
C12—H12	0.9500	C7A—C8A	1.326 (3)
C13—C14	1.355 (3)	C7A—H7A	0.9500
C13—C20	1.499 (3)	C8A—C9A	1.448 (3)
C14—C15	1.428 (3)	C8A—H8A	0.9500
C14—H14	0.9500	C9A—C10A	1.354 (3)
C15—C15A	1.344 (3)	C9A—C19A	1.494 (3)
C15—H15	0.9500	C10A—C11A	1.430 (3)
C16—H16A	0.9800	C10A—H10A	0.9500
C16—H16B	0.9800	C11A—C12A	1.346 (3)
C16—H16C	0.9800	C11A—H11A	0.9500
C17—H17A	0.9800	C12A—C13A	1.442 (3)
C17—H17B	0.9800	C12A—H12A	0.9500
C17—H17C	0.9800	C13A—C14A	1.356 (3)
C18—H18A	0.9800	C13A—C20A	1.501 (3)
C18—H18B	0.9800	C14A—C15A	1.433 (3)
C18—H18C	0.9800	C14A—H14A	0.9500
C19—H19A	0.9800	C15A—H15A	0.9500
C19—H19B	0.9800	C18A—H18D	0.9800
C19—H19C	0.9800	C18A—H18E	0.9800
C20—H20A	0.9800	C18A—H18F	0.9800
C20—H20B	0.9800	C19A—H19D	0.9800
C20—H20C	0.9800	C19A—H19E	0.9800
C1A—C17B	1.448 (11)	C19A—H19F	0.9800
C1A—C2A	1.521 (6)	C20A—H20D	0.9800
C1A—C6A	1.520 (3)	C20A—H20E	0.9800
C1A—C16B	1.530 (10)	C20A—H20F	0.9800
C2—C1—C6	109.9 (2)	C16B—C1A—C17A	147.0 (5)
C2—C1—C16	108.3 (3)	C2B—C1A—C17A	74.5 (6)
C6—C1—C16	111.5 (2)	C17B—C1A—C16A	65.1 (6)
C2—C1—C17	110.1 (2)	C2A—C1A—C16A	108.3 (3)
C6—C1—C17	108.1 (2)	C6A—C1A—C16A	111.6 (3)
C16—C1—C17	108.8 (3)	C2B—C1A—C16A	137.3 (7)
C3—C2—C1	114.5 (3)	C17A—C1A—C16A	105.8 (4)
C3—C2—H2A	108.6	C1A—C2A—C3A	111.0 (4)
C1—C2—H2A	108.6	C1A—C2A—H2E	109.4
C3—C2—H2B	108.6	C3A—C2A—H2E	109.4
C1—C2—H2B	108.6	C1A—C2A—H2F	109.4
H2A—C2—H2B	107.6	C3A—C2A—H2F	109.4
C2—C3—C4	113.7 (3)	H2E—C2A—H2F	108.0
C2—C3—H3A	108.8	C4A—C3A—C2A	115.4 (3)
C4—C3—H3A	108.8	C4A—C3A—H3E	108.4
C2—C3—H3B	108.8	C2A—C3A—H3E	108.4
C4—C3—H3B	108.8	C4A—C3A—H3F	108.4
H3A—C3—H3B	107.7	C2A—C3A—H3F	108.4
O4—C4—C5	120.6 (3)	H3E—C3A—H3F	107.5
O4—C4—C3	120.9 (3)	C1A—C16A—H16D	109.5
C5—C4—C3	118.5 (3)	C1A—C16A—H16E	109.5
C6—C5—C4	121.0 (3)	C1A—C16A—H16F	109.5
C6—C5—C18	124.8 (3)	C1A—C17A—H17D	109.5
C4—C5—C18	114.1 (2)	C1A—C17A—H17E	109.5
C5—C6—C7	122.1 (2)	C1A—C17A—H17F	109.5
C5—C6—C1	122.7 (2)	C1A—C2B—H2G	106.8
C7—C6—C1	115.1 (2)	C1A—C2B—H2H	106.8
C8—C7—C6	126.4 (2)	H2G—C2B—H2H	106.6
C8—C7—H7	116.8	C1A—C16B—H16G	109.5
C6—C7—H7	116.8	C1A—C16B—H16H	109.5
C7—C8—C9	127.9 (2)	H16G—C16B—H16H	109.5
C7—C8—H8	116.1	C1A—C16B—H16I	109.5
C9—C8—H8	116.1	H16G—C16B—H16I	109.5
C10—C9—C8	119.0 (2)	H16H—C16B—H16I	109.5
C10—C9—C19	122.7 (2)	C1A—C17B—H17G	109.5
C8—C9—C19	118.3 (2)	C1A—C17B—H17H	109.5
C9—C10—C11	127.3 (2)	H17G—C17B—H17H	109.5
C9—C10—H10	116.4	C1A—C17B—H17I	109.5
C11—C10—H10	116.4	H17G—C17B—H17I	109.5
C12—C11—C10	122.9 (2)	H17H—C17B—H17I	109.5
C12—C11—H11	118.6	O4A—C4A—C3A	121.1 (3)
C10—C11—H11	118.6	O4A—C4A—C5A	120.0 (3)
C11—C12—C13	127.8 (2)	C3A—C4A—C5A	118.9 (3)
C11—C12—H12	116.1	C6A—C5A—C4A	120.7 (3)
C13—C12—H12	116.1	C6A—C5A—C18A	125.0 (2)
C14—C13—C12	118.4 (2)	C4A—C5A—C18A	114.2 (2)
C14—C13—C20	122.7 (2)	C5A—C6A—C7A	121.8 (2)
C12—C13—C20	118.9 (2)	C5A—C6A—C1A	122.1 (2)
C13—C14—C15	128.5 (2)	C7A—C6A—C1A	116.1 (2)
C13—C14—H14	115.7	C8A—C7A—C6A	125.3 (2)
C15—C14—H14	115.7	C8A—C7A—H7A	117.4
C15A—C15—C14	124.2 (2)	C6A—C7A—H7A	117.4
C15A—C15—H15	117.9	C7A—C8A—C9A	127.7 (2)
C14—C15—H15	117.9	C7A—C8A—H8A	116.2
C1—C16—H16A	109.5	C9A—C8A—H8A	116.2
C1—C16—H16B	109.5	C10A—C9A—C8A	118.6 (2)
H16A—C16—H16B	109.5	C10A—C9A—C19A	122.5 (2)
C1—C16—H16C	109.5	C8A—C9A—C19A	118.8 (2)
H16A—C16—H16C	109.5	C9A—C10A—C11A	127.5 (2)
H16B—C16—H16C	109.5	C9A—C10A—H10A	116.3
C1—C17—H17A	109.5	C11A—C10A—H10A	116.3
C1—C17—H17B	109.5	C12A—C11A—C10A	123.0 (2)
H17A—C17—H17B	109.5	C12A—C11A—H11A	118.5
C1—C17—H17C	109.5	C10A—C11A—H11A	118.5
H17A—C17—H17C	109.5	C11A—C12A—C13A	126.8 (2)
H17B—C17—H17C	109.5	C11A—C12A—H12A	116.6
C5—C18—H18A	109.5	C13A—C12A—H12A	116.6
C5—C18—H18B	109.5	C14A—C13A—C12A	118.6 (2)
H18A—C18—H18B	109.5	C14A—C13A—C20A	123.3 (2)
C5—C18—H18C	109.5	C12A—C13A—C20A	118.1 (2)
H18A—C18—H18C	109.5	C13A—C14A—C15A	128.1 (2)
H18B—C18—H18C	109.5	C13A—C14A—H14A	116.0
C9—C19—H19A	109.5	C15A—C14A—H14A	116.0
C9—C19—H19B	109.5	C15—C15A—C14A	124.6 (2)
H19A—C19—H19B	109.5	C15—C15A—H15A	117.7
C9—C19—H19C	109.5	C14A—C15A—H15A	117.7
H19A—C19—H19C	109.5	C5A—C18A—H18D	109.5
H19B—C19—H19C	109.5	C5A—C18A—H18E	109.5
C13—C20—H20A	109.5	H18D—C18A—H18E	109.5
C13—C20—H20B	109.5	C5A—C18A—H18F	109.5
H20A—C20—H20B	109.5	H18D—C18A—H18F	109.5
C13—C20—H20C	109.5	H18E—C18A—H18F	109.5
H20A—C20—H20C	109.5	C9A—C19A—H19D	109.5
H20B—C20—H20C	109.5	C9A—C19A—H19E	109.5
C17B—C1A—C2A	131.3 (5)	H19D—C19A—H19E	109.5
C17B—C1A—C6A	115.6 (5)	C9A—C19A—H19F	109.5
C2A—C1A—C6A	111.5 (3)	H19D—C19A—H19F	109.5
C17B—C1A—C16B	112.0 (7)	H19E—C19A—H19F	109.5
C2A—C1A—C16B	69.0 (5)	C13A—C20A—H20D	109.5
C6A—C1A—C16B	101.3 (4)	C13A—C20A—H20E	109.5
C17B—C1A—C2B	109.8 (7)	H20D—C20A—H20E	109.5
C6A—C1A—C2B	108.3 (6)	C13A—C20A—H20F	109.5
C16B—C1A—C2B	109.3 (7)	H20D—C20A—H20F	109.5
C2A—C1A—C17A	111.0 (3)	H20E—C20A—H20F	109.5
C6A—C1A—C17A	108.5 (3)
C6—C1—C2—C3	−49.1 (4)	C16A—C1A—C2A—C3A	173.6 (5)
C16—C1—C2—C3	−171.1 (3)	C1A—C2A—C3A—C4A	−45.5 (7)
C17—C1—C2—C3	70.0 (3)	C2A—C3A—C4A—O4A	−161.8 (4)
C1—C2—C3—C4	48.0 (4)	C2A—C3A—C4A—C5A	18.2 (5)
C2—C3—C4—O4	159.2 (3)	O4A—C4A—C5A—C6A	−175.8 (3)
C2—C3—C4—C5	−22.7 (4)	C3A—C4A—C5A—C6A	4.1 (4)
O4—C4—C5—C6	178.9 (3)	O4A—C4A—C5A—C18A	1.2 (4)
C3—C4—C5—C6	0.9 (4)	C3A—C4A—C5A—C18A	−178.8 (3)
O4—C4—C5—C18	3.2 (4)	C4A—C5A—C6A—C7A	−178.8 (2)
C3—C4—C5—C18	−174.9 (3)	C18A—C5A—C6A—C7A	4.5 (4)
C4—C5—C6—C7	−179.8 (2)	C4A—C5A—C6A—C1A	2.7 (4)
C18—C5—C6—C7	−4.5 (4)	C18A—C5A—C6A—C1A	−174.0 (2)
C4—C5—C6—C1	−4.0 (4)	C17B—C1A—C6A—C5A	136.0 (8)
C18—C5—C6—C1	171.3 (3)	C2A—C1A—C6A—C5A	−30.9 (4)
C2—C1—C6—C5	27.5 (4)	C16B—C1A—C6A—C5A	−102.6 (7)
C16—C1—C6—C5	147.6 (3)	C2B—C1A—C6A—C5A	12.3 (9)
C17—C1—C6—C5	−92.8 (3)	C17A—C1A—C6A—C5A	91.6 (4)
C2—C1—C6—C7	−156.4 (3)	C16A—C1A—C6A—C5A	−152.2 (4)
C16—C1—C6—C7	−36.3 (3)	C17B—C1A—C6A—C7A	−42.5 (8)
C17—C1—C6—C7	83.3 (3)	C2A—C1A—C6A—C7A	150.5 (3)
C5—C6—C7—C8	−50.4 (4)	C16B—C1A—C6A—C7A	78.9 (7)
C1—C6—C7—C8	133.4 (3)	C2B—C1A—C6A—C7A	−166.2 (8)
C6—C7—C8—C9	−179.3 (2)	C17A—C1A—C6A—C7A	−86.9 (4)
C7—C8—C9—C10	−177.1 (2)	C16A—C1A—C6A—C7A	29.3 (4)
C7—C8—C9—C19	1.3 (4)	C5A—C6A—C7A—C8A	53.4 (3)
C8—C9—C10—C11	176.2 (2)	C1A—C6A—C7A—C8A	−128.0 (3)
C19—C9—C10—C11	−2.1 (4)	C6A—C7A—C8A—C9A	−178.3 (2)
C9—C10—C11—C12	−177.3 (2)	C7A—C8A—C9A—C10A	174.1 (2)
C10—C11—C12—C13	176.7 (2)	C7A—C8A—C9A—C19A	−3.5 (4)
C11—C12—C13—C14	179.0 (2)	C8A—C9A—C10A—C11A	−172.5 (2)
C11—C12—C13—C20	−1.9 (3)	C19A—C9A—C10A—C11A	5.0 (4)
C12—C13—C14—C15	179.2 (2)	C9A—C10A—C11A—C12A	176.0 (2)
C20—C13—C14—C15	0.1 (4)	C10A—C11A—C12A—C13A	−175.2 (2)
C13—C14—C15—C15A	176.1 (2)	C11A—C12A—C13A—C14A	−179.6 (2)
C17B—C1A—C2A—C3A	−113.8 (11)	C11A—C12A—C13A—C20A	1.2 (4)
C6A—C1A—C2A—C3A	50.5 (6)	C12A—C13A—C14A—C15A	−179.0 (2)
C16B—C1A—C2A—C3A	144.8 (8)	C20A—C13A—C14A—C15A	0.2 (4)
C2B—C1A—C2A—C3A	−43.0 (7)	C14—C15—C15A—C14A	−178.5 (2)
C17A—C1A—C2A—C3A	−70.6 (6)	C13A—C14A—C15A—C15	−179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O4^i	0.95	2.60	3.471 (3)	152

Symmetry code: (i) −x−1, −y, −z.

(zea)

Crystal data

C40H56O2·(3H2O)	F(000) = 1368
Mr = 622.90	Dx = 1.046 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 2203 reflections
a = 49.670 (15) Å	θ = 2.6–25.3°
b = 13.181 (4) Å	µ = 0.07 mm^−1
c = 6.0588 (19) Å	T = 100 K
β = 94.425 (6)°	Plate, orange
V = 3955 (2) Å^3	0.90 × 0.15 × 0.05 mm
Z = 4

Data collection

CCD area detector diffractometer	3489 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan SADABS	h = −56→58
Tmin = 0.807, Tmax = 1.000	k = −15→15
13818 measured reflections	l = −7→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 0.0665P] where P = (Fo^2 + 2Fc^2)/3
3489 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O3	0.49569 (3)	0.59866 (12)	1.0311 (2)	0.0439 (4)
H3O	0.4972	0.6060	1.1659	0.066*
C1	0.44598 (4)	0.80435 (14)	0.8482 (3)	0.0317 (5)
C2	0.47091 (4)	0.75360 (16)	0.9660 (4)	0.0372 (5)
H2A	0.4870	0.7798	0.9052	0.045*
H2B	0.4719	0.7710	1.1220	0.045*
C3	0.47038 (4)	0.64075 (15)	0.9425 (3)	0.0352 (5)
H3	0.4679	0.6240	0.7847	0.042*
C4	0.44678 (4)	0.59864 (14)	1.0556 (3)	0.0321 (5)
H4A	0.4508	0.6019	1.2147	0.039*
H4B	0.4443	0.5279	1.0151	0.039*
C5	0.42081 (4)	0.65563 (14)	0.9948 (3)	0.0299 (5)
C6	0.42044 (4)	0.74649 (14)	0.8974 (3)	0.0273 (5)
C7	0.39466 (4)	0.79947 (14)	0.8268 (3)	0.0306 (5)
H7	0.3895	0.8539	0.9117	0.037*
C8	0.37855 (4)	0.77386 (15)	0.6505 (3)	0.0322 (5)
H8	0.3834	0.7163	0.5743	0.039*
C9	0.35424 (4)	0.82534 (14)	0.5632 (3)	0.0281 (5)
C10	0.34115 (4)	0.78971 (15)	0.3747 (3)	0.0328 (5)
H10	0.3488	0.7329	0.3132	0.039*
C11	0.31715 (4)	0.82774 (15)	0.2573 (3)	0.0300 (5)
H11	0.3080	0.8813	0.3183	0.036*
C12	0.30723 (4)	0.78887 (15)	0.0615 (3)	0.0318 (5)
H12	0.3170	0.7357	0.0058	0.038*
C13	0.28336 (4)	0.81985 (14)	−0.0714 (3)	0.0287 (5)
C14	0.27623 (4)	0.76757 (15)	−0.2601 (3)	0.0323 (5)
H14	0.2882	0.7170	−0.2962	0.039*
C15	0.25288 (4)	0.77958 (15)	−0.4105 (3)	0.0299 (4)
H15	0.2409	0.8315	−0.3833	0.036*
C16	0.44829 (4)	0.80890 (16)	0.5979 (3)	0.0396 (5)
H16A	0.4320	0.8369	0.5270	0.059*
H16B	0.4510	0.7417	0.5425	0.059*
H16C	0.4633	0.8509	0.5673	0.059*
C17	0.44485 (5)	0.91283 (15)	0.9372 (4)	0.0417 (6)
H17A	0.4412	0.9111	1.0905	0.063*
H17B	0.4308	0.9497	0.8545	0.063*
H17C	0.4619	0.9458	0.9225	0.063*
C18	0.39582 (4)	0.60307 (16)	1.0624 (4)	0.0433 (6)
H18A	0.3804	0.6462	1.0304	0.065*
H18B	0.3978	0.5888	1.2182	0.065*
H18C	0.3933	0.5407	0.9816	0.065*
C19	0.34552 (4)	0.91735 (14)	0.6819 (3)	0.0312 (5)
H19A	0.3285	0.9408	0.6141	0.047*
H19B	0.3588	0.9697	0.6739	0.047*
H19C	0.3436	0.9008	0.8341	0.047*
C20	0.26757 (4)	0.90806 (14)	0.0063 (3)	0.0324 (5)
H20A	0.2526	0.9216	−0.0991	0.049*
H20B	0.2790	0.9668	0.0206	0.049*
H20C	0.2610	0.8923	0.1473	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0356 (8)	0.0576 (10)	0.0376 (9)	0.0156 (7)	−0.0029 (7)	0.0134 (8)
C1	0.0326 (11)	0.0303 (11)	0.0316 (11)	0.0040 (9)	−0.0011 (9)	0.0036 (8)
C2	0.0325 (12)	0.0386 (12)	0.0400 (13)	0.0021 (9)	−0.0008 (10)	0.0035 (10)
C3	0.0335 (12)	0.0378 (12)	0.0336 (12)	0.0099 (9)	−0.0018 (9)	0.0060 (9)
C4	0.0386 (12)	0.0269 (10)	0.0307 (11)	0.0053 (9)	0.0021 (9)	0.0012 (8)
C5	0.0332 (11)	0.0307 (11)	0.0261 (11)	0.0036 (9)	0.0039 (9)	−0.0054 (8)
C6	0.0304 (11)	0.0299 (11)	0.0211 (10)	0.0054 (8)	−0.0004 (8)	−0.0035 (8)
C7	0.0344 (11)	0.0285 (11)	0.0290 (11)	0.0067 (9)	0.0041 (9)	−0.0037 (8)
C8	0.0346 (12)	0.0301 (11)	0.0317 (11)	0.0059 (9)	0.0014 (9)	−0.0056 (9)
C9	0.0268 (10)	0.0295 (11)	0.0282 (11)	0.0009 (8)	0.0039 (9)	0.0004 (8)
C10	0.0295 (11)	0.0355 (11)	0.0332 (12)	0.0036 (9)	0.0022 (9)	−0.0042 (9)
C11	0.0294 (11)	0.0304 (11)	0.0304 (11)	0.0001 (9)	0.0037 (9)	−0.0013 (9)
C12	0.0286 (10)	0.0332 (11)	0.0336 (12)	0.0007 (9)	0.0021 (9)	−0.0018 (9)
C13	0.0289 (10)	0.0291 (11)	0.0284 (11)	−0.0060 (8)	0.0037 (8)	0.0015 (9)
C14	0.0275 (11)	0.0348 (11)	0.0348 (12)	−0.0023 (9)	0.0043 (9)	−0.0015 (9)
C15	0.0257 (10)	0.0313 (11)	0.0326 (11)	−0.0042 (9)	0.0021 (9)	−0.0009 (8)
C16	0.0438 (13)	0.0377 (12)	0.0380 (13)	0.0052 (10)	0.0072 (10)	0.0056 (10)
C17	0.0508 (14)	0.0325 (12)	0.0413 (13)	−0.0009 (10)	0.0000 (11)	0.0021 (10)
C18	0.0437 (13)	0.0389 (13)	0.0488 (14)	0.0047 (10)	0.0130 (11)	0.0013 (10)
C19	0.0308 (11)	0.0328 (11)	0.0294 (11)	0.0046 (9)	−0.0009 (9)	0.0012 (9)
C20	0.0337 (11)	0.0323 (11)	0.0306 (11)	−0.0015 (9)	−0.0018 (9)	0.0016 (9)

Geometric parameters (Å, º)

O3—C3	1.440 (2)	C11—C12	1.350 (3)
O3—H3O	0.8200	C11—H11	0.9300
C1—C6	1.529 (3)	C12—C13	1.440 (3)
C1—C16	1.531 (3)	C12—H12	0.9300
C1—C17	1.531 (3)	C13—C14	1.358 (3)
C1—C2	1.534 (3)	C13—C20	1.499 (3)
C2—C3	1.494 (3)	C14—C15	1.427 (3)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C15^i	1.349 (4)
C3—C4	1.509 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—H16A	0.9600
C4—C5	1.513 (3)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700	C17—H17A	0.9600
C5—C6	1.335 (3)	C17—H17B	0.9600
C5—C18	1.506 (3)	C17—H17C	0.9600
C6—C7	1.492 (3)	C18—H18A	0.9600
C7—C8	1.328 (3)	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600
C8—C9	1.449 (3)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—C10	1.354 (3)	C19—H19C	0.9600
C9—C19	1.491 (3)	C20—H20A	0.9600
C10—C11	1.431 (3)	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C3—O3—H3O	109.5	C12—C11—H11	118.7
C6—C1—C16	109.86 (16)	C10—C11—H11	118.7
C6—C1—C17	110.10 (17)	C11—C12—C13	127.79 (19)
C16—C1—C17	108.67 (16)	C11—C12—H12	116.1
C6—C1—C2	110.09 (16)	C13—C12—H12	116.1
C16—C1—C2	111.01 (17)	C14—C13—C12	118.49 (18)
C17—C1—C2	107.07 (16)	C14—C13—C20	123.31 (18)
C3—C2—C1	112.46 (17)	C12—C13—C20	118.20 (17)
C3—C2—H2A	109.1	C13—C14—C15	128.87 (19)
C1—C2—H2A	109.1	C13—C14—H14	115.6
C3—C2—H2B	109.1	C15—C14—H14	115.6
C1—C2—H2B	109.1	C15^i—C15—C14	124.1 (2)
H2A—C2—H2B	107.8	C15^i—C15—H15	117.9
O3—C3—C2	109.86 (17)	C14—C15—H15	117.9
O3—C3—C4	112.08 (16)	C1—C16—H16A	109.5
C2—C3—C4	109.35 (17)	C1—C16—H16B	109.5
O3—C3—H3	108.5	H16A—C16—H16B	109.5
C2—C3—H3	108.5	C1—C16—H16C	109.5
C4—C3—H3	108.5	H16A—C16—H16C	109.5
C3—C4—C5	112.60 (16)	H16B—C16—H16C	109.5
C3—C4—H4A	109.1	C1—C17—H17A	109.5
C5—C4—H4A	109.1	C1—C17—H17B	109.5
C3—C4—H4B	109.1	H17A—C17—H17B	109.5
C5—C4—H4B	109.1	C1—C17—H17C	109.5
H4A—C4—H4B	107.8	H17A—C17—H17C	109.5
C6—C5—C18	123.34 (18)	H17B—C17—H17C	109.5
C6—C5—C4	122.38 (17)	C5—C18—H18A	109.5
C18—C5—C4	114.23 (17)	C5—C18—H18B	109.5
C5—C6—C7	121.95 (17)	H18A—C18—H18B	109.5
C5—C6—C1	123.40 (17)	C5—C18—H18C	109.5
C7—C6—C1	114.65 (16)	H18A—C18—H18C	109.5
C8—C7—C6	124.22 (17)	H18B—C18—H18C	109.5
C8—C7—H7	117.9	C9—C19—H19A	109.5
C6—C7—H7	117.9	C9—C19—H19B	109.5
C7—C8—C9	127.44 (18)	H19A—C19—H19B	109.5
C7—C8—H8	116.3	C9—C19—H19C	109.5
C9—C8—H8	116.3	H19A—C19—H19C	109.5
C10—C9—C8	118.53 (18)	H19B—C19—H19C	109.5
C10—C9—C19	123.41 (17)	C13—C20—H20A	109.5
C8—C9—C19	118.02 (16)	C13—C20—H20B	109.5
C9—C10—C11	128.68 (19)	H20A—C20—H20B	109.5
C9—C10—H10	115.7	C13—C20—H20C	109.5
C11—C10—H10	115.7	H20A—C20—H20C	109.5
C12—C11—C10	122.50 (19)	H20B—C20—H20C	109.5
C6—C1—C2—C3	44.6 (2)	C17—C1—C6—C7	51.3 (2)
C16—C1—C2—C3	−77.2 (2)	C2—C1—C6—C7	169.14 (16)
C17—C1—C2—C3	164.29 (18)	C5—C6—C7—C8	−74.9 (3)
C1—C2—C3—O3	172.61 (16)	C1—C6—C7—C8	104.9 (2)
C1—C2—C3—C4	−64.0 (2)	C6—C7—C8—C9	−175.62 (19)
O3—C3—C4—C5	169.44 (16)	C7—C8—C9—C10	177.1 (2)
C2—C3—C4—C5	47.4 (2)	C7—C8—C9—C19	−0.7 (3)
C3—C4—C5—C6	−15.3 (3)	C8—C9—C10—C11	−179.54 (19)
C3—C4—C5—C18	167.20 (17)	C19—C9—C10—C11	−1.9 (3)
C18—C5—C6—C7	−6.2 (3)	C9—C10—C11—C12	175.3 (2)
C4—C5—C6—C7	176.53 (17)	C10—C11—C12—C13	179.66 (19)
C18—C5—C6—C1	174.12 (18)	C11—C12—C13—C14	−177.20 (19)
C4—C5—C6—C1	−3.2 (3)	C11—C12—C13—C20	2.5 (3)
C16—C1—C6—C5	111.4 (2)	C12—C13—C14—C15	175.84 (18)
C17—C1—C6—C5	−128.96 (19)	C20—C13—C14—C15	−3.9 (3)
C2—C1—C6—C5	−11.1 (3)	C13—C14—C15—C15^i	−177.1 (2)
C16—C1—C6—C7	−68.3 (2)

Symmetry code: (i) −x+1/2, −y+3/2, −z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O3^ii	0.82	1.85	2.654 (3)	169

Symmetry code: (ii) −x+1, y, −z+5/2.