16α,17α-Epoxy-20-oxopregn-5-ene-3β,21-diyl di­acetate

The title compound, C₂₅H₃₄O₆, has a 3β,21-configuration, with the epoxy O atom at 16α,17α. Rings A and C have chair conformations which are slightly flattened. Because of the presence of a double bond, ring B assumes an 8β,9α-half chair conformation. Ring D has a conformation close to a 14α-envelope. Cohesion of the crystal can be attributed to van der Waals interactions and weak C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.154
• Data-to-parameter ratio = 9.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           72.59
         From the CIF: _reflns_number_total               2624
         Count of symmetry unique reflns         2709
         Completeness (_total/calc)             96.86%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          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.

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek,1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson,1976); software used to prepare material for publication: SHELXL97.

16α,17α-Epoxy-20-oxopregn-5-ene-3β,21-diyl diacetate

Crystal data

C25H34O6	F(000) = 928
Mr = 430.52	Dx = 1.226 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.988 (1) Å	θ = 18.8–26.5°
b = 10.668 (1) Å	µ = 0.70 mm^−1
c = 36.511 (3) Å	T = 293 K
V = 2332.4 (5) Å^3	Prism, colourless
Z = 4	0.49 × 0.14 × 0.13 mm

Data collection

Enraf-Nonius MACH-3 diffractometer	1949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 72.6°, θmin = 4.3°
profile data from ω–2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.887, Tmax = 0.913	l = 0→45
6910 measured reflections	3 standard reflections every 200 min
2624 independent reflections	intensity decay: 37.0%

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) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0947P)^2 + 0.2153P] where P = (Fo^2 + 2Fc^2)/3
2624 reflections	(Δ/σ)max = 0.005
284 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. All H atoms were refined as riding on their parent atoms using SHELXL97 (Sheldrick, 1997) defaults except for H9 and H14 wich had their coordinates freely refined with U_iso=1.2 U_eq of the C atoms. The absolute configuration was not determined from the X-ray data but it was known from the synthetic route.

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	0.9601 (5)	0.5862 (2)	1.05898 (6)	0.0832 (7)
C9	0.7035 (5)	0.4140 (3)	0.91588 (8)	0.0626 (7)
H9	0.5961	0.3601	0.9286	0.075*
C14	0.7520 (5)	0.2534 (3)	0.86727 (8)	0.0650 (7)
H14	0.6263	0.2118	0.8794	0.078*
O16	0.4821 (5)	0.1268 (2)	0.82412 (8)	0.0920 (8)
C13	0.6466 (6)	0.3386 (3)	0.83769 (9)	0.0684 (8)
C10	0.8151 (5)	0.4959 (2)	0.94582 (9)	0.0617 (7)
C8	0.8724 (5)	0.3255 (2)	0.89719 (8)	0.0617 (7)
H8	0.9904	0.3762	0.8859	0.074*
C12	0.4665 (6)	0.4156 (4)	0.85634 (11)	0.0861 (10)
H12A	0.3509	0.3605	0.8656	0.103*
H12B	0.3988	0.4721	0.8387	0.103*
C11	0.5673 (6)	0.4918 (3)	0.88811 (10)	0.0849 (10)
H11A	0.4470	0.5335	0.9011	0.102*
H11B	0.6633	0.5562	0.8780	0.102*
C5	0.9701 (5)	0.4177 (3)	0.96953 (8)	0.0647 (7)
O21	0.3036 (6)	0.2244 (3)	0.71452 (8)	0.1050 (9)
C7	0.9779 (7)	0.2387 (3)	0.92525 (8)	0.0787 (9)
H7A	0.8755	0.1704	0.9304	0.094*
H7B	1.1129	0.2028	0.9150	0.094*
C6	1.0338 (7)	0.3027 (3)	0.95990 (9)	0.0781 (9)
H6	1.1216	0.2587	0.9765	0.094*
C3	0.8562 (6)	0.5251 (3)	1.02747 (9)	0.0753 (9)
H3	0.7628	0.4553	1.0359	0.090*
O20	0.4140 (6)	0.3863 (2)	0.76733 (9)	0.1191 (12)
C4	1.0493 (6)	0.4747 (3)	1.00475 (9)	0.0762 (8)
H4A	1.1522	0.5425	0.9994	0.091*
H4B	1.1292	0.4120	1.0188	0.091*
C19	0.9537 (7)	0.6046 (3)	0.92925 (10)	0.0777 (9)
H19A	0.8547	0.6671	0.9195	0.093*
H19B	1.0469	0.5728	0.9100	0.093*
H19C	1.0453	0.6413	0.9480	0.093*
C17	0.5719 (6)	0.2431 (3)	0.80934 (10)	0.0740 (8)
C2	0.7169 (6)	0.6152 (3)	1.00543 (10)	0.0786 (9)
H2A	0.8062	0.6876	0.9988	0.094*
H2B	0.5917	0.6439	1.0200	0.094*
C1	0.6311 (5)	0.5509 (3)	0.97080 (10)	0.0755 (9)
H1A	0.5450	0.6111	0.9568	0.091*
H1B	0.5309	0.4837	0.9779	0.091*
C15	0.8706 (7)	0.1510 (3)	0.84543 (9)	0.0798 (10)
H15A	1.0158	0.1789	0.8369	0.096*
H15B	0.8886	0.0753	0.8598	0.096*
C20	0.4635 (7)	0.2792 (3)	0.77402 (10)	0.0848 (10)
C18	0.8219 (6)	0.4222 (3)	0.81887 (10)	0.0796 (9)
H18A	0.9000	0.4702	0.8370	0.096*
H18B	0.7488	0.4778	0.8021	0.096*
H18C	0.9261	0.3705	0.8058	0.096*
C23	−0.0205 (12)	0.2941 (6)	0.68619 (14)	0.142 (2)
H23A	−0.1238	0.2336	0.6766	0.171*
H23B	0.0894	0.3134	0.6679	0.171*
H23C	−0.0996	0.3691	0.6928	0.171*
O22	−0.0069 (8)	0.2147 (5)	0.74594 (11)	0.1425 (14)
C16	0.7113 (7)	0.1306 (3)	0.81373 (10)	0.0819 (10)
H16	0.7616	0.0844	0.7920	0.098*
C21	0.4150 (9)	0.1765 (4)	0.74712 (13)	0.1083 (14)
H21A	0.5538	0.1363	0.7401	0.130*
H21B	0.3209	0.1139	0.7587	0.130*
C22	0.0903 (10)	0.2425 (5)	0.71867 (14)	0.1054 (14)
C24	0.8493 (9)	0.5949 (3)	1.09015 (11)	0.0930 (12)
O24	0.6494 (7)	0.5685 (3)	1.09205 (10)	0.1281 (13)
C25	0.9875 (10)	0.6452 (4)	1.12011 (10)	0.1065 (14)
H25A	0.9502	0.7317	1.1242	0.128*
H25B	1.1424	0.6386	1.1136	0.128*
H25C	0.9600	0.5982	1.1421	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0862 (15)	0.0846 (13)	0.0788 (13)	−0.0157 (14)	0.0198 (13)	−0.0133 (12)
C9	0.0486 (14)	0.0559 (13)	0.0834 (18)	0.0075 (12)	0.0085 (14)	−0.0042 (14)
C14	0.0648 (16)	0.0565 (14)	0.0736 (16)	0.0055 (14)	0.0137 (16)	0.0034 (13)
O16	0.0983 (19)	0.0707 (14)	0.1068 (17)	−0.0202 (14)	0.0060 (16)	−0.0021 (13)
C13	0.0587 (16)	0.0573 (14)	0.089 (2)	0.0009 (14)	−0.0026 (16)	0.0002 (14)
C10	0.0474 (13)	0.0527 (13)	0.0850 (18)	0.0077 (13)	0.0089 (14)	0.0003 (13)
C8	0.0594 (15)	0.0550 (13)	0.0707 (16)	0.0108 (13)	0.0116 (15)	0.0065 (12)
C12	0.0582 (18)	0.086 (2)	0.114 (3)	0.0172 (18)	−0.010 (2)	−0.014 (2)
C11	0.0630 (17)	0.0772 (19)	0.115 (3)	0.0256 (17)	−0.014 (2)	−0.0208 (19)
C5	0.0580 (16)	0.0648 (14)	0.0713 (17)	0.0114 (14)	0.0114 (15)	0.0043 (14)
O21	0.100 (2)	0.117 (2)	0.0982 (19)	−0.0125 (19)	−0.0039 (18)	−0.0165 (17)
C7	0.098 (2)	0.0642 (16)	0.0744 (18)	0.0277 (18)	0.009 (2)	0.0059 (14)
C6	0.095 (2)	0.0708 (17)	0.0686 (17)	0.0286 (18)	0.0036 (19)	0.0059 (15)
C3	0.077 (2)	0.0630 (15)	0.086 (2)	−0.0069 (16)	0.0202 (19)	−0.0088 (15)
O20	0.146 (3)	0.0746 (15)	0.137 (2)	−0.0039 (18)	−0.064 (2)	0.0021 (15)
C4	0.0705 (19)	0.0780 (18)	0.0802 (19)	0.0161 (17)	0.0085 (18)	−0.0025 (17)
C19	0.0730 (19)	0.0662 (16)	0.094 (2)	−0.0083 (17)	−0.0039 (19)	0.0078 (16)
C17	0.0718 (18)	0.0638 (16)	0.086 (2)	−0.0048 (16)	0.0022 (18)	−0.0007 (16)
C2	0.0646 (17)	0.0673 (16)	0.104 (2)	0.0054 (15)	0.0140 (19)	−0.0211 (17)
C1	0.0510 (15)	0.0697 (17)	0.106 (2)	0.0090 (14)	0.0083 (17)	−0.0179 (17)
C15	0.098 (3)	0.0655 (16)	0.0763 (19)	0.0229 (19)	0.004 (2)	0.0009 (15)
C20	0.080 (2)	0.076 (2)	0.099 (2)	−0.0055 (19)	−0.015 (2)	−0.0029 (19)
C18	0.076 (2)	0.0717 (17)	0.091 (2)	−0.0076 (17)	−0.0117 (19)	0.0156 (17)
C23	0.148 (5)	0.160 (5)	0.119 (3)	−0.014 (4)	−0.049 (4)	0.021 (4)
O22	0.121 (3)	0.196 (4)	0.111 (2)	−0.021 (3)	0.004 (2)	0.009 (3)
C16	0.100 (3)	0.0639 (17)	0.082 (2)	0.0103 (18)	0.005 (2)	0.0014 (16)
C21	0.115 (3)	0.098 (3)	0.111 (3)	0.008 (3)	−0.035 (3)	−0.022 (2)
C22	0.111 (4)	0.114 (3)	0.092 (3)	−0.012 (3)	−0.009 (3)	−0.010 (3)
C24	0.124 (4)	0.0646 (17)	0.090 (2)	−0.021 (2)	0.028 (3)	0.0041 (17)
O24	0.130 (3)	0.126 (2)	0.129 (2)	−0.044 (2)	0.056 (2)	−0.025 (2)
C25	0.152 (4)	0.092 (2)	0.076 (2)	−0.018 (3)	0.005 (3)	−0.005 (2)

Geometric parameters (Å, º)

O3—C24	1.321 (5)	C3—H3	0.9800
O3—C3	1.461 (4)	O20—C20	1.206 (4)
C9—C8	1.543 (4)	C4—H4A	0.9700
C9—C11	1.543 (4)	C4—H4B	0.9700
C9—C10	1.551 (4)	C19—H19A	0.9600
C9—H9	0.9800	C19—H19B	0.9600
C14—C8	1.518 (4)	C19—H19C	0.9600
C14—C15	1.528 (4)	C17—C16	1.471 (5)
C14—C13	1.546 (4)	C17—C20	1.494 (5)
C14—H14	0.9800	C2—C1	1.527 (5)
O16—C16	1.425 (5)	C2—H2A	0.9700
O16—C17	1.456 (4)	C2—H2B	0.9700
C13—C12	1.518 (5)	C1—H1A	0.9700
C13—C17	1.520 (5)	C1—H1B	0.9700
C13—C18	1.539 (5)	C15—C16	1.515 (5)
C10—C5	1.519 (4)	C15—H15A	0.9700
C10—C1	1.546 (4)	C15—H15B	0.9700
C10—C19	1.549 (4)	C20—C21	1.499 (6)
C8—C7	1.519 (4)	C18—H18A	0.9600
C8—H8	0.9800	C18—H18B	0.9600
C12—C11	1.539 (5)	C18—H18C	0.9600
C12—H12A	0.9700	C23—C22	1.466 (7)
C12—H12B	0.9700	C23—H23A	0.9600
C11—H11A	0.9700	C23—H23B	0.9600
C11—H11B	0.9700	C23—H23C	0.9600
C5—C6	1.332 (4)	O22—C22	1.191 (6)
C5—C4	1.499 (4)	C16—H16	0.9800
O21—C22	1.300 (7)	C21—H21A	0.9700
O21—C21	1.457 (5)	C21—H21B	0.9700
C7—C6	1.476 (5)	C24—O24	1.232 (6)
C7—H7A	0.9700	C24—C25	1.473 (6)
C7—H7B	0.9700	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C3—C2	1.505 (5)	C25—H25C	0.9600
C3—C4	1.521 (5)
C24—O3—C3	119.7 (3)	C10—C19—H19A	109.5
C8—C9—C11	112.6 (2)	C10—C19—H19B	109.5
C8—C9—C10	112.0 (2)	H19A—C19—H19B	109.5
C11—C9—C10	112.9 (2)	C10—C19—H19C	109.5
C8—C9—H9	106.3	H19A—C19—H19C	109.5
C11—C9—H9	106.3	H19B—C19—H19C	109.5
C10—C9—H9	106.3	O16—C17—C16	58.3 (2)
C8—C14—C15	121.1 (3)	O16—C17—C20	112.3 (3)
C8—C14—C13	113.5 (2)	C16—C17—C20	123.4 (3)
C15—C14—C13	104.2 (2)	O16—C17—C13	115.3 (3)
C8—C14—H14	105.6	C16—C17—C13	107.8 (3)
C15—C14—H14	105.6	C20—C17—C13	122.9 (3)
C13—C14—H14	105.6	C3—C2—C1	110.0 (3)
C16—O16—C17	61.4 (2)	C3—C2—H2A	109.7
C12—C13—C17	117.3 (3)	C1—C2—H2A	109.7
C12—C13—C18	111.8 (3)	C3—C2—H2B	109.7
C17—C13—C18	106.6 (3)	C1—C2—H2B	109.7
C12—C13—C14	107.2 (3)	H2A—C2—H2B	108.2
C17—C13—C14	101.7 (2)	C2—C1—C10	114.8 (3)
C18—C13—C14	112.0 (3)	C2—C1—H1A	108.6
C5—C10—C1	107.9 (3)	C10—C1—H1A	108.6
C5—C10—C19	107.9 (3)	C2—C1—H1B	108.6
C1—C10—C19	109.2 (2)	C10—C1—H1B	108.6
C5—C10—C9	110.8 (2)	H1A—C1—H1B	107.6
C1—C10—C9	108.8 (2)	C16—C15—C14	102.1 (3)
C19—C10—C9	112.2 (3)	C16—C15—H15A	111.4
C14—C8—C7	112.0 (2)	C14—C15—H15A	111.4
C14—C8—C9	108.5 (2)	C16—C15—H15B	111.4
C7—C8—C9	110.4 (2)	C14—C15—H15B	111.4
C14—C8—H8	108.7	H15A—C15—H15B	109.2
C7—C8—H8	108.7	O20—C20—C17	121.7 (3)
C9—C8—H8	108.7	O20—C20—C21	120.8 (4)
C13—C12—C11	110.2 (3)	C17—C20—C21	117.5 (3)
C13—C12—H12A	109.6	C13—C18—H18A	109.5
C11—C12—H12A	109.6	C13—C18—H18B	109.5
C13—C12—H12B	109.6	H18A—C18—H18B	109.5
C11—C12—H12B	109.6	C13—C18—H18C	109.5
H12A—C12—H12B	108.1	H18A—C18—H18C	109.5
C12—C11—C9	114.8 (3)	H18B—C18—H18C	109.5
C12—C11—H11A	108.6	C22—C23—H23A	109.5
C9—C11—H11A	108.6	C22—C23—H23B	109.5
C12—C11—H11B	108.6	H23A—C23—H23B	109.5
C9—C11—H11B	108.6	C22—C23—H23C	109.5
H11A—C11—H11B	107.5	H23A—C23—H23C	109.5
C6—C5—C4	120.6 (3)	H23B—C23—H23C	109.5
C6—C5—C10	122.0 (3)	O16—C16—C17	60.4 (2)
C4—C5—C10	117.3 (3)	O16—C16—C15	114.0 (3)
C22—O21—C21	114.0 (4)	C17—C16—C15	108.9 (3)
C6—C7—C8	113.0 (2)	O16—C16—H16	119.8
C6—C7—H7A	109.0	C17—C16—H16	119.8
C8—C7—H7A	109.0	C15—C16—H16	119.8
C6—C7—H7B	109.0	O21—C21—C20	111.6 (4)
C8—C7—H7B	109.0	O21—C21—H21A	109.3
H7A—C7—H7B	107.8	C20—C21—H21A	109.3
C5—C6—C7	126.0 (3)	O21—C21—H21B	109.3
C5—C6—H6	117.0	C20—C21—H21B	109.3
C7—C6—H6	117.0	H21A—C21—H21B	108.0
O3—C3—C2	111.8 (3)	O22—C22—O21	122.7 (5)
O3—C3—C4	105.3 (3)	O22—C22—C23	123.3 (6)
C2—C3—C4	110.8 (3)	O21—C22—C23	114.0 (5)
O3—C3—H3	109.6	O24—C24—O3	121.4 (4)
C2—C3—H3	109.6	O24—C24—C25	126.0 (4)
C4—C3—H3	109.6	O3—C24—C25	112.5 (4)
C5—C4—C3	111.8 (3)	C24—C25—H25A	109.5
C5—C4—H4A	109.3	C24—C25—H25B	109.5
C3—C4—H4A	109.3	H25A—C25—H25B	109.5
C5—C4—H4B	109.3	C24—C25—H25C	109.5
C3—C4—H4B	109.3	H25A—C25—H25C	109.5
H4A—C4—H4B	107.9	H25B—C25—H25C	109.5
C8—C14—C13—C12	−64.5 (3)	C16—O16—C17—C13	−96.0 (3)
C15—C14—C13—C12	161.7 (3)	C12—C13—C17—O16	−78.2 (4)
C8—C14—C13—C17	171.8 (3)	C18—C13—C17—O16	155.6 (3)
C15—C14—C13—C17	38.1 (3)	C14—C13—C17—O16	38.2 (4)
C8—C14—C13—C18	58.4 (3)	C12—C13—C17—C16	−140.9 (3)
C15—C14—C13—C18	−75.3 (3)	C18—C13—C17—C16	93.0 (3)
C8—C9—C10—C5	−44.5 (3)	C14—C13—C17—C16	−24.4 (4)
C11—C9—C10—C5	−172.9 (3)	C12—C13—C17—C20	65.4 (5)
C8—C9—C10—C1	−163.0 (2)	C18—C13—C17—C20	−60.7 (4)
C11—C9—C10—C1	68.6 (3)	C14—C13—C17—C20	−178.1 (3)
C8—C9—C10—C19	76.1 (3)	O3—C3—C2—C1	174.3 (3)
C11—C9—C10—C19	−52.3 (3)	C4—C3—C2—C1	57.2 (4)
C15—C14—C8—C7	−53.6 (4)	C3—C2—C1—C10	−57.0 (4)
C13—C14—C8—C7	−178.8 (3)	C5—C10—C1—C2	49.6 (3)
C15—C14—C8—C9	−175.6 (3)	C19—C10—C1—C2	−67.3 (4)
C13—C14—C8—C9	59.2 (3)	C9—C10—C1—C2	170.0 (3)
C11—C9—C8—C14	−49.0 (3)	C8—C14—C15—C16	−166.3 (3)
C10—C9—C8—C14	−177.5 (2)	C13—C14—C15—C16	−37.0 (3)
C11—C9—C8—C7	−172.0 (3)	O16—C17—C20—O20	138.8 (4)
C10—C9—C8—C7	59.5 (3)	C16—C17—C20—O20	−155.4 (5)
C17—C13—C12—C11	171.2 (3)	C13—C17—C20—O20	−5.8 (6)
C18—C13—C12—C11	−65.3 (4)	O16—C17—C20—C21	−40.3 (5)
C14—C13—C12—C11	57.8 (4)	C16—C17—C20—C21	25.4 (6)
C13—C12—C11—C9	−52.7 (4)	C13—C17—C20—C21	175.1 (4)
C8—C9—C11—C12	48.0 (4)	C17—O16—C16—C15	98.8 (3)
C10—C9—C11—C12	176.0 (3)	C20—C17—C16—O16	−97.2 (4)
C1—C10—C5—C6	132.6 (3)	C13—C17—C16—O16	109.2 (3)
C19—C10—C5—C6	−109.6 (4)	O16—C17—C16—C15	−107.5 (3)
C9—C10—C5—C6	13.5 (4)	C20—C17—C16—C15	155.3 (3)
C1—C10—C5—C4	−47.1 (3)	C13—C17—C16—C15	1.7 (4)
C19—C10—C5—C4	70.7 (3)	C14—C15—C16—O16	−43.2 (4)
C9—C10—C5—C4	−166.1 (3)	C14—C15—C16—C17	22.0 (4)
C14—C8—C7—C6	−162.2 (3)	C22—O21—C21—C20	−80.3 (6)
C9—C8—C7—C6	−41.2 (4)	O20—C20—C21—O21	−0.9 (7)
C4—C5—C6—C7	−176.5 (4)	C17—C20—C21—O21	178.3 (4)
C10—C5—C6—C7	3.8 (6)	C21—O21—C22—O22	−4.5 (7)
C8—C7—C6—C5	10.8 (6)	C21—O21—C22—C23	178.3 (4)
C24—O3—C3—C2	86.6 (4)	C3—O3—C24—O24	−10.1 (6)
C24—O3—C3—C4	−153.0 (3)	C3—O3—C24—C25	173.2 (3)
C6—C5—C4—C3	−128.5 (3)	C18—C13—C10—C19	12.4 (2)
C10—C5—C4—C3	51.1 (4)	C13—C17—C20—O20	−5.8 (6)
O3—C3—C4—C5	−175.4 (3)	C21—O21—C22—O22	−4.5 (7)
C2—C3—C4—C5	−54.3 (4)	O20—C20—C21—O21	−0.9 (7)
C16—O16—C17—C20	116.5 (4)