5α,6α-Ep-oxy-7-norcholestan-3β-yl acetate.

The title cholestan, C(28)H(46)O(3), was prepared by epoxidation of 7-norcholest-5-en-3β-yl acetate and crystallized by slow evaporation from an ethano-lic solution. All rings are trans fused. The 3β-acetate and the 17β-cholestane side chain are in equatorial positions. The mol-ecule is highly twisted due to its B-nor characteristic. A quantum chemical ab-initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond lengths and valency angles in close agreement with the experimental ones.

Related literature

For the chemistry of the title compound, see: Carvalho et al. (2009a ▶, 2010a ▶). For studies of biological activity of steroids, see: Carvalho et al. (2009b ▶, 2010b ▶). For the influence of structural characteristics of B-nor steroids on the outcome of many reactions, see: Uyanik & Hanson (2009) ▶. For asymmetry parameters, see: Duax & Norton (1975 ▶); Altona et al. (1968 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For the melting point of the title compound, see: Joska et al. (1963 ▶). For the software used in ab-initio calculations, see Schmidt et al. (1993 ▶).

Experimental

Crystal data

C28H46O3

M = 430.65

Monoclinic,

a = 7.5820 (1) Å

b = 9.7487 (1) Å

c = 17.8588 (2) Å

β = 93.1792 (18)°

V = 1318.00 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.44 × 0.24 × 0.16 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.981, T max = 0.989

35109 measured reflections

6194 independent reflections

3551 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 0.96

6194 reflections

286 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 2846 Friedel pairs

Flack parameter: −0.5 (15)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811054249/im2347sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054249/im2347Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H46O3	Dx = 1.075 Mg m−3
Mr = 430.65	Melting point: 386 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.5820 (1) Å	Cell parameters from 9561 reflections
b = 9.7487 (1) Å	θ = 2.4–21.0°
c = 17.8588 (2) Å	µ = 0.07 mm−1
β = 93.1792 (18)°	T = 293 K
V = 1318.00 (3) Å3	Prism, colourless
Z = 2	0.44 × 0.24 × 0.16 mm
F(000) = 476

Bruker APEX CCD area-detector diffractometer	6194 independent reflections
Radiation source: fine-focus sealed tube	3551 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
Tmin = 0.981, Tmax = 0.989	k = −12→12
35109 measured reflections	l = −22→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.1597P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
6194 reflections	Δρmax = 0.23 e Å−3
286 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 2846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.5 (15)

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.

	x	y	z	Uiso*/Ueq
C9	0.9354 (3)	0.4824 (2)	0.25045 (11)	0.0496 (5)
H9	0.8803	0.4012	0.2715	0.060*
O56	0.59348 (19)	0.50504 (19)	0.26154 (8)	0.0663 (4)
C10	0.8357 (3)	0.5092 (2)	0.17350 (11)	0.0537 (5)
O3	0.3659 (2)	0.5251 (2)	0.03122 (9)	0.0795 (5)
C12	1.1969 (3)	0.4357 (2)	0.33813 (13)	0.0561 (5)
H12A	1.1475	0.3512	0.3566	0.067*
H12B	1.3244	0.4265	0.3409	0.067*
C13	1.1450 (3)	0.5549 (2)	0.38854 (11)	0.0492 (5)
C7	0.8837 (3)	0.6045 (2)	0.29938 (12)	0.0517 (5)
H7	0.9516	0.6841	0.2838	0.062*
C14	0.9426 (3)	0.5733 (2)	0.37979 (11)	0.0521 (5)
H14	0.8894	0.4854	0.3926	0.062*
C20	1.3527 (3)	0.5455 (3)	0.51411 (12)	0.0631 (6)
H20	1.3928	0.6398	0.5068	0.076*
C17	1.1673 (3)	0.5317 (2)	0.47510 (11)	0.0563 (5)
H17	1.1257	0.4386	0.4850	0.068*
C11	1.1318 (3)	0.4564 (3)	0.25588 (12)	0.0597 (6)
H11A	1.1929	0.5337	0.2350	0.072*
H11B	1.1583	0.3754	0.2271	0.072*
C6	0.6944 (3)	0.6292 (3)	0.27422 (13)	0.0621 (6)
H6	0.6353	0.7138	0.2886	0.075*
C5	0.6662 (3)	0.5752 (2)	0.19835 (13)	0.0573 (6)
C3	0.4844 (3)	0.4820 (3)	0.09382 (13)	0.0672 (7)
H3	0.4229	0.4183	0.1259	0.081*
C1	0.7853 (3)	0.3819 (3)	0.12798 (13)	0.0670 (6)
H1A	0.7392	0.3131	0.1610	0.080*
H1B	0.8901	0.3444	0.1068	0.080*
C18	1.2455 (3)	0.6852 (3)	0.36837 (14)	0.0664 (6)
H18A	1.3703	0.6693	0.3755	0.100*
H18B	1.2122	0.7592	0.4001	0.100*
H18C	1.2169	0.7087	0.3169	0.100*
C19	0.9377 (3)	0.6129 (3)	0.12773 (14)	0.0754 (7)
H19A	0.8680	0.6373	0.0832	0.113*
H19B	1.0469	0.5727	0.1141	0.113*
H19C	0.9620	0.6936	0.1573	0.113*
C21	1.4874 (4)	0.4498 (3)	0.48156 (17)	0.0861 (8)
H21A	1.5950	0.4520	0.5125	0.129*
H21B	1.5106	0.4791	0.4317	0.129*
H21C	1.4416	0.3580	0.4799	0.129*
C22	1.3466 (4)	0.5206 (3)	0.59896 (13)	0.0799 (8)
H22A	1.2417	0.5644	0.6165	0.096*
H22B	1.3356	0.4229	0.6076	0.096*
C16	1.0325 (4)	0.6318 (3)	0.50653 (15)	0.0787 (8)
H16A	1.0926	0.7120	0.5276	0.094*
H16B	0.9696	0.5877	0.5458	0.094*
C4	0.5304 (3)	0.6124 (3)	0.13705 (14)	0.0668 (7)
H4A	0.5776	0.6805	0.1040	0.080*
H4B	0.4258	0.6500	0.1584	0.080*
O28	0.2305 (3)	0.3225 (3)	0.02880 (15)	0.1146 (8)
C28	0.2462 (4)	0.4337 (4)	0.00463 (16)	0.0817 (8)
C2	0.6466 (4)	0.4123 (3)	0.06445 (14)	0.0770 (8)
H2A	0.6979	0.4712	0.0277	0.092*
H2B	0.6114	0.3272	0.0397	0.092*
C15	0.9018 (3)	0.6743 (3)	0.44114 (13)	0.0730 (7)
H15A	0.7804	0.6656	0.4550	0.088*
H15B	0.9225	0.7680	0.4256	0.088*
C24	1.5074 (5)	0.5303 (4)	0.72649 (15)	0.1002 (10)
H24A	1.3964	0.5577	0.7465	0.120*
H24B	1.5132	0.4309	0.7288	0.120*
C23	1.5041 (4)	0.5726 (4)	0.64467 (15)	0.0975 (10)
H23A	1.5058	0.6720	0.6418	0.117*
H23B	1.6103	0.5389	0.6230	0.117*
C29	0.1328 (4)	0.4931 (4)	−0.05840 (16)	0.1031 (11)
H29A	0.2018	0.5049	−0.1014	0.155*
H29B	0.0879	0.5804	−0.0435	0.155*
H29C	0.0361	0.4322	−0.0708	0.155*
C25	1.6529 (5)	0.5861 (4)	0.77614 (16)	0.0989 (10)
H25	1.6427	0.6863	0.7743	0.119*
C26	1.8343 (5)	0.5507 (5)	0.7531 (2)	0.1229 (13)
H26A	1.8534	0.4539	0.7588	0.184*
H26B	1.9204	0.5996	0.7842	0.184*
H26C	1.8452	0.5761	0.7016	0.184*
C27	1.6293 (6)	0.5434 (6)	0.85708 (18)	0.1511 (18)
H27A	1.5149	0.5719	0.8717	0.227*
H27B	1.7190	0.5859	0.8893	0.227*
H27C	1.6391	0.4455	0.8613	0.227*

	U11	U22	U33	U12	U13	U23
C9	0.0499 (11)	0.0536 (12)	0.0447 (11)	0.0052 (9)	−0.0024 (9)	−0.0030 (9)
O56	0.0528 (9)	0.0922 (12)	0.0533 (9)	−0.0007 (9)	−0.0012 (7)	−0.0018 (9)
C10	0.0518 (12)	0.0643 (14)	0.0442 (11)	0.0041 (11)	−0.0034 (9)	0.0013 (10)
O3	0.0679 (10)	0.1045 (14)	0.0629 (10)	−0.0054 (11)	−0.0248 (8)	0.0075 (11)
C12	0.0522 (12)	0.0576 (13)	0.0574 (13)	0.0101 (10)	−0.0069 (10)	0.0014 (11)
C13	0.0520 (12)	0.0456 (11)	0.0492 (11)	0.0046 (9)	−0.0056 (9)	0.0013 (9)
C7	0.0507 (12)	0.0520 (12)	0.0515 (12)	0.0073 (10)	−0.0058 (10)	−0.0058 (10)
C14	0.0537 (12)	0.0537 (12)	0.0480 (11)	0.0056 (10)	−0.0037 (9)	−0.0049 (10)
C20	0.0712 (15)	0.0587 (14)	0.0569 (13)	−0.0026 (12)	−0.0204 (11)	0.0066 (11)
C17	0.0622 (13)	0.0559 (13)	0.0495 (12)	−0.0048 (11)	−0.0094 (10)	0.0047 (11)
C11	0.0570 (13)	0.0693 (15)	0.0520 (12)	0.0161 (11)	−0.0043 (10)	−0.0080 (11)
C6	0.0560 (14)	0.0711 (15)	0.0580 (14)	0.0173 (12)	−0.0088 (11)	−0.0121 (12)
C5	0.0512 (12)	0.0651 (14)	0.0545 (13)	0.0078 (10)	−0.0074 (10)	0.0004 (11)
C3	0.0590 (14)	0.0877 (17)	0.0529 (13)	0.0013 (13)	−0.0150 (11)	0.0025 (13)
C1	0.0660 (15)	0.0805 (16)	0.0531 (14)	0.0097 (13)	−0.0100 (11)	−0.0131 (12)
C18	0.0660 (15)	0.0608 (14)	0.0704 (16)	−0.0063 (12)	−0.0149 (12)	0.0130 (12)
C19	0.0682 (16)	0.103 (2)	0.0546 (14)	−0.0009 (14)	−0.0025 (12)	0.0167 (14)
C21	0.0722 (17)	0.099 (2)	0.0840 (19)	0.0175 (15)	−0.0279 (14)	0.0004 (16)
C22	0.0922 (18)	0.0841 (19)	0.0598 (14)	−0.0182 (16)	−0.0270 (13)	0.0073 (14)
C16	0.0785 (18)	0.098 (2)	0.0579 (15)	0.0101 (15)	−0.0103 (13)	−0.0162 (14)
C4	0.0556 (14)	0.0803 (17)	0.0626 (14)	0.0086 (12)	−0.0129 (11)	0.0033 (13)
O28	0.127 (2)	0.0950 (16)	0.1150 (19)	−0.0149 (15)	−0.0555 (15)	−0.0021 (14)
C28	0.0705 (17)	0.107 (2)	0.0651 (17)	0.0073 (17)	−0.0157 (14)	−0.0145 (17)
C2	0.0760 (17)	0.096 (2)	0.0565 (15)	0.0054 (14)	−0.0159 (13)	−0.0154 (14)
C15	0.0675 (15)	0.0909 (18)	0.0591 (15)	0.0183 (14)	−0.0095 (12)	−0.0236 (14)
C24	0.121 (2)	0.113 (2)	0.0625 (16)	−0.030 (2)	−0.0267 (16)	0.0080 (18)
C23	0.108 (2)	0.112 (2)	0.0685 (17)	−0.0300 (19)	−0.0324 (15)	0.0102 (17)
C29	0.094 (2)	0.128 (3)	0.083 (2)	0.008 (2)	−0.0386 (16)	−0.007 (2)
C25	0.115 (3)	0.106 (2)	0.0716 (19)	−0.010 (2)	−0.0314 (18)	0.0022 (17)
C26	0.103 (3)	0.152 (3)	0.110 (3)	0.003 (3)	−0.026 (2)	−0.006 (3)
C27	0.167 (4)	0.214 (5)	0.068 (2)	−0.035 (4)	−0.033 (2)	0.011 (3)

C9—C11	1.509 (3)	C18—H18B	0.9600
C9—C7	1.540 (3)	C18—H18C	0.9600
C9—C10	1.553 (3)	C19—H19A	0.9600
C9—H9	0.9800	C19—H19B	0.9600
O56—C6	1.443 (3)	C19—H19C	0.9600
O56—C5	1.454 (3)	C21—H21A	0.9600
C10—C1	1.521 (3)	C21—H21B	0.9600
C10—C5	1.525 (3)	C21—H21C	0.9600
C10—C19	1.535 (3)	C22—C23	1.497 (4)
O3—C28	1.340 (4)	C22—H22A	0.9700
O3—C3	1.457 (3)	C22—H22B	0.9700
C12—C13	1.534 (3)	C16—C15	1.546 (4)
C12—C11	1.537 (3)	C16—H16A	0.9700
C12—H12A	0.9700	C16—H16B	0.9700
C12—H12B	0.9700	C4—H4A	0.9700
C13—C18	1.535 (3)	C4—H4B	0.9700
C13—C14	1.544 (3)	O28—C28	1.175 (4)
C13—C17	1.562 (3)	C28—C29	1.495 (4)
C7—C6	1.500 (3)	C2—H2A	0.9700
C7—C14	1.511 (3)	C2—H2B	0.9700
C7—H7	0.9800	C15—H15A	0.9700
C14—C15	1.518 (3)	C15—H15B	0.9700
C14—H14	0.9800	C24—C25	1.480 (4)
C20—C21	1.522 (4)	C24—C23	1.517 (4)
C20—C22	1.538 (3)	C24—H24A	0.9700
C20—C17	1.540 (3)	C24—H24B	0.9700
C20—H20	0.9800	C23—H23A	0.9700
C17—C16	1.542 (4)	C23—H23B	0.9700
C17—H17	0.9800	C29—H29A	0.9600
C11—H11A	0.9700	C29—H29B	0.9600
C11—H11B	0.9700	C29—H29C	0.9600
C6—C5	1.458 (3)	C25—C26	1.497 (5)
C6—H6	0.9800	C25—C27	1.524 (4)
C5—C4	1.505 (3)	C25—H25	0.9800
C3—C4	1.517 (4)	C26—H26A	0.9600
C3—C2	1.524 (4)	C26—H26B	0.9600
C3—H3	0.9800	C26—H26C	0.9600
C1—C2	1.533 (3)	C27—H27A	0.9600
C1—H1A	0.9700	C27—H27B	0.9600
C1—H1B	0.9700	C27—H27C	0.9600
C18—H18A	0.9600
C11—C9—C7	112.00 (17)	H18A—C18—H18C	109.5
C11—C9—C10	121.01 (17)	H18B—C18—H18C	109.5
C7—C9—C10	104.22 (16)	C10—C19—H19A	109.5
C11—C9—H9	106.2	C10—C19—H19B	109.5
C7—C9—H9	106.2	H19A—C19—H19B	109.5
C10—C9—H9	106.2	C10—C19—H19C	109.5
C6—O56—C5	60.45 (15)	H19A—C19—H19C	109.5
C1—C10—C5	107.96 (18)	H19B—C19—H19C	109.5
C1—C10—C19	111.84 (19)	C20—C21—H21A	109.5
C5—C10—C19	109.6 (2)	C20—C21—H21B	109.5
C1—C10—C9	115.54 (19)	H21A—C21—H21B	109.5
C5—C10—C9	100.95 (16)	C20—C21—H21C	109.5
C19—C10—C9	110.31 (18)	H21A—C21—H21C	109.5
C28—O3—C3	117.2 (2)	H21B—C21—H21C	109.5
C13—C12—C11	112.47 (17)	C23—C22—C20	114.7 (2)
C13—C12—H12A	109.1	C23—C22—H22A	108.6
C11—C12—H12A	109.1	C20—C22—H22A	108.6
C13—C12—H12B	109.1	C23—C22—H22B	108.6
C11—C12—H12B	109.1	C20—C22—H22B	108.6
H12A—C12—H12B	107.8	H22A—C22—H22B	107.6
C12—C13—C18	110.04 (18)	C17—C16—C15	107.76 (19)
C12—C13—C14	108.29 (17)	C17—C16—H16A	110.2
C18—C13—C14	112.56 (17)	C15—C16—H16A	110.2
C12—C13—C17	116.99 (17)	C17—C16—H16B	110.2
C18—C13—C17	108.93 (18)	C15—C16—H16B	110.2
C14—C13—C17	99.73 (15)	H16A—C16—H16B	108.5
C6—C7—C14	123.00 (19)	C5—C4—C3	107.3 (2)
C6—C7—C9	102.89 (17)	C5—C4—H4A	110.3
C14—C7—C9	108.20 (16)	C3—C4—H4A	110.3
C6—C7—H7	107.3	C5—C4—H4B	110.3
C14—C7—H7	107.3	C3—C4—H4B	110.3
C9—C7—H7	107.3	H4A—C4—H4B	108.5
C7—C14—C15	119.57 (18)	O28—C28—O3	124.3 (3)
C7—C14—C13	111.05 (16)	O28—C28—C29	124.7 (3)
C15—C14—C13	104.11 (17)	O3—C28—C29	111.0 (3)
C7—C14—H14	107.2	C3—C2—C1	111.4 (2)
C15—C14—H14	107.2	C3—C2—H2A	109.3
C13—C14—H14	107.2	C1—C2—H2A	109.3
C21—C20—C22	109.7 (2)	C3—C2—H2B	109.3
C21—C20—C17	112.9 (2)	C1—C2—H2B	109.3
C22—C20—C17	110.8 (2)	H2A—C2—H2B	108.0
C21—C20—H20	107.7	C14—C15—C16	102.9 (2)
C22—C20—H20	107.7	C14—C15—H15A	111.2
C17—C20—H20	107.7	C16—C15—H15A	111.2
C20—C17—C16	112.78 (19)	C14—C15—H15B	111.2
C20—C17—C13	118.75 (18)	C16—C15—H15B	111.2
C16—C17—C13	103.37 (17)	H15A—C15—H15B	109.1
C20—C17—H17	107.1	C25—C24—C23	116.7 (3)
C16—C17—H17	107.1	C25—C24—H24A	108.1
C13—C17—H17	107.1	C23—C24—H24A	108.1
C9—C11—C12	110.30 (18)	C25—C24—H24B	108.1
C9—C11—H11A	109.6	C23—C24—H24B	108.1
C12—C11—H11A	109.6	H24A—C24—H24B	107.3
C9—C11—H11B	109.6	C22—C23—C24	113.8 (3)
C12—C11—H11B	109.6	C22—C23—H23A	108.8
H11A—C11—H11B	108.1	C24—C23—H23A	108.8
O56—C6—C5	60.15 (14)	C22—C23—H23B	108.8
O56—C6—C7	113.77 (18)	C24—C23—H23B	108.8
C5—C6—C7	108.02 (18)	H23A—C23—H23B	107.7
O56—C6—H6	120.1	C28—C29—H29A	109.5
C5—C6—H6	120.1	C28—C29—H29B	109.5
C7—C6—H6	120.1	H29A—C29—H29B	109.5
O56—C5—C6	59.41 (15)	C28—C29—H29C	109.5
O56—C5—C4	113.85 (19)	H29A—C29—H29C	109.5
C6—C5—C4	130.4 (2)	H29B—C29—H29C	109.5
O56—C5—C10	112.92 (18)	C24—C25—C26	114.6 (3)
C6—C5—C10	109.87 (17)	C24—C25—C27	110.2 (3)
C4—C5—C10	116.33 (19)	C26—C25—C27	110.8 (3)
O3—C3—C4	105.3 (2)	C24—C25—H25	106.9
O3—C3—C2	109.85 (19)	C26—C25—H25	106.9
C4—C3—C2	112.4 (2)	C27—C25—H25	106.9
O3—C3—H3	109.7	C25—C26—H26A	109.5
C4—C3—H3	109.7	C25—C26—H26B	109.5
C2—C3—H3	109.7	H26A—C26—H26B	109.5
C10—C1—C2	112.3 (2)	C25—C26—H26C	109.5
C10—C1—H1A	109.1	H26A—C26—H26C	109.5
C2—C1—H1A	109.1	H26B—C26—H26C	109.5
C10—C1—H1B	109.1	C25—C27—H27A	109.5
C2—C1—H1B	109.1	C25—C27—H27B	109.5
H1A—C1—H1B	107.9	H27A—C27—H27B	109.5
C13—C18—H18A	109.5	C25—C27—H27C	109.5
C13—C18—H18B	109.5	H27A—C27—H27C	109.5
H18A—C18—H18B	109.5	H27B—C27—H27C	109.5
C13—C18—H18C	109.5
C11—C9—C10—C1	82.1 (3)	C6—O56—C5—C10	100.3 (2)
C7—C9—C10—C1	−150.83 (18)	C7—C6—C5—O56	107.6 (2)
C11—C9—C10—C5	−161.8 (2)	O56—C6—C5—C4	96.5 (3)
C7—C9—C10—C5	−34.7 (2)	C7—C6—C5—C4	−155.9 (2)
C11—C9—C10—C19	−46.0 (3)	O56—C6—C5—C10	−105.5 (2)
C7—C9—C10—C19	81.1 (2)	C7—C6—C5—C10	2.1 (3)
C11—C12—C13—C18	−67.9 (2)	C1—C10—C5—O56	77.9 (2)
C11—C12—C13—C14	55.6 (2)	C19—C10—C5—O56	−160.12 (18)
C11—C12—C13—C17	167.16 (19)	C9—C10—C5—O56	−43.8 (2)
C11—C9—C7—C6	169.22 (19)	C1—C10—C5—C6	142.1 (2)
C10—C9—C7—C6	36.7 (2)	C19—C10—C5—C6	−95.9 (2)
C11—C9—C7—C14	−59.2 (2)	C9—C10—C5—C6	20.5 (2)
C10—C9—C7—C14	168.28 (17)	C1—C10—C5—C4	−56.5 (3)
C6—C7—C14—C15	−58.0 (3)	C19—C10—C5—C4	65.5 (3)
C9—C7—C14—C15	−177.5 (2)	C9—C10—C5—C4	−178.1 (2)
C6—C7—C14—C13	−179.2 (2)	C28—O3—C3—C4	−150.8 (2)
C9—C7—C14—C13	61.2 (2)	C28—O3—C3—C2	87.9 (3)
C12—C13—C14—C7	−59.8 (2)	C5—C10—C1—C2	52.3 (3)
C18—C13—C14—C7	62.1 (2)	C19—C10—C1—C2	−68.3 (3)
C17—C13—C14—C7	177.40 (17)	C9—C10—C1—C2	164.4 (2)
C12—C13—C14—C15	170.26 (19)	C21—C20—C22—C23	72.5 (3)
C18—C13—C14—C15	−67.9 (2)	C17—C20—C22—C23	−162.2 (3)
C17—C13—C14—C15	47.5 (2)	C20—C17—C16—C15	146.4 (2)
C21—C20—C17—C16	−178.2 (2)	C13—C17—C16—C15	16.9 (3)
C22—C20—C17—C16	58.2 (3)	O56—C5—C4—C3	−76.4 (3)
C21—C20—C17—C13	−57.1 (3)	C6—C5—C4—C3	−145.6 (3)
C22—C20—C17—C13	179.3 (2)	C10—C5—C4—C3	57.5 (3)
C12—C13—C17—C20	79.4 (3)	O3—C3—C4—C5	−174.84 (19)
C18—C13—C17—C20	−46.1 (2)	C2—C3—C4—C5	−55.2 (3)
C14—C13—C17—C20	−164.20 (19)	C3—O3—C28—O28	0.5 (4)
C12—C13—C17—C16	−154.9 (2)	C3—O3—C28—C29	179.1 (2)
C18—C13—C17—C16	79.6 (2)	O3—C3—C2—C1	172.8 (2)
C14—C13—C17—C16	−38.4 (2)	C4—C3—C2—C1	55.9 (3)
C7—C9—C11—C12	55.5 (2)	C10—C1—C2—C3	−54.3 (3)
C10—C9—C11—C12	179.0 (2)	C7—C14—C15—C16	−161.8 (2)
C13—C12—C11—C9	−54.3 (3)	C13—C14—C15—C16	−37.1 (3)
C5—O56—C6—C7	−97.9 (2)	C17—C16—C15—C14	12.1 (3)
C14—C7—C6—O56	−81.5 (3)	C20—C22—C23—C24	−172.1 (3)
C9—C7—C6—O56	40.5 (2)	C25—C24—C23—C22	−175.9 (3)
C14—C7—C6—C5	−146.1 (2)	C23—C24—C25—C26	−58.7 (5)
C9—C7—C6—C5	−24.1 (2)	C23—C24—C25—C27	175.5 (4)
C6—O56—C5—C4	−124.2 (2)	C19—C10—C13—C18	12.68 (18)