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(5S,9S,17S)-17-Hydroxy-9(10→5)-abeo-estr-4-ene-3,10-dione, C18H26O3, (II), and (5R,9R,17S)-17-hydroxy-9(10→5)-abeo-estr-4-ene-3,10-dione, C18H26O3, (III), are equimolecular products of the FeII-induced transposition of 10β-hydro­peroxy-17β-hydroxyestr-4-en-3-one, (I). With respect to reagent mol­ecules, the configuration at C9 is retained for (II) while it is inverted in (III). The conformations of the five- and six-membered rings are compared.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101001767/na1501sup1.cif
Contains datablocks global, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001767/na1501IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001767/na1501IIIsup3.hkl
Contains datablock III

CCDC references: 163949; 163950

Computing details top

For both compounds, data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS. Program(s) used to solve structure: SIR92 (Altomare et al. 1994) for (II); SIR92 (Altomare et al., 1994) for (III). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARSTCIF (Nardelli, 1991) for (II); SHELXL97 for (III).

(II) (5S,9S,17S)-9(105)-abeo-4,5-dihydroestrene-17-hydroxy-3,10-dione top
Crystal data top
C18H26O3Dx = 1.260 Mg m3
Mr = 290.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 52 reflections
a = 6.5843 (5) Åθ = 5.2–14.8°
b = 10.4040 (7) ŵ = 0.08 mm1
c = 22.3443 (12) ÅT = 293 K
V = 1530.65 (18) Å3Cubic, colourless
Z = 40.32 × 0.30 × 0.30 mm
F(000) = 632
Data collection top
Bruker P4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 1.8°
Graphite monochromatorh = 09
2θ/ω scansk = 014
5088 measured reflectionsl = 031
2577 independent reflections3 standard reflections every 197 reflections
2216 reflections with I > 2σ(I) intensity decay: 0.0%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0474P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max = 0.014
S = 0.98Δρmax = 0.24 e Å3
2577 reflectionsΔρmin = 0.13 e Å3
295 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0151 (19)
Primary atom site location: structure-invariant direct methodsAbsolute structure: based on the reagents configuration
Secondary atom site location: difference Fourier map
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry.

Ring puckering coordinates following Cremer D. & Pople J·A., JACS (1975).97,1354

Ring 1 Atom Internal Cartesian coordinates X Y Z C1 0.0000(0.0000) 1.4755(0.0018) 0.1552(0.0014) C2 1.2456(0.0020) 0.7323(0.0025) -0.3070(0.0013) C3 1.2962(0.0017) -0.7103(0.0023) 0.1144(0.0014) C4 - 0.0176(0.0022) -1.4395(0.0016) 0.2301(0.0013) C5 - 1.2376(0.0014) -0.7332(0.0019) -0.3819(0.0012) C10 - 1.2867(0.0019) 0.6752(0.0023) 0.1892(0.0013) q2 = 0.5980(0.0018) q3 = -0.0916(0.0018) phi2 = 56.08 (1/5) Total puckering amplitude: QT = 0.6050(0.0017) Spherical polar angles: Theta2 = 98.71 (0.17)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C1 C2 C3 C4 C5 C10

DS(C1) =0.3354(0.0009) DS(C1 –C10) =0.0562(0.0008) D2(C1) =0.1362(0.0006) D2(C1 –C10) =0.3294(0.0007)

DS(C2) =0.0281(0.0009) DS(C2 –C1) =0.3012(0.0008) D2(C2) =0.2369(0.0006) D2(C2 –C1) =0.1449(0.0008)

DS(C3) =0.3635(0.0009) DS(C3 –C2) =0.2786(0.0007) D2(C3) =0.1098(0.0006) D2(C3 –C2) =0.1846(0.0008)

Ring 2 Atom Internal Cartesian coordinates X Y Z C5 0.0000(0.0001) 1.3031(0.0013) -0.1867(0.0009) C6 1.2393(0.0018) 0.3662(0.0019) 0.0276(0.0011) C7 0.6974(0.0017) -1.0765(0.0018) 0.1421(0.0011) C8 - 0.7771(0.0013) -0.9894(0.0014) -0.2575(0.0010) C9 - 1.1597(0.0013) 0.3965(0.0014) 0.2745(0.0010) q2 = 0.4444(0.0016) phi2 = 131.64 (0.21)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C5 C6 C7 C8 C9

DS(C5) =0.2601(0.0009) D2(C5) =0.1692(0.0006) DS(C6) =0.3457(0.0008) D2(C6) =0.0244(0.0006) DS(C7) =0.2993(0.0008) D2(C7) =0.1292(0.0006) DS(C8) =0.1386(0.0008) D2(C8) =0.2329(0.0007) DS(C9) =0.0752(0.0008) D2(C9) =0.2465(0.0006)

Ring 3 Atom Internal Cartesian coordinates X Y Z C8 0.0000(0.0000) 1.4786(0.0012) 0.2328(0.0011) C9 1.2441(0.0014) 0.7030(0.0017) -0.2155(0.0011) C11 1.2757(0.0017) -0.7580(0.0020) 0.2189(0.0012) C12 - 0.0230(0.0017) -1.4554(0.0015) -0.2395(0.0012) C13 - 1.2648(0.0014) -0.7105(0.0016) 0.2568(0.0011) C14 - 1.2320(0.0017) 0.7423(0.0016) -0.2534(0.0011) q2 = 0.0384(0.0015) q3 = 0.5784(0.0016) phi2 = -98.80 (2.42) Total puckering amplitude: QT = 0.5797(0.0016) Spherical polar angles: Theta2 = 3.79 (0.15)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C8 C9 C11 C12 C13 C14

DS(C8) =0.0265(0.0008) DS(C8 –C14) =0.3204(0.0006) D2(C8) =0.2536(0.0005) D2(C8 –C14) =0.0202(0.0006)

DS(C9) =0.0104(0.0008) DS(C9 –C8) =0.3205(0.0006) D2(C9) =0.2531(0.0005) D2(C9 –C8) =0.0177(0.0006)

DS(C11) =0.0163(0.0008) DS(C11 –C9) =0.3210(0.0006) D2(C11) =0.2536(0.0005) D2(C11 –C9) =0.0044(0.0006)

Ring 4 Atom Internal Cartesian coordinates X Y Z C13 0.0000(0.0000) 1.2555(0.0014) -0.2972(0.0010) C14 1.1529(0.0016) 0.4024(0.0018) 0.2640(0.0010) C15 0.7903(0.0013) -1.0317(0.0019) -0.1300(0.0012) C16 - 0.7586(0.0017) -1.0422(0.0020) -0.0537(0.0013) C17 - 1.1847(0.0014) 0.4160(0.0020) 0.2168(0.0011) q2 = 0.4741(0.0015) phi2 = -172.32 (0.24)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C13 C14 C15 C16 C17

DS(C13) =0.0502(0.0009) D2(C13) =0.2699(0.0007) DS(C14) =0.1760(0.0009) D2(C14) =0.2380(0.0007) DS(C15) =0.3349(0.0009) D2(C15) =0.1187(0.0007) DS(C16) =0.3659(0.0009) D2(C16) =0.0486(0.0007) DS(C17) =0.2571(0.0009) D2(C17) =0.1961(0.0007)

Possible hydrogen bonds

Donor-H Donor···Acceptor H···Acceptor Donor-H······Acceptor

C8 –H8 C8 ···O19 (0) H8 ···O19 (0) C8 –H8 ···O19 (0) 0.967(.019) 3.139(.002) 2.531(.018) 120.87(1.30)

C11 –H11B C11 ···O19 (0) H11B ···O19 (0) C11 –H11B ···O19 (0) 1.014(.018) 3.115(.002) 2.492(.018) 119.20(1.30)

C18 –H20C C18 ···O21 (0) H20C ···O21 (0) C18 –H20C ···O21 (0) 0.981(.025) 2.816(.002) 2.562(.023) 94.65(1.41)

C4 –H4B C4 ···O19 (1) H4B ···O19 (1) C4 –H4B ···O19 (1) 0.948(.024) 3.388(.002) 2.767(.023) 123.79(1.76)

C1 –H1A C1 ···O19 (1) H1A ···O19 (1) C1 –H1A ···O19 (1) 0.990(.022) 3.130(.002) 2.430(.022) 127.24(1.63)

C6 –H6B C6 ···O20 (2) H6B ···O20 (2) C6 –H6B ···O20 (2) 1.015(.022) 3.632(.002) 2.714(.023) 150.66(1.69)

C1 –H1B C1 ···O20 (2) H1B ···O20 (2) C1 –H1B ···O20 (2) 0.969(.023) 3.660(.002) 2.868(.023) 139.47(1.77)

C7 –H7A C7 ···O20 (3) H7A ···O20 (3) C7 –H7A ···O20 (3) 0.995(.019) 3.542(.002) 2.822(.019) 129.79(1.40)

C7 –H7A C7 ···O21 (4) H7A ···O21 (4) C7 –H7A ···O21 (4) 0.995(.019) 3.812(.002) 2.867(.019) 158.73(1.47)

O21 –H21 O21 ···O20 (5) H21 ···O20 (5) O21 –H21 ···O20 (5) 0.819(.024) 2.863(.002) 2.047(.024) 173.94(2.34)

Number of possible hydrogen bonds 10

Equivalent positions: (0) x,y,z (1) x - 1/2,-y + 1/2,-z + 1 (2) x + 1,+y,+z (3) x + 1/2,-y - 1/2,-z + 1 (4) -x,+y - 1/2,-z + 1/2 (5) -x - 1/2,-y,+z - 1/2

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O190.1030 (3)0.19403 (14)0.47279 (6)0.0569 (4)
O200.5437 (2)0.03301 (17)0.56061 (6)0.0551 (4)
O210.1927 (3)0.12774 (15)0.17262 (5)0.0534 (4)
C10.0470 (3)0.11623 (19)0.56149 (7)0.0383 (4)
C20.2020 (3)0.0201 (2)0.58502 (7)0.0424 (4)
C30.3757 (3)0.00555 (16)0.54299 (7)0.0362 (3)
C40.3315 (2)0.00163 (19)0.47690 (7)0.0353 (3)
C50.1060 (2)0.00540 (14)0.45926 (6)0.0270 (3)
C60.0112 (3)0.12198 (17)0.47397 (7)0.0373 (4)
C70.1479 (3)0.15174 (16)0.41949 (7)0.0344 (3)
C80.1384 (2)0.03157 (14)0.38011 (6)0.0257 (3)
C90.0801 (2)0.01390 (15)0.39076 (6)0.0264 (3)
C100.0064 (3)0.11301 (16)0.49474 (7)0.0332 (3)
C110.1399 (3)0.13468 (17)0.35637 (7)0.0348 (3)
C120.0963 (3)0.11458 (18)0.28913 (7)0.0350 (3)
C130.1244 (2)0.07441 (14)0.27837 (6)0.0280 (3)
C140.1701 (2)0.04966 (15)0.31347 (6)0.0271 (3)
C150.3764 (3)0.09394 (19)0.28954 (7)0.0378 (4)
C160.3706 (3)0.0527 (2)0.22287 (7)0.0424 (4)
C170.1735 (3)0.02574 (17)0.21490 (7)0.0359 (3)
C180.2685 (3)0.18544 (18)0.29372 (8)0.0377 (4)
H1A0.099 (3)0.204 (2)0.5700 (9)0.049 (6)*
H1B0.085 (4)0.105 (2)0.5799 (10)0.057 (6)*
H2A0.249 (4)0.043 (2)0.6212 (10)0.053 (6)*
H2B0.141 (4)0.067 (2)0.5914 (10)0.058 (7)*
H4A0.410 (4)0.073 (2)0.4592 (10)0.054 (6)*
H4B0.391 (4)0.079 (2)0.4628 (10)0.059 (7)*
H6A0.084 (3)0.191 (2)0.4782 (10)0.054 (6)*
H6B0.102 (3)0.111 (2)0.5103 (10)0.053 (6)*
H7A0.091 (3)0.2261 (19)0.3971 (8)0.039 (5)*
H7B0.289 (4)0.173 (2)0.4326 (9)0.053 (6)*
H80.228 (3)0.0330 (18)0.3964 (7)0.031 (5)*
H90.167 (3)0.0544 (18)0.3737 (8)0.034 (5)*
H11A0.285 (3)0.155 (2)0.3603 (9)0.049 (6)*
H11B0.061 (3)0.2109 (17)0.3726 (8)0.036 (5)*
H12A0.186 (4)0.046 (2)0.2742 (9)0.052 (6)*
H12B0.129 (3)0.192 (2)0.2681 (8)0.039 (5)*
H140.068 (3)0.1142 (17)0.3010 (8)0.029 (4)*
H15A0.408 (3)0.1849 (19)0.2948 (9)0.041 (5)*
H15B0.491 (3)0.0506 (18)0.3115 (8)0.033 (5)*
H16A0.375 (4)0.126 (2)0.1970 (10)0.064 (7)*
H16B0.485 (4)0.002 (2)0.2131 (10)0.059 (7)*
H170.056 (3)0.0275 (17)0.2028 (8)0.030 (4)*
H20A0.409 (4)0.164 (3)0.2851 (12)0.068 (8)*
H20B0.252 (4)0.209 (2)0.3355 (10)0.059 (6)*
H20C0.246 (4)0.260 (3)0.2679 (10)0.064 (7)*
H210.154 (4)0.095 (2)0.1411 (11)0.059 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O190.0715 (10)0.0547 (8)0.0444 (7)0.0322 (8)0.0118 (7)0.0098 (6)
O200.0423 (7)0.0836 (10)0.0395 (6)0.0083 (8)0.0123 (6)0.0056 (7)
O210.0760 (10)0.0593 (8)0.0249 (5)0.0094 (9)0.0026 (6)0.0077 (6)
C10.0395 (8)0.0482 (10)0.0274 (7)0.0020 (8)0.0029 (6)0.0064 (7)
C20.0489 (10)0.0548 (11)0.0234 (7)0.0028 (9)0.0026 (7)0.0009 (7)
C30.0384 (8)0.0395 (8)0.0306 (7)0.0005 (8)0.0065 (6)0.0019 (6)
C40.0319 (7)0.0483 (9)0.0257 (6)0.0070 (8)0.0027 (6)0.0010 (7)
C50.0284 (6)0.0308 (7)0.0217 (5)0.0020 (6)0.0014 (5)0.0011 (5)
C60.0492 (9)0.0350 (8)0.0277 (6)0.0031 (8)0.0043 (7)0.0067 (6)
C70.0399 (8)0.0322 (7)0.0311 (7)0.0057 (7)0.0023 (7)0.0048 (6)
C80.0263 (6)0.0282 (7)0.0227 (6)0.0006 (6)0.0004 (5)0.0000 (5)
C90.0262 (6)0.0312 (7)0.0218 (6)0.0001 (6)0.0005 (5)0.0007 (5)
C100.0344 (7)0.0355 (7)0.0296 (6)0.0022 (7)0.0006 (6)0.0032 (6)
C110.0355 (8)0.0393 (8)0.0296 (7)0.0099 (7)0.0038 (6)0.0067 (6)
C120.0338 (8)0.0438 (8)0.0272 (7)0.0052 (7)0.0017 (6)0.0083 (7)
C130.0294 (7)0.0330 (7)0.0216 (5)0.0031 (6)0.0019 (5)0.0010 (5)
C140.0263 (6)0.0313 (7)0.0237 (6)0.0010 (6)0.0007 (5)0.0016 (5)
C150.0350 (8)0.0470 (9)0.0313 (7)0.0060 (8)0.0052 (7)0.0016 (7)
C160.0446 (10)0.0531 (10)0.0294 (7)0.0017 (9)0.0098 (7)0.0045 (7)
C170.0412 (8)0.0439 (9)0.0226 (6)0.0076 (8)0.0012 (6)0.0024 (6)
C180.0443 (10)0.0380 (8)0.0308 (7)0.0115 (7)0.0004 (7)0.0006 (7)
Geometric parameters (Å, º) top
O19—C101.212 (2)C8—C91.533 (2)
O20—C31.208 (2)C8—H80.967 (19)
O21—C171.426 (2)C9—C111.525 (2)
O21—H210.82 (2)C9—H90.990 (19)
C1—C101.516 (2)C11—C121.544 (2)
C1—C21.522 (3)C11—H11A0.98 (2)
C1—H1A0.99 (2)C11—H11B1.014 (19)
C1—H1B0.97 (2)C12—C131.531 (2)
C2—C31.504 (3)C12—H12A0.99 (2)
C2—H2A0.90 (2)C12—H12B0.95 (2)
C2—H2B1.00 (2)C13—C181.534 (2)
C3—C41.507 (2)C13—C141.540 (2)
C4—C51.537 (2)C13—C171.540 (2)
C4—H4A1.01 (2)C14—C151.531 (2)
C4—H4B0.95 (2)C14—H140.991 (18)
C5—C101.521 (2)C15—C161.551 (2)
C5—C91.5424 (19)C15—H15A0.98 (2)
C5—C61.568 (2)C15—H15B1.006 (19)
C6—C71.545 (2)C16—C171.543 (3)
C6—H6A0.96 (2)C16—H16A0.96 (2)
C6—H6B1.01 (2)C16—H16B0.97 (2)
C7—C81.530 (2)C17—H170.991 (19)
C7—H7A0.995 (19)C18—H20A0.97 (3)
C7—H7B1.00 (2)C18—H20B0.97 (2)
C8—C141.5154 (18)C18—H20C0.98 (3)
C17—O21—H21103.7 (17)O19—C10—C1119.18 (15)
C10—C1—C2116.33 (14)O19—C10—C5123.86 (14)
C10—C1—H1A105.6 (12)C1—C10—C5116.96 (14)
C2—C1—H1A107.9 (13)C9—C11—C12109.32 (13)
C10—C1—H1B104.8 (13)C9—C11—H11A112.3 (13)
C2—C1—H1B112.3 (14)C12—C11—H11A107.2 (12)
H1A—C1—H1B110 (2)C9—C11—H11B109.4 (10)
C3—C2—C1114.27 (14)C12—C11—H11B111.0 (10)
C3—C2—H2A110.2 (15)H11A—C11—H11B107.6 (17)
C1—C2—H2A111.6 (15)C13—C12—C11111.48 (13)
C3—C2—H2B103.5 (14)C13—C12—H12A108.5 (13)
C1—C2—H2B112.0 (14)C11—C12—H12A108.4 (12)
H2A—C2—H2B104.5 (19)C13—C12—H12B111.5 (12)
O20—C3—C2122.34 (14)C11—C12—H12B108.8 (12)
O20—C3—C4120.51 (15)H12A—C12—H12B108.0 (17)
C2—C3—C4117.15 (14)C12—C13—C18110.28 (14)
C3—C4—C5116.05 (13)C12—C13—C14109.54 (13)
C3—C4—H4A104.3 (13)C18—C13—C14113.36 (13)
C5—C4—H4A114.5 (14)C12—C13—C17115.70 (13)
C3—C4—H4B106.8 (14)C18—C13—C17108.88 (13)
C5—C4—H4B107.0 (16)C14—C13—C1798.75 (12)
H4A—C4—H4B107.8 (18)C8—C14—C15120.19 (13)
C10—C5—C4107.56 (13)C8—C14—C13111.67 (12)
C10—C5—C9115.31 (12)C15—C14—C13104.35 (12)
C4—C5—C9111.26 (12)C8—C14—H14105.5 (10)
C10—C5—C6107.50 (12)C15—C14—H14107.5 (10)
C4—C5—C6113.58 (13)C13—C14—H14107.0 (10)
C9—C5—C6101.66 (11)C14—C15—C16103.31 (14)
C7—C6—C5106.90 (12)C14—C15—H15A116.1 (12)
C7—C6—H6A108.0 (13)C16—C15—H15A112.9 (12)
C5—C6—H6A109.5 (13)C14—C15—H15B111.1 (10)
C7—C6—H6B107.9 (12)C16—C15—H15B111.3 (10)
C5—C6—H6B111.4 (12)H15A—C15—H15B102.4 (16)
H6A—C6—H6B112.9 (17)C17—C16—C15106.14 (13)
C8—C7—C6105.39 (13)C17—C16—H16A112.1 (15)
C8—C7—H7A109.2 (11)C15—C16—H16A111.1 (14)
C6—C7—H7A109.4 (11)C17—C16—H16B108.4 (13)
C8—C7—H7B112.9 (13)C15—C16—H16B111.2 (14)
C6—C7—H7B110.8 (12)H16A—C16—H16B107.9 (19)
H7A—C7—H7B109.0 (17)O21—C17—C16113.29 (15)
C14—C8—C7117.26 (12)O21—C17—C13112.57 (14)
C14—C8—C9108.68 (11)C16—C17—C13104.13 (12)
C7—C8—C9101.61 (12)O21—C17—H17107.7 (10)
C14—C8—H8111.8 (10)C16—C17—H17113.3 (11)
C7—C8—H8109.0 (10)C13—C17—H17105.7 (10)
C9—C8—H8107.6 (11)C13—C18—H20A111.7 (16)
C11—C9—C8114.72 (12)C13—C18—H20B109.4 (14)
C11—C9—C5121.26 (13)H20A—C18—H20B111 (2)
C8—C9—C5103.89 (11)C13—C18—H20C111.9 (14)
C11—C9—H9104.3 (11)H20A—C18—H20C102 (2)
C8—C9—H9105.3 (11)H20B—C18—H20C110.5 (19)
C5—C9—H9106.1 (10)
C10—C1—C2—C335.3 (2)C9—C5—C10—C1173.64 (14)
C1—C2—C3—O20149.19 (19)C6—C5—C10—C173.80 (17)
C1—C2—C3—C432.0 (2)C8—C9—C11—C1253.84 (18)
O20—C3—C4—C5166.03 (17)C5—C9—C11—C12179.89 (13)
C2—C3—C4—C512.8 (2)C9—C11—C12—C1354.33 (19)
C3—C4—C5—C1052.31 (19)C11—C12—C13—C1867.68 (18)
C3—C4—C5—C9179.49 (14)C11—C12—C13—C1457.74 (17)
C3—C4—C5—C666.53 (19)C11—C12—C13—C17168.22 (14)
C10—C5—C6—C7103.93 (15)C7—C8—C14—C1566.1 (2)
C4—C5—C6—C7137.20 (14)C9—C8—C14—C15179.53 (14)
C9—C5—C6—C717.59 (16)C7—C8—C14—C13171.27 (13)
C5—C6—C7—C810.05 (18)C9—C8—C14—C1356.86 (15)
C6—C7—C8—C14152.13 (14)C12—C13—C14—C859.65 (15)
C6—C7—C8—C933.86 (16)C18—C13—C14—C863.97 (17)
C14—C8—C9—C1155.18 (16)C17—C13—C14—C8179.00 (13)
C7—C8—C9—C11179.44 (13)C12—C13—C14—C15169.03 (13)
C14—C8—C9—C5170.21 (12)C18—C13—C14—C1567.35 (16)
C7—C8—C9—C545.94 (14)C17—C13—C14—C1547.68 (14)
C10—C5—C9—C1153.97 (19)C8—C14—C15—C16159.99 (14)
C4—C5—C9—C1168.87 (19)C13—C14—C15—C1633.84 (17)
C6—C5—C9—C11169.90 (14)C14—C15—C16—C176.3 (2)
C10—C5—C9—C876.88 (16)C15—C16—C17—O21145.84 (15)
C4—C5—C9—C8160.28 (13)C15—C16—C17—C1323.21 (19)
C6—C5—C9—C839.05 (14)C12—C13—C17—O2177.40 (19)
C2—C1—C10—O19174.09 (18)C18—C13—C17—O2147.42 (19)
C2—C1—C10—C56.5 (2)C14—C13—C17—O21165.89 (14)
C4—C5—C10—O19131.77 (18)C12—C13—C17—C16159.50 (14)
C9—C5—C10—O197.0 (2)C18—C13—C17—C1675.68 (17)
C6—C5—C10—O19105.57 (19)C14—C13—C17—C1642.78 (15)
C4—C5—C10—C148.86 (19)
(III) (5R,9R,17S)-9(105)-abeo-4,5-dihydroestrene-17-hydroxy-3,10-dione top
Crystal data top
C18H26O3Dx = 1.234 Mg m3
Mr = 290.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 60 reflections
a = 6.6278 (5) Åθ = 3.7–12.5°
b = 11.1491 (9) ŵ = 0.08 mm1
c = 21.1609 (19) ÅT = 293 K
V = 1563.7 (2) Å3Squared prism, colourless
Z = 40.34 × 0.24 × 0.22 mm
F(000) = 632
Data collection top
Bruker P4
diffractometer
Rint = 0.026
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 1.9°
Graphite monochromatorh = 08
2θ/ω scansk = 014
4127 measured reflectionsl = 027
2094 independent reflections3 standard reflections every 197 reflections
1400 reflections with I > 2σ(I) intensity decay: 0.0%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0478P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.002
S = 0.96Δρmax = 0.12 e Å3
2094 reflectionsΔρmin = 0.13 e Å3
295 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.011 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: based on the reagents configuration
Secondary atom site location: difference Fourier map
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Ring puckering coordinates following Cremer D. & Pople J·A., JACS (1975).97,1354

Ring 1 Atom Internal Cartesian coordinates X Y Z C1 0.0000(0.0000) 1.3958(0.0025) 0.3440(0.0022) C2 1.2386(0.0035) 0.7610(0.0032) -0.2791(0.0022) C3 1.2864(0.0025) -0.7216(0.0035) -0.0767(0.0020) C4 - 0.0002(0.0036) -1.3718(0.0021) 0.3677(0.0018) C5 - 1.2426(0.0026) -0.7832(0.0031) -0.3029(0.0019) C10 - 1.2821(0.0034) 0.7199(0.0035) -0.0530(0.0020) q2 = 0.6565(0.0029) q3 = -0.0291(0.0029) phi2 = 20.15 (0.24) Total puckering amplitude: QT = 0.6571(0.0029) Spherical polar angles: Theta2 = 92.54 (0.26)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C1 C2 C3 C4 C5 C10

DS(C1) =0.1513(0.0014) DS(C1 –C10) =0.2398(0.0012) D2(C1) =0.2445(0.0009) D2(C1 –C10) =0.2809(0.0012)

DS(C2) =0.2931(0.0014) DS(C2 –C1) =0.3632(0.0012) D2(C2) =0.2007(0.0009) D2(C2 –C1) =0.0672(0.0011)

DS(C3) =0.4443(0.0015) DS(C3 –C2) =0.1246(0.0011) D2(C3) =0.0508(0.0009) D2(C3 –C2) =0.3477(0.0012)

Ring 2 Atom Internal Cartesian coordinates X Y Z C5 0.0000(0.0000) 1.2787(0.0020) 0.2566(0.0016) C6 1.1788(0.0032) 0.4102(0.0031) -0.2392(0.0019) C7 0.7876(0.0027) -1.0203(0.0033) 0.1304(0.0019) C8 - 0.7603(0.0027) -1.0741(0.0028) 0.0283(0.0018) C9 - 1.2061(0.0025) 0.4055(0.0031) -0.1761(0.0016) q2 = 0.4146(0.0027) phi2 = 11.81 (0.39)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C5 C6 C7 C8 C9

DS(C5) =0.0666(0.0014) D2(C5) =0.2305(0.0011) DS(C6) =0.1311(0.0013) D2(C6) =0.2139(0.0011) DS(C7) =0.2788(0.0013) D2(C7) =0.1176(0.0011) DS(C8) =0.3199(0.0014) D2(C8) =0.0249(0.0011) DS(C9) =0.2389(0.0015) D2(C9) =0.1572(0.0010)

Ring 3 Atom Internal Cartesian coordinates X Y Z C8 0.0000(0.0000) 1.5249(0.0023) 0.1002(0.0018) C9 1.3231(0.0028) 0.7132(0.0033) -0.0420(0.0019) C11 1.2467(0.0026) -0.8063(0.0032) 0.1236(0.0021) C12 - 0.0779(0.0028) -1.4573(0.0026) -0.2634(0.0020) C13 - 1.2559(0.0020) -0.6988(0.0030) 0.3215(0.0016) C14 - 1.2360(0.0028) 0.7242(0.0031) -0.2399(0.0017) q2 = 0.2432(0.0025) q3 = 0.4452(0.0026) phi2 = -125.53 (2/3) Total puckering amplitude: QT = 0.5073(0.0024) Spherical polar angles: Theta2 = 28.64 (0.30)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C8 C9 C11 C12 C13 C14

DS(C8) =0.1363(0.0013) DS(C8 –C14) =0.2461(0.0011) D2(C8) =0.2024(0.0009) D2(C8 –C14) =0.1355(0.0010)

DS(C9) =0.0151(0.0013) DS(C9 –C8) =0.2751(0.0011) D2(C9) =0.2168(0.0009) D2(C9 –C8) =0.0572(0.0011)

DS(C11) =0.1512(0.0013) DS(C11 –C9) =0.2699(0.0010) D2(C11) =0.1981(0.0008) D2(C11 –C9) =0.0783(0.0011)

Ring 4 Atom Internal Cartesian coordinates X Y Z C13 0.0000(0.0000) 1.2491(0.0022) -0.2913(0.0016) C14 1.1603(0.0025) 0.4119(0.0030) 0.2501(0.0016) C15 0.7789(0.0028) -1.0272(0.0032) -0.1134(0.0018) C16 - 0.7591(0.0027) -1.0420(0.0030) -0.0667(0.0019) C17 - 1.1801(0.0026) 0.4082(0.0031) 0.2212(0.0018) q2 = 0.4622(0.0026) phi2 = -175.18 (0.37)

Asymmetry parameters Following Nardelli M., Acta Cryst.(1983). C39, 1141

C13 C14 C15 C16 C17

DS(C13) =0.0308(0.0015) D2(C13) =0.2649(0.0011) DS(C14) =0.1879(0.0015) D2(C14) =0.2264(0.0011) DS(C15) =0.3347(0.0014) D2(C15) =0.1036(0.0011) DS(C16) =0.3538(0.0014) D2(C16) =0.0605(0.0011) DS(C17) =0.2377(0.0014) D2(C17) =0.2005(0.0011)

Possible hydrogen bonds Donor-H Donor···Acceptor H···Acceptor Donor-H······Acceptor

C6 –H6B C6 ···O19 (0) H6B ···O19 (0) C6 –H6B ···O19 (0) 0.947(.036) 3.149(.004) 2.793(.035) 103.33(2.33)

C9 –H9 C9 ···O19 (0) H9 ···O19 (0) C9 –H9 ···O19 (0) 0.910(.029) 2.874(.003) 2.423(.027) 110.66(1.98)

C18 –H18B C18 ···O21 (0) H18B ···O21 (0) C18 –H18B ···O21 (0) 0.951(.039) 2.925(.004) 2.661(.038) 96.45(2.53)

C11 –H11B C11 ···O19 (1) H11B ···O19 (1) C11 –H11B ···O19 (1) 0.932(.028) 3.469(.004) 2.552(.028) 168.23(2.29)

C1 –H1B C1 ···O19 (1) H1B ···O19 (1) C1 –H1B ···O19 (1) 1.027(.029) 3.567(.004) 2.695(.028) 142.82(2.11)

C2 –H2A C2 ···O21 (2) H2A ···O21 (2) C2 –H2A ···O21 (2) 0.931(.039) 3.459(.004) 2.605(.037) 152.73(3.06)

C2 –H2B C2 ···O20 (3) H2B ···O20 (3) C2 –H2B ···O20 (3) 0.944(.034) 3.685(.004) 2.796(.034) 157.36(2.69)

C6 –H6A C6 ···O20 (3) H6A ···O20 (3) C6 –H6A ···O20 (3) 0.983(.034) 3.585(.004) 2.645(.033) 160.09(2.65)

C7 –H7A C7 ···O21 (4) H7A ···O21 (4) C7 –H7A ···O21 (4) 1.077(.027) 3.719(.004) 2.731(.027) 152.34(1.95)

C4 –H4B C4 ···O21 (4) H4B ···O21 (4) C4 –H4B ···O21 (4) 0.978(.028) 3.633(.004) 2.968(.027) 126.26(1.98)

C7 –H7B C7 ···O20 (5) H7B ···O20 (5) C7 –H7B ···O20 (5) 0.970(.032) 3.672(.004) 2.914(.030) 135.79(2.31)

C16 –H16B C16 ···O20 (6) H16B ···O20 (6) C16 –H16B ···O20 (6) 1.014(.027) 3.743(.004) 2.959(.027) 134.85(1.91)

O21 –H21 O21 ···O20 (6) H21 ···O20 (6) O21 –H21 ···O20 (6) 0.915(.042) 2.862(.003) 2.033(.038) 150.04(3.40)

Number of possible hydrogen bonds 13

Equivalent positions: (0) x,y,z (1) x - 1/2,-y + 1/2,-z (2) -x - 1/2,-y + 1,+z - 1/2 (3) x + 1/2,-y + 1/2 + 1,-z (4) -x,+y + 1/2,-z + 1/2 (5) x + 1,+y,+z (6) -x,+y - 1/2,-z + 1/2

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O190.1626 (4)0.3088 (2)0.02593 (9)0.0874 (8)
O200.1972 (3)0.71231 (16)0.05072 (8)0.0640 (6)
O210.0468 (4)0.3123 (2)0.35090 (9)0.0753 (7)
C10.1000 (5)0.4460 (2)0.04383 (13)0.0573 (7)
C20.1275 (6)0.5806 (3)0.03453 (13)0.0554 (7)
C30.1371 (4)0.6152 (2)0.03377 (11)0.0453 (6)
C40.0671 (4)0.5215 (2)0.08033 (11)0.0450 (7)
C50.1175 (4)0.4512 (2)0.05785 (10)0.0448 (6)
C60.3049 (5)0.5331 (3)0.05274 (14)0.0579 (7)
C70.3777 (5)0.5483 (3)0.12081 (15)0.0589 (7)
C80.3248 (4)0.4291 (2)0.15490 (12)0.0486 (6)
C90.1918 (4)0.3580 (2)0.10705 (11)0.0479 (6)
C100.0715 (5)0.3945 (2)0.00610 (12)0.0539 (7)
C110.0315 (5)0.2734 (2)0.13390 (13)0.0556 (8)
C120.0559 (4)0.3078 (3)0.19812 (12)0.0507 (7)
C130.1097 (4)0.3416 (2)0.24440 (10)0.0423 (6)
C140.2227 (4)0.4501 (2)0.21781 (11)0.0417 (5)
C150.3491 (5)0.4948 (3)0.27369 (14)0.0601 (7)
C160.2222 (5)0.4638 (3)0.33235 (13)0.0652 (8)
C170.0375 (5)0.3951 (3)0.30742 (12)0.0545 (7)
C180.2494 (6)0.2336 (3)0.25718 (15)0.0602 (8)
H1A0.087 (4)0.421 (2)0.0866 (13)0.057 (7)*
H1B0.221 (5)0.402 (3)0.0244 (13)0.064 (8)*
H2A0.241 (6)0.615 (3)0.0527 (16)0.100 (13)*
H2B0.012 (5)0.621 (3)0.0499 (14)0.072 (10)*
H4A0.175 (4)0.465 (2)0.0845 (11)0.049 (7)*
H4B0.036 (4)0.556 (2)0.1217 (13)0.057 (7)*
H6A0.275 (5)0.609 (3)0.0310 (15)0.088 (11)*
H6B0.399 (6)0.489 (3)0.0283 (17)0.104 (13)*
H7A0.298 (4)0.618 (2)0.1455 (12)0.064 (8)*
H7B0.521 (5)0.565 (3)0.1224 (13)0.063 (8)*
H80.452 (4)0.380 (2)0.1631 (10)0.047 (7)*
H90.270 (5)0.308 (3)0.0836 (12)0.069 (9)*
H11A0.100 (5)0.189 (3)0.1376 (12)0.075 (9)*
H11B0.075 (5)0.263 (2)0.1058 (12)0.054 (8)*
H12A0.131 (5)0.240 (3)0.2148 (12)0.060 (8)*
H12B0.149 (4)0.378 (2)0.1954 (11)0.048 (7)*
H140.119 (3)0.5106 (18)0.2115 (9)0.031 (5)*
H15A0.403 (5)0.580 (3)0.2712 (14)0.082 (9)*
H15B0.475 (4)0.446 (2)0.2730 (11)0.057 (7)*
H16A0.178 (5)0.536 (3)0.3564 (14)0.085 (10)*
H16B0.302 (4)0.407 (2)0.3599 (12)0.068 (8)*
H170.069 (4)0.451 (2)0.2980 (10)0.039 (6)*
H18A0.355 (5)0.252 (2)0.2880 (13)0.066 (9)*
H18B0.167 (6)0.172 (3)0.2744 (17)0.109 (13)*
H18C0.311 (5)0.207 (3)0.2181 (13)0.071 (9)*
H210.057 (7)0.272 (3)0.3698 (16)0.113 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O190.121 (2)0.0855 (15)0.0552 (11)0.0414 (16)0.0129 (13)0.0148 (11)
O200.0903 (15)0.0489 (10)0.0529 (10)0.0220 (11)0.0075 (11)0.0006 (9)
O210.0834 (16)0.0901 (16)0.0523 (12)0.0005 (14)0.0113 (12)0.0199 (11)
C10.079 (2)0.0490 (15)0.0435 (15)0.0022 (17)0.0000 (15)0.0056 (12)
C20.073 (2)0.0505 (15)0.0427 (14)0.0045 (17)0.0024 (15)0.0003 (12)
C30.0518 (15)0.0415 (13)0.0426 (12)0.0013 (13)0.0007 (12)0.0028 (11)
C40.0525 (17)0.0474 (15)0.0350 (13)0.0098 (14)0.0049 (12)0.0032 (11)
C50.0523 (14)0.0445 (13)0.0376 (11)0.0100 (14)0.0092 (11)0.0031 (11)
C60.0549 (17)0.0599 (18)0.0589 (17)0.0040 (16)0.0145 (15)0.0138 (15)
C70.0437 (15)0.0634 (18)0.0696 (18)0.0097 (16)0.0063 (14)0.0114 (16)
C80.0370 (13)0.0518 (15)0.0569 (14)0.0077 (12)0.0036 (12)0.0113 (12)
C90.0566 (16)0.0402 (13)0.0468 (13)0.0115 (13)0.0109 (13)0.0000 (11)
C100.0702 (18)0.0484 (14)0.0431 (14)0.0047 (16)0.0134 (14)0.0019 (12)
C110.076 (2)0.0397 (15)0.0513 (15)0.0057 (15)0.0082 (16)0.0014 (12)
C120.0503 (17)0.0505 (15)0.0512 (15)0.0128 (15)0.0015 (13)0.0103 (13)
C130.0451 (14)0.0399 (12)0.0419 (12)0.0035 (12)0.0003 (11)0.0045 (10)
C140.0366 (12)0.0362 (11)0.0524 (13)0.0036 (11)0.0044 (11)0.0081 (11)
C150.0562 (18)0.0548 (17)0.0693 (18)0.0057 (15)0.0172 (16)0.0013 (14)
C160.085 (2)0.0580 (18)0.0521 (15)0.0044 (18)0.0140 (16)0.0022 (15)
C170.0605 (17)0.0577 (16)0.0454 (14)0.0103 (16)0.0046 (13)0.0076 (13)
C180.074 (2)0.0475 (16)0.0595 (17)0.0137 (16)0.0058 (18)0.0069 (14)
Geometric parameters (Å, º) top
O19—C101.206 (3)C8—C91.559 (4)
O20—C31.208 (3)C8—H81.02 (2)
O21—C171.418 (3)C9—C111.530 (4)
O21—H210.91 (4)C9—H90.91 (3)
C1—C101.503 (4)C11—C121.526 (4)
C1—C21.525 (4)C11—H11A1.05 (3)
C1—H1A0.95 (3)C11—H11B0.93 (3)
C1—H1B1.03 (3)C12—C131.518 (3)
C2—C31.497 (4)C12—H12A0.97 (3)
C2—H2A0.93 (4)C12—H12B1.00 (3)
C2—H2B0.94 (3)C13—C141.530 (3)
C3—C41.509 (3)C13—C171.537 (3)
C4—C51.530 (3)C13—C181.543 (4)
C4—H4A0.95 (3)C14—C151.533 (4)
C4—H4B0.98 (3)C14—H140.97 (2)
C5—C101.524 (3)C15—C161.539 (5)
C5—C61.546 (4)C15—H15A1.01 (3)
C5—C91.551 (3)C15—H15B1.00 (3)
C6—C71.528 (4)C16—C171.537 (4)
C6—H6A0.98 (3)C16—H16A0.99 (3)
C6—H6B0.95 (4)C16—H16B1.01 (3)
C7—C81.552 (4)C17—H170.97 (2)
C7—H7A1.08 (3)C18—H18A0.98 (3)
C7—H7B0.97 (3)C18—H18B0.95 (4)
C8—C141.511 (3)C18—H18C0.97 (3)
C17—O21—H21108 (2)O19—C10—C1119.8 (2)
C10—C1—C2113.4 (3)O19—C10—C5122.5 (3)
C10—C1—H1A108.9 (16)C1—C10—C5117.7 (2)
C2—C1—H1A114.9 (15)C12—C11—C9116.1 (2)
C10—C1—H1B101.4 (15)C12—C11—H11A108.9 (15)
C2—C1—H1B108.8 (16)C9—C11—H11A106.3 (17)
H1A—C1—H1B108 (2)C12—C11—H11B108.2 (16)
C3—C2—C1112.5 (2)C9—C11—H11B111.6 (16)
C3—C2—H2A105 (2)H11A—C11—H11B105 (2)
C1—C2—H2A117 (2)C13—C12—C11111.3 (2)
C3—C2—H2B104.2 (19)C13—C12—H12A109.2 (16)
C1—C2—H2B109 (2)C11—C12—H12A108.9 (16)
H2A—C2—H2B108 (3)C13—C12—H12B107.0 (14)
O20—C3—C2122.1 (2)C11—C12—H12B112.4 (14)
O20—C3—C4121.8 (2)H12A—C12—H12B108 (2)
C2—C3—C4116.1 (2)C12—C13—C14108.25 (19)
C3—C4—C5113.4 (2)C12—C13—C17115.5 (2)
C3—C4—H4A106.6 (14)C14—C13—C1799.49 (19)
C5—C4—H4A106.8 (15)C12—C13—C18110.7 (2)
C3—C4—H4B112.3 (16)C14—C13—C18112.8 (2)
C5—C4—H4B108.0 (16)C17—C13—C18109.7 (2)
H4A—C4—H4B110 (2)C8—C14—C13114.9 (2)
C10—C5—C4109.2 (2)C8—C14—C15119.0 (2)
C10—C5—C6110.1 (2)C13—C14—C15104.0 (2)
C4—C5—C6111.2 (2)C8—C14—H14107.6 (12)
C10—C5—C9112.5 (2)C13—C14—H14104.8 (12)
C4—C5—C9112.88 (19)C15—C14—H14105.4 (12)
C6—C5—C9100.8 (2)C14—C15—C16104.5 (2)
C7—C6—C5104.7 (2)C14—C15—H15A117.1 (17)
C7—C6—H6A114.1 (19)C16—C15—H15A116.3 (18)
C5—C6—H6A112 (2)C14—C15—H15B105.5 (15)
C7—C6—H6B111 (2)C16—C15—H15B110.2 (15)
C5—C6—H6B105 (2)H15A—C15—H15B103 (2)
H6A—C6—H6B109 (3)C17—C16—C15105.7 (2)
C6—C7—C8105.8 (2)C17—C16—H16A110 (2)
C6—C7—H7A112.6 (14)C15—C16—H16A113.1 (17)
C8—C7—H7A106.6 (13)C17—C16—H16B107.5 (15)
C6—C7—H7B111.3 (17)C15—C16—H16B108.7 (15)
C8—C7—H7B111.5 (17)H16A—C16—H16B111 (2)
H7A—C7—H7B109 (2)O21—C17—C16114.6 (2)
C14—C8—C7112.2 (2)O21—C17—C13115.7 (2)
C14—C8—C9113.4 (2)C16—C17—C13104.1 (2)
C7—C8—C9105.1 (2)O21—C17—H17105.6 (14)
C14—C8—H8107.7 (13)C16—C17—H17109.2 (13)
C7—C8—H8110.8 (13)C13—C17—H17107.4 (13)
C9—C8—H8107.6 (13)C13—C18—H18A112.7 (17)
C11—C9—C5116.2 (2)C13—C18—H18B107 (2)
C11—C9—C8117.7 (2)H18A—C18—H18B108 (3)
C5—C9—C8105.99 (19)C13—C18—H18C110.3 (17)
C11—C9—H9102.6 (19)H18A—C18—H18C109 (2)
C5—C9—H9103.0 (17)H18B—C18—H18C110 (3)
C8—C9—H9110.2 (19)
C10—C1—C2—C350.9 (4)C6—C5—C10—C1102.9 (3)
C1—C2—C3—O20165.2 (3)C9—C5—C10—C1145.6 (2)
C1—C2—C3—C414.9 (4)C5—C9—C11—C1298.2 (3)
O20—C3—C4—C5141.0 (3)C8—C9—C11—C1229.0 (4)
C2—C3—C4—C538.9 (4)C9—C11—C12—C1346.6 (3)
C3—C4—C5—C1055.9 (3)C11—C12—C13—C1461.0 (3)
C3—C4—C5—C665.7 (3)C11—C12—C13—C17171.5 (2)
C3—C4—C5—C9178.2 (2)C11—C12—C13—C1863.0 (3)
C10—C5—C6—C7161.0 (2)C7—C8—C14—C13162.1 (2)
C4—C5—C6—C777.9 (3)C9—C8—C14—C1343.2 (3)
C9—C5—C6—C742.0 (3)C7—C8—C14—C1573.7 (3)
C5—C6—C7—C832.1 (3)C9—C8—C14—C15167.3 (2)
C6—C7—C8—C14132.6 (2)C12—C13—C14—C861.2 (3)
C6—C7—C8—C98.9 (3)C17—C13—C14—C8177.8 (2)
C10—C5—C9—C1173.7 (3)C18—C13—C14—C861.6 (3)
C4—C5—C9—C1150.4 (3)C12—C13—C14—C15167.0 (2)
C6—C5—C9—C11169.1 (2)C17—C13—C14—C1545.9 (3)
C10—C5—C9—C8153.5 (2)C18—C13—C14—C1570.2 (3)
C4—C5—C9—C882.4 (3)C8—C14—C15—C16160.7 (2)
C6—C5—C9—C836.3 (2)C13—C14—C15—C1631.3 (3)
C14—C8—C9—C1126.5 (3)C14—C15—C16—C173.9 (3)
C7—C8—C9—C11149.4 (2)C15—C16—C17—O21151.9 (3)
C14—C8—C9—C5105.5 (2)C15—C16—C17—C1324.7 (3)
C7—C8—C9—C517.4 (3)C12—C13—C17—O2174.7 (3)
C2—C1—C10—O19149.7 (3)C14—C13—C17—O21169.7 (2)
C2—C1—C10—C532.7 (4)C18—C13—C17—O2151.2 (3)
C4—C5—C10—O19158.1 (3)C12—C13—C17—C16158.7 (2)
C6—C5—C10—O1979.6 (3)C14—C13—C17—C1643.2 (2)
C9—C5—C10—O1931.9 (4)C18—C13—C17—C1675.3 (3)
C4—C5—C10—C119.5 (3)
 

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