



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015009123/cv5486sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015009123/cv5486Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015009123/cv5486Isup3.cml |
CCDC reference: 1400503
Key indicators
- Single-crystal X-ray study
- T = 173 K
- R factor = 0.060
- wR factor = 0.189
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
The title compound, 3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulfonate (I) (Fig. 1), is an intermediate of the synthesis of abiraterone acetate which is a pro-drug for 17-(pyridin-3- yl)androsta-5,16-dien-3P-ol, or abiraterone, a potent inhibitor of human cytochrome P45017α (steroidal 17α-hydroxylase-C17,20-lyase) (Attard et al. 2009). 3β-Acetoxyandrosta-5,16-dien-17-yl trifluoromethane- sulfonate was first synthesized and charaterized by Potter et al. (1995), but structural data were not obtained. In this work, we obtained a single-crystal of (I) and present here its crystal structure.
The title molecule contains a fused four-ring steroidal system. The two saturated six-membered rings A and C adopt chair conformations,while ring B with one double bond adopts a half-chair conformation, and ring D with one double bond adopts an envelope conformation. The absolute structure of (I), which is crystallized in a chiral space group P212121, was reliably determined based on the value of Flack parameter [0.02 (3)]. In the crystal, weak intermolecular C—H···O interactions link the molecules into layers parallel to ab plane.
3β-Acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulfonate was synthesized from dehydro-epiandrosterone acetate via trifluoromethanesulfonic anhydride with an overall yield of 58% according to a literature method (Potter, 1995). Colourless crystals were obtained by evaporation from a hexane solution.
Crystal data, data collection and structure refinement details are summarized in Table 1. Crystal data, data collection and structure refinement details are summarized in Table 1. All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, for aromatic, 0.98 Å for C—H and 0.97 Å for CH2 with Uiso = 1.2Ueq (C). d(C—H) = 0.96 Å with Uiso = 1.5Ueq (C) for CH3 H atoms. The absolute structure could be determined reliably.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).
![]() | Fig. 1. The molecular structure of (I) showing the atomic labeling and 50% probability displacement ellipsoids. |
C22H29F3O5S | F(000) = 976 |
Mr = 462.51 | Dx = 1.379 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0734 (10) Å | µ = 0.20 mm−1 |
b = 9.9640 (12) Å | T = 173 K |
c = 27.6900 (15) Å | Block, colourless |
V = 2227.5 (4) Å3 | 0.10 × 0.10 × 0.08 mm |
Z = 4 |
Bruker SMART APEX 2000 diffractometer | 5098 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3185 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ϕ and ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.980, Tmax = 0.984 | k = −12→12 |
22017 measured reflections | l = −34→35 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.0997P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.189 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 0.27 e Å−3 |
5098 reflections | Δρmin = −0.66 e Å−3 |
280 parameters | Absolute structure: Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.02 (3) |
C22H29F3O5S | V = 2227.5 (4) Å3 |
Mr = 462.51 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.0734 (10) Å | µ = 0.20 mm−1 |
b = 9.9640 (12) Å | T = 173 K |
c = 27.6900 (15) Å | 0.10 × 0.10 × 0.08 mm |
Bruker SMART APEX 2000 diffractometer | 5098 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3185 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.984 | Rint = 0.058 |
22017 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.189 | Δρmax = 0.27 e Å−3 |
S = 1.11 | Δρmin = −0.66 e Å−3 |
5098 reflections | Absolute structure: Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
280 parameters | Absolute structure parameter: 0.02 (3) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.10597 (18) | 0.04595 (17) | 0.06476 (4) | 0.0579 (4) | |
C1 | 0.4181 (6) | 0.0552 (5) | 0.35593 (14) | 0.0427 (11) | |
H1A | 0.3017 | 0.0423 | 0.3632 | 0.051* | |
H1B | 0.4598 | −0.0284 | 0.3427 | 0.051* | |
C2 | 0.5109 (7) | 0.0846 (6) | 0.40342 (16) | 0.0494 (13) | |
H2A | 0.4642 | 0.1634 | 0.4189 | 0.059* | |
H2B | 0.4999 | 0.0092 | 0.4253 | 0.059* | |
C3 | 0.6921 (6) | 0.1085 (5) | 0.39178 (16) | 0.0449 (12) | |
H3 | 0.7385 | 0.0276 | 0.3769 | 0.054* | |
C4 | 0.7123 (7) | 0.2252 (5) | 0.35765 (16) | 0.0468 (12) | |
H4A | 0.8288 | 0.2381 | 0.3505 | 0.056* | |
H4B | 0.6710 | 0.3064 | 0.3728 | 0.056* | |
C5 | 0.6179 (6) | 0.1994 (5) | 0.31113 (16) | 0.0391 (10) | |
C6 | 0.6943 (6) | 0.2032 (5) | 0.26896 (16) | 0.0425 (11) | |
H6 | 0.8077 | 0.2195 | 0.2694 | 0.051* | |
C7 | 0.6156 (6) | 0.1838 (5) | 0.22092 (16) | 0.0408 (10) | |
H7A | 0.6479 | 0.0972 | 0.2080 | 0.049* | |
H7B | 0.6546 | 0.2526 | 0.1989 | 0.049* | |
C8 | 0.4257 (5) | 0.1907 (5) | 0.22442 (15) | 0.0372 (10) | |
H8 | 0.3908 | 0.2846 | 0.2276 | 0.045* | |
C9 | 0.3643 (5) | 0.1100 (4) | 0.26848 (16) | 0.0366 (10) | |
H9 | 0.4104 | 0.0195 | 0.2649 | 0.044* | |
C10 | 0.4335 (6) | 0.1654 (4) | 0.31691 (16) | 0.0374 (10) | |
C11 | 0.1732 (6) | 0.0929 (5) | 0.26877 (16) | 0.0420 (11) | |
H11A | 0.1441 | 0.0284 | 0.2936 | 0.050* | |
H11B | 0.1235 | 0.1781 | 0.2776 | 0.050* | |
C12 | 0.0973 (6) | 0.0464 (5) | 0.22079 (15) | 0.0396 (10) | |
H12A | 0.1297 | −0.0456 | 0.2143 | 0.048* | |
H12B | −0.0226 | 0.0498 | 0.2228 | 0.048* | |
C13 | 0.1568 (5) | 0.1370 (5) | 0.17978 (15) | 0.0366 (10) | |
C14 | 0.3473 (5) | 0.1296 (5) | 0.17969 (16) | 0.0376 (10) | |
H14 | 0.3725 | 0.0336 | 0.1819 | 0.045* | |
C15 | 0.3994 (7) | 0.1698 (6) | 0.12816 (16) | 0.0500 (12) | |
H15A | 0.4076 | 0.2665 | 0.1247 | 0.060* | |
H15B | 0.5038 | 0.1288 | 0.1190 | 0.060* | |
C16 | 0.2568 (7) | 0.1135 (6) | 0.09945 (17) | 0.0519 (13) | |
H16 | 0.2587 | 0.0952 | 0.0665 | 0.062* | |
C17 | 0.1287 (6) | 0.0943 (5) | 0.12839 (16) | 0.0413 (11) | |
C18 | −0.1421 (9) | 0.2240 (8) | 0.0518 (3) | 0.081 (2) | |
C19 | 0.9433 (6) | 0.1150 (6) | 0.4372 (2) | 0.0546 (13) | |
C20 | 1.0190 (8) | 0.1479 (7) | 0.4847 (2) | 0.0683 (17) | |
H20A | 0.9341 | 0.1767 | 0.5067 | 0.102* | |
H20B | 1.0730 | 0.0697 | 0.4975 | 0.102* | |
H20C | 1.0987 | 0.2185 | 0.4807 | 0.102* | |
C21 | 0.3391 (7) | 0.2934 (5) | 0.33312 (19) | 0.0531 (13) | |
H21A | 0.2236 | 0.2729 | 0.3368 | 0.080* | |
H21B | 0.3830 | 0.3241 | 0.3634 | 0.080* | |
H21C | 0.3523 | 0.3623 | 0.3092 | 0.080* | |
C22 | 0.0868 (7) | 0.2809 (5) | 0.18514 (18) | 0.0481 (12) | |
H22A | 0.1028 | 0.3114 | 0.2177 | 0.072* | |
H22B | 0.1435 | 0.3400 | 0.1633 | 0.072* | |
H22C | −0.0294 | 0.2806 | 0.1777 | 0.072* | |
O1 | 0.0134 (6) | 0.0001 (5) | 0.03104 (14) | 0.0813 (15) | |
O2 | −0.2654 (5) | −0.0135 (5) | 0.06899 (13) | 0.0779 (14) | |
O3 | −0.0360 (4) | 0.0520 (4) | 0.11675 (10) | 0.0473 (8) | |
O4 | 1.0173 (5) | 0.0759 (5) | 0.40211 (14) | 0.0753 (13) | |
O5 | 0.7779 (4) | 0.1346 (4) | 0.43747 (11) | 0.0484 (8) | |
F1 | −0.2250 (9) | 0.2339 (7) | 0.0126 (2) | 0.181 (3) | |
F2 | −0.2274 (6) | 0.2797 (5) | 0.0871 (2) | 0.128 (2) | |
F3 | −0.0052 (5) | 0.2913 (4) | 0.04760 (17) | 0.0985 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0568 (8) | 0.0737 (10) | 0.0432 (6) | −0.0149 (8) | −0.0045 (6) | 0.0026 (7) |
C1 | 0.046 (3) | 0.043 (3) | 0.040 (2) | −0.008 (2) | 0.002 (2) | 0.003 (2) |
C2 | 0.056 (3) | 0.058 (3) | 0.034 (2) | −0.011 (3) | 0.006 (2) | −0.002 (2) |
C3 | 0.045 (3) | 0.049 (3) | 0.041 (2) | −0.007 (2) | 0.001 (2) | −0.005 (2) |
C4 | 0.052 (3) | 0.041 (3) | 0.047 (3) | −0.006 (2) | 0.002 (2) | −0.004 (2) |
C5 | 0.037 (2) | 0.033 (2) | 0.047 (2) | −0.003 (2) | 0.004 (2) | −0.0006 (19) |
C6 | 0.035 (2) | 0.044 (3) | 0.049 (3) | −0.005 (2) | 0.004 (2) | −0.001 (2) |
C7 | 0.029 (2) | 0.042 (3) | 0.051 (3) | −0.002 (2) | 0.006 (2) | 0.003 (2) |
C8 | 0.033 (2) | 0.036 (2) | 0.043 (2) | −0.0019 (19) | 0.0078 (19) | −0.001 (2) |
C9 | 0.034 (2) | 0.031 (2) | 0.044 (2) | −0.0018 (19) | 0.0051 (19) | −0.0007 (19) |
C10 | 0.035 (2) | 0.034 (2) | 0.043 (2) | −0.0026 (19) | 0.0037 (18) | −0.0027 (19) |
C11 | 0.036 (2) | 0.048 (3) | 0.042 (2) | −0.004 (2) | 0.005 (2) | 0.000 (2) |
C12 | 0.034 (2) | 0.038 (2) | 0.047 (2) | −0.003 (2) | 0.001 (2) | 0.004 (2) |
C13 | 0.039 (3) | 0.036 (2) | 0.035 (2) | 0.000 (2) | 0.0048 (18) | 0.0005 (19) |
C14 | 0.032 (2) | 0.037 (2) | 0.043 (2) | 0.0008 (19) | 0.0073 (18) | −0.002 (2) |
C15 | 0.043 (3) | 0.061 (3) | 0.046 (3) | −0.004 (3) | 0.012 (2) | 0.000 (2) |
C16 | 0.056 (3) | 0.059 (3) | 0.041 (3) | −0.005 (3) | 0.008 (2) | −0.004 (2) |
C17 | 0.043 (3) | 0.040 (3) | 0.041 (2) | 0.000 (2) | −0.002 (2) | −0.0018 (19) |
C18 | 0.059 (4) | 0.092 (5) | 0.093 (5) | 0.002 (4) | 0.004 (4) | 0.046 (4) |
C19 | 0.047 (3) | 0.060 (3) | 0.057 (3) | −0.009 (3) | 0.000 (3) | 0.003 (3) |
C20 | 0.066 (4) | 0.083 (4) | 0.057 (3) | −0.017 (4) | −0.011 (3) | 0.006 (3) |
C21 | 0.053 (3) | 0.047 (3) | 0.059 (3) | 0.004 (3) | 0.006 (2) | −0.014 (2) |
C22 | 0.052 (3) | 0.038 (3) | 0.054 (3) | 0.003 (2) | 0.008 (2) | 0.003 (2) |
O1 | 0.077 (3) | 0.111 (4) | 0.057 (2) | −0.019 (3) | 0.008 (2) | −0.031 (2) |
O2 | 0.064 (3) | 0.112 (4) | 0.058 (2) | −0.044 (3) | −0.007 (2) | 0.005 (2) |
O3 | 0.0452 (19) | 0.063 (2) | 0.0339 (15) | −0.0105 (18) | −0.0021 (13) | 0.0028 (16) |
O4 | 0.054 (2) | 0.110 (4) | 0.062 (2) | 0.008 (3) | 0.004 (2) | −0.009 (2) |
O5 | 0.046 (2) | 0.060 (2) | 0.0387 (17) | −0.0038 (18) | −0.0006 (15) | −0.0044 (16) |
F1 | 0.166 (6) | 0.213 (7) | 0.165 (5) | −0.031 (5) | −0.097 (5) | 0.113 (5) |
F2 | 0.093 (3) | 0.092 (3) | 0.200 (5) | 0.032 (3) | 0.061 (4) | 0.049 (4) |
F3 | 0.076 (3) | 0.082 (3) | 0.137 (4) | 0.000 (2) | 0.027 (3) | 0.048 (3) |
S1—O1 | 1.418 (4) | C11—H11A | 0.9700 |
S1—O2 | 1.422 (4) | C11—H11B | 0.9700 |
S1—O3 | 1.547 (3) | C12—C13 | 1.528 (6) |
S1—C18 | 1.834 (7) | C12—H12A | 0.9700 |
C1—C2 | 1.542 (6) | C12—H12B | 0.9700 |
C1—C10 | 1.546 (6) | C13—C17 | 1.502 (6) |
C1—H1A | 0.9700 | C13—C14 | 1.539 (6) |
C1—H1B | 0.9700 | C13—C22 | 1.549 (7) |
C2—C3 | 1.517 (7) | C14—C15 | 1.541 (6) |
C2—H2A | 0.9700 | C14—H14 | 0.9800 |
C2—H2B | 0.9700 | C15—C16 | 1.507 (7) |
C3—O5 | 1.465 (5) | C15—H15A | 0.9700 |
C3—C4 | 1.507 (7) | C15—H15B | 0.9700 |
C3—H3 | 0.9800 | C16—C17 | 1.323 (7) |
C4—C5 | 1.518 (6) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C17—O3 | 1.431 (6) |
C4—H4B | 0.9700 | C18—F1 | 1.278 (8) |
C5—C6 | 1.321 (6) | C18—F3 | 1.298 (8) |
C5—C10 | 1.535 (6) | C18—F2 | 1.319 (9) |
C6—C7 | 1.487 (6) | C19—O4 | 1.206 (6) |
C6—H6 | 0.9300 | C19—O5 | 1.350 (6) |
C7—C8 | 1.538 (6) | C19—C20 | 1.487 (7) |
C7—H7A | 0.9700 | C20—H20A | 0.9600 |
C7—H7B | 0.9700 | C20—H20B | 0.9600 |
C8—C14 | 1.519 (6) | C20—H20C | 0.9600 |
C8—C9 | 1.543 (6) | C21—H21A | 0.9600 |
C8—H8 | 0.9800 | C21—H21B | 0.9600 |
C9—C11 | 1.552 (6) | C21—H21C | 0.9600 |
C9—C10 | 1.554 (6) | C22—H22A | 0.9600 |
C9—H9 | 0.9800 | C22—H22B | 0.9600 |
C10—C21 | 1.552 (7) | C22—H22C | 0.9600 |
C11—C12 | 1.535 (6) | ||
O1—S1—O2 | 122.4 (3) | C12—C11—H11B | 108.5 |
O1—S1—O3 | 112.1 (2) | C9—C11—H11B | 108.5 |
O2—S1—O3 | 105.7 (2) | H11A—C11—H11B | 107.5 |
O1—S1—C18 | 106.9 (3) | C13—C12—C11 | 109.8 (4) |
O2—S1—C18 | 106.0 (3) | C13—C12—H12A | 109.7 |
O3—S1—C18 | 101.7 (3) | C11—C12—H12A | 109.7 |
C2—C1—C10 | 114.9 (4) | C13—C12—H12B | 109.7 |
C2—C1—H1A | 108.5 | C11—C12—H12B | 109.7 |
C10—C1—H1A | 108.5 | H12A—C12—H12B | 108.2 |
C2—C1—H1B | 108.5 | C17—C13—C12 | 119.3 (4) |
C10—C1—H1B | 108.5 | C17—C13—C14 | 97.8 (4) |
H1A—C1—H1B | 107.5 | C12—C13—C14 | 106.7 (4) |
C3—C2—C1 | 108.5 (4) | C17—C13—C22 | 107.3 (4) |
C3—C2—H2A | 110.0 | C12—C13—C22 | 111.2 (4) |
C1—C2—H2A | 110.0 | C14—C13—C22 | 114.2 (4) |
C3—C2—H2B | 110.0 | C8—C14—C13 | 113.3 (4) |
C1—C2—H2B | 110.0 | C8—C14—C15 | 122.5 (4) |
H2A—C2—H2B | 108.4 | C13—C14—C15 | 105.2 (4) |
O5—C3—C4 | 110.7 (4) | C8—C14—H14 | 104.7 |
O5—C3—C2 | 107.5 (4) | C13—C14—H14 | 104.7 |
C4—C3—C2 | 111.0 (4) | C15—C14—H14 | 104.7 |
O5—C3—H3 | 109.2 | C16—C15—C14 | 100.5 (4) |
C4—C3—H3 | 109.2 | C16—C15—H15A | 111.7 |
C2—C3—H3 | 109.2 | C14—C15—H15A | 111.7 |
C3—C4—C5 | 110.3 (4) | C16—C15—H15B | 111.7 |
C3—C4—H4A | 109.6 | C14—C15—H15B | 111.7 |
C5—C4—H4A | 109.6 | H15A—C15—H15B | 109.4 |
C3—C4—H4B | 109.6 | C17—C16—C15 | 109.4 (4) |
C5—C4—H4B | 109.6 | C17—C16—H16 | 125.3 |
H4A—C4—H4B | 108.1 | C15—C16—H16 | 125.3 |
C6—C5—C4 | 120.7 (4) | C16—C17—O3 | 129.2 (4) |
C6—C5—C10 | 123.4 (4) | C16—C17—C13 | 114.5 (4) |
C4—C5—C10 | 115.8 (4) | O3—C17—C13 | 115.9 (4) |
C5—C6—C7 | 126.0 (4) | F1—C18—F3 | 109.3 (6) |
C5—C6—H6 | 117.0 | F1—C18—F2 | 108.9 (7) |
C7—C6—H6 | 117.0 | F3—C18—F2 | 107.0 (7) |
C6—C7—C8 | 111.3 (4) | F1—C18—S1 | 108.9 (7) |
C6—C7—H7A | 109.4 | F3—C18—S1 | 112.4 (5) |
C8—C7—H7A | 109.4 | F2—C18—S1 | 110.1 (5) |
C6—C7—H7B | 109.4 | O4—C19—O5 | 122.7 (5) |
C8—C7—H7B | 109.4 | O4—C19—C20 | 125.5 (5) |
H7A—C7—H7B | 108.0 | O5—C19—C20 | 111.7 (5) |
C14—C8—C7 | 110.3 (4) | C19—C20—H20A | 109.5 |
C14—C8—C9 | 107.6 (4) | C19—C20—H20B | 109.5 |
C7—C8—C9 | 110.3 (4) | H20A—C20—H20B | 109.5 |
C14—C8—H8 | 109.6 | C19—C20—H20C | 109.5 |
C7—C8—H8 | 109.6 | H20A—C20—H20C | 109.5 |
C9—C8—H8 | 109.6 | H20B—C20—H20C | 109.5 |
C8—C9—C11 | 112.4 (4) | C10—C21—H21A | 109.5 |
C8—C9—C10 | 112.4 (3) | C10—C21—H21B | 109.5 |
C11—C9—C10 | 113.1 (4) | H21A—C21—H21B | 109.5 |
C8—C9—H9 | 106.1 | C10—C21—H21C | 109.5 |
C11—C9—H9 | 106.1 | H21A—C21—H21C | 109.5 |
C10—C9—H9 | 106.1 | H21B—C21—H21C | 109.5 |
C5—C10—C1 | 107.9 (4) | C13—C22—H22A | 109.5 |
C5—C10—C21 | 109.0 (4) | C13—C22—H22B | 109.5 |
C1—C10—C21 | 110.0 (4) | H22A—C22—H22B | 109.5 |
C5—C10—C9 | 109.7 (4) | C13—C22—H22C | 109.5 |
C1—C10—C9 | 108.8 (4) | H22A—C22—H22C | 109.5 |
C21—C10—C9 | 111.4 (4) | H22B—C22—H22C | 109.5 |
C12—C11—C9 | 115.2 (4) | C17—O3—S1 | 124.1 (3) |
C12—C11—H11A | 108.5 | C19—O5—C3 | 116.0 (4) |
C9—C11—H11A | 108.5 | ||
C10—C1—C2—C3 | −56.8 (6) | C9—C8—C14—C13 | 61.6 (5) |
C1—C2—C3—O5 | −179.3 (4) | C7—C8—C14—C15 | −50.3 (6) |
C1—C2—C3—C4 | 59.5 (6) | C9—C8—C14—C15 | −170.6 (4) |
O5—C3—C4—C5 | −178.0 (4) | C17—C13—C14—C8 | 169.8 (4) |
C2—C3—C4—C5 | −58.7 (5) | C12—C13—C14—C8 | −66.4 (5) |
C3—C4—C5—C6 | −123.9 (5) | C22—C13—C14—C8 | 56.8 (5) |
C3—C4—C5—C10 | 54.4 (6) | C17—C13—C14—C15 | 33.5 (5) |
C4—C5—C6—C7 | −178.1 (5) | C12—C13—C14—C15 | 157.3 (4) |
C10—C5—C6—C7 | 3.8 (8) | C22—C13—C14—C15 | −79.6 (5) |
C5—C6—C7—C8 | 13.3 (7) | C8—C14—C15—C16 | −164.6 (4) |
C6—C7—C8—C14 | −162.7 (4) | C13—C14—C15—C16 | −33.4 (5) |
C6—C7—C8—C9 | −44.0 (5) | C14—C15—C16—C17 | 19.7 (6) |
C14—C8—C9—C11 | −49.8 (5) | C15—C16—C17—O3 | 175.0 (5) |
C7—C8—C9—C11 | −170.1 (4) | C15—C16—C17—C13 | 2.1 (6) |
C14—C8—C9—C10 | −178.7 (4) | C12—C13—C17—C16 | −136.8 (5) |
C7—C8—C9—C10 | 61.0 (5) | C14—C13—C17—C16 | −22.7 (5) |
C6—C5—C10—C1 | 129.6 (5) | C22—C13—C17—C16 | 95.7 (5) |
C4—C5—C10—C1 | −48.6 (5) | C12—C13—C17—O3 | 49.2 (6) |
C6—C5—C10—C21 | −111.0 (5) | C14—C13—C17—O3 | 163.4 (4) |
C4—C5—C10—C21 | 70.8 (5) | C22—C13—C17—O3 | −78.2 (5) |
C6—C5—C10—C9 | 11.2 (6) | O1—S1—C18—F1 | 72.5 (6) |
C4—C5—C10—C9 | −167.0 (4) | O2—S1—C18—F1 | −59.5 (6) |
C2—C1—C10—C5 | 50.1 (5) | O3—S1—C18—F1 | −169.8 (5) |
C2—C1—C10—C21 | −68.7 (5) | O1—S1—C18—F3 | −48.9 (6) |
C2—C1—C10—C9 | 169.0 (4) | O2—S1—C18—F3 | 179.2 (5) |
C8—C9—C10—C5 | −42.9 (5) | O3—S1—C18—F3 | 68.9 (6) |
C11—C9—C10—C5 | −171.4 (4) | O1—S1—C18—F2 | −168.1 (5) |
C8—C9—C10—C1 | −160.7 (4) | O2—S1—C18—F2 | 59.9 (6) |
C11—C9—C10—C1 | 70.7 (5) | O3—S1—C18—F2 | −50.4 (6) |
C8—C9—C10—C21 | 77.8 (5) | C16—C17—O3—S1 | −12.4 (7) |
C11—C9—C10—C21 | −50.7 (5) | C13—C17—O3—S1 | 160.5 (3) |
C8—C9—C11—C12 | 48.0 (6) | O1—S1—O3—C17 | 38.7 (5) |
C10—C9—C11—C12 | 176.5 (4) | O2—S1—O3—C17 | 174.3 (4) |
C9—C11—C12—C13 | −51.9 (6) | C18—S1—O3—C17 | −75.2 (4) |
C11—C12—C13—C17 | 167.1 (4) | O4—C19—O5—C3 | −1.4 (8) |
C11—C12—C13—C14 | 57.8 (5) | C20—C19—O5—C3 | 178.3 (4) |
C11—C12—C13—C22 | −67.2 (5) | C4—C3—O5—C19 | −79.5 (5) |
C7—C8—C14—C13 | −178.1 (4) | C2—C3—O5—C19 | 159.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O4i | 0.97 | 2.56 | 3.485 (6) | 160 |
C21—H21B···O2ii | 0.97 | 2.65 | 3.377 (7) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O4i | 0.97 | 2.56 | 3.485 (6) | 160 |
C21—H21B···O2ii | 0.97 | 2.65 | 3.377 (7) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2. |