Prednisolone acetate {systematic name: 2-[(8S,9S,10R,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate}, is an ophthalmic drug that belongs to the class of corticosteroids. Its crystal structure was refined using the classical independent atom model (IAM) and a transferred multipolar atom model using the ELMAM2 database. The results of both refinements have been compared. The ELMAM2 refinement was found to be superior in terms of the refinement statistics. It has been shown that certain electron-density-derived properties can be calculated on the basis of the transferred parameters for crystals which diffract to ordinary resolution. The procedure proves helpful in understanding the mode of action of the drug molecule.
Supporting information
CCDC references: 1547360; 1547359; 1547358
For all structures, data collection: Bruker D8 Venture Photon 100 CMOS Detector (Bruker, 2014). Cell refinement: APEX2 (Bruker, 2014) for ELMAM2; APEXII (Bruker, 2014) for IAM_MoPro; APEX II (Bruker, 2014) for IAM_shelx. For all structures, data reduction: SAINT (Bruker, 2014). Program(s) used to solve structure: SIR92 (Altomare et al., 1993) for ELMAM2, IAM_shelx. Program(s) used to refine structure: MoPro (Jelsch et al., 2005) for ELMAM2, IAM_MoPro; SHELXL2015 (Sheldrick, 2015) for IAM_shelx. For all structures, molecular graphics: Mercury (Macrae et al., 2006) and MoProViewer (Guillot, 2011); software used to prepare material for publication: pubCIF (Westrip, 2010).
2-[(8
S,9
S,10
R,13
S,14
S,17
R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3
H-cyclopenta[
a]phenanthren-17-yl]-2-oxoethyl
acetate (ELMAM2)
top
Crystal data top
C23H30O6 | F(000) = 432 |
Mr = 402.46 | Dx = 1.303 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 1200 reflections |
a = 8.4816 (1) Å | θ = 5.1–72.2° |
b = 13.865 (3) Å | µ = 0.76 mm−1 |
c = 8.9437 (1) Å | T = 100 K |
β = 102.709 (1)° | Block, colorless |
V = 1026.0 (2) Å3 | 0.43 × 0.34 × 0.21 mm |
Z = 2 | |
Data collection top
Bruker Kappa APEXII CMOS detector diffractometer | 4018 independent reflections |
Radiation source: Microfocus | 3976 reflections with > 2.0σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scan | θmax = 72.2°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = 0→10 |
Tmin = 0.735, Tmax = 0.856 | k = −17→17 |
16242 measured reflections | l = −11→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.018 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.048 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.02P] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
4018 reflections | Δρmax = 0.11 e Å−3 |
262 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (5) |
Special details top
Refinement. Refinement of F2 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) 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 | x | y | z | Uiso*/Ueq | |
O5 | 0.70274 (8) | 0.6266 (2) | 0.22895 (7) | 0.02560 (7) | |
O1 | 0.18968 (7) | 0.3601 (2) | 1.26199 (6) | 0.01831 (7) | |
O2 | 0.12075 (8) | 0.4751 (2) | 0.49923 (7) | 0.02034 (7) | |
O3 | 0.62449 (7) | 0.7004 (2) | 0.65025 (6) | 0.01935 (7) | |
O4 | 0.48420 (9) | 0.7664 (2) | 0.26468 (7) | 0.02775 (8) | |
O6 | 0.48211 (8) | 0.5327 (2) | 0.20364 (8) | 0.02625 (7) | |
C3 | 0.15950 (10) | 0.3957 (2) | 1.13056 (9) | 0.01413 (8) | |
C2 | 0.19306 (11) | 0.3429 (2) | 0.99978 (10) | 0.01738 (9) | |
H2 | 0.25244 | 0.27333 | 1.01692 | 0.03693 | |
C1 | 0.15160 (11) | 0.3802 (2) | 0.85832 (10) | 0.01736 (9) | |
H1 | 0.17009 | 0.33641 | 0.76335 | 0.03530 | |
C10 | 0.08137 (10) | 0.4792 (2) | 0.82179 (9) | 0.01449 (9) | |
C4 | 0.08747 (10) | 0.4907 (2) | 1.10259 (9) | 0.01434 (8) | |
H4 | 0.05908 | 0.52977 | 1.19818 | 0.03176 | |
C5 | 0.05640 (9) | 0.5314 (2) | 0.96281 (9) | 0.01396 (8) | |
C6 | 0.00186 (11) | 0.6342 (2) | 0.94013 (9) | 0.01775 (9) | |
H6A | −0.01127 | 0.66577 | 1.04862 | 0.03472 | |
H6B | −0.11510 | 0.63859 | 0.85956 | 0.03544 | |
C7 | 0.12760 (11) | 0.6920 (2) | 0.87742 (9) | 0.01830 (9) | |
H7A | 0.24166 | 0.69327 | 0.96262 | 0.03302 | |
H7B | 0.08610 | 0.76614 | 0.85396 | 0.03629 | |
C8 | 0.15900 (10) | 0.6479 (2) | 0.72921 (9) | 0.01447 (9) | |
H8 | 0.04937 | 0.65426 | 0.63766 | 0.03016 | |
C9 | 0.20722 (10) | 0.5404 (2) | 0.75477 (8) | 0.01321 (8) | |
H9 | 0.31715 | 0.54081 | 0.84668 | 0.02710 | |
C11 | 0.26000 (10) | 0.4929 (2) | 0.61779 (9) | 0.01494 (9) | |
H11 | 0.31543 | 0.42317 | 0.65711 | 0.03358 | |
C12 | 0.38872 (10) | 0.5527 (2) | 0.56167 (9) | 0.01551 (8) | |
H12A | 0.50331 | 0.54589 | 0.64523 | 0.03282 | |
H12B | 0.40596 | 0.52171 | 0.45416 | 0.03400 | |
C13 | 0.34482 (10) | 0.6595 (2) | 0.53767 (9) | 0.01444 (8) | |
C14 | 0.30050 (10) | 0.6997 (2) | 0.68381 (9) | 0.01511 (9) | |
H14A | 0.40566 | 0.68690 | 0.77816 | 0.02935 | |
C15 | 0.29384 (12) | 0.8094 (2) | 0.65822 (10) | 0.02021 (10) | |
H15A | 0.32343 | 0.84814 | 0.76714 | 0.03954 | |
H15B | 0.17404 | 0.83154 | 0.59516 | 0.03932 | |
C16 | 0.42260 (11) | 0.8282 (2) | 0.56167 (10) | 0.01997 (9) | |
H16A | 0.36699 | 0.86372 | 0.45396 | 0.04149 | |
H16B | 0.51973 | 0.87294 | 0.62700 | 0.04228 | |
C17 | 0.48963 (10) | 0.7281 (2) | 0.53083 (9) | 0.01705 (9) | |
C20 | 0.54379 (11) | 0.7207 (2) | 0.37846 (10) | 0.01988 (9) | |
C21 | 0.68346 (11) | 0.6506 (2) | 0.37939 (10) | 0.02396 (10) | |
H21A | 0.79593 | 0.68280 | 0.44269 | 0.04096 | |
H21B | 0.66052 | 0.58389 | 0.43596 | 0.03750 | |
C22 | 0.59418 (11) | 0.5616 (2) | 0.15387 (10) | 0.02108 (9) | |
C23 | 0.63519 (11) | 0.5306 (2) | 0.00648 (10) | 0.02805 (10) | |
H23C | 0.55534 | 0.47313 | −0.04330 | 0.05238 | |
H23B | 0.75949 | 0.50767 | 0.02937 | 0.05341 | |
H23A | 0.62022 | 0.59118 | −0.07080 | 0.05162 | |
C19 | −0.08754 (11) | 0.4672 (2) | 0.71237 (10) | 0.02251 (9) | |
H19B | −0.07736 | 0.42416 | 0.61470 | 0.04243 | |
H19C | −0.13450 | 0.53720 | 0.67363 | 0.04123 | |
H19A | −0.16963 | 0.43416 | 0.77342 | 0.04272 | |
C18 | 0.20904 (11) | 0.6751 (2) | 0.39418 (9) | 0.01826 (9) | |
H18B | 0.24783 | 0.64560 | 0.29679 | 0.04105 | |
H18C | 0.18779 | 0.75138 | 0.37878 | 0.04239 | |
H18A | 0.10196 | 0.63877 | 0.41082 | 0.04039 | |
HO2 | 0.15410 | 0.43897 | 0.42280 | 0.03227 | |
HO3 | 0.69621 | 0.75701 | 0.68342 | 0.03495 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0176 (3) | 0.0355 (3) | 0.0249 (3) | −0.0051 (3) | 0.0073 (2) | 0.0017 (3) |
O1 | 0.0219 (3) | 0.0171 (3) | 0.0149 (3) | 0.0033 (2) | 0.0019 (2) | 0.0025 (2) |
O2 | 0.0243 (3) | 0.0213 (3) | 0.0163 (3) | −0.0079 (2) | 0.0064 (2) | −0.0059 (2) |
O3 | 0.0185 (3) | 0.0155 (3) | 0.0207 (3) | −0.0018 (2) | −0.0029 (2) | 0.0020 (2) |
O4 | 0.0329 (4) | 0.0257 (3) | 0.0242 (3) | −0.0007 (3) | 0.0055 (3) | 0.0111 (3) |
O6 | 0.0216 (3) | 0.0301 (3) | 0.0293 (3) | −0.0040 (3) | 0.0107 (3) | 0.0015 (3) |
C3 | 0.0147 (4) | 0.0128 (3) | 0.0143 (4) | 0.0006 (3) | 0.0020 (3) | 0.0008 (3) |
C2 | 0.0238 (4) | 0.0108 (3) | 0.0198 (4) | 0.0015 (3) | 0.0097 (3) | 0.0002 (3) |
H2 | 0.05198 | 0.02029 | 0.04067 | 0.00600 | 0.01486 | 0.00177 |
C1 | 0.0272 (4) | 0.0093 (3) | 0.0178 (4) | −0.0019 (3) | 0.0098 (3) | −0.0020 (3) |
H1 | 0.05127 | 0.02568 | 0.03145 | −0.00183 | 0.01453 | −0.00820 |
C10 | 0.0190 (4) | 0.0121 (3) | 0.0126 (3) | −0.0012 (3) | 0.0039 (3) | −0.0013 (3) |
C4 | 0.0163 (4) | 0.0132 (4) | 0.0130 (3) | 0.0029 (3) | 0.0023 (3) | −0.0011 (3) |
H4 | 0.03702 | 0.03372 | 0.02441 | 0.00708 | 0.00647 | −0.00476 |
C5 | 0.0153 (4) | 0.0124 (4) | 0.0140 (3) | 0.0015 (3) | 0.0029 (3) | −0.0016 (3) |
C6 | 0.0214 (4) | 0.0139 (4) | 0.0182 (4) | 0.0058 (3) | 0.0049 (3) | 0.0008 (3) |
H6A | 0.04309 | 0.03523 | 0.02583 | 0.00640 | 0.00755 | −0.00554 |
H6B | 0.02766 | 0.04292 | 0.03100 | 0.00496 | −0.00383 | 0.00265 |
C7 | 0.0233 (4) | 0.0120 (3) | 0.0198 (4) | 0.0034 (3) | 0.0050 (3) | −0.0009 (3) |
H7A | 0.02980 | 0.03530 | 0.03005 | 0.00236 | −0.00186 | −0.00186 |
H7B | 0.04588 | 0.02314 | 0.03965 | 0.01258 | 0.00901 | 0.00325 |
C8 | 0.0170 (4) | 0.0102 (3) | 0.0154 (4) | 0.0018 (3) | 0.0017 (3) | 0.0007 (3) |
H8 | 0.02696 | 0.03339 | 0.02688 | 0.00318 | −0.00114 | 0.00091 |
C9 | 0.0169 (4) | 0.0095 (3) | 0.0130 (3) | −0.0004 (3) | 0.0028 (3) | −0.0001 (3) |
H9 | 0.02539 | 0.02517 | 0.02792 | 0.00011 | −0.00027 | −0.00141 |
C11 | 0.0205 (4) | 0.0095 (3) | 0.0159 (3) | −0.0013 (3) | 0.0062 (3) | −0.0006 (3) |
H11 | 0.03951 | 0.02142 | 0.04180 | 0.00315 | 0.01323 | 0.00261 |
C12 | 0.0187 (4) | 0.0112 (3) | 0.0173 (3) | −0.0012 (3) | 0.0055 (3) | 0.0009 (3) |
H12A | 0.02819 | 0.03069 | 0.03622 | −0.00102 | −0.00017 | 0.00353 |
H12B | 0.04324 | 0.03091 | 0.03047 | −0.00279 | 0.01374 | −0.00487 |
C13 | 0.0163 (4) | 0.0108 (3) | 0.0151 (4) | −0.0020 (3) | 0.0008 (3) | 0.0014 (3) |
C14 | 0.0174 (4) | 0.0103 (3) | 0.0163 (3) | −0.0002 (3) | 0.0008 (3) | 0.0007 (3) |
H14A | 0.02884 | 0.02531 | 0.03015 | 0.00059 | −0.00159 | 0.00128 |
C15 | 0.0254 (5) | 0.0107 (4) | 0.0234 (4) | 0.0006 (3) | 0.0027 (3) | 0.0008 (3) |
H15A | 0.05545 | 0.02564 | 0.03561 | −0.00341 | 0.00590 | −0.00391 |
H15B | 0.03858 | 0.03278 | 0.04333 | 0.00735 | 0.00189 | 0.00943 |
C16 | 0.0217 (4) | 0.0114 (4) | 0.0247 (4) | −0.0024 (3) | 0.0005 (3) | 0.0033 (3) |
H16A | 0.04979 | 0.03479 | 0.03763 | 0.00487 | 0.00473 | 0.01207 |
H16B | 0.04562 | 0.03061 | 0.04757 | −0.01112 | 0.00369 | −0.00302 |
C17 | 0.0183 (4) | 0.0134 (3) | 0.0173 (4) | −0.0016 (3) | −0.0009 (3) | 0.0032 (3) |
C20 | 0.0188 (4) | 0.0196 (4) | 0.0207 (4) | −0.0039 (3) | 0.0031 (3) | 0.0057 (3) |
C21 | 0.0184 (4) | 0.0300 (4) | 0.0231 (4) | −0.0015 (4) | 0.0040 (3) | 0.0024 (3) |
H21A | 0.02812 | 0.05058 | 0.04196 | −0.00902 | 0.00291 | 0.00112 |
H21B | 0.04008 | 0.03413 | 0.04070 | −0.00114 | 0.01412 | 0.00877 |
C22 | 0.0142 (4) | 0.0267 (4) | 0.0224 (4) | −0.0007 (3) | 0.0041 (3) | 0.0038 (3) |
C23 | 0.0185 (4) | 0.0440 (6) | 0.0224 (4) | 0.0032 (4) | 0.0063 (3) | 0.0017 (4) |
H23C | 0.05069 | 0.06468 | 0.04609 | −0.01514 | 0.01999 | −0.01164 |
H23B | 0.03490 | 0.08238 | 0.04503 | 0.01123 | 0.01324 | 0.00177 |
H23A | 0.05715 | 0.06131 | 0.03986 | 0.00343 | 0.01813 | 0.01233 |
C19 | 0.0196 (4) | 0.0304 (5) | 0.0169 (4) | −0.0076 (4) | 0.0026 (3) | −0.0042 (3) |
H19B | 0.04189 | 0.05378 | 0.03178 | −0.00677 | 0.00843 | −0.01835 |
H19C | 0.03806 | 0.03805 | 0.04272 | 0.00032 | −0.00164 | 0.00271 |
H19A | 0.03568 | 0.06169 | 0.03188 | −0.01637 | 0.00975 | 0.00370 |
C18 | 0.0192 (4) | 0.0166 (4) | 0.0168 (4) | −0.0029 (3) | −0.0009 (3) | 0.0024 (3) |
H18B | 0.03918 | 0.05433 | 0.03031 | 0.00592 | 0.00912 | −0.00427 |
H18C | 0.04861 | 0.02797 | 0.04552 | 0.00451 | −0.00061 | 0.00605 |
H18A | 0.02979 | 0.05142 | 0.03921 | −0.00969 | 0.00595 | 0.00817 |
HO2 | 0.03555 | 0.03418 | 0.02870 | −0.00561 | 0.01053 | −0.00989 |
HO3 | 0.03421 | 0.02842 | 0.03876 | −0.01077 | 0.00056 | 0.00348 |
Geometric parameters (Å, º) top
O5—C22 | 1.3561 (5) | C9—H9 | 1.0990 |
O5—C21 | 1.4299 (4) | C11—C12 | 1.5399 (4) |
O1—C3 | 1.2484 (4) | C11—H11 | 1.0990 |
O2—C11 | 1.4246 (4) | C12—C13 | 1.5310 (5) |
O2—HO2 | 0.9399 | C12—H12B | 1.0920 |
O3—C17 | 1.4349 (3) | C12—H12A | 1.0920 |
O3—HO3 | 0.9971 | C13—C17 | 1.5651 (4) |
O4—C20 | 1.2108 (5) | C13—C14 | 1.5413 (4) |
O6—C22 | 1.2036 (5) | C13—C18 | 1.5393 (3) |
C3—C4 | 1.4510 (5) | C14—C15 | 1.5379 (5) |
C3—C2 | 1.4598 (4) | C14—H14A | 1.0990 |
C2—C1 | 1.3401 (5) | C15—C16 | 1.5561 (4) |
C2—H2 | 1.0830 | C15—H15A | 1.0920 |
C1—C10 | 1.5032 (5) | C15—H15B | 1.0920 |
C1—H1 | 1.0830 | C16—C17 | 1.5478 (5) |
C10—C9 | 1.5817 (4) | C16—H16B | 1.0920 |
C10—C5 | 1.5089 (4) | C16—H16A | 1.0920 |
C10—C19 | 1.5558 (4) | C17—C20 | 1.5343 (4) |
C4—C5 | 1.3436 (4) | C20—C21 | 1.5308 (5) |
C4—H4 | 1.0830 | C21—H21A | 1.0920 |
C5—C6 | 1.4997 (5) | C21—H21B | 1.0920 |
C6—C7 | 1.5349 (4) | C22—C23 | 1.4983 (4) |
C6—H6A | 1.0920 | C23—H23C | 1.0770 |
C6—H6B | 1.0920 | C23—H23A | 1.0770 |
C7—C8 | 1.5355 (4) | C23—H23B | 1.0770 |
C7—H7B | 1.0920 | C19—H19A | 1.0770 |
C7—H7A | 1.0920 | C19—H19C | 1.0770 |
C8—C14 | 1.5284 (4) | C19—H19B | 1.0770 |
C8—C9 | 1.5484 (5) | C18—H18C | 1.0770 |
C8—H8 | 1.0990 | C18—H18A | 1.0770 |
C9—C11 | 1.5414 (4) | C18—H18B | 1.0770 |
| | | |
C22—O5—C21 | 114.5 (3) | C12—C11—H11 | 107.085 |
C11—O2—HO2 | 107.519 | C13—C12—H12B | 109.434 |
C17—O3—HO3 | 110.198 | C13—C12—H12A | 109.384 |
C4—C3—C2 | 117.8 (3) | H12B—C12—H12A | 107.287 |
C1—C2—H2 | 119.635 | C17—C13—C14 | 98.8 (2) |
C10—C1—C2 | 124.5 (3) | C17—C13—C12 | 115.1 (3) |
C10—C1—H1 | 117.383 | C17—C13—C18 | 109.4 (2) |
C9—C10—C5 | 106.8 (2) | C14—C13—C12 | 109.1 (3) |
C9—C10—C1 | 107.7 (3) | C14—C13—C18 | 112.3 (3) |
C9—C10—C19 | 115.1 (3) | C15—C14—H14A | 105.719 |
C5—C10—C1 | 112.2 (3) | C16—C15—H15A | 111.167 |
C5—C10—C19 | 107.3 (3) | C16—C15—H15B | 110.684 |
C5—C4—H4 | 119.510 | H15A—C15—H15B | 109.143 |
C6—C5—C4 | 121.1 (3) | C17—C16—C15 | 106.2 (3) |
C7—C6—H6A | 109.319 | C17—C16—H16B | 109.934 |
C7—C6—H6B | 109.486 | C17—C16—H16A | 110.559 |
H6A—C6—H6B | 107.990 | H16B—C16—H16A | 110.177 |
C8—C7—C6 | 112.0 (3) | C20—C17—C13 | 112.6 (3) |
C8—C7—H7B | 108.601 | C20—C17—C16 | 114.3 (3) |
C8—C7—H7A | 108.275 | H21A—C21—H21B | 109.303 |
H7B—C7—H7A | 108.507 | H23C—C23—H23A | 109.703 |
C14—C8—C9 | 107.1 (2) | H23C—C23—H23B | 111.095 |
C14—C8—C7 | 109.7 (3) | H23A—C23—H23B | 108.944 |
C14—C8—H8 | 110.443 | H19A—C19—H19C | 108.168 |
C9—C8—C7 | 110.3 (2) | H19A—C19—H19B | 110.592 |
C9—C8—H8 | 109.899 | H19C—C19—H19B | 109.165 |
C11—C9—C10 | 114.2 (2) | H18C—C18—H18A | 110.751 |
C11—C9—C8 | 114.0 (2) | H18C—C18—H18B | 109.978 |
C11—C9—H9 | 104.455 | H18A—C18—H18B | 110.566 |
| | | |
O5—C22—C23—H23C | 173.34 | H7B—C7—C8—C9 | −176.24 |
O5—C22—C23—H23A | −66.87 | H7B—C7—C8—H8 | −55.28 |
O5—C22—C23—H23B | 51.83 | C8—C14—C13—C17 | −179.54 (6) |
O5—C21—C20—O4 | −15.92 (7) | C8—C14—C13—C12 | −58.96 (6) |
O5—C21—C20—C17 | 164.73 (6) | C8—C14—C13—C18 | 65.20 (6) |
O1—C3—C4—C5 | 178.81 (2) | C8—C14—C15—C16 | −160.75 (6) |
O1—C3—C4—H4 | −0.75 | C8—C14—C15—H15A | 79.61 |
O1—C3—C2—C1 | 176.32 (5) | C8—C14—C15—H15B | −41.85 |
O1—C3—C2—H2 | −4.04 | C8—C9—C11—C12 | 50.52 (6) |
O2—C11—C9—C10 | 57.45 (6) | C8—C9—C11—H11 | 168.06 |
O2—C11—C9—C8 | −74.89 (6) | C8—C9—C10—C19 | 66.33 (6) |
O2—C11—C9—H9 | 171.06 | H8—C8—C14—C13 | −60.54 |
O2—C11—C12—C13 | 74.63 (6) | H8—C8—C14—C15 | 63.48 |
O2—C11—C12—H12B | −47.22 | H8—C8—C14—H14A | −177.31 |
O2—C11—C12—H12A | −163.52 | H8—C8—C9—C11 | 65.94 |
O3—C17—C20—O4 | −154.84 (14) | H8—C8—C9—H9 | 179.67 |
O3—C17—C20—C21 | 24.50 (8) | C9—C11—O2—HO2 | −172.65 |
O3—C17—C13—C14 | 72.68 (6) | C9—C11—C12—C13 | −48.94 (6) |
O3—C17—C13—C12 | −43.37 (7) | C9—C11—C12—H12B | −170.80 |
O3—C17—C13—C18 | −169.83 (6) | C9—C11—C12—H12A | 72.91 |
O3—C17—C16—C15 | −88.74 (6) | C9—C10—C19—H19A | −171.47 |
O3—C17—C16—H16B | 29.86 | C9—C10—C19—H19C | −53.10 |
O3—C17—C16—H16A | 151.72 | C9—C10—C19—H19B | 66.74 |
O4—C20—C17—C13 | 86.19 (7) | C9—C8—C14—C13 | 59.12 (6) |
O4—C20—C17—C16 | −30.24 (8) | C9—C8—C14—C15 | −176.87 (6) |
O4—C20—C21—H21A | 104.83 | C9—C8—C14—H14A | −57.65 |
O4—C20—C21—H21B | −135.86 | H9—C9—C11—C12 | −63.53 |
O6—C22—O5—C21 | 6.21 (6) | H9—C9—C11—H11 | 54.01 |
O6—C22—C23—H23C | −5.43 | H9—C9—C10—C19 | −179.93 |
O6—C22—C23—H23A | 114.36 | H9—C9—C8—C14 | 59.66 |
O6—C22—C23—H23B | −126.94 | C11—C9—C10—C19 | −66.38 (6) |
C3—C4—C5—C10 | 4.86 (5) | C11—C9—C8—C14 | −54.06 (6) |
C3—C4—C5—C6 | −172.10 (6) | C11—C12—C13—C17 | 161.87 (6) |
C3—C2—C1—C10 | 4.89 (5) | C11—C12—C13—C14 | 51.86 (6) |
C3—C2—C1—H1 | −175.33 | C11—C12—C13—C18 | −72.76 (6) |
C2—C3—C4—C5 | −2.05 (6) | H11—C11—O2—HO2 | −56.03 |
C2—C3—C4—H4 | 178.39 | H11—C11—C12—C13 | −166.70 |
C2—C1—C10—C9 | 115.16 (8) | H11—C11—C12—H12B | 71.44 |
C2—C1—C10—C5 | −2.16 (6) | H11—C11—C12—H12A | −44.86 |
C2—C1—C10—C19 | −120.11 (8) | C12—C11—O2—HO2 | 62.00 |
H2—C2—C3—C4 | 176.82 | C12—C13—C17—C20 | 75.09 (6) |
H2—C2—C1—C10 | −174.74 | C12—C13—C17—C16 | −161.59 (6) |
H2—C2—C1—H1 | 5.04 | C12—C13—C14—C15 | 168.73 (7) |
C1—C10—C9—C11 | 53.85 (6) | C12—C13—C14—H14A | 57.37 |
C1—C10—C9—C8 | −173.43 (6) | C12—C13—C18—H18C | −176.66 |
C1—C10—C9—H9 | −59.70 | C12—C13—C18—H18A | 62.90 |
C1—C10—C5—C6 | 174.28 (6) | C12—C13—C18—H18B | −57.25 |
C1—C10—C5—C4 | −2.82 (5) | H12A—C12—C13—C17 | 40.48 |
C1—C10—C19—H19A | 68.33 | H12A—C12—C13—C14 | −69.54 |
C1—C10—C19—H19C | −173.31 | H12A—C12—C13—C18 | 165.84 |
C1—C10—C19—H19B | −53.46 | H12B—C12—C13—C17 | −76.79 |
C1—C2—C3—C4 | −2.82 (6) | H12B—C12—C13—C14 | 173.19 |
H1—C1—C10—C9 | −64.62 | H12B—C12—C13—C18 | 48.57 |
H1—C1—C10—C5 | 178.06 | C13—C17—O3—HO3 | −152.55 |
H1—C1—C10—C19 | 60.11 | C13—C17—C20—C21 | −94.48 (7) |
C10—C9—C11—C12 | −177.14 (5) | C13—C17—C16—C15 | 26.90 (10) |
C10—C9—C11—H11 | −59.60 | C13—C17—C16—H16B | 145.50 |
C10—C9—C8—C14 | 173.13 (5) | C13—C17—C16—H16A | −92.64 |
C10—C9—C8—C7 | 53.79 (6) | C13—C14—C15—C16 | −31.96 (9) |
C10—C9—C8—H8 | −66.87 | C13—C14—C15—H15A | −151.60 |
C10—C5—C6—C7 | −59.15 (6) | C13—C14—C15—H15B | 86.94 |
C10—C5—C6—H6A | −179.32 | C14—C13—C17—C20 | −168.85 (6) |
C10—C5—C6—H6B | 61.27 | C14—C13—C17—C16 | −45.53 (8) |
C10—C5—C4—H4 | −175.59 | C14—C13—C18—H18C | 60.50 |
C4—C5—C10—C9 | −120.67 (8) | C14—C13—C18—H18A | −59.94 |
C4—C5—C10—C19 | 115.40 (7) | C14—C13—C18—H18B | 179.92 |
C4—C5—C6—C7 | 118.01 (8) | C14—C15—C16—C17 | 2.66 (6) |
C4—C5—C6—H6A | −2.17 | C14—C15—C16—H16B | −116.10 |
C4—C5—C6—H6B | −121.58 | C14—C15—C16—H16A | 122.42 |
H4—C4—C5—C6 | 7.46 | H14A—C14—C13—C17 | −63.21 |
C5—C10—C9—C11 | 174.60 (6) | H14A—C14—C13—C18 | −178.47 |
C5—C10—C9—C8 | −52.68 (6) | H14A—C14—C15—C16 | 80.00 |
C5—C10—C9—H9 | 61.06 | H14A—C14—C15—H15A | −39.65 |
C5—C10—C19—H19A | −52.72 | H14A—C14—C15—H15B | −161.10 |
C5—C10—C19—H19C | 65.64 | C15—C14—C13—C17 | 48.15 (8) |
C5—C10—C19—H19B | −174.51 | C15—C14—C13—C18 | −67.11 (6) |
C5—C6—C7—C8 | 55.89 (7) | C15—C16—C17—C20 | 149.07 (13) |
C5—C6—C7—H7B | 176.68 | H15A—C15—C16—C17 | 122.25 |
C5—C6—C7—H7A | −64.21 | H15A—C15—C16—H16B | 3.49 |
C6—C5—C10—C9 | 56.43 (6) | H15A—C15—C16—H16A | −117.99 |
C6—C5—C10—C19 | −67.50 (7) | H15B—C15—C16—C17 | −116.28 |
C6—C7—C8—C14 | −172.41 (6) | H15B—C15—C16—H16B | 124.97 |
C6—C7—C8—C9 | −54.68 (7) | H15B—C15—C16—H16A | 3.49 |
C6—C7—C8—H8 | 66.28 | C16—C17—O3—HO3 | −40.47 |
H6A—C6—C7—C8 | 176.75 | C16—C17—C20—C21 | 149.09 (14) |
H6A—C6—C7—H7B | −62.45 | C16—C17—C13—C18 | 71.95 (6) |
H6A—C6—C7—H7A | 56.65 | H16A—C16—C17—C20 | 29.53 |
H6B—C6—C7—C8 | −65.14 | H16B—C16—C17—C20 | −92.33 |
H6B—C6—C7—H7B | 55.66 | C17—C20—C21—H21A | −74.53 |
H6B—C6—C7—H7A | 174.77 | C17—C20—C21—H21B | 44.79 |
C7—C8—C14—C13 | 178.79 (6) | C17—C13—C18—H18C | −48.17 |
C7—C8—C14—C15 | −57.19 (6) | C17—C13—C18—H18A | −168.61 |
C7—C8—C14—H14A | 62.03 | C17—C13—C18—H18B | 71.24 |
C7—C8—C9—C11 | −173.40 (6) | C20—C17—O3—HO3 | 85.65 |
C7—C8—C9—H9 | −59.67 | C20—C17—C13—C18 | −51.37 (7) |
H7A—C7—C8—C14 | −51.61 | C20—C21—O5—C22 | −77.36 (7) |
H7A—C7—C8—C9 | 66.12 | C21—O5—C22—C23 | −172.60 (6) |
H7A—C7—C8—H8 | −172.92 | H21A—C21—O5—C22 | 161.38 |
H7B—C7—C8—C14 | 66.02 | H21B—C21—O5—C22 | 43.11 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—HO2···O1i | 0.94 | 1.88 | 2.8168 (4) | 172 |
O2—HO2···C3i | 0.94 | 2.69 | 3.5595 (3) | 154 |
O2—HO2···C4i | 0.94 | 2.89 | 3.5029 (1) | 124 |
C12—H12A···O3 | 1.09 | 2.37 | 2.8504 (5) | 105 |
C12—H12B···O6 | 1.09 | 2.47 | 3.4749 (2) | 153 |
C14—H14A···O3 | 1.10 | 2.39 | 2.8292 (2) | 102 |
C16—H16A···O4 | 1.09 | 2.53 | 2.9453 (3) | 101 |
C21—H21B···C12 | 1.09 | 2.81 | 3.5415 (3) | 124 |
C19—H19B···O2 | 1.08 | 2.27 | 2.8720 (2) | 113 |
C19—H19C···C8 | 1.08 | 2.87 | 3.2452 (6) | 100 |
C18—H18B···O4 | 1.08 | 2.68 | 3.0950 (3) | 103 |
C18—H18C···C16 | 1.08 | 2.52 | 2.9733 (5) | 104 |
C18—H18A···O2 | 1.08 | 2.40 | 3.0726 (6) | 119 |
C6—H6A···C2ii | 1.09 | 2.88 | 3.4322 (6) | 111 |
C7—H7B···O1ii | 1.09 | 2.68 | 3.5707 (6) | 139 |
C23—H23B···C6iii | 1.08 | 2.94 | 3.5917 (4) | 119 |
C16—H16B···O6iv | 1.09 | 2.69 | 3.5139 (7) | 132 |
C16—H16B···O1v | 1.09 | 2.45 | 3.3487 (2) | 138 |
O3—HO3···O1v | 1.00 | 1.73 | 2.7302 (5) | 176 |
O3—HO3···C3v | 1.00 | 2.66 | 3.5981 (6) | 157 |
Symmetry codes: (i) x, y, z−1; (ii) −x, y+1/2, −z+2; (iii) x+1, y, z−1; (iv) −x+1, y+1/2, −z+1; (v) −x+1, y+1/2, −z+2. |
2-[(8
S,9
S,10
R,13
S,14
S,17
R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3
H-cyclopenta[
a]phenanthren-17-yl]-2-oxoethyl
acetate (IAM_MoPro)
top
Crystal data top
C23H30O6 | F(000) = 432 |
Mr = 402.46 | Dx = 1.303 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 1200 reflections |
a = 8.4816 (1) Å | θ = 5.1–72.2° |
b = 13.865 (3) Å | µ = 0.76 mm−1 |
c = 8.9437 (1) Å | T = 100 K |
β = 102.709 (1)° | Block, colorless |
V = 1026.0 (2) Å3 | 0.43 × 0.34 × 0.21 mm |
Z = 2 | |
Data collection top
Bruker Kappa APEXII CMOS detector diffractometer | 4018 independent reflections |
Radiation source: Microfocus | 3976 reflections with > 2.0σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and φ scan | θmax = 72.2°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = 0→10 |
Tmin = 0.735, Tmax = 0.856 | k = −17→17 |
16242 measured reflections | l = −11→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.02P] where P = (Fo2 + 2Fc2)/3 |
S = 1.73 | (Δ/σ)max < 0.001 |
4018 reflections | Δρmax = 0.32 e Å−3 |
262 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (5) |
Special details top
Refinement. Refinement of F2 against reflections.
The threshold expression of F2 > 2sigma(F2) is
used for calculating R-factors(gt) 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 | x | y | z | Uiso*/Ueq | |
O5 | 0.70285 (15) | 0.5436 (5) | 0.22837 (14) | 0.02781 (14) | |
O1 | 0.18957 (14) | 0.2770 (5) | 1.26180 (12) | 0.02061 (13) | |
O2 | 0.12052 (15) | 0.3921 (5) | 0.49937 (13) | 0.02263 (13) | |
O3 | 0.62454 (15) | 0.6172 (5) | 0.65032 (13) | 0.02178 (13) | |
O4 | 0.48441 (17) | 0.6832 (5) | 0.26473 (14) | 0.03055 (16) | |
O6 | 0.48240 (15) | 0.4497 (5) | 0.20392 (15) | 0.02839 (14) | |
C3 | 0.15919 (19) | 0.3126 (5) | 1.13043 (18) | 0.01676 (16) | |
C2 | 0.1933 (2) | 0.2601 (5) | 0.99959 (19) | 0.01954 (18) | |
H2 | 0.25236 | 0.19047 | 1.01647 | 0.03693 | |
C1 | 0.1513 (2) | 0.2971 (5) | 0.85822 (19) | 0.01965 (18) | |
H1 | 0.16983 | 0.25270 | 0.76391 | 0.03530 | |
C10 | 0.0814 (2) | 0.3961 (5) | 0.82184 (17) | 0.01678 (17) | |
C4 | 0.08768 (19) | 0.4076 (5) | 1.10265 (17) | 0.01696 (16) | |
H4 | 0.05844 | 0.44722 | 1.19732 | 0.03176 | |
C5 | 0.05622 (18) | 0.4486 (5) | 0.96283 (17) | 0.01616 (16) | |
C6 | 0.0018 (2) | 0.5517 (5) | 0.94003 (19) | 0.01976 (18) | |
H6A | −0.01148 | 0.58279 | 1.04880 | 0.03472 | |
H6B | −0.11530 | 0.55556 | 0.85955 | 0.03544 | |
C7 | 0.1279 (2) | 0.6092 (5) | 0.87760 (18) | 0.02004 (18) | |
H7A | 0.24135 | 0.61091 | 0.96363 | 0.03302 | |
H7B | 0.08578 | 0.68329 | 0.85489 | 0.03629 | |
C8 | 0.1590 (2) | 0.5650 (5) | 0.72924 (17) | 0.01642 (17) | |
H8 | 0.05007 | 0.57165 | 0.63701 | 0.03016 | |
C9 | 0.20712 (19) | 0.4573 (5) | 0.75471 (16) | 0.01531 (16) | |
H9 | 0.31683 | 0.45814 | 0.84686 | 0.02710 | |
C11 | 0.2601 (2) | 0.4098 (5) | 0.61796 (17) | 0.01689 (17) | |
H11 | 0.31446 | 0.33964 | 0.65671 | 0.03358 | |
C12 | 0.3890 (2) | 0.4695 (5) | 0.56173 (18) | 0.01810 (17) | |
H12A | 0.50372 | 0.46335 | 0.64524 | 0.03282 | |
H12B | 0.40567 | 0.43921 | 0.45360 | 0.03400 | |
C13 | 0.34491 (19) | 0.5765 (5) | 0.53786 (17) | 0.01627 (17) | |
C14 | 0.3005 (2) | 0.6167 (5) | 0.68350 (17) | 0.01700 (17) | |
H14A | 0.40619 | 0.60375 | 0.77719 | 0.02935 | |
C15 | 0.2936 (2) | 0.7267 (5) | 0.65801 (19) | 0.0224 (2) | |
H15A | 0.32415 | 0.76506 | 0.76718 | 0.03954 | |
H15B | 0.17374 | 0.74911 | 0.59569 | 0.03932 | |
C16 | 0.4223 (2) | 0.7453 (5) | 0.5617 (2) | 0.02252 (19) | |
H16A | 0.36778 | 0.78080 | 0.45373 | 0.04149 | |
H16B | 0.51969 | 0.79068 | 0.62498 | 0.04228 | |
C17 | 0.4893 (2) | 0.6453 (5) | 0.53060 (18) | 0.01921 (18) | |
C20 | 0.5435 (2) | 0.6376 (5) | 0.37827 (19) | 0.02246 (18) | |
C21 | 0.6836 (2) | 0.5676 (5) | 0.3800 (2) | 0.02617 (19) | |
H21A | 0.79546 | 0.60015 | 0.44405 | 0.04096 | |
H21B | 0.66246 | 0.50157 | 0.43913 | 0.03750 | |
C22 | 0.5939 (2) | 0.4787 (5) | 0.1539 (2) | 0.02372 (18) | |
C23 | 0.6349 (2) | 0.4476 (5) | 0.0063 (2) | 0.0307 (2) | |
H23C | 0.55525 | 0.38982 | −0.04261 | 0.05238 | |
H23B | 0.75911 | 0.42434 | 0.02995 | 0.05341 | |
H23A | 0.61994 | 0.50826 | −0.07078 | 0.05162 | |
C19 | −0.0879 (2) | 0.3843 (5) | 0.71228 (19) | 0.02513 (19) | |
H19B | −0.07706 | 0.34078 | 0.61531 | 0.04243 | |
H19C | −0.13469 | 0.45419 | 0.67267 | 0.04123 | |
H19A | −0.16932 | 0.35025 | 0.77302 | 0.04272 | |
C18 | 0.2090 (2) | 0.5921 (5) | 0.39441 (18) | 0.02053 (18) | |
H18B | 0.24606 | 0.56279 | 0.29603 | 0.04105 | |
H18C | 0.18635 | 0.66820 | 0.37742 | 0.04239 | |
H18A | 0.10110 | 0.55599 | 0.40930 | 0.04039 | |
HO2 | 0.14975 | 0.36037 | 0.43279 | 0.03227 | |
HO3 | 0.68360 | 0.66466 | 0.67561 | 0.03495 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0213 (6) | 0.0375 (7) | 0.0263 (6) | −0.0045 (5) | 0.0088 (5) | 0.0020 (5) |
O1 | 0.0228 (6) | 0.0200 (5) | 0.0177 (5) | 0.0020 (4) | 0.0016 (4) | 0.0016 (4) |
O2 | 0.0267 (6) | 0.0246 (6) | 0.0172 (5) | −0.0077 (5) | 0.0061 (5) | −0.0066 (4) |
O3 | 0.0212 (6) | 0.0170 (5) | 0.0235 (5) | −0.0026 (4) | −0.0032 (4) | 0.0018 (4) |
O4 | 0.0360 (8) | 0.0275 (6) | 0.0272 (6) | −0.0024 (6) | 0.0048 (5) | 0.0112 (5) |
O6 | 0.0223 (6) | 0.0321 (7) | 0.0327 (6) | −0.0022 (5) | 0.0101 (5) | 0.0036 (5) |
C3 | 0.0144 (7) | 0.0175 (7) | 0.0176 (7) | −0.0024 (6) | 0.0017 (5) | −0.0007 (5) |
C2 | 0.0231 (8) | 0.0130 (7) | 0.0240 (8) | −0.0015 (6) | 0.0086 (6) | 0.0006 (6) |
H2 | 0.05198 | 0.02029 | 0.04067 | 0.00600 | 0.01486 | 0.00177 |
C1 | 0.0271 (9) | 0.0129 (7) | 0.0216 (7) | −0.0037 (6) | 0.0110 (6) | −0.0026 (6) |
H1 | 0.05127 | 0.02568 | 0.03145 | −0.00183 | 0.01453 | −0.00820 |
C10 | 0.0205 (8) | 0.0143 (7) | 0.0153 (7) | −0.0023 (6) | 0.0035 (6) | −0.0010 (5) |
C4 | 0.0150 (7) | 0.0191 (7) | 0.0160 (7) | −0.0008 (6) | 0.0017 (5) | −0.0023 (6) |
H4 | 0.03702 | 0.03372 | 0.02441 | 0.00708 | 0.00647 | −0.00476 |
C5 | 0.0147 (7) | 0.0159 (7) | 0.0176 (7) | −0.0001 (6) | 0.0028 (5) | −0.0017 (5) |
C6 | 0.0226 (8) | 0.0166 (7) | 0.0211 (7) | 0.0045 (6) | 0.0070 (6) | 0.0002 (6) |
H6A | 0.04309 | 0.03523 | 0.02583 | 0.00640 | 0.00755 | −0.00554 |
H6B | 0.02766 | 0.04292 | 0.03100 | 0.00496 | −0.00383 | 0.00265 |
C7 | 0.0254 (9) | 0.0133 (7) | 0.0220 (7) | 0.0029 (6) | 0.0067 (6) | −0.0006 (6) |
H7A | 0.02980 | 0.03530 | 0.03005 | 0.00236 | −0.00186 | −0.00186 |
H7B | 0.04588 | 0.02314 | 0.03965 | 0.01258 | 0.00901 | 0.00325 |
C8 | 0.0185 (7) | 0.0127 (6) | 0.0174 (7) | 0.0024 (6) | 0.0027 (6) | 0.0009 (5) |
H8 | 0.02696 | 0.03339 | 0.02688 | 0.00318 | −0.00114 | 0.00091 |
C9 | 0.0189 (7) | 0.0127 (7) | 0.0143 (7) | −0.0004 (6) | 0.0036 (5) | −0.0010 (5) |
H9 | 0.02539 | 0.02517 | 0.02792 | 0.00011 | −0.00027 | −0.00141 |
C11 | 0.0220 (8) | 0.0125 (7) | 0.0171 (7) | −0.0015 (6) | 0.0063 (6) | −0.0009 (5) |
H11 | 0.03951 | 0.02142 | 0.04180 | 0.00315 | 0.01323 | 0.00261 |
C12 | 0.0217 (8) | 0.0132 (7) | 0.0200 (7) | −0.0013 (6) | 0.0060 (6) | 0.0014 (5) |
H12A | 0.02819 | 0.03069 | 0.03622 | −0.00102 | −0.00017 | 0.00353 |
H12B | 0.04324 | 0.03091 | 0.03047 | −0.00279 | 0.01374 | −0.00487 |
C13 | 0.0179 (7) | 0.0132 (7) | 0.0169 (7) | −0.0012 (6) | 0.0023 (6) | 0.0020 (5) |
C14 | 0.0193 (8) | 0.0123 (7) | 0.0180 (7) | 0.0004 (6) | 0.0009 (6) | 0.0001 (5) |
H14A | 0.02884 | 0.02531 | 0.03015 | 0.00059 | −0.00159 | 0.00128 |
C15 | 0.0283 (9) | 0.0126 (7) | 0.0253 (8) | 0.0005 (6) | 0.0034 (6) | 0.0003 (6) |
H15A | 0.05545 | 0.02564 | 0.03561 | −0.00341 | 0.00590 | −0.00391 |
H15B | 0.03858 | 0.03278 | 0.04333 | 0.00735 | 0.00189 | 0.00943 |
C16 | 0.0256 (9) | 0.0125 (7) | 0.0274 (8) | −0.0017 (6) | 0.0013 (6) | 0.0031 (6) |
H16A | 0.04979 | 0.03479 | 0.03763 | 0.00487 | 0.00473 | 0.01207 |
H16B | 0.04562 | 0.03061 | 0.04757 | −0.01112 | 0.00369 | −0.00302 |
C17 | 0.0201 (8) | 0.0142 (7) | 0.0211 (7) | −0.0020 (6) | −0.0004 (6) | 0.0033 (6) |
C20 | 0.0207 (8) | 0.0209 (7) | 0.0248 (8) | −0.0076 (6) | 0.0028 (6) | 0.0043 (6) |
C21 | 0.0211 (8) | 0.0355 (9) | 0.0219 (8) | −0.0012 (7) | 0.0048 (6) | 0.0012 (7) |
H21A | 0.02812 | 0.05058 | 0.04196 | −0.00902 | 0.00291 | 0.00112 |
H21B | 0.04008 | 0.03413 | 0.04070 | −0.00114 | 0.01412 | 0.00877 |
C22 | 0.0163 (8) | 0.0282 (9) | 0.0259 (8) | 0.0030 (6) | 0.0031 (6) | 0.0057 (6) |
C23 | 0.0203 (8) | 0.0460 (11) | 0.0263 (8) | 0.0045 (8) | 0.0066 (7) | 0.0032 (8) |
H23C | 0.05069 | 0.06468 | 0.04609 | −0.01514 | 0.01999 | −0.01164 |
H23B | 0.03490 | 0.08238 | 0.04503 | 0.01123 | 0.01324 | 0.00177 |
H23A | 0.05715 | 0.06131 | 0.03986 | 0.00343 | 0.01813 | 0.01233 |
C19 | 0.0216 (9) | 0.0333 (9) | 0.0199 (7) | −0.0079 (7) | 0.0033 (6) | −0.0033 (6) |
H19B | 0.04189 | 0.05378 | 0.03178 | −0.00677 | 0.00843 | −0.01835 |
H19C | 0.03806 | 0.03805 | 0.04272 | 0.00032 | −0.00164 | 0.00271 |
H19A | 0.03568 | 0.06169 | 0.03188 | −0.01637 | 0.00975 | 0.00370 |
C18 | 0.0214 (8) | 0.0195 (8) | 0.0182 (7) | −0.0030 (6) | −0.0009 (6) | 0.0024 (6) |
H18B | 0.03918 | 0.05433 | 0.03031 | 0.00592 | 0.00912 | −0.00427 |
H18C | 0.04861 | 0.02797 | 0.04552 | 0.00451 | −0.00061 | 0.00605 |
H18A | 0.02979 | 0.05142 | 0.03921 | −0.00969 | 0.00595 | 0.00817 |
HO2 | 0.03555 | 0.03418 | 0.02870 | −0.00561 | 0.01053 | −0.00989 |
HO3 | 0.03421 | 0.02842 | 0.03876 | −0.01077 | 0.00056 | 0.00348 |
Geometric parameters (Å, º) top
O5—C22 | 1.3550 (9) | C9—H9 | 1.0990 |
O5—C21 | 1.4408 (7) | C11—C12 | 1.5412 (7) |
O1—C3 | 1.2476 (8) | C11—H11 | 1.0990 |
O2—C11 | 1.4266 (7) | C12—C13 | 1.5333 (8) |
O2—HO2 | 0.8210 | C12—H12B | 1.0920 |
O3—C17 | 1.4398 (7) | C12—H12A | 1.0920 |
O3—HO3 | 0.8275 | C13—C17 | 1.5642 (7) |
O4—C20 | 1.2073 (9) | C13—C14 | 1.5378 (7) |
O6—C22 | 1.2008 (9) | C13—C18 | 1.5397 (7) |
C3—C4 | 1.4489 (8) | C14—C15 | 1.5410 (8) |
C3—C2 | 1.4597 (7) | C14—H14A | 1.0990 |
C2—C1 | 1.3379 (9) | C15—C16 | 1.5535 (8) |
C2—H2 | 1.0830 | C15—H15A | 1.0920 |
C1—C10 | 1.5029 (8) | C15—H15B | 1.0920 |
C1—H1 | 1.0830 | C16—C17 | 1.5472 (8) |
C10—C9 | 1.5812 (7) | C16—H16B | 1.0920 |
C10—C5 | 1.5111 (7) | C16—H16A | 1.0920 |
C10—C19 | 1.5585 (7) | C17—C20 | 1.5344 (7) |
C4—C5 | 1.3459 (8) | C20—C21 | 1.5313 (9) |
C4—H4 | 1.0830 | C21—H21A | 1.0920 |
C5—C6 | 1.5029 (8) | C21—H21B | 1.0920 |
C6—C7 | 1.5342 (8) | C22—C23 | 1.5007 (8) |
C6—H6B | 1.0920 | C23—H23C | 1.0770 |
C6—H6A | 1.0920 | C23—H23A | 1.0770 |
C7—C8 | 1.5362 (7) | C23—H23B | 1.0770 |
C7—H7A | 1.0920 | C19—H19B | 1.0770 |
C7—H7B | 1.0920 | C19—H19C | 1.0770 |
C8—C14 | 1.5283 (7) | C19—H19A | 1.0770 |
C8—C9 | 1.5510 (7) | C18—H18B | 1.0770 |
C8—H8 | 1.0990 | C18—H18A | 1.0770 |
C9—C11 | 1.5410 (6) | C18—H18C | 1.0770 |
| | | |
C22—O5—C21 | 114.2 (6) | C12—C11—H11 | 107.488 |
C11—O2—HO2 | 107.316 | C13—C12—H12B | 108.931 |
C17—O3—HO3 | 108.908 | C13—C12—H12A | 108.935 |
C4—C3—C2 | 117.7 (6) | H12B—C12—H12A | 107.810 |
C1—C2—H2 | 119.468 | C17—C13—C14 | 98.9 (5) |
C10—C1—C2 | 124.4 (6) | C17—C13—C12 | 115.2 (5) |
C10—C1—H1 | 117.932 | C17—C13—C18 | 109.2 (5) |
C9—C10—C5 | 106.8 (5) | C14—C13—C12 | 109.3 (5) |
C9—C10—C1 | 107.8 (5) | C14—C13—C18 | 112.1 (5) |
C9—C10—C19 | 115.0 (5) | C15—C14—H14A | 105.785 |
C5—C10—C1 | 112.4 (5) | C16—C15—H15A | 110.939 |
C5—C10—C19 | 107.2 (5) | C16—C15—H15B | 111.013 |
C5—C4—H4 | 118.645 | H15A—C15—H15B | 109.165 |
C6—C5—C4 | 121.4 (6) | C17—C16—C15 | 106.3 (5) |
C7—C6—H6B | 109.928 | C17—C16—H16B | 110.123 |
C7—C6—H6A | 109.654 | C17—C16—H16A | 110.236 |
H6B—C6—H6A | 108.132 | H16B—C16—H16A | 108.874 |
C8—C7—C6 | 111.9 (5) | C20—C17—C13 | 112.7 (5) |
C8—C7—H7A | 108.971 | C20—C17—C16 | 114.5 (6) |
C8—C7—H7B | 109.036 | H21A—C21—H21B | 107.970 |
H7A—C7—H7B | 108.185 | H23C—C23—H23A | 110.225 |
C14—C8—C9 | 107.1 (5) | H23C—C23—H23B | 110.861 |
C14—C8—C7 | 109.8 (5) | H23A—C23—H23B | 109.411 |
C14—C8—H8 | 109.854 | H19B—C19—H19C | 109.255 |
C9—C8—C7 | 110.3 (5) | H19B—C19—H19A | 109.779 |
C9—C8—H8 | 109.982 | H19C—C19—H19A | 109.250 |
C11—C9—C10 | 114.3 (5) | H18B—C18—H18A | 109.511 |
C11—C9—C8 | 114.1 (5) | H18B—C18—H18C | 109.244 |
C11—C9—H9 | 104.643 | H18A—C18—H18C | 110.049 |
| | | |
O5—C22—C23—H23C | 172.97 | H7B—C7—C8—C9 | −175.89 |
O5—C22—C23—H23A | −66.86 | H7B—C7—C8—H8 | −54.54 |
O5—C22—C23—H23B | 52.12 | C8—C14—C13—C17 | −179.67 (11) |
O5—C21—C20—O4 | −16.11 (13) | C8—C14—C13—C12 | −58.90 (12) |
O5—C21—C20—C17 | 164.83 (12) | C8—C14—C13—C18 | 65.27 (12) |
O1—C3—C4—C5 | 178.76 (5) | C8—C14—C15—C16 | −160.94 (11) |
O1—C3—C4—H4 | −1.21 | C8—C14—C15—H15A | 79.88 |
O1—C3—C2—C1 | 176.13 (9) | C8—C14—C15—H15B | −41.62 |
O1—C3—C2—H2 | −3.51 | C8—C9—C11—C12 | 50.37 (12) |
O2—C11—C9—C10 | 57.58 (11) | C8—C9—C11—H11 | 168.54 |
O2—C11—C9—C8 | −74.95 (11) | C8—C9—C10—C19 | 66.34 (12) |
O2—C11—C9—H9 | 171.34 | H8—C8—C14—C13 | −60.52 |
O2—C11—C12—C13 | 74.57 (11) | H8—C8—C14—C15 | 63.71 |
O2—C11—C12—H12B | −46.76 | H8—C8—C14—H14A | −176.87 |
O2—C11—C12—H12A | −163.99 | H8—C8—C9—C11 | 65.55 |
O3—C17—C20—O4 | −154.9 (3) | H8—C8—C9—H9 | 179.29 |
O3—C17—C20—C21 | 24.14 (17) | C9—C11—O2—HO2 | −172.56 |
O3—C17—C13—C14 | 72.92 (12) | C9—C11—C12—C13 | −48.78 (12) |
O3—C17—C13—C12 | −43.38 (13) | C9—C11—C12—H12B | −170.11 |
O3—C17—C13—C18 | −169.78 (11) | C9—C11—C12—H12A | 72.66 |
O3—C17—C16—C15 | −88.72 (12) | C9—C10—C19—H19B | 67.20 |
O3—C17—C16—H16B | 31.15 | C9—C10—C19—H19C | −52.63 |
O3—C17—C16—H16A | 151.30 | C9—C10—C19—H19A | −172.37 |
O4—C20—C17—C13 | 86.51 (13) | C9—C8—C14—C13 | 58.91 (12) |
O4—C20—C17—C16 | −30.16 (15) | C9—C8—C14—C15 | −176.86 (12) |
O4—C20—C21—H21A | 104.92 | C9—C8—C14—H14A | −57.44 |
O4—C20—C21—H21B | −137.36 | H9—C9—C11—C12 | −63.35 |
O6—C22—O5—C21 | 6.07 (12) | H9—C9—C11—H11 | 54.83 |
O6—C22—C23—H23C | −5.58 | H9—C9—C10—C19 | 179.61 |
O6—C22—C23—H23A | 114.59 | H9—C9—C8—C14 | 59.94 |
O6—C22—C23—H23B | −126.43 | C11—C9—C10—C19 | −66.59 (12) |
C3—C4—C5—C10 | 4.63 (10) | C11—C9—C8—C14 | −53.80 (12) |
C3—C4—C5—C6 | −172.17 (12) | C11—C12—C13—C17 | 161.99 (11) |
C3—C2—C1—C10 | 5.58 (10) | C11—C12—C13—C14 | 51.76 (13) |
C3—C2—C1—H1 | −174.82 | C11—C12—C13—C18 | −72.78 (12) |
C2—C3—C4—C5 | −1.57 (11) | H11—C11—O2—HO2 | −56.06 |
C2—C3—C4—H4 | 178.46 | H11—C11—C12—C13 | −167.07 |
C2—C1—C10—C9 | 114.88 (15) | H11—C11—C12—H12B | 71.60 |
C2—C1—C10—C5 | −2.53 (11) | H11—C11—C12—H12A | −45.62 |
C2—C1—C10—C19 | −120.44 (16) | C12—C11—O2—HO2 | 62.18 |
H2—C2—C3—C4 | 176.83 | C12—C13—C17—C20 | 74.82 (12) |
H2—C2—C1—C10 | −174.78 | C12—C13—C17—C16 | −161.57 (12) |
H2—C2—C1—H1 | 4.82 | C12—C13—C14—C15 | 168.74 (13) |
C1—C10—C9—C11 | 53.64 (12) | C12—C13—C14—H14A | 57.46 |
C1—C10—C9—C8 | −173.43 (11) | C12—C13—C18—H18B | −57.05 |
C1—C10—C9—H9 | −60.16 | C12—C13—C18—H18A | 62.78 |
C1—C10—C5—C6 | 174.29 (12) | C12—C13—C18—H18C | −176.57 |
C1—C10—C5—C4 | −2.67 (11) | H12A—C12—C13—C17 | 40.57 |
C1—C10—C19—H19B | −53.03 | H12A—C12—C13—C14 | −69.66 |
C1—C10—C19—H19C | −172.86 | H12A—C12—C13—C18 | 165.80 |
C1—C10—C19—H19A | 67.40 | H12B—C12—C13—C17 | −76.79 |
C1—C2—C3—C4 | −3.53 (11) | H12B—C12—C13—C14 | 172.98 |
H1—C1—C10—C9 | −64.72 | H12B—C12—C13—C18 | 48.44 |
H1—C1—C10—C5 | 177.86 | C13—C17—O3—HO3 | −153.48 |
H1—C1—C10—C19 | 59.96 | C13—C17—C20—C21 | −94.46 (13) |
C10—C9—C11—C12 | −177.10 (10) | C13—C17—C16—C15 | 26.7 (2) |
C10—C9—C11—H11 | −58.93 | C13—C17—C16—H16B | 146.53 |
C10—C9—C8—C14 | 173.20 (11) | C13—C17—C16—H16A | −93.32 |
C10—C9—C8—C7 | 53.79 (12) | C13—C14—C15—C16 | −31.92 (18) |
C10—C9—C8—H8 | −67.46 | C13—C14—C15—H15A | −151.10 |
C10—C5—C6—C7 | −59.20 (12) | C13—C14—C15—H15B | 87.39 |
C10—C5—C6—H6B | 61.43 | C14—C13—C17—C20 | −168.89 (12) |
C10—C5—C6—H6A | −179.48 | C14—C13—C17—C16 | −45.28 (16) |
C10—C5—C4—H4 | −175.40 | C14—C13—C18—H18B | −179.97 |
C4—C5—C10—C9 | −120.66 (15) | C14—C13—C18—H18A | −60.13 |
C4—C5—C10—C19 | 115.58 (14) | C14—C13—C18—H18C | 60.52 |
C4—C5—C6—C7 | 117.80 (15) | C14—C15—C16—C17 | 2.74 (12) |
C4—C5—C6—H6B | −121.57 | C14—C15—C16—H16B | −116.81 |
C4—C5—C6—H6A | −2.48 | C14—C15—C16—H16A | 122.45 |
H4—C4—C5—C6 | 7.80 | H14A—C14—C13—C17 | −63.31 |
C5—C10—C9—C11 | 174.61 (11) | H14A—C14—C13—C18 | −178.37 |
C5—C10—C9—C8 | −52.46 (12) | H14A—C14—C15—C16 | 79.52 |
C5—C10—C9—H9 | 60.81 | H14A—C14—C15—H15A | −39.66 |
C5—C10—C19—H19B | −174.23 | H14A—C14—C15—H15B | −161.16 |
C5—C10—C19—H19C | 65.95 | C15—C14—C13—C17 | 47.97 (15) |
C5—C10—C19—H19A | −53.80 | C15—C14—C13—C18 | −67.09 (12) |
C5—C6—C7—C8 | 56.04 (13) | C15—C16—C17—C20 | 149.0 (3) |
C5—C6—C7—H7A | −64.82 | H15A—C15—C16—C17 | 121.88 |
C5—C6—C7—H7B | 176.92 | H15A—C15—C16—H16B | 2.33 |
C6—C5—C10—C9 | 56.30 (12) | H15A—C15—C16—H16A | −118.42 |
C6—C5—C10—C19 | −67.46 (13) | H15B—C15—C16—C17 | −116.55 |
C6—C7—C8—C14 | −172.66 (12) | H15B—C15—C16—H16B | 123.90 |
C6—C7—C8—C9 | −54.87 (13) | H15B—C15—C16—H16A | 3.15 |
C6—C7—C8—H8 | 66.48 | C16—C17—O3—HO3 | −41.45 |
H6A—C6—C7—C8 | 176.57 | C16—C17—C20—C21 | 148.9 (3) |
H6A—C6—C7—H7A | 55.71 | C16—C17—C13—C18 | 72.02 (12) |
H6A—C6—C7—H7B | −62.55 | H16A—C16—C17—C20 | 29.03 |
H6B—C6—C7—C8 | −64.68 | H16B—C16—C17—C20 | −91.11 |
H6B—C6—C7—H7A | 174.46 | C17—C20—C21—H21A | −74.14 |
H6B—C6—C7—H7B | 56.20 | C17—C20—C21—H21B | 43.58 |
C7—C8—C14—C13 | 178.65 (12) | C17—C13—C18—H18B | 71.44 |
C7—C8—C14—C15 | −57.11 (13) | C17—C13—C18—H18A | −168.73 |
C7—C8—C14—H14A | 62.30 | C17—C13—C18—H18C | −48.08 |
C7—C8—C9—C11 | −173.21 (12) | C20—C17—O3—HO3 | 84.89 |
C7—C8—C9—H9 | −59.47 | C20—C17—C13—C18 | −51.58 (13) |
H7A—C7—C8—C14 | −51.57 | C20—C21—O5—C22 | −77.25 (13) |
H7A—C7—C8—C9 | 66.22 | C21—O5—C22—C23 | −172.53 (12) |
H7A—C7—C8—H8 | −172.42 | H21A—C21—O5—C22 | 161.62 |
H7B—C7—C8—C14 | 66.32 | H21B—C21—O5—C22 | 44.04 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—HO2···O1i | 0.82 | 2.00 | 2.8195 (4) | 172 |
O2—HO2···C3i | 0.82 | 2.80 | 3.5618 (4) | 155 |
C12—H12A···O3 | 1.09 | 2.36 | 2.8488 (6) | 105 |
C12—H12B···O6 | 1.09 | 2.46 | 3.4728 (3) | 153 |
C14—H14A···O3 | 1.10 | 2.38 | 2.8288 (4) | 102 |
C16—H16A···O4 | 1.09 | 2.53 | 2.9478 (4) | 101 |
C21—H21B···C12 | 1.09 | 2.81 | 3.5384 (4) | 124 |
C19—H19B···O2 | 1.08 | 2.27 | 2.8712 (4) | 113 |
C19—H19C···C8 | 1.08 | 2.88 | 3.2475 (7) | 100 |
C18—H18B···O4 | 1.08 | 2.68 | 3.0965 (4) | 102 |
C18—H18C···C16 | 1.08 | 2.53 | 2.9719 (6) | 103 |
C18—H18A···O2 | 1.08 | 2.40 | 3.0738 (7) | 119 |
C6—H6A···C2ii | 1.09 | 2.88 | 3.4304 (7) | 111 |
C7—H7B···O1ii | 1.09 | 2.68 | 3.5697 (6) | 139 |
C16—H16B···O6iii | 1.09 | 2.69 | 3.5120 (7) | 132 |
C16—H16B···O1iv | 1.09 | 2.46 | 3.3518 (3) | 138 |
O3—HO3···O1iv | 0.83 | 1.91 | 2.7325 (6) | 177 |
Symmetry codes: (i) x, y, z−1; (ii) −x, y+1/2, −z+2; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y+1/2, −z+2. |
2-[(8
S,9
S,10
R,13
S,14
S,17
R)-11,17-Dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3
H-cyclopenta[
a]phenanthren-17-yl]-2-oxoethyl
acetate (IAM_shelx)
top
Crystal data top
C23H30O6 | F(000) = 432 |
Mr = 402.46 | Dx = 1.303 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 8.4816 (19) Å | Cell parameters from 1200 reflections |
b = 13.865 (3) Å | θ = 5.1–72.2° |
c = 8.9437 (19) Å | µ = 0.76 mm−1 |
β = 102.709 (17)° | T = 100 K |
V = 1026.0 (4) Å3 | Block, colorless |
Z = 2 | 0.43 × 0.34 × 0.21 mm |
Data collection top
Bruker Kappa Apex II CMOS detector diffractometer | 4018 independent reflections |
Radiation source: Microfocus | 3942 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and phi scan | θmax = 72.2°, θmin = 5.1° |
Absorption correction: multi-scan SADABS (Krause et al., 2015) | h = −10→10 |
Tmin = 0.735, Tmax = 0.856 | k = −17→17 |
16242 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.0391P)2 + 0.1219P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.067 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.22 e Å−3 |
4018 reflections | Δρmin = −0.16 e Å−3 |
271 parameters | Absolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.01 (5) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O5 | 0.70295 (16) | 0.54102 (11) | 0.22842 (15) | 0.0275 (3) | |
O1 | 0.18982 (15) | 0.27450 (9) | 1.26188 (13) | 0.0200 (3) | |
O2 | 0.12030 (16) | 0.38966 (10) | 0.49946 (14) | 0.0220 (3) | |
O3 | 0.62443 (16) | 0.61465 (9) | 0.65034 (14) | 0.0214 (3) | |
O4 | 0.48451 (18) | 0.68073 (10) | 0.26480 (15) | 0.0296 (3) | |
O6 | 0.48224 (16) | 0.44716 (10) | 0.20361 (16) | 0.0281 (3) | |
C3 | 0.1594 (2) | 0.31013 (12) | 1.13048 (19) | 0.0165 (3) | |
C2 | 0.1930 (2) | 0.25744 (12) | 0.9996 (2) | 0.0190 (3) | |
H2 | 0.2436 | 0.1976 | 1.0144 | 0.023* | |
C1 | 0.1517 (2) | 0.29462 (12) | 0.8587 (2) | 0.0194 (3) | |
H1 | 0.1675 | 0.2566 | 0.7776 | 0.023* | |
C10 | 0.0814 (2) | 0.39354 (12) | 0.82181 (18) | 0.0165 (3) | |
C4 | 0.0878 (2) | 0.40496 (12) | 1.10240 (18) | 0.0164 (3) | |
H4 | 0.0626 | 0.4388 | 1.1839 | 0.020* | |
C5 | 0.05656 (19) | 0.44584 (12) | 0.96305 (18) | 0.0158 (3) | |
C6 | 0.0020 (2) | 0.54896 (12) | 0.9400 (2) | 0.0194 (3) | |
H6A | −0.0099 | 0.5764 | 1.0367 | 0.023* | |
H6B | −0.1019 | 0.5521 | 0.8684 | 0.023* | |
C7 | 0.1278 (2) | 0.60634 (12) | 0.87749 (19) | 0.0196 (3) | |
H7A | 0.2283 | 0.6081 | 0.9542 | 0.024* | |
H7B | 0.0904 | 0.6722 | 0.8578 | 0.024* | |
C8 | 0.1591 (2) | 0.56236 (12) | 0.72924 (18) | 0.0163 (3) | |
H8 | 0.0620 | 0.5682 | 0.6468 | 0.020* | |
C9 | 0.2072 (2) | 0.45466 (11) | 0.75470 (17) | 0.0151 (3) | |
H9 | 0.3051 | 0.4554 | 0.8368 | 0.018* | |
C11 | 0.2602 (2) | 0.40727 (12) | 0.61802 (18) | 0.0169 (3) | |
H11 | 0.3084 | 0.3446 | 0.6525 | 0.020* | |
C12 | 0.3888 (2) | 0.46692 (12) | 0.56175 (19) | 0.0176 (3) | |
H12A | 0.4908 | 0.4615 | 0.6359 | 0.021* | |
H12B | 0.4039 | 0.4400 | 0.4657 | 0.021* | |
C13 | 0.3448 (2) | 0.57391 (11) | 0.53781 (18) | 0.0163 (3) | |
C14 | 0.3007 (2) | 0.61395 (12) | 0.68386 (19) | 0.0174 (3) | |
H14A | 0.3949 | 0.6022 | 0.7674 | 0.021* | |
C15 | 0.2937 (2) | 0.72406 (12) | 0.6583 (2) | 0.0223 (4) | |
H15A | 0.3205 | 0.7583 | 0.7551 | 0.027* | |
H15B | 0.1872 | 0.7440 | 0.6028 | 0.027* | |
C16 | 0.4227 (2) | 0.74252 (12) | 0.5618 (2) | 0.0220 (4) | |
H16A | 0.3740 | 0.7743 | 0.4662 | 0.026* | |
H16B | 0.5087 | 0.7831 | 0.6180 | 0.026* | |
C17 | 0.4896 (2) | 0.64275 (12) | 0.53063 (19) | 0.0188 (4) | |
C20 | 0.5438 (2) | 0.63512 (13) | 0.3783 (2) | 0.0223 (4) | |
C21 | 0.6833 (2) | 0.56530 (15) | 0.3798 (2) | 0.0259 (4) | |
H21A | 0.7826 | 0.5941 | 0.4370 | 0.031* | |
H21B | 0.6645 | 0.5067 | 0.4324 | 0.031* | |
C22 | 0.5940 (2) | 0.47608 (14) | 0.1537 (2) | 0.0235 (4) | |
C23 | 0.6351 (2) | 0.44493 (17) | 0.0067 (2) | 0.0295 (4) | |
H23C | 0.5649 | 0.3932 | −0.0374 | 0.044* | |
H23B | 0.7453 | 0.4233 | 0.0266 | 0.044* | |
H23A | 0.6215 | 0.4983 | −0.0634 | 0.044* | |
C19 | −0.0876 (2) | 0.38162 (14) | 0.7126 (2) | 0.0243 (4) | |
H19B | −0.0779 | 0.3426 | 0.6264 | 0.036* | |
H19C | −0.1294 | 0.4439 | 0.6772 | 0.036* | |
H19A | −0.1600 | 0.3510 | 0.7667 | 0.036* | |
C18 | 0.2089 (2) | 0.58936 (12) | 0.39423 (19) | 0.0200 (4) | |
H18B | 0.2414 | 0.5632 | 0.3063 | 0.030* | |
H18C | 0.1881 | 0.6571 | 0.3793 | 0.030* | |
H18A | 0.1125 | 0.5574 | 0.4076 | 0.030* | |
HO2 | 0.148 (3) | 0.3583 (18) | 0.434 (3) | 0.030* | |
HO3 | 0.685 (3) | 0.665 (2) | 0.676 (3) | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0202 (7) | 0.0374 (7) | 0.0263 (7) | −0.0039 (5) | 0.0084 (5) | 0.0018 (6) |
O1 | 0.0226 (6) | 0.0192 (6) | 0.0171 (6) | 0.0020 (5) | 0.0019 (5) | 0.0019 (4) |
O2 | 0.0263 (7) | 0.0238 (6) | 0.0167 (6) | −0.0077 (5) | 0.0064 (5) | −0.0074 (5) |
O3 | 0.0199 (6) | 0.0164 (6) | 0.0238 (6) | −0.0024 (5) | −0.0038 (5) | 0.0016 (5) |
O4 | 0.0346 (8) | 0.0273 (7) | 0.0259 (7) | −0.0020 (6) | 0.0047 (6) | 0.0105 (6) |
O6 | 0.0228 (7) | 0.0320 (7) | 0.0318 (7) | −0.0024 (6) | 0.0106 (5) | 0.0031 (6) |
C3 | 0.0134 (7) | 0.0170 (8) | 0.0185 (8) | −0.0025 (6) | 0.0021 (6) | −0.0002 (6) |
C2 | 0.0229 (8) | 0.0111 (7) | 0.0247 (8) | −0.0001 (6) | 0.0089 (7) | 0.0005 (6) |
C1 | 0.0266 (9) | 0.0128 (8) | 0.0213 (8) | −0.0040 (7) | 0.0109 (7) | −0.0043 (6) |
C10 | 0.0209 (8) | 0.0142 (8) | 0.0145 (7) | −0.0020 (7) | 0.0039 (6) | −0.0008 (6) |
C4 | 0.0154 (8) | 0.0179 (8) | 0.0157 (7) | −0.0003 (6) | 0.0031 (6) | −0.0032 (6) |
C5 | 0.0132 (7) | 0.0155 (8) | 0.0184 (8) | −0.0003 (6) | 0.0029 (6) | −0.0024 (6) |
C6 | 0.0221 (9) | 0.0171 (8) | 0.0198 (8) | 0.0049 (7) | 0.0060 (7) | −0.0003 (6) |
C7 | 0.0239 (9) | 0.0131 (7) | 0.0218 (8) | 0.0032 (7) | 0.0052 (7) | −0.0010 (6) |
C8 | 0.0186 (8) | 0.0130 (7) | 0.0163 (8) | 0.0021 (6) | 0.0018 (6) | 0.0007 (6) |
C9 | 0.0179 (8) | 0.0125 (7) | 0.0143 (7) | −0.0005 (6) | 0.0021 (6) | −0.0004 (6) |
C11 | 0.0225 (9) | 0.0111 (7) | 0.0176 (7) | −0.0012 (6) | 0.0053 (6) | 0.0000 (6) |
C12 | 0.0203 (8) | 0.0142 (8) | 0.0189 (7) | −0.0010 (6) | 0.0058 (6) | 0.0014 (6) |
C13 | 0.0177 (8) | 0.0135 (7) | 0.0168 (8) | −0.0022 (6) | 0.0019 (6) | 0.0019 (6) |
C14 | 0.0200 (9) | 0.0126 (7) | 0.0179 (7) | 0.0003 (6) | 0.0005 (6) | 0.0004 (6) |
C15 | 0.0271 (10) | 0.0133 (8) | 0.0247 (9) | 0.0009 (7) | 0.0021 (7) | 0.0002 (6) |
C16 | 0.0241 (9) | 0.0126 (8) | 0.0263 (9) | −0.0024 (7) | −0.0005 (7) | 0.0032 (6) |
C17 | 0.0194 (9) | 0.0147 (7) | 0.0200 (8) | −0.0024 (6) | −0.0005 (6) | 0.0036 (6) |
C20 | 0.0200 (9) | 0.0209 (8) | 0.0251 (9) | −0.0084 (7) | 0.0028 (7) | 0.0036 (7) |
C21 | 0.0211 (9) | 0.0338 (10) | 0.0226 (9) | −0.0021 (8) | 0.0047 (7) | 0.0023 (7) |
C22 | 0.0165 (8) | 0.0278 (9) | 0.0256 (9) | 0.0033 (7) | 0.0034 (7) | 0.0065 (7) |
C23 | 0.0196 (9) | 0.0441 (12) | 0.0251 (9) | 0.0035 (9) | 0.0058 (7) | 0.0028 (8) |
C19 | 0.0220 (9) | 0.0317 (10) | 0.0190 (8) | −0.0077 (8) | 0.0040 (7) | −0.0035 (7) |
C18 | 0.0213 (9) | 0.0180 (8) | 0.0189 (8) | −0.0028 (7) | 0.0005 (7) | 0.0023 (6) |
Geometric parameters (Å, º) top
O5—C22 | 1.356 (2) | C9—H9 | 0.9800 |
O5—C21 | 1.440 (2) | C11—C12 | 1.539 (2) |
O1—C3 | 1.248 (2) | C11—H11 | 0.9800 |
O2—C11 | 1.428 (2) | C12—C13 | 1.533 (2) |
O2—HO2 | 0.80 (3) | C12—H12A | 0.9700 |
O3—C17 | 1.438 (2) | C12—H12B | 0.9700 |
O3—HO3 | 0.87 (3) | C13—C14 | 1.539 (2) |
O4—C20 | 1.207 (2) | C13—C18 | 1.540 (2) |
O6—C22 | 1.202 (2) | C13—C17 | 1.568 (2) |
C3—C4 | 1.447 (2) | C14—C15 | 1.543 (2) |
C3—C2 | 1.461 (2) | C14—H14A | 0.9800 |
C2—C1 | 1.335 (3) | C15—C16 | 1.556 (3) |
C2—H2 | 0.9300 | C15—H15A | 0.9700 |
C1—C10 | 1.503 (2) | C15—H15B | 0.9700 |
C1—H1 | 0.9300 | C16—C17 | 1.544 (2) |
C10—C5 | 1.511 (2) | C16—H16A | 0.9700 |
C10—C19 | 1.556 (2) | C16—H16B | 0.9700 |
C10—C9 | 1.581 (2) | C17—C20 | 1.535 (2) |
C4—C5 | 1.341 (2) | C20—C21 | 1.526 (3) |
C4—H4 | 0.9300 | C21—H21A | 0.9700 |
C5—C6 | 1.503 (2) | C21—H21B | 0.9700 |
C6—C7 | 1.532 (3) | C22—C23 | 1.496 (3) |
C6—H6A | 0.9700 | C23—H23C | 0.9600 |
C6—H6B | 0.9700 | C23—H23B | 0.9600 |
C7—C8 | 1.535 (2) | C23—H23A | 0.9600 |
C7—H7A | 0.9700 | C19—H19B | 0.9600 |
C7—H7B | 0.9700 | C19—H19C | 0.9600 |
C8—C14 | 1.527 (2) | C19—H19A | 0.9600 |
C8—C9 | 1.552 (2) | C18—H18B | 0.9600 |
C8—H8 | 0.9800 | C18—H18C | 0.9600 |
C9—C11 | 1.539 (2) | C18—H18A | 0.9600 |
| | | |
C22—O5—C21 | 114.28 (14) | C12—C13—C14 | 109.12 (13) |
C11—O2—HO2 | 107.5 (18) | C12—C13—C18 | 111.44 (13) |
C17—O3—HO3 | 107.7 (16) | C14—C13—C18 | 112.33 (14) |
O1—C3—C4 | 121.01 (15) | C12—C13—C17 | 115.23 (14) |
O1—C3—C2 | 121.36 (15) | C14—C13—C17 | 98.86 (13) |
C4—C3—C2 | 117.63 (15) | C18—C13—C17 | 109.30 (13) |
C1—C2—C3 | 120.42 (16) | C8—C14—C13 | 114.13 (13) |
C1—C2—H2 | 119.8 | C8—C14—C15 | 119.73 (15) |
C3—C2—H2 | 119.8 | C13—C14—C15 | 103.86 (14) |
C2—C1—C10 | 124.68 (16) | C8—C14—H14A | 106.0 |
C2—C1—H1 | 117.7 | C13—C14—H14A | 106.0 |
C10—C1—H1 | 117.7 | C15—C14—H14A | 106.0 |
C1—C10—C5 | 112.08 (13) | C14—C15—C16 | 103.66 (14) |
C1—C10—C19 | 107.89 (14) | C14—C15—H15A | 111.0 |
C5—C10—C19 | 107.29 (14) | C16—C15—H15A | 111.0 |
C1—C10—C9 | 107.71 (14) | C14—C15—H15B | 111.0 |
C5—C10—C9 | 106.86 (13) | C16—C15—H15B | 111.0 |
C19—C10—C9 | 115.11 (13) | H15A—C15—H15B | 109.0 |
C5—C4—C3 | 122.35 (15) | C17—C16—C15 | 106.51 (14) |
C5—C4—H4 | 118.8 | C17—C16—H16A | 110.4 |
C3—C4—H4 | 118.8 | C15—C16—H16A | 110.4 |
C4—C5—C6 | 121.42 (15) | C17—C16—H16B | 110.4 |
C4—C5—C10 | 122.58 (15) | C15—C16—H16B | 110.4 |
C6—C5—C10 | 115.94 (14) | H16A—C16—H16B | 108.6 |
C5—C6—C7 | 109.03 (14) | O3—C17—C20 | 107.33 (14) |
C5—C6—H6A | 109.9 | O3—C17—C16 | 111.84 (14) |
C7—C6—H6A | 109.9 | C20—C17—C16 | 114.60 (14) |
C5—C6—H6B | 109.9 | O3—C17—C13 | 107.84 (13) |
C7—C6—H6B | 109.9 | C20—C17—C13 | 112.63 (14) |
H6A—C6—H6B | 108.3 | C16—C17—C13 | 102.46 (14) |
C6—C7—C8 | 112.08 (14) | O4—C20—C21 | 121.23 (17) |
C6—C7—H7A | 109.2 | O4—C20—C17 | 124.00 (18) |
C8—C7—H7A | 109.2 | C21—C20—C17 | 114.77 (15) |
C6—C7—H7B | 109.2 | O5—C21—C20 | 112.93 (15) |
C8—C7—H7B | 109.2 | O5—C21—H21A | 109.0 |
H7A—C7—H7B | 107.9 | C20—C21—H21A | 109.0 |
C14—C8—C7 | 109.81 (14) | O5—C21—H21B | 109.0 |
C14—C8—C9 | 107.02 (13) | C20—C21—H21B | 109.0 |
C7—C8—C9 | 110.21 (13) | H21A—C21—H21B | 107.8 |
C14—C8—H8 | 109.9 | O6—C22—O5 | 123.10 (17) |
C7—C8—H8 | 109.9 | O6—C22—C23 | 125.84 (18) |
C9—C8—H8 | 109.9 | O5—C22—C23 | 111.05 (16) |
C11—C9—C8 | 114.05 (13) | C22—C23—H23C | 109.5 |
C11—C9—C10 | 114.34 (13) | C22—C23—H23B | 109.5 |
C8—C9—C10 | 113.19 (13) | H23C—C23—H23B | 109.5 |
C11—C9—H9 | 104.6 | C22—C23—H23A | 109.5 |
C8—C9—H9 | 104.6 | H23C—C23—H23A | 109.5 |
C10—C9—H9 | 104.6 | H23B—C23—H23A | 109.5 |
O2—C11—C12 | 112.46 (13) | C10—C19—H19B | 109.5 |
O2—C11—C9 | 108.81 (13) | C10—C19—H19C | 109.5 |
C12—C11—C9 | 112.46 (13) | H19B—C19—H19C | 109.5 |
O2—C11—H11 | 107.6 | C10—C19—H19A | 109.5 |
C12—C11—H11 | 107.6 | H19B—C19—H19A | 109.5 |
C9—C11—H11 | 107.6 | H19C—C19—H19A | 109.5 |
C13—C12—C11 | 113.42 (14) | C13—C18—H18B | 109.5 |
C13—C12—H12A | 108.9 | C13—C18—H18C | 109.5 |
C11—C12—H12A | 108.9 | H18B—C18—H18C | 109.5 |
C13—C12—H12B | 108.9 | C13—C18—H18A | 109.5 |
C11—C12—H12B | 108.9 | H18B—C18—H18A | 109.5 |
H12A—C12—H12B | 107.7 | H18C—C18—H18A | 109.5 |
| | | |
O1—C3—C2—C1 | 176.40 (17) | C11—C12—C13—C18 | −72.82 (18) |
C4—C3—C2—C1 | −3.0 (2) | C11—C12—C13—C17 | 161.91 (13) |
C3—C2—C1—C10 | 5.0 (3) | C7—C8—C14—C13 | 178.78 (13) |
C2—C1—C10—C5 | −2.1 (2) | C9—C8—C14—C13 | 59.15 (17) |
C2—C1—C10—C19 | −120.01 (19) | C7—C8—C14—C15 | −57.29 (19) |
C2—C1—C10—C9 | 115.16 (19) | C9—C8—C14—C15 | −176.92 (14) |
O1—C3—C4—C5 | 178.72 (16) | C12—C13—C14—C8 | −59.11 (18) |
C2—C3—C4—C5 | −1.9 (2) | C18—C13—C14—C8 | 65.00 (18) |
C3—C4—C5—C6 | −172.13 (15) | C17—C13—C14—C8 | −179.81 (13) |
C3—C4—C5—C10 | 4.8 (3) | C12—C13—C14—C15 | 168.80 (14) |
C1—C10—C5—C4 | −2.9 (2) | C18—C13—C14—C15 | −67.09 (17) |
C19—C10—C5—C4 | 115.39 (18) | C17—C13—C14—C15 | 48.10 (15) |
C9—C10—C5—C4 | −120.64 (17) | C8—C14—C15—C16 | −160.80 (14) |
C1—C10—C5—C6 | 174.22 (14) | C13—C14—C15—C16 | −32.06 (17) |
C19—C10—C5—C6 | −67.52 (18) | C14—C15—C16—C17 | 2.80 (18) |
C9—C10—C5—C6 | 56.44 (17) | C15—C16—C17—O3 | −88.58 (17) |
C4—C5—C6—C7 | 117.91 (18) | C15—C16—C17—C20 | 148.98 (15) |
C10—C5—C6—C7 | −59.22 (18) | C15—C16—C17—C13 | 26.67 (17) |
C5—C6—C7—C8 | 56.09 (18) | C12—C13—C17—O3 | −43.37 (18) |
C6—C7—C8—C14 | −172.45 (13) | C14—C13—C17—O3 | 72.74 (15) |
C6—C7—C8—C9 | −54.79 (18) | C18—C13—C17—O3 | −169.74 (13) |
C14—C8—C9—C11 | −53.90 (17) | C12—C13—C17—C20 | 74.87 (18) |
C7—C8—C9—C11 | −173.27 (14) | C14—C13—C17—C20 | −169.03 (14) |
C14—C8—C9—C10 | 173.08 (12) | C18—C13—C17—C20 | −51.51 (19) |
C7—C8—C9—C10 | 53.71 (17) | C12—C13—C17—C16 | −161.49 (13) |
C1—C10—C9—C11 | 53.88 (17) | C14—C13—C17—C16 | −45.39 (15) |
C5—C10—C9—C11 | 174.49 (13) | C18—C13—C17—C16 | 72.13 (16) |
C19—C10—C9—C11 | −66.49 (19) | O3—C17—C20—O4 | −154.98 (17) |
C1—C10—C9—C8 | −173.23 (13) | C16—C17—C20—O4 | −30.1 (2) |
C5—C10—C9—C8 | −52.63 (16) | C13—C17—C20—O4 | 86.5 (2) |
C19—C10—C9—C8 | 66.39 (18) | O3—C17—C20—C21 | 24.1 (2) |
C8—C9—C11—O2 | −74.93 (17) | C16—C17—C20—C21 | 148.95 (16) |
C10—C9—C11—O2 | 57.54 (17) | C13—C17—C20—C21 | −94.44 (18) |
C8—C9—C11—C12 | 50.36 (18) | C22—O5—C21—C20 | −77.2 (2) |
C10—C9—C11—C12 | −177.17 (13) | O4—C20—C21—O5 | −16.1 (3) |
O2—C11—C12—C13 | 74.46 (17) | C17—C20—C21—O5 | 164.80 (15) |
C9—C11—C12—C13 | −48.80 (18) | C21—O5—C22—O6 | 5.9 (3) |
C11—C12—C13—C14 | 51.81 (18) | C21—O5—C22—C23 | −172.58 (16) |