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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617006556/sk3652sup1.cif
Contains datablocks ELMAM2, IAM_MoPro, IAM_shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006556/sk3652IAM_shelxsup2.hkl
Contains datablock IAM_shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006556/sk3652IAM_MoProsup3.hkl
Contains datablock IAM_MoPro

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006556/sk3652ELMAM2sup4.hkl
Contains datablock ELMAM2

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617006556/sk3652sup5.pdf
Topological parameters of the strong hydrogen bonds

CCDC references: 1547360; 1547359; 1547358

Computing details top

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-[(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 (ELMAM2) top
Crystal data top
C23H30O6F(000) = 432
Mr = 402.46Dx = 1.303 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 1200 reflections
a = 8.4816 (1) Åθ = 5.1–72.2°
b = 13.865 (3) ŵ = 0.76 mm1
c = 8.9437 (1) ÅT = 100 K
β = 102.709 (1)°Block, colorless
V = 1026.0 (2) Å30.43 × 0.34 × 0.21 mm
Z = 2
Data collection top
Bruker Kappa APEXII CMOS detector
diffractometer
4018 independent reflections
Radiation source: Microfocus3976 reflections with > 2.0σ(I)
Graphite monochromatorRint = 0.028
ω and φ scanθmax = 72.2°, θmin = 5.1°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 010
Tmin = 0.735, Tmax = 0.856k = 1717
16242 measured reflectionsl = 1110
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.018H 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 reflectionsΔρmax = 0.11 e Å3
262 parametersΔρmin = 0.14 e Å3
0 restraintsAbsolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
O50.70274 (8)0.6266 (2)0.22895 (7)0.02560 (7)
O10.18968 (7)0.3601 (2)1.26199 (6)0.01831 (7)
O20.12075 (8)0.4751 (2)0.49923 (7)0.02034 (7)
O30.62449 (7)0.7004 (2)0.65025 (6)0.01935 (7)
O40.48420 (9)0.7664 (2)0.26468 (7)0.02775 (8)
O60.48211 (8)0.5327 (2)0.20364 (8)0.02625 (7)
C30.15950 (10)0.3957 (2)1.13056 (9)0.01413 (8)
C20.19306 (11)0.3429 (2)0.99978 (10)0.01738 (9)
H20.252440.273331.016920.03693
C10.15160 (11)0.3802 (2)0.85832 (10)0.01736 (9)
H10.170090.336410.763350.03530
C100.08137 (10)0.4792 (2)0.82179 (9)0.01449 (9)
C40.08747 (10)0.4907 (2)1.10259 (9)0.01434 (8)
H40.059080.529771.198180.03176
C50.05640 (9)0.5314 (2)0.96281 (9)0.01396 (8)
C60.00186 (11)0.6342 (2)0.94013 (9)0.01775 (9)
H6A0.011270.665771.048620.03472
H6B0.115100.638590.859560.03544
C70.12760 (11)0.6920 (2)0.87742 (9)0.01830 (9)
H7A0.241660.693270.962620.03302
H7B0.086100.766140.853960.03629
C80.15900 (10)0.6479 (2)0.72921 (9)0.01447 (9)
H80.049370.654260.637660.03016
C90.20722 (10)0.5404 (2)0.75477 (8)0.01321 (8)
H90.317150.540810.846680.02710
C110.26000 (10)0.4929 (2)0.61779 (9)0.01494 (9)
H110.315430.423170.657110.03358
C120.38872 (10)0.5527 (2)0.56167 (9)0.01551 (8)
H12A0.503310.545890.645230.03282
H12B0.405960.521710.454160.03400
C130.34482 (10)0.6595 (2)0.53767 (9)0.01444 (8)
C140.30050 (10)0.6997 (2)0.68381 (9)0.01511 (9)
H14A0.405660.686900.778160.02935
C150.29384 (12)0.8094 (2)0.65822 (10)0.02021 (10)
H15A0.323430.848140.767140.03954
H15B0.174040.831540.595160.03932
C160.42260 (11)0.8282 (2)0.56167 (10)0.01997 (9)
H16A0.366990.863720.453960.04149
H16B0.519730.872940.627000.04228
C170.48963 (10)0.7281 (2)0.53083 (9)0.01705 (9)
C200.54379 (11)0.7207 (2)0.37846 (10)0.01988 (9)
C210.68346 (11)0.6506 (2)0.37939 (10)0.02396 (10)
H21A0.795930.682800.442690.04096
H21B0.660520.583890.435960.03750
C220.59418 (11)0.5616 (2)0.15387 (10)0.02108 (9)
C230.63519 (11)0.5306 (2)0.00648 (10)0.02805 (10)
H23C0.555340.473130.043300.05238
H23B0.759490.507670.029370.05341
H23A0.620220.591180.070800.05162
C190.08754 (11)0.4672 (2)0.71237 (10)0.02251 (9)
H19B0.077360.424160.614700.04243
H19C0.134500.537200.673630.04123
H19A0.169630.434160.773420.04272
C180.20904 (11)0.6751 (2)0.39418 (9)0.01826 (9)
H18B0.247830.645600.296790.04105
H18C0.187790.751380.378780.04239
H18A0.101960.638770.410820.04039
HO20.154100.438970.422800.03227
HO30.696210.757010.683420.03495
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0176 (3)0.0355 (3)0.0249 (3)0.0051 (3)0.0073 (2)0.0017 (3)
O10.0219 (3)0.0171 (3)0.0149 (3)0.0033 (2)0.0019 (2)0.0025 (2)
O20.0243 (3)0.0213 (3)0.0163 (3)0.0079 (2)0.0064 (2)0.0059 (2)
O30.0185 (3)0.0155 (3)0.0207 (3)0.0018 (2)0.0029 (2)0.0020 (2)
O40.0329 (4)0.0257 (3)0.0242 (3)0.0007 (3)0.0055 (3)0.0111 (3)
O60.0216 (3)0.0301 (3)0.0293 (3)0.0040 (3)0.0107 (3)0.0015 (3)
C30.0147 (4)0.0128 (3)0.0143 (4)0.0006 (3)0.0020 (3)0.0008 (3)
C20.0238 (4)0.0108 (3)0.0198 (4)0.0015 (3)0.0097 (3)0.0002 (3)
H20.051980.020290.040670.006000.014860.00177
C10.0272 (4)0.0093 (3)0.0178 (4)0.0019 (3)0.0098 (3)0.0020 (3)
H10.051270.025680.031450.001830.014530.00820
C100.0190 (4)0.0121 (3)0.0126 (3)0.0012 (3)0.0039 (3)0.0013 (3)
C40.0163 (4)0.0132 (4)0.0130 (3)0.0029 (3)0.0023 (3)0.0011 (3)
H40.037020.033720.024410.007080.006470.00476
C50.0153 (4)0.0124 (4)0.0140 (3)0.0015 (3)0.0029 (3)0.0016 (3)
C60.0214 (4)0.0139 (4)0.0182 (4)0.0058 (3)0.0049 (3)0.0008 (3)
H6A0.043090.035230.025830.006400.007550.00554
H6B0.027660.042920.031000.004960.003830.00265
C70.0233 (4)0.0120 (3)0.0198 (4)0.0034 (3)0.0050 (3)0.0009 (3)
H7A0.029800.035300.030050.002360.001860.00186
H7B0.045880.023140.039650.012580.009010.00325
C80.0170 (4)0.0102 (3)0.0154 (4)0.0018 (3)0.0017 (3)0.0007 (3)
H80.026960.033390.026880.003180.001140.00091
C90.0169 (4)0.0095 (3)0.0130 (3)0.0004 (3)0.0028 (3)0.0001 (3)
H90.025390.025170.027920.000110.000270.00141
C110.0205 (4)0.0095 (3)0.0159 (3)0.0013 (3)0.0062 (3)0.0006 (3)
H110.039510.021420.041800.003150.013230.00261
C120.0187 (4)0.0112 (3)0.0173 (3)0.0012 (3)0.0055 (3)0.0009 (3)
H12A0.028190.030690.036220.001020.000170.00353
H12B0.043240.030910.030470.002790.013740.00487
C130.0163 (4)0.0108 (3)0.0151 (4)0.0020 (3)0.0008 (3)0.0014 (3)
C140.0174 (4)0.0103 (3)0.0163 (3)0.0002 (3)0.0008 (3)0.0007 (3)
H14A0.028840.025310.030150.000590.001590.00128
C150.0254 (5)0.0107 (4)0.0234 (4)0.0006 (3)0.0027 (3)0.0008 (3)
H15A0.055450.025640.035610.003410.005900.00391
H15B0.038580.032780.043330.007350.001890.00943
C160.0217 (4)0.0114 (4)0.0247 (4)0.0024 (3)0.0005 (3)0.0033 (3)
H16A0.049790.034790.037630.004870.004730.01207
H16B0.045620.030610.047570.011120.003690.00302
C170.0183 (4)0.0134 (3)0.0173 (4)0.0016 (3)0.0009 (3)0.0032 (3)
C200.0188 (4)0.0196 (4)0.0207 (4)0.0039 (3)0.0031 (3)0.0057 (3)
C210.0184 (4)0.0300 (4)0.0231 (4)0.0015 (4)0.0040 (3)0.0024 (3)
H21A0.028120.050580.041960.009020.002910.00112
H21B0.040080.034130.040700.001140.014120.00877
C220.0142 (4)0.0267 (4)0.0224 (4)0.0007 (3)0.0041 (3)0.0038 (3)
C230.0185 (4)0.0440 (6)0.0224 (4)0.0032 (4)0.0063 (3)0.0017 (4)
H23C0.050690.064680.046090.015140.019990.01164
H23B0.034900.082380.045030.011230.013240.00177
H23A0.057150.061310.039860.003430.018130.01233
C190.0196 (4)0.0304 (5)0.0169 (4)0.0076 (4)0.0026 (3)0.0042 (3)
H19B0.041890.053780.031780.006770.008430.01835
H19C0.038060.038050.042720.000320.001640.00271
H19A0.035680.061690.031880.016370.009750.00370
C180.0192 (4)0.0166 (4)0.0168 (4)0.0029 (3)0.0009 (3)0.0024 (3)
H18B0.039180.054330.030310.005920.009120.00427
H18C0.048610.027970.045520.004510.000610.00605
H18A0.029790.051420.039210.009690.005950.00817
HO20.035550.034180.028700.005610.010530.00989
HO30.034210.028420.038760.010770.000560.00348
Geometric parameters (Å, º) top
O5—C221.3561 (5)C9—H91.0990
O5—C211.4299 (4)C11—C121.5399 (4)
O1—C31.2484 (4)C11—H111.0990
O2—C111.4246 (4)C12—C131.5310 (5)
O2—HO20.9399C12—H12B1.0920
O3—C171.4349 (3)C12—H12A1.0920
O3—HO30.9971C13—C171.5651 (4)
O4—C201.2108 (5)C13—C141.5413 (4)
O6—C221.2036 (5)C13—C181.5393 (3)
C3—C41.4510 (5)C14—C151.5379 (5)
C3—C21.4598 (4)C14—H14A1.0990
C2—C11.3401 (5)C15—C161.5561 (4)
C2—H21.0830C15—H15A1.0920
C1—C101.5032 (5)C15—H15B1.0920
C1—H11.0830C16—C171.5478 (5)
C10—C91.5817 (4)C16—H16B1.0920
C10—C51.5089 (4)C16—H16A1.0920
C10—C191.5558 (4)C17—C201.5343 (4)
C4—C51.3436 (4)C20—C211.5308 (5)
C4—H41.0830C21—H21A1.0920
C5—C61.4997 (5)C21—H21B1.0920
C6—C71.5349 (4)C22—C231.4983 (4)
C6—H6A1.0920C23—H23C1.0770
C6—H6B1.0920C23—H23A1.0770
C7—C81.5355 (4)C23—H23B1.0770
C7—H7B1.0920C19—H19A1.0770
C7—H7A1.0920C19—H19C1.0770
C8—C141.5284 (4)C19—H19B1.0770
C8—C91.5484 (5)C18—H18C1.0770
C8—H81.0990C18—H18A1.0770
C9—C111.5414 (4)C18—H18B1.0770
C22—O5—C21114.5 (3)C12—C11—H11107.085
C11—O2—HO2107.519C13—C12—H12B109.434
C17—O3—HO3110.198C13—C12—H12A109.384
C4—C3—C2117.8 (3)H12B—C12—H12A107.287
C1—C2—H2119.635C17—C13—C1498.8 (2)
C10—C1—C2124.5 (3)C17—C13—C12115.1 (3)
C10—C1—H1117.383C17—C13—C18109.4 (2)
C9—C10—C5106.8 (2)C14—C13—C12109.1 (3)
C9—C10—C1107.7 (3)C14—C13—C18112.3 (3)
C9—C10—C19115.1 (3)C15—C14—H14A105.719
C5—C10—C1112.2 (3)C16—C15—H15A111.167
C5—C10—C19107.3 (3)C16—C15—H15B110.684
C5—C4—H4119.510H15A—C15—H15B109.143
C6—C5—C4121.1 (3)C17—C16—C15106.2 (3)
C7—C6—H6A109.319C17—C16—H16B109.934
C7—C6—H6B109.486C17—C16—H16A110.559
H6A—C6—H6B107.990H16B—C16—H16A110.177
C8—C7—C6112.0 (3)C20—C17—C13112.6 (3)
C8—C7—H7B108.601C20—C17—C16114.3 (3)
C8—C7—H7A108.275H21A—C21—H21B109.303
H7B—C7—H7A108.507H23C—C23—H23A109.703
C14—C8—C9107.1 (2)H23C—C23—H23B111.095
C14—C8—C7109.7 (3)H23A—C23—H23B108.944
C14—C8—H8110.443H19A—C19—H19C108.168
C9—C8—C7110.3 (2)H19A—C19—H19B110.592
C9—C8—H8109.899H19C—C19—H19B109.165
C11—C9—C10114.2 (2)H18C—C18—H18A110.751
C11—C9—C8114.0 (2)H18C—C18—H18B109.978
C11—C9—H9104.455H18A—C18—H18B110.566
O5—C22—C23—H23C173.34H7B—C7—C8—C9176.24
O5—C22—C23—H23A66.87H7B—C7—C8—H855.28
O5—C22—C23—H23B51.83C8—C14—C13—C17179.54 (6)
O5—C21—C20—O415.92 (7)C8—C14—C13—C1258.96 (6)
O5—C21—C20—C17164.73 (6)C8—C14—C13—C1865.20 (6)
O1—C3—C4—C5178.81 (2)C8—C14—C15—C16160.75 (6)
O1—C3—C4—H40.75C8—C14—C15—H15A79.61
O1—C3—C2—C1176.32 (5)C8—C14—C15—H15B41.85
O1—C3—C2—H24.04C8—C9—C11—C1250.52 (6)
O2—C11—C9—C1057.45 (6)C8—C9—C11—H11168.06
O2—C11—C9—C874.89 (6)C8—C9—C10—C1966.33 (6)
O2—C11—C9—H9171.06H8—C8—C14—C1360.54
O2—C11—C12—C1374.63 (6)H8—C8—C14—C1563.48
O2—C11—C12—H12B47.22H8—C8—C14—H14A177.31
O2—C11—C12—H12A163.52H8—C8—C9—C1165.94
O3—C17—C20—O4154.84 (14)H8—C8—C9—H9179.67
O3—C17—C20—C2124.50 (8)C9—C11—O2—HO2172.65
O3—C17—C13—C1472.68 (6)C9—C11—C12—C1348.94 (6)
O3—C17—C13—C1243.37 (7)C9—C11—C12—H12B170.80
O3—C17—C13—C18169.83 (6)C9—C11—C12—H12A72.91
O3—C17—C16—C1588.74 (6)C9—C10—C19—H19A171.47
O3—C17—C16—H16B29.86C9—C10—C19—H19C53.10
O3—C17—C16—H16A151.72C9—C10—C19—H19B66.74
O4—C20—C17—C1386.19 (7)C9—C8—C14—C1359.12 (6)
O4—C20—C17—C1630.24 (8)C9—C8—C14—C15176.87 (6)
O4—C20—C21—H21A104.83C9—C8—C14—H14A57.65
O4—C20—C21—H21B135.86H9—C9—C11—C1263.53
O6—C22—O5—C216.21 (6)H9—C9—C11—H1154.01
O6—C22—C23—H23C5.43H9—C9—C10—C19179.93
O6—C22—C23—H23A114.36H9—C9—C8—C1459.66
O6—C22—C23—H23B126.94C11—C9—C10—C1966.38 (6)
C3—C4—C5—C104.86 (5)C11—C9—C8—C1454.06 (6)
C3—C4—C5—C6172.10 (6)C11—C12—C13—C17161.87 (6)
C3—C2—C1—C104.89 (5)C11—C12—C13—C1451.86 (6)
C3—C2—C1—H1175.33C11—C12—C13—C1872.76 (6)
C2—C3—C4—C52.05 (6)H11—C11—O2—HO256.03
C2—C3—C4—H4178.39H11—C11—C12—C13166.70
C2—C1—C10—C9115.16 (8)H11—C11—C12—H12B71.44
C2—C1—C10—C52.16 (6)H11—C11—C12—H12A44.86
C2—C1—C10—C19120.11 (8)C12—C11—O2—HO262.00
H2—C2—C3—C4176.82C12—C13—C17—C2075.09 (6)
H2—C2—C1—C10174.74C12—C13—C17—C16161.59 (6)
H2—C2—C1—H15.04C12—C13—C14—C15168.73 (7)
C1—C10—C9—C1153.85 (6)C12—C13—C14—H14A57.37
C1—C10—C9—C8173.43 (6)C12—C13—C18—H18C176.66
C1—C10—C9—H959.70C12—C13—C18—H18A62.90
C1—C10—C5—C6174.28 (6)C12—C13—C18—H18B57.25
C1—C10—C5—C42.82 (5)H12A—C12—C13—C1740.48
C1—C10—C19—H19A68.33H12A—C12—C13—C1469.54
C1—C10—C19—H19C173.31H12A—C12—C13—C18165.84
C1—C10—C19—H19B53.46H12B—C12—C13—C1776.79
C1—C2—C3—C42.82 (6)H12B—C12—C13—C14173.19
H1—C1—C10—C964.62H12B—C12—C13—C1848.57
H1—C1—C10—C5178.06C13—C17—O3—HO3152.55
H1—C1—C10—C1960.11C13—C17—C20—C2194.48 (7)
C10—C9—C11—C12177.14 (5)C13—C17—C16—C1526.90 (10)
C10—C9—C11—H1159.60C13—C17—C16—H16B145.50
C10—C9—C8—C14173.13 (5)C13—C17—C16—H16A92.64
C10—C9—C8—C753.79 (6)C13—C14—C15—C1631.96 (9)
C10—C9—C8—H866.87C13—C14—C15—H15A151.60
C10—C5—C6—C759.15 (6)C13—C14—C15—H15B86.94
C10—C5—C6—H6A179.32C14—C13—C17—C20168.85 (6)
C10—C5—C6—H6B61.27C14—C13—C17—C1645.53 (8)
C10—C5—C4—H4175.59C14—C13—C18—H18C60.50
C4—C5—C10—C9120.67 (8)C14—C13—C18—H18A59.94
C4—C5—C10—C19115.40 (7)C14—C13—C18—H18B179.92
C4—C5—C6—C7118.01 (8)C14—C15—C16—C172.66 (6)
C4—C5—C6—H6A2.17C14—C15—C16—H16B116.10
C4—C5—C6—H6B121.58C14—C15—C16—H16A122.42
H4—C4—C5—C67.46H14A—C14—C13—C1763.21
C5—C10—C9—C11174.60 (6)H14A—C14—C13—C18178.47
C5—C10—C9—C852.68 (6)H14A—C14—C15—C1680.00
C5—C10—C9—H961.06H14A—C14—C15—H15A39.65
C5—C10—C19—H19A52.72H14A—C14—C15—H15B161.10
C5—C10—C19—H19C65.64C15—C14—C13—C1748.15 (8)
C5—C10—C19—H19B174.51C15—C14—C13—C1867.11 (6)
C5—C6—C7—C855.89 (7)C15—C16—C17—C20149.07 (13)
C5—C6—C7—H7B176.68H15A—C15—C16—C17122.25
C5—C6—C7—H7A64.21H15A—C15—C16—H16B3.49
C6—C5—C10—C956.43 (6)H15A—C15—C16—H16A117.99
C6—C5—C10—C1967.50 (7)H15B—C15—C16—C17116.28
C6—C7—C8—C14172.41 (6)H15B—C15—C16—H16B124.97
C6—C7—C8—C954.68 (7)H15B—C15—C16—H16A3.49
C6—C7—C8—H866.28C16—C17—O3—HO340.47
H6A—C6—C7—C8176.75C16—C17—C20—C21149.09 (14)
H6A—C6—C7—H7B62.45C16—C17—C13—C1871.95 (6)
H6A—C6—C7—H7A56.65H16A—C16—C17—C2029.53
H6B—C6—C7—C865.14H16B—C16—C17—C2092.33
H6B—C6—C7—H7B55.66C17—C20—C21—H21A74.53
H6B—C6—C7—H7A174.77C17—C20—C21—H21B44.79
C7—C8—C14—C13178.79 (6)C17—C13—C18—H18C48.17
C7—C8—C14—C1557.19 (6)C17—C13—C18—H18A168.61
C7—C8—C14—H14A62.03C17—C13—C18—H18B71.24
C7—C8—C9—C11173.40 (6)C20—C17—O3—HO385.65
C7—C8—C9—H959.67C20—C17—C13—C1851.37 (7)
H7A—C7—C8—C1451.61C20—C21—O5—C2277.36 (7)
H7A—C7—C8—C966.12C21—O5—C22—C23172.60 (6)
H7A—C7—C8—H8172.92H21A—C21—O5—C22161.38
H7B—C7—C8—C1466.02H21B—C21—O5—C2243.11
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO2···O1i0.941.882.8168 (4)172
O2—HO2···C3i0.942.693.5595 (3)154
O2—HO2···C4i0.942.893.5029 (1)124
C12—H12A···O31.092.372.8504 (5)105
C12—H12B···O61.092.473.4749 (2)153
C14—H14A···O31.102.392.8292 (2)102
C16—H16A···O41.092.532.9453 (3)101
C21—H21B···C121.092.813.5415 (3)124
C19—H19B···O21.082.272.8720 (2)113
C19—H19C···C81.082.873.2452 (6)100
C18—H18B···O41.082.683.0950 (3)103
C18—H18C···C161.082.522.9733 (5)104
C18—H18A···O21.082.403.0726 (6)119
C6—H6A···C2ii1.092.883.4322 (6)111
C7—H7B···O1ii1.092.683.5707 (6)139
C23—H23B···C6iii1.082.943.5917 (4)119
C16—H16B···O6iv1.092.693.5139 (7)132
C16—H16B···O1v1.092.453.3487 (2)138
O3—HO3···O1v1.001.732.7302 (5)176
O3—HO3···C3v1.002.663.5981 (6)157
Symmetry codes: (i) x, y, z1; (ii) x, y+1/2, z+2; (iii) x+1, y, z1; (iv) x+1, y+1/2, z+1; (v) x+1, y+1/2, z+2.
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 (IAM_MoPro) top
Crystal data top
C23H30O6F(000) = 432
Mr = 402.46Dx = 1.303 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 1200 reflections
a = 8.4816 (1) Åθ = 5.1–72.2°
b = 13.865 (3) ŵ = 0.76 mm1
c = 8.9437 (1) ÅT = 100 K
β = 102.709 (1)°Block, colorless
V = 1026.0 (2) Å30.43 × 0.34 × 0.21 mm
Z = 2
Data collection top
Bruker Kappa APEXII CMOS detector
diffractometer
4018 independent reflections
Radiation source: Microfocus3976 reflections with > 2.0σ(I)
Graphite monochromatorRint = 0.028
ω and φ scanθmax = 72.2°, θmin = 5.1°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 010
Tmin = 0.735, Tmax = 0.856k = 1717
16242 measured reflectionsl = 1110
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034H 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 reflectionsΔρmax = 0.32 e Å3
262 parametersΔρmin = 0.20 e Å3
0 restraintsAbsolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
O50.70285 (15)0.5436 (5)0.22837 (14)0.02781 (14)
O10.18957 (14)0.2770 (5)1.26180 (12)0.02061 (13)
O20.12052 (15)0.3921 (5)0.49937 (13)0.02263 (13)
O30.62454 (15)0.6172 (5)0.65032 (13)0.02178 (13)
O40.48441 (17)0.6832 (5)0.26473 (14)0.03055 (16)
O60.48240 (15)0.4497 (5)0.20392 (15)0.02839 (14)
C30.15919 (19)0.3126 (5)1.13043 (18)0.01676 (16)
C20.1933 (2)0.2601 (5)0.99959 (19)0.01954 (18)
H20.252360.190471.016470.03693
C10.1513 (2)0.2971 (5)0.85822 (19)0.01965 (18)
H10.169830.252700.763910.03530
C100.0814 (2)0.3961 (5)0.82184 (17)0.01678 (17)
C40.08768 (19)0.4076 (5)1.10265 (17)0.01696 (16)
H40.058440.447221.197320.03176
C50.05622 (18)0.4486 (5)0.96283 (17)0.01616 (16)
C60.0018 (2)0.5517 (5)0.94003 (19)0.01976 (18)
H6A0.011480.582791.048800.03472
H6B0.115300.555560.859550.03544
C70.1279 (2)0.6092 (5)0.87760 (18)0.02004 (18)
H7A0.241350.610910.963630.03302
H7B0.085780.683290.854890.03629
C80.1590 (2)0.5650 (5)0.72924 (17)0.01642 (17)
H80.050070.571650.637010.03016
C90.20712 (19)0.4573 (5)0.75471 (16)0.01531 (16)
H90.316830.458140.846860.02710
C110.2601 (2)0.4098 (5)0.61796 (17)0.01689 (17)
H110.314460.339640.656710.03358
C120.3890 (2)0.4695 (5)0.56173 (18)0.01810 (17)
H12A0.503720.463350.645240.03282
H12B0.405670.439210.453600.03400
C130.34491 (19)0.5765 (5)0.53786 (17)0.01627 (17)
C140.3005 (2)0.6167 (5)0.68350 (17)0.01700 (17)
H14A0.406190.603750.777190.02935
C150.2936 (2)0.7267 (5)0.65801 (19)0.0224 (2)
H15A0.324150.765060.767180.03954
H15B0.173740.749110.595690.03932
C160.4223 (2)0.7453 (5)0.5617 (2)0.02252 (19)
H16A0.367780.780800.453730.04149
H16B0.519690.790680.624980.04228
C170.4893 (2)0.6453 (5)0.53060 (18)0.01921 (18)
C200.5435 (2)0.6376 (5)0.37827 (19)0.02246 (18)
C210.6836 (2)0.5676 (5)0.3800 (2)0.02617 (19)
H21A0.795460.600150.444050.04096
H21B0.662460.501570.439130.03750
C220.5939 (2)0.4787 (5)0.1539 (2)0.02372 (18)
C230.6349 (2)0.4476 (5)0.0063 (2)0.0307 (2)
H23C0.555250.389820.042610.05238
H23B0.759110.424340.029950.05341
H23A0.619940.508260.070780.05162
C190.0879 (2)0.3843 (5)0.71228 (19)0.02513 (19)
H19B0.077060.340780.615310.04243
H19C0.134690.454190.672670.04123
H19A0.169320.350250.773020.04272
C180.2090 (2)0.5921 (5)0.39441 (18)0.02053 (18)
H18B0.246060.562790.296030.04105
H18C0.186350.668200.377420.04239
H18A0.101100.555990.409300.04039
HO20.149750.360370.432790.03227
HO30.683600.664660.675610.03495
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0213 (6)0.0375 (7)0.0263 (6)0.0045 (5)0.0088 (5)0.0020 (5)
O10.0228 (6)0.0200 (5)0.0177 (5)0.0020 (4)0.0016 (4)0.0016 (4)
O20.0267 (6)0.0246 (6)0.0172 (5)0.0077 (5)0.0061 (5)0.0066 (4)
O30.0212 (6)0.0170 (5)0.0235 (5)0.0026 (4)0.0032 (4)0.0018 (4)
O40.0360 (8)0.0275 (6)0.0272 (6)0.0024 (6)0.0048 (5)0.0112 (5)
O60.0223 (6)0.0321 (7)0.0327 (6)0.0022 (5)0.0101 (5)0.0036 (5)
C30.0144 (7)0.0175 (7)0.0176 (7)0.0024 (6)0.0017 (5)0.0007 (5)
C20.0231 (8)0.0130 (7)0.0240 (8)0.0015 (6)0.0086 (6)0.0006 (6)
H20.051980.020290.040670.006000.014860.00177
C10.0271 (9)0.0129 (7)0.0216 (7)0.0037 (6)0.0110 (6)0.0026 (6)
H10.051270.025680.031450.001830.014530.00820
C100.0205 (8)0.0143 (7)0.0153 (7)0.0023 (6)0.0035 (6)0.0010 (5)
C40.0150 (7)0.0191 (7)0.0160 (7)0.0008 (6)0.0017 (5)0.0023 (6)
H40.037020.033720.024410.007080.006470.00476
C50.0147 (7)0.0159 (7)0.0176 (7)0.0001 (6)0.0028 (5)0.0017 (5)
C60.0226 (8)0.0166 (7)0.0211 (7)0.0045 (6)0.0070 (6)0.0002 (6)
H6A0.043090.035230.025830.006400.007550.00554
H6B0.027660.042920.031000.004960.003830.00265
C70.0254 (9)0.0133 (7)0.0220 (7)0.0029 (6)0.0067 (6)0.0006 (6)
H7A0.029800.035300.030050.002360.001860.00186
H7B0.045880.023140.039650.012580.009010.00325
C80.0185 (7)0.0127 (6)0.0174 (7)0.0024 (6)0.0027 (6)0.0009 (5)
H80.026960.033390.026880.003180.001140.00091
C90.0189 (7)0.0127 (7)0.0143 (7)0.0004 (6)0.0036 (5)0.0010 (5)
H90.025390.025170.027920.000110.000270.00141
C110.0220 (8)0.0125 (7)0.0171 (7)0.0015 (6)0.0063 (6)0.0009 (5)
H110.039510.021420.041800.003150.013230.00261
C120.0217 (8)0.0132 (7)0.0200 (7)0.0013 (6)0.0060 (6)0.0014 (5)
H12A0.028190.030690.036220.001020.000170.00353
H12B0.043240.030910.030470.002790.013740.00487
C130.0179 (7)0.0132 (7)0.0169 (7)0.0012 (6)0.0023 (6)0.0020 (5)
C140.0193 (8)0.0123 (7)0.0180 (7)0.0004 (6)0.0009 (6)0.0001 (5)
H14A0.028840.025310.030150.000590.001590.00128
C150.0283 (9)0.0126 (7)0.0253 (8)0.0005 (6)0.0034 (6)0.0003 (6)
H15A0.055450.025640.035610.003410.005900.00391
H15B0.038580.032780.043330.007350.001890.00943
C160.0256 (9)0.0125 (7)0.0274 (8)0.0017 (6)0.0013 (6)0.0031 (6)
H16A0.049790.034790.037630.004870.004730.01207
H16B0.045620.030610.047570.011120.003690.00302
C170.0201 (8)0.0142 (7)0.0211 (7)0.0020 (6)0.0004 (6)0.0033 (6)
C200.0207 (8)0.0209 (7)0.0248 (8)0.0076 (6)0.0028 (6)0.0043 (6)
C210.0211 (8)0.0355 (9)0.0219 (8)0.0012 (7)0.0048 (6)0.0012 (7)
H21A0.028120.050580.041960.009020.002910.00112
H21B0.040080.034130.040700.001140.014120.00877
C220.0163 (8)0.0282 (9)0.0259 (8)0.0030 (6)0.0031 (6)0.0057 (6)
C230.0203 (8)0.0460 (11)0.0263 (8)0.0045 (8)0.0066 (7)0.0032 (8)
H23C0.050690.064680.046090.015140.019990.01164
H23B0.034900.082380.045030.011230.013240.00177
H23A0.057150.061310.039860.003430.018130.01233
C190.0216 (9)0.0333 (9)0.0199 (7)0.0079 (7)0.0033 (6)0.0033 (6)
H19B0.041890.053780.031780.006770.008430.01835
H19C0.038060.038050.042720.000320.001640.00271
H19A0.035680.061690.031880.016370.009750.00370
C180.0214 (8)0.0195 (8)0.0182 (7)0.0030 (6)0.0009 (6)0.0024 (6)
H18B0.039180.054330.030310.005920.009120.00427
H18C0.048610.027970.045520.004510.000610.00605
H18A0.029790.051420.039210.009690.005950.00817
HO20.035550.034180.028700.005610.010530.00989
HO30.034210.028420.038760.010770.000560.00348
Geometric parameters (Å, º) top
O5—C221.3550 (9)C9—H91.0990
O5—C211.4408 (7)C11—C121.5412 (7)
O1—C31.2476 (8)C11—H111.0990
O2—C111.4266 (7)C12—C131.5333 (8)
O2—HO20.8210C12—H12B1.0920
O3—C171.4398 (7)C12—H12A1.0920
O3—HO30.8275C13—C171.5642 (7)
O4—C201.2073 (9)C13—C141.5378 (7)
O6—C221.2008 (9)C13—C181.5397 (7)
C3—C41.4489 (8)C14—C151.5410 (8)
C3—C21.4597 (7)C14—H14A1.0990
C2—C11.3379 (9)C15—C161.5535 (8)
C2—H21.0830C15—H15A1.0920
C1—C101.5029 (8)C15—H15B1.0920
C1—H11.0830C16—C171.5472 (8)
C10—C91.5812 (7)C16—H16B1.0920
C10—C51.5111 (7)C16—H16A1.0920
C10—C191.5585 (7)C17—C201.5344 (7)
C4—C51.3459 (8)C20—C211.5313 (9)
C4—H41.0830C21—H21A1.0920
C5—C61.5029 (8)C21—H21B1.0920
C6—C71.5342 (8)C22—C231.5007 (8)
C6—H6B1.0920C23—H23C1.0770
C6—H6A1.0920C23—H23A1.0770
C7—C81.5362 (7)C23—H23B1.0770
C7—H7A1.0920C19—H19B1.0770
C7—H7B1.0920C19—H19C1.0770
C8—C141.5283 (7)C19—H19A1.0770
C8—C91.5510 (7)C18—H18B1.0770
C8—H81.0990C18—H18A1.0770
C9—C111.5410 (6)C18—H18C1.0770
C22—O5—C21114.2 (6)C12—C11—H11107.488
C11—O2—HO2107.316C13—C12—H12B108.931
C17—O3—HO3108.908C13—C12—H12A108.935
C4—C3—C2117.7 (6)H12B—C12—H12A107.810
C1—C2—H2119.468C17—C13—C1498.9 (5)
C10—C1—C2124.4 (6)C17—C13—C12115.2 (5)
C10—C1—H1117.932C17—C13—C18109.2 (5)
C9—C10—C5106.8 (5)C14—C13—C12109.3 (5)
C9—C10—C1107.8 (5)C14—C13—C18112.1 (5)
C9—C10—C19115.0 (5)C15—C14—H14A105.785
C5—C10—C1112.4 (5)C16—C15—H15A110.939
C5—C10—C19107.2 (5)C16—C15—H15B111.013
C5—C4—H4118.645H15A—C15—H15B109.165
C6—C5—C4121.4 (6)C17—C16—C15106.3 (5)
C7—C6—H6B109.928C17—C16—H16B110.123
C7—C6—H6A109.654C17—C16—H16A110.236
H6B—C6—H6A108.132H16B—C16—H16A108.874
C8—C7—C6111.9 (5)C20—C17—C13112.7 (5)
C8—C7—H7A108.971C20—C17—C16114.5 (6)
C8—C7—H7B109.036H21A—C21—H21B107.970
H7A—C7—H7B108.185H23C—C23—H23A110.225
C14—C8—C9107.1 (5)H23C—C23—H23B110.861
C14—C8—C7109.8 (5)H23A—C23—H23B109.411
C14—C8—H8109.854H19B—C19—H19C109.255
C9—C8—C7110.3 (5)H19B—C19—H19A109.779
C9—C8—H8109.982H19C—C19—H19A109.250
C11—C9—C10114.3 (5)H18B—C18—H18A109.511
C11—C9—C8114.1 (5)H18B—C18—H18C109.244
C11—C9—H9104.643H18A—C18—H18C110.049
O5—C22—C23—H23C172.97H7B—C7—C8—C9175.89
O5—C22—C23—H23A66.86H7B—C7—C8—H854.54
O5—C22—C23—H23B52.12C8—C14—C13—C17179.67 (11)
O5—C21—C20—O416.11 (13)C8—C14—C13—C1258.90 (12)
O5—C21—C20—C17164.83 (12)C8—C14—C13—C1865.27 (12)
O1—C3—C4—C5178.76 (5)C8—C14—C15—C16160.94 (11)
O1—C3—C4—H41.21C8—C14—C15—H15A79.88
O1—C3—C2—C1176.13 (9)C8—C14—C15—H15B41.62
O1—C3—C2—H23.51C8—C9—C11—C1250.37 (12)
O2—C11—C9—C1057.58 (11)C8—C9—C11—H11168.54
O2—C11—C9—C874.95 (11)C8—C9—C10—C1966.34 (12)
O2—C11—C9—H9171.34H8—C8—C14—C1360.52
O2—C11—C12—C1374.57 (11)H8—C8—C14—C1563.71
O2—C11—C12—H12B46.76H8—C8—C14—H14A176.87
O2—C11—C12—H12A163.99H8—C8—C9—C1165.55
O3—C17—C20—O4154.9 (3)H8—C8—C9—H9179.29
O3—C17—C20—C2124.14 (17)C9—C11—O2—HO2172.56
O3—C17—C13—C1472.92 (12)C9—C11—C12—C1348.78 (12)
O3—C17—C13—C1243.38 (13)C9—C11—C12—H12B170.11
O3—C17—C13—C18169.78 (11)C9—C11—C12—H12A72.66
O3—C17—C16—C1588.72 (12)C9—C10—C19—H19B67.20
O3—C17—C16—H16B31.15C9—C10—C19—H19C52.63
O3—C17—C16—H16A151.30C9—C10—C19—H19A172.37
O4—C20—C17—C1386.51 (13)C9—C8—C14—C1358.91 (12)
O4—C20—C17—C1630.16 (15)C9—C8—C14—C15176.86 (12)
O4—C20—C21—H21A104.92C9—C8—C14—H14A57.44
O4—C20—C21—H21B137.36H9—C9—C11—C1263.35
O6—C22—O5—C216.07 (12)H9—C9—C11—H1154.83
O6—C22—C23—H23C5.58H9—C9—C10—C19179.61
O6—C22—C23—H23A114.59H9—C9—C8—C1459.94
O6—C22—C23—H23B126.43C11—C9—C10—C1966.59 (12)
C3—C4—C5—C104.63 (10)C11—C9—C8—C1453.80 (12)
C3—C4—C5—C6172.17 (12)C11—C12—C13—C17161.99 (11)
C3—C2—C1—C105.58 (10)C11—C12—C13—C1451.76 (13)
C3—C2—C1—H1174.82C11—C12—C13—C1872.78 (12)
C2—C3—C4—C51.57 (11)H11—C11—O2—HO256.06
C2—C3—C4—H4178.46H11—C11—C12—C13167.07
C2—C1—C10—C9114.88 (15)H11—C11—C12—H12B71.60
C2—C1—C10—C52.53 (11)H11—C11—C12—H12A45.62
C2—C1—C10—C19120.44 (16)C12—C11—O2—HO262.18
H2—C2—C3—C4176.83C12—C13—C17—C2074.82 (12)
H2—C2—C1—C10174.78C12—C13—C17—C16161.57 (12)
H2—C2—C1—H14.82C12—C13—C14—C15168.74 (13)
C1—C10—C9—C1153.64 (12)C12—C13—C14—H14A57.46
C1—C10—C9—C8173.43 (11)C12—C13—C18—H18B57.05
C1—C10—C9—H960.16C12—C13—C18—H18A62.78
C1—C10—C5—C6174.29 (12)C12—C13—C18—H18C176.57
C1—C10—C5—C42.67 (11)H12A—C12—C13—C1740.57
C1—C10—C19—H19B53.03H12A—C12—C13—C1469.66
C1—C10—C19—H19C172.86H12A—C12—C13—C18165.80
C1—C10—C19—H19A67.40H12B—C12—C13—C1776.79
C1—C2—C3—C43.53 (11)H12B—C12—C13—C14172.98
H1—C1—C10—C964.72H12B—C12—C13—C1848.44
H1—C1—C10—C5177.86C13—C17—O3—HO3153.48
H1—C1—C10—C1959.96C13—C17—C20—C2194.46 (13)
C10—C9—C11—C12177.10 (10)C13—C17—C16—C1526.7 (2)
C10—C9—C11—H1158.93C13—C17—C16—H16B146.53
C10—C9—C8—C14173.20 (11)C13—C17—C16—H16A93.32
C10—C9—C8—C753.79 (12)C13—C14—C15—C1631.92 (18)
C10—C9—C8—H867.46C13—C14—C15—H15A151.10
C10—C5—C6—C759.20 (12)C13—C14—C15—H15B87.39
C10—C5—C6—H6B61.43C14—C13—C17—C20168.89 (12)
C10—C5—C6—H6A179.48C14—C13—C17—C1645.28 (16)
C10—C5—C4—H4175.40C14—C13—C18—H18B179.97
C4—C5—C10—C9120.66 (15)C14—C13—C18—H18A60.13
C4—C5—C10—C19115.58 (14)C14—C13—C18—H18C60.52
C4—C5—C6—C7117.80 (15)C14—C15—C16—C172.74 (12)
C4—C5—C6—H6B121.57C14—C15—C16—H16B116.81
C4—C5—C6—H6A2.48C14—C15—C16—H16A122.45
H4—C4—C5—C67.80H14A—C14—C13—C1763.31
C5—C10—C9—C11174.61 (11)H14A—C14—C13—C18178.37
C5—C10—C9—C852.46 (12)H14A—C14—C15—C1679.52
C5—C10—C9—H960.81H14A—C14—C15—H15A39.66
C5—C10—C19—H19B174.23H14A—C14—C15—H15B161.16
C5—C10—C19—H19C65.95C15—C14—C13—C1747.97 (15)
C5—C10—C19—H19A53.80C15—C14—C13—C1867.09 (12)
C5—C6—C7—C856.04 (13)C15—C16—C17—C20149.0 (3)
C5—C6—C7—H7A64.82H15A—C15—C16—C17121.88
C5—C6—C7—H7B176.92H15A—C15—C16—H16B2.33
C6—C5—C10—C956.30 (12)H15A—C15—C16—H16A118.42
C6—C5—C10—C1967.46 (13)H15B—C15—C16—C17116.55
C6—C7—C8—C14172.66 (12)H15B—C15—C16—H16B123.90
C6—C7—C8—C954.87 (13)H15B—C15—C16—H16A3.15
C6—C7—C8—H866.48C16—C17—O3—HO341.45
H6A—C6—C7—C8176.57C16—C17—C20—C21148.9 (3)
H6A—C6—C7—H7A55.71C16—C17—C13—C1872.02 (12)
H6A—C6—C7—H7B62.55H16A—C16—C17—C2029.03
H6B—C6—C7—C864.68H16B—C16—C17—C2091.11
H6B—C6—C7—H7A174.46C17—C20—C21—H21A74.14
H6B—C6—C7—H7B56.20C17—C20—C21—H21B43.58
C7—C8—C14—C13178.65 (12)C17—C13—C18—H18B71.44
C7—C8—C14—C1557.11 (13)C17—C13—C18—H18A168.73
C7—C8—C14—H14A62.30C17—C13—C18—H18C48.08
C7—C8—C9—C11173.21 (12)C20—C17—O3—HO384.89
C7—C8—C9—H959.47C20—C17—C13—C1851.58 (13)
H7A—C7—C8—C1451.57C20—C21—O5—C2277.25 (13)
H7A—C7—C8—C966.22C21—O5—C22—C23172.53 (12)
H7A—C7—C8—H8172.42H21A—C21—O5—C22161.62
H7B—C7—C8—C1466.32H21B—C21—O5—C2244.04
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—HO2···O1i0.822.002.8195 (4)172
O2—HO2···C3i0.822.803.5618 (4)155
C12—H12A···O31.092.362.8488 (6)105
C12—H12B···O61.092.463.4728 (3)153
C14—H14A···O31.102.382.8288 (4)102
C16—H16A···O41.092.532.9478 (4)101
C21—H21B···C121.092.813.5384 (4)124
C19—H19B···O21.082.272.8712 (4)113
C19—H19C···C81.082.883.2475 (7)100
C18—H18B···O41.082.683.0965 (4)102
C18—H18C···C161.082.532.9719 (6)103
C18—H18A···O21.082.403.0738 (7)119
C6—H6A···C2ii1.092.883.4304 (7)111
C7—H7B···O1ii1.092.683.5697 (6)139
C16—H16B···O6iii1.092.693.5120 (7)132
C16—H16B···O1iv1.092.463.3518 (3)138
O3—HO3···O1iv0.831.912.7325 (6)177
Symmetry codes: (i) x, y, z1; (ii) x, y+1/2, z+2; (iii) x+1, y+1/2, z+1; (iv) x+1, y+1/2, z+2.
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 (IAM_shelx) top
Crystal data top
C23H30O6F(000) = 432
Mr = 402.46Dx = 1.303 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 8.4816 (19) ÅCell parameters from 1200 reflections
b = 13.865 (3) Åθ = 5.1–72.2°
c = 8.9437 (19) ŵ = 0.76 mm1
β = 102.709 (17)°T = 100 K
V = 1026.0 (4) Å3Block, colorless
Z = 20.43 × 0.34 × 0.21 mm
Data collection top
Bruker Kappa Apex II CMOS detector
diffractometer
4018 independent reflections
Radiation source: Microfocus3942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω and phi scanθmax = 72.2°, θmin = 5.1°
Absorption correction: multi-scan
SADABS (Krause et al., 2015)
h = 1010
Tmin = 0.735, Tmax = 0.856k = 1717
16242 measured reflectionsl = 1111
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.07Δρmax = 0.22 e Å3
4018 reflectionsΔρmin = 0.16 e Å3
271 parametersAbsolute structure: Flack x determined using 1846 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute 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
xyzUiso*/Ueq
O50.70295 (16)0.54102 (11)0.22842 (15)0.0275 (3)
O10.18982 (15)0.27450 (9)1.26188 (13)0.0200 (3)
O20.12030 (16)0.38966 (10)0.49946 (14)0.0220 (3)
O30.62443 (16)0.61465 (9)0.65034 (14)0.0214 (3)
O40.48451 (18)0.68073 (10)0.26480 (15)0.0296 (3)
O60.48224 (16)0.44716 (10)0.20361 (16)0.0281 (3)
C30.1594 (2)0.31013 (12)1.13048 (19)0.0165 (3)
C20.1930 (2)0.25744 (12)0.9996 (2)0.0190 (3)
H20.24360.19761.01440.023*
C10.1517 (2)0.29462 (12)0.8587 (2)0.0194 (3)
H10.16750.25660.77760.023*
C100.0814 (2)0.39354 (12)0.82181 (18)0.0165 (3)
C40.0878 (2)0.40496 (12)1.10240 (18)0.0164 (3)
H40.06260.43881.18390.020*
C50.05656 (19)0.44584 (12)0.96305 (18)0.0158 (3)
C60.0020 (2)0.54896 (12)0.9400 (2)0.0194 (3)
H6A0.00990.57641.03670.023*
H6B0.10190.55210.86840.023*
C70.1278 (2)0.60634 (12)0.87749 (19)0.0196 (3)
H7A0.22830.60810.95420.024*
H7B0.09040.67220.85780.024*
C80.1591 (2)0.56236 (12)0.72924 (18)0.0163 (3)
H80.06200.56820.64680.020*
C90.2072 (2)0.45466 (11)0.75470 (17)0.0151 (3)
H90.30510.45540.83680.018*
C110.2602 (2)0.40727 (12)0.61802 (18)0.0169 (3)
H110.30840.34460.65250.020*
C120.3888 (2)0.46692 (12)0.56175 (19)0.0176 (3)
H12A0.49080.46150.63590.021*
H12B0.40390.44000.46570.021*
C130.3448 (2)0.57391 (11)0.53781 (18)0.0163 (3)
C140.3007 (2)0.61395 (12)0.68386 (19)0.0174 (3)
H14A0.39490.60220.76740.021*
C150.2937 (2)0.72406 (12)0.6583 (2)0.0223 (4)
H15A0.32050.75830.75510.027*
H15B0.18720.74400.60280.027*
C160.4227 (2)0.74252 (12)0.5618 (2)0.0220 (4)
H16A0.37400.77430.46620.026*
H16B0.50870.78310.61800.026*
C170.4896 (2)0.64275 (12)0.53063 (19)0.0188 (4)
C200.5438 (2)0.63512 (13)0.3783 (2)0.0223 (4)
C210.6833 (2)0.56530 (15)0.3798 (2)0.0259 (4)
H21A0.78260.59410.43700.031*
H21B0.66450.50670.43240.031*
C220.5940 (2)0.47608 (14)0.1537 (2)0.0235 (4)
C230.6351 (2)0.44493 (17)0.0067 (2)0.0295 (4)
H23C0.56490.39320.03740.044*
H23B0.74530.42330.02660.044*
H23A0.62150.49830.06340.044*
C190.0876 (2)0.38162 (14)0.7126 (2)0.0243 (4)
H19B0.07790.34260.62640.036*
H19C0.12940.44390.67720.036*
H19A0.16000.35100.76670.036*
C180.2089 (2)0.58936 (12)0.39423 (19)0.0200 (4)
H18B0.24140.56320.30630.030*
H18C0.18810.65710.37930.030*
H18A0.11250.55740.40760.030*
HO20.148 (3)0.3583 (18)0.434 (3)0.030*
HO30.685 (3)0.665 (2)0.676 (3)0.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0202 (7)0.0374 (7)0.0263 (7)0.0039 (5)0.0084 (5)0.0018 (6)
O10.0226 (6)0.0192 (6)0.0171 (6)0.0020 (5)0.0019 (5)0.0019 (4)
O20.0263 (7)0.0238 (6)0.0167 (6)0.0077 (5)0.0064 (5)0.0074 (5)
O30.0199 (6)0.0164 (6)0.0238 (6)0.0024 (5)0.0038 (5)0.0016 (5)
O40.0346 (8)0.0273 (7)0.0259 (7)0.0020 (6)0.0047 (6)0.0105 (6)
O60.0228 (7)0.0320 (7)0.0318 (7)0.0024 (6)0.0106 (5)0.0031 (6)
C30.0134 (7)0.0170 (8)0.0185 (8)0.0025 (6)0.0021 (6)0.0002 (6)
C20.0229 (8)0.0111 (7)0.0247 (8)0.0001 (6)0.0089 (7)0.0005 (6)
C10.0266 (9)0.0128 (8)0.0213 (8)0.0040 (7)0.0109 (7)0.0043 (6)
C100.0209 (8)0.0142 (8)0.0145 (7)0.0020 (7)0.0039 (6)0.0008 (6)
C40.0154 (8)0.0179 (8)0.0157 (7)0.0003 (6)0.0031 (6)0.0032 (6)
C50.0132 (7)0.0155 (8)0.0184 (8)0.0003 (6)0.0029 (6)0.0024 (6)
C60.0221 (9)0.0171 (8)0.0198 (8)0.0049 (7)0.0060 (7)0.0003 (6)
C70.0239 (9)0.0131 (7)0.0218 (8)0.0032 (7)0.0052 (7)0.0010 (6)
C80.0186 (8)0.0130 (7)0.0163 (8)0.0021 (6)0.0018 (6)0.0007 (6)
C90.0179 (8)0.0125 (7)0.0143 (7)0.0005 (6)0.0021 (6)0.0004 (6)
C110.0225 (9)0.0111 (7)0.0176 (7)0.0012 (6)0.0053 (6)0.0000 (6)
C120.0203 (8)0.0142 (8)0.0189 (7)0.0010 (6)0.0058 (6)0.0014 (6)
C130.0177 (8)0.0135 (7)0.0168 (8)0.0022 (6)0.0019 (6)0.0019 (6)
C140.0200 (9)0.0126 (7)0.0179 (7)0.0003 (6)0.0005 (6)0.0004 (6)
C150.0271 (10)0.0133 (8)0.0247 (9)0.0009 (7)0.0021 (7)0.0002 (6)
C160.0241 (9)0.0126 (8)0.0263 (9)0.0024 (7)0.0005 (7)0.0032 (6)
C170.0194 (9)0.0147 (7)0.0200 (8)0.0024 (6)0.0005 (6)0.0036 (6)
C200.0200 (9)0.0209 (8)0.0251 (9)0.0084 (7)0.0028 (7)0.0036 (7)
C210.0211 (9)0.0338 (10)0.0226 (9)0.0021 (8)0.0047 (7)0.0023 (7)
C220.0165 (8)0.0278 (9)0.0256 (9)0.0033 (7)0.0034 (7)0.0065 (7)
C230.0196 (9)0.0441 (12)0.0251 (9)0.0035 (9)0.0058 (7)0.0028 (8)
C190.0220 (9)0.0317 (10)0.0190 (8)0.0077 (8)0.0040 (7)0.0035 (7)
C180.0213 (9)0.0180 (8)0.0189 (8)0.0028 (7)0.0005 (7)0.0023 (6)
Geometric parameters (Å, º) top
O5—C221.356 (2)C9—H90.9800
O5—C211.440 (2)C11—C121.539 (2)
O1—C31.248 (2)C11—H110.9800
O2—C111.428 (2)C12—C131.533 (2)
O2—HO20.80 (3)C12—H12A0.9700
O3—C171.438 (2)C12—H12B0.9700
O3—HO30.87 (3)C13—C141.539 (2)
O4—C201.207 (2)C13—C181.540 (2)
O6—C221.202 (2)C13—C171.568 (2)
C3—C41.447 (2)C14—C151.543 (2)
C3—C21.461 (2)C14—H14A0.9800
C2—C11.335 (3)C15—C161.556 (3)
C2—H20.9300C15—H15A0.9700
C1—C101.503 (2)C15—H15B0.9700
C1—H10.9300C16—C171.544 (2)
C10—C51.511 (2)C16—H16A0.9700
C10—C191.556 (2)C16—H16B0.9700
C10—C91.581 (2)C17—C201.535 (2)
C4—C51.341 (2)C20—C211.526 (3)
C4—H40.9300C21—H21A0.9700
C5—C61.503 (2)C21—H21B0.9700
C6—C71.532 (3)C22—C231.496 (3)
C6—H6A0.9700C23—H23C0.9600
C6—H6B0.9700C23—H23B0.9600
C7—C81.535 (2)C23—H23A0.9600
C7—H7A0.9700C19—H19B0.9600
C7—H7B0.9700C19—H19C0.9600
C8—C141.527 (2)C19—H19A0.9600
C8—C91.552 (2)C18—H18B0.9600
C8—H80.9800C18—H18C0.9600
C9—C111.539 (2)C18—H18A0.9600
C22—O5—C21114.28 (14)C12—C13—C14109.12 (13)
C11—O2—HO2107.5 (18)C12—C13—C18111.44 (13)
C17—O3—HO3107.7 (16)C14—C13—C18112.33 (14)
O1—C3—C4121.01 (15)C12—C13—C17115.23 (14)
O1—C3—C2121.36 (15)C14—C13—C1798.86 (13)
C4—C3—C2117.63 (15)C18—C13—C17109.30 (13)
C1—C2—C3120.42 (16)C8—C14—C13114.13 (13)
C1—C2—H2119.8C8—C14—C15119.73 (15)
C3—C2—H2119.8C13—C14—C15103.86 (14)
C2—C1—C10124.68 (16)C8—C14—H14A106.0
C2—C1—H1117.7C13—C14—H14A106.0
C10—C1—H1117.7C15—C14—H14A106.0
C1—C10—C5112.08 (13)C14—C15—C16103.66 (14)
C1—C10—C19107.89 (14)C14—C15—H15A111.0
C5—C10—C19107.29 (14)C16—C15—H15A111.0
C1—C10—C9107.71 (14)C14—C15—H15B111.0
C5—C10—C9106.86 (13)C16—C15—H15B111.0
C19—C10—C9115.11 (13)H15A—C15—H15B109.0
C5—C4—C3122.35 (15)C17—C16—C15106.51 (14)
C5—C4—H4118.8C17—C16—H16A110.4
C3—C4—H4118.8C15—C16—H16A110.4
C4—C5—C6121.42 (15)C17—C16—H16B110.4
C4—C5—C10122.58 (15)C15—C16—H16B110.4
C6—C5—C10115.94 (14)H16A—C16—H16B108.6
C5—C6—C7109.03 (14)O3—C17—C20107.33 (14)
C5—C6—H6A109.9O3—C17—C16111.84 (14)
C7—C6—H6A109.9C20—C17—C16114.60 (14)
C5—C6—H6B109.9O3—C17—C13107.84 (13)
C7—C6—H6B109.9C20—C17—C13112.63 (14)
H6A—C6—H6B108.3C16—C17—C13102.46 (14)
C6—C7—C8112.08 (14)O4—C20—C21121.23 (17)
C6—C7—H7A109.2O4—C20—C17124.00 (18)
C8—C7—H7A109.2C21—C20—C17114.77 (15)
C6—C7—H7B109.2O5—C21—C20112.93 (15)
C8—C7—H7B109.2O5—C21—H21A109.0
H7A—C7—H7B107.9C20—C21—H21A109.0
C14—C8—C7109.81 (14)O5—C21—H21B109.0
C14—C8—C9107.02 (13)C20—C21—H21B109.0
C7—C8—C9110.21 (13)H21A—C21—H21B107.8
C14—C8—H8109.9O6—C22—O5123.10 (17)
C7—C8—H8109.9O6—C22—C23125.84 (18)
C9—C8—H8109.9O5—C22—C23111.05 (16)
C11—C9—C8114.05 (13)C22—C23—H23C109.5
C11—C9—C10114.34 (13)C22—C23—H23B109.5
C8—C9—C10113.19 (13)H23C—C23—H23B109.5
C11—C9—H9104.6C22—C23—H23A109.5
C8—C9—H9104.6H23C—C23—H23A109.5
C10—C9—H9104.6H23B—C23—H23A109.5
O2—C11—C12112.46 (13)C10—C19—H19B109.5
O2—C11—C9108.81 (13)C10—C19—H19C109.5
C12—C11—C9112.46 (13)H19B—C19—H19C109.5
O2—C11—H11107.6C10—C19—H19A109.5
C12—C11—H11107.6H19B—C19—H19A109.5
C9—C11—H11107.6H19C—C19—H19A109.5
C13—C12—C11113.42 (14)C13—C18—H18B109.5
C13—C12—H12A108.9C13—C18—H18C109.5
C11—C12—H12A108.9H18B—C18—H18C109.5
C13—C12—H12B108.9C13—C18—H18A109.5
C11—C12—H12B108.9H18B—C18—H18A109.5
H12A—C12—H12B107.7H18C—C18—H18A109.5
O1—C3—C2—C1176.40 (17)C11—C12—C13—C1872.82 (18)
C4—C3—C2—C13.0 (2)C11—C12—C13—C17161.91 (13)
C3—C2—C1—C105.0 (3)C7—C8—C14—C13178.78 (13)
C2—C1—C10—C52.1 (2)C9—C8—C14—C1359.15 (17)
C2—C1—C10—C19120.01 (19)C7—C8—C14—C1557.29 (19)
C2—C1—C10—C9115.16 (19)C9—C8—C14—C15176.92 (14)
O1—C3—C4—C5178.72 (16)C12—C13—C14—C859.11 (18)
C2—C3—C4—C51.9 (2)C18—C13—C14—C865.00 (18)
C3—C4—C5—C6172.13 (15)C17—C13—C14—C8179.81 (13)
C3—C4—C5—C104.8 (3)C12—C13—C14—C15168.80 (14)
C1—C10—C5—C42.9 (2)C18—C13—C14—C1567.09 (17)
C19—C10—C5—C4115.39 (18)C17—C13—C14—C1548.10 (15)
C9—C10—C5—C4120.64 (17)C8—C14—C15—C16160.80 (14)
C1—C10—C5—C6174.22 (14)C13—C14—C15—C1632.06 (17)
C19—C10—C5—C667.52 (18)C14—C15—C16—C172.80 (18)
C9—C10—C5—C656.44 (17)C15—C16—C17—O388.58 (17)
C4—C5—C6—C7117.91 (18)C15—C16—C17—C20148.98 (15)
C10—C5—C6—C759.22 (18)C15—C16—C17—C1326.67 (17)
C5—C6—C7—C856.09 (18)C12—C13—C17—O343.37 (18)
C6—C7—C8—C14172.45 (13)C14—C13—C17—O372.74 (15)
C6—C7—C8—C954.79 (18)C18—C13—C17—O3169.74 (13)
C14—C8—C9—C1153.90 (17)C12—C13—C17—C2074.87 (18)
C7—C8—C9—C11173.27 (14)C14—C13—C17—C20169.03 (14)
C14—C8—C9—C10173.08 (12)C18—C13—C17—C2051.51 (19)
C7—C8—C9—C1053.71 (17)C12—C13—C17—C16161.49 (13)
C1—C10—C9—C1153.88 (17)C14—C13—C17—C1645.39 (15)
C5—C10—C9—C11174.49 (13)C18—C13—C17—C1672.13 (16)
C19—C10—C9—C1166.49 (19)O3—C17—C20—O4154.98 (17)
C1—C10—C9—C8173.23 (13)C16—C17—C20—O430.1 (2)
C5—C10—C9—C852.63 (16)C13—C17—C20—O486.5 (2)
C19—C10—C9—C866.39 (18)O3—C17—C20—C2124.1 (2)
C8—C9—C11—O274.93 (17)C16—C17—C20—C21148.95 (16)
C10—C9—C11—O257.54 (17)C13—C17—C20—C2194.44 (18)
C8—C9—C11—C1250.36 (18)C22—O5—C21—C2077.2 (2)
C10—C9—C11—C12177.17 (13)O4—C20—C21—O516.1 (3)
O2—C11—C12—C1374.46 (17)C17—C20—C21—O5164.80 (15)
C9—C11—C12—C1348.80 (18)C21—O5—C22—O65.9 (3)
C11—C12—C13—C1451.81 (18)C21—O5—C22—C23172.58 (16)
 

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