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The crystal structure of cyproterone (systematic name: 6-chloro-1,2-dihydro-17-hydr­oxy-3'H-cyclo­propa[a]pregna-1,4,6-triene-3,20-dione), C22H27ClO3, is compared with cyproterone acetate, a potent anti-androgen steroid. The two compounds adopt a similar conformation, except for the cyclo­propyl ring attached to the cyclohexenone ring (ring A). Cyproterone further adopts a crystal packing distinct from that of the acetate form. These differences result from hydrogen bonding between the free hydr­oxy group and the carbonyl group of ring A.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031673/at6034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031673/at6034Isup2.hkl
Contains datablock I

CCDC reference: 289627

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.103
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT706_ALERT_1_A H...A Calc 9.61(3), Rep 2.01(3), Dev.. 253.33 Sigma H2A -O25 1.555 1.555 PLAT707_ALERT_1_A D...A Calc 9.717(3), Rep 2.804(3), Dev.. 2304.33 Sigma O24 -O25 1.555 1.555 PLAT707_ALERT_1_A D...A Calc 3.213(2), Rep 3.394(2), Dev.. 90.50 Sigma C15 -O24 1.555 1.555 PLAT707_ALERT_1_A D...A Calc 8.090(3), Rep 3.042(3), Dev.. 1682.67 Sigma C22 -O23 1.555 1.555 PLAT708_ALERT_1_A D-H..A Calc 95(2), Rep 169(3), Dev.. 37.00 Sigma O24 -H2A -O25 1.555 1.555 1.555 PLAT725_ALERT_1_A D-H Calc 7.24000, Rep 0.96000 Dev... 6.28 Ang. C22 -H20A 1.555 1.555 PLAT726_ALERT_1_A H...A Calc 4.07000, Rep 2.49000 Dev... 1.58 Ang. H15B -O24 1.555 1.555 PLAT728_ALERT_1_A D-H..A Calc 25.00, Rep 156.00 Dev... 131.00 Deg. C15 -H15B -O24 1.555 1.555 1.555 PLAT728_ALERT_1_A D-H..A Calc 101.00, Rep 119.00 Dev... 18.00 Deg. C22 -H20A -O23 1.555 1.555 1.555
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 74.99 From the CIF: _reflns_number_total 2271 Count of symmetry unique reflns 2270 Completeness (_total/calc) 100.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
9 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

6-chloro-1,2-dihydro-17-hydroxy-3'H-cyclopropa[a]pregna-1,4,6-triene- 3,20-dione top
Crystal data top
C22H27ClO3Least Squares Treatment of 25 SET4 setting angles.
Mr = 374.89Dx = 1.302 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 21 reflections
a = 6.388 (1) Åθ = 14.0–34.7°
b = 14.182 (2) ŵ = 1.91 mm1
c = 21.107 (3) ÅT = 293 K
V = 1912.2 (5) Å3Prism, colorless
Z = 40.36 × 0.31 × 0.25 mm
F(000) = 800
Data collection top
Enraf–Nonius CAD-4
diffractometer
2223 reflections with I > 2σ(I)
Radiation source: long fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 75.0°, θmin = 3.8°
ω/2θ scansh = 08
Absorption correction: analytical
(Alcock, 1970)
k = 017
Tmin = 0.546, Tmax = 0.646l = 026
2271 measured reflections3 standard reflections every 200 reflections
2271 independent reflections intensity decay: 2.6%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0726P)2 + 0.2755P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2271 reflectionsΔρmax = 0.24 e Å3
250 parametersΔρmin = 0.29 e Å3
0 restraintsAbsolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (2)
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl260.48194 (14)0.48070 (4)0.28454 (3)0.0713 (2)
O250.3435 (4)0.80973 (14)0.36536 (9)0.0646 (6)
O240.3669 (2)0.44701 (11)0.03931 (7)0.0391 (4)
O230.3042 (4)0.55099 (13)0.08865 (8)0.0614 (6)
C10.0888 (4)0.78601 (14)0.20969 (10)0.0383 (6)
C20.1229 (4)0.82428 (16)0.27615 (10)0.0452 (6)
C30.2678 (4)0.77456 (16)0.31753 (10)0.0435 (7)
C40.3216 (4)0.67770 (16)0.30028 (10)0.0404 (6)
C50.2934 (3)0.64242 (13)0.24162 (9)0.0324 (5)
C60.3511 (3)0.54523 (14)0.22582 (10)0.0379 (5)
C70.3147 (3)0.50450 (13)0.17050 (10)0.0358 (5)
C80.2035 (3)0.55381 (12)0.11785 (8)0.0285 (5)
C90.0817 (3)0.64021 (12)0.14219 (8)0.0287 (4)
C100.2178 (3)0.70241 (12)0.18632 (8)0.0303 (5)
C110.0211 (4)0.69331 (13)0.08672 (9)0.0373 (5)
C120.1611 (3)0.62932 (13)0.04663 (9)0.0356 (5)
C130.0463 (3)0.54051 (13)0.02449 (8)0.0285 (4)
C140.0488 (3)0.49035 (12)0.08275 (8)0.0280 (4)
C150.1185 (3)0.39401 (13)0.05732 (10)0.0362 (6)
C160.0408 (3)0.37218 (15)0.00384 (10)0.0394 (5)
C170.1864 (3)0.45895 (13)0.00009 (8)0.0320 (5)
C220.0794 (4)0.77461 (18)0.25735 (11)0.0474 (7)
C190.4133 (4)0.74080 (15)0.15244 (10)0.0418 (6)
C180.1223 (4)0.56476 (17)0.02521 (9)0.0406 (6)
C200.2902 (4)0.47460 (17)0.06495 (9)0.0412 (6)
C210.3858 (6)0.3901 (2)0.09594 (14)0.0668 (10)
H10.076 (4)0.828 (2)0.1811 (13)0.049 (7)*
H20.122 (5)0.8912 (19)0.2824 (12)0.052 (7)*
H2A0.345 (5)0.406 (2)0.0649 (15)0.059 (9)*
H40.377800.638600.331300.0480*
H70.360000.442900.164200.0430*
H80.308500.575800.087400.0340*
H90.032900.615700.168300.0340*
H11A0.104200.744900.103300.0450*
H11B0.087400.720000.060000.0450*
H12A0.210000.664100.009900.0430*
H12B0.282600.611100.071300.0430*
H140.067200.478300.112100.0340*
H15A0.112600.346400.090300.0430*
H15B0.259900.397000.040800.0430*
H16A0.031000.362500.036100.0470*
H16B0.120600.315900.013800.0470*
H18A0.103700.711900.274100.0570*
H18B0.204200.812900.252600.0570*
H19A0.488100.782100.180500.0630*
H19B0.371600.775000.115300.0630*
H19C0.502200.689200.140400.0630*
H20A0.057600.594600.061000.0610*
H20B0.190900.508000.038700.0610*
H20C0.223400.606700.006800.0610*
H22A0.465600.409700.132200.1000*
H22B0.476100.358700.066400.1000*
H22C0.277000.347800.109200.1000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl260.1105 (6)0.0475 (3)0.0559 (3)0.0247 (4)0.0448 (4)0.0035 (2)
O250.0717 (12)0.0718 (11)0.0502 (9)0.0063 (11)0.0116 (9)0.0317 (9)
O240.0309 (7)0.0475 (8)0.0389 (7)0.0037 (7)0.0020 (6)0.0093 (7)
O230.0796 (13)0.0594 (10)0.0452 (8)0.0077 (11)0.0227 (10)0.0110 (8)
C10.0519 (12)0.0276 (8)0.0355 (9)0.0051 (9)0.0006 (9)0.0040 (8)
C20.0562 (13)0.0372 (10)0.0421 (10)0.0043 (10)0.0018 (10)0.0137 (9)
C30.0459 (12)0.0494 (12)0.0353 (10)0.0037 (10)0.0043 (9)0.0147 (9)
C40.0454 (11)0.0441 (10)0.0317 (9)0.0012 (10)0.0053 (8)0.0030 (8)
C50.0345 (9)0.0314 (9)0.0312 (8)0.0011 (8)0.0022 (8)0.0011 (7)
C60.0446 (10)0.0318 (9)0.0374 (9)0.0047 (9)0.0135 (9)0.0030 (8)
C70.0393 (10)0.0283 (8)0.0398 (9)0.0050 (8)0.0089 (8)0.0022 (7)
C80.0318 (8)0.0260 (8)0.0278 (8)0.0009 (7)0.0008 (7)0.0034 (6)
C90.0341 (9)0.0243 (7)0.0278 (7)0.0019 (7)0.0002 (7)0.0002 (7)
C100.0373 (9)0.0254 (8)0.0281 (8)0.0004 (8)0.0022 (8)0.0040 (7)
C110.0499 (11)0.0271 (8)0.0349 (8)0.0064 (9)0.0081 (9)0.0016 (7)
C120.0401 (10)0.0327 (8)0.0341 (9)0.0067 (8)0.0068 (8)0.0010 (7)
C130.0307 (8)0.0303 (8)0.0246 (7)0.0007 (8)0.0001 (7)0.0004 (6)
C140.0303 (8)0.0271 (8)0.0265 (7)0.0002 (7)0.0010 (7)0.0002 (7)
C150.0373 (10)0.0293 (9)0.0419 (10)0.0036 (8)0.0073 (9)0.0068 (8)
C160.0406 (10)0.0371 (9)0.0405 (9)0.0001 (9)0.0061 (9)0.0091 (8)
C170.0323 (9)0.0352 (9)0.0284 (8)0.0029 (8)0.0002 (7)0.0015 (7)
C220.0440 (11)0.0524 (13)0.0458 (11)0.0092 (10)0.0008 (10)0.0102 (10)
C190.0457 (11)0.0386 (10)0.0410 (10)0.0121 (9)0.0065 (9)0.0058 (8)
C180.0415 (10)0.0501 (11)0.0303 (8)0.0083 (10)0.0057 (9)0.0015 (8)
C200.0401 (10)0.0523 (12)0.0313 (9)0.0056 (10)0.0049 (8)0.0017 (9)
C210.080 (2)0.0654 (16)0.0549 (14)0.0134 (16)0.0273 (16)0.0097 (13)
Geometric parameters (Å, º) top
Cl26—C61.753 (2)C17—C201.537 (3)
O25—C31.226 (3)C20—C211.496 (4)
O24—C171.432 (2)C1—H10.85 (3)
O23—C201.197 (3)C2—H20.96 (3)
O24—H2A0.81 (3)C4—H40.9301
C1—C21.520 (3)C7—H70.9298
C1—C221.481 (3)C8—H80.9799
C1—C101.526 (3)C9—H90.9800
C2—C31.455 (3)C11—H11A0.9693
C2—C221.524 (4)C11—H11B0.9704
C3—C41.462 (3)C12—H12A0.9705
C4—C51.348 (3)C12—H12B0.9697
C5—C61.465 (3)C14—H140.9808
C5—C101.523 (3)C15—H15A0.9705
C6—C71.323 (3)C15—H15B0.9692
C7—C81.493 (3)C16—H16A0.9695
C8—C141.528 (3)C16—H16B0.9701
C8—C91.540 (2)C22—H18A0.9696
C9—C111.539 (3)C22—H18B0.9698
C9—C101.550 (3)C19—H19A0.9603
C10—C191.539 (3)C19—H19B0.9595
C11—C121.530 (3)C19—H19C0.9605
C12—C131.531 (3)C18—H20A0.9595
C13—C141.545 (2)C18—H20B0.9597
C13—C181.542 (3)C18—H20C0.9601
C13—C171.552 (3)C21—H22A0.9607
C14—C151.534 (3)C21—H22B0.9591
C15—C161.551 (3)C21—H22C0.9598
C16—C171.545 (3)
Cl26···O23i3.406 (2)H8···C192.7944
Cl26···C2ii3.596 (3)H8···C182.6625
Cl26···H42.5360H8···H11B2.5518
Cl26···H18Biii3.0701H8···H19C2.3171
Cl26···H19Aii2.9179H8···H20C2.1073
O25···O24iv2.804 (3)H9···C62.9138
O24···C15v3.394 (2)H9···C222.9496
O24···O25iii2.804 (3)H9···H12B2.5962
O24···O233.103 (2)H9···H142.2918
O23···Cl26vi3.406 (2)H11A···C12.6273
O23···C183.042 (3)H11A···H12.3261
O23···O243.103 (2)H11B···C192.8685
O23···C123.197 (3)H11B···C182.8516
O25···H7vii2.7466H11B···H82.5518
O25···H2Aiv2.01 (3)H11B···H19B2.2949
O24···H142.4945H11B···H20C2.3075
O24···H15Bv2.4875H11B···H12Axi2.5600
O24···H12B2.4822H12A···O232.6948
O24···H22B2.6521H12A···H20A2.4765
O23···H12A2.6948H12A···H11Bviii2.5600
O23···H20A2.4627H12B···O242.4822
O23···H1viii2.71 (3)H12B···H92.5962
O23···H19Bviii2.7691H12B···H142.4864
C2···Cl26vii3.596 (3)H12B···H19Cv2.2899
C7···C193.431 (3)H14···O242.4945
C12···O233.197 (3)H14···H2A2.2788
C15···O24ix3.394 (2)H14···H92.2918
C19···C73.431 (3)H14···H12B2.4864
C18···O233.042 (3)H14···H2iii2.5704
C1···H11A2.6273H15A···C73.0919
C4···H18A2.8145H15B···O24ix2.4875
C4···H22Ax2.9562H15B···C182.8938
C5···H18A2.8064H15B···H2Aix2.5778
C6···H92.9138H15B···H20B2.3427
C6···H19C2.8898H16A···C182.9362
C7···H19C2.9495H16A···C212.9728
C7···H15A3.0919H16A···H20B2.3031
C8···H20C2.7388H16A···H22C2.5090
C8···H19C2.7485H16B···C213.0565
C11···H20C2.8008H16B···H2A2.2025
C11···H12.83 (3)H18A···C42.8145
C11···H19B2.8282H18A···C52.8064
C12···H19Cv3.0438H18B···H19Av2.5239
C14···H2A2.81 (3)H18B···Cl26iv3.0701
C15···H72.8195H19A···H18Bix2.5239
C15···H2A2.97 (3)H19A···Cl26vii2.9179
C15···H20B2.6334H19B···C112.8282
C16···H22C2.8441H19B···H12.4616
C16···H20B2.5898H19B···H11B2.2949
C22···H92.9496H19B···O23xi2.7691
C19···H82.7944H19B···H20Axi2.4790
C19···H11B2.8685H19C···C62.8898
C18···H82.6625H19C···C72.9495
C18···H11B2.8516H19C···C82.7485
C18···H15B2.8938H19C···C12ix3.0438
C18···H16A2.9362H19C···H82.3171
C20···H20A2.7999H19C···H12Bix2.2899
C21···H16A2.9728H20A···O232.4627
C21···H16B3.0565H20A···C202.7999
H1···C112.83 (3)H20A···H12A2.4765
H1···H11A2.3261H20A···H19Bviii2.4790
H1···H19B2.4616H20B···C152.6334
H1···O23xi2.71 (3)H20B···C162.5898
H2···H14iv2.5704H20B···H15B2.3427
H2A···C142.81 (3)H20B···H16A2.3031
H2A···C152.97 (3)H20C···C82.7388
H2A···H142.2788H20C···C112.8008
H2A···H15Bv2.5778H20C···H82.1073
H2A···H16B2.2025H20C···H11B2.3075
H2A···O25iii2.01 (3)H22A···C4xii2.9562
H4···Cl262.5360H22B···O242.6521
H7···C152.8195H22C···C162.8441
H7···O25ii2.7466H22C···H16A2.5090
C17—O24—H2A110 (2)C22—C2—H2119.2 (19)
C2—C1—C2261.05 (16)C3—C4—H4118.40
C10—C1—C22121.78 (18)C5—C4—H4118.49
C2—C1—C10119.90 (19)C6—C7—H7118.79
C1—C2—C2258.21 (15)C8—C7—H7118.80
C3—C2—C22118.1 (2)C7—C8—H8108.16
C1—C2—C3118.2 (2)C9—C8—H8108.15
O25—C3—C4119.7 (2)C14—C8—H8108.19
C2—C3—C4117.09 (19)C8—C9—H9106.43
O25—C3—C2123.3 (2)C10—C9—H9106.44
C3—C4—C5123.1 (2)C11—C9—H9106.41
C4—C5—C6121.65 (18)C9—C11—H11A109.17
C6—C5—C10115.52 (16)C9—C11—H11B109.16
C4—C5—C10122.63 (17)C12—C11—H11A109.11
Cl26—C6—C5116.76 (15)C12—C11—H11B109.12
C5—C6—C7124.56 (18)H11A—C11—H11B107.85
Cl26—C6—C7118.67 (15)C11—C12—H12A109.18
C6—C7—C8122.41 (17)C11—C12—H12B109.21
C7—C8—C9111.40 (14)C13—C12—H12A109.18
C9—C8—C14107.68 (15)C13—C12—H12B109.16
C7—C8—C14113.12 (14)H12A—C12—H12B107.86
C8—C9—C10111.72 (15)C8—C14—H14106.56
C10—C9—C11114.71 (14)C13—C14—H14106.61
C8—C9—C11110.56 (14)C15—C14—H14106.56
C1—C10—C9109.49 (16)C14—C15—H15A110.94
C1—C10—C19108.28 (16)C14—C15—H15B110.94
C5—C10—C9108.70 (14)C16—C15—H15A110.96
C5—C10—C19107.25 (16)C16—C15—H15B111.00
C9—C10—C19112.17 (15)H15A—C15—H15B108.95
C1—C10—C5110.95 (15)C15—C16—H16A110.53
C9—C11—C12112.33 (15)C15—C16—H16B110.57
C11—C12—C13112.15 (16)C17—C16—H16A110.55
C12—C13—C17116.05 (16)C17—C16—H16B110.53
C12—C13—C18111.02 (16)H16A—C16—H16B108.69
C12—C13—C14108.92 (14)C1—C22—H18A117.65
C14—C13—C18111.68 (16)C1—C22—H18B117.72
C17—C13—C18109.97 (15)C2—C22—H18A117.69
C14—C13—C1798.61 (14)C2—C22—H18B117.71
C8—C14—C15120.43 (16)H18A—C22—H18B114.82
C13—C14—C15104.22 (14)C10—C19—H19A109.45
C8—C14—C13111.65 (14)C10—C19—H19B109.46
C14—C15—C16104.01 (15)C10—C19—H19C109.47
C15—C16—C17105.97 (16)H19A—C19—H19B109.49
O24—C17—C16111.07 (15)H19A—C19—H19C109.49
O24—C17—C20100.78 (16)H19B—C19—H19C109.46
O24—C17—C13111.00 (14)C13—C18—H20A109.45
C13—C17—C20116.03 (16)C13—C18—H20B109.49
C16—C17—C20115.00 (16)C13—C18—H20C109.43
C13—C17—C16103.21 (15)H20A—C18—H20B109.45
C1—C22—C260.74 (15)H20A—C18—H20C109.58
O23—C20—C21120.8 (2)H20B—C18—H20C109.42
C17—C20—C21116.7 (2)C20—C21—H22A109.47
O23—C20—C17122.4 (2)C20—C21—H22B109.47
C2—C1—H1114.7 (19)C20—C21—H22C109.43
C10—C1—H1111.5 (18)H22A—C21—H22B109.46
C22—C1—H1119.2 (18)H22A—C21—H22C109.44
C1—C2—H2118.7 (15)H22B—C21—H22C109.57
C3—C2—H2113.7 (17)
C10—C1—C2—C34.8 (3)C14—C8—C9—C10172.23 (14)
C10—C1—C2—C22112.1 (2)C8—C9—C10—C1179.24 (15)
C2—C1—C10—C1992.1 (2)C11—C9—C10—C5175.28 (16)
C22—C1—C10—C547.2 (3)C11—C9—C10—C1966.3 (2)
C22—C1—C10—C972.8 (2)C8—C9—C11—C1255.2 (2)
C22—C1—C10—C19164.6 (2)C10—C9—C11—C12177.42 (16)
C10—C1—C22—C2109.1 (2)C8—C9—C10—C557.89 (19)
C22—C1—C2—C3107.3 (2)C8—C9—C10—C1960.53 (19)
C2—C1—C10—C525.4 (3)C11—C9—C10—C153.9 (2)
C2—C1—C10—C9145.33 (19)C9—C11—C12—C1352.8 (2)
C22—C2—C3—C449.1 (3)C11—C12—C13—C17163.75 (15)
C3—C2—C22—C1107.4 (2)C11—C12—C13—C1869.7 (2)
C1—C2—C3—C417.9 (3)C11—C12—C13—C1453.7 (2)
C22—C2—C3—O25130.5 (3)C12—C13—C14—C15168.70 (15)
C1—C2—C3—O25162.6 (2)C18—C13—C14—C863.2 (2)
O25—C3—C4—C5161.6 (2)C17—C13—C14—C8178.79 (14)
C2—C3—C4—C518.9 (4)C17—C13—C14—C1547.28 (17)
C3—C4—C5—C104.7 (3)C12—C13—C14—C859.79 (19)
C3—C4—C5—C6179.4 (2)C12—C13—C17—C2072.2 (2)
C10—C5—C6—C79.7 (3)C14—C13—C17—O2474.04 (17)
C4—C5—C10—C126.1 (3)C14—C13—C17—C1645.02 (16)
C10—C5—C6—Cl26168.95 (14)C14—C13—C17—C20171.72 (16)
C4—C5—C10—C1991.9 (2)C18—C13—C14—C1568.31 (19)
C6—C5—C10—C1158.92 (17)C12—C13—C17—O2442.0 (2)
C4—C5—C10—C9146.6 (2)C12—C13—C17—C16161.06 (15)
C6—C5—C10—C1983.01 (19)C18—C13—C17—C2054.8 (2)
C4—C5—C6—Cl266.1 (3)C18—C13—C17—O24169.05 (16)
C6—C5—C10—C938.5 (2)C18—C13—C17—C1671.89 (18)
C4—C5—C6—C7175.3 (2)C13—C14—C15—C1631.17 (19)
C5—C6—C7—C81.7 (3)C8—C14—C15—C16157.35 (15)
Cl26—C6—C7—C8179.69 (15)C14—C15—C16—C172.30 (19)
C6—C7—C8—C917.8 (3)C15—C16—C17—O2491.94 (18)
C6—C7—C8—C14139.23 (19)C15—C16—C17—C1327.08 (18)
C7—C8—C9—C1047.7 (2)C15—C16—C17—C20154.44 (17)
C7—C8—C14—C13174.16 (15)C13—C17—C20—O2316.7 (3)
C7—C8—C14—C1551.5 (2)C16—C17—C20—O23137.3 (2)
C9—C8—C14—C1362.31 (18)C16—C17—C20—C2146.3 (3)
C9—C8—C14—C15175.03 (15)C13—C17—C20—C21166.9 (2)
C14—C8—C9—C1158.73 (19)O24—C17—C20—O23103.2 (3)
C7—C8—C9—C11176.69 (16)O24—C17—C20—C2173.2 (3)
Symmetry codes: (i) x+1/2, y+1, z+1/2; (ii) x+1, y1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x1, y, z; (vi) x+1/2, y+1, z1/2; (vii) x+1, y+1/2, z+1/2; (viii) x1/2, y+3/2, z; (ix) x+1, y, z; (x) x1/2, y+1, z+1/2; (xi) x+1/2, y+3/2, z; (xii) x1/2, y+1, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O24—H2A···O250.81 (3)2.01 (3)2.804 (3)169 (3)
C4—H4···Cl260.932.542.994 (2)111
C12—H12B···O240.972.482.905 (2)106
C14—H14···O240.982.492.876 (2)103
C15—H15B···O240.972.493.394 (2)156
C22—H20A···O230.962.463.042 (3)119
Deviations (Å) of the steroid nucleus from the plane defined by atoms C3, C4, C5, C6, C7 and Cl1 top
NameCPACPH
C1-0.04-0.19
C2-0.16-0.28
C3+0.01+0.01
C4-0.04-0.04
C5+0.08+0.04
C6+0.01+0.00
C7-0.04-0.02
C8-0.07-0.04
C9-0.45-0.47
C10+0.37+0.29
C11-0.41-0.40
C12-1.30-1.22
C13-0.93-0.85
C14-1.00-0.96
C15-0.93-0.86
C16-1.70-1.50
C17-1.96-1.86
C21-1.36-1.52
O25+0.14+0.27
Cl26+0.01+0.01
Torsion angles (°) in rings A and D (°) top
Note: φA–B is the torsion angle about the A—B bond in which the two atoms required to define the angle are those attached to either end of the bond and are in the same ring in question.
Ring AφA–B (CPA)φA–B (CPH)
C1–C2-6.2-4.8
C2–C3-12.7-17.9
C3–C4+14.1+18.9
C4–C5+4.9+4.7
C5–C10-22.8-26.1
C1–C10+23.0+25.4
Ring D
C13—C14+46.6+47.3
C14—C15-36.4-31.2
C15—C16+11.4+2.3
C16—C17+16.7+27.1
C13—C17-38.1-45.0
 

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