Cyproterone and a comparison with its acetate ester

Ruyck, J. de; Henry de Hassonville, S.; Liégeois, J.-F.; Wouters, J.

doi:10.1107/S1600536805031673

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Cyproterone and a comparison with its acetate ester

J. de Ruyck, S. Henry de Hassonville, J.-F. Liégeois and J. Wouters

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031673/at6034sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031673/at6034Isup2.hkl Contains datablock I

CCDC reference: 289627

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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

C₂₂H₂₇ClO₃	Least Squares Treatment of 25 SET4 setting angles.
M_r = 374.89	D_x = 1.302 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 21 reflections
a = 6.388 (1) Å	θ = 14.0–34.7°
b = 14.182 (2) Å	µ = 1.91 mm⁻¹
c = 21.107 (3) Å	T = 293 K
V = 1912.2 (5) Å³	Prism, colorless
Z = 4	0.36 × 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 tube	R_int = 0.000
Graphite monochromator	θ_max = 75.0°, θ_min = 3.8°
ω/2θ scans	h = 0→8
Absorption correction: analytical (Alcock, 1970)	k = 0→17
T_min = 0.546, T_max = 0.646	l = 0→26
2271 measured reflections	3 standard reflections every 200 reflections
2271 independent reflections	intensity decay: 2.6%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0726P)² + 0.2755P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2271 reflections	Δρ_max = 0.24 e Å⁻³
250 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute 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

	x	y	z	U_iso*/U_eq
Cl26	0.48194 (14)	0.48070 (4)	0.28454 (3)	0.0713 (2)
O25	0.3435 (4)	0.80973 (14)	0.36536 (9)	0.0646 (6)
O24	−0.3669 (2)	0.44701 (11)	0.03931 (7)	0.0391 (4)
O23	−0.3042 (4)	0.55099 (13)	−0.08865 (8)	0.0614 (6)
C1	0.0888 (4)	0.78601 (14)	0.20969 (10)	0.0383 (6)
C2	0.1229 (4)	0.82428 (16)	0.27615 (10)	0.0452 (6)
C3	0.2678 (4)	0.77456 (16)	0.31753 (10)	0.0435 (7)
C4	0.3216 (4)	0.67770 (16)	0.30028 (10)	0.0404 (6)
C5	0.2934 (3)	0.64242 (13)	0.24162 (9)	0.0324 (5)
C6	0.3511 (3)	0.54523 (14)	0.22582 (10)	0.0379 (5)
C7	0.3147 (3)	0.50450 (13)	0.17050 (10)	0.0358 (5)
C8	0.2035 (3)	0.55381 (12)	0.11785 (8)	0.0285 (5)
C9	0.0817 (3)	0.64021 (12)	0.14219 (8)	0.0287 (4)
C10	0.2178 (3)	0.70241 (12)	0.18632 (8)	0.0303 (5)
C11	−0.0211 (4)	0.69331 (13)	0.08672 (9)	0.0373 (5)
C12	−0.1611 (3)	0.62932 (13)	0.04663 (9)	0.0356 (5)
C13	−0.0463 (3)	0.54051 (13)	0.02449 (8)	0.0285 (4)
C14	0.0488 (3)	0.49035 (12)	0.08275 (8)	0.0280 (4)
C15	0.1185 (3)	0.39401 (13)	0.05732 (10)	0.0362 (6)
C16	−0.0408 (3)	0.37218 (15)	0.00384 (10)	0.0394 (5)
C17	−0.1864 (3)	0.45895 (13)	−0.00009 (8)	0.0320 (5)
C22	−0.0794 (4)	0.77461 (18)	0.25735 (11)	0.0474 (7)
C19	0.4133 (4)	0.74080 (15)	0.15244 (10)	0.0418 (6)
C18	0.1223 (4)	0.56476 (17)	−0.02521 (9)	0.0406 (6)
C20	−0.2902 (4)	0.47460 (17)	−0.06495 (9)	0.0412 (6)
C21	−0.3858 (6)	0.3901 (2)	−0.09594 (14)	0.0668 (10)
H1	0.076 (4)	0.828 (2)	0.1811 (13)	0.049 (7)*
H2	0.122 (5)	0.8912 (19)	0.2824 (12)	0.052 (7)*
H2A	−0.345 (5)	0.406 (2)	0.0649 (15)	0.059 (9)*
H4	0.37780	0.63860	0.33130	0.0480*
H7	0.36000	0.44290	0.16420	0.0430*
H8	0.30850	0.57580	0.08740	0.0340*
H9	−0.03290	0.61570	0.16830	0.0340*
H11A	−0.10420	0.74490	0.10330	0.0450*
H11B	0.08740	0.72000	0.06000	0.0450*
H12A	−0.21000	0.66410	0.00990	0.0430*
H12B	−0.28260	0.61110	0.07130	0.0430*
H14	−0.06720	0.47830	0.11210	0.0340*
H15A	0.11260	0.34640	0.09030	0.0430*
H15B	0.25990	0.39700	0.04080	0.0430*
H16A	0.03100	0.36250	−0.03610	0.0470*
H16B	−0.12060	0.31590	0.01380	0.0470*
H18A	−0.10370	0.71190	0.27410	0.0570*
H18B	−0.20420	0.81290	0.25260	0.0570*
H19A	0.48810	0.78210	0.18050	0.0630*
H19B	0.37160	0.77500	0.11530	0.0630*
H19C	0.50220	0.68920	0.14040	0.0630*
H20A	0.05760	0.59460	−0.06100	0.0610*
H20B	0.19090	0.50800	−0.03870	0.0610*
H20C	0.22340	0.60670	−0.00680	0.0610*
H22A	−0.46560	0.40970	−0.13220	0.1000*
H22B	−0.47610	0.35870	−0.06640	0.1000*
H22C	−0.27700	0.34780	−0.10920	0.1000*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl26	0.1105 (6)	0.0475 (3)	0.0559 (3)	0.0247 (4)	−0.0448 (4)	−0.0035 (2)
O25	0.0717 (12)	0.0718 (11)	0.0502 (9)	0.0063 (11)	−0.0116 (9)	−0.0317 (9)
O24	0.0309 (7)	0.0475 (8)	0.0389 (7)	−0.0037 (7)	0.0020 (6)	0.0093 (7)
O23	0.0796 (13)	0.0594 (10)	0.0452 (8)	−0.0077 (11)	−0.0227 (10)	0.0110 (8)
C1	0.0519 (12)	0.0276 (8)	0.0355 (9)	0.0051 (9)	−0.0006 (9)	−0.0040 (8)
C2	0.0562 (13)	0.0372 (10)	0.0421 (10)	0.0043 (10)	0.0018 (10)	−0.0137 (9)
C3	0.0459 (12)	0.0494 (12)	0.0353 (10)	−0.0037 (10)	0.0043 (9)	−0.0147 (9)
C4	0.0454 (11)	0.0441 (10)	0.0317 (9)	0.0012 (10)	−0.0053 (8)	−0.0030 (8)
C5	0.0345 (9)	0.0314 (9)	0.0312 (8)	−0.0011 (8)	−0.0022 (8)	−0.0011 (7)
C6	0.0446 (10)	0.0318 (9)	0.0374 (9)	0.0047 (9)	−0.0135 (9)	0.0030 (8)
C7	0.0393 (10)	0.0283 (8)	0.0398 (9)	0.0050 (8)	−0.0089 (8)	−0.0022 (7)
C8	0.0318 (8)	0.0260 (8)	0.0278 (8)	0.0009 (7)	−0.0008 (7)	−0.0034 (6)
C9	0.0341 (9)	0.0243 (7)	0.0278 (7)	0.0019 (7)	0.0002 (7)	−0.0002 (7)
C10	0.0373 (9)	0.0254 (8)	0.0281 (8)	0.0004 (8)	0.0022 (8)	−0.0040 (7)
C11	0.0499 (11)	0.0271 (8)	0.0349 (8)	0.0064 (9)	−0.0081 (9)	0.0016 (7)
C12	0.0401 (10)	0.0327 (8)	0.0341 (9)	0.0067 (8)	−0.0068 (8)	0.0010 (7)
C13	0.0307 (8)	0.0303 (8)	0.0246 (7)	−0.0007 (8)	0.0001 (7)	0.0004 (6)
C14	0.0303 (8)	0.0271 (8)	0.0265 (7)	0.0002 (7)	−0.0010 (7)	0.0002 (7)
C15	0.0373 (10)	0.0293 (9)	0.0419 (10)	0.0036 (8)	−0.0073 (9)	−0.0068 (8)
C16	0.0406 (10)	0.0371 (9)	0.0405 (9)	0.0001 (9)	−0.0061 (9)	−0.0091 (8)
C17	0.0323 (9)	0.0352 (9)	0.0284 (8)	−0.0029 (8)	0.0002 (7)	−0.0015 (7)
C22	0.0440 (11)	0.0524 (13)	0.0458 (11)	0.0092 (10)	0.0008 (10)	−0.0102 (10)
C19	0.0457 (11)	0.0386 (10)	0.0410 (10)	−0.0121 (9)	0.0065 (9)	−0.0058 (8)
C18	0.0415 (10)	0.0501 (11)	0.0303 (8)	−0.0083 (10)	0.0057 (9)	0.0015 (8)
C20	0.0401 (10)	0.0523 (12)	0.0313 (9)	−0.0056 (10)	−0.0049 (8)	−0.0017 (9)
C21	0.080 (2)	0.0654 (16)	0.0549 (14)	−0.0134 (16)	−0.0273 (16)	−0.0097 (13)

Geometric parameters (Å, º) top

Cl26—C6	1.753 (2)	C17—C20	1.537 (3)
O25—C3	1.226 (3)	C20—C21	1.496 (4)
O24—C17	1.432 (2)	C1—H1	0.85 (3)
O23—C20	1.197 (3)	C2—H2	0.96 (3)
O24—H2A	0.81 (3)	C4—H4	0.9301
C1—C2	1.520 (3)	C7—H7	0.9298
C1—C22	1.481 (3)	C8—H8	0.9799
C1—C10	1.526 (3)	C9—H9	0.9800
C2—C3	1.455 (3)	C11—H11A	0.9693
C2—C22	1.524 (4)	C11—H11B	0.9704
C3—C4	1.462 (3)	C12—H12A	0.9705
C4—C5	1.348 (3)	C12—H12B	0.9697
C5—C6	1.465 (3)	C14—H14	0.9808
C5—C10	1.523 (3)	C15—H15A	0.9705
C6—C7	1.323 (3)	C15—H15B	0.9692
C7—C8	1.493 (3)	C16—H16A	0.9695
C8—C14	1.528 (3)	C16—H16B	0.9701
C8—C9	1.540 (2)	C22—H18A	0.9696
C9—C11	1.539 (3)	C22—H18B	0.9698
C9—C10	1.550 (3)	C19—H19A	0.9603
C10—C19	1.539 (3)	C19—H19B	0.9595
C11—C12	1.530 (3)	C19—H19C	0.9605
C12—C13	1.531 (3)	C18—H20A	0.9595
C13—C14	1.545 (2)	C18—H20B	0.9597
C13—C18	1.542 (3)	C18—H20C	0.9601
C13—C17	1.552 (3)	C21—H22A	0.9607
C14—C15	1.534 (3)	C21—H22B	0.9591
C15—C16	1.551 (3)	C21—H22C	0.9598
C16—C17	1.545 (3)

Cl26···O23ⁱ	3.406 (2)	H8···C19	2.7944
Cl26···C2ⁱⁱ	3.596 (3)	H8···C18	2.6625
Cl26···H4	2.5360	H8···H11B	2.5518
Cl26···H18Bⁱⁱⁱ	3.0701	H8···H19C	2.3171
Cl26···H19Aⁱⁱ	2.9179	H8···H20C	2.1073
O25···O24^iv	2.804 (3)	H9···C6	2.9138
O24···C15^v	3.394 (2)	H9···C22	2.9496
O24···O25ⁱⁱⁱ	2.804 (3)	H9···H12B	2.5962
O24···O23	3.103 (2)	H9···H14	2.2918
O23···Cl26^vi	3.406 (2)	H11A···C1	2.6273
O23···C18	3.042 (3)	H11A···H1	2.3261
O23···O24	3.103 (2)	H11B···C19	2.8685
O23···C12	3.197 (3)	H11B···C18	2.8516
O25···H7^vii	2.7466	H11B···H8	2.5518
O25···H2A^iv	2.01 (3)	H11B···H19B	2.2949
O24···H14	2.4945	H11B···H20C	2.3075
O24···H15B^v	2.4875	H11B···H12A^xi	2.5600
O24···H12B	2.4822	H12A···O23	2.6948
O24···H22B	2.6521	H12A···H20A	2.4765
O23···H12A	2.6948	H12A···H11B^viii	2.5600
O23···H20A	2.4627	H12B···O24	2.4822
O23···H1^viii	2.71 (3)	H12B···H9	2.5962
O23···H19B^viii	2.7691	H12B···H14	2.4864
C2···Cl26^vii	3.596 (3)	H12B···H19C^v	2.2899
C7···C19	3.431 (3)	H14···O24	2.4945
C12···O23	3.197 (3)	H14···H2A	2.2788
C15···O24^ix	3.394 (2)	H14···H9	2.2918
C19···C7	3.431 (3)	H14···H12B	2.4864
C18···O23	3.042 (3)	H14···H2ⁱⁱⁱ	2.5704
C1···H11A	2.6273	H15A···C7	3.0919
C4···H18A	2.8145	H15B···O24^ix	2.4875
C4···H22A^x	2.9562	H15B···C18	2.8938
C5···H18A	2.8064	H15B···H2A^ix	2.5778
C6···H9	2.9138	H15B···H20B	2.3427
C6···H19C	2.8898	H16A···C18	2.9362
C7···H19C	2.9495	H16A···C21	2.9728
C7···H15A	3.0919	H16A···H20B	2.3031
C8···H20C	2.7388	H16A···H22C	2.5090
C8···H19C	2.7485	H16B···C21	3.0565
C11···H20C	2.8008	H16B···H2A	2.2025
C11···H1	2.83 (3)	H18A···C4	2.8145
C11···H19B	2.8282	H18A···C5	2.8064
C12···H19C^v	3.0438	H18B···H19A^v	2.5239
C14···H2A	2.81 (3)	H18B···Cl26^iv	3.0701
C15···H7	2.8195	H19A···H18B^ix	2.5239
C15···H2A	2.97 (3)	H19A···Cl26^vii	2.9179
C15···H20B	2.6334	H19B···C11	2.8282
C16···H22C	2.8441	H19B···H1	2.4616
C16···H20B	2.5898	H19B···H11B	2.2949
C22···H9	2.9496	H19B···O23^xi	2.7691
C19···H8	2.7944	H19B···H20A^xi	2.4790
C19···H11B	2.8685	H19C···C6	2.8898
C18···H8	2.6625	H19C···C7	2.9495
C18···H11B	2.8516	H19C···C8	2.7485
C18···H15B	2.8938	H19C···C12^ix	3.0438
C18···H16A	2.9362	H19C···H8	2.3171
C20···H20A	2.7999	H19C···H12B^ix	2.2899
C21···H16A	2.9728	H20A···O23	2.4627
C21···H16B	3.0565	H20A···C20	2.7999
H1···C11	2.83 (3)	H20A···H12A	2.4765
H1···H11A	2.3261	H20A···H19B^viii	2.4790
H1···H19B	2.4616	H20B···C15	2.6334
H1···O23^xi	2.71 (3)	H20B···C16	2.5898
H2···H14^iv	2.5704	H20B···H15B	2.3427
H2A···C14	2.81 (3)	H20B···H16A	2.3031
H2A···C15	2.97 (3)	H20C···C8	2.7388
H2A···H14	2.2788	H20C···C11	2.8008
H2A···H15B^v	2.5778	H20C···H8	2.1073
H2A···H16B	2.2025	H20C···H11B	2.3075
H2A···O25ⁱⁱⁱ	2.01 (3)	H22A···C4^xii	2.9562
H4···Cl26	2.5360	H22B···O24	2.6521
H7···C15	2.8195	H22C···C16	2.8441
H7···O25ⁱⁱ	2.7466	H22C···H16A	2.5090

C17—O24—H2A	110 (2)	C22—C2—H2	119.2 (19)
C2—C1—C22	61.05 (16)	C3—C4—H4	118.40
C10—C1—C22	121.78 (18)	C5—C4—H4	118.49
C2—C1—C10	119.90 (19)	C6—C7—H7	118.79
C1—C2—C22	58.21 (15)	C8—C7—H7	118.80
C3—C2—C22	118.1 (2)	C7—C8—H8	108.16
C1—C2—C3	118.2 (2)	C9—C8—H8	108.15
O25—C3—C4	119.7 (2)	C14—C8—H8	108.19
C2—C3—C4	117.09 (19)	C8—C9—H9	106.43
O25—C3—C2	123.3 (2)	C10—C9—H9	106.44
C3—C4—C5	123.1 (2)	C11—C9—H9	106.41
C4—C5—C6	121.65 (18)	C9—C11—H11A	109.17
C6—C5—C10	115.52 (16)	C9—C11—H11B	109.16
C4—C5—C10	122.63 (17)	C12—C11—H11A	109.11
Cl26—C6—C5	116.76 (15)	C12—C11—H11B	109.12
C5—C6—C7	124.56 (18)	H11A—C11—H11B	107.85
Cl26—C6—C7	118.67 (15)	C11—C12—H12A	109.18
C6—C7—C8	122.41 (17)	C11—C12—H12B	109.21
C7—C8—C9	111.40 (14)	C13—C12—H12A	109.18
C9—C8—C14	107.68 (15)	C13—C12—H12B	109.16
C7—C8—C14	113.12 (14)	H12A—C12—H12B	107.86
C8—C9—C10	111.72 (15)	C8—C14—H14	106.56
C10—C9—C11	114.71 (14)	C13—C14—H14	106.61
C8—C9—C11	110.56 (14)	C15—C14—H14	106.56
C1—C10—C9	109.49 (16)	C14—C15—H15A	110.94
C1—C10—C19	108.28 (16)	C14—C15—H15B	110.94
C5—C10—C9	108.70 (14)	C16—C15—H15A	110.96
C5—C10—C19	107.25 (16)	C16—C15—H15B	111.00
C9—C10—C19	112.17 (15)	H15A—C15—H15B	108.95
C1—C10—C5	110.95 (15)	C15—C16—H16A	110.53
C9—C11—C12	112.33 (15)	C15—C16—H16B	110.57
C11—C12—C13	112.15 (16)	C17—C16—H16A	110.55
C12—C13—C17	116.05 (16)	C17—C16—H16B	110.53
C12—C13—C18	111.02 (16)	H16A—C16—H16B	108.69
C12—C13—C14	108.92 (14)	C1—C22—H18A	117.65
C14—C13—C18	111.68 (16)	C1—C22—H18B	117.72
C17—C13—C18	109.97 (15)	C2—C22—H18A	117.69
C14—C13—C17	98.61 (14)	C2—C22—H18B	117.71
C8—C14—C15	120.43 (16)	H18A—C22—H18B	114.82
C13—C14—C15	104.22 (14)	C10—C19—H19A	109.45
C8—C14—C13	111.65 (14)	C10—C19—H19B	109.46
C14—C15—C16	104.01 (15)	C10—C19—H19C	109.47
C15—C16—C17	105.97 (16)	H19A—C19—H19B	109.49
O24—C17—C16	111.07 (15)	H19A—C19—H19C	109.49
O24—C17—C20	100.78 (16)	H19B—C19—H19C	109.46
O24—C17—C13	111.00 (14)	C13—C18—H20A	109.45
C13—C17—C20	116.03 (16)	C13—C18—H20B	109.49
C16—C17—C20	115.00 (16)	C13—C18—H20C	109.43
C13—C17—C16	103.21 (15)	H20A—C18—H20B	109.45
C1—C22—C2	60.74 (15)	H20A—C18—H20C	109.58
O23—C20—C21	120.8 (2)	H20B—C18—H20C	109.42
C17—C20—C21	116.7 (2)	C20—C21—H22A	109.47
O23—C20—C17	122.4 (2)	C20—C21—H22B	109.47
C2—C1—H1	114.7 (19)	C20—C21—H22C	109.43
C10—C1—H1	111.5 (18)	H22A—C21—H22B	109.46
C22—C1—H1	119.2 (18)	H22A—C21—H22C	109.44
C1—C2—H2	118.7 (15)	H22B—C21—H22C	109.57
C3—C2—H2	113.7 (17)

C10—C1—C2—C3	−4.8 (3)	C14—C8—C9—C10	172.23 (14)
C10—C1—C2—C22	−112.1 (2)	C8—C9—C10—C1	−179.24 (15)
C2—C1—C10—C19	−92.1 (2)	C11—C9—C10—C5	175.28 (16)
C22—C1—C10—C5	−47.2 (3)	C11—C9—C10—C19	−66.3 (2)
C22—C1—C10—C9	72.8 (2)	C8—C9—C11—C12	55.2 (2)
C22—C1—C10—C19	−164.6 (2)	C10—C9—C11—C12	−177.42 (16)
C10—C1—C22—C2	109.1 (2)	C8—C9—C10—C5	−57.89 (19)
C22—C1—C2—C3	107.3 (2)	C8—C9—C10—C19	60.53 (19)
C2—C1—C10—C5	25.4 (3)	C11—C9—C10—C1	53.9 (2)
C2—C1—C10—C9	145.33 (19)	C9—C11—C12—C13	−52.8 (2)
C22—C2—C3—C4	49.1 (3)	C11—C12—C13—C17	163.75 (15)
C3—C2—C22—C1	−107.4 (2)	C11—C12—C13—C18	−69.7 (2)
C1—C2—C3—C4	−17.9 (3)	C11—C12—C13—C14	53.7 (2)
C22—C2—C3—O25	−130.5 (3)	C12—C13—C14—C15	168.70 (15)
C1—C2—C3—O25	162.6 (2)	C18—C13—C14—C8	63.2 (2)
O25—C3—C4—C5	−161.6 (2)	C17—C13—C14—C8	178.79 (14)
C2—C3—C4—C5	18.9 (4)	C17—C13—C14—C15	47.28 (17)
C3—C4—C5—C10	4.7 (3)	C12—C13—C14—C8	−59.79 (19)
C3—C4—C5—C6	179.4 (2)	C12—C13—C17—C20	72.2 (2)
C10—C5—C6—C7	−9.7 (3)	C14—C13—C17—O24	74.04 (17)
C4—C5—C10—C1	−26.1 (3)	C14—C13—C17—C16	−45.02 (16)
C10—C5—C6—Cl26	168.95 (14)	C14—C13—C17—C20	−171.72 (16)
C4—C5—C10—C19	91.9 (2)	C18—C13—C14—C15	−68.31 (19)
C6—C5—C10—C1	158.92 (17)	C12—C13—C17—O24	−42.0 (2)
C4—C5—C10—C9	−146.6 (2)	C12—C13—C17—C16	−161.06 (15)
C6—C5—C10—C19	−83.01 (19)	C18—C13—C17—C20	−54.8 (2)
C4—C5—C6—Cl26	−6.1 (3)	C18—C13—C17—O24	−169.05 (16)
C6—C5—C10—C9	38.5 (2)	C18—C13—C17—C16	71.89 (18)
C4—C5—C6—C7	175.3 (2)	C13—C14—C15—C16	−31.17 (19)
C5—C6—C7—C8	−1.7 (3)	C8—C14—C15—C16	−157.35 (15)
Cl26—C6—C7—C8	179.69 (15)	C14—C15—C16—C17	2.30 (19)
C6—C7—C8—C9	−17.8 (3)	C15—C16—C17—O24	−91.94 (18)
C6—C7—C8—C14	−139.23 (19)	C15—C16—C17—C13	27.08 (18)
C7—C8—C9—C10	47.7 (2)	C15—C16—C17—C20	154.44 (17)
C7—C8—C14—C13	−174.16 (15)	C13—C17—C20—O23	−16.7 (3)
C7—C8—C14—C15	−51.5 (2)	C16—C17—C20—O23	−137.3 (2)
C9—C8—C14—C13	62.31 (18)	C16—C17—C20—C21	46.3 (3)
C9—C8—C14—C15	−175.03 (15)	C13—C17—C20—C21	166.9 (2)
C14—C8—C9—C11	−58.73 (19)	O24—C17—C20—O23	103.2 (3)
C7—C8—C9—C11	176.69 (16)	O24—C17—C20—C21	−73.2 (3)

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2; (v) x−1, y, z; (vi) −x+1/2, −y+1, z−1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) x−1/2, −y+3/2, −z; (ix) x+1, y, z; (x) −x−1/2, −y+1, z+1/2; (xi) x+1/2, −y+3/2, −z; (xii) −x−1/2, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O24—H2A···O25	0.81 (3)	2.01 (3)	2.804 (3)	169 (3)
C4—H4···Cl26	0.93	2.54	2.994 (2)	111
C12—H12B···O24	0.97	2.48	2.905 (2)	106
C14—H14···O24	0.98	2.49	2.876 (2)	103
C15—H15B···O24	0.97	2.49	3.394 (2)	156
C22—H20A···O23	0.96	2.46	3.042 (3)	119

Deviations (Å) of the steroid nucleus from the plane defined by atoms C3, C4, C5, C6, C7 and Cl1 top

Name	CPA	CPH
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 A	φA–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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