#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200005.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2200005
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2005
_journal_volume  61
_journal_page_first  o3576
_journal_page_last  o3578
_publ_section_title
;
Comparison of the structures of cyproterone and its acetate ester
;
loop_
_publ_author_name
  'de Ruyck, J\'er\^ome'
  'Henry de Hassonville, Sandrine'
  'Li\'egeois, Jean-Fran\,cois'
  'Wouters, Johan'
_chemical_name_common  'Cyproterone'
_chemical_formula_moiety  'C22 H27 Cl O3'
_chemical_formula_sum  'C22 H27 Cl O3'
_chemical_formula_iupac  'C22 H27 Cl O3'
_chemical_formula_weight  374.89
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  1/2-x,-y,1/2+z
  1/2+x,1/2-y,-z
  -x,1/2+y,1/2-z
_cell_length_a  6.3880(10)
_cell_length_b  14.182(2)
_cell_length_c  21.107(3)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1912.2(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.302
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
  Cl26 0.48194(14) 0.48070(4) 0.28454(3) 0.0713(2) Uani . . 1.000 Cl
  O25 0.3435(4) 0.80973(14) 0.36536(9) 0.0646(6) Uani . . 1.000 O
  O24 -0.3669(2) 0.44701(11) 0.03931(7) 0.0391(4) Uani . . 1.000 O
  O23 -0.3042(4) 0.55099(13) -0.08865(8) 0.0614(6) Uani . . 1.000 O
  C1 0.0888(4) 0.78601(14) 0.20969(10) 0.0383(6) Uani . . 1.000 C
  C2 0.1229(4) 0.82428(16) 0.27615(10) 0.0452(6) Uani . . 1.000 C
  C3 0.2678(4) 0.77456(16) 0.31753(10) 0.0435(7) Uani . . 1.000 C
  C4 0.3216(4) 0.67770(16) 0.30028(10) 0.0404(6) Uani . . 1.000 C
  C5 0.2934(3) 0.64242(13) 0.24162(9) 0.0324(5) Uani . . 1.000 C
  C6 0.3511(3) 0.54523(14) 0.22582(10) 0.0379(5) Uani . . 1.000 C
  C7 0.3147(3) 0.50450(13) 0.17050(10) 0.0358(5) Uani . . 1.000 C
  C8 0.2035(3) 0.55381(12) 0.11785(8) 0.0285(5) Uani . . 1.000 C
  C9 0.0817(3) 0.64021(12) 0.14219(8) 0.0287(4) Uani . . 1.000 C
  C10 0.2178(3) 0.70241(12) 0.18632(8) 0.0303(5) Uani . . 1.000 C
  C11 -0.0211(4) 0.69331(13) 0.08672(9) 0.0373(5) Uani . . 1.000 C
  C12 -0.1611(3) 0.62932(13) 0.04663(9) 0.0356(5) Uani . . 1.000 C
  C13 -0.0463(3) 0.54051(13) 0.02449(8) 0.0285(4) Uani . . 1.000 C
  C14 0.0488(3) 0.49035(12) 0.08275(8) 0.0280(4) Uani . . 1.000 C
  C15 0.1185(3) 0.39401(13) 0.05732(10) 0.0362(6) Uani . . 1.000 C
  C16 -0.0408(3) 0.37218(15) 0.00384(10) 0.0394(5) Uani . . 1.000 C
  C17 -0.1864(3) 0.45895(13) -0.00009(8) 0.0320(5) Uani . . 1.000 C
  C22 -0.0794(4) 0.77461(18) 0.25735(11) 0.0474(7) Uani . . 1.000 C
  C19 0.4133(4) 0.74080(15) 0.15244(10) 0.0418(6) Uani . . 1.000 C
  C18 0.1223(4) 0.56476(17) -0.02521(9) 0.0406(6) Uani . . 1.000 C
  C20 -0.2902(4) 0.47460(17) -0.06495(9) 0.0412(6) Uani . . 1.000 C
  C21 -0.3858(6) 0.3901(2) -0.09594(14) 0.0668(10) Uani . . 1.000 C
  H1 0.076(4) 0.828(2) 0.1811(13) 0.049(7) Uiso . . 1.000 H
  H2 0.122(5) 0.8912(19) 0.2824(12) 0.052(7) Uiso . . 1.000 H
  H2A -0.345(5) 0.406(2) 0.0649(15) 0.059(9) Uiso . . 1.000 H
  H4 0.37780 0.63860 0.33130 0.0480 Uiso calc R 1.000 H
  H7 0.36000 0.44290 0.16420 0.0430 Uiso calc R 1.000 H
  H8 0.30850 0.57580 0.08740 0.0340 Uiso calc R 1.000 H
  H9 -0.03290 0.61570 0.16830 0.0340 Uiso calc R 1.000 H
  H11A -0.10420 0.74490 0.10330 0.0450 Uiso calc R 1.000 H
  H11B 0.08740 0.72000 0.06000 0.0450 Uiso calc R 1.000 H
  H12A -0.21000 0.66410 0.00990 0.0430 Uiso calc R 1.000 H
  H12B -0.28260 0.61110 0.07130 0.0430 Uiso calc R 1.000 H
  H14 -0.06720 0.47830 0.11210 0.0340 Uiso calc R 1.000 H
  H15A 0.11260 0.34640 0.09030 0.0430 Uiso calc R 1.000 H
  H15B 0.25990 0.39700 0.04080 0.0430 Uiso calc R 1.000 H
  H16A 0.03100 0.36250 -0.03610 0.0470 Uiso calc R 1.000 H
  H16B -0.12060 0.31590 0.01380 0.0470 Uiso calc R 1.000 H
  H18A -0.10370 0.71190 0.27410 0.0570 Uiso calc R 1.000 H
  H18B -0.20420 0.81290 0.25260 0.0570 Uiso calc R 1.000 H
  H19A 0.48810 0.78210 0.18050 0.0630 Uiso calc R 1.000 H
  H19B 0.37160 0.77500 0.11530 0.0630 Uiso calc R 1.000 H
  H19C 0.50220 0.68920 0.14040 0.0630 Uiso calc R 1.000 H
  H20A 0.05760 0.59460 -0.06100 0.0610 Uiso calc R 1.000 H
  H20B 0.19090 0.50800 -0.03870 0.0610 Uiso calc R 1.000 H
  H20C 0.22340 0.60670 -0.00680 0.0610 Uiso calc R 1.000 H
  H22A -0.46560 0.40970 -0.13220 0.1000 Uiso calc R 1.000 H
  H22B -0.47610 0.35870 -0.06640 0.1000 Uiso calc R 1.000 H
  H22C -0.27700 0.34780 -0.10920 0.1000 Uiso calc R 1.000 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Cl26 C6 . . 1.753(2) no
  O25 C3 . . 1.226(3) no
  O24 C17 . . 1.432(2) no
  O23 C20 . . 1.197(3) no
  O24 H2A . . 0.81(3) no
  C1 C2 . . 1.520(3) no
  C1 C22 . . 1.481(3) no
  C1 C10 . . 1.526(3) no
  C2 C3 . . 1.455(3) no
  C2 C22 . . 1.524(4) no
  C3 C4 . . 1.462(3) no
  C4 C5 . . 1.348(3) no
  C5 C6 . . 1.465(3) no
  C5 C10 . . 1.523(3) no
  C6 C7 . . 1.323(3) no
  C7 C8 . . 1.493(3) no
  C8 C14 . . 1.528(3) no
  C8 C9 . . 1.540(2) no
  C9 C11 . . 1.539(3) no
  C9 C10 . . 1.550(3) no
  C10 C19 . . 1.539(3) no
  C11 C12 . . 1.530(3) no
  C12 C13 . . 1.531(3) no
  C13 C14 . . 1.545(2) no
  C13 C18 . . 1.542(3) no
  C13 C17 . . 1.552(3) no
  C14 C15 . . 1.534(3) no
  C15 C16 . . 1.551(3) no
  C16 C17 . . 1.545(3) no
  C17 C20 . . 1.537(3) no
  C20 C21 . . 1.496(4) no
  C1 H1 . . 0.85(3) no
  C2 H2 . . 0.96(3) no
  C4 H4 . . 0.9301 no
  C7 H7 . . 0.9298 no
  C8 H8 . . 0.9799 no
  C9 H9 . . 0.9800 no
  C11 H11A . . 0.9693 no
  C11 H11B . . 0.9704 no
  C12 H12A . . 0.9705 no
  C12 H12B . . 0.9697 no
  C14 H14 . . 0.9808 no
  C15 H15A . . 0.9705 no
  C15 H15B . . 0.9692 no
  C16 H16A . . 0.9695 no
  C16 H16B . . 0.9701 no
  C22 H18A . . 0.9696 no
  C22 H18B . . 0.9698 no
  C19 H19A . . 0.9603 no
  C19 H19B . . 0.9595 no
  C19 H19C . . 0.9605 no
  C18 H20A . . 0.9595 no
  C18 H20B . . 0.9597 no
  C18 H20C . . 0.9601 no
  C21 H22A . . 0.9607 no
  C21 H22B . . 0.9591 no
  C21 H22C . . 0.9598 no