#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008951.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_2008951
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
N-tert-Butyl-3-oxo-4-aza-5\b,17\b-androstane-17-carboxamide methanol solvate,
a finasteride impurity
;
loop_
_publ_author_name
  'Moses Babu,,J.'
  'Ravindra Kumar, Y.'
  'Vyas, K.'
  'Om Reddy, G.'
  'Rajan, S. T.'
  'Reddy, M. S. N. '
_chemical_formula_moiety  'C23 H38 N2 O2, C1 H4 O1'
_chemical_formula_sum  'C24 H42 N2 O3'
_chemical_formula_iupac  'C23 H38 N2 O2, C1 H4 O1'
_chemical_formula_weight  406.61
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
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  11.607(2)
_cell_length_b  20.097(5)
_cell_length_c  10.449(4)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2437.5(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  298.2
_exptl_crystal_density_diffrn  1.108
_diffrn_ambient_temperature  298.2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  O1 0.4600(4) 0.6252(2) 0.9962(4) 0.1000(10)
  Uani d ? . 1.000
  O2 0.8433(3) 1.0496(2) 0.6894(5) 0.1170(10)
  Uani d ? . 1.000
  O3 0.1606(4) 0.6764(2) 0.9054(5) 0.127(2) Uani d ? D 1.000
  N1 0.4038(3) 0.6812(2) 0.8250(4) 0.0638(9) Uani d ? . 1.000
  N2 0.9501(3) 0.9767(2) 0.8012(4) 0.0668(9) Uani d ? . 1.000
  C1 0.4808(4) 0.6452(2) 0.8886(5) 0.0680(10)
  Uani d ? . 1.000
  C2 0.5935(4) 0.6314(2) 0.8198(5) 0.0750(10)
  Uani d ? . 1.000
  C3 0.5934(3) 0.6463(2) 0.6796(5) 0.0690(10)
  Uani d ? . 1.000
  C4 0.5334(3) 0.7123(2) 0.6453(4) 0.0577(8) Uani d ? . 1.000
  C5 0.4101(3) 0.7057(2) 0.6917(4) 0.0628(9) Uani d ? . 1.000
  C6 0.3418(3) 0.7690(2) 0.6814(5) 0.0690(10)
  Uani d ? . 1.000
  C7 0.4009(3) 0.8267(2) 0.7458(4) 0.0590(10)
  Uani d ? . 1.000
  C8 0.5244(3) 0.8370(2) 0.6958(3) 0.0470(8) Uani d ? . 1.000
  C9 0.5920(3) 0.77200(10)
  0.7129(3) 0.0472(8) Uani d ? . 1.000
  C10 0.7200(3) 0.7806(2) 0.6786(4) 0.0559(9) Uani d ? . 1.000
  C11 0.7776(3) 0.8396(2) 0.7454(3) 0.0501(8) Uani d ? . 1.000
  C12 0.7116(3) 0.90320(10)
  0.7184(3) 0.0471(7) Uani d ? . 1.000
  C13 0.5850(3) 0.89200(10)
  0.7635(3) 0.0466(8) Uani d ? . 1.000
  C14 0.5343(3) 0.9632(2) 0.7598(4) 0.0660(10)
  Uani d ? . 1.000
  C15 0.6349(4) 1.0074(2) 0.8008(5) 0.0770(10)
  Uani d ? . 1.000
  C16 0.7434(3) 0.9641(2) 0.8036(4) 0.0575(9) Uani d ? . 1.000
  C17 0.7178(4) 0.9212(2) 0.5765(4) 0.0710(10)
  Uani d ? . 1.000
  C18 0.5355(4) 0.7191(2) 0.5001(4) 0.0770(10)
  Uani d ? . 1.000
  C19 0.8495(4) 1.0014(2) 0.7609(4) 0.0660(10)
  Uani d ? . 1.000
  C20 1.0655(4) 1.0047(3) 0.7687(5) 0.0870(10)
  Uani d ? . 1.000
  C21 1.1511(5) 0.9607(5) 0.8330(10)
  0.178(4) Uani d ? . 1.000
  C22 1.0808(6) 1.0085(5) 0.6229(6) 0.142(2) Uani d ? . 1.000
  C23 1.0728(5) 1.0756(3) 0.8214(9) 0.136(3) Uani d ? . 1.000
  C24 0.0592(7) 0.7164(5) 0.8830(10)
  0.191(4) Uani d ? D 1.000
  H1 0.3374 0.6937 0.8716 0.075 Uiso c ? . 1.000
  H2 0.6129 0.5859 0.8325 0.091 Uiso c ? . 1.000
  H3 0.6525 0.6581 0.8605 0.091 Uiso c ? . 1.000
  H4 0.5563 0.6110 0.6380 0.084 Uiso c ? . 1.000
  H5 0.6720 0.6488 0.6524 0.084 Uiso c ? . 1.000
  H6 0.3741 0.6736 0.6396 0.075 Uiso c ? . 1.000
  H7 0.2691 0.7625 0.7190 0.081 Uiso c ? . 1.000
  H8 0.3329 0.7793 0.5926 0.081 Uiso c ? . 1.000
  H9 0.4048 0.8180 0.8353 0.071 Uiso c ? . 1.000
  H10 0.3584 0.8659 0.7309 0.071 Uiso c ? . 1.000
  H11 0.5202 0.8470 0.6076 0.057 Uiso c ? . 1.000
  H12 0.5900 0.7621 0.8026 0.056 Uiso c ? . 1.000
  H13 0.7596 0.7412 0.7031 0.067 Uiso c ? . 1.000
  H14 0.7255 0.7869 0.5896 0.067 Uiso c ? . 1.000
  H15 0.7784 0.8317 0.8353 0.061 Uiso c ? . 1.000
  H16 0.8537 0.8438 0.7149 0.061 Uiso c ? . 1.000
  H17 0.5895 0.8795 0.8520 0.056 Uiso c ? . 1.000
  H18 0.4717 0.9674 0.8179 0.078 Uiso c ? . 1.000
  H19 0.5094 0.9741 0.6760 0.078 Uiso c ? . 1.000
  H20 0.6213 1.0252 0.8834 0.093 Uiso c ? . 1.000
  H21 0.6450 1.0426 0.7412 0.093 Uiso c ? . 1.000
  H22 0.7549 0.9489 0.8883 0.068 Uiso c ? . 1.000
  H23 0.6875 0.8853 0.5267 0.085 Uiso c ? . 1.000
  H24 0.6736 0.9600 0.5607 0.085 Uiso c ? . 1.000
  H25 0.7956 0.9286 0.5527 0.085 Uiso c ? . 1.000
  H26 0.4977 0.7608 0.4766 0.093 Uiso c ? . 1.000
  H27 0.4913 0.6841 0.4622 0.093 Uiso c ? . 1.000
  H28 0.6102 0.7193 0.4688 0.093 Uiso c ? . 1.000
  H29 0.9481 0.9379 0.8528 0.079 Uiso c ? . 1.000
  H30 1.1364 0.9595 0.9250 0.197 Uiso c ? . 1.000
  H31 1.1420 0.9154 0.8032 0.197 Uiso c ? . 1.000
  H32 1.2266 0.9746 0.8193 0.197 Uiso c ? . 1.000
  H33 1.0670 0.9678 0.5857 0.168 Uiso c ? . 1.000
  H34 1.1544 1.0255 0.6037 0.168 Uiso c ? . 1.000
  H35 1.0239 1.0409 0.5911 0.168 Uiso c ? . 1.000
  H36 1.1443 1.0949 0.7962 0.165 Uiso c ? . 1.000
  H37 1.0112 1.1012 0.7890 0.165 Uiso c ? . 1.000
  H38 1.0691 1.0746 0.9126 0.165 Uiso c ? . 1.000
  H39 -0.0011 0.6914 0.8498 0.216 Uiso c ? . 1.000
  H40 0.0349 0.7362 0.9639 0.216 Uiso c ? . 1.000
  H41 0.0780 0.7525 0.8269 0.216 Uiso c ? . 1.000
  H42 0.141(5) 0.639(2) 0.854(5) 0.120 Uiso d ? D 1.000
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
  O1 0.118(3) 0.100(2) 0.081(2) -0.002(2) 0.008(2) 0.029(2)
  O2 0.121(3) 0.082(2) 0.149(4) -0.039(2) -0.036(3) 0.065(2)
  O3 0.117(3) 0.097(2) 0.166(5) -0.023(2) 0.046(3) -0.033(3)
  N1 0.058(2) 0.072(2) 0.062(2) -0.0070(10)
  0.014(2) 0.0030(10)
  N2 0.0610(10)
  0.069(2) 0.070(2) -0.0080(10)
  0.001(2) 0.002(2)
  C1 0.069(2) 0.058(2) 0.077(2) -0.006(2) 0.003(2) 0.000(2)
  C2 0.077(2) 0.055(2) 0.093(2) 0.005(2) 0.014(2) 0.004(2)
  C3 0.064(2) 0.056(2) 0.089(2) -0.0060(10)
  0.018(2) -0.016(2)
  C4 0.061(2) 0.058(2) 0.053(2) -0.0100(10)
  -0.002(2) -0.0110(10)
  C5 0.064(2) 0.067(2) 0.058(2) -0.0160(10)
  -0.007(2) -0.010(2)
  C6 0.054(2) 0.078(2) 0.076(3) -0.0100(10)
  -0.009(2) 0.001(2)
  C7 0.0480(10)
  0.063(2) 0.066(3) 0.0040(10)
  -0.004(2) 0.005(2)
  C8 0.0500(10)
  0.0550(10)
  0.036(2) 0.0020(10)
  -0.0090(10)
  0.0000(10)
  C9 0.0490(10)
  0.0490(10)
  0.043(2) -0.0030(10)
  0.0040(10)
  -0.0040(10)
  C10 0.0520(10)
  0.057(2) 0.059(2) -0.0020(10)
  0.009(2) -0.009(2)
  C11 0.0440(10)
  0.0550(10)
  0.052(2) -0.0010(10)
  0.0070(10)
  -0.0050(10)
  C12 0.0510(10)
  0.0480(10)
  0.042(2) -0.0060(10)
  -0.0020(10)
  0.0030(10)
  C13 0.0500(10)
  0.0510(10)
  0.039(2) 0.0000(10)
  -0.0040(10)
  -0.0030(10)
  C14 0.073(2) 0.0510(10)
  0.074(3) 0.0070(10)
  -0.022(2) -0.004(2)
  C15 0.075(2) 0.056(2) 0.098(3) 0.0030(10)
  -0.023(3) -0.015(2)
  C16 0.064(2) 0.051(2) 0.057(2) -0.0070(10)
  -0.006(2) -0.005(2)
  C17 0.088(3) 0.082(2) 0.043(2) -0.024(2) 0.008(2) 0.007(2)
  C18 0.076(2) 0.098(3) 0.056(2) -0.025(2) 0.008(2) -0.023(2)
  C19 0.067(2) 0.056(2) 0.076(3) -0.0140(10)
  -0.011(2) -0.004(2)
  C20 0.073(2) 0.105(2) 0.084(3) -0.033(2) 0.016(2) -0.006(2)
  C21 0.052(2) 0.213(8) 0.270(10)
  0.024(4) 0.008(4) 0.114(8)
  C22 0.115(4) 0.223(8) 0.088(3) -0.065(5) 0.037(4) -0.022(5)
  C23 0.091(3) 0.117(4) 0.201(8) -0.037(3) 0.009(5) -0.062(5)
  C24 0.148(7) 0.202(8) 0.220(10)
  0.069(6) 0.020(8) -0.010(9)
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
  O1 C1 . . 1.219(8) no
  O2 C19 . . 1.225(7) no
  O3 C24 . . 1.445(8) no
  O3 H42 . . 0.952(9) no
  N1 C1 . . 1.328(7) no
  N1 C5 . . 1.479(8) no
  N1 H1 . . 0.95 no
  N2 C19 . . 1.337(7) no
  N2 C20 . . 1.493(7) no
  N2 H29 . . 0.95 no
  C1 C2 . . 1.518(8) no
  C2 C3 . . 1.500(10)
  no
  C2 H2 . . 0.95 no
  C2 H3 . . 0.97 no
  C3 C4 . . 1.540(7) no
  C3 H4 . . 0.94 no
  C3 H5 . . 0.96 no
  C4 C5 . . 1.517(7) no
  C4 C9 . . 1.550(6) no
  C4 C18 . . 1.523(8) no
  C5 C6 . . 1.502(8) no
  C5 H6 . . 0.94 no
  C6 C7 . . 1.506(8) no
  C6 H7 . . 0.94 no
  C6 H8 . . 0.96 no
  C7 C8 . . 1.541(7) no
  C7 H9 . . 0.95 no
  C7 H10 . . 0.94 no
  C8 C9 . . 1.534(6) no
  C8 C13 . . 1.489(6) no
  C8 H11 . . 0.94 no
  C9 C10 . . 1.538(6) no
  C9 H12 . . 0.96 no
  C10 C11 . . 1.530(7) no
  C10 H13 . . 0.95 no
  C10 H14 . . 0.94 no
  C11 C12 . . 1.518(6) no
  C11 H15 . . 0.95 no
  C11 H16 . . 0.94 no
  C12 C13 . . 1.560(6) no
  C12 C16 . . 1.557(6) no
  C12 C17 . . 1.528(7) no
  C13 C14 . . 1.546(6) no
  C13 H17 . . 0.96 no
  C14 C15 . . 1.529(8) no
  C14 H18 . . 0.95 no
  C14 H19 . . 0.95 no
  C15 C16 . . 1.531(8) no
  C15 H20 . . 0.95 no
  C15 H21 . . 0.95 no
  C16 C19 . . 1.509(7) no
  C16 H22 . . 0.95 no
  C17 H23 . . 0.96 no
  C17 H24 . . 0.95 no
  C17 H25 . . 0.95 no
  C18 H26 . . 0.98 no
  C18 H27 . . 0.96 no
  C18 H28 . . 0.93 no
  C20 C21 . . 1.490(10)
  no
  C20 C22 . . 1.540(10)
  no
  C20 C23 . . 1.530(10)
  no
  C21 H30 . . 0.98 no
  C21 H31 . . 0.97 no
  C21 H32 . . 0.93 no
  C22 H33 . . 0.92 no
  C22 H34 . . 0.94 no
  C22 H35 . . 0.99 no
  C23 H36 . . 0.95 no
  C23 H37 . . 0.94 no
  C23 H38 . . 0.95 no
  C24 H39 . . 0.93 no
  C24 H40 . . 0.98 no
  C24 H41 . . 0.96 no