Two androsterone derivatives as inhibitors of androgen biosynthesis
Djigoue, Guy-Bertrand; Simard, Michel; Kenmogne, Lucie-Carolle; Poirier, Donald; Acta Crystallographica Section C 68 (2012) o231–o234; doi:10.1107/S0108270112021099

data_2018492
_publ_section_title
;
 Two androsterone derivatives as inhibitors of androgen biosynthesis
;
_journal_coeditor_code           FA3273
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o231
_journal_page_last               o234
_journal_paper_doi               10.1107/S0108270112021099
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C26 H41 N O3'
_chemical_formula_moiety         'C26 H41 N O3'
_chemical_formula_sum            'C26 H41 N O3'
_chemical_formula_weight         415.60
_chemical_name_systematic
;
(3<i>R</i>,5<i>S</i>,5'<i>R</i>,8<i>R</i>,9<i>S</i>,10<i>S</i>,13<i>S</i>,
14<i>S</i>)-10,13-dimethyl-5'-(2-methylpropyl)tetradecahydro-6'<i>H</i>-
spiro[cyclopenta[<i>a</i>]phenanthrene-3,2'-[1,4]oxazinane]-6',17(2<i>H</i>)-
dione
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 107.3095(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.07929(17)
_cell_length_b                   5.82873(8)
_cell_length_c                   16.3140(2)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.29
_cell_measurement_theta_min      2.84
_cell_volume                     1187.38(3)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 [or SMART?] (Bruker, 2011)'
_computing_data_reduction        'XPREP (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36176
_diffrn_reflns_theta_full        72.51
_diffrn_reflns_theta_max         72.51
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.8095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.221
_refine_ls_abs_structure_details 'Flack (1983), 1733 Friedel pairs'
_refine_ls_abs_structure_Flack   0.12(18)
_refine_ls_extinction_coef       0.0046(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+0.0832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                4159
_reflns_number_total             4334
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3273.cif
_cod_data_source_block           I
_cod_original_cell_volume        1187.37(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2018492
_cod_database_fobs_code          2018492