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_2018493
_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          'C28 H43 N O5'
_chemical_formula_moiety         'C28 H43 N O5'
_chemical_formula_sum            'C28 H43 N O5'
_chemical_formula_weight         473.63
_chemical_name_systematic
;
methyl
(2<i>R</i>)-2-[(3<i>R</i>,5<i>S</i>,8<i>R</i>,9<i>S</i>,10<i>S</i>,
13<i>S</i>,14<i>S</i>)-10,13-dimethyl-2',17-dioxohexadecahydro-3'<i>H</i>-
spiro[cyclopenta[<i>a</i>]phenanthrene-3,5'-[1,3]oxazolidin-3'-yl]]-
4-methylpentanoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3941(2)
_cell_length_b                   18.1440(7)
_cell_length_c                   22.6047(9)
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.47
_cell_measurement_theta_min      3.12
_cell_volume                     2622.47(17)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (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 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Microstar'
_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  0.052
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            43157
_diffrn_reflns_theta_full        69.69
_diffrn_reflns_theta_max         69.69
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.7867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.143
_refine_ls_abs_structure_details 'Flack (1983), 2087 Friedel pairs'
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0555P)^2^+0.4002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                4697
_reflns_number_total             4933
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3273.cif
_cod_data_source_block           II
_cod_database_code               2018493
_cod_database_fobs_code          2018493