Structure–activity relationships in 4- and 5-androstene: 3β-acetoxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-carbonitrile and 17-methyl-3,17-dioxo-16,17-seco-4-androstene-16-carbonitrile
Lazar, Dušan; Klisurić, Olivera; Stanković, Slobodanka; Penov-Gaši, Katarina; Djurendić, Evgenija; Kovačević, Radmila; Acta Crystallographica Section C 60 (2004) o671–o673; doi:10.1107/S0108270104017457

data_2014155
_publ_section_title
;
 Structure--activity relationships in 4- and 5-androstene:
 3\b-acetoxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-carbonitrile
 and 17-methyl-3,17-dioxo-16,17-seco-4-androstene-16-carbonitrile
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o671
_journal_page_last               o673
_journal_paper_doi               10.1107/S0108270104017457
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H31 N O3'
_chemical_formula_moiety         'C22 H31 N O3'
_chemical_formula_sum            'C22 H31 N O3'
_chemical_formula_weight         357.48
_chemical_name_systematic
;
3\b-acetoxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-carbonitrile
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.946(2)
_cell_length_b                   16.120(2)
_cell_length_c                   20.746(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.87
_cell_measurement_theta_min      15.02
_cell_volume                     1988.5(8)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics
'ORTEP-3 for Windows, Version 1.074 (Farrugia, 1997)'
_computing_publication_material  'CSU (Vickovi\'c, 1988)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6350
_diffrn_reflns_theta_full        74.65
_diffrn_reflns_theta_max         74.65
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.169
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0734P)^2^+0.1452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                1621
_reflns_number_total             2354
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ga1054.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               2014155
_cod_database_fobs_code          2014155