Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents.
Okolo, ChrisTina; Ali, Mohamad Akbar; Newman, Matthew; Chambers, Steven A.; Whitt, Jedidiah; Alsharif, Zakeyah A.; Day, Victor W.; Alam, Mohammad A.; ACS omega 3 (2018) 17991–18001; doi:10.1021/acsomega.8b02840

data_4516148
_publ_section_title
;
 Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of
 Thiazolo-androstenones: Potent Anticancer Agents.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              17991
_journal_page_last               18001
_journal_paper_doi               10.1021/acsomega.8b02840
_journal_volume                  3
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H32 F N O2 S'
_chemical_formula_weight         465.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.79(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.190(8)
_cell_length_b                   6.636(5)
_cell_length_c                   18.242(14)
_cell_measurement_reflns_used    898
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.68
_cell_volume                     1192.7(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15271
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.571
_diffrn_reflns_theta_min         2.067
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.320
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 2248 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         7639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.2519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                6135
_reflns_number_total             7639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02840_si_003.cif
_cod_data_source_block           k92k
_cod_original_cell_volume        1192.6(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4516148
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.905
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              43234
_shelx_hkl_checksum              54540