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_4516150
_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 syn
_chemical_formula_sum            'C26 H28 Br N O S'
_chemical_formula_weight         482.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            36
_cell_length_a                   9.5976(12)
_cell_length_b                   37.906(4)
_cell_length_c                   55.277(6)
_cell_measurement_reflns_used    9251
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.65
_cell_measurement_theta_min      2.46
_cell_volume                     20110(4)
_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 0.988
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1120
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_number            149547
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.518
_diffrn_reflns_theta_min         1.413
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    3.509
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       Plate
_exptl_crystal_F_000             9000
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_refine_diff_density_max         3.295
_refine_diff_density_min         -1.451
_refine_diff_density_rms         0.189
_refine_ls_abs_structure_details
; 
 Flack x determined using 8880 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.118(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2431
_refine_ls_number_reflns         36630
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.1354
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1346P)^2^+353.9105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3398
_refine_ls_wR_factor_ref         0.3530
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                29393
_reflns_number_total             36630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02840_si_005.cif
_cod_data_source_block           q52h
_cod_database_code               4516150
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.409
_shelx_estimated_absorpt_t_max   0.902
_shelx_res_checksum              57216
_shelx_hkl_checksum              6490