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_4516149
_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            'C26 H28 F N O S'
_chemical_formula_weight         421.55
_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            4
_cell_length_a                   7.212(4)
_cell_length_b                   8.116(4)
_cell_length_c                   36.696(17)
_cell_measurement_reflns_used    6754
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.22
_cell_volume                     2147.9(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0571
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            20296
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_min         2.220
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6156
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0590
_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^)+(0.0489P)^2^+1.3193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4440
_reflns_number_total             5683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02840_si_004.cif
_cod_data_source_block           k93k
_cod_original_cell_volume        2147.8(18)
_cod_database_code               4516149
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.949
_shelx_res_checksum              38648
_shelx_hkl_checksum              83589