Highly regio- and stereocontrolled preparation of α-(trifluoromethyl)-β-(phenylthio) enamines by the hydroamination of <i>in situ</i>-synthesized 1-(trifluoromethyl)-2-(phenylthio)ethyne.
Koga, Akihiro; Matsuda, Maki; Tanaka, Rin; Endo, Minami; Yamada, Yasunori; Hanamoto, Takeshi; Organic & biomolecular chemistry 21 (2023) 8528–8534; doi:10.1039/d3ob01473h

data_7159592
_publ_section_title
;
 Highly regio- and stereocontrolled preparation of
 &#x3b1;-(trifluoromethyl)-&#x3b2;-(phenylthio) enamines by the
 hydroamination of <i>in situ</i>-synthesized
 1-(trifluoromethyl)-2-(phenylthio)ethyne.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8528
_journal_page_last               8534
_journal_paper_doi               10.1039/d3ob01473h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H18 F6 O S2'
_chemical_formula_sum            'C23 H18 F6 O S2'
_chemical_formula_weight         488.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                89.510(5)
_cell_angle_beta                 83.259(4)
_cell_angle_gamma                86.852(4)
_cell_formula_units_Z            4
_cell_length_a                   9.7989(14)
_cell_length_b                   15.076(2)
_cell_length_c                   15.426(2)
_cell_measurement_reflns_used    8200
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     2259.7(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32623
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.013
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.82
_refine_diff_density_min         -0.81
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.3260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7702
_reflns_number_total             9840
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3ob01473h2.cif
_cod_data_source_block           191126a
_cod_depositor_comments
;
        Adding full bibliography for 7159592.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H36 F12 O2 S4'
_cod_original_formula_weight         977.01
_cod_original_formula_moiety         'C46 H36 F12 O2 S4'
_cod_original_formula_units_Z            2
_cod_database_code               7159592
_shelx_res_checksum              55356
_shelx_hkl_checksum              58425