Enantioselective addition of thiols to trifluoromethyl ketimines: synthesis of <i>N</i>,<i>S</i>-ketals.
Wang, Xiaonan; Gao, Yuan; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng; Organic & biomolecular chemistry 18 (2020) 7431–7436; doi:10.1039/d0ob01725f

data_7157700
_publ_section_title
;
 Enantioselective addition of thiols to trifluoromethyl ketimines:
 synthesis of <i>N</i>,<i>S</i>-ketals.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7431
_journal_page_last               7436
_journal_paper_doi               10.1039/d0ob01725f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 Cl F3 N O2 S'
_chemical_formula_sum            'C19 H19 Cl F3 N O2 S'
_chemical_formula_weight         417.9
_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_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-11-09 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                106.067(2)
_cell_angle_beta                 98.907(2)
_cell_angle_gamma                110.261(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6920(10)
_cell_length_b                   10.4626(12)
_cell_length_c                   12.9164(15)
_cell_measurement_reflns_used    2075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.886
_cell_measurement_theta_min      2.268
_cell_volume                     1017.1(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'XS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5748
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.2458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2927
_reflns_number_total             4007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01725f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
          Adding full bibliography for 7157700.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C1.9 H1.9 Cl0.1 F0.3 N0.1 O0.2 S0.1'
_cod_original_formula_sum        'C1.90 H1.90 Cl0.10 F0.30 N0.10 O0.20 S0.10'
_cod_original_formula_units_Z    20
_cod_original_formula_weight     41.79
_cod_database_code               7157700
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_olex2_submission_special_instructions 'No special instructions were received'