Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts.
He, Zhi-Tao; Jiang, Xingyu; Hartwig, John F.; Journal of the American Chemical Society 141 (2019) 13066–13073; doi:10.1021/jacs.9b04440

data_4127850
_publ_section_title
;
 Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic
 Pairs by Allylic Substitution with Iridium and Copper Catalysts.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13066
_journal_page_last               13073
_journal_paper_doi               10.1021/jacs.9b04440
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H16 F N O2 S'
_chemical_formula_sum            'C19 H16 F N O2 S'
_chemical_formula_weight         341.39
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 107.8166(7)
_cell_angle_gamma                90
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_cell_length_a                   13.63616(9)
_cell_length_b                   8.38855(5)
_cell_length_c                   15.53968(10)
_cell_measurement_reflns_used    37026
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.0160
_cell_measurement_theta_min      3.3960
_cell_volume                     1692.30(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         2.987
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 3129 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6883
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.3409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6845
_reflns_number_total             6883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04440_si_003.cif
_cod_data_source_block           ent-7g
_cod_original_cell_volume        1692.297(19)
_cod_database_code               4127850
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.630
_shelx_estimated_absorpt_t_max   0.849
_shelx_res_checksum              73086
_shelx_hkl_checksum              3359