Palladium-Catalyzed Negishi Coupling of α-CF<sub>3</sub> Oxiranyl Zincate: Access to Chiral CF<sub>3</sub>-Substituted Benzylic Tertiary Alcohols.
Zhang, Hu; Buchwald, Stephen L.; Journal of the American Chemical Society 139 (2017) 11590–11594; doi:10.1021/jacs.7b06630

data_4131536
_publ_section_title
;
 Palladium-Catalyzed Negishi Coupling of \a-CF<sub>3</sub> Oxiranyl
 Zincate: Access to Chiral CF<sub>3</sub>-Substituted Benzylic Tertiary
 Alcohols.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11590
_journal_page_last               11594
_journal_paper_doi               10.1021/jacs.7b06630
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H9 F3 O S'
_chemical_formula_weight         234.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.017(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1870(13)
_cell_length_b                   5.4348(8)
_cell_length_c                   11.5306(18)
_cell_measurement_reflns_used    5204
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.51
_cell_volume                     508.04(14)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8816
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.567
_diffrn_reflns_theta_min         1.784
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1152 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0394P)^2^+0.0720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2732
_reflns_number_total             2825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06630_si_001.cif
_cod_data_source_block           x17088
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131536
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              52942
_shelx_hkl_checksum              19645