Catalytic Enantioselective Boryl and Silyl Substitution with Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F β-Elimination.
Paioti, Paulo H. S.; Del Pozo, Juan; Mikus, Malte S.; Lee, Jaehee; Koh, Ming Joo; Romiti, Filippo; Torker, Sebastian; Hoveyda, Amir H.; Journal of the American Chemical Society 141 (2019) 19917–19934; doi:10.1021/jacs.9b11382

data_4133904
_publ_section_title
;
 Catalytic Enantioselective Boryl and Silyl Substitution with
 Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F
 \b-Elimination.
;
_journal_issue                   50
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19917
_journal_page_last               19934
_journal_paper_doi               10.1021/jacs.9b11382
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 B F2 O2'
_chemical_formula_sum            'C17 H23 B F2 O2'
_chemical_formula_weight         308.16
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                102.2931(18)
_cell_angle_beta                 95.7488(19)
_cell_angle_gamma                104.3562(19)
_cell_formula_units_Z            2
_cell_length_a                   8.4140(4)
_cell_length_b                   8.8842(4)
_cell_length_c                   11.9257(6)
_cell_measurement_reflns_used    9006
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.80
_cell_measurement_theta_min      4.30
_cell_volume                     832.74(7)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11546
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.308
_diffrn_reflns_theta_min         5.303
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2016). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2597 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5804
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0560
_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
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.2627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                5702
_reflns_number_total             5804
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b11382_si_003.cif
_cod_data_source_block           C17H23BF2O2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4133904
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.739
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              8827
_shelx_hkl_checksum              23587