Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented Synthesis.
Sun, Yu; Zhou, Yuebiao; Shi, Ying; Del Pozo, Juan; Torker, Sebastian; Hoveyda, Amir H.; Journal of the American Chemical Society 141 (2019) 12087–12099; doi:10.1021/jacs.9b05465

data_4128546
_publ_section_title
;
 Copper-Hydride-Catalyzed Enantioselective Processes with Allenyl
 Boronates. Mechanistic Nuances, Scope, and Utility in Target-Oriented
 Synthesis.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12087
_journal_page_last               12099
_journal_paper_doi               10.1021/jacs.9b05465
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 B F3 O2'
_chemical_formula_sum            'C21 H28 B F3 O2'
_chemical_formula_weight         380.24
_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                95.475(2)
_cell_angle_beta                 98.967(2)
_cell_angle_gamma                106.855(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7306(3)
_cell_length_b                   9.6620(5)
_cell_length_c                   16.8578(8)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.64
_cell_measurement_theta_min      2.68
_cell_volume                     1024.84(9)
_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 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0234
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19183
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        66.717
_diffrn_reflns_theta_max         66.717
_diffrn_reflns_theta_min         2.683
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6605
_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    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         6823
_refine_ls_number_restraints     617
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.3679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                6691
_reflns_number_total             6823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05465_si_003.cif
_cod_data_source_block           C21H28BF3O2
_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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4128546
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.713
_shelx_estimated_absorpt_t_max   0.925
_shelx_res_checksum              25047
_shelx_hkl_checksum              13382