Asymmetric Hydrogenation of α-Boryl Enamides Enabled by Nonbonding Interactions
Fan, Dongyang; Zhang, Jian; Hu, Yanhua; Zhang, Zhenfeng; Gridnev, Ilya D.; Zhang, Wanbin; ACS Catalysis  (2020) 3232–3240; doi:10.1021/acscatal.9b04543

data_4517436
_publ_section_title
;
 Asymmetric Hydrogenation of \a-Boryl Enamides Enabled by Nonbonding
 Interactions
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3232
_journal_page_last               3240
_journal_paper_doi               10.1021/acscatal.9b04543
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H23 B F3 N O4'
_chemical_formula_sum            'C18 H23 B F3 N O4'
_chemical_formula_weight         385.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2697(3)
_cell_length_b                   10.8812(5)
_cell_length_c                   27.9823(13)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.16
_cell_volume                     1909.00(15)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24696
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.361
_diffrn_reflns_theta_min         3.159
_exptl_absorpt_coefficient_mu    0.955
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5582
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0682P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3292
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04543_si_002.cif
_cod_data_source_block           ta_a
_cod_depositor_comments          'Adding full bibliography for 4517436.cif.'
_cod_database_code               4517436
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.832
_shelx_res_checksum              53953
_shelx_hkl_checksum              82963