Improved Synthesis of β-Aminoboronate Esters via Copper-Catalyzed Diastereo- and Enantioselective Addition of 1,1-Diborylalkanes to Acyclic Arylaldimines
Kim, Jeongho; Hwang, Chiwon; Kim, Youngmin; Cho, Seung Hwan; Organic Process Research & Development 23 (2019) 1663–; doi:10.1021/acs.oprd.9b00179

data_1554187
_publ_section_title
;
 Improved Synthesis of \b-Aminoboronate Esters via Copper-Catalyzed
 Diastereo- and Enantioselective Addition of 1,1-Diborylalkanes to Acyclic
 Arylaldimines
;
_journal_issue                   8
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1663
_journal_paper_doi               10.1021/acs.oprd.9b00179
_journal_volume                  23
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_sum            'C24 H35 B N2 O4 S'
_chemical_formula_weight         458.41
_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   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 110.202(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4365(8)
_cell_length_b                   7.5623(5)
_cell_length_c                   15.4088(11)
_cell_measurement_reflns_used    27001
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.379
_cell_measurement_theta_min      3.040
_cell_volume                     1250.67(15)
_computing_cell_refinement       'Bruker APEXIll'
_computing_data_collection       'Bruker APEXIll'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26977
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.379
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6190
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0485P)^2^+0.6670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5154
_reflns_number_total             6190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op9b00179_si_002.cif
_cod_data_source_block           Mono_4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1250.66(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1554187
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              67898
_shelx_hkl_checksum              95751