Enantioselective Cyanoborylation of Allenes by N-Heterocyclic Carbene-Copper Catalysts
Li, Zhenghua; Zhang, Liang; Nishiura, Masayoshi; Luo, Gen; Luo, Yi; Hou, Zhaomin; ACS Catalysis  (2020) 11685–11692; doi:10.1021/acscatal.0c03018

data_4518108
_publ_section_title
;
 Enantioselective Cyanoborylation of Allenes by N-Heterocyclic
 Carbene-Copper Catalysts
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11685
_journal_page_last               11692
_journal_paper_doi               10.1021/acscatal.0c03018
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H18 Br N'
_chemical_formula_sum            'C14 H18 Br N'
_chemical_formula_weight         280.20
_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-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4796(2)
_cell_length_b                   10.8112(4)
_cell_length_c                   17.4816(6)
_cell_measurement_reflns_used    240
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1224.63(7)
_computing_cell_refinement       'Bruker SMART APEX3 v2016.1-0'
_computing_data_collection       'Bruker SMART APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SMART APEX3 v2016.1-0'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest with CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10435
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    3.329
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.027(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0254P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0567
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2055
_reflns_number_total             2154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03018_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4518108
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.298
_shelx_estimated_absorpt_t_max   0.635
_shelx_res_checksum              93098
_shelx_hkl_checksum              18881