Ir-Catalyzed Atroposelective Desymmetrization of Heterobiaryls: Hydroarylation of Vinyl Ethers and Bicycloalkenes.
Romero-Arenas, Antonio; Hornillos, Valentín; Iglesias-Sigüenza, Javier; Fernández, Rosario; López-Serrano, Joaquín; Ros, Abel; Lassaletta, José M; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b12858

data_4134000
_publ_section_title
;
 Ir-Catalyzed Atroposelective Desymmetrization of Heterobiaryls:
 Hydroarylation of Vinyl Ethers and Bicycloalkenes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12858
_journal_year                    2020
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   9.4573(2)
_cell_length_b                   9.4573(2)
_cell_length_c                   66.220(2)
_cell_measurement_reflns_used    9608
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      65.20
_cell_measurement_theta_min      4.01
_cell_volume                     5129.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_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       77
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            46704
_diffrn_reflns_point_group_measured_fraction_full 0.803
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        65.265
_diffrn_reflns_theta_max         65.265
_diffrn_reflns_theta_min         4.005
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.15(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         4701
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_full    0.635
_reflns_Friedel_fraction_max     0.635
_reflns_number_gt                4656
_reflns_number_total             4701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12858_si_011.cif
_cod_data_source_block           igl7118a
_cod_original_cell_volume        5129.2(3)
_cod_database_code               4134000
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              63571
_shelx_hkl_checksum              22709