Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes.
Whyte, Andrew; Torelli, Alexa; Mirabi, Bijan; Prieto, Liher; Rodríguez, José F; Lautens, Mark; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c03246

data_4134912
_publ_section_title
;
 Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c03246
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H28 Cl N3 O2 S'
_chemical_formula_sum            'C32 H28 Cl N3 O2 S'
_chemical_formula_weight         554.08
_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                   8.9830(5)
_cell_length_b                   12.8241(7)
_cell_length_c                   24.4677(16)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.30
_cell_volume                     2818.7(3)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            44676
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.665
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1950 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.006(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0393P)^2^+0.4210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5135
_reflns_number_total             6488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c03246_si_001.cif
_cod_data_source_block           d19195_a
_cod_database_code               4134912
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              80591
_shelx_hkl_checksum              95169