Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes
Feng, Sheng; Hao, Hua; Liu, Peng; Buchwald, Stephen L.; ACS Catalysis  (2019) 282–; doi:10.1021/acscatal.9b04871

data_4517164
_publ_section_title
;
 Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained
 Trisubstituted Alkenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              282
_journal_paper_doi               10.1021/acscatal.9b04871
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H29 N S'
_chemical_formula_weight         375.55
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.997(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0414(11)
_cell_length_b                   5.7208(4)
_cell_length_c                   14.1145(12)
_cell_measurement_reflns_used    9701
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.20
_cell_volume                     1050.48(15)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      99(2)
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon2 CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            89778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_min         1.446
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7363
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
; 
 Flack x determined using 2665 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       0.192(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6421
_refine_ls_number_restraints     366
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0714P)^2^+0.1157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6156
_reflns_number_total             6421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04871_si_002.cif
_cod_data_source_block           P19056
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4517164
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              32223
_shelx_hkl_checksum              65809