Asymmetric Copper-Catalyzed Intermolecular Aminoarylation of Styrenes: Efficient Access to Optical 2,2-Diarylethylamines.
Wang, Dinghai; Wu, Lianqian; Wang, Fei; Wan, Xiaolong; Chen, Pinhong; Lin, Zhenyang; Liu, Guosheng; Journal of the American Chemical Society 139 (2017) 6811–6814; doi:10.1021/jacs.7b02455

data_4126127
_publ_section_title
;
 Asymmetric Copper-Catalyzed Intermolecular Aminoarylation of Styrenes:
 Efficient Access to Optical 2,2-Diarylethylamines.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6811
_journal_page_last               6814
_journal_paper_doi               10.1021/jacs.7b02455
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H20 F N O2 S'
_chemical_formula_weight         369.44
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                84.652(4)
_cell_angle_beta                 70.657(3)
_cell_angle_gamma                67.909(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9044(15)
_cell_length_b                   10.1505(17)
_cell_length_c                   11.649(2)
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.891
_cell_measurement_theta_min      5.213
_cell_volume                     919.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5069
_diffrn_reflns_point_group_measured_fraction_full 0.610
_diffrn_reflns_point_group_measured_fraction_max 0.626
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.854
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Flack x determined using 695 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1082P)^2^+0.0429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.260
_reflns_Friedel_fraction_full    0.252
_reflns_Friedel_fraction_max     0.258
_reflns_number_gt                3542
_reflns_number_total             4061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b02455_si_003.cif
_cod_data_source_block           cd17064
_cod_database_code               4126127
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              11625
_shelx_hkl_checksum              40988