CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.
Wang, Haoxuan; Yang, Jeffrey Chih-Yeh; Buchwald, Stephen L.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b04816

data_4126220
_publ_section_title
;
 CuH-Catalyzed Regioselective Intramolecular Hydroamination for the
 Synthesis of Alkyl-Substituted Chiral Aziridines.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04816
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H29 Cl F3 N2 O1.5'
_chemical_formula_weight         521.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.448(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4745(13)
_cell_length_b                   10.3337(8)
_cell_length_c                   18.463(2)
_cell_measurement_reflns_used    7891
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.79
_cell_measurement_theta_min      5.17
_cell_volume                     2905.0(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34400
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         2.589
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.007
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.061(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     1022
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0745P)^2^+0.3397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4241
_reflns_number_total             5341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b04816_si_002.cif
_cod_data_source_block           X17068_sq
_cod_original_formula_sum        'C29 H29 Cl F3 N2 O1.50'
_cod_database_code               4126220
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              25079
_shelx_hkl_checksum              3728
_shelx_fab_checksum              84238