Direct Conversion of <i>N</i>-Alkylamines to <i>N</i>-Propargylamines through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis: Application to Late-Stage Functionalization of Bioactive Molecules.
Chan, Jessica Z.; Yesilcimen, Ahmet; Cao, Min; Zhang, Yuyang; Zhang, Bochao; Wasa, Masayuki; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c08599

data_4135251
_publ_section_title
;
 Direct Conversion of <i>N</i>-Alkylamines to <i>N</i>-Propargylamines
 through C-H Activation Promoted by Lewis Acid/Organocopper Catalysis:
 Application to Late-Stage Functionalization of Bioactive Molecules.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c08599
_journal_year                    2020
_chemical_formula_moiety         'C23 H25 Br N2 O3'
_chemical_formula_sum            'C23 H25 Br N2 O3'
_chemical_formula_weight         457.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.711(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.9630(17)
_cell_length_b                   9.8050(5)
_cell_length_c                   15.0555(8)
_cell_measurement_reflns_used    7494
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      56.21
_cell_measurement_theta_min      3.00
_cell_volume                     4352.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Photon II CPAD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3790
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.526
_diffrn_reflns_theta_max         66.526
_diffrn_reflns_theta_min         2.997
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2016). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     258
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1149P)^2^+0.4543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2617
_reflns_number_total             3790
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            C23H25BrN2O3.cif
_cod_data_source_block           C23H25BrN2O3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4135251
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.348
_shelx_estimated_absorpt_t_max   0.768
_shelx_res_checksum              75818
_shelx_hkl_checksum              32537