Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines.
Yang, Qi-Liang; Wang, Xiang-Yang; Lu, Jia-Yan; Zhang, Li-Pu; Fang, Ping; Mei, Tian-Sheng; Journal of the American Chemical Society 140 (2018) 11487–11494; doi:10.1021/jacs.8b07380

data_4132909
_publ_section_title
;
 Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary
 Amines.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11487
_journal_page_last               11494
_journal_paper_doi               10.1021/jacs.8b07380
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H15 Br N4 O2'
_chemical_formula_weight         363.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 105.815(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6835(10)
_cell_length_b                   13.0751(7)
_cell_length_c                   7.3965(5)
_cell_measurement_reflns_used    4536
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      53.619
_cell_measurement_theta_min      5.076
_cell_volume                     1552.39(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8468
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.538
_exptl_absorpt_coefficient_mu    2.660
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.414(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0605P)^2^+1.4454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                2570
_reflns_number_total             2774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07380_si_004.cif
_cod_data_source_block           mo_d8v18620_0m
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4132909
_shelx_estimated_absorpt_t_min   0.632
_shelx_estimated_absorpt_t_max   0.741
_shelxl_version_number           2013-4
_shelx_res_checksum              20516
_shelx_hkl_checksum              19052