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_4132905
_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_formula_sum            'C19 H21 N3 O3'
_chemical_formula_weight         339.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 92.280(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.4909(8)
_cell_length_b                   26.885(2)
_cell_length_c                   15.9657(13)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      46.325
_cell_measurement_theta_min      5.198
_cell_volume                     5357.3(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            91345
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.799
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.047
_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   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         9937
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0946
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1500P)^2^+4.6970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2572
_refine_ls_wR_factor_ref         0.3078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6064
_reflns_number_total             9937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07380_si_007.cif
_cod_data_source_block           mo_d8v18280_0m
_cod_original_cell_volume        5357.4(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4132905
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
_shelx_res_checksum              62217
_shelx_hkl_checksum              93323