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_4132904
_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_moiety         'C17 H19 N3 O3'
_chemical_formula_sum            'C17 H19 N3 O3'
_chemical_formula_weight         313.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                86.4210(10)
_cell_angle_beta                 80.8950(10)
_cell_angle_gamma                62.7930(10)
_cell_formula_units_Z            4
_cell_length_a                   11.0414(2)
_cell_length_b                   11.7274(2)
_cell_length_c                   14.0159(3)
_cell_measurement_reflns_used    7143
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      54.810
_cell_measurement_theta_min      2.779
_cell_volume                     1593.64(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      302.02
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17038
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.963
_diffrn_reflns_theta_min         2.778
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1151 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.7640. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.3815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4314
_reflns_number_total             6012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07380_si_002.cif
_cod_data_source_block           mjr18037_0m
_cod_database_code               4132904
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3A), C4(H4), C8(H8), C9(H9), C11(H11), N5(H5),
 C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_shelx_res_checksum              36356
_shelx_hkl_checksum              82340
_olex2_submission_special_instructions 'No special instructions were received'