Copper-Catalyzed Regioselective C–H Amination of Phenol Derivatives with Assistance of Phenanthroline-Based Bidentate Auxiliary
Takamatsu, Kazutaka; Hayashi, Yoshihiro; Kawauchi, Susumu; Hirano, Koji; Miura, Masahiro; ACS Catalysis 9 (2019) 5336–; doi:10.1021/acscatal.9b01145

data_4514782
_publ_section_title
;
 Copper-Catalyzed Regioselective C--H Amination of Phenol Derivatives with
 Assistance of Phenanthroline-Based Bidentate Auxiliary
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5336
_journal_paper_doi               10.1021/acscatal.9b01145
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C43 H32 Cl2 N4 O'
_chemical_formula_sum            'C43 H32 Cl2 N4 O'
_chemical_formula_weight         691.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                60.753(17)
_cell_angle_beta                 79.38(2)
_cell_angle_gamma                76.89(2)
_cell_formula_units_Z            2
_cell_length_a                   11.209(8)
_cell_length_b                   13.582(7)
_cell_length_c                   13.728(8)
_cell_measurement_reflns_used    3830
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1769.4(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18900
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         3.220
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720.00
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.430
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1059P)^2^+0.6525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5457
_reflns_number_total             8071
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs9b01145_si_003.cif
_cod_data_source_block           2976-3
_cod_database_code               4514782
_shelx_res_checksum              30407
_shelx_hkl_checksum              60587