Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl Bromides.
Ding, Xiaomei; Huang, Manna; Yi, Zhou; Du, Dongchen; Zhu, Xinhai; Wan, Yiqian; The Journal of organic chemistry 82 (2017) 5416–5423; doi:10.1021/acs.joc.7b00290

data_4032534
_publ_section_title
;
 Room-Temperature CuI-Catalyzed Amination of Aryl Iodides and Aryl
 Bromides.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5416
_journal_page_last               5423
_journal_paper_doi               10.1021/acs.joc.7b00290
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 112.424(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1059(5)
_cell_length_b                   17.6530(7)
_cell_length_c                   9.9226(4)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.1410
_cell_measurement_theta_min      4.7250
_cell_volume                     1636.34(14)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6235
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        62.552
_diffrn_reflns_theta_max         62.552
_diffrn_reflns_theta_min         4.733
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83383
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0601P)^2^+0.1958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2121
_reflns_number_total             2588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00290_si_003.cif
_cod_data_source_block           exp_21021_DXM_L4_MeOH
_cod_original_cell_volume        1636.34(13)
_cod_database_code               4032534
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              61290
_shelx_hkl_checksum              87856