Copper-catalysed dehydrogenative α-C(sp3)–H amination of tetrahydroquinolines with O-benzoyl hydroxylamines
Zhao, He; Chen, Xiuwen; Jiang, Huanfeng; Zhang, Min; Organic Chemistry Frontiers 5 (2018) 539–; doi:10.1039/C7QO00794A

data_1553900
_publ_section_title
;
 Copper-catalysed dehydrogenative \a-C(sp3)--H amination of
 tetrahydroquinolines with O-benzoyl hydroxylamines
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              539
_journal_paper_doi               10.1039/C7QO00794A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C13 H13 Br N2 O'
_chemical_formula_sum            'C13 H13 Br N2 O'
_chemical_formula_weight         293.16
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-06-07 deposited with the CCDC.
2017-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.144(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6730(7)
_cell_length_b                   11.9750(8)
_cell_length_c                   10.6305(8)
_cell_measurement_reflns_used    2162
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.47
_cell_measurement_theta_min      2.570
_cell_volume                     1224.30(15)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7785
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.570
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.342
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      1.590
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0490P)^2^+0.1986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1427
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00794a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553900
_shelxl_version_number           2014-3
_shelx_res_checksum              16111
_shelx_hkl_checksum              10424