Copper-Catalyzed Electrochemical Selective Bromination Of 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent.
Yang, Xiang; Yang, Qi-Liang; Wang, Xiang-Yang; Xu, Haohan; Mei, Tian-Sheng; Huang, Yan; Fang, Ping; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b03223

data_4037894
_publ_section_title
;
 Copper-Catalyzed Electrochemical Selective Bromination Of
 8-Aminoquinoline Amide Using NH4Br as the Brominating Reagent.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03223
_journal_year                    2019
_chemical_formula_moiety         'C17 H11 Br3 N2 O'
_chemical_formula_sum            'C17 H11 Br3 N2 O'
_chemical_formula_weight         499.01
_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             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                66.668(3)
_cell_angle_beta                 89.608(3)
_cell_angle_gamma                83.644(3)
_cell_formula_units_Z            4
_cell_length_a                   8.1688(4)
_cell_length_b                   14.2208(7)
_cell_length_c                   15.5925(8)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      2.97
_cell_volume                     1651.63(15)
_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      170.02
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.983
_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_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6189
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.078
_diffrn_reflns_theta_min         4.731
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.292
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 31682 reflections, Rint = 0.2058
 (12518 with I > 3sig(I), Rint = 0.1966)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.005
_refine_diff_density_max         2.142
_refine_diff_density_min         -1.355
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.1146
_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^)+(0.1000P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2734
_refine_ls_wR_factor_ref         0.2925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4281
_reflns_number_total             6189
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03223_si_004.cif
_cod_data_source_block           mj19479_0m
_cod_database_code               4037894
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.519
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.743(7)
 0.257(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 N1A(H1A), C4A(H4A), C5A(H5A), C10A(H10A), C11A(H11A), C14A(H14A), C15A(H15A),
 C16A(H16A)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC)
;
_shelx_res_checksum              91557
_shelx_hkl_checksum              82721
_olex2_submission_special_instructions 'No special instructions were received'