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_4037895
_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         'C18 H15 Br2 N3 O'
_chemical_formula_sum            'C18 H15 Br2 N3 O'
_chemical_formula_weight         449.15
_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             2019-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                94.8160(10)
_cell_angle_beta                 96.6100(10)
_cell_angle_gamma                103.8270(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1864(2)
_cell_length_b                   9.8229(3)
_cell_length_c                   10.8563(3)
_cell_measurement_reflns_used    6785
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.99
_cell_measurement_theta_min      5.10
_cell_volume                     836.43(4)
_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      172.93
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7691
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.974
_diffrn_reflns_theta_min         5.102
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.294
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1098 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.6799. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+0.5782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2975
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03223_si_002.cif
_cod_data_source_block           mj19758_0m
_cod_database_code               4037895
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.565
_olex2_refinement_description
;
1. 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
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C6(H6), C7(H7), C12(H12), C13(H13), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              29812
_shelx_hkl_checksum              70557
_olex2_submission_special_instructions 'No special instructions were received'