Copper(ii)-catalyzed C5 and C7 halogenation of quinolines using sodium halides under mild conditions.
Xu, Jun; Zhu, Xiaolei; Zhou, Guobin; Ying, Beibei; Ye, Pingping; Su, Lingying; Shen, Chao; Zhang, Pengfei; Organic & biomolecular chemistry 14 (2016) 3016–3021; doi:10.1039/c6ob00169f

data_7154971
_publ_section_title
;
 Copper(ii)-catalyzed C5 and C7 halogenation of quinolines using sodium
 halides under mild conditions.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3016
_journal_page_last               3021
_journal_paper_doi               10.1039/c6ob00169f
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C16 H10 Br2 N2 O'
_chemical_formula_weight         406.08
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-03 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.03
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0468(7)
_cell_length_b                   12.1197(10)
_cell_length_c                   7.5388(7)
_cell_measurement_temperature    293(2)
_cell_volume                     735.10(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9209
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    5.513
_exptl_absorpt_correction_T_max  0.4082
_exptl_absorpt_correction_T_min  0.3755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.979
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.90(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+1.9783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                2537
_reflns_number_total             2595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00169f2.cif
_cod_data_source_block           ww
_cod_depositor_comments          'Adding full bibliography for 7154971.cif.'
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               7154971