Transition-metal-free oxidative C5 C-H-halogenation of 8-aminoquinoline amides using sodium halides.
Wang, Ying; Wang, Yang; Jiang, Kai; Zhang, Qian; Li, Dong; Organic & biomolecular chemistry 14 (2016) 10180–10184; doi:10.1039/c6ob02079h

data_7155319
_publ_section_title
;
 Transition-metal-free oxidative C5 C-H-halogenation of 8-aminoquinoline
 amides using sodium halides.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10180
_journal_page_last               10184
_journal_paper_doi               10.1039/c6ob02079h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C12 H11 Br N2 O'
_chemical_formula_sum            'C12 H11 Br N2 O'
_chemical_formula_weight         279.14
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-23 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.04(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.473(2)
_cell_length_b                   19.517(4)
_cell_length_c                   7.043(2)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    293.2
_cell_measurement_theta_max      71.9761
_cell_measurement_theta_min      5.3330
_cell_volume                     1139.1(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker D8 VENTURE PHOTON'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_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      293.2
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_radiation_type           'Cu Ka'
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4168
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         72.061
_diffrn_reflns_theta_min         4.527
_exptl_absorpt_coefficient_mu    4.753
_exptl_absorpt_correction_T_max  0.753578
_exptl_absorpt_correction_T_min  0.510519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1164 before and 0.0485 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1358 before and 0.0399 after correction.
 The Ratio of minimum to maximum transmission is 0.68.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 19924 reflections, Rint = 0.0402
 (14944 with I > 3sig(I), Rint = 0.0387)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.0050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0516P)^2^+0.5356P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1708
_reflns_number_total             2160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02079h2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 7155319.cif.'
_cod_original_cell_volume        1139.2(5)
_cod_database_code               7155319
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              1332
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'