Ru-Catalyzed Deoxygenative Regioselective C8-H Arylation of Quinoline <i>N</i>-Oxides.
Kim, Jinwoo; Kim, Suhyeon; Kim, Dongwook; Chang, Sukbok; The Journal of organic chemistry 84 (2019) 13150–13158; doi:10.1021/acs.joc.9b01548

data_4034098
_publ_section_title
;
 Ru-Catalyzed Deoxygenative Regioselective C8-H Arylation of Quinoline
 <i>N</i>-Oxides.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13150
_journal_page_last               13158
_journal_paper_doi               10.1021/acs.joc.9b01548
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H12 F3 N'
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
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_cell_angle_beta                 89.99(3)
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_cell_formula_units_Z            8
_cell_length_a                   10.125(2)
_cell_length_b                   13.337(3)
_cell_length_c                   22.762(5)
_cell_measurement_reflns_used    54825
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      33.575
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_computing_cell_refinement       HKL3000sm
_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_data_reduction        HKL3000sm
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
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_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
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_diffrn_reflns_limit_l_min       -28
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_diffrn_reflns_theta_min         1.790
_diffrn_source                   'PLSII 2D bending magnet'
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_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       rod
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.310
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         12104
_refine_ls_number_restraints     720
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1215P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6078
_reflns_number_total             12104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01548_si_004.cif
_cod_data_source_block           PO19055_002
_cod_original_cell_volume        3010.8(11)
_cod_database_code               4034098
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              17008
_shelx_hkl_checksum              49433