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_4034097
_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            'C23 H21 F6 N O4 Ru'
_chemical_formula_weight         590.48
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.1339(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1949(3)
_cell_length_b                   34.3121(12)
_cell_length_c                   8.5478(3)
_cell_measurement_reflns_used    9352
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.06
_cell_volume                     2296.84(14)
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            40314
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.085
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.488
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.214
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+4.6088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4668
_reflns_number_total             5258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01548_si_003.cif
_cod_data_source_block           A19029_014
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034097
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.778
_shelx_estimated_absorpt_t_max   0.958
_shelx_res_checksum              58038
_shelx_hkl_checksum              96067