Nickel-catalyzed selective C-5 fluorination of 8-aminoquinolines with NFSI
Ding, Junshuai; Zhang, Yingchao; Li, Jizhen; Organic Chemistry Frontiers 4 (2017) 1528–; doi:10.1039/C7QO00211D

data_1553769
_publ_section_title
;
 Nickel-catalyzed selective C-5 fluorination of 8-aminoquinolines with
 NFSI
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1528
_journal_paper_doi               10.1039/C7QO00211D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C16 H11 F N2 O'
_chemical_formula_weight         266.27
_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-2014/7
_audit_update_record
;
2017-03-18 deposited with the CCDC.
2017-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.861(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.229(10)
_cell_length_b                   3.9190(19)
_cell_length_c                   15.628(8)
_cell_measurement_reflns_used    616
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.77
_cell_measurement_theta_min      2.71
_cell_volume                     1250.7(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7250
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.654
_diffrn_reflns_theta_min         0.997
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       Block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0984P)^2^+1.0457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1368
_reflns_number_total             2342
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00211d2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1250.7(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553769
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              82839
_shelx_hkl_checksum              82236