Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions
Xu, Jun; Qiao, Li; Ying, Beibei; Zhu, Xiaolei; Shen, Chao; Zhang, Pengfei; Organic Chemistry Frontiers 4 (2017) 1116–; doi:10.1039/C6QO00655H

data_1553591
_publ_section_title
;
 Transition-metal-free direct perfluoroalkylation of quinoline amides at
 C5 position through radical cross-coupling under mild conditions
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1116
_journal_paper_doi               10.1039/C6QO00655H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C20 H13 F7 N2 O'
_chemical_formula_sum            'C20 H13 F7 N2 O'
_chemical_formula_weight         430.32
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-06 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.858(3)
_cell_length_b                   26.656(8)
_cell_length_c                   8.984(3)
_cell_measurement_reflns_used    2910
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.032
_cell_measurement_theta_min      2.393
_cell_volume                     1881.8(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 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      296.15
_diffrn_measured_fraction_theta_full 0.725
_diffrn_measured_fraction_theta_max 0.759
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.725
_diffrn_reflns_Laue_measured_fraction_max 0.759
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8261
_diffrn_reflns_point_group_measured_fraction_full 0.725
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_min         2.592
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0694P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1595
_reflns_number_total             3334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00655h2.cif
_cod_data_source_block           xj72_0m
_cod_database_code               1553591
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              62060
_shelx_hkl_checksum              10
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'