Remote C(sp3)–H heteroarylation of N-fluorocarboxamides with quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free conditions
Xuan, Liangming; Du, Ruyang; Lei, Panpan; Zhao, Wei; Tan, Lixiang; Ni, Chuanzhi; Wang, Haifeng; Yan, Qiongjiao; Wang, Wei; Chen, Fener; Green Chemistry 24 (2022) 9475–9481; doi:10.1039/D2GC02874C

data_7245630
_publ_section_title
;
 Remote C(sp3)--H heteroarylation of N-fluorocarboxamides with
 quinoxalin-2(1H)-ones under visible-light-induced photocatalyst-free
 conditions
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              9475
_journal_page_last               9481
_journal_paper_doi               10.1039/D2GC02874C
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C22 H22 F3 N3 O2'
_chemical_formula_weight         417.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-14 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.661(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6009(12)
_cell_length_b                   21.017(3)
_cell_length_c                   11.5416(15)
_cell_measurement_reflns_used    6535
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.57
_cell_measurement_theta_min      2.57
_cell_volume                     2079.4(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20545
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.263
_diffrn_reflns_theta_min         2.566
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       Block
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 981 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0520P)^2^+1.2413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.909
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                2521
_reflns_number_total             3589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc02874c2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7245630.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7245630
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              70145