Visible-light-induced aerobic C3–H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols
Xu, Xiaobo; Xia, Chengcai; Li, Xiaojun; Sun, Jian; Hao, Liqiang; RSC Advances 10 (2020) 2016–2026; doi:10.1039/C9RA10194B

data_7239876
_publ_section_title
;
 Visible-light-induced aerobic C3--H fluoroalkoxylation of
 quinoxalin-2(1H)-ones with fluoroalkyl alcohols
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2016
_journal_page_last               2026
_journal_paper_doi               10.1039/C9RA10194B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C17 H12 Br F3 N2 O2'
_chemical_formula_sum            'C17 H12 Br F3 N2 O2'
_chemical_formula_weight         413.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-12 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.949(2)
_cell_length_b                   9.0933(12)
_cell_length_c                   25.010(3)
_cell_measurement_reflns_used    2138
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.129
_cell_measurement_theta_min      2.600
_cell_volume                     3328.3(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.620
_diffrn_reflns_theta_min         2.600
_exptl_absorpt_coefficient_mu    2.515
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0592 before and 0.0324 after correction. The Ratio of minimum to maximum transmission is 0.8058. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00040(14)
_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   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0494P)^2^+4.0563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2267
_reflns_number_total             3779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra10194b2.cif
_cod_data_source_block           190415xjf08_0m
_cod_depositor_comments          'Adding full bibliography for 7239876.cif.'
_cod_database_code               7239876
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              10406
_olex2_submission_special_instructions 'No special instructions were received'