N- and O-Arylation of Pyridin-2-ones with Diaryliodonium Salts: Base-Dependent Orthogonal Selectivity under Metal-Free Conditions
Kuriyama, Masami; Hanazawa, Natsumi; Abe, Yusuke; Katagiri, Kotone; Ono, Shimpei; Yamamoto, Kosuke; Onomura, Osamu; Chemical Science  (2020) –; doi:10.1039/D0SC02516J

data_1558640
_publ_section_title
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 N- and O-Arylation of Pyridin-2-ones with Diaryliodonium Salts:
 Base-Dependent Orthogonal Selectivity under Metal-Free Conditions
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02516J
_journal_year                    2020
_chemical_formula_moiety         'C18 H13 F3 I N O'
_chemical_formula_sum            'C18 H13 F3 I N O'
_chemical_formula_weight         443.21
_chemical_melting_point          416.5(5)
_chemical_name_systematic
'Diphenyliodonium 2-oxo-5-(trifluoromethyl)-2H-pyridin-1-ide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-04-27 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.278(5)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.0218(15)
_cell_length_b                   15.569(4)
_cell_length_c                   17.415(4)
_cell_measurement_reflns_used    4663
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.80
_cell_volume                     1632.3(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13311
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.755
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.998
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             864.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.90
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0446P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3118
_reflns_number_total             3666
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d0sc02516j2.cif
_cod_data_source_block           1929a
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_chemical_melting_point' value '416-417' was changed to
'416.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
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_cod_database_code               1558640
_shelx_res_checksum              73673