#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558640.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1558640
loop_
_publ_author_name
'Kuriyama, Masami'
'Hanazawa, Natsumi'
'Abe, Yusuke'
'Katagiri, Kotone'
'Ono, Shimpei'
'Yamamoto, Kosuke'
'Onomura, Osamu'
_publ_section_title
;
 N- and O-Arylation of Pyridin-2-ones with Diaryliodonium Salts:
 Base-Dependent Orthogonal Selectivity under Metal-Free Conditions
;
_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       ω
_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/[σ²(Fo²)+(0.0446P)²] where P=(Fo²+2Fc²)/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     F²>2.0σ(F²)
_cod_data_source_file            d0sc02516j2.cif
_cod_data_source_block           1929a
_cod_depositor_comments
;
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 
;
_cod_database_code               1558640
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73615(5) 0.10642(2) 0.51481(2) 0.01436(12) Uani 1 1 d . . . . .
F1 F 0.6231(6) 0.0505(2) 0.1361(2) 0.0475(10) Uani 1 1 d . . . . .
F2 F 0.8255(6) 0.1572(3) 0.1073(2) 0.0602(13) Uani 1 1 d . . . . .
F3 F 0.5473(5) 0.1737(2) 0.17981(17) 0.0323(8) Uani 1 1 d . . . . .
O1 O 1.2234(6) 0.0512(2) 0.42750(18) 0.0193(7) Uani 1 1 d . . . . .
N1 N 0.9089(7) 0.1055(3) 0.3706(2) 0.0176(9) Uani 1 1 d . . . . .
C1 C 0.6656(8) 0.2335(3) 0.4796(3) 0.0155(10) Uani 1 1 d . . . . .
C2 C 0.4596(8) 0.2519(3) 0.4464(3) 0.0181(10) Uani 1 1 d . . . . .
H2 H 0.3538 0.2076 0.4369 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4120(8) 0.3366(3) 0.4273(3) 0.0202(11) Uani 1 1 d . . . . .
H3 H 0.2717 0.3506 0.4046 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5668(10) 0.4007(3) 0.4409(3) 0.0260(12) Uani 1 1 d . . . . .
H4 H 0.5324 0.4584 0.4274 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7699(9) 0.3813(3) 0.4739(3) 0.0249(12) Uani 1 1 d . . . . .
H5 H 0.8751 0.4256 0.4837 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8215(8) 0.2969(3) 0.4929(3) 0.0196(11) Uani 1 1 d . . . . .
H6 H 0.9629 0.2830 0.5148 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5705(8) 0.1292(3) 0.6196(3) 0.0162(10) Uani 1 1 d . . . . .
C8 C 0.6788(8) 0.1771(3) 0.6758(3) 0.0187(10) Uani 1 1 d . . . . .
H8 H 0.8232 0.1994 0.6676 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5725(9) 0.1920(3) 0.7444(3) 0.0258(12) Uani 1 1 d . . . . .
H9 H 0.6420 0.2262 0.7832 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3637(10) 0.1568(3) 0.7560(3) 0.0265(12) Uani 1 1 d . . . . .
H10 H 0.2922 0.1659 0.8034 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2599(9) 0.1090(3) 0.6995(3) 0.0254(12) Uani 1 1 d . . . . .
H11 H 0.1179 0.0850 0.7086 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3600(8) 0.0952(3) 0.6289(3) 0.0200(11) Uani 1 1 d . . . . .
H12 H 0.2867 0.0639 0.5890 0.024 Uiso 1 1 calc R U . . .
C13 C 1.1139(8) 0.0687(3) 0.3652(3) 0.0172(10) Uani 1 1 d . . . . .
C14 C 1.1991(8) 0.0527(3) 0.2909(3) 0.0179(10) Uani 1 1 d . . . . .
H14 H 1.3440 0.0294 0.2864 0.022 Uiso 1 1 calc R U . . .
C15 C 1.0754(8) 0.0704(3) 0.2261(3) 0.0198(11) Uani 1 1 d . . . . .
H15 H 1.1327 0.0595 0.1766 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8611(8) 0.1052(3) 0.2340(3) 0.0177(10) Uani 1 1 d . . . . .
C17 C 0.7884(8) 0.1214(3) 0.3064(3) 0.0164(10) Uani 1 1 d . . . . .
H17 H 0.6443 0.1452 0.3116 0.020 Uiso 1 1 calc R U . . .
C18 C 0.7165(9) 0.1217(4) 0.1650(3) 0.0241(12) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 I1 C7 89.88(17) . . ?
C17 N1 C13 119.5(4) . . ?
C6 C1 C2 121.5(5) . . ?
C6 C1 I1 119.4(4) . . ?
C2 C1 I1 119.1(4) . . ?
C1 C2 C3 118.3(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.3(5) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C12 122.7(4) . . ?
C8 C7 I1 118.3(3) . . ?
C12 C7 I1 119.0(4) . . ?
C7 C8 C9 118.7(5) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 117.2(5) . . ?
C7 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
O1 C13 N1 118.5(4) . . ?
O1 C13 C14 122.7(4) . . ?
N1 C13 C14 118.8(4) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 118.7(4) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 118.3(4) . . ?
C17 C16 C18 121.2(4) . . ?
C15 C16 C18 120.5(5) . . ?
N1 C17 C16 123.8(4) . . ?
N1 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
F3 C18 F2 106.6(5) . . ?
F3 C18 F1 105.1(4) . . ?
F2 C18 F1 105.7(5) . . ?
F3 C18 C16 112.6(4) . . ?
F2 C18 C16 113.0(4) . . ?
F1 C18 C16 113.3(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.112(5) . ?
I1 C7 2.129(5) . ?
F1 C18 1.335(6) . ?
F2 C18 1.333(6) . ?
F3 C18 1.332(6) . ?
O1 C13 1.287(6) . ?
N1 C17 1.342(6) . ?
N1 C13 1.366(6) . ?
C1 C6 1.378(7) . ?
C1 C2 1.387(6) . ?
C2 C3 1.388(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.382(7) . ?
C7 C12 1.387(7) . ?
C8 C9 1.388(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.424(7) . ?
C14 C15 1.367(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(7) . ?
C16 C18 1.490(7) . ?
C17 H17 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(7) . . . . ?
I1 C1 C2 C3 176.7(3) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C2 C1 C6 C5 1.3(7) . . . . ?
I1 C1 C6 C5 -176.2(4) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
C12 C7 C8 C9 -0.1(7) . . . . ?
I1 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C10 1.8(7) . . . . ?
C8 C9 C10 C11 -1.4(8) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C8 C7 C12 C11 -1.9(7) . . . . ?
I1 C7 C12 C11 177.8(3) . . . . ?
C10 C11 C12 C7 2.2(7) . . . . ?
C17 N1 C13 O1 -177.5(4) . . . . ?
C17 N1 C13 C14 3.6(7) . . . . ?
O1 C13 C14 C15 178.5(5) . . . . ?
N1 C13 C14 C15 -2.7(7) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C14 C15 C16 C18 -177.1(5) . . . . ?
C13 N1 C17 C16 -2.1(7) . . . . ?
C15 C16 C17 N1 -0.4(7) . . . . ?
C18 C16 C17 N1 178.0(5) . . . . ?
C17 C16 C18 F3 17.7(7) . . . . ?
C15 C16 C18 F3 -163.8(4) . . . . ?
C17 C16 C18 F2 138.5(5) . . . . ?
C15 C16 C18 F2 -43.0(7) . . . . ?
C17 C16 C18 F1 -101.4(6) . . . . ?
C15 C16 C18 F1 77.1(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306600
