Rh<sup>III</sup>-promoted directed C-H N-heteroarylation of 2-pyridones.
Chi, Rong; Wu, Jia-Xue; Li, Da-Cheng; Dou, Jian-Min; Wang, Huai-Wei; Organic & biomolecular chemistry 21 (2023) 5288–5296; doi:10.1039/d3ob00578j

data_7159387
_publ_section_title
;
 Rh<sup>III</sup>-promoted directed C-H N-heteroarylation of 2-pyridones.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5288
_journal_page_last               5296
_journal_paper_doi               10.1039/d3ob00578j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H10 F3 N3 O'
_chemical_formula_sum            'C16 H10 F3 N3 O'
_chemical_formula_weight         317.27
_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     iterative
_audit_creation_date             2023-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-04-05 deposited with the CCDC.	2023-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.992(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5478(12)
_cell_length_b                   9.6153(8)
_cell_length_c                   10.2086(9)
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.218
_cell_measurement_theta_min      2.863
_cell_volume                     1396.8(2)
_computing_cell_refinement       'SAINT V6.36A (?, 2016)'
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6619
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.556
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     630
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0770
_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^)+(0.1028P)^2^+1.7744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2114
_refine_ls_wR_factor_ref         0.2344
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1549
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00578j2.cif
_cod_data_source_block           221113e
_cod_depositor_comments          'Adding full bibliography for 7159387.cif.'
_cod_database_code               7159387
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15)
;
_shelx_res_checksum              98242
_olex2_submission_special_instructions 'No special instructions were received'