Late-stage functionalization of the 4-amino-2-pyridone chemotype using electrochemical and MCR approaches.
Giannessi, Lisa; Longo, Matteo; Massera, Chiara; Radi, Marco; Chemical communications (Cambridge, England) 60 (2024) 11500–11503; doi:10.1039/d4cc02473g

data_7133466
_publ_section_title
;
 Late-stage functionalization of the 4-amino-2-pyridone chemotype using
 electrochemical and MCR approaches.
;
_journal_issue                   81
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11500
_journal_page_last               11503
_journal_paper_doi               10.1039/d4cc02473g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '(C23 H17 F6 N3 O1 S1), 0.5 (H2O)'
_chemical_formula_sum            'C23 H18 F6 N3 O1.5 S'
_chemical_formula_weight         506.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.8237(7)
_cell_length_b                   50.8400(10)
_cell_length_c                   12.4078(5)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.778
_cell_measurement_theta_min      3.477
_cell_volume                     8720.2(6)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Apex III (2016)'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics
;
 Mercury CSD 2023.3.1 (Macrae et al., 2006)
;
_computing_publication_material
'SHELXL and WINGX (Farrugia, J. App. Cryst.2012, 45, 849-854'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'phi & omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35778
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.778
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             4144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+2.2826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                3509
_reflns_number_total             4157
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02473g2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7133466--7133467.cif.'
_cod_original_formula_sum        'C23 H18 F6 N3 O1.50 S'
_cod_database_code               7133466
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              89006
_shelx_hkl_checksum              67556
_shelx_fab_checksum              97615