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_7133467
_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         '(C46 H32 N6 O2 S4 F12), 2.5 (CHCl3)'
_chemical_formula_sum            'C48.5 H34.5 Cl7.5 F12 N6 O2 S4'
_chemical_formula_weight         1355.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                79.382(2)
_cell_angle_beta                 87.727(2)
_cell_angle_gamma                73.299(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9640(7)
_cell_length_b                   14.7925(9)
_cell_length_c                   19.0470(9)
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.671
_cell_measurement_theta_min      2.360
_cell_volume                     2907.9(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0685
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            106552
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.671
_diffrn_reflns_theta_min         2.360
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.412
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4659
_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    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1366
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     769
_refine_ls_number_reflns         11517
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0989
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.3806P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3598
_refine_ls_wR_factor_ref         0.3750
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10602
_reflns_number_total             11517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02473g2.cif
_cod_data_source_block           17
_cod_depositor_comments
'Adding full bibliography for 7133466--7133467.cif.'
_cod_original_formula_sum        'C48.50 H34.50 Cl7.50 F12 N6 O2 S4'
_cod_database_code               7133467
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              76888
_shelx_hkl_checksum              82306
_shelx_fab_checksum              35974