Electrochemistry-enabled Ir-catalyzed C-H/N-N bond activation facilitates [3+2] annulation of phenidones with propiolates.
Zhao, LuLu; Yang, Jianjing; Yan, Kelu; Cheng, Xingda; Xiao, Ziyang; Wen, Jiangwei; Chemical communications (Cambridge, England) 61 (2025) 2079–2082; doi:10.1039/d4cc03124e

data_7134116
_publ_section_title
;
 Electrochemistry-enabled Ir-catalyzed C-H/N-N bond activation facilitates
 [3+2] annulation of phenidones with propiolates.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2079
_journal_page_last               2082
_journal_paper_doi               10.1039/d4cc03124e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C22 H21 F3 N2 O3'
_chemical_formula_sum            'C22 H21 F3 N2 O3'
_chemical_formula_weight         418.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   15.314(3)
_cell_length_c                   22.569(4)
_cell_measurement_reflns_used    7086
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.76
_cell_measurement_theta_min      2.77
_cell_volume                     4202.4(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39452
_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.902
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.220
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_refine_diff_density_max         0.201
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0569P)^2^+0.7565P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5951
_reflns_number_total             8216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03124e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134116--7134117.cif.
;
_cod_original_cell_volume        4202.8(13)
_cod_database_code               7134116
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              35912
_shelx_hkl_checksum              79503