Selective electrochemical trifluoromethylation of arylamide- or aryl-substituted pyrrole derivatives.
Zhang, Zhanshuo; Dong, Yangkai; Liu, Yaxin; Fang, Jingrui; Li, Yuchen; Xu, Zeya; Zhao, Yulei; Organic & biomolecular chemistry 23 (2025) 9713–9721; doi:10.1039/d5ob01482d

data_7160784
_publ_section_title
;
 Selective electrochemical trifluoromethylation of arylamide- or
 aryl-substituted pyrrole derivatives.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9713
_journal_page_last               9721
_journal_paper_doi               10.1039/d5ob01482d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '0.143(C14 H13 F3 N2 O)'
_chemical_formula_sum            'C2 H1.86 F0.43 N0.29 O0.14'
_chemical_formula_weight         40.32
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-08-14 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                77.137(4)
_cell_angle_beta                 72.363(4)
_cell_angle_gamma                83.642(4)
_cell_formula_units_Z            14
_cell_length_a                   7.3506(11)
_cell_length_b                   9.0318(12)
_cell_length_c                   11.0779(17)
_cell_measurement_reflns_used    3933
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.32
_cell_volume                     682.55(17)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.267
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5423
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.7272.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0846P)^2^+0.1316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2049
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01482d2.cif
_cod_data_source_block           250113_z2_0m
_cod_depositor_comments          'Adding full bibliography for 7160784.cif.'
_cod_database_code               7160784
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F3, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F2, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C5(H5), C1(H1), C4(H4), C3(H3), C2(H2)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'