Transition-metal-free electrochemical oxidative C(sp2)–H trifluoromethylation of aryl aldehyde hydrazones
Shi, Yuan; Wang, Kai; Ding, Yuxin; Xie, Yuanyuan; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01734B

data_7158996
_publ_section_title
;
 Transition-metal-free electrochemical oxidative C(sp2)--H
 trifluoromethylation of aryl aldehyde hydrazones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01734B
_journal_year                    2022
_chemical_formula_moiety         'C12 H11 Br2 F3 N2 O'
_chemical_formula_sum            'C12 H11 Br2 F3 N2 O'
_chemical_formula_weight         416.05
_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     dual
_audit_creation_date             2022-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-13 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.5740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9638(4)
_cell_length_b                   7.6176(2)
_cell_length_c                   16.0976(6)
_cell_measurement_reflns_used    4918
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.72
_cell_volume                     1364.28(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_min         2.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.973
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.1566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.2101.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.026
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.152
_refine_diff_density_min         -1.985
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2551
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01734b2.cif
_cod_data_source_block           mo_220531_shiyuan_24br_0m
_cod_database_code               7158996
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.413
_shelx_estimated_absorpt_t_min   0.158
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
;
_shelx_res_checksum              87130
_olex2_submission_special_instructions 'No special instructions were received'