Direct electrochemical hydrodefluorination of trifluoromethylketones enabled by non-protic conditions
Box, John R.; Atkins, Alexander P.; Lennox, Alastair J. J.; Chemical Science  (2021) –; doi:10.1039/D1SC01574E

data_1564018
_publ_section_title
;
 Direct electrochemical hydrodefluorination of trifluoromethylketones
 enabled by non-protic conditions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01574E
_journal_year                    2021
_chemical_formula_moiety         'C11 H8 Br F2 N O'
_chemical_formula_sum            'C11 H8 Br F2 N O'
_chemical_formula_weight         288.09
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-05 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.050(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3373(5)
_cell_length_b                   14.2535(9)
_cell_length_c                   9.9567(6)
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.50
_cell_volume                     1041.29(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2506
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.053
_diffrn_reflns_theta_min         2.495
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.951
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.6915.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0257P)^2^+0.6028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2388
_reflns_number_total             2506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01574e2.cif
_cod_data_source_block           testm1_tw
_cod_database_code               1564018
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.288
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H8(0.015) H10(0.02) H11A(0.032) H11B(0.032) H11C(0.032) H4(0.022)
 H2(0.026) H3(0.027)
 Fixed X: H8(0.165539) H10(0.261852) H11A(0.239843) H11B(0.041484)
 H11C(0.079925) H4(0.220704) H2(0.365588) H3(0.305563)
 Fixed Y: H8(0.64567) H10(0.764662) H11A(0.448021) H11B(0.421484)
 H11C(0.524344) H4(0.312355) H2(0.324522) H3(0.238095)
 Fixed Z: H8(0.184564) H10(0.090833) H11A(0.353081) H11B(0.297967)
 H11C(0.355862) H4(0.146965) H2(-0.245749) H3(-0.051711)
;
_shelx_res_checksum              11297
_olex2_submission_special_instructions 'No special instructions were received'