Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines.
Mahanty, Kingshuk; Saha, Suman Kumar; Halder, Atreyee; De Sarkar, Suman; Chemical communications (Cambridge, England) 59 (2023) 4467–4470; doi:10.1039/d3cc00231d

data_7131423
_publ_section_title
;
 Mediator-free electrochemical trifluoromethylation: a cascade approach
 for the synthesis of trifluoromethylated isoxazolines.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4467
_journal_page_last               4470
_journal_paper_doi               10.1039/d3cc00231d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C11 H9 Cl F3 N O'
_chemical_formula_sum            'C11 H9 Cl F3 N O'
_chemical_formula_weight         263.64
_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     iterative
_audit_creation_date             2022-09-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2023-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.292(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0286(3)
_cell_length_b                   10.8221(2)
_cell_length_c                   7.36612(15)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.0020
_cell_measurement_theta_min      3.2130
_cell_volume                     1092.68(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -85.00  -9.00   0.50    0.20    --  -40.33 121.00 -20.00  152
  2  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  30.00   64
  3  \w    -24.00  35.00   0.50    0.20    --  -40.33  12.00  60.00  118
  4  \w    -43.00  26.00   0.50    0.20    --  -40.33  38.00 150.00  138
  5  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00 150.00  122
  6  \w     97.00 163.00   0.50    0.20    --   96.67 121.00 -20.00  132
  7  \w     81.00 164.00   0.50    0.20    --   96.67 145.00 -60.00  166
  8  \w     99.00 164.00   0.50    0.20    --   96.67 117.00-180.00  130
  9  \w    105.00 170.00   0.50    0.20    --   96.67  96.00 -60.00  130
 10  \w    105.00 170.00   0.50    0.20    --   96.67  96.00 -30.00  130
 11  \w     83.00 164.00   0.50    0.20    --   96.67  33.00 150.00  162
 12  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 -60.00  190
 13  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00-150.00  122
 14  \w    -26.00  43.00   0.50    0.20    --   40.33 -38.00 -90.00  138
 15  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00-180.00  154
 16  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-120.00   78
 17  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -90.00   54
 18  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00 -60.00   78
 19  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  30.00   54
 20  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  60.00   54
 21  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 22  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 23  \w     22.00 106.00   0.50    0.20    --   96.67 -96.00  60.00  168
 24  \w     49.00 110.00   0.50    0.20    --   40.33-154.00  98.00  122
 25  \w     49.00 132.00   0.50    0.20    --   96.67-154.00  98.00  166
 26  \w     44.00 127.00   0.50    0.20    --   96.67-145.00   0.00  166
 27  \w     31.00 111.00   0.50    0.20    --   96.67-121.00-103.00  160
 28  \w     31.00  88.00   0.50    0.20    --   40.33-121.00-103.00  114
 29  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -30.00  192
 30  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00   0.00  182
 31  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00  90.00  182
 32  \w   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 150.00  192
 33  \w   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00  30.00  172
 34  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00-180.00  182
 35  \w   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00-150.00  172
 36  \w   -153.00 -68.00   0.50    0.20    --  -82.50 -25.00 -90.00  170
 37  \w   -149.00 -75.00   0.50    0.20    --  -82.50-121.00-103.00  148
 38  \w   -109.00 -53.00   0.50    0.20    --  -40.33-154.00  98.00  112
 39  \w   -147.00 -53.00   0.50    0.20    --  -82.50-154.00  98.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0984164000
_diffrn_orient_matrix_UB_12      0.0667967000
_diffrn_orient_matrix_UB_13      0.0162956000
_diffrn_orient_matrix_UB_21      0.0537414000
_diffrn_orient_matrix_UB_22      -0.1246549000
_diffrn_orient_matrix_UB_23      0.0358410000
_diffrn_orient_matrix_UB_31      -0.0075045000
_diffrn_orient_matrix_UB_32      -0.0160932000
_diffrn_orient_matrix_UB_33      -0.2104114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0013(3)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0559P)^2^+0.7809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1873
_reflns_number_total             1981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00231d2.cif
_cod_data_source_block           sks-4clcf3_auto
_cod_depositor_comments          'Adding full bibliography for 7131423.cif.'
_cod_database_code               7131423
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Cl F'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C6(H6)
;
_shelx_res_checksum              78031
_shelx_hkl_checksum              53597
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.006
_oxdiff_exptl_absorpt_empirical_full_min 0.659