Stereoselective migratory heteroaryltrifluoromethylation of allylic amines via electrosynthesis
Lan, Jianyong; Lin, Kejun; Zhang, Xing; Zhu, Tingshun; Green Chemistry 24 (2022) 6138–6144; doi:10.1039/D2GC00960A

data_7245193
_publ_section_title
;
 Stereoselective migratory heteroaryltrifluoromethylation of allylic
 amines via electrosynthesis
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              6138
_journal_page_last               6144
_journal_paper_doi               10.1039/D2GC00960A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 F3 N2 O S'
_chemical_formula_sum            'C19 H17 F3 N2 O S'
_chemical_formula_weight         378.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-12 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.050(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.79170(18)
_cell_length_b                   10.2470(2)
_cell_length_c                   19.1126(4)
_cell_measurement_reflns_used    4038
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.7890
_cell_measurement_theta_min      4.5890
_cell_volume                     1704.86(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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   -107.00 -19.00   1.00    1.00    --  -41.14 -38.00 -90.00   88
  2  \w   -109.00 -26.00   1.00    1.00    --  -41.14 -38.00-180.00   83
  3  \w    -86.00 -53.00   1.00    1.00    --  -41.14 125.00 -90.00   33
  4  \w     84.00 178.00   1.00    1.33    --  105.29  30.00 -60.00   94
  5  \w    118.00 163.00   1.00    1.33    --  105.29 125.00 150.00   45
  6  \w     80.00 177.00   1.00    1.33    --  105.29  30.00  30.00   97
  7  \w     40.00 105.00   1.00    1.33    --  105.29 -94.00-180.00   65
  8  \w     23.00 106.00   1.00    1.33    --  105.29 -94.00  90.00   83
  9  \w    150.00 177.00   1.00    1.33    --  105.29  77.00 -90.00   27
 10  \w    113.00 160.00   1.00    1.33    --  105.29 125.00-120.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1759175000
_diffrn_orient_matrix_UB_12      0.0043376000
_diffrn_orient_matrix_UB_13      0.0026771000
_diffrn_orient_matrix_UB_21      0.0191504000
_diffrn_orient_matrix_UB_22      -0.0054437000
_diffrn_orient_matrix_UB_23      0.0813255000
_diffrn_orient_matrix_UB_31      0.0043350000
_diffrn_orient_matrix_UB_32      -0.1501285000
_diffrn_orient_matrix_UB_33      -0.0027826000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6820
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.942
_diffrn_reflns_theta_min         4.673
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00056(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0432P)^2^+1.0727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3065
_reflns_number_total             3320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc00960a2.cif
_cod_data_source_block           a21060402a0179
_cod_depositor_comments          'Adding full bibliography for 7245193.cif.'
_cod_database_code               7245193
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHONFS
_chemical_oxdiff_usercomment     CF3-1
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), N2(H2)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_date_sample_data_collection 2021-06-04
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.802