Synthesis of 2-CF3-indoles or 2-CF3-indolin-3-ones via anaerobic or aerobic reactions of N-phenylpyridin-2-amines with TFISYs
Liang, Miaomiao; Xu, Yuanshuang; Yang, Xueying; Zhang, Xinying; Fan, Xuesen; Chemical Communications 61 (2025) 8735–8738; doi:10.1039/D5CC01652E

data_7134506
_publ_section_title
;
 Synthesis of 2-CF3-indoles or 2-CF3-indolin-3-ones via anaerobic or
 aerobic reactions of N-phenylpyridin-2-amines with TFISYs
;
_journal_issue                   48
_journal_name_full               'Chemical Communications'
_journal_page_first              8735
_journal_page_last               8738
_journal_paper_doi               10.1039/D5CC01652E
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H14 F3 N3 O'
_chemical_formula_sum            'C20 H14 F3 N3 O'
_chemical_formula_weight         369.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-05-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-02-26 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0044(6)
_cell_length_b                   10.7501(3)
_cell_length_c                   18.9380(6)
_cell_measurement_reflns_used    3921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1990
_cell_measurement_theta_min      4.8720
_cell_volume                     3461.85(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.970
_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     18.00  44.00   1.00    7.27    --   35.62 -72.00  78.00   26
  2  \w     18.00  51.00   1.00    7.27    --   35.62 -51.00-131.00   33
  3  \w    -27.00  -1.00   1.00    7.27    --   35.62 -51.00-131.00   26
  4  \w     47.00 131.00   1.00   29.06    --  106.81 -72.00  78.00   84
  5  \w     74.00  99.00   1.00   29.06    --  106.81-112.00  -0.00   25
  6  \w     91.00 161.00   1.00   29.06    --  106.81  51.00  14.00   70
  7  \w    -97.00 -41.00   1.00    7.27    --  -35.62-178.00  60.00   56
  8  \w    -98.00 -31.00   1.00    7.27    --  -35.62 -57.00  30.00   67
  9  \w     59.00 108.00   1.00    7.27    --   35.62-178.00  90.00   49
 10  \w     89.00 173.00   1.00   29.06    --  106.81  61.00 120.00   84
 11  \w     42.00 105.00   1.00   29.06    --  106.81-111.00-120.00   63
 12  \w     54.00  85.00   1.00   29.06    --  106.81-111.00 -90.00   31
 13  \w     77.00 102.00   1.00   29.06    --  106.81 -51.00-131.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0626132000
_diffrn_orient_matrix_UB_12      0.0464465000
_diffrn_orient_matrix_UB_13      -0.0525856000
_diffrn_orient_matrix_UB_21      0.0632687000
_diffrn_orient_matrix_UB_22      -0.0761879000
_diffrn_orient_matrix_UB_23      0.0389804000
_diffrn_orient_matrix_UB_31      -0.0170679000
_diffrn_orient_matrix_UB_32      -0.1121346000
_diffrn_orient_matrix_UB_33      -0.0482455000
_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  0.0273
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.342
_diffrn_reflns_theta_min         4.670
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.059
_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     244
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0522
_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^)+(0.1243P)^2^+0.9858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2637
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01652e2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7134505--7134506.cif.'
_cod_database_code               7134506
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.832
_reflns_odcompleteness_completeness 98.48
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              43161
_shelx_hkl_checksum              78966
_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 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.763