Metal- and additive-free TfOH catalyzed chemoselective O- and S-trifluoroethylation of oxindoles, isoindolines and thio-oxindoles
Lamba, Manisha; Singh, Prasoon Raj; Bhatt, Shubham; Goswami, Avijit; Green Chemistry 26 (2024) 448–455; doi:10.1039/D3GC03702A

data_7247787
_publ_section_title
;
 Metal- and additive-free TfOH catalyzed chemoselective O- and
 S-trifluoroethylation of oxindoles, isoindolines and thio-oxindoles
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              448
_journal_page_last               455
_journal_paper_doi               10.1039/D3GC03702A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C17 H13 F3 N O'
_chemical_formula_sum            'C17 H13 F3 N O'
_chemical_formula_weight         304.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-11 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                68.976(2)
_cell_angle_beta                 87.671(3)
_cell_angle_gamma                69.921(2)
_cell_formula_units_Z            4
_cell_length_a                   10.0648(8)
_cell_length_b                   11.6308(8)
_cell_length_c                   13.8611(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.360
_cell_measurement_theta_min      2.541
_cell_volume                     1416.21(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18765
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.004
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0974 after correction.
The Ratio of minimum to maximum transmission is 0.6324.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0626
_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^)+(0.1047P)^2^+0.3412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4679
_reflns_number_total             5794
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03702a2.cif
_cod_data_source_block           agml_1104_0m
_cod_depositor_comments
;
Adding full bibliography for 7247784--7247789.cif.

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H26 F6 N2 O2'
_cod_original_formula_weight         608.57
_cod_original_formula_moiety         '2(C17 H13 F3 N O)'
_cod_original_formula_units_Z            2
_cod_database_code               7247787
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2'A,H2'B)
2.b Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C8(H8), C7(H7), C5(H5), C11(H11), C13(H13), C16(H16),
 C15(H15), C14(H14), C9(H9), C10(H10), C8'(H8'), C7'(H7'), C5'(H5'), C11'(H11'),
  C13'(H13'), C14'(H14'), C16'(H16'), C9'(H9'), C10'(H10'), C15'(H15')
;
_shelx_res_checksum              9727
_olex2_submission_special_instructions 'No special instructions were received'