Photocatalytic C2-trifluoroethylation and perfluoroalkylation of 3-substituted indoles using fluoroalkyl halides.
Arora, Shivani; Singh, Tavinder; Singh, Anand; Organic & biomolecular chemistry 22 (2024) 4278–4282; doi:10.1039/d4ob00392f

data_7159952
_publ_section_title
;
 Photocatalytic C2-trifluoroethylation and perfluoroalkylation of
 3-substituted indoles using fluoroalkyl halides.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4278
_journal_page_last               4282
_journal_paper_doi               10.1039/d4ob00392f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C12 H12 F3 N'
_chemical_formula_sum            'C12 H12 F3 N'
_chemical_formula_weight         227.23
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-29 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.8790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4607(3)
_cell_length_b                   11.8094(4)
_cell_length_c                   10.5546(3)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.92
_cell_volume                     1078.28(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.705
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.705
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17338
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.705
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.193
_diffrn_reflns_theta_min         2.354
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1398 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.8808.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       square
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0777P)^2^+0.5907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2496
_reflns_number_total             2683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00392f2.cif
_cod_data_source_block           23novb_a
_cod_depositor_comments
;
          Adding full bibliography for 7159952.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.18 H2.18 F0.55 N0.18'
_cod_original_formula_weight         41.31
_cod_original_formula_moiety         '0.182(C12 H12 F3 N)'
_cod_original_formula_units_Z            22
_cod_database_code               7159952
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00F), C00C(H00G), C00F(H00K), C00G(H00L)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00E(H00H,H00I,H00J)
;
_shelx_res_checksum              79768
_olex2_submission_special_instructions 'No special instructions were received'