Visible light-induced cascade annulation of sulfoxonium ylides with azides for the synthesis of 2-trifluoromethyl indoles.
Cui, Jia-Huan; Chen, Qian-Yu; Zhang, Jun; He, Yan; Li, Xingguang; Liu, Pei-Nian; Chemical communications (Cambridge, England) 61 (2025) 488–491; doi:10.1039/d4cc05513f

data_7134028
_publ_section_title
;
 Visible light-induced cascade annulation of sulfoxonium ylides with
 azides for the synthesis of 2-trifluoromethyl indoles.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              488
_journal_page_last               491
_journal_paper_doi               10.1039/d4cc05513f
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 Br F3 N2 O2 S'
_chemical_formula_sum            'C18 H16 Br F3 N2 O2 S'
_chemical_formula_weight         461.30
_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             2023-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-21 deposited with the CCDC.	2024-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.207(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5134(7)
_cell_length_b                   8.0265(4)
_cell_length_c                   16.5356(7)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      67.297
_cell_measurement_theta_min      9.628
_cell_volume                     1949.22(16)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.974
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30846
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.272
_diffrn_reflns_theta_min         6.026
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.278
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.5629.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0609P)^2^+1.8786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3284
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05513f2.cif
_cod_data_source_block           cjh_633_0ma
_cod_depositor_comments
'Adding full bibliography for 7134027--7134028.cif.'
_cod_database_code               7134028
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.482
_shelx_estimated_absorpt_t_min   0.414
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1A-C16 \\sim Br1B-C16
 with sigma of 0.02
3. Others
 Sof(Br1B)=1-FVAR(1)
 Sof(Br1A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C14(H14), C17(H17), C5(H5), C15(H15), C18(H18), C1(H1), C4(H4),
 C2(H2A), C3(H3)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              55541
_shelx_hkl_checksum              86298
_olex2_submission_special_instructions 'No special instructions were received'