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_7134027
_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 H13 F3 N2 O'
_chemical_formula_sum            'C18 H13 F3 N2 O'
_chemical_formula_weight         330.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-26
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.2399(12)
_cell_length_b                   47.800(4)
_cell_length_c                   8.1006(7)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    294.00
_cell_measurement_theta_max      67.786
_cell_measurement_theta_min      3.699
_cell_volume                     6288.2(9)
_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      294.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -57
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27508
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.742
_diffrn_reflns_theta_min         3.699
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0683 after correction.
The Ratio of minimum to maximum transmission is 0.8562.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0505P)^2^+2.8909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2729
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05513f2.cif
_cod_data_source_block           cjh_5452_0ma
_cod_depositor_comments
'Adding full bibliography for 7134027--7134028.cif.'
_cod_database_code               7134027
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.846
_shelx_estimated_absorpt_t_min   0.782
_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:
 N003(H003), N007(H007), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O)
;
_shelx_res_checksum              71603
_shelx_hkl_checksum              11539
_olex2_submission_special_instructions 'No special instructions were received'