An aerobic copper-mediated domino process for the synthesis of 3-(trifluoromethylseleno)indoles.
Wang, Hui; Yao, Yunfei; You, Yi; Huang, Yangjie; Weng, Zhiqiang; Organic & biomolecular chemistry 20 (2022) 2115–2120; doi:10.1039/d2ob00063f

data_7158532
_publ_section_title
;
 An aerobic copper-mediated domino process for the synthesis of
 3-(trifluoromethylseleno)indoles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2115
_journal_page_last               2120
_journal_paper_doi               10.1039/d2ob00063f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C22 H15 Br F3 N O2 S Se'
_chemical_formula_sum            'C22 H15 Br F3 N O2 S Se'
_chemical_formula_weight         573.28
_chemical_name_systematic        P1
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-17 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                72.001(2)
_cell_angle_beta                 83.060(2)
_cell_angle_gamma                79.877(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0368(4)
_cell_length_b                   9.7879(5)
_cell_length_c                   12.8089(6)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.616
_cell_measurement_theta_min      3.638
_cell_volume                     1058.06(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21152
_diffrn_reflns_theta_full        66.61
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.960
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00147(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.9950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                3574
_reflns_number_total             3696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00063f2.cif
_cod_data_source_block           3secf3
_cod_depositor_comments          'Adding full bibliography for 7158532.cif.'
_cod_database_code               7158532
_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:
 C17(H17), C13(H13), C10(H10), C4(H4), C16(H16), C20(H20), C7(H7), C11(H11),
 C19(H19), C14(H14), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'