Copper-catalyzed three-component radical aminoazolation of vinylarenes with N-fluorobenzenesulfonimide and trimethylsilylazole derivatives
Yuan, Qingbing; Wu, Caiqiong; Bao, Yonghu; Huang, Zengming; Wang, Hua; Wei, Yun; Wang, Shaowu; Chemical Communications 61 (2025) 9238–9241; doi:10.1039/D5CC01080B

data_7134563
_publ_section_title
;
 Copper-catalyzed three-component radical aminoazolation of vinylarenes
 with N-fluorobenzenesulfonimide and trimethylsilylazole derivatives
;
_journal_issue                   51
_journal_name_full               'Chemical Communications'
_journal_page_first              9238
_journal_page_last               9241
_journal_paper_doi               10.1039/D5CC01080B
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H20 N2 O4 S3'
_chemical_formula_sum            'C23 H20 N2 O4 S3'
_chemical_formula_weight         484.59
_chemical_name_systematic
N-(2-phenyl-2-(thiazol-2-yl)ethyl)-N-(phenylsulfonyl)benzenesulfonamide
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-04-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-18 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                67.846(3)
_cell_angle_beta                 83.629(3)
_cell_angle_gamma                75.229(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5103(7)
_cell_length_b                   11.3848(9)
_cell_length_c                   13.1690(11)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.738
_cell_measurement_theta_min      2.792
_cell_volume                     1142.51(16)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (Bruker, 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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Bruker PHOTON-II area detector'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CMOS-PHOTONII area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON-II area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44012
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.362
_diffrn_reflns_theta_min         2.792
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1091 before and 0.0790 after correction.
The Ratio of minimum to maximum transmission is 0.8224.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7357
_refine_ls_number_restraints     398
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0817
_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^)+(0.1028P)^2^+0.9784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4820
_reflns_number_total             7357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01080b2.cif
_cod_data_source_block           20250417k
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134563.cif.
;
_cod_database_code               7134563
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C17-C16 = C16-C15 = C20-C15 = C20-C19 = C19-C18 = C18-C17
 1.395 with sigma of 0.01
3. Restrained planarity
 N2A, C21A, S1A, C22A, C23A, C14
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C14 \\sim S1 \\sim N2 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim
C20 \\sim C21 \\sim C22 \\sim C23 \\sim S1A \\sim N2A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C23A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
5. Same fragment restrains
{C14, S1A, N2A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A} sigma for
1-2: 0.01, 1-3: 0.01
as in
{C14, S1, N2, C15, C16, C17, C18, C19, C20, C21, C22, C23}
6. Others
 Sof(H14A)=Sof(S1A)=Sof(N2A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=1-FVAR(1)
 Sof(H14)=Sof(S1)=Sof(N2)=Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(C22)=
 Sof(H22)=Sof(C23)=Sof(H23)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C14(H14), C14(H14A)
7.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C22A(H22A),
 C23A(H23A)
;
_shelx_res_checksum              26512
_shelx_hkl_checksum              72086
_olex2_submission_special_instructions 'No special instructions were received'