Electrochemically promoted defluorinative sulfoximination and fluorosulfonylation of non-activated aryl fluorides at room temperature.
Kong, Xianqiang; Chen, Yiyi; Zhang, Shuangquan; Feng, Kun; Chen, Xiaohui; Dong, Lin-Hui; Li, Meng-Hua; Xu, Yuan-Qing; Cao, Zhong-Yan; Chemical science 16 (2025) 14161–14169; doi:10.1039/d5sc03674g

data_1574996
_publ_section_title
;
 Electrochemically promoted defluorinative sulfoximination and
 fluorosulfonylation of non-activated aryl fluorides at room temperature.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              14161
_journal_page_last               14169
_journal_paper_doi               10.1039/d5sc03674g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C14 H22 Cl2 N2 Ni O4 S2'
_chemical_formula_sum            'C14 H22 Cl2 N2 Ni O4 S2'
_chemical_formula_weight         476.06
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-03-24 deposited with the CCDC.	2025-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                98.438(2)
_cell_angle_beta                 101.431(2)
_cell_angle_gamma                101.186(2)
_cell_formula_units_Z            1
_cell_length_a                   5.6865(2)
_cell_length_b                   8.1059(3)
_cell_length_c                   10.9080(4)
_cell_measurement_reflns_used    7574
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.308
_cell_measurement_theta_min      3.542
_cell_volume                     474.41(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10183
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_min         1.941
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1147 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
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    1.666
_exptl_crystal_description       block
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0237
_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^)+(0.0191P)^2^+0.2519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2183
_reflns_number_total             2366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03674g3.cif
_cod_data_source_block           m15514_0m
_cod_depositor_comments          'Adding full bibliography for 1574996.cif.'
_cod_database_code               1574996
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.861
_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, All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_shelx_res_checksum              38639
_olex2_submission_special_instructions 'No special instructions were received'