Electrochemically driven oxidative C–H/N–H cross-coupling reactions of cyclic sulfamidate imines with primary anilines and secondary amines
Wang, Hai-Xia; Li, Zhi-Hao; Li, Wan-Wan; Qu, Gui-Rong; Yang, Qi-Liang; Guo, Hai-Ming; Green Chemistry 24 (2022) 8377–8385; doi:10.1039/D2GC03218J

data_7245622
_publ_section_title
;
 Electrochemically driven oxidative C--H/N--H cross-coupling reactions of
 cyclic sulfamidate imines with primary anilines and secondary amines
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              8377
_journal_page_last               8385
_journal_paper_doi               10.1039/D2GC03218J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C11 H12 N2 O3 S'
_chemical_formula_sum            'C11 H12 N2 O3 S'
_chemical_formula_weight         252.29
_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
_audit_creation_date             2022-06-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                92.357(4)
_cell_angle_beta                 103.812(4)
_cell_angle_gamma                111.690(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9773(4)
_cell_length_b                   8.6323(4)
_cell_length_c                   8.8553(4)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3400
_cell_measurement_theta_min      5.1910
_cell_volume                     544.55(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -37.00 -10.00   1.00    1.00    --  -35.62  86.00 -41.00   27
  2  \w    -12.00  67.00   1.00    1.00    --   35.62 -86.00-160.00   79
  3  \w     99.00 159.00   1.00    1.00    --  107.12  86.00 -41.00   60
  4  \w     88.00 131.00   1.00    1.00    --  107.12 -86.00-160.00   43
  5  \w    -62.00  -3.00   1.00    1.00    --  -35.62  77.00 120.00   59
  6  \w      5.00  32.00   1.00    1.00    --  -35.62  77.00 120.00   27
  7  \w   -102.00 -18.00   1.00    1.00    --  -35.62 -38.00 -30.00   84
  8  \w    -83.00 -41.00   1.00    1.00    --  -35.62-178.00 150.00   42
  9  \w    -41.00  34.00   1.00    1.00    --  -35.62  38.00 120.00   75
 10  \w      1.00  49.00   1.00    1.00    --   35.62 -99.00 -30.00   48
 11  \w     42.00  71.00   1.00    1.00    --   35.62 -99.00   0.00   29
 12  \w     94.00 172.00   1.00    1.00    --  107.12  61.00   0.00   78
 13  \w     84.00 110.00   1.00    1.00    --  107.12 -95.00  30.00   26
 14  \w     81.00 175.00   1.00    1.00    --  107.12  77.00 120.00   94
 15  \w    125.00 153.00   1.00    1.00    --  107.12 111.00 -90.00   28
 16  \w     41.00 112.00   1.00    1.00    --  107.12-111.00   0.00   71
 17  \w     51.00 123.00   1.00    1.00    --  107.12 -61.00 150.00   72
 18  \w    100.00 130.00   1.00    1.00    --  107.12 111.00-150.00   30
 19  \w     40.00  71.00   1.00    1.00    --  107.12 -95.00  30.00   31
 20  \w    117.00 169.00   1.00    1.00    --  107.12  45.00-180.00   52
 21  \w     40.00 108.00   1.00    1.00    --  107.12 -95.00 150.00   68
 22  \w     85.00 129.00   1.00    1.00    --  107.12 -30.00-180.00   44
 23  \w    138.00 169.00   1.00    1.00    --  107.12 111.00-150.00   31
 24  \w    100.00 135.00   1.00    1.00    --  107.12 111.00  60.00   35
 25  \w    102.00 171.00   1.00    1.00    --  107.12 111.00-180.00   69
 26  \w     82.00 174.00   1.00    1.00    --  107.12  77.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062231000
_diffrn_orient_matrix_UB_12      -0.1791346000
_diffrn_orient_matrix_UB_13      -0.0316945000
_diffrn_orient_matrix_UB_21      -0.1438541000
_diffrn_orient_matrix_UB_22      -0.0293738000
_diffrn_orient_matrix_UB_23      -0.1602813000
_diffrn_orient_matrix_UB_31      0.1611052000
_diffrn_orient_matrix_UB_32      0.0686333000
_diffrn_orient_matrix_UB_33      -0.0779374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3648
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.162
_diffrn_reflns_theta_min         5.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0659P)^2^+0.2422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1969
_reflns_number_total             2064
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           lzh-20211209
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245622
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 N1 C1 H1'
_shelx_estimated_absorpt_t_max   0.503
_shelx_estimated_absorpt_t_min   0.503
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C6(H6), C7(H7)
;
_shelx_res_checksum              77790
_olex2_date_sample_data_collection 2021-12-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.540