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_7245624
_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         'C15 H14 N2 O3 S'
_chemical_formula_sum            'C15 H14 N2 O3 S'
_chemical_formula_weight         302.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 101.306(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8870(2)
_cell_length_b                   7.8158(2)
_cell_length_c                   18.9459(4)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.4210
_cell_measurement_theta_min      4.5630
_cell_volume                     1435.63(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (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 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -56.00  34.00   1.00    2.07    --  -35.62  33.00  99.00   90
  2  \w   -105.00 -15.00   1.00    2.07    --  -35.62 -33.00 -58.00   90
  3  \w     15.00 100.00   1.00    2.07    --   35.62  33.00  99.00   85
  4  \w    143.00 169.00   1.00    8.28    --  107.12  33.00  99.00   26
  5  \w     97.00 140.00   1.00    8.28    --  107.12  33.00  99.00   43
  6  \w     54.00 119.00   1.00    8.28    --  107.12 -33.00 -58.00   65
  7  \w     74.00 105.00   1.00    2.07    --   35.62 178.00-120.00   31
  8  \w     22.00 103.00   1.00    2.07    --   35.62  57.00-150.00   81
  9  \w    -13.00  12.00   1.00    2.07    --   35.62 -33.00 -58.00   25
 10  \w     20.00 103.00   1.00    2.07    --   35.62  57.00 120.00   83
 11  \w     57.00  89.00   1.00    8.28    --  107.12 178.00   0.00   32
 12  \w    117.00 143.00   1.00    8.28    --  107.12 178.00   0.00   26
 13  \w     38.00  81.00   1.00    8.28    --  107.12 -95.00  60.00   43
 14  \w     93.00 176.00   1.00    8.28    --  107.12  30.00 150.00   83
 15  \w    102.00 177.00   1.00    8.28    --  107.12 111.00 -30.00   75
 16  \w     42.00  94.00   1.00    8.28    --  107.12 -95.00  90.00   52
 17  \w    101.00 127.00   1.00    8.28    --  107.12  61.00 -30.00   26
 18  \w    129.00 155.00   1.00    8.28    --  107.12  61.00 -30.00   26
 19  \w     37.00 102.00   1.00    8.28    --  107.12-111.00 -60.00   65
;
_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      0.1143044000
_diffrn_orient_matrix_UB_12      -0.0773124000
_diffrn_orient_matrix_UB_13      0.0582891000
_diffrn_orient_matrix_UB_21      0.0897348000
_diffrn_orient_matrix_UB_22      -0.0293182000
_diffrn_orient_matrix_UB_23      -0.0568385000
_diffrn_orient_matrix_UB_31      0.0641666000
_diffrn_orient_matrix_UB_32      0.1789106000
_diffrn_orient_matrix_UB_33      0.0158971000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6295
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.484
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (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    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0560
_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^)+(0.1139P)^2^+0.0645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2421
_reflns_number_total             2745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           lzh-20220311
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245624
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 N1 O1 C1'
_shelx_estimated_absorpt_t_max   0.677
_shelx_estimated_absorpt_t_min   0.570
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C9(H9), C21(H21), C20(H20), C6(H6), C18(H18), C19(H19), C8(H8),
 C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              5668
_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 1.760
_oxdiff_exptl_absorpt_empirical_full_min 0.787