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_7245623
_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     direct
_audit_creation_date             2022-08-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-21 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                94.600(2)
_cell_angle_beta                 107.839(2)
_cell_angle_gamma                107.022(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0147(2)
_cell_length_b                   8.1452(2)
_cell_length_c                   9.4761(2)
_cell_measurement_reflns_used    5974
_cell_measurement_temperature    295.12(10)
_cell_measurement_theta_max      75.1220
_cell_measurement_theta_min      4.9700
_cell_volume                     553.18(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.12(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_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    102.00 152.00   0.50    0.20    --  109.26  61.00-150.00  100
  2  \w     90.00 124.00   0.50    0.20    --  109.26 137.00 -60.00   68
  3  \w     98.00 178.00   0.50    0.20    --  109.26 125.00 -30.00  160
  4  \w     89.00 177.00   0.50    0.20    --  109.26  30.00 -90.00  176
  5  \w     95.00 150.00   0.50    0.20    --  109.26 125.00  90.00  110
  6  \w     91.00 178.00   0.50    0.20    --  109.26 132.00 122.00  174
  7  \w    -42.00  34.00   0.50    0.05    --  -43.18  37.00 -60.00  152
  8  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00-180.00   74
  9  \w    -27.00  38.00   0.50    0.05    --  -43.18  19.00-120.00  130
 10  \w    -27.00  38.00   0.50    0.05    --  -43.18  19.00   0.00  130
 11  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00 150.00   74
 12  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00  90.00   74
 13  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00  60.00   74
 14  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00 -90.00   74
 15  \w    -51.00 -14.00   0.50    0.20    --  -90.25  45.00-150.00   74
 16  \w    -86.00 -13.00   0.50    0.05    --  -43.18 125.00-150.00  146
 17  \w    -94.00 -19.00   0.50    0.05    --  -43.18 137.00 -60.00  150
 18  \w    -91.00 -17.00   0.50    0.05    --  -43.18 132.00 122.00  148
 19  \w   -164.00 -67.00   0.50    0.20    --  -90.25 -61.00 -30.00  194
 20  \w   -158.00 -66.00   0.50    0.20    --  -90.25-137.00-123.00  184
 21  \w   -164.00 -67.00   0.50    0.20    --  -90.25 -61.00 -60.00  194
 22  \w   -162.00 -69.00   0.50    0.20    --  -90.25-132.00  52.00  186
 23  \w   -117.00 -69.00   0.50    0.05    --  -43.18-132.00  52.00   96
 24  \w   -117.00 -66.00   0.50    0.05    --  -43.18-137.00-123.00  102
 25  \w     42.00  68.00   0.50    0.20    --  109.26 -61.00  90.00   52
 26  \w     37.00  68.00   0.50    0.20    --  109.26 -61.00 120.00   62
 27  \w     38.00  68.00   0.50    0.20    --  109.26 -61.00  60.00   60
 28  \w     42.00  69.00   0.50    0.20    --  109.26 -61.00  30.00   54
 29  \w     35.00  67.00   0.50    0.20    --  109.26 -61.00 -90.00   64
 30  \w     38.00  65.00   0.50    0.20    --  109.26 -61.00-150.00   54
 31  \w     41.00 104.00   0.50    0.05    --   43.18-137.00-123.00  126
 32  \w     41.00 121.00   0.50    0.20    --  109.26-137.00-123.00  160
 33  \w     36.00 111.00   0.50    0.20    --  109.26-125.00 -60.00  150
 34  \w     47.00  91.00   0.50    0.20    --  109.26 -94.00 -60.00   88
 35  \w     38.00 117.00   0.50    0.20    --  109.26-132.00  52.00  158
 36  \w     43.00 107.00   0.50    0.20    --  109.26-125.00  60.00  128
 37  \w     54.00  80.00   0.50    0.20    --  109.26 -94.00  90.00   52
 38  \w     74.00 108.00   0.50    0.20    --  109.26-125.00 150.00   68
 39  \w     38.00 101.00   0.50    0.05    --   43.18-132.00  52.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2031317000
_diffrn_orient_matrix_UB_12      0.0738710000
_diffrn_orient_matrix_UB_13      0.0067324000
_diffrn_orient_matrix_UB_21      0.0665853000
_diffrn_orient_matrix_UB_22      0.0315769000
_diffrn_orient_matrix_UB_23      0.1736823000
_diffrn_orient_matrix_UB_31      0.0145285000
_diffrn_orient_matrix_UB_32      -0.1846176000
_diffrn_orient_matrix_UB_33      -0.0029828000
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7331
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.431
_diffrn_reflns_theta_min         4.991
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0763P)^2^+0.1371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             2163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           3-68
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_original_cell_volume        553.18(2)
_cod_database_code               7245623
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.799
_shelx_estimated_absorpt_t_min   0.711
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C5-H5
 0.84 with sigma of 0.01
 C7-C8
 2.8 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              85558
_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 2.506
_oxdiff_exptl_absorpt_empirical_full_min 0.490