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_7245620
_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 H14 N2 O3 S'
_chemical_formula_sum            'C11 H14 N2 O3 S'
_chemical_formula_weight         254.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 99.853(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9547(2)
_cell_length_b                   8.41310(10)
_cell_length_c                   16.3860(3)
_cell_measurement_reflns_used    2938
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2140
_cell_measurement_theta_min      5.2830
_cell_volume                     1216.26(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.977
_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   -104.00 -18.00   1.00    1.00    --  -35.62 -41.00-122.00   86
  2  \w    -46.00  -3.00   1.00    1.00    --  -35.62  41.00  30.00   43
  3  \w    -14.00  11.00   1.00    1.00    --   35.62 -41.00-122.00   25
  4  \w     45.00 102.00   1.00    1.00    --   35.62  41.00  30.00   57
  5  \w     38.00 123.00   1.00    1.02    --  107.12 -41.00-122.00   85
  6  \w     95.00 124.00   1.00    1.02    --  107.12  41.00  30.00   29
  7  \w    -68.00 -36.00   1.00    1.00    --  -35.62-178.00 -60.00   32
  8  \w    -28.00  52.00   1.00    1.00    --   35.62 -38.00  90.00   80
  9  \w     55.00 105.00   1.00    1.00    --   35.62-178.00-180.00   50
 10  \w     64.00 122.00   1.00    1.02    --  107.12 -45.00  90.00   58
 11  \w     43.00 104.00   1.00    1.02    --  107.12 -77.00 120.00   61
 12  \w    104.00 167.00   1.00    1.02    --  107.12  61.00  30.00   63
 13  \w     44.00  97.00   1.00    1.02    --  107.12 -95.00-120.00   53
 14  \w     72.00 161.00   1.00    1.02    --  107.12  15.00 -30.00   89
 15  \w     48.00  75.00   1.00    1.02    --  107.12 -95.00  30.00   27
 16  \w     39.00 116.00   1.00    1.02    --  107.12 -45.00  30.00   77
;
_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      0.0317046000
_diffrn_orient_matrix_UB_12      0.0671016000
_diffrn_orient_matrix_UB_13      0.0887730000
_diffrn_orient_matrix_UB_21      -0.1518612000
_diffrn_orient_matrix_UB_22      -0.0685496000
_diffrn_orient_matrix_UB_23      0.0161661000
_diffrn_orient_matrix_UB_31      0.0802871000
_diffrn_orient_matrix_UB_32      -0.1558991000
_diffrn_orient_matrix_UB_33      0.0310460000
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5020
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.480
_diffrn_reflns_theta_min         5.286
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58781
_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    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0040(5)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0687P)^2^+0.1811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2056
_reflns_number_total             2313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           lzh-20220328
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245620
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.536
_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:
 C16(H16A,H16B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              54546
_olex2_date_sample_data_collection 2022-03-28
_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 1.954
_oxdiff_exptl_absorpt_empirical_full_min 0.596