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_7245625
_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 O4 S'
_chemical_formula_sum            'C15 H14 N2 O4 S'
_chemical_formula_weight         318.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-08-05 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.27050(10)
_cell_length_b                   12.2230(2)
_cell_length_c                   20.2303(2)
_cell_measurement_reflns_used    5921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3950
_cell_measurement_theta_min      4.2230
_cell_volume                     2786.91(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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    -67.00  33.00   1.00    1.00    --  -35.62  85.00 -89.00  100
  2  \w    -16.00  66.00   1.00    1.00    --   35.62 -84.00  44.00   82
  3  \w    133.00 158.00   1.00    1.40    --  107.12  85.00 -89.00   25
  4  \w    149.00 175.00   1.00    1.40    --  107.12  56.00  48.00   26
  5  \w     69.00 131.00   1.00    1.40    --  107.12 -84.00  44.00   62
  6  \w      4.00  34.00   1.00    1.00    --   35.62 -85.00 151.00   30
  7  \w     57.00  99.00   1.00    1.00    --   35.62 178.00-150.00   42
  8  \w     63.00 108.00   1.00    1.00    --   35.62 178.00  60.00   45
  9  \w     58.00  99.00   1.00    1.00    --   35.62 178.00-180.00   41
 10  \w     39.00  88.00   1.00    1.40    --  107.12 -95.00-120.00   49
 11  \w     98.00 166.00   1.00    1.40    --  107.12  61.00  30.00   68
 12  \w     89.00 174.00   1.00    1.40    --  107.12  61.00 150.00   85
 13  \w     39.00  80.00   1.00    1.40    --  107.12 -95.00 -60.00   41
;
_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      0.1025534000
_diffrn_orient_matrix_UB_12      -0.0285802000
_diffrn_orient_matrix_UB_13      -0.0472871000
_diffrn_orient_matrix_UB_21      0.0634250000
_diffrn_orient_matrix_UB_22      0.1072654000
_diffrn_orient_matrix_UB_23      0.0189713000
_diffrn_orient_matrix_UB_31      0.0645165000
_diffrn_orient_matrix_UB_32      -0.0597506000
_diffrn_orient_matrix_UB_33      0.0565219000
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8630
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.385
_diffrn_reflns_theta_min         4.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65332
_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    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1523 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(8)
_refine_ls_extinction_coef       0.0030(2)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0556P)^2^+0.2399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.708
_reflns_number_gt                4461
_reflns_number_total             4686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           lzh-2-20220531-2
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245625
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 C1 N1 O1 H1'
_shelx_estimated_absorpt_t_max   0.660
_shelx_estimated_absorpt_t_min   0.550
_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:
 C16(H16A,H16B), C38(H38A,H38B), C20(H20A,H20B), C42(H42A,H42B), C19(H19A,
 H19B), C41(H41A,H41B), C39(H39A,H39B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C2(H2), C3(H3), C13(H13), C14(H14), C11(H11), C33(H33), C36(H36),
 C34(H34), C30(H30), C35(H35), C12(H12)
;
_shelx_res_checksum              41969
_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.714