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_7245621
_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         'C13 H10 N2 O3 S'
_chemical_formula_sum            'C13 H10 N2 O3 S'
_chemical_formula_weight         274.29
_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             2022-04-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-19 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                101.965(7)
_cell_angle_beta                 90.131(9)
_cell_angle_gamma                92.439(8)
_cell_formula_units_Z            2
_cell_length_a                   6.9208(9)
_cell_length_b                   7.4115(6)
_cell_length_c                   11.9359(12)
_cell_measurement_reflns_used    2242
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      3.7240
_cell_volume                     598.35(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     13.00  56.00   1.00    1.00    --   40.73 -99.00 -90.00   43
  2  \w     23.00  59.00   1.00    1.00    --   40.73-125.00   0.00   36
  3  \w     28.00  95.00   1.00    1.00    --   40.73-125.00  90.00   67
  4  \w     35.00 137.00   1.00    1.50    --  107.58 -61.00   0.00  102
  5  \w     80.00 106.00   1.00    1.50    --  107.58 -94.00   0.00   26
  6  \w     41.00 129.00   1.00    1.50    --  107.58 -45.00  90.00   88
  7  \w     89.00 158.00   1.00    1.50    --  107.58  45.00  90.00   69
  8  \w    117.00 177.00   1.00    1.50    --  107.58 125.00 -90.00   60
  9  \w    111.00 137.00   1.00    1.50    --  107.58 125.00-180.00   26
 10  \w     59.00 178.00   1.00    1.50    --  107.58  15.00  30.00  119
 11  \w     93.00 133.00   1.00    1.50    --  107.58 -45.00-180.00   40
 12  \w     72.00 105.00   1.00    1.50    --  107.58 -94.00-180.00   33
 13  \w     46.00  73.00   1.00    1.50    --  107.58 -45.00-180.00   27
 14  \w     26.00 108.00   1.00    1.50    --  107.58 -94.00 -90.00   82
 15  \w     45.00  86.00   1.00    1.50    --  107.58 -61.00 -60.00   41
 16  \w   -115.00 -17.00   1.00    1.00    --  -40.73 -38.00 120.00   98
 17  \w   -120.00  -6.00   1.00    1.00    --  -40.73 -19.00-180.00  114
 18  \w    -35.00 -18.00   1.00    1.00    --  -41.23 125.00 -90.00   17
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0779135000
_diffrn_orient_matrix_UB_12      -0.0286007000
_diffrn_orient_matrix_UB_13      -0.1229534000
_diffrn_orient_matrix_UB_21      -0.2015039000
_diffrn_orient_matrix_UB_22      0.0348271000
_diffrn_orient_matrix_UB_23      -0.0441805000
_diffrn_orient_matrix_UB_31      0.0545192000
_diffrn_orient_matrix_UB_32      0.2078524000
_diffrn_orient_matrix_UB_33      0.0185105000
_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  0.0401
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3550
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.786
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.1261
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+10.9144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3218
_refine_ls_wR_factor_ref         0.3232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1990
_reflns_number_total             2102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03218j2.cif
_cod_data_source_block           3-76
_cod_depositor_comments
'Adding full bibliography for 7245620--7245625.cif.'
_cod_database_code               7245621
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(H11A)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=1-FVAR(1)
 Sof(C13)=Sof(H13)=Sof(C12)=Sof(H12)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=
 Sof(H9)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C12(H12), C11(H11A),
 C11(H11), C10(H10), C9(H9), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
3.b Fitted hexagon refined as free rotating group:
 C8(C13,C12,C11,C10,C9)
;
_shelx_res_checksum              26665
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.489