Transition-Metal- and Oxidant-Free Directed Anodic C-H Sulfonylation of N,N-Disubstituted Anilines with Sulfinates
Wu, Yan-Chen; Jiang, Shuai-Shuai; Luo, Shu-Zheng; Song, Ren-Jie; Li, Jin-Heng; Chemical Communications  (2019) –; doi:10.1039/C9CC03789F

data_7123746
_publ_section_title
;
 Transition-Metal- and Oxidant-Free Directed Anodic C-H Sulfonylation of
 N,N-Disubstituted Anilines with Sulfinates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03789F
_journal_year                    2019
_chemical_formula_moiety         C18H16ClNO2S
_chemical_formula_sum            'C18 H16 Cl N O2 S'
_chemical_formula_weight         345.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-14 deposited with the CCDC.    2019-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.535(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.109(6)
_cell_length_b                   9.708(3)
_cell_length_c                   19.555(6)
_cell_measurement_reflns_used    2213
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.28
_cell_volume                     3390.3(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.1394
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15271
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.228
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5348
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.83(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         11313
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1520
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.794
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                5782
_reflns_number_total             11313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03789f2.cif
_cod_data_source_block           A
_cod_original_cell_volume        3390.5(18)
_cod_database_code               7123746
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              55780