EDA mediated S-N bond coupling of nitroarenes and sodium sulfinate salts.
Lasso, Juan D.; Castillo-Pazos, Durbis J; Sim, Malcolm; Barroso-Flores, Joaquín; Li, Chao-Jun; Chemical science 14 (2023) 525–532; doi:10.1039/d2sc06087f

data_1568131
_publ_section_title
;
 EDA mediated S-N bond coupling of nitroarenes and sodium sulfinate salts.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              525
_journal_page_last               532
_journal_paper_doi               10.1039/d2sc06087f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_sum            'C8 H8 N2 O3 S'
_chemical_formula_weight         212.22
_chemical_name_systematic        N-(4-cyanophenyl)-N-hydroxymethanesulfonamide
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2022-09-21 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.606(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2861(15)
_cell_length_b                   5.4731(10)
_cell_length_c                   20.821(4)
_cell_measurement_reflns_used    1764
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.214
_cell_measurement_theta_min      5.882
_cell_volume                     942.4(3)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13264
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.214
_diffrn_reflns_theta_min         5.882
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.203
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.2907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1764
_reflns_number_total             1809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06087f1.cif
_cod_data_source_block           DC5
_cod_depositor_comments          'Adding full bibliography for 1568131.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1568131
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.422
_shelx_estimated_absorpt_t_max   0.586
_shelx_res_checksum              70209
_shelx_hkl_checksum              76648