N-Sulfonylation of azoles with sulfonyl hydrazides enabled by electrocatalysis
Huang, Cheng; Kang, Chen; Liu, Hong-Jun; Wang, Chen-Lu; Tang, Sheng; Qin, Yu-Shu; Wei, Zhenhong; Cai, Hu; Green Chemistry 26 (2024) 8706–8710; doi:10.1039/D4GC02474E

data_7248943
_publ_section_title
;
 N-Sulfonylation of azoles with sulfonyl hydrazides enabled by
 electrocatalysis
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              8706
_journal_page_last               8710
_journal_paper_doi               10.1039/D4GC02474E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '0.27(C10 H9 Br N2 O2 S)'
_chemical_formula_sum            'C H Br0.07 Cl N O S0.07'
_chemical_formula_weight         85.94
_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             2024-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-27 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                101.928(6)
_cell_angle_beta                 102.068(6)
_cell_angle_gamma                105.796(6)
_cell_formula_units_Z            15
_cell_length_a                   7.976(3)
_cell_length_b                   12.668(4)
_cell_length_c                   12.714(4)
_cell_measurement_reflns_used    2037
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.74
_cell_volume                     1160.4(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.1244
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7022
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.855
_diffrn_reflns_theta_min         2.740
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2825
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.3789.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             636
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0705P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2603
_reflns_number_total             5121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc02474e2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7248943--7248944.cif.'
_cod_original_cell_volume        1160.5(7)
_cod_database_code               7248943
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'