Cu-catalyzed N-S bond coupling between hydroxylamines and sulfinic acids: rapid access to <i>N</i>-arylsulfonamides.
Zhu, Lin; Wang, Yang; Guo, Han; Liu, Rui; Wang, Yu; Dang, Meng-Yun; Hu, Feng-Lan; Han, Wen-Jun; Zhan, Jun-Long; Lv, Yunhe; Organic & biomolecular chemistry 24 (2026) 1021–1026; doi:10.1039/d5ob01851j

data_7160952
_publ_section_title
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 Cu-catalyzed N-S bond coupling between hydroxylamines and sulfinic acids:
 rapid access to <i>N</i>-arylsulfonamides.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1021
_journal_page_last               1026
_journal_paper_doi               10.1039/d5ob01851j
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 N2 O4 S'
_chemical_formula_sum            'C12 H11 N2 O4 S'
_chemical_formula_weight         279.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-14 deposited with the CCDC.	2026-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.318(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1939(3)
_cell_length_b                   12.7888(9)
_cell_length_c                   18.6760(13)
_cell_measurement_reflns_used    5483
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.18
_cell_volume                     1238.45(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34424
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.9183.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2103
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.4136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                1938
_reflns_number_total             2103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ob01851j2.cif
_cod_data_source_block           20230712zjl3_0m_a
_cod_database_code               7160952
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C5(H5), C6(H6), C12(H12), C11(H11), C3(H3), C2(H2), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'