Oxidative N-functionalization of primary sulfonamides with aliphatic aldehydes: a green synthesis of α-sulfonamido acetals
Zhou, Zhi-Hua; Wang, Ben; Tan, Jie; Chen, Wei-Yi; Tian, Jie-Sheng; Chemical Communications 61 (2025) 9226–9229; doi:10.1039/D5CC02379C

data_7134564
_publ_section_title
;
 Oxidative N-functionalization of primary sulfonamides with aliphatic
 aldehydes: a green synthesis of \a-sulfonamido acetals
;
_journal_issue                   51
_journal_name_full               'Chemical Communications'
_journal_page_first              9226
_journal_page_last               9229
_journal_paper_doi               10.1039/D5CC02379C
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H25 N O4 S'
_chemical_formula_sum            'C16 H25 N O4 S'
_chemical_formula_weight         327.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-03 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.248(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7519(8)
_cell_length_b                   17.4233(10)
_cell_length_c                   8.7618(6)
_cell_measurement_reflns_used    12092
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.202
_cell_measurement_theta_min      3.367
_cell_volume                     1722.4(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.202
_diffrn_reflns_theta_min         3.367
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0472P)^2^+0.8641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3202
_reflns_number_total             4095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02379c2.cif
_cod_data_source_block           zhou
_cod_depositor_comments          'Adding full bibliography for 7134564.cif.'
_cod_database_code               7134564
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00M) \\sim Ueq, Uanis(O006) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00E(H00C,H00E), C00G(H00G,H00H), C00H(H00I,H00J), C00I(H00K,H00L), C00K(H00P,
 H00Q)
3.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C008(H008), C00A(H00A), C00B(H00B), C00F(H00F)
3.d Idealised Me refined as rotating group:
 C00J(H00M,H00N,H00O), C00L(H00R,H00S,H00T), C00M(H00U,H00V,H00W)
;
_shelx_res_checksum              38296
_shelx_hkl_checksum              51028
_olex2_submission_special_instructions 'No special instructions were received'