Visible-light-initiated metal-free Csp3–Csp3 to Csp3–N conversion in homobenzylic sulfonamides with N-iodoimides
Morales-Ortega, Guillermo; Merino, Estíbaliz; Carreras, Javier; Chemical Science 16 (2025) 11413–11418; doi:10.1039/D5SC02168E

data_1574666
_publ_section_title
;
 Visible-light-initiated metal-free Csp3--Csp3 to Csp3--N conversion in
 homobenzylic sulfonamides with N-iodoimides
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              11413
_journal_page_last               11418
_journal_paper_doi               10.1039/D5SC02168E
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C19 H18 N2 O6 S'
_chemical_formula_sum            'C19 H18 N2 O6 S'
_chemical_formula_weight         402.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-14 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                72.0730(10)
_cell_angle_beta                 74.0080(10)
_cell_angle_gamma                67.2850(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2636(3)
_cell_length_b                   10.5834(4)
_cell_length_c                   12.5316(4)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      6.41
_cell_volume                     946.44(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25306
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.429
_diffrn_reflns_theta_min         6.412
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.872
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1226 before and 0.0784 after correction. The Ratio of minimum to maximum transmission is 0.6993. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.3451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3167
_reflns_number_total             3656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc02168e2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 1574666.cif.'
_cod_database_code               1574666
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.767
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C17(H17), C15(H15), C4(H4), C7(H7), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'