Access to S,C-sulfonium ylides from iodonium ylides <i>via</i> iron catalysis.
Hu, Wanqi; Chen, Xingyu; Wu, Xiaowei; Organic & biomolecular chemistry 24 (2026) 2423–2427; doi:10.1039/d6ob00230g

data_7161050
_publ_section_title
;
 Access to S,C-sulfonium ylides from iodonium ylides <i>via</i> iron
 catalysis.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2423
_journal_page_last               2427
_journal_paper_doi               10.1039/d6ob00230g
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C17 H14 O3 S'
_chemical_formula_sum            'C17 H14 O3 S'
_chemical_formula_weight         298.34
_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_block_doi                 10.5517/ccdc.csd.cc2n7wng
_audit_creation_date             2024-08-18
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-14 deposited with the CCDC.	2026-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                80.525(2)
_cell_angle_beta                 71.175(2)
_cell_angle_gamma                76.443(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8557(4)
_cell_length_b                   13.0872(5)
_cell_length_c                   13.2877(6)
_cell_measurement_reflns_used    3947
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.355
_cell_measurement_theta_min      2.477
_cell_volume                     1410.36(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16587
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.174
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1138 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.7663.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.406
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5759
_refine_ls_number_restraints     268
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0687
_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^)+(0.0798P)^2^+1.7096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3973
_reflns_number_total             5759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00230g2.cif
_cod_data_source_block           mo_20241583_0m
_cod_depositor_comments
'Adding full bibliography for 7161050--7161051.cif.'
_cod_original_cell_volume        1410.37(11)
_cod_database_code               7161050
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.972
_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. Restrained distances
 C33-C21
 1.2 with sigma of 0.02
 C21-C20
 1.45 with sigma of 0.02
3. Rigid bond restraints
 O7, O6, C22, C25, C27, C32, C31, C29, C24, C26, C23, C30, C34, C33
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O7, O6, C18, C22, C28, C21, C33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O7 \\sim C22 \\sim C25 \\sim C27 \\sim C32 \\sim C31 \\sim C29 \\sim C24 \\sim
C23 \\sim C30 \\sim C34 \\sim C33: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
O7 \\sim C22 \\sim C21 \\sim C33 \\sim C28: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.01 within 2A
Uanis(C28) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(O6) = Uanis(C21)
Uanis(C21) = Uanis(O7)
Uanis(O7) = Uanis(C28)
5. Others
 Fixed Sof: O7(0.5) O6(0.5) C22(0.5) C32(0.5) C31(0.5) H31(0.5) C30(0.5)
 H30(0.5) C29(0.5) H29(0.5) C28(0.5) C21(0.5) C26(0.5) H26(0.5) C25(0.5)
 H25(0.5) C24(0.5) H24(0.5) C23(0.5) C27(0.5) H27A(0.5) H27B(0.5) H27C(0.5)
 C34(0.5) H34A(0.5) H34B(0.5) H34C(0.5) C33(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C36(H36), C13(H13), C40(H40), C14(H14), C38(H38),
 C15(H15), C39(H39), C37(H37), C7(H7), C31(H31), C30(H30), C29(H29), C26(H26),
 C25(H25), C24(H24), C6(H6), C8(H8)
6.b Fitted hexagon refined as free rotating group:
 C22(C32,C31,C30,C29,C28)
6.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C41(H41A,H41B,H41C), C27(H27A,H27B,H27C), C9(H9A,H9B,
 H9C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'