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_7161051
_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         '1(C21 H12 O3 S2)'
_chemical_formula_sum            'C21 H12 O3 S2'
_chemical_formula_weight         376.43
_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     iterative
_audit_creation_date             2025-07-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-17 deposited with the CCDC.	2026-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                103.7620(10)
_cell_angle_beta                 94.4470(10)
_cell_angle_gamma                111.6600(10)
_cell_formula_units_Z            4
_cell_length_a                   9.6461(3)
_cell_length_b                   11.6280(4)
_cell_length_c                   16.8233(6)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.27
_cell_volume                     1674.58(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24676
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.271
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.045
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8282.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         5722
_refine_ls_number_restraints     887
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+3.4952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5548
_reflns_number_total             5722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00230g2.cif
_cod_data_source_block           0718-1
_cod_depositor_comments
'Adding full bibliography for 7161050--7161051.cif.'
_cod_database_code               7161051
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.711
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained planarity
 O1A, O2A, O3A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O5 \\sim O6 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim
C28 \\sim C29 \\sim C30 \\sim O4A \\sim O5A \\sim O6A \\sim C22A \\sim C23A
\\sim C24A \\sim C25A \\sim C26A \\sim C27A \\sim C28A \\sim C29A \\sim C30A
\\sim O4 \\sim S3: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
S1 \\sim O1A \\sim O2A \\sim O3A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim
C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim O1 \\sim O2 \\sim O3 \\sim C1
\\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O1A) \\sim Ueq, Uanis(O3A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Same fragment restrains
{S3, O4A, O5A, O6A, C22A, C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A} sigma
for 1-2: 0.01, 1-3: 0.01
as in
{S3, O4, O5, O6, C22, C23, C24, C25, C26, C27, C28, C29, C30}
{S1, O1A, O2A, O3A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A} sigma for 1-2:
0.01, 1-3: 0.01
as in
{S1, O1, O2, O3, C1, C2, C3, C4, C5, C6, C7, C8, C9}
5. Others
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-
 FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=FVAR(1)
 Sof(O4A)=Sof(O5A)=Sof(O6A)=Sof(C22A)=Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(C26A)=
 Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=
 Sof(H30A)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(O6)=Sof(C22)=Sof(C23)=Sof(C24)=Sof(C25)=Sof(C26)=Sof(C27)=
 Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C27(H27), C28(H28), C29(H29), C30(H30),
  C33(H33), C34(H34), C35(H35), C36(H36), C39(H39), C40(H40), C41(H41),
 C42(H42), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A), C6A(H6A), C7A(H7A),
 C8A(H8A), C9A(H9A)
;
_shelx_res_checksum              10395
_olex2_submission_special_instructions 'No special instructions were received'