Metal-free iodosulfonylation of alkynes to access (<i>E</i>)-β-iodovinyl sulfones in water.
Peng, Guiting; Wei, Fang; Bai, Jiang; Ding, Haixin; Yu, Xin; Xiao, Qiang; Organic & biomolecular chemistry 23 (2025) 5301–5306; doi:10.1039/d5ob00483g

data_7160547
_publ_section_title
;
 Metal-free iodosulfonylation of alkynes to access
 (<i>E</i>)-&#x3b2;-iodovinyl sulfones in water.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5301
_journal_page_last               5306
_journal_paper_doi               10.1039/d5ob00483g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H15 I O2 S'
_chemical_formula_sum            'C16 H15 I O2 S'
_chemical_formula_weight         398.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-06 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5284(3)
_cell_length_b                   9.1429(4)
_cell_length_c                   31.8213(17)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    655(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.56
_cell_volume                     1608.43(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      655.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0721
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            12643
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         2.560
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1586 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.5453.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.068(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3501
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00483g2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160547.cif.'
_cod_database_code               7160547
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.677
_shelx_estimated_absorpt_t_min   0.641
_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.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00E(H00F), C00F(H00G),
 C00G(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00D(H00C,H00D,H00E), C00K(H00K,H00L,H00M)
;
_shelx_res_checksum              14599
_olex2_submission_special_instructions 'No special instructions were received'