Preparation of Pseudocyclic I(III) Reagents and Their Application in Selective Oxidations
Zhan, Xiangyu; You, Yong; Li, Cong; Du, Yunfei; Xiao, Dan; Xu, Lingzhi; Zhang, Shuoshuo; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01641J

data_7160915
_publ_section_title
;
 Preparation of Pseudocyclic I(III) Reagents and Their Application in
 Selective Oxidations
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01641J
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 I N O2, C F3 O3 S'
_chemical_formula_sum            'C15 H13 F3 I N O5 S'
_chemical_formula_weight         503.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-16
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-08-16 deposited with the CCDC.	2025-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   30.5483(10)
_cell_length_b                   19.5935(6)
_cell_length_c                   11.6668(3)
_cell_measurement_reflns_used    11442
_cell_measurement_temperature    110.4(8)
_cell_measurement_theta_max      30.7230
_cell_measurement_theta_min      2.1310
_cell_volume                     6983.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.4(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -77.00  -2.00   0.50    9.34    --   -6.68 -53.00 -48.00  150
  2  \w    -22.00  34.00   0.50    9.34    --    5.04 -99.00 -30.00  112
  3  \w    -22.00  25.00   0.50    9.34    --   -6.68 -99.00-180.00   94
  4  \w    -23.00  24.00   0.50    9.34    --   -6.68 -99.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123090000
_diffrn_orient_matrix_UB_12      -0.0211375000
_diffrn_orient_matrix_UB_13      0.0373741000
_diffrn_orient_matrix_UB_21      0.0137963000
_diffrn_orient_matrix_UB_22      -0.0094631000
_diffrn_orient_matrix_UB_23      -0.0462538000
_diffrn_orient_matrix_UB_31      0.0140381000
_diffrn_orient_matrix_UB_32      0.0278216000
_diffrn_orient_matrix_UB_33      0.0126822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12909
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.704
_diffrn_reflns_theta_min         2.138
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       plate
_exptl_crystal_F_000             3936
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4128
_refine_ls_number_restraints     193
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0215P)^2^+17.5349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0440
_refine_ls_wR_factor_ref         0.0457
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                3815
_reflns_number_total             4128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01641j2.cif
_cod_data_source_block           zxy_100k_b_auto
_cod_database_code               7160915
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.780
_olex2_refinement_description
;
1. Restrained distances
 H11-O11
 0.9 with sigma of 0.02
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C32(H32), C36(H36), C4(H4), C8(H8), C12(H12), C18(H18), C5(H5), C9(H9)
3.b Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_shelx_res_checksum              63762
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.175
_oxdiff_exptl_absorpt_empirical_full_min 0.864