Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles.
Lubriks, Dmitrijs; Sokolovs, Igors; Suna, Edgars; Organic letters 13 (2011) 4324–4327; doi:10.1021/ol201665c

data_1502368
_publ_section_title
;
 Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of
 pyrroles.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4324
_journal_page_last               4327
_journal_paper_doi               10.1021/ol201665c
_journal_volume                  13
_journal_year                    2011
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C18 H16 Br I N O2, C2 H3 O2 '
_chemical_formula_sum            'C20 H19 Br I N O4'
_chemical_formula_weight         544.179
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                88.038(2)
_cell_angle_beta                 75.417(2)
_cell_angle_gamma                87.0530(12)
_cell_formula_units_Z            2
_cell_length_a                   8.2215(2)
_cell_length_b                   9.6598(4)
_cell_length_c                   13.0019(3)
_cell_measurement_reflns_used    6816
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      0.9
_cell_volume                     997.76(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.08936
_diffrn_orient_matrix_UB_12      0.06316
_diffrn_orient_matrix_UB_13      0.06208
_diffrn_orient_matrix_UB_21      0.03899
_diffrn_orient_matrix_UB_22      -0.09188
_diffrn_orient_matrix_UB_23      0.02806
_diffrn_orient_matrix_UB_31      0.02891
_diffrn_orient_matrix_UB_32      -0.00824
_diffrn_orient_matrix_UB_33      -0.07359
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7298
_diffrn_reflns_theta_full        29.5
_diffrn_reflns_theta_max         29.5
_diffrn_reflns_theta_min         2.5
_exptl_absorpt_coefficient_mu    3.632
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
By Gaussian integration based on twelve indexed crystal faces (NUMABS;
Coppens, 1970)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.32
_refine_diff_density_min         -1.87
_refine_diff_density_rms         0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.703
_refine_ls_goodness_of_fit_gt    1.378
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.055
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.148
_refine_ls_wR_factor_gt          0.070
_refine_ls_wR_factor_ref         0.070
_reflns_d_resolution_high        0.61
_reflns_d_resolution_low         1.99
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              17
_reflns_limit_l_min              -16
_reflns_number_gt                4058
_reflns_number_total             5297
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            ol201665c_si_002.cif
_cod_data_source_block           DLG181
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C20 H19 Br I N O4 '
_cod_database_code               1502368