Substituent-controlled, Mild Oxidative Fluorination of Iodoarenes: Synthesis and Structural Study of Aryl I(III)- and I(V)-Fluorides
Häfliger, Joel; Pitts, Cody Ross; Bornemann, Dustin; Käser, Roland; Santschi, Nico; Charpentier, Julie; Otth, Elisabeth; Trapp, Nils; Verel, René; Lüthi, Hans Peter; Togni, Antonio; Chemical Science  (2019) –; doi:10.1039/C9SC02162K

data_1551254
_publ_section_title
;
 Substituent-controlled, Mild Oxidative Fluorination of Iodoarenes:
 Synthesis and Structural Study of Aryl I(III)- and I(V)-Fluorides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02162K
_journal_year                    2019
_chemical_formula_moiety         'C6 H4 F5 I'
_chemical_formula_sum            'C6 H4 F5 I'
_chemical_formula_weight         297.99
_chemical_name_systematic        Tetrafluoro(4-fluorophenyl)-\l5-iodane
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-30 deposited with the CCDC.    2019-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.90830(10)
_cell_length_b                   6.03640(10)
_cell_length_c                   14.1452(2)
_cell_measurement_reflns_used    7251
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.0690
_cell_measurement_theta_min      4.9720
_cell_volume                     760.338(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_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     36.00 125.00   0.50    0.40    --  105.75   0.00-120.00  178
  2  \w     98.00 178.00   0.50    0.40    --  105.75  38.00 -30.00  160
  3  \w     -7.00  75.00   0.50    0.10    --    0.88  38.00 -30.00  164
  4  \w     97.00 178.00   0.50    0.40    --  105.75  19.00  90.00  162
  5  \w     97.00 178.00   0.50    0.40    --  105.75  19.00  60.00  162
  6  \w     98.00 178.00   0.50    0.40    --  105.75  21.00  49.00  160
  7  \w     36.00 125.00   0.50    0.40    --  105.75   0.00 -30.00  178
  8  \w    -70.00  19.00   0.50    0.10    --   -0.88   0.00 150.00  178
  9  \w    -78.00   4.00   0.50    0.40    --  -70.00  38.00-120.00  164
 10  \w     35.00 119.00   0.50    0.40    --  105.75 -57.00-180.00  168
 11  \w    -63.00  22.00   0.50    0.10    --    0.88 -77.00 120.00  170
 12  \w     35.00 119.00   0.50    0.40    --  105.75 -57.00   0.00  168
 13  \w    -65.00  21.00   0.50    0.10    --   -0.88 -77.00  30.00  172
 14  \w   -134.00 -48.00   0.50    0.40    --  -70.00 -77.00-120.00  172
 15  \w   -134.00 -81.00   0.50    0.40    --  -70.00 -77.00   0.00  106
 16  \w   -138.00 -82.00   0.50    0.40    --  -70.00 -99.00 120.00  112
 17  \w     38.00 111.00   0.50    0.40    --  105.75 -99.00 150.00  146
 18  \w     35.00 121.00   0.50    0.40    --  105.75-125.00  30.00  172
 19  \w     38.00 111.00   0.50    0.40    --  105.75 -99.00-150.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1666482000
_diffrn_orient_matrix_UB_12      0.0590010000
_diffrn_orient_matrix_UB_13      0.0180524000
_diffrn_orient_matrix_UB_21      -0.0180299000
_diffrn_orient_matrix_UB_22      -0.0394035000
_diffrn_orient_matrix_UB_23      0.1066822000
_diffrn_orient_matrix_UB_31      0.0427579000
_diffrn_orient_matrix_UB_32      -0.2451731000
_diffrn_orient_matrix_UB_33      -0.0128282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7652
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.316
_diffrn_reflns_theta_min         5.796
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    33.528
_exptl_absorpt_correction_T_max  0.430
_exptl_absorpt_correction_T_min  0.049
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.603
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.808
_refine_diff_density_min         -1.573
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.7739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1586
_reflns_number_total             1608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02162k2.cif
_cod_data_source_block           lac130219_1_1
_cod_database_code               1551254
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C6H4F5I
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
;
_shelx_res_checksum              41152
_olex2_submission_original_sample_id lac130219_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.961
_oxdiff_exptl_absorpt_empirical_full_min 0.597