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_1551253
_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         'C9 H10 F3 I O'
_chemical_formula_sum            'C9 H10 F3 I O'
_chemical_formula_weight         318.07
_chemical_name_systematic
1,1,1-Trifluoro-3,3-dimethyl-1,3-dihydro-1\l5-benzo[d][1,2]iodaoxole
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-26
_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                 116.7259(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.2690(11)
_cell_length_b                   10.8007(9)
_cell_length_c                   13.7770(11)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.41
_cell_volume                     2029.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33393
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.619
_diffrn_reflns_theta_min         1.493
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.164
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.082
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.025
_refine_diff_density_max         2.825
_refine_diff_density_min         -2.298
_refine_diff_density_rms         0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         6167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4966
_reflns_number_total             6167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc02162k2.cif
_cod_data_source_block           ep_6041
_cod_database_code               1551253
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.790
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5648
 0.4352
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B)
3.b Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,
 H9BC)
;
_shelx_res_checksum              84683
_olex2_date_sample_data_collection 2014-09-25
_olex2_date_sample_submission    2014-09-25
_olex2_submission_original_sample_id ep_6041
_olex2_submission_special_instructions 'No special instructions were received'