Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles.
Gruber, Stefan; Ametamey, Simon M.; Schibli, Roger; Chemical communications (Cambridge, England) 54 (2018) 8999–9002; doi:10.1039/c8cc04558e

data_7121967
_publ_section_title
;
 Unexpected reactivity of cyclic perfluorinated iodanes with
 electrophiles.
;
_journal_issue                   65
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8999
_journal_page_last               9002
_journal_paper_doi               10.1039/c8cc04558e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C15 H9 Br Cl F4 I O3'
_chemical_formula_sum            'C15 H9 Br Cl F4 I O3'
_chemical_formula_weight         555.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                74.798(2)
_cell_angle_beta                 84.253(2)
_cell_angle_gamma                86.584(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9867(2)
_cell_length_b                   8.2391(2)
_cell_length_c                   13.6897(2)
_cell_measurement_reflns_used    25100
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.1290
_cell_measurement_theta_min      3.3470
_cell_volume                     864.41(3)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XT (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 0.9785
_diffrn_measured_fraction_theta_max 0.9785
_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     21.00 110.00   0.50    0.10    --   42.00  71.00  -7.95  178
  2  \w     37.00 125.00   0.50    0.10    --   49.37  38.00 150.00  176
  3  \w     34.00 121.00   0.50    0.10    --   49.37  57.00  90.00  174
  4  \w     20.00 109.00   0.50    0.10    --   42.00  73.00 151.88  178
  5  \w     37.00 125.00   0.50    0.10    --   49.37  38.00 -30.00  176
  6  \w     37.00 125.00   0.50    0.10    --   49.37  38.00  30.00  176
  7  \w     86.00 177.00   0.50    0.14    --  110.00  77.00  60.00  182
  8  \w     86.00 177.00   0.50    0.14    --  110.00  77.00  90.00  182
  9  \w     33.00 121.00   0.50    0.10    --   54.00  72.00  13.49  176
 10  \w     53.00 142.00   0.50    0.10    --   74.00  70.00 -20.82  178
 11  \w     32.00 121.00   0.50    0.10    --   54.00  73.00-165.02  178
 12  \w     86.00 177.00   0.50    0.14    --  110.00  77.00 -60.00  182
 13  \w     86.00 177.00   0.50    0.14    --  110.00  77.00 -30.00  182
 14  \w     86.00 177.00   0.50    0.14    --  110.00  77.00-180.00  182
 15  \w     98.00 178.00   0.50    0.14    --  110.00  38.00-150.00  160
 16  \w     86.00 177.00   0.50    0.14    --  110.00  77.00-150.00  182
 17  \w     94.00 178.00   0.50    0.14    --  110.00  57.00 -90.00  168
 18  \w     94.00 178.00   0.50    0.14    --  110.00  57.00 -30.00  168
 19  \w     94.00 178.00   0.50    0.14    --  110.00  57.00  30.00  168
 20  \w     86.00 177.00   0.50    0.14    --  110.00  77.00 120.00  182
 21  \w     86.00 177.00   0.50    0.14    --  110.00  77.00 150.00  182
 22  \w    -94.00  -3.00   0.50    0.14    --  -70.00  77.00 -60.00  182
 23  \w   -140.00 -51.00   0.50    0.14    --  -70.00 -64.00   3.87  178
 24  \w   -137.00 -48.00   0.50    0.14    --  -70.00 -73.00-112.17  178
 25  \w   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 -45.80  178
 26  \w   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00  78.26  178
 27  \w   -138.00 -49.00   0.50    0.14    --  -70.00 -70.00  30.82  178
 28  \w   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 -56.88  178
 29  \w   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00 123.24  178
 30  \w   -137.00 -49.00   0.50    0.14    --  -70.00 -71.00-158.01  176
 31  \w   -125.00 -37.00   0.50    0.10    --  -49.37 -19.00 -60.00  176
 32  \w   -138.00 -49.00   0.50    0.14    --  -70.00 -69.00 137.26  178
 33  \w   -137.00 -48.00   0.50    0.14    --  -70.00 -72.00 106.94  178
 34  \w   -138.00 -49.00   0.50    0.14    --  -70.00 -70.00  57.87  178
 35  \w   -125.00 -36.00   0.50    0.10    --  -58.00 -72.00  45.60  178
 36  \w   -137.00 -48.00   0.50    0.14    --  -70.00 -73.00-102.37  178
 37  \w   -140.00 -52.00   0.50    0.14    --  -70.00 -63.00 -93.12  176
 38  \w    -26.00  49.00   0.50    0.10    --   49.37 -38.00  90.00  150
 39  \w     38.00  84.00   0.50    0.14    --  110.00 -57.00 -90.00   92
 40  \w     94.00 178.00   0.50    0.14    --  110.00  57.00 -60.00  168
 41  \w     94.00 178.00   0.50    0.14    --  110.00  57.00 150.00  168
 42  \w     98.00 178.00   0.50    0.14    --  110.00  38.00  90.00  160
 43  \w     98.00 178.00   0.50    0.14    --  110.00  38.00-120.00  160
 44  \w     86.00 177.00   0.50    0.14    --  110.00  77.00   0.00  182
 45  \w     98.00 178.00   0.50    0.14    --  110.00  38.00 -90.00  160
 46  \w     86.00 177.00   0.50    0.14    --  110.00  77.00-120.00  182
 47  \w     94.00 178.00   0.50    0.14    --  110.00  57.00   0.00  168
 48  \w     86.00 177.00   0.50    0.14    --  110.00  77.00  30.00  182
 49  \w    -95.00  -9.00   0.50    0.14    --  -70.00 125.00  30.00  172
 50  \w    -38.00 -12.00   0.50    0.10    --   14.00 131.00 158.07   52
 51  \w      7.00  36.00   0.50    0.10    --   34.00  85.00  85.51   58
 52  \w      7.00  36.00   0.50    0.10    --   34.00  85.00-127.84   58
 53  \w      7.00  36.00   0.50    0.10    --   34.00  85.00 -21.21   58
 54  \w     59.00 120.00   0.50    0.10    --   49.37 178.00   0.00  122
 55  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00-150.00  140
 56  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00-180.00  140
 57  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00 -90.00  140
 58  \w     39.00 122.00   0.50    0.14    --  110.00-125.00-180.00  166
 59  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00 -60.00  140
 60  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00  30.00  140
 61  \w     40.00 110.00   0.50    0.14    --  110.00 -99.00  90.00  140
 62  \w   -121.00 -33.00   0.50    0.10    --  -54.00 -71.00 130.59  176
 63  \w   -125.00 -36.00   0.50    0.10    --  -58.00 -73.00-131.44  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33322
_diffrn_reflns_theta_full        79.8599
_diffrn_reflns_theta_max         79.86
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    19.206
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.270
_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    2.1340
_exptl_crystal_description       plate
_exptl_crystal_F_000             528.7898
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.8921
_refine_diff_density_min         -1.3032
_refine_diff_density_rms         0.1262
_refine_ls_d_res_high            0.7832
_refine_ls_d_res_low             13.1597
_refine_ls_goodness_of_fit_ref   1.0775
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0773
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.0013
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+2.2325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3576
_reflns_number_total             3694
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8cc04558e2.cif
_cod_data_source_block           rs300118_1_1
_cod_depositor_comments
'Adding full bibliography for 7121965--7121967.cif.'
_cod_database_code               7121967
_olex2_refinement_description
;
;
_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
;