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_7121966
_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         'C17 H15 Br F4 I O2, Cl'
_chemical_formula_sum            'C17 H15 Br Cl F4 I O2'
_chemical_formula_weight         569.55
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-10
_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                90
_cell_angle_beta                 95.6110(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.35480(10)
_cell_length_b                   8.05860(10)
_cell_length_c                   21.0488(2)
_cell_measurement_reflns_used    53837
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.1970
_cell_measurement_theta_min      4.2210
_cell_volume                     1916.82(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  '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 0.987
_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   -129.00 -40.00   0.50    0.27    --  -62.00 -72.00-177.10  178
  2  \w   -133.00 -44.00   0.50    0.27    --  -66.00 -72.00 -97.61  178
  3  \w   -122.00 -33.00   0.50    0.15    --  -54.00 -70.00 -71.12  178
  4  \w   -137.00 -48.00   0.50    0.27    --  -70.00 -72.00-130.26  178
  5  \w   -138.00 -49.00   0.50    0.27    --  -70.00 -70.00-161.82  178
  6  \w   -121.00 -32.00   0.50    0.15    --  -54.00 -73.00 -14.92  178
  7  \w   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  30.99  176
  8  \w   -138.00 -50.00   0.50    0.27    --  -70.00 -68.00  58.25  176
  9  \w   -125.00 -36.00   0.50    0.15    --  -58.00 -73.00 117.81  178
 10  \w   -137.00 -49.00   0.50    0.27    --  -70.00 -71.00 155.63  176
 11  \w   -137.00 -48.00   0.50    0.27    --  -70.00 -73.00  87.33  178
 12  \w   -137.00 -49.00   0.50    0.27    --  -70.00 -71.00  92.45  176
 13  \w   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  17.08  176
 14  \w   -140.00 -52.00   0.50    0.27    --  -70.00 -63.00 -36.88  176
 15  \w   -137.00 -48.00   0.50    0.27    --  -70.00 -72.00 -72.20  178
 16  \w   -139.00 -51.00   0.50    0.27    --  -70.00 -66.00-121.24  176
 17  \w   -139.00 -50.00   0.50    0.27    --  -70.00 -67.00 -59.09  178
 18  \w   -139.00 -51.00   0.50    0.27    --  -70.00 -65.00  -8.52  176
 19  \w   -138.00 -50.00   0.50    0.27    --  -70.00 -68.00 116.51  176
 20  \w     52.00  81.00   0.50    0.27    --  110.00 -57.00-150.00   58
 21  \w     48.00  80.00   0.50    0.27    --  110.00 -57.00   0.00   64
 22  \w     44.00  72.00   0.50    0.27    --  110.00 -77.00 -30.00   56
 23  \w    107.00 133.00   0.50    0.27    --  110.00 -77.00 -30.00   52
 24  \w    -50.00  40.00   0.50    0.15    --  -26.00  79.00 -98.85  180
 25  \w    -73.00  17.00   0.50    0.15    --  -49.37  77.00  90.00  180
 26  \w   -124.00 -36.00   0.50    0.15    --  -49.37 -44.00 141.06  176
 27  \w   -124.00 -36.00   0.50    0.15    --  -49.37 -44.00  75.92  176
 28  \w     52.00 110.00   0.50    0.27    --  110.00 -77.00 120.00  116
 29  \w     13.00  43.00   0.50    0.15    --   38.00  80.00-142.16   60
 30  \w     14.00  44.00   0.50    0.15    --   38.00  79.00 -46.43   60
 31  \w     37.00 125.00   0.50    0.15    --   49.37  38.00-150.00  176
 32  \w     34.00 121.00   0.50    0.15    --   49.37  57.00-120.00  174
 33  \w     21.00 109.00   0.50    0.15    --   42.00  72.00 129.54  176
 34  \w     37.00 125.00   0.50    0.15    --   49.37  38.00 150.00  176
 35  \w     29.00 117.00   0.50    0.15    --   50.00  72.00  63.76  176
 36  \w     12.00  40.00   0.50    0.15    --   38.00  82.00 -30.03   56
 37  \w     86.00 113.00   0.50    0.27    --  110.00  77.00  30.00   54
 38  \w     87.00 177.00   0.50    0.27    --  110.00  77.00   0.00  180
 39  \w     86.00 120.00   0.50    0.27    --  110.00  77.00  90.00   68
 40  \w    129.00 170.00   0.50    0.27    --  110.00  77.00  30.00   82
 41  \w    125.00 168.00   0.50    0.27    --  110.00  77.00  90.00   86
 42  \w    -95.00  -9.00   0.50    0.27    --  -70.00 125.00-150.00  172
 43  \w    134.00 174.00   0.50    0.27    --  110.00  77.00-150.00   80
 44  \w     59.00 120.00   0.50    0.15    --   49.37 178.00-150.00  122
 45  \w    102.00 129.00   0.50    0.27    --  110.00  57.00 -90.00   54
 46  \w     88.00 115.00   0.50    0.27    --  110.00  77.00-150.00   54
 47  \w     67.00 155.00   0.50    0.27    --   86.00  66.00-176.03  176
 48  \w     59.00 148.00   0.50    0.15    --   78.00  65.00  34.57  178
 49  \w     72.00  98.00   0.50    0.27    --   90.00  63.00 162.48   52
 50  \w     57.00 145.00   0.50    0.15    --   78.00  72.00  66.97  176
 51  \w     56.00 145.00   0.50    0.15    --   78.00  73.00   9.97  178
 52  \w    122.00 169.00   0.50    0.27    --   94.00  44.00 -98.83   94
 53  \w     81.00 106.00   0.50    0.27    --   94.00  44.00 -98.83   50
 54  \w     96.00 149.00   0.50    0.27    --  110.00  57.00-150.00  106
 55  \w     87.00 177.00   0.50    0.27    --  110.00  77.00 -60.00  180
 56  \w    120.00 161.00   0.50    0.27    --   94.00  45.00 153.06   82
 57  \w     81.00 117.00   0.50    0.27    --   94.00  45.00 153.06   72
 58  \w     99.00 125.00   0.50    0.27    --  110.00  38.00 120.00   52
 59  \w     86.00 176.00   0.50    0.27    --  110.00  77.00  60.00  180
 60  \w    127.00 174.00   0.50    0.27    --  110.00  77.00 -90.00   94
 61  \w     94.00 120.00   0.50    0.27    --  110.00  57.00 -60.00   52
 62  \w     87.00 113.00   0.50    0.27    --  110.00  77.00 -90.00   52
 63  \w     94.00 137.00   0.50    0.27    --  110.00  57.00 -30.00   86
 64  \w    148.00 174.00   0.50    0.27    --  110.00  57.00 -30.00   52
 65  \w     98.00 131.00   0.50    0.27    --  110.00  38.00  90.00   66
 66  \w     97.00 178.00   0.50    0.27    --  110.00  57.00 120.00  162
 67  \w     99.00 152.00   0.50    0.27    --  110.00  38.00  60.00  106
 68  \w    137.00 177.00   0.50    0.27    --  110.00  77.00-120.00   80
 69  \w     86.00 170.00   0.50    0.27    --  110.00  77.00-180.00  168
 70  \w     90.00 116.00   0.50    0.27    --  110.00  77.00-120.00   52
 71  \w     94.00 144.00   0.50    0.27    --  110.00  57.00-120.00  100
 72  \w    146.00 172.00   0.50    0.27    --  110.00  77.00 -30.00   52
 73  \w     86.00 141.00   0.50    0.27    --  110.00  77.00 -30.00  110
 74  \w     87.00 170.00   0.50    0.27    --  110.00  77.00 150.00  166
 75  \w     42.00 110.00   0.50    0.27    --  110.00 -99.00  30.00  136
 76  \w     44.00 110.00   0.50    0.27    --  110.00 -99.00 120.00  132
 77  \w     69.00 122.00   0.50    0.27    --  110.00-125.00 -30.00  106
 78  \w     41.00  91.00   0.50    0.27    --  110.00 -99.00-120.00  100
 79  \w     49.00  95.00   0.50    0.27    --  110.00 -99.00 -30.00   92
;
_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      -0.0776237000
_diffrn_orient_matrix_UB_12      -0.0343648000
_diffrn_orient_matrix_UB_13      0.0546073000
_diffrn_orient_matrix_UB_21      0.1119529000
_diffrn_orient_matrix_UB_22      -0.0152290000
_diffrn_orient_matrix_UB_23      0.0472671000
_diffrn_orient_matrix_UB_31      -0.0051109000
_diffrn_orient_matrix_UB_32      0.1874604000
_diffrn_orient_matrix_UB_33      0.0138378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.729
_diffrn_reflns_theta_min         4.221
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.295
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.186
_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    1.974
_exptl_crystal_description       plank
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0202
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0207P)^2^+2.9419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4043
_reflns_number_total             4118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04558e2.cif
_cod_data_source_block           rs091117_1_1
_cod_depositor_comments
'Adding full bibliography for 7121965--7121967.cif.'
_cod_database_code               7121966
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C17H15BrClF4IO2
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.93 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              82433
_olex2_date_sample_data_collection 2017-11-09
_olex2_date_sample_submission    2017-11-09
_olex2_submission_original_sample_id rs091117_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 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.802