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_7121965
_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_absolute_configuration ad
_chemical_formula_moiety         'C15 H11 F5 I O, Br'
_chemical_formula_sum            'C15 H11 Br F5 I O'
_chemical_formula_weight         509.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-06-05 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   38.2117(7)
_cell_length_b                   18.5754(5)
_cell_length_c                   9.3073(3)
_cell_measurement_reflns_used    7235
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      33.6040
_cell_measurement_theta_min      3.0500
_cell_volume                     6606.3(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 0.998
_diffrn_measured_fraction_theta_max 0.905
_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    -15.00  42.00   0.50   20.96    --   11.92 -99.00 120.00  114
  2  \w     -5.00  22.00   0.50   20.96    --  -13.32 -99.00  30.00   54
  3  \w    -20.00  22.00   0.50   20.96    --  -13.32 -99.00 120.00   84
  4  \w    -20.00  12.00   0.50   20.96    --  -13.32 -99.00 150.00   64
  5  \w    -82.00 -12.00   0.50   20.96    --  -13.32 -57.00   0.00  140
  6  \w    -28.00  46.00   0.50   20.96    --  -13.32  19.00   0.00  148
;
_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      -0.0052602000
_diffrn_orient_matrix_UB_12      -0.0365855000
_diffrn_orient_matrix_UB_13      0.0035868000
_diffrn_orient_matrix_UB_21      -0.0166336000
_diffrn_orient_matrix_UB_22      0.0107517000
_diffrn_orient_matrix_UB_23      0.0260954000
_diffrn_orient_matrix_UB_31      -0.0063319000
_diffrn_orient_matrix_UB_32      0.0021038000
_diffrn_orient_matrix_UB_33      -0.0715148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18693
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.678
_diffrn_reflns_theta_min         2.924
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.408
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.577
_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    2.047
_exptl_crystal_description       needle
_exptl_crystal_F_000             3872
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.032
_refine_diff_density_max         1.704
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details
;
 Flack x determined using 1696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5672
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.678
_reflns_number_gt                4730
_reflns_number_total             5672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc04558e2.cif
_cod_data_source_block           rs090418_1_2
_cod_depositor_comments
'Adding full bibliography for 7121965--7121967.cif.'
_cod_database_code               7121965
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C15H11BrF5IO
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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
 C13-H1
 1.897586 with sigma of 0.02
 I1-H1
 3.180853 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              25511
_olex2_date_sample_data_collection 2018-04-09
_olex2_date_sample_submission    2018-04-09
_olex2_submission_original_sample_id rs090418_1_2
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.806