Electrophilic Activation of Molecular Bromine Mediated by I(III)
Sharp-Bucknall, Lachlan; _, Tania; Sceney, Marcus; Barwise, Lachlan; Dutton, Jason Laurence; Dalton Transactions  (2023) –; doi:10.1039/D3DT02999A

data_7714189
_publ_section_title
;
 Electrophilic Activation of Molecular Bromine Mediated by I(III)
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02999A
_journal_year                    2023
_chemical_formula_moiety         'C9 H4 F6 I N O7 S'
_chemical_formula_sum            'C9 H4 F6 I N O7 S'
_chemical_formula_weight         511.09
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2023-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.2460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.58430(10)
_cell_length_b                   10.5374(2)
_cell_length_c                   15.3990(2)
_cell_measurement_reflns_used    9664
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      71.1010
_cell_measurement_theta_min      4.5910
_cell_volume                     1554.83(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -63.00 -38.00   0.50    0.40    --  -38.50 115.00  34.00   50
  2  \w   -104.00 -48.00   0.50    0.40    --  -38.50-168.00 160.00  112
  3  \w   -104.00 -78.00   0.50    0.40    --  -38.50 168.00 179.00   52
  4  \w    -23.00   2.00   0.50    0.40    --  -38.50 115.00  34.00   50
  5  \w     30.00  78.00   0.50    0.40    --   42.60-115.00 -54.00   96
  6  \w     84.00 109.00   0.50    0.40    --   42.60-168.00 160.00   50
  7  \w     83.00 108.00   0.50    1.02    --  100.00-115.00 -54.00   50
  8  \w    119.00 157.00   0.50    1.02    --  100.00 115.00  34.00   76
  9  \w     86.00 111.00   0.50    1.02    --  100.00 168.00 179.00   50
 10  \w    -54.00 -19.00   0.50    0.40    --  -38.50  54.00   0.00   70
 11  \w    -52.00 -27.00   0.50    0.40    --  -38.50 -43.00 120.00   50
 12  \w    -74.00 -31.00   0.50    0.40    --  -38.50 -32.00-150.00   86
 13  \w    -11.00  23.00   0.50    0.40    --  -38.50  32.00 -90.00   68
 14  \w     -5.00  21.00   0.50    0.40    --  -38.50  54.00   0.00   52
 15  \w    -31.00  27.00   0.50    0.40    --  -38.50  32.00-120.00  116
 16  \w    -99.00 -73.00   0.50    0.40    --  -38.50 -43.00 120.00   52
 17  \w    -73.00 -24.00   0.50    0.40    --  -38.50 -65.00 120.00   98
 18  \w    -11.00  15.00   0.50    0.40    --  -38.50  65.00  30.00   52
 19  \w    -46.00 -15.00   0.50    0.40    --  -38.50  32.00 -90.00   62
 20  \w   -102.00 -77.00   0.50    0.40    --  -38.50 -65.00 120.00   50
 21  \w    -83.00 -32.00   0.50    0.40    --  -38.50 -32.00  30.00  102
 22  \w    -22.00  16.00   0.50    0.40    --   42.60 -32.00 -90.00   76
 23  \w     81.00 107.00   0.50    0.40    --   42.60  32.00   0.00   52
 24  \w      3.00  49.00   0.50    0.40    --   42.60 -43.00  60.00   92
 25  \w      8.00  49.00   0.50    0.40    --   42.60-104.00-150.00   82
 26  \w     20.00  75.00   0.50    0.40    --   42.60-104.00  30.00  110
 27  \w     44.00  69.00   0.50    0.40    --   42.60  32.00   0.00   50
 28  \w     20.00  46.00   0.50    0.40    --   42.60 -32.00 -90.00   52
 29  \w     75.00 101.00   0.50    1.02    --  100.00 -25.00 -90.00   52
 30  \w     33.00  58.00   0.50    1.02    --  100.00 -25.00 -90.00   50
 31  \w    120.00 150.00   0.50    1.02    --  100.00  42.00-120.00   60
 32  \w    126.00 152.00   0.50    1.02    --  100.00 145.00-180.00   52
 33  \w    139.00 164.00   0.50    1.02    --  100.00 145.00 -60.00   50
 34  \w     91.00 133.00   0.50    1.02    --  100.00 145.00 -60.00   84
 35  \w     80.00 119.00   0.50    1.02    --  100.00  68.00  30.00   78
 36  \w     27.00  53.00   0.50    1.02    --  100.00  -8.00  30.00   52
 37  \w     82.00 162.00   0.50    1.02    --  100.00  59.00 -60.00  160
 38  \w    111.00 137.00   0.50    1.02    --  100.00  33.00  60.00   52
 39  \w     80.00 108.00   0.50    1.02    --  100.00-117.00-120.00   56
 40  \w     38.00  85.00   0.50    1.02    --  100.00 -42.00-120.00   94
 41  \w     35.00 106.00   0.50    1.02    --  100.00-117.00 -90.00  142
 42  \w     87.00 113.00   0.50    1.02    --  100.00  42.00-120.00   52
 43  \w    114.00 139.00   0.50    1.02    --  100.00   8.00   0.00   50
 44  \w     35.00 109.00   0.50    1.02    --  100.00-117.00 150.00  148
 45  \w    105.00 136.00   0.50    1.02    --  100.00  96.00-180.00   62
 46  \w     68.00  94.00   0.50    1.02    --  100.00 -96.00 -30.00   52
 47  \w    112.00 137.00   0.50    1.02    --  100.00  96.00  30.00   50
 48  \w     71.00 126.00   0.50    1.02    --  100.00-145.00 150.00  110
 49  \w     33.00  91.00   0.50    1.02    --  100.00 -25.00   0.00  116
 50  \w    142.00 170.00   0.50    1.02    --  100.00  96.00  30.00   56
 51  \w     52.00 124.00   0.50    1.02    --  100.00 -77.00 -60.00  144
 52  \w     38.00  70.00   0.50    1.02    --  100.00-145.00 -60.00   64
 53  \w     65.00 111.00   0.50    1.02    --  100.00 -50.00 -90.00   92
 54  \w    103.00 165.00   0.50    1.02    --  100.00 117.00 -30.00  124
 55  \w     94.00 126.00   0.50    1.02    --  100.00-145.00 -90.00   64
 56  \w    107.00 149.00   0.50    1.02    --  100.00  96.00  60.00   84
 57  \w     72.00 109.00   0.50    1.02    --  100.00 -42.00  60.00   74
 58  \w     42.00  67.00   0.50    1.02    --  100.00 -96.00 -90.00   50
 59  \w     78.00 104.00   0.50    1.02    --  100.00 -96.00 -90.00   52
 60  \w     83.00 112.00   0.50    1.02    --  100.00 -87.00 -30.00   58
 61  \w     91.00 167.00   0.50    1.02    --  100.00  25.00  30.00  152
 62  \w     76.00 112.00   0.50    1.02    --  100.00 -68.00-150.00   72
 63  \w    139.00 164.00   0.50    1.02    --  100.00  68.00  30.00   50
 64  \w     52.00 108.00   0.50    1.02    --  100.00 -50.00   0.00  112
 65  \w     54.00  85.00   0.50    1.02    --  100.00  -8.00  30.00   62
 66  \w     93.00 129.00   0.50    1.02    --  100.00  -8.00  30.00   72
 67  \w    120.00 145.00   0.50    1.02    --  100.00  96.00  90.00   50
 68  \w    113.00 138.00   0.50    1.02    --  100.00  50.00 -30.00   50
 69  \w     72.00 106.00   0.50    1.02    --  100.00 -33.00-120.00   68
 70  \w    139.00 164.00   0.50    1.02    --  100.00 145.00-150.00   50
 71  \w     32.00  57.00   0.50    1.02    --  100.00 -96.00-150.00   50
 72  \w    134.00 159.00   0.50    1.02    --  100.00 117.00 150.00   50
 73  \w     39.00 108.00   0.50    1.02    --  100.00 -33.00  60.00  138
 74  \w     54.00 118.00   0.50    1.02    --  100.00 -68.00  90.00  128
 75  \w     65.00  90.00   0.50    1.02    --  100.00 -54.00  76.98   50
 76  \w     71.00  97.00   0.50    1.02    --  100.00   8.00   0.00   52
 77  \w     73.00  98.00   0.50    1.02    --  100.00-168.00 160.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0254898000
_diffrn_orient_matrix_UB_12      -0.0243052000
_diffrn_orient_matrix_UB_13      0.0970461000
_diffrn_orient_matrix_UB_21      -0.1586172000
_diffrn_orient_matrix_UB_22      -0.0014355000
_diffrn_orient_matrix_UB_23      -0.0184163000
_diffrn_orient_matrix_UB_31      0.0058780000
_diffrn_orient_matrix_UB_32      -0.1441373000
_diffrn_orient_matrix_UB_33      -0.0161532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17226
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.323
_diffrn_reflns_theta_min         5.086
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.183
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.033
_refine_diff_density_min         -1.129
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.00082(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3008
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0739P)^2^+2.1170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2757
_reflns_number_total             3008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02999a2.cif
_cod_data_source_block           li121
_cod_database_code               7714189
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C4 I S O7 F6 N H4'
_chemical_oxdiff_usercomment     '4-nitropifa+ tmsotf'
_shelx_estimated_absorpt_t_max   0.525
_shelx_estimated_absorpt_t_min   0.060
_reflns_odcompleteness_completeness 94.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C00O-F00L \\sim C00O-F00M
 with sigma of 0.02
 C00O-F1AB \\sim C00O-F1AC
 with sigma of 0.02
 C00O-F2 \\sim C00O-F2A
 with sigma of 0.02
3. Others
 Sof(F1AC)=Sof(F2A)=Sof(F00M)=1-FVAR(1)
 Sof(F00L)=Sof(F1AB)=Sof(F2)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00L(H00L)
;
_shelx_res_checksum              91656
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 8.140
_oxdiff_exptl_absorpt_empirical_full_min 0.205