Orbital analysis of bonding in diarylhalonium salts and relevance to periodic trends in structure and reactivity.
Karandikar, Shubhendu S.; Bhattacharjee, Avik; Metze, Bryan E.; Javaly, Nicole; Valente, Edward J.; McCormick, Theresa M.; Stuart, David R.; Chemical science 13 (2022) 6532–6540; doi:10.1039/d2sc02332f

data_1567000
_publ_section_title
;
 Orbital analysis of bonding in diarylhalonium salts and relevance to
 periodic trends in structure and reactivity.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              6532
_journal_page_last               6540
_journal_paper_doi               10.1039/d2sc02332f
_journal_volume                  13
_journal_year                    2022
_chemical_formula_sum            'C47 H28 B F24 I'
_chemical_formula_weight         1186.4
_chemical_name_systematic
'Mesitylphenyliodonium tetra(3,5-ditrifluoromethylphenyl)borate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-11-24T07:00:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                79.342(5)
_cell_angle_beta                 83.823(5)
_cell_angle_gamma                68.734(5)
_cell_formula_units_Z            2
_cell_length_a                   12.5291(7)
_cell_length_b                   12.8808(8)
_cell_length_c                   15.7078(9)
_cell_measurement_reflns_used    11307
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      32.331
_cell_measurement_theta_min      2.259
_cell_volume                     2319.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    WinGX
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0105111
_diffrn_orient_matrix_UB_12      -0.0214849
_diffrn_orient_matrix_UB_13      -0.0397501
_diffrn_orient_matrix_UB_21      -0.0423125
_diffrn_orient_matrix_UB_22      -0.0251498
_diffrn_orient_matrix_UB_23      0.0126304
_diffrn_orient_matrix_UB_31      -0.0423817
_diffrn_orient_matrix_UB_32      0.0499276
_diffrn_orient_matrix_UB_33      -0.0194054
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23746
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.263
_diffrn_reflns_theta_min         1.974
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.87216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.35
_refine_diff_density_max         3.876
_refine_diff_density_min         -1.898
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         23746
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.157
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0
_reflns_number_gt                16836
_reflns_number_total             23746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02332f3.cif
_cod_data_source_block           up492_twin1_hklf5
_cod_depositor_comments
'Adding full bibliography for 1566998--1567000.cif.'
_cod_database_code               1567000
_refine_constraints
;
Two of the trifluoromethyl groups have large librations which were modelled
with two trigonal sets of three fluorines, major component 0.50 and 0.76
occupancy. C-F distances were constrained to 1.322 A; and F...F distances 
were constrained to 2.13 A.  30 restraints in all. 
;