Monocarborane-stabilized iodonium salts enable regioselective B12-iodination of [CB<sub>11</sub>H<sub>12</sub>]<sup/>.
Jiang, Chennuo; Chen, Lianyu; Jin, Yujie; Liu, Jiyong; Zhang, Kang; Duttwyler, Simon; Dalton transactions (Cambridge, England : 2003) 55 (2026) 1109–1113; doi:10.1039/d5dt02721g

data_7720513
_publ_section_title
;
 Monocarborane-stabilized iodonium salts enable regioselective
 B12-iodination of [CB<sub>11</sub>H<sub>12</sub>]<sup/>.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1109
_journal_page_last               1113
_journal_paper_doi               10.1039/d5dt02721g
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         '2(C6 H15.5 B11 I0.5 N), 2(C5 H5 N)'
_chemical_formula_sum            'C22 H41 B22 I N4'
_chemical_formula_weight         726.31
_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             2024-05-11
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-07-14 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.8460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0340(3)
_cell_length_b                   16.9143(6)
_cell_length_c                   15.5499(5)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.680
_cell_measurement_theta_min      3.386
_cell_volume                     1822.80(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19520
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.740
_diffrn_reflns_theta_min         3.386
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    4.834
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8077.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+2.4493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3582
_reflns_number_total             4179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt02721g2.cif
_cod_data_source_block           240506_py_1
_cod_database_code               7720513
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All N(H) groups
2. Restrained distances
 N2-C11 \\sim N2A-C11A
 with sigma of 0.02
 N2-C7 \\sim N2A-C7A
 with sigma of 0.02
 C11-C7 \\sim C11A-C7A
 with sigma of 0.04
 C10-C8 \\sim C10A-C8A
 with sigma of 0.04
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 C9-C7 \\sim C9A-C7A
 with sigma of 0.04
 C10-C9 \\sim C10A-C9A
 with sigma of 0.02
 C9-C8 \\sim C9A-C8A
 with sigma of 0.02
 C11-C9 \\sim C11A-C9A
 with sigma of 0.04
 C8-C7 \\sim C8A-C7A
 with sigma of 0.02
 N2-C10 \\sim N2A-C10A
 with sigma of 0.04
 N2-C8 \\sim N2A-C8A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N2 \\sim C11 \\sim C7 \\sim H11A \\sim C10 \\sim C8 \\sim H7A \\sim H10A \\sim
C9 \\sim H8A \\sim H9A \\sim N2A \\sim C11A \\sim C7A \\sim H11B \\sim C10A
\\sim C8A \\sim H7AA \\sim H10B \\sim C9A \\sim H8AA \\sim H9AA: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
Uanis(N2A) = Uanis(N2)
4. Others
 Sof(N2A)=Sof(C11A)=Sof(H11B)=Sof(C10A)=Sof(H10B)=Sof(C9A)=Sof(H9AA)=Sof(C8A)=
 Sof(H8AA)=Sof(C7A)=Sof(H7AA)=1-FVAR(1)
 Sof(N2)=Sof(C11)=Sof(H11A)=Sof(C10)=Sof(H10A)=Sof(C9)=Sof(H9A)=Sof(C8)=
 Sof(H8A)=Sof(C7)=Sof(H7A)=FVAR(1)
 Fixed Sof: I1(0.5) H1A(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11A), C10(H10A), C9(H9A),
 C8(H8A), C7(H7A), C11A(H11B), C10A(H10B), C9A(H9AA), C8A(H8AA), C7A(H7AA)
5.b Fitted hexagon refined as free rotating group:
 N2(C11,C10,C9,C8,C7), N2A(C11A,C10A,C9A,C8A,C7A)
5.c Boron cage BH refined with riding coordinates:
 B1(H1A), B2(H2), B3(H3A), B4(H4A), B5(H5A), B6(H6A), B7(H7), B8(H8), B9(H9),
 B10(H10), B11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'