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_7720516
_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         'C14 H20 I N4, C H11 B11 I'
_chemical_formula_sum            'C15 H31 B11 I2 N4'
_chemical_formula_weight         640.15
_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             2024-11-19
_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                 106.617(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9066(6)
_cell_length_b                   8.9852(4)
_cell_length_c                   21.3656(11)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      28.197
_cell_measurement_theta_min      2.475
_cell_volume                     2742.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_environment      N~2~
_diffrn_ambient_temperature      298.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Ius3.0'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            49167
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_min         1.958
_diffrn_source                   'Ius X-ray source'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              Ius
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.8258.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_refine_diff_density_max         1.676
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0245P)^2^+5.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5684
_reflns_number_total             6784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt02721g2.cif
_cod_data_source_block           241118_zk_exp_cly_8
_cod_database_code               7720516
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.619
_shelx_estimated_absorpt_t_min   0.467
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Boron cage BH refined with riding coordinates:
 C00H(H00H), B2(H2A), B3(H3), B4(H4A), B5(H5A), B6(H6), B7(H7), B8(H8A),
 B9(H9A), B10(H10), B11(H11A)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'