Regioselective B2–6 penta-iodination of the [CB11H12]– monocarborane cluster by palladium catalysis
Lin, Chuhao; Jin, Yujie; Sun, Jizeng; Ye, Zehua; Chen, Tao; Liu, Jiyong; Duttwyler, Simon; Dalton Transactions  (2023) –; doi:10.1039/D3DT02275G

data_7713631
_publ_section_title
;
 Regioselective B2--6 penta-iodination of the [CB11H12]-- monocarborane
 cluster by palladium catalysis
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02275G
_journal_year                    2023
_chemical_formula_moiety         'C H6 B11 I6, C8 H20 N'
_chemical_formula_sum            'C9 H26 B11 I6 N'
_chemical_formula_weight         1028.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.216(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4164(6)
_cell_length_b                   16.9039(12)
_cell_length_c                   17.2551(12)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.36
_cell_volume                     2746.5(3)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58375
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_min         2.361
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.786
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0759 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.8426.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.270
_refine_diff_density_min         -1.578
_refine_diff_density_rms         0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         8376
_refine_ls_number_restraints     324
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0524
_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^)+65.8973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7006
_reflns_number_total             8376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02275g2.cif
_cod_data_source_block           mo_221109_lch_12_i_0m
_cod_database_code               7713631
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C4 \\sim N1A-C4A
 with sigma of 0.02
 N1-C6 \\sim N1A-C6A
 with sigma of 0.02
 N1-C8 \\sim N1A-C8A
 with sigma of 0.02
 N1-C2 \\sim N1A-C2A
 with sigma of 0.02
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C4-C2 \\sim C4A-C2A
 with sigma of 0.04
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C4-C8 \\sim C4A-C8A
 with sigma of 0.04
 C6-C2 \\sim C6A-C2A
 with sigma of 0.04
 C8-C2 \\sim C8A-C2A
 with sigma of 0.04
 N1-C3 \\sim N1A-C3A
 with sigma of 0.04
 N1-C7 \\sim N1A-C7A
 with sigma of 0.04
 N1-C5 \\sim N1A-C5A
 with sigma of 0.04
 N1-C9 \\sim N1A-C9A
 with sigma of 0.04
3. Rigid bond restraints
 N1, C2, C3, C4, C5, C6, C7, C8, C9, N1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
N1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim N1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim C7A \\sim C8A
\\sim C9A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
5. Others
 Sof(N1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C6A)=
 Sof(H6AA)=Sof(H6AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(C8A)=Sof(H8AA)=
 Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=1-FVAR(1)
 Sof(N1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H9C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C8(H8A,H8B), C2A(H2AA,H2AB), C4A(H4AA,
 H4AB), C6A(H6AA,H6AB), C8A(H8AA,H8AB)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C3A(H3AA,
 H3AB,H3AC), C5A(H5AA,H5AB,H5AC), C7A(H7AA,H7AB,H7AC), C9A(H9AA,H9AB,H9AC)
6.c Boron cage BH refined with riding coordinates:
 C1(H1), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10)
;
_shelx_res_checksum              11907
_olex2_submission_special_instructions 'No special instructions were received'