Iridium-catalyzed regioselective B(3,6)-dialkenylation or B(4)-alkenylation of <i>o</i>-carboranes <i>via</i> B-H activation and 1,2-carbon migration of alkynes.
Zhang, Huifang; Cheng, Ruofei; Qiu, Zaozao; Xie, Zuowei; Chemical communications (Cambridge, England) 59 (2023) 740–743; doi:10.1039/d2cc05890a

data_7131106
_publ_section_title
;
 Iridium-catalyzed regioselective B(3,6)-dialkenylation or
 B(4)-alkenylation of <i>o</i>-carboranes <i>via</i> B-H activation and
 1,2-carbon migration of alkynes.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              740
_journal_page_last               743
_journal_paper_doi               10.1039/d2cc05890a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H29 B10 N'
_chemical_formula_sum            'C23 H29 B10 N'
_chemical_formula_weight         427.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-26 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                108.242(5)
_cell_angle_beta                 94.126(5)
_cell_angle_gamma                99.211(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1724(6)
_cell_length_b                   11.9352(10)
_cell_length_c                   13.5589(10)
_cell_measurement_reflns_used    5283
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      55.08
_cell_measurement_theta_min      3.46
_cell_volume                     1229.31(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14612
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.185
_diffrn_reflns_theta_min         3.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0867 before and 0.0519 after correction. The Ratio of minimum to maximum transmission is 0.8586. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+0.4784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3581
_reflns_number_total             4656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05890a2.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7131104--7131106.cif.'
_cod_database_code               7131106
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.986
_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. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
4.d Boron cage BH refined with riding coordinates:
 B3(H3), B4(H4), B6(H6A), B7(H7A), B8(H8A), B9(H9A), B10(H10), B11(H11A),
 B12(H12)
;
_shelx_res_checksum              52856
_shelx_hkl_checksum              61191
_olex2_submission_special_instructions 'No special instructions were received'