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_7131105
_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         'C25 H33 B10 N'
_chemical_formula_sum            'C25 H33 B10 N'
_chemical_formula_weight         455.62
_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             2021-03-18
_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                90
_cell_angle_beta                 92.277(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7181(3)
_cell_length_b                   18.0152(5)
_cell_length_c                   13.7615(4)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.95
_cell_measurement_theta_min      3.59
_cell_volume                     2655.09(13)
_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      172.98
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28213
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.960
_diffrn_reflns_theta_min         3.591
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1615 before and 0.0839 after correction. The Ratio of minimum to maximum transmission is 0.7192. The \l/2 correction factor is Not present.'
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0630P)^2^+1.1645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4205
_reflns_number_total             5039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05890a2.cif
_cod_data_source_block           6e
_cod_depositor_comments
;
Adding full bibliography for 7131104--7131106.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         227.81
_cod_original_formula_moiety         '0.5(C25 H33 B10 N)'
_cod_original_formula_units_Z            8
_cod_original_formula_sum        'C12.50 H16.50 B5 N0.50'
_cod_database_code               7131105
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.954
_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.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
2.e Boron cage BH refined with riding coordinates:
 B3(H3A), B5(H5), B6(H6), B7(H7), B8(H8A), B9(H9A), B10(H10A), B11(H11A),
 B12(H12A)
;
_shelx_res_checksum              41896
_shelx_hkl_checksum              98325
_olex2_submission_special_instructions 'No special instructions were received'