Variable Metal Chelation Modes and Activation Sequence in Pd-Catalyzed B–H Poly-arylation of Carboranes
Cao, Hou-ji; Chen, Meng; Sun, Fangxiang; Zhao, Yue; Lu, Changsheng; Zhang, Xiaolei; Shi, Zhuangzhi; Yan, Hong; ACS Catalysis 11 (2021) 14047–14057; doi:10.1021/acscatal.1c04473

data_4519154
_publ_section_title
;
 Variable Metal Chelation Modes and Activation Sequence in Pd-Catalyzed
 B--H Poly-arylation of Carboranes
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              14047
_journal_page_last               14057
_journal_paper_doi               10.1021/acscatal.1c04473
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C33 H29 B10 F4 N O'
_chemical_formula_sum            'C33 H29 B10 F4 N O'
_chemical_formula_weight         639.67
_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   mixed
_audit_creation_date             2020-11-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.090(9)
_cell_angle_beta                 87.216(10)
_cell_angle_gamma                88.784(11)
_cell_formula_units_Z            4
_cell_length_a                   10.804(5)
_cell_length_b                   11.906(5)
_cell_length_c                   25.209(11)
_cell_measurement_reflns_used    5280
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.43
_cell_volume                     3238(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_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  0.0671
_diffrn_reflns_av_unetI/netI     0.1402
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15319
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.199
_diffrn_reflns_theta_max         24.199
_diffrn_reflns_theta_min         2.352
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.6509.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     894
_refine_ls_number_reflns         10141
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.2215
_refine_ls_R_factor_gt           0.1538
_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^)+(0.0979P)^2^+33.1374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3544
_refine_ls_wR_factor_ref         0.3904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5707
_reflns_number_total             10141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04473_si_002.cif
_cod_data_source_block           13k
_cod_depositor_comments
;

2025-07-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C66 H58 B20 F8 N2 O2'
_cod_original_formula_weight         1279.34
_cod_original_formula_moiety         '2(C33 H29 B10 F4 N O)'
_cod_original_formula_units_Z            2
_cod_database_code               4519154
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H11B of B11A, H10A of B10A, H12B of B12A, H8AA of B8A,
  H9AA of B9A, H9 of B9, H10 of B10, H8 of B8, H7 of B7, H12 of B12, H11 of B11,
   H7AA of B7A
 At 1.5 times of:
  H1A of B12A
2. Rigid bond restraints
 O1, C5
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7A), C8(H8A), C9(H9A), C11(H11A), C12(H12A), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27),
  C29(H29), C30(H30), C32(H32), C33(H33), C3A(H3A), C6A(H6A), C7A(H7AB),
 C8A(H8AB), C9A(H9AB), C11A(H11C), C12A(H12C), C14A(H14A), C15A(H15A),
 C17A(H17A), C18A(H18A), C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A),
 C26A(H26A), C27A(H27A), C29A(H29A), C30A(H30A), C32A(H32A), C33A(H33A)
3.b Boron cage BH refined with riding coordinates:
 C2(H2), B7(H7), B8(H8), B9(H9), B10(H10), B11(H11), B12(H12), C2A(H2A),
 B7A(H7AA), B8A(H8AA), B9A(H9AA), B10A(H10A), B11A(H11B), B12A(H12B)
;
_shelx_res_checksum              81854
_shelx_hkl_checksum              69856
_olex2_submission_special_instructions 'No special instructions were received'