Palladium-catalyzed B7-11 penta-arylation of the {CB<sub>11</sub>} monocarborane cluster.
Jin, Yujie; Sun, Jizeng; Zhang, Kang; Liu, Jiyong; Wörle, Michael; Duttwyler, Simon; Chemical communications (Cambridge, England) 59 (2022) 67–70; doi:10.1039/d2cc05422a

data_7131039
_publ_section_title
;
 Palladium-catalyzed B7-11 penta-arylation of the {CB<sub>11</sub>}
 monocarborane cluster.
;
_journal_issue                   1
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              67
_journal_page_last               70
_journal_paper_doi               10.1039/d2cc05422a
_journal_volume                  59
_journal_year                    2022
_chemical_formula_moiety         'C32 H27 B11 Br5 O2, 1.837(C3 H6 O), C8 H20 N'
_chemical_formula_sum            'C45.51 H58.03 B11 Br5 N O3.84'
_chemical_formula_weight         1198.89
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-09-12 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                67.0770(10)
_cell_angle_beta                 74.7490(10)
_cell_angle_gamma                69.0300(10)
_cell_formula_units_Z            2
_cell_length_a                   12.7612(3)
_cell_length_b                   14.7509(3)
_cell_length_c                   16.4625(4)
_cell_measurement_reflns_used    9056
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.35
_cell_volume                     2637.44(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            55008
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.871
_diffrn_reflns_theta_min         2.345
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.850
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0907 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.6620.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             1198
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.412
_refine_diff_density_min         -2.149
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         12560
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0375P)^2^+6.9626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10145
_reflns_number_total             12560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05422a2.cif
_cod_data_source_block           191101_jyj_183_0m
_cod_depositor_comments
'Adding full bibliography for 7131036--7131040.cif.'
_cod_database_code               7131039
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.513
_shelx_estimated_absorpt_t_min   0.401
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 N1-C32 \\sim N1-C32A
 with sigma of 0.02
 N1-C34 \\sim N1-C34A
 with sigma of 0.02
 N1-C36 \\sim N1-C36A
 with sigma of 0.02
 N1-C38 \\sim N1-C38A
 with sigma of 0.02
 C37-C36 \\sim C37-C36A
 with sigma of 0.02
 C33-C32 \\sim C33-C32A
 with sigma of 0.02
 C35-C34 \\sim C35-C34A
 with sigma of 0.02
 C39-C38 \\sim C39-C38A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C34 \\sim C34A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.084 within 1.7A
Uiso(O4) = Uiso(C1A) = Uiso(C1B) = Uiso(C1C) = Uiso(O5) = Uiso(C1D) = Uiso(C1E)
= Uiso(C1F)
4. Others
 Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(H37D)=
 Sof(H37E)=Sof(H37F)=Sof(H39D)=Sof(H39E)=Sof(H39F)=Sof(C32A)=Sof(H32C)=
 Sof(H32D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C36A)=Sof(H36C)=Sof(H36D)=
 Sof(C38A)=Sof(H38C)=Sof(H38D)=1-FVAR(1)
 Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(H37A)=
 Sof(H37B)=Sof(H37C)=Sof(H39A)=Sof(H39B)=Sof(H39C)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C38)=Sof(H38A)=
 Sof(H38B)=FVAR(1)
 Sof(O4)=Sof(C1A)=Sof(C1B)=Sof(H1BA)=Sof(H1BC)=Sof(H1BB)=Sof(C1C)=Sof(H1CA)=
 Sof(H1CB)=Sof(H1CC)=FVAR(2)
 Sof(O5)=Sof(C1D)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(H1EC)=Sof(C1F)=Sof(H1FA)=
 Sof(H1FB)=Sof(H1FC)=FVAR(3)
5.a Free rotating group:
 O5(C1D,C1E,C1F), O4(C1A,C1B,C1C)
5.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C34(H34A,H34B), C36(H36A,H36B), C38(H38A,H38B), C32A(H32C,
 H32D), C34A(H34C,H34D), C36A(H36C,H36D), C38A(H38C,H38D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C15(H15), C17(H17), C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C25(H25),
  C27(H27), C29(H29), C30(H30), C31(H31)
5.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C33(H33A,H33B,H33C), C33(H33D,H33E,
 H33F), C35(H35A,H35B,H35C), C35(H35D,H35E,H35F), C37(H37A,H37B,H37C), C37(H37D,
 H37E,H37F), C39(H39A,H39B,H39C), C39(H39D,H39E,H39F), C1E(H1EA,H1EB,H1EC),
 C1F(H1FA,H1FB,H1FC), C1B(H1BA,H1BC,H1BB), C1C(H1CA,H1CB,H1CC)
5.e Boron cage BH refined with riding coordinates:
 C1(H1A), B1(H1B), B2(H2), B3(H3A), B4(H4), B5(H5A)
;
_shelx_res_checksum              7187
_shelx_hkl_checksum              34727
_olex2_submission_special_instructions 'No special instructions were received'