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_7131037
_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, 0.5(C3 H6 O), 1(C8 H20 N)'
_chemical_formula_sum            'C41.5 H50 B11 Br5 N O2.5'
_chemical_formula_weight         1121.28
_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             2022-09-08
_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                92.876(6)
_cell_angle_beta                 96.299(6)
_cell_angle_gamma                106.337(6)
_cell_formula_units_Z            2
_cell_length_a                   11.455(2)
_cell_length_b                   12.268(2)
_cell_length_c                   17.830(3)
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.009
_cell_measurement_theta_min      2.397
_cell_volume                     2381.3(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.956
_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  0.0969
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45049
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.594
_diffrn_reflns_theta_min         2.307
_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    4.257
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.0834 after correction.
The Ratio of minimum to maximum transmission is 0.5751.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.521
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         10553
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0701
_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^)+(0.1433P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7615
_reflns_number_total             10553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05422a2.cif
_cod_data_source_block           191105_jyj_160_0m
_cod_depositor_comments
'Adding full bibliography for 7131036--7131040.cif.'
_cod_original_cell_volume        2381.3(8)
_cod_original_formula_sum        'C41.50 H50 B11 Br5 N O2.50'
_cod_database_code               7131037
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.727
_shelx_estimated_absorpt_t_min   0.549
_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 O(H) groups
2. Shared sites
{N1A, N1}
3. Restrained distances
 N1A-C39A \\sim N1-C33 \\sim N1-C39 \\sim N1A-C33A \\sim N1A-C37A \\sim N1-C37
\\sim N1A-C35A
 with sigma of 0.02
 C40A-C39A \\sim C40-C39 \\sim C34-C33 \\sim C35A-C36A \\sim C33A-C34A \\sim
C36-C35 \\sim C38-C37 ~
 C38A-C37A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(O3) = Uiso(C41) = Uiso(C43) = Uiso(O1A) = Uiso(C41A) = Uiso(C43A) =
Uiso(C42A) = Uiso(C42)
Uiso(N1A) = Uiso(N1)
5. Rigid body (RIGU) restrains
 N1A, C33A, C34A, C35A, C36A, C37A, C38A, C39A, C40A, N1, C33, C34, C35, C36,
 C37, C38, C39, C40
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(N1)=Sof(C33)=Sof(H33C)=Sof(H33D)=Sof(C34)=Sof(H34D)=Sof(H34E)=Sof(H34F)=
 Sof(C35)=Sof(H35C)=Sof(H35D)=Sof(C36)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(C37)=
 Sof(H37C)=Sof(H37D)=Sof(C38)=Sof(H38D)=Sof(H38E)=Sof(H38F)=Sof(C39)=Sof(H39C)=
 Sof(H39D)=Sof(C40)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(1)
 Sof(N1A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=Sof(H34B)=
 Sof(H34C)=Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(C38A)=Sof(H38A)=Sof(H38B)=
 Sof(H38C)=Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(C40A)=Sof(H40A)=Sof(H40B)=
 Sof(H40C)=FVAR(1)
 Sof(O1A)=Sof(C41A)=Sof(C42A)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C43A)=
 Sof(H43A)=Sof(H43B)=Sof(H43C)=0.5*(1-FVAR(3))
 Sof(O3)=Sof(C41)=Sof(C42)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(C43)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=0.5*FVAR(3)
7.a Free rotating group:
 O1A(C41A,C42A,C43A), O3(C41,C42,C43)
7.b Secondary CH2 refined with riding coordinates:
 C33A(H33A,H33B), C35A(H35A,H35B), C37A(H37A,H37B), C39A(H39A,H39B), C33(H33C,
 H33D), C35(H35C,H35D), C37(H37C,H37D), C39(H39C,H39D)
7.c Me refined with riding coordinates:
 C42A(H42A,H42B,H42C), C43A(H43A,H43B,H43C), C42(H42D,H42E,H42F), C43(H43D,
 H43E,H43F)
7.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29), C31(H31), C32(H32)
7.e Idealised Me refined as rotating group:
 C34A(H34A,H34B,H34C), C36A(H36A,H36B,H36C), C38A(H38A,H38B,H38C), C40A(H40A,
 H40B,H40C), C34(H34D,H34E,H34F), C36(H36D,H36E,H36F), C38(H38D,H38E,H38F),
 C40(H40D,H40E,H40F)
7.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
7.g Boron cage BH refined with riding coordinates:
 C1(H1A), B1(H1B), B2(H2), B3(H3), B4(H4A), B5(H5A)
;
_shelx_res_checksum              17037
_shelx_hkl_checksum              39662
_olex2_submission_special_instructions 'No special instructions were received'