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_7131038
_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         'C41 H34 B11 N6 O, C8 H20 N, C3 H6 O'
_chemical_formula_sum            'C52 H60 B11 N7 O2'
_chemical_formula_weight         933.98
_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             2022-09-09
_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                100.693(3)
_cell_angle_beta                 90.559(3)
_cell_angle_gamma                101.575(3)
_cell_formula_units_Z            2
_cell_length_a                   10.7770(9)
_cell_length_b                   16.0486(13)
_cell_length_c                   16.0708(11)
_cell_measurement_reflns_used    5400
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.259
_cell_measurement_theta_min      2.384
_cell_volume                     2672.5(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            44282
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.524
_diffrn_reflns_theta_min         2.270
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1405 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     771
_refine_ls_number_reflns         10994
_refine_ls_number_restraints     313
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0691P)^2^+0.5060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6442
_reflns_number_total             10994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05422a2.cif
_cod_data_source_block           mo_220406_jyj_577_0m
_cod_depositor_comments
'Adding full bibliography for 7131036--7131040.cif.'
_cod_database_code               7131038
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.993
_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. Restrained distances
 N7-C42 \\sim N7-C42A
 with sigma of 0.02
 N7-C48 \\sim N7-C48A
 with sigma of 0.02
 N7-C44 \\sim N7-C44A
 with sigma of 0.02
 N7-C46 \\sim N7-C46A
 with sigma of 0.02
 C43-C42 \\sim C43A-C42A
 with sigma of 0.02
 C49-C48 \\sim C49A-C48A
 with sigma of 0.02
 C47-C46 \\sim C47A-C46A
 with sigma of 0.02
 C45-C44 \\sim C45A-C44A
 with sigma of 0.02
 N7-C43 \\sim N7-C43A
 with sigma of 0.04
 N7-C49 \\sim N7-C49A
 with sigma of 0.04
 N7-C47 \\sim N7-C47A
 with sigma of 0.04
 N7-C45 \\sim N7-C45A
 with sigma of 0.04
 O2-C50 \\sim O2A-C50A
 with sigma of 0.02
 C50-C51 \\sim C50A-C51A
 with sigma of 0.02
 C50-C52 \\sim C50A-C52A
 with sigma of 0.02
 O2-C51 \\sim O2A-C51A
 with sigma of 0.04
 O2-C52 \\sim O2A-C52A
 with sigma of 0.04
 C51-C52 \\sim C51A-C52A
 with sigma of 0.04
3. Rigid bond restraints
 C48A, C49A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
N7 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim
C49 \\sim C42A \\sim C43A \\sim C44A \\sim C45A \\sim C46A \\sim C47A \\sim
C48A \\sim C49A: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
O2 \\sim C50 \\sim C51 \\sim C52 \\sim O2A \\sim C50A \\sim C51A \\sim C52A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
5. Others
 Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=
 Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=
 Sof(C46A)=Sof(H46C)=Sof(H46D)=Sof(C47A)=Sof(H47D)=Sof(H47E)=Sof(H47F)=
 Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49D)=Sof(H49E)=Sof(H49F)=1-FVAR(1)
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C44)=
 Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(C46)=Sof(H46A)=
 Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(H47C)=Sof(C48)=Sof(H48A)=Sof(H48B)=
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=FVAR(1)
 Sof(O2A)=Sof(C50A)=Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52A)=
 Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(O2)=Sof(C50)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(H52A)=
 Sof(H52B)=Sof(H52C)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C42(H42A,H42B), C44(H44A,
 H44B), C46(H46A,H46B), C48(H48A,H48B), C42A(H42C,H42D), C44A(H44C,H44D),
 C46A(H46C,H46D), C48A(H48C,H48D)
6.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C26(H26), C29(H29), C30(H30), C32(H32), C33(H33),
  C36(H36), C37(H37), C39(H39), C40(H40)
6.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C49(H49A,H49B,
 H49C), C43A(H43D,H43E,H43F), C45A(H45D,H45E,H45F), C47A(H47D,H47E,H47F),
 C49A(H49D,H49E,H49F), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C51A(H51D,H51E,
 H51F), C52A(H52D,H52E,H52F)
6.d Boron cage BH refined with riding coordinates:
 C1(H1), B1(H1A), B2(H2), B3(H3), B4(H4), B5(H5)
;
_shelx_res_checksum              76875
_shelx_hkl_checksum              31851
_olex2_submission_special_instructions 'No special instructions were received'