Palladium catalyzed selective arylation of o-carboranes via B(4)-H activation: amide induced regioselectivity reversal.
Xu, Tao-Tao; Cao, Ke; Zhang, Cai-Yan; Wu, Ji; Jiang, Linhai; Yang, Junxiao; Chemical communications (Cambridge, England) 54 (2018) 13603–13606; doi:10.1039/c8cc08193j

data_7122587
_publ_section_title
;
 Palladium catalyzed selective arylation of o-carboranes via B(4)-H
 activation: amide induced regioselectivity reversal.
;
_journal_issue                   96
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13603
_journal_page_last               13606
_journal_paper_doi               10.1039/c8cc08193j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C15 H20 B10 Cl N O'
_chemical_formula_sum            'C15 H20 B10 Cl N O'
_chemical_formula_weight         373.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-30 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.297(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7687(12)
_cell_length_b                   12.8969(17)
_cell_length_c                   15.702(2)
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.047
_cell_measurement_theta_min      2.636
_cell_volume                     1946.4(4)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0627
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13635
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.497
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.057
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0731 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.8917. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0770P)^2^+0.0172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             3603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08193j2.cif
_cod_data_source_block           mo_20180673-x-276_0m
_cod_depositor_comments          'Adding full bibliography for 7122587.cif.'
_cod_original_cell_volume        1946.4(5)
_cod_database_code               7122587
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C8(H8), C7(H7), C6(H6), C5(H5), C15(H15), C14(H14), C12(H12),
 C11(H11)
2.b Boron cage BH refined with riding coordinates:
 C1(H1A), C2(H2), B5(H5A), B3(H3), B8(H8A), B6(H6A), B10(H10), B12(H12A),
 B7(H7A), B11(H11A)
;
_olex2_submission_special_instructions 'No special instructions were received'