Palladium catalyzed selective mono-arylation of o-carboranes via B-H activation
Ke Cao; Yawen Huang; Junxiao Yang; Ji Wu; Chem.Commun. 51 (2015) 7257–; doi:10.1039/C5cc01331C

data_7116994
_publ_section_title
;
 Palladium catalyzed selective mono-arylation of o-carboranes via B-H
 activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7257
_journal_paper_doi               10.1039/C5cc01331C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C12 H22 B10 O'
_chemical_formula_sum            'C12 H22 B10 O'
_chemical_formula_weight         290.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-14
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-01-15 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.334(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   24.2272(13)
_cell_length_b                   13.0711(6)
_cell_length_c                   23.5734(10)
_cell_measurement_reflns_used    2037
_cell_measurement_temperature    294.29(10)
_cell_measurement_theta_max      21.5650
_cell_measurement_theta_min      3.7450
_cell_volume                     7086.2(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.29(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -17.00    8.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  150.0000 25

  2 omega   68.00   96.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000 -180.0000 28

  3 omega    8.00   90.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000  120.0000 82

  4 omega    6.00   89.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000    0.0000 83

  5 omega  -49.00  -24.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000 -150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0273473000
_diffrn_orient_matrix_UB_12      0.0230852000
_diffrn_orient_matrix_UB_13      -0.0142640000
_diffrn_orient_matrix_UB_21      -0.0141874000
_diffrn_orient_matrix_UB_22      -0.0461777000
_diffrn_orient_matrix_UB_23      0.0030586000
_diffrn_orient_matrix_UB_31      -0.0014014000
_diffrn_orient_matrix_UB_32      0.0167145000
_diffrn_orient_matrix_UB_33      0.0281421000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17538
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.437
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.2095
_refine_ls_R_factor_gt           0.1112
_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^)+(0.1673P)^2^+6.8520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2992
_refine_ls_wR_factor_ref         0.3787
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             6922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01331c2.cif
_cod_data_source_block           222_up
_cod_database_code               7116994
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C6(H6), C6'(H6'), C7'(H7'), C9'(H9'), C10'(H10')
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C12'(H12D,H12E,H12F),
 C3'(H3'A,H3'B,H3'C), C4'(H4'A,H4'B,H4'C)
2.c Boron cage BH refined with riding coordinates:
 B12(H12), B8(H8), B4(H4), B5(H5), B10(H10A), B11(H11), B7(H7A), B3(H3),
 B6(H6A), B4'(H4'), B5'(H5'), B10'(H10B), B12'(H12'), B8'(H8'), B3'(H3'),
 B7'(H7'A), B11'(H11'), B6'(H6'A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'