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_7116993
_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         'C13 H24 B10 O2'
_chemical_formula_sum            'C13 H24 B10 O2'
_chemical_formula_weight         320.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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)
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_audit_update_record
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2015-01-15 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.078(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3151(4)
_cell_length_b                   13.2180(6)
_cell_length_c                   19.6674(9)
_cell_measurement_reflns_used    1424
_cell_measurement_temperature    293.93(10)
_cell_measurement_theta_max      24.2550
_cell_measurement_theta_min      3.7000
_cell_volume                     1898.92(16)
_computing_cell_refinement
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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_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)
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_computing_data_reduction
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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_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      293.93(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -33.00   21.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571   19.0000   90.0000 45

  2 omega  -18.00   24.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000   90.0000 35

  3 omega   54.00   91.20   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000   60.0000 31

  4 omega  -41.00   58.60   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -19.0000   90.0000 83
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0592418000
_diffrn_orient_matrix_UB_12      -0.0424806000
_diffrn_orient_matrix_UB_13      0.0019266000
_diffrn_orient_matrix_UB_21      -0.0658264000
_diffrn_orient_matrix_UB_22      -0.0287421000
_diffrn_orient_matrix_UB_23      -0.0195051000
_diffrn_orient_matrix_UB_31      0.0398304000
_diffrn_orient_matrix_UB_32      0.0157687000
_diffrn_orient_matrix_UB_33      -0.0303387000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7729
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.304
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0694
_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^)+(0.0807P)^2^+0.2727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.2026
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc01331c2.cif
_cod_data_source_block           caok1125
_cod_original_cell_volume        1898.90(15)
_cod_database_code               7116993
_reflns_odcompleteness_completeness 99.63
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C)
2.d Boron cage BH refined with riding coordinates:
 B3(H3), B4(H4), B5(H5), B6(H6A), B7(H7A), B9(H9A), B10(H10A), B11(H11),
 B12(H12)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'