Transition Metal Catalyzed Direct Amination of the Cage B(4)-H Bond in o-Carboranes: Synthesis of Tertiary, Secondary, and Primary o-Carboranyl Amines.
Lyu, Hairong; Quan, Yangjian; Xie, Zuowei; Journal of the American Chemical Society 138 (2016) 12727–12730; doi:10.1021/jacs.6b07086

data_4130811
_publ_section_title
;
 Transition Metal Catalyzed Direct Amination of the Cage B(4)-H Bond in
 o-Carboranes: Synthesis of Tertiary, Secondary, and Primary o-Carboranyl
 Amines.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12727
_journal_page_last               12730
_journal_paper_doi               10.1021/jacs.6b07086
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C10 H25 B10 N O2'
_chemical_formula_weight         299.41
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.799(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0349(17)
_cell_length_b                   18.023(4)
_cell_length_c                   12.072(3)
_cell_measurement_reflns_used    201
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1735.9(7)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24037
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.260
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.039(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1819P)^2^+0.7659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2646
_refine_ls_wR_factor_ref         0.3276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1723
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07086_si_002.cif
_cod_data_source_block           3p
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4130811
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014/6
_shelx_res_checksum              97091
_shelx_hkl_checksum              43054