Iridium-catalyzed selective amination of B(4)-H for the synthesis of <i>o</i>-carborane-fused indolines.
Zhang, Cai-Yan; Cao, Ke; Liu, Dechun; Yang, Han-Bo; Teng, Chao-Chao; Li, Bo; Yang, Junxiao; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d3dt00316g

data_7712391
_publ_section_title
;
 Iridium-catalyzed selective amination of B(4)-H for the synthesis of
 <i>o</i>-carborane-fused indolines.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt00316g
_journal_year                    2023
_chemical_formula_moiety         'C11 H19 B10 N O2'
_chemical_formula_sum            'C11 H19 B10 N O2'
_chemical_formula_weight         305.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-30 deposited with the CCDC.	2023-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.394(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.480(2)
_cell_length_b                   12.8355(12)
_cell_length_c                   12.6104(13)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.299
_cell_measurement_theta_min      2.308
_cell_volume                     3352.0(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.2214
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_number            6821
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.307
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.745372
_exptl_absorpt_correction_T_min  0.675249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 33989 reflections, Rint = 0.1032
 (10290 with I > 3sig(I), Rint = 0.0554)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         6821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.1045
_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^)+(0.0538P)^2^+6.7029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.2232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3556
_reflns_number_total             6821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00316g2.cif
_cod_data_source_block           4
_cod_database_code               7712391
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.990
_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:
 C7(H7), C4(H4), C21(H21), C23(H23), C6(H6), C24(H24)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C)
2.c Boron cage BH refined with riding coordinates:
 C16(H16), C2(H2), C1(H1), C15(H15), B16(H16A), B21(H21A), B5(H5), B8(H8),
 B20(H20), B11(H11), B6(H6A), B12(H12), B9(H9), B10(H10), B17(H17), B18(H18),
 B7(H7A), B22(H22), B19(H19), B15(H15A)
;
_olex2_submission_special_instructions 'No special instructions were received'