B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.
Dziedzic, Rafal M.; Saleh, Liban M. A.; Axtell, Jonathan C.; Martin, Joshua L.; Stevens, Simone L.; Royappa, A. Timothy; Rheingold, Arnold L.; Spokoyny, Alexander M.; Journal of the American Chemical Society 138 (2016) 9081–9084; doi:10.1021/jacs.6b05505

data_4125156
_publ_section_title
;
 B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling
 of B-Bromo-Carboranes.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9081
_journal_page_last               9084
_journal_paper_doi               10.1021/jacs.6b05505
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C10 H21 B10 N O2'
_chemical_formula_sum            'C10 H21 B10 N O2'
_chemical_formula_weight         295.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                100.156(2)
_cell_angle_beta                 98.573(2)
_cell_angle_gamma                96.338(2)
_cell_formula_units_Z            8
_cell_length_a                   12.7259(7)
_cell_length_b                   12.9299(7)
_cell_length_c                   20.6344(10)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.35
_cell_volume                     3272.0(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            60279
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.159
_diffrn_reflns_theta_min         2.069
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.2612
_exptl_absorpt_correction_T_min  0.2226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0607 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.8522.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         14448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0792P)^2^+1.3370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9736
_reflns_number_total             14448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05505_si_002.cif
_cod_data_source_block           spok33_a
_cod_depositor_comments
'Adding full bibliography for 4125150--4125156.cif.'
_cod_database_code               4125156
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1A(H1A), N1B(H1B), N00C(H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6A(H6A), C8A(H8A), C4B(H4B), C6B(H6B), C8B(H8B), N1C(H1C),
 C4C(H4C), C6C(H6C), C8C(H8C), C4D(H4D), C6D(H6D), C8D(H8D)
2.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C9B(H9BA,H9BB,H9BC), C10B(H10E,
 H10F,H10G), C9C(H9CA,H9CB,H9CC), C10C(H10I,H10J,H10K), C9D(H9DA,H9DB,H9DC),
 C10D(H10M,H10N,H10O)
2.d Boron cage BH refined with riding coordinates:
 C1A(H1AA), C2A(H2A), B2A(H2AA), B3A(H3A), B4A(H4AA), B5A(H5A), B6A(H6AA),
 B7A(H7A), B8A(H8AA), B9A(H9A), B10A(H10D), C1B(H1BA), C2B(H2B), B2B(H2BA),
 B3B(H3B), B4B(H4BA), B5B(H5B), B6B(H6BA), B7B(H7B), B8B(H8BA), B9B(H9B),
 B10B(H10H), C1C(H1CA), C2C(H2C), B2C(H2CA), B3C(H3C), B4C(H4CA), B5C(H5C),
 B6C(H6CA), B7C(H7C), B8C(H8CA), B9C(H9C), B10C(H10L), C1D(H1D), C2D(H2D),
 B2D(H2DA), B3D(H3D), B4D(H4DA), B5D(H5D), B6D(H6DA), B7D(H7D), B8D(H8DA),
 B9D(H9D), B10D(H10P)
;
_shelx_res_checksum              62280
_shelx_hkl_checksum              56198
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'