Palladium-Catalyzed Selective Five-Fold Cascade Arylation of the 12-Vertex Monocarborane Anion by B-H Activation.
Lin, Furong; Yu, Jing-Lu; Shen, Yunjun; Zhang, Shuo-Qing; Spingler, Bernhard; Liu, Jiyong; Hong, Xin; Duttwyler, Simon; Journal of the American Chemical Society 140 (2018) 13798–13807; doi:10.1021/jacs.8b07872

data_4133012
_publ_section_title
;
 Palladium-Catalyzed Selective Five-Fold Cascade Arylation of the
 12-Vertex Monocarborane Anion by B-H Activation.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13798
_journal_page_last               13807
_journal_paper_doi               10.1021/jacs.8b07872
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C38 H44 B11 O7, 2(C4 H10 N0.5)'
_chemical_formula_sum            'C46 H64 B11 N O7'
_chemical_formula_weight         861.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6242(15)
_cell_length_b                   19.1081(9)
_cell_length_c                   22.3852(10)
_cell_measurement_reflns_used    5499
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3276
_cell_measurement_theta_min      3.1567
_cell_volume                     10105.0(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -48.00    0.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   97.0000 -140.0000 48

  2 omega  -41.00   47.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -30.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0273662000
_diffrn_orient_matrix_UB_12      0.0103711000
_diffrn_orient_matrix_UB_13      -0.0095875000
_diffrn_orient_matrix_UB_21      0.0068991000
_diffrn_orient_matrix_UB_22      -0.0354472000
_diffrn_orient_matrix_UB_23      -0.0059240000
_diffrn_orient_matrix_UB_31      -0.0102753000
_diffrn_orient_matrix_UB_32      0.0037253000
_diffrn_orient_matrix_UB_33      -0.0296019000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29413
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.163
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             3664
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.810
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0796
_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^)+(0.1493P)^2^+0.5156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5310
_reflns_number_total             9195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07872_si_004.cif
_cod_data_source_block           170612_lfr_0409
_cod_database_code               4133012
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'c10 h10 n2 o8 b1'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.44
_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, All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H44D(0.5) H44E(0.5) H44F(0.5) H44A(0.5) H44B(0.5) H44C(0.5)
 H46D(0.5) H46E(0.5) H46F(0.5) H46A(0.5) H46B(0.5) H46C(0.5) C47(0.5) H47A(0.5)
 H47B(0.5) C48(0.5) H48A(0.5) H48B(0.5) C43(0.5) H43A(0.5) H43B(0.5) C45(0.5)
 H45A(0.5) H45B(0.5)
3.a Riding coordinates:
 C48(H48A,H48B)
3.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C41(H41A,H41B), C47(H47A,H47B), C43(H43A,H43B), C45(H45A,H45B)
3.c Me refined with riding coordinates:
 C44(H44D,H44E,H44F), C44(H44A,H44B,H44C), C46(H46D,H46E,H46F), C46(H46A,H46B,
 H46C)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16),
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
3.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,
 H42B,H42C)
3.f Boron cage BH refined with riding coordinates:
 B6(H6A), B7(H7), B8(H8A), B9(H9A), B10(H10), B11(H11)
;
_shelx_res_checksum              47486
_shelx_hkl_checksum              15044
_olex2_submission_special_instructions 'No special instructions were received'