Highly selective palladium-catalyzed one-pot, five-fold B‒H/C‒H cross coupling of monocarboranes with alkenes
Shen, Yunjun; Zhang, Kang; Liang, Xuewei; Dontha, Rakesh; Duttwyler, Simon; Chemical Science  (2019) –; doi:10.1039/C9SC00078J

data_1550690
_publ_section_title
;
 Highly selective palladium-catalyzed one-pot, five-fold B--H/C--H cross
 coupling of monocarboranes with alkenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00078J
_journal_year                    2019
_chemical_formula_moiety         'C6 H15 B11 Br N2 O2 Pd, C3 H10 N'
_chemical_formula_sum            'C9 H25 B11 Br N3 O2 Pd'
_chemical_formula_weight         512.54
_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
_audit_creation_date             2017-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-12-21 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.913(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7468(9)
_cell_length_b                   10.0535(7)
_cell_length_c                   26.411(3)
_cell_measurement_reflns_used    3062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2117
_cell_measurement_theta_min      2.9326
_cell_volume                     2310.1(4)
_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
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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)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -78.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5149    0.0000  150.0000 104

  2 omega  -38.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5149   38.0000 -180.0000 93

  3 omega  -75.00  -17.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5149  144.0000  -98.0000 58

  4 omega  -56.00  -10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8274  144.0000   81.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0376777000
_diffrn_orient_matrix_UB_12      -0.0434900000
_diffrn_orient_matrix_UB_13      -0.0158359000
_diffrn_orient_matrix_UB_21      -0.0436429000
_diffrn_orient_matrix_UB_22      0.0268350000
_diffrn_orient_matrix_UB_23      -0.0217612000
_diffrn_orient_matrix_UB_31      0.0576508000
_diffrn_orient_matrix_UB_32      0.0486410000
_diffrn_orient_matrix_UB_33      -0.0021616000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14906
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.938
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44225
_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    1.474
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.538
_refine_diff_density_min         -1.393
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0974
_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^)+(0.0866P)^2^+30.0175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2903
_reflns_number_total             4195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00078j2.cif
_cod_data_source_block           170517_yjs_br_pd_2nd_pl
_cod_database_code               1550690
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1 PD1 b1'
_shelx_estimated_absorpt_t_max   0.785
_shelx_estimated_absorpt_t_min   0.415
_reflns_odcompleteness_completeness 99.72
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N3(H3A)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,
 H9B,H9C)
2.c Boron cage BH refined with riding coordinates:
 B2(H2), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10)
;
_shelx_res_checksum              81824
_olex2_submission_special_instructions 'No special instructions were received'