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_1550689
_publ_section_title
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 Highly selective palladium-catalyzed one-pot, five-fold B--H/C--H cross
 coupling of monocarboranes with alkenes
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_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00078J
_journal_year                    2019
_chemical_formula_moiety         'C8 H20 N, C41 H42 B11'
_chemical_formula_sum            'C49 H62 B11 N'
_chemical_formula_weight         783.90
_space_group_crystal_system      orthorhombic
_space_group_IT_number           72
_space_group_name_Hall           '-I 2 2c'
_space_group_name_H-M_alt        'I b a m'
_symmetry_space_group_name_Hall  '-I 2 2c'
_symmetry_space_group_name_H-M   'I b a m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-22 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5746(11)
_cell_length_b                   18.8529(6)
_cell_length_c                   22.1333(6)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.777
_cell_measurement_theta_min      4.082
_cell_volume                     9837.1(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      296
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            52103
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.098
_diffrn_reflns_theta_min         3.475
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1605 before and 0.0975 after correction. The Ratio of minimum to maximum transmission is 0.7492. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       block
_exptl_crystal_F_000             3344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4797
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+6.7857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2591
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3107
_reflns_number_total             4797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00078j2.cif
_cod_data_source_block           wmj18087
_cod_database_code               1550689
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.949
_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. Uiso/Uaniso restraints and constraints
C18 \\sim C19 \\sim C18A \\sim C19A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H29D(0.5) H29E(0.5) H29F(0.5) H29A(0.5) H29B(0.5) H29C(0.5)
 C28(0.5) H28A(0.5) H28B(0.5) C28A(0.5) H28C(0.5) H28D(0.5) H15(0.5) H15A(0.5)
 C13(0.5) H13(0.5) C14(0.5) H14(0.5) C18(0.25) H18(0.25) C19(0.25) H19(0.25)
 C13A(0.5) H13A(0.5) C14A(0.5) H14A(0.5) C18A(0.25) H18A(0.25) C19A(0.25)
 H19A(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C28(H28A,H28B), C28A(H28C,H28D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C15(H15), C15(H15A), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C13(H13), C14(H14), C18(H18), C19(H19), C13A(H13A),
 C14A(H14A), C18A(H18A), C19A(H19A)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C29(H29D,H29E,H29F), C29(H29A,H29B,H29C)
4.d Boron cage BH refined with riding coordinates:
 C1(H1), B4(H4), B5(H5A), B6(H6A), B7(H7A)
;
_shelx_res_checksum              29215
_shelx_fab_checksum              49657
_olex2_submission_special_instructions 'No special instructions were received'