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_1550691
_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         'C42 H42 B11 O2, C3 H6 O, C8 H20 N'
_chemical_formula_sum            'C53 H68 B11 N O3'
_chemical_formula_weight         885.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-12-21 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9981(3)
_cell_length_b                   20.7041(4)
_cell_length_c                   21.3976(4)
_cell_measurement_reflns_used    8577
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      45.759
_cell_measurement_theta_min      3.599
_cell_volume                     5308.52(19)
_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      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0662
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            50116
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.945
_diffrn_reflns_theta_min         3.599
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1082 before and 0.0544 after correction. The Ratio of minimum to maximum transmission is 0.8500. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         10024
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0991
_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^)+(0.1668P)^2^+3.2732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2591
_refine_ls_wR_factor_ref         0.3133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5609
_reflns_number_total             10024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00078j2.cif
_cod_data_source_block           wmj18065_0m
_cod_database_code               1550691
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.976
_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
2. Uiso/Uaniso restraints and constraints
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim
C36' \\sim C37' \\sim C38' \\sim C39' \\sim C40' \\sim C41' \\sim C42': within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H35(0.5) H35A(0.5) C36(0.5) H36(0.5) C37(0.5) C38(0.5) H38(0.5)
 C39(0.5) H39(0.5) C40(0.5) H40(0.5) C41(0.5) H41(0.5) C42(0.5) H42(0.5)
 C36'(0.5) H36'(0.5) C37'(0.5) C42'(0.5) H42'(0.5) C41'(0.5) H41'(0.5)
 C40'(0.5) H40'(0.5) C39'(0.5) H39'(0.5) C38'(0.5) H38'(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C45(H45A,H45B), C47(H47A,H47B), C49(H49A,H49B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C35(H35A), C36(H36),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C36'(H36'), C42'(H42'),
 C41'(H41'), C40'(H40'), C39'(H39'), C38'(H38')
4.c Fitted hexagon refined as free rotating group:
 C37(C38,C39,C40,C41,C42), C37'(C42',C41',C40',C39',C38')
4.d Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C44(H44A,H44B,H44C), C46(H46A,H46B,
 H46C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C)
4.e Boron cage BH refined with riding coordinates:
 B6(H6A), B7(H7A), B8(H8A), B9(H9A), B10(H10A), B11(H11A)
;
_shelx_res_checksum              5076
_olex2_submission_special_instructions 'No special instructions were received'