Ligand-controlled regiodivergent Ni-catalyzed <i>trans</i>-hydroboration/carboboration of internal alkynes with B<sub>2</sub>pin<sub>2</sub>.
Chen, Zunsheng; Nie, Biao; Li, Xiaoning; Liu, Teng; Li, Chunsheng; Huang, Jiuzhong; Chemical science 15 (2024) 2236–2242; doi:10.1039/d3sc04184k

data_1570694
_publ_section_title
;
 Ligand-controlled regiodivergent Ni-catalyzed
 <i>trans</i>-hydroboration/carboboration of internal alkynes with
 B<sub>2</sub>pin<sub>2</sub>.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2236
_journal_page_last               2242
_journal_paper_doi               10.1039/d3sc04184k
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H26 B N O2'
_chemical_formula_sum            'C23 H26 B N O2'
_chemical_formula_weight         359.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g18ph
_audit_creation_date             2022-10-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-25 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.101(4)
_cell_angle_beta                 103.862(4)
_cell_angle_gamma                102.475(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0732(3)
_cell_length_b                   12.8154(5)
_cell_length_c                   12.8838(5)
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.4160
_cell_measurement_theta_min      3.8450
_cell_volume                     1014.75(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     82.00 123.00   0.50    0.63    --   42.30  77.00 -30.00   82
  2  \w    -46.00  45.00   0.50    0.63    --   42.30 -77.00-180.00  182
  3  \w     86.00 127.00   0.50    0.63    --   42.30  77.00  30.00   82
  4  \w     91.00 117.00   0.50    0.63    --   42.30  77.00  90.00   52
  5  \w    -33.00  77.00   0.50    0.63    --   42.30 -82.00 -60.00  220
  6  \w     15.00 134.00   0.50    0.50    --  101.60 -64.00 -30.00  238
  7  \w     79.00 141.00   0.50    0.50    --  101.60 -77.00 120.00  124
  8  \w     34.00  98.00   0.50    0.50    --  101.60 -64.00 150.00  128
  9  \w    146.00 179.00   0.50    0.50    --  101.60  82.00   0.00   66
 10  \w     87.00 115.00   0.50    0.50    --  101.60  82.00   0.00   56
 11  \w     87.00 191.00   0.50    0.50    --  101.60  82.00 -90.00  208
 12  \w     87.00 126.00   0.50    0.50    --  101.60  82.00-120.00   78
 13  \w     99.00 126.00   0.50    0.50    --  101.60  50.00  60.00   54
 14  \w    150.00 183.00   0.50    0.50    --  101.60  50.00  60.00   66
 15  \w    105.00 131.00   0.50    0.50    --  101.60 -64.00 150.00   52
 16  \w    153.00 178.00   0.50    0.50    --  101.60 -25.00  90.00   50
 17  \w     38.00 124.00   0.50    0.50    --  101.60 -25.00  90.00  172
 18  \w     43.00  69.00   0.50    0.63    --   42.30  57.00-150.00   52
 19  \w     90.00 116.00   0.50    0.63    --   42.30  77.00-120.00   52
 20  \w     85.00 112.00   0.50    0.63    --   42.30  57.00-150.00   54
 21  \w    100.00 126.00   0.50    0.50    --  101.60 -50.00 150.00   52
 22  \w     42.00  68.00   0.50    0.50    --  101.60 -50.00 150.00   52
 23  \w    102.00 128.00   0.50    0.50    --  101.60 -12.00 -30.00   52
 24  \w     45.00  80.00   0.50    0.50    --  101.60 -12.00 -30.00   70
 25  \w    -20.00  71.00   0.50    0.50    --   42.30 -57.00  30.00  182
 26  \w     16.00  82.00   0.50    0.50    --   42.30 -82.00  30.00  132
 27  \w     50.00  76.00   0.50    0.50    --   42.30 -82.00-120.00   52
 28  \w     -4.00  27.00   0.50    0.50    --   42.30 -82.00-120.00   62
 29  \w     65.00 101.00   0.50    0.50    --  101.60 -82.00 120.00   72
 30  \w     14.00  40.00   0.50    0.50    --  101.60 -12.00  30.00   52
 31  \w     83.00 138.00   0.50    0.50    --  101.60 -82.00-180.00  110
 32  \w     82.00 108.00   0.50    0.50    --  101.60 -82.00   0.00   52
 33  \w     13.00  40.00   0.50    0.50    --  101.60 -82.00 120.00   54
 34  \w     64.00 110.00   0.50    0.50    --  101.60 -82.00-120.00   92
 35  \w     94.00 180.00   0.50    0.50    --  101.60 -12.00  30.00  172
 36  \w     73.00 109.00   0.50    0.50    --  101.60 -82.00  60.00   72
 37  \w     70.00 100.00   0.50    0.50    --  101.60  50.00 150.00   60
 38  \w    149.00 175.00   0.50    0.50    --  101.60  50.00 150.00   52
 39  \w     57.00 105.00   0.50    0.50    --  101.60 -50.00-150.00   96
 40  \w     64.00  90.00   0.50    0.50    --  101.60 -12.00  30.00   52
 41  \w     12.00 143.00   0.50    0.50    --  101.60 -82.00 -30.00  262
 42  \w    148.00 175.00   0.50    0.50    --  101.60  50.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495798000
_diffrn_orient_matrix_UB_12      -0.1044082000
_diffrn_orient_matrix_UB_13      0.0205444000
_diffrn_orient_matrix_UB_21      0.1031566000
_diffrn_orient_matrix_UB_22      0.0763793000
_diffrn_orient_matrix_UB_23      0.1314269000
_diffrn_orient_matrix_UB_31      -0.2073923000
_diffrn_orient_matrix_UB_32      -0.0362495000
_diffrn_orient_matrix_UB_33      0.0186915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10644
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.598
_diffrn_reflns_theta_min         3.854
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0838
_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^)+(0.1384P)^2^+0.6023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3460
_reflns_number_total             3847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04184k2.cif
_cod_data_source_block           99-1
_cod_depositor_comments
'Adding full bibliography for 1570693--1570697.cif.'
_cod_original_cell_volume        1014.75(8)
_cod_database_code               1570694
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.919
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              98869
_shelx_hkl_checksum              72969
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.430
_oxdiff_exptl_absorpt_empirical_full_min 0.259