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_1570696
_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         'C22 H24 B N O2'
_chemical_formula_sum            'C22 H24 B N O2'
_chemical_formula_weight         345.23
_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.cc2hmdsb
_audit_creation_date             2023-11-30
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                79.933(2)
_cell_angle_beta                 89.723(2)
_cell_angle_gamma                76.120(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1597(2)
_cell_length_b                   10.2937(2)
_cell_length_c                   11.2498(3)
_cell_measurement_reflns_used    10955
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.4480
_cell_measurement_theta_min      3.9780
_cell_volume                     1123.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.958
_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    -70.00  17.00   0.50    0.20    --  -48.13  87.00 -38.00  174
  2  \w   -105.00 -80.00   0.50    0.40    -- -104.00  87.00 -38.00   50
  3  \w    -41.00 -15.00   0.50    0.20    --  -48.13 125.00  60.00   52
  4  \w    -64.00 -32.00   0.50    0.40    -- -104.00  57.00 150.00   64
  5  \w    -57.00 -32.00   0.50    0.40    -- -104.00  57.00 120.00   50
  6  \w    -86.00 -60.00   0.50    0.40    -- -104.00  77.00  90.00   52
  7  \w    -61.00 -32.00   0.50    0.40    -- -104.00  57.00-120.00   58
  8  \w    -59.00 -32.00   0.50    0.40    -- -104.00  57.00-180.00   54
  9  \w    -37.00  18.00   0.50    0.20    --  -48.13  38.00 -90.00  110
 10  \w    -40.00  12.00   0.50    0.20    --  -48.13  38.00-150.00  104
 11  \w    144.00 173.00   0.50    0.40    --  104.75  38.00  90.00   58
 12  \w     86.00 154.00   0.50    0.40    --  104.75  87.00 -38.00  136
 13  \w     93.00 135.00   0.50    0.40    --  104.75  57.00 -90.00   84
 14  \w    148.00 173.00   0.50    0.40    --  104.75  57.00 -90.00   50
 15  \w     94.00 177.00   0.50    0.40    --  104.75  38.00-120.00  166
 16  \w     21.00  55.00   0.50    0.20    --   48.13-125.00 120.00   68
 17  \w     37.00  63.00   0.50    0.40    --  104.75 -99.00  30.00   52
 18  \w     38.00 111.00   0.50    0.40    --  104.75-125.00   0.00  146
 19  \w     44.00 106.00   0.50    0.40    --  104.75 -99.00  60.00  124
 20  \w     47.00 102.00   0.50    0.40    --  104.75 -99.00 120.00  110
 21  \w     73.00 106.00   0.50    0.40    --  104.75 -99.00 -30.00   66
 22  \w     51.00 100.00   0.50    0.40    --  104.75 -99.00 -60.00   98
 23  \w     67.00  98.00   0.50    0.40    --  104.75 -99.00-120.00   62
 24  \w     36.00 100.00   0.50    0.40    --  104.75-125.00-150.00  128
 25  \w     48.00 108.00   0.50    0.40    --  104.75-107.00-141.20  120
 26  \w     58.00  84.00   0.50    0.40    --  104.75 -87.00-155.00   52
 27  \w      1.00  56.00   0.50    0.20    --   48.13 -87.00-155.00  110
 28  \w     66.00 100.00   0.50    0.40    --  104.75 -99.00  30.00   68
 29  \w     42.00  68.00   0.50    0.40    --  104.75 -77.00  90.00   52
 30  \w     71.00  96.00   0.50    0.40    --  104.75 -77.00  90.00   50
 31  \w     36.00  64.00   0.50    0.40    --  104.75 -57.00   0.00   56
 32  \w     42.00  68.00   0.50    0.40    --  104.75 -57.00 -30.00   52
 33  \w     37.00  66.00   0.50    0.40    --  104.75 -57.00-120.00   58
 34  \w     42.00  67.00   0.50    0.40    --  104.75 -57.00-150.00   50
 35  \w    -23.00  28.00   0.50    0.20    --   48.13 -19.00 -60.00  102
 36  \w    -17.00  45.00   0.50    0.20    --   48.13 -38.00  30.00  124
 37  \w   -168.00-134.00   0.50    0.40    -- -104.00 -19.00 -30.00   68
 38  \w   -171.00 -97.00   0.50    0.40    -- -104.00 -38.00  60.00  148
 39  \w   -124.00 -94.00   0.50    0.40    -- -104.00 -19.00 -30.00   60
 40  \w   -157.00-117.00   0.50    0.40    -- -104.00 -87.00-155.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0757286000
_diffrn_orient_matrix_UB_12      0.1144938000
_diffrn_orient_matrix_UB_13      -0.0154026000
_diffrn_orient_matrix_UB_21      0.0486089000
_diffrn_orient_matrix_UB_22      -0.0341531000
_diffrn_orient_matrix_UB_23      -0.1233381000
_diffrn_orient_matrix_UB_31      -0.1278119000
_diffrn_orient_matrix_UB_32      0.1013722000
_diffrn_orient_matrix_UB_33      -0.0626400000
_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  0.0166
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13108
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.549
_diffrn_reflns_theta_min         3.994
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0691P)^2^+0.7494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4316
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04184k2.cif
_cod_data_source_block           h-385-1
_cod_depositor_comments
'Adding full bibliography for 1570693--1570697.cif.'
_cod_database_code               1570696
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.929
_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:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              29444
_shelx_hkl_checksum              4831
_shelx_fab_checksum              34759
_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.749